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Formaldehyde

February 15, 2024

"Methanal" redirects here. Not to be confused with Methanol or Menthol.
For other uses, see Formaldehyde (disambiguation).

Formaldehyde (/fɔːrˈmældɪhaɪd/ ⓘ for-MAL-di-hide, US also /fər-/ ⓘ fər-) (systematic name methanal) is an organic compound with the formula CH2O and structure H−CHO. The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as aqueous solutions (formalin), which consists mainly of the hydrate CH2(OH)2. It is the simplest of the aldehydes (R−CHO). As a precursor to many other materials and chemical compounds, in 2006 the global production of formaldehyde was estimated at 12 million tons per year.[14] It is mainly used in the production of industrial resins, e.g., for particle board and coatings. Small amounts also occur naturally.

Formaldehyde
Structural formula of formaldehyde (with hydrogens)
Spacefill model of formaldehyde
Names
Preferred IUPAC name
Formaldehyde[1]
Systematic IUPAC name
Methanal[1]
Other names
Methyl aldehyde
Methylene glycol (diol forms in aqueous solution)
Methylene oxide
Formalin (aqueous solution)
Formol
Carbonyl hydride
Methanone
Oxomethane
Identifiers
  • 50-00-0 Y
3D model (JSmol)
  • Interactive image
3DMet
  • B00018
1209228
ChEBI
  • CHEBI:16842 Y
ChEMBL
  • ChEMBL1255 Y
ChemSpider
  • 692 Y
DrugBank
  • DB03843 Y
ECHA InfoCard 100.000.002
EC Number
  • 200-001-8
E number E240 (preservatives)
445
  • 4196
KEGG
  • D00017 Y
MeSH Formaldehyde
  • 712
RTECS number
  • LP8925000
UNII
  • 1HG84L3525 Y
UN number 2209
  • DTXSID7020637
  • InChI=1S/CH2O/c1-2/h1H2 Y
    Key: WSFSSNUMVMOOMR-UHFFFAOYSA-N Y
  • InChI=1/CH2O/c1-2/h1H2
    Key: WSFSSNUMVMOOMR-UHFFFAOYAT
  • C=O
Properties[7]
CH2O
Molar mass 30.026 g·mol−1
Appearance Colorless gas
Density 0.8153 g/cm3 (−20 °C)[2] (liquid)
Melting point −92 °C (−134 °F; 181 K)
Boiling point −19 °C (−2 °F; 254 K)[2]
400 g/L
log P 0.350
Vapor pressure > 1 atm[3]
Acidity (pKa) 13.27 (hydrate)[4][5]
−18.6·10−6 cm3/mol
2.330 D[6]
Structure
C2v
Trigonal planar
Thermochemistry[8]
35.387 J·mol−1·K−1
218.760 J·mol−1·K−1
−108.700 kJ·mol−1
−102.667 kJ·mol−1
571 kJ·mol−1
Pharmacology
QP53AX19 (WHO)
Hazards
GHS labelling:
[9]
Danger
H301, H311, H314, H317, H331, H335, H341, H350, H370[9]
P201, P280, P303+P361+P353, P304+P340+P310, P305+P351+P338, P308+P310[9]
NFPA 704 (fire diamond)
Health 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazard COR: Corrosive; strong acid or base. E.g. sulfuric acid, potassium hydroxide
4
4
0
COR
Flash point 64 °C (147 °F; 337 K)
430 °C (806 °F; 703 K)
Explosive limits 7–73%
Lethal dose or concentration (LD, LC):
100 mg/kg (oral, rat)[12]
333 ppm (mouse, 2 h)
815 ppm (rat, 30 min)[13]
333 ppm (cat, 2 h)[13]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.75 ppm ST 2 ppm (as formaldehyde and formalin)[10][11]
REL (Recommended)
 Ca TWA 0.016 ppm C 0.1 ppm [15-minute][10]
IDLH (Immediate danger)
 Ca [20 ppm][10]
Safety data sheet (SDS) MSDS()
Related compounds
Related aldehydes
 Acetaldehyde

Butyraldehyde
Decanal
Heptanal
Hexanal
Nonanal
Octadecanal
Octanal
Pentanal
Propionaldehyde

Related compounds
 Methanol
Formic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Formaldehyde is classified as a carcinogen[note 1] and can cause respiratory and skin irritation upon exposure.[15]

Forms edit

Formaldehyde is more complicated than many simple carbon compounds in that it adopts several diverse forms. These compounds can often be used interchangeably and can be interconverted.

  • Molecular formaldehyde. A colorless gas with a characteristic pungent, irritating odor. It is stable at about 150 °C, but polymerizes when condensed to a liquid.
  • 1,3,5-Trioxane, with the formula (CH2O)3. It is a white solid that dissolves without degradation in organic solvents. It is a trimer of molecular formaldehyde.
  • Paraformaldehyde, with the formula HO(CH2O)nH. It is a white solid that is insoluble in most solvents.
  • Methanediol, with the formula CH2(OH)2. This compound also exists in equilibrium with various oligomers (short polymers), depending on the concentration and temperature. A saturated water solution, of about 40% formaldehyde by volume or 37% by mass, is called "100% formalin".

A small amount of stabilizer, such as methanol, is usually added to suppress oxidation and polymerization. A typical commercial-grade formalin may contain 10–12% methanol in addition to various metallic impurities.

"Formaldehyde" was first used as a generic trademark in 1893 following a previous trade name, "formalin".[16]

  • Main forms of formaldehyde
  •  
    Monomeric formaldehyde (subject of this article)
  •  
    Trioxane is a stable cyclic trimer of formaldehyde.
  •  
    Paraformaldehyde is a common form of formaldehyde for industrial applications.
  •  
    Methanediol, the predominant species in dilute aqueous solutions of formaldehyde

Structure and bonding edit

Molecular formaldehyde contains a central carbon atom with a double bond to the oxygen atom and a single bond to each hydrogen atom. This structure is summarised by the condensed formula H2C=O.[17] The molecule is planar, Y-shaped and its molecular symmetry belongs to the C2v point group.[18] The precise molecular geometry of gaseous formaldehyde has been determined by gas electron diffraction[17][19] and microwave spectroscopy.[20][21] The bond lengths are 1.21 Å for the carbon–oxygen bond[17][19][20][21][22] and around 1.11 Å for the carbon–hydrogen bond,[17][19][20][21] while the H–C–H bond angle is 117°,[20][21] close to the 120° angle found in an ideal trigonal planar molecule.[17] Some excited electronic states of formaldehyde are pyramidal rather than planar as in the ground state.[22]

Occurrence edit

Processes in the upper atmosphere contribute up to 90% of the total formaldehyde in the environment. Formaldehyde is an intermediate in the oxidation (or combustion) of methane, as well as of other carbon compounds, e.g. in forest fires, automobile exhaust, and tobacco smoke. When produced in the atmosphere by the action of sunlight and oxygen on atmospheric methane and other hydrocarbons, it becomes part of smog. Formaldehyde has also been detected in outer space.

Formaldehyde and its adducts are ubiquitous in nature. Food may contain formaldehyde at levels 1–100 mg/kg.[23] Formaldehyde, formed in the metabolism of the amino acids serine and threonine, is found in the bloodstream of humans and other primates at concentrations of approximately 50 micromolar.[24] Experiments in which animals are exposed to an atmosphere containing isotopically labeled formaldehyde have demonstrated that even in deliberately exposed animals, the majority of formaldehyde-DNA adducts found in non-respiratory tissues are derived from endogenously produced formaldehyde.[25]

Formaldehyde does not accumulate in the environment, because it is broken down within a few hours by sunlight or by bacteria present in soil or water. Humans metabolize formaldehyde quickly, converting it to formic acid, so it does not accumulate.[26][27] It nonetheless presents significant health concerns, as a contaminant.

Interstellar formaldehyde edit

Main article: Interstellar formaldehyde

Formaldehyde appears to be a useful probe in astrochemistry due to prominence of the 110←111 and 211←212 K-doublet transitions. It was the first polyatomic organic molecule detected in the interstellar medium.[28] Since its initial detection in 1969, it has been observed in many regions of the galaxy. Because of the widespread interest in interstellar formaldehyde, it has been extensively studied, yielding new extragalactic sources.[29] A proposed mechanism for the formation is the hydrogenation of CO ice:[30]

H + CO → HCO
HCO + H → CH2O

HCN, HNC, H2CO, and dust have also been observed inside the comae of comets C/2012 F6 (Lemmon) and C/2012 S1 (ISON).[31][32]

Synthesis and industrial production edit

Laboratory synthesis edit

Formaldehyde was first reported in 1859 by the Russian chemist Aleksandr Butlerov (1828–1886).[33] In his paper, Butlerov referred to formaldehyde as "dioxymethylen" (methylene dioxide) [page 247] because his empirical formula for it was incorrect (C4H4O4). It was conclusively identified by August Wilhelm von Hofmann, who first announced the production of formaldehyde by passing methanol vapor in air over hot platinum wire.[34][35] With modifications, Hoffmann's method remains the basis of the present day industrial route.

Solution routes to formaldehyde also entail oxidation of methanol or methyl iodide.[36]

Industry edit

Formaldehyde is produced industrially by the catalytic oxidation of methanol. The most common catalysts are silver metal, iron(III) oxide,[37] iron molybdenum oxides [e.g. iron(III) molybdate] with a molybdenum-enriched surface,[38] or vanadium oxides. In the commonly used formox process, methanol and oxygen react at c. 250–400 °C in presence of iron oxide in combination with molybdenum and/or vanadium to produce formaldehyde according to the chemical equation:[39]

2 CH3OH + O2 → 2 CH2O + 2 H2O

The silver-based catalyst usually operates at a higher temperature, about 650 °C. Two chemical reactions on it simultaneously produce formaldehyde: that shown above and the dehydrogenation reaction:

CH3OH → CH2O + H2

In principle, formaldehyde could be generated by oxidation of methane, but this route is not industrially viable because the methanol is more easily oxidized than methane.[39]

Biochemistry edit

Formaldehyde is produced via several enzyme-catalyzed routes.[40] Living beings, including humans, produce formaldehyde as part of their metabolism. Formaldehyde are key to several bodily functions (e.g. epigenetics[24]), but its amount must also be tightly controlled to avoid self-poisioning.[41]

  • Serine hydroxymethyltransferase can decompose serine into formaldehyde and glycine, according to this reaction: HOCH2CH(NH2)CO2H → CH2O + H2C(NH2)CO2H.
  • methylotrophic microbes convert methanol into formaldehyde and energy via methanol dehydrogenase: CH3OH → CH2O + 2e− + 2H+
  • Other routes to formaldehyde include oxidative demethylations, semicarbazide-sensitive amine oxidases, dimethylglycine dehydrogenases, lipid peroxidases, P450 oxidases, and N-methyl group demethylases.[40]

Formaldehyde is catabolized by alcohol dehydrogenase ADH5 and aldehyde dehydrogenase ALDH2.[42]

Organic chemistry edit

Formaldehyde is a building block in the synthesis of many other compounds of specialised and industrial significance. It exhibits most of the chemical properties of other aldehydes but is more reactive.

Polymerization and hydration edit

Gaseous formaldehyde polymerizes on the active sites of the vessel walls, but the mechanism of the reaction is unknown.[43] Small amounts of hydrogen chloride (or boron trifluoride, or stannic chloride) present in gaseous formaldehyde provide the catalytic effect and make the polymerization rapid.[44] Monomeric CH2O is a gas and is rarely encountered in the laboratory.

Formaldehyde in aqueous solutions, unlike some other small aldehydes (which need specific conditions to oligomerize through aldol condensation) oligomerizes spontaneously at a common state. The trimer is 1,3,5-trioxane ((CH2O)3) is typical oligomer. Many cyclic oligomers of other sizes have been isolated. Similarly, formaldehyde hydrates to give the geminal diol methanediol, which condenses further to form hydroxy-terminated oligomers HO(CH2O)nH. The polymer is called paraformaldehyde. The higher concentration of formaldehyde—the more equilibrium shifts towards polymerization. Diluting with water or increasing the solution temperature, as well as adding alcohols (such as methanol or ethanol) lowers that tendency.

Oxidation and reduction edit

It is readily oxidized by atmospheric oxygen into formic acid. For this reason, commercial formaldehyde is typically contaminated with formic acid. Formaldehyde can be hydrogenated into methanol.

In the Cannizzaro reaction, formaldehyde and base react to produce formic acid and methanol, a disproportionation reaction.

Hydroxymethylation and chloromethylation edit

Formaldehyde reacts with many compounds, resulting in hydroxymethylation:

X-H + CH2O → X-CH2OH

(X = R2N, RC(O)NR', SH). The resulting hydroxymethyl derivatives typically react further. Thus, amines give hexahydro-1,3,5-triazines:

3 RNH2 + 3 CH2O → (RNCH2)3 + 3 H2O

Similarly, when combined with hydrogen sulfide, it forms trithiane:[45]

3 CH2O + 3 H2S → (CH2S)3 + 3 H2O

In the presence of acids, it participates in electrophilic aromatic substitution reactions with aromatic compounds resulting in hydroxymethylated derivatives:

ArH + CH2O → ArCH2OH

When conducted in the presence of hydrogen chloride, the product is the chloromethyl compound, as described in the Blanc chloromethylation. If the arene is electron-rich, as in phenols, elaborate condensations ensue. With 4-substituted phenols one obtains calixarenes.[46] Phenol results in polymers.

Other reactions edit

Many amino acids react with formaldehyde.[40] Cysteine converts to thioproline.

Uses edit

Industrial applications edit

Formaldehyde is a common precursor to more complex compounds and materials. In approximate order of decreasing consumption, products generated from formaldehyde include urea formaldehyde resin, melamine resin, phenol formaldehyde resin, polyoxymethylene plastics, 1,4-butanediol, and methylene diphenyl diisocyanate.[39] The textile industry uses formaldehyde-based resins as finishers to make fabrics crease-resistant.[47]

 
Two steps in formation of urea-formaldehyde resin, which is widely used in the production of particle board

When treated with phenol, urea, or melamine, formaldehyde produces, respectively, hard thermoset phenol formaldehyde resin, urea formaldehyde resin, and melamine resin. These polymers are permanent adhesives used in plywood and carpeting. They are also foamed to make insulation, or cast into moulded products. Production of formaldehyde resins accounts for more than half of formaldehyde consumption.

Formaldehyde is also a precursor to polyfunctional alcohols such as pentaerythritol, which is used to make paints and explosives. Other formaldehyde derivatives include methylene diphenyl diisocyanate, an important component in polyurethane paints and foams, and hexamine, which is used in phenol-formaldehyde resins as well as the explosive RDX.

 

Condensation with acetaldehyde affords pentaerythritol, a chemical necessary in synthesizing PETN, a high explosive.[48] Condensation with phenols gives phenol-formaldehyde resins.

Niche uses edit

Disinfectant and biocide edit

An aqueous solution of formaldehyde can be useful as a disinfectant as it kills most bacteria and fungi (including their spores). It is used as an additive in vaccine manufacturing to inactivate toxins and pathogens.[49] Formaldehyde releasers are used as biocides in personal care products such as cosmetics. Although present at levels not normally considered harmful, they are known to cause allergic contact dermatitis in certain sensitised individuals.[50]

Aquarists use formaldehyde as a treatment for the parasites Ichthyophthirius multifiliis and Cryptocaryon irritans.[51] Formaldehyde is one of the main disinfectants recommended for destroying anthrax.[52]

Formaldehyde is also approved for use in the manufacture of animal feeds in the US. It is an antimicrobial agent used to maintain complete animal feeds or feed ingredients Salmonella negative for up to 21 days.[53]

Formaldehyde is commonly used to disinfect (via fumigating, sprinklers, and spray sleds) poultry and swine confinement buildings, egg hatcheries, rooms, railway cars, mushroom houses, tools, and equipment. Formaldehyde is a valuable packaged preservative in the food and beverage industry.[54][better source needed]

Tissue fixative and embalming agent edit

 
Injecting a giant squid specimen with formalin for preservation

Formaldehyde preserves or fixes tissue or cells. The process involves cross-linking of primary amino groups. The European Union has banned the use of formaldehyde as a biocide (including embalming) under the Biocidal Products Directive (98/8/EC) due to its carcinogenic properties.[55][56] Countries with a strong tradition of embalming corpses, such as Ireland and other colder-weather countries, have raised concerns. Despite reports to the contrary,[57] no decision on the inclusion of formaldehyde on Annex I of the Biocidal Products Directive for product-type 22 (embalming and taxidermist fluids) had been made as of September 2009.[58]

Formaldehyde-based crosslinking is exploited in ChIP-on-chip or ChIP-sequencing genomics experiments, where DNA-binding proteins are cross-linked to their cognate binding sites on the chromosome and analyzed to determine what genes are regulated by the proteins. Formaldehyde is also used as a denaturing agent in RNA gel electrophoresis, preventing RNA from forming secondary structures. A solution of 4% formaldehyde fixes pathology tissue specimens at about one mm per hour at room temperature.

Drug testing edit

Formaldehyde and an 18 M (concentrated) sulfuric acid makes Marquis reagent—which can identify alkaloids and other compounds.

Photography edit

In photography, formaldehyde is used in low concentrations for the process C-41 (color negative film) stabilizer in the final wash step,[59] as well as in the process E-6 pre-bleach step, to make it unnecessary in the final wash.

Safety edit

In view of its widespread use, toxicity, and volatility, formaldehyde poses a significant danger to human health.[60][61] In 2011, the US National Toxicology Program described formaldehyde as "known to be a human carcinogen".[62][63][64]

Chronic inhalation edit

However, concerns are associated with chronic (long-term) exposure by inhalation as may happen from thermal or chemical decomposition of formaldehyde-based resins and the production of formaldehyde resulting from the combustion of a variety of organic compounds (for example, exhaust gases). As formaldehyde resins are used in many construction materials, it is one of the more common indoor air pollutants.[65] At concentrations above 0.1 ppm in air, formaldehyde can irritate the eyes and mucous membranes.[66] Formaldehyde inhaled at this concentration may cause headaches, a burning sensation in the throat, and difficulty breathing, and can trigger or aggravate asthma symptoms.[67][68]

The CDC considers formaldehyde as a systemic poison. Formaldehyde poisoning can cause permanent changes in the nervous system's functions.[69]

A 1988 Canadian study of houses with urea-formaldehyde foam insulation found that formaldehyde levels as low as 0.046 ppm were positively correlated with eye and nasal irritation.[70] A 2009 review of studies has shown a strong association between exposure to formaldehyde and the development of childhood asthma.[71]

A theory was proposed for the carcinogenesis of formaldehyde in 1978.[72] In 1987 the United States Environmental Protection Agency (EPA) classified it as a probable human carcinogen, and after more studies the WHO International Agency for Research on Cancer (IARC) in 1995 also classified it as a probable human carcinogen. Further information and evaluation of all known data led the IARC to reclassify formaldehyde as a known human carcinogen[73] associated with nasal sinus cancer and nasopharyngeal cancer.[74] Studies in 2009 and 2010 have also shown a positive correlation between exposure to formaldehyde and the development of leukemia, particularly myeloid leukemia.[75][76] Nasopharyngeal and sinonasal cancers are relatively rare, with a combined annual incidence in the United States of < 4,000 cases.[77][78] About 30,000 cases of myeloid leukemia occur in the United States each year.[79][80] Some evidence suggests that workplace exposure to formaldehyde contributes to sinonasal cancers.[81] Professionals exposed to formaldehyde in their occupation, such as funeral industry workers and embalmers, showed an increased risk of leukemia and brain cancer compared with the general population.[82] Other factors are important in determining individual risk for the development of leukemia or nasopharyngeal cancer.[81][83][84] In yeast, formaldehyde is found to perturb pathways for DNA repair and cell cycle.[85]

In the residential environment, formaldehyde exposure comes from a number of routes; formaldehyde can be emitted by treated wood products, such as plywood or particle board, but it is produced by paints, varnishes, floor finishes, and cigarette smoking as well.[86] In July 2016, the U.S. EPA released a prepublication version of its final rule on Formaldehyde Emission Standards for Composite Wood Products.[87] These new rules impact manufacturers, importers, distributors, and retailers of products containing composite wood, including fiberboard, particleboard, and various laminated products, who must comply with more stringent record-keeping and labeling requirements.[88]

External media
 
Audio
  "Episode 202: Where Have All the FEMA Trailers Gone? Tracing Toxicity from Bust to Boom", Distillations, September 2, 2015, Science History Institute
Video
  Where Have All the Trailers Gone?, Video by Mariel Carr (Videographer) & Nick Shapiro (Researcher), 2015, Science History Institute

The U.S. EPA allows no more than 0.016 ppm formaldehyde in the air in new buildings constructed for that agency.[89][failed verification] A U.S. Environmental Protection Agency study found a new home measured 0.076 ppm when brand new and 0.045 ppm after 30 days.[90] The Federal Emergency Management Agency (FEMA) has also announced limits on the formaldehyde levels in trailers purchased by that agency.[91] The EPA recommends the use of "exterior-grade" pressed-wood products with phenol instead of urea resin to limit formaldehyde exposure, since pressed-wood products containing formaldehyde resins are often a significant source of formaldehyde in homes.[74]

The eyes are most sensitive to formaldehyde exposure: The lowest level at which many people can begin to smell formaldehyde ranges between 0.05 and 1 ppm. The maximum concentration value at the workplace is 0.3 ppm.[92][need quotation to verify] In controlled chamber studies, individuals begin to sense eye irritation at about 0.5 ppm; 5 to 20 percent report eye irritation at 0.5 to 1 ppm; and greater certainty for sensory irritation occurred at 1 ppm and above. While some agencies have used a level as low as 0.1 ppm as a threshold for irritation, the expert panel found that a level of 0.3 ppm would protect against nearly all irritation. In fact, the expert panel found that a level of 1.0 ppm would avoid eye irritation—the most sensitive endpoint—in 75–95% of all people exposed.[93]

 
Some air purifiers include filtering technology that is supposed to lower indoor formaldehyde concentration.

Formaldehyde levels in building environments are affected by a number of factors. These include the potency of formaldehyde-emitting products present, the ratio of the surface area of emitting materials to volume of space, environmental factors, product age, interactions with other materials, and ventilation conditions. Formaldehyde emits from a variety of construction materials, furnishings, and consumer products. The three products that emit the highest concentrations are medium density fiberboard, hardwood plywood, and particle board. Environmental factors such as temperature and relative humidity can elevate levels because formaldehyde has a high vapor pressure. Formaldehyde levels from building materials are the highest when a building first opens because materials would have less time to off-gas. Formaldehyde levels decrease over time as the sources suppress.

In operating rooms, formaldehyde is produced as a byproduct of electrosurgery and is present in surgical smoke, exposing surgeons and healthcare workers to potentially unsafe concentrations.[94]

Formaldehyde levels in air can be sampled and tested in several ways, including impinger, treated sorbent, and passive monitors.[95] The National Institute for Occupational Safety and Health (NIOSH) has measurement methods numbered 2016, 2541, 3500, and 3800.[96]

In June 2011, the twelfth edition of the National Toxicology Program (NTP) Report on Carcinogens (RoC) changed the listing status of formaldehyde from "reasonably anticipated to be a human carcinogen" to "known to be a human carcinogen."[62][63][64] Concurrently, a National Academy of Sciences (NAS) committee was convened and issued an independent review of the draft U.S. EPA IRIS assessment of formaldehyde, providing a comprehensive health effects assessment and quantitative estimates of human risks of adverse effects.[97]

Acute irritation and allergic reaction edit

 
Patch test

For most people, irritation from formaldehyde is temporary and reversible, although formaldehyde can cause allergies and is part of the standard patch test series. In 2005–06, it was the seventh-most-prevalent allergen in patch tests (9.0%).[98] People with formaldehyde allergy are advised to avoid formaldehyde releasers as well (e.g., Quaternium-15, imidazolidinyl urea, and diazolidinyl urea).[99] People who suffer allergic reactions to formaldehyde tend to display lesions on the skin in the areas that have had direct contact with the substance, such as the neck or thighs (often due to formaldehyde released from permanent press finished clothing) or dermatitis on the face (typically from cosmetics).[50] Formaldehyde has been banned in cosmetics in both Sweden[citation needed] and Japan.[100]

Other routes edit

Formaldehyde occurs naturally, and is "an essential intermediate in cellular metabolism in mammals and humans."[39] According to the American Chemistry Council, "Formaldehyde is found in every living system—from plants to animals to humans. It metabolizes quickly in the body, breaks down rapidly, is not persistent and does not accumulate in the body."[101]

The twelfth edition of NTP Report on Carcinogens notes that "food and water contain measureable concentrations of formaldehyde, but the significance of ingestion as a source of formaldehyde exposure for the general population is questionable." Food formaldehyde generally occurs in a bound form and formaldehyde is unstable in an aqueous solution.[64]

In humans, ingestion of as little as 30 millilitres (1.0 US fl oz) of 37% formaldehyde solution can cause death. Other symptoms associated with ingesting such a solution include gastrointestinal damage (vomiting, abdominal pain), and systematic damage (dizziness).[69] Testing for formaldehyde is by blood and/or urine by gas chromatography–mass spectrometry. Other methods include infrared detection, gas detector tubes, etc., of which high-performance liquid chromatography is the most sensitive.[102]

Regulation edit

Several web articles[like whom?] claim that formaldehyde has been banned from manufacture or import into the European Union (EU) under REACH (Registration, Evaluation, Authorization, and restriction of Chemical substances) legislation. That is a misconception, as formaldehyde is not listed in the Annex I of Regulation (EC) No 689/2008 (export and import of dangerous chemicals regulation), nor on a priority list for risk assessment. However, formaldehyde is banned from use in certain applications (preservatives for liquid-cooling and processing systems, slimicides, metalworking-fluid preservatives, and antifouling products) under the Biocidal Products Directive.[103][104] In the EU, the maximum allowed concentration of formaldehyde in finished products is 0.2%, and any product that exceeds 0.05% has to include a warning that the product contains formaldehyde.[50]

In the United States, Congress passed a bill July 7, 2010, regarding the use of formaldehyde in hardwood plywood, particle board, and medium density fiberboard. The bill limited the allowable amount of formaldehyde emissions from these wood products to 0.09 ppm, and required companies to meet this standard by January 2013.[105] The final U.S. EPA rule specified maximum emissions of "0.05 ppm formaldehyde for hardwood plywood, 0.09 ppm formaldehyde for particleboard, 0.11 ppm formaldehyde for medium-density fiberboard, and 0.13 ppm formaldehyde for thin medium-density fiberboard."[106]

Formaldehyde was declared a toxic substance by the 1999 Canadian Environmental Protection Act.[107]

The FDA is proposing a ban on hair relaxers with formaldehyde due to cancer concerns.[108]

Contaminant in food edit

Scandals have broken in both the 2005 Indonesia food scare and 2007 Vietnam food scare regarding the addition of formaldehyde to foods to extend shelf life. In 2011, after a four-year absence, Indonesian authorities found foods with formaldehyde being sold in markets in a number of regions across the country.[109] In August 2011, at least at two Carrefour supermarkets, the Central Jakarta Livestock and Fishery Sub-Department found cendol containing 10 parts per million of formaldehyde.[110] In 2014, the owner of two noodle factories in Bogor, Indonesia, was arrested for using formaldehyde in noodles. 50 kg of formaldehyde was confiscated.[111] Foods known to be contaminated included noodles, salted fish, and tofu. Chicken and beer were also rumored to be contaminated. In some places, such as China, manufacturers still use formaldehyde illegally as a preservative in foods, which exposes people to formaldehyde ingestion.[112] In the early 1900s, it was frequently added by US milk plants to milk bottles as a method of pasteurization due to the lack of knowledge and concern[113] regarding formaldehyde's toxicity.[114][115]

In 2011 in Nakhon Ratchasima, Thailand, truckloads of rotten chicken were treated with formaldehyde for sale in which "a large network", including 11 slaughterhouses run by a criminal gang, were implicated.[116] In 2012, 1 billion rupiah (almost US$100,000) of fish imported from Pakistan to Batam, Indonesia, were found laced with formaldehyde.[117]

Formalin contamination of foods has been reported in Bangladesh, with stores and supermarkets selling fruits, fishes, and vegetables that have been treated with formalin to keep them fresh.[118] However, in 2015, a Formalin Control Bill was passed in the Parliament of Bangladesh with a provision of life-term imprisonment as the maximum punishment as well as a maximum fine of 2,000,000 BDT but not less than 500,000 BDT for importing, producing, or hoarding formalin without a license.[119]

Formaldehyde was one of the chemicals used in 19th century industrialised food production that was investigated by Dr. Harvey W. Wiley with his famous 'Poison Squad' as part of the US Department of Agriculture. This led to the 1906 Pure Food and Drug Act, a landmark event in the early history of food regulation in the United States.

See also edit

References edit

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Notes edit

  1. ^ Formaldehyde is classified as a carcinogen, according to the Environmental Protection Agency, International Agency for Research on Cancer (IARC), and U.S. National Toxicology Program.[15]

External links edit

 
Wikisource has the text of the 1911 Encyclopædia Britannica article "Formalin".

February 15, 2024
formaldehyde, methanal, redirects, here, confused, with, methanol, menthol, other, uses, disambiguation, ɔːr, hide, also, fər, systematic, name, methanal, organic, compound, with, formula, ch2o, structure, compound, pungent, colourless, that, polymerises, spon. Methanal redirects here Not to be confused with Methanol or Menthol For other uses see Formaldehyde disambiguation Formaldehyde f ɔːr ˈ m ae l d ɪ h aɪ d for MAL di hide US also f e r fer systematic name methanal is an organic compound with the formula CH2O and structure H CHO The compound is a pungent colourless gas that polymerises spontaneously into paraformaldehyde It is stored as aqueous solutions formalin which consists mainly of the hydrate CH2 OH 2 It is the simplest of the aldehydes R CHO As a precursor to many other materials and chemical compounds in 2006 the global production of formaldehyde was estimated at 12 million tons per year 14 It is mainly used in the production of industrial resins e g for particle board and coatings Small amounts also occur naturally Formaldehyde Structural formula of formaldehyde with hydrogens Spacefill model of formaldehydeNamesPreferred IUPAC name Formaldehyde 1 Systematic IUPAC name Methanal 1 Other names Methyl aldehydeMethylene glycol diol forms in aqueous solution Methylene oxideFormalin aqueous solution FormolCarbonyl hydrideMethanoneOxomethaneIdentifiersCAS Number 50 00 0 Y3D model JSmol Interactive image3DMet B00018Beilstein Reference 1209228ChEBI CHEBI 16842 YChEMBL ChEMBL1255 YChemSpider 692 YDrugBank DB03843 YECHA InfoCard 100 000 002EC Number 200 001 8E number E240 preservatives Gmelin Reference 445IUPHAR BPS 4196KEGG D00017 YMeSH FormaldehydePubChem CID 712RTECS number LP8925000UNII 1HG84L3525 YUN number 2209CompTox Dashboard EPA DTXSID7020637InChI InChI 1S CH2O c1 2 h1H2 YKey WSFSSNUMVMOOMR UHFFFAOYSA N YInChI 1 CH2O c1 2 h1H2Key WSFSSNUMVMOOMR UHFFFAOYATSMILES C OProperties 7 Chemical formula C H 2OMolar mass 30 026 g mol 1Appearance Colorless gasDensity 0 8153 g cm3 20 C 2 liquid Melting point 92 C 134 F 181 K Boiling point 19 C 2 F 254 K 2 Solubility in water 400 g Llog P 0 350Vapor pressure gt 1 atm 3 Acidity pKa 13 27 hydrate 4 5 Magnetic susceptibility x 18 6 10 6 cm3 molDipole moment 2 330 D 6 StructurePoint group C2vMolecular shape Trigonal planarThermochemistry 8 Heat capacity C 35 387 J mol 1 K 1Std molarentropy S 298 218 760 J mol 1 K 1Std enthalpy offormation DfH 298 108 700 kJ mol 1Gibbs free energy DfG 102 667 kJ mol 1Std enthalpy ofcombustion DcH 298 571 kJ mol 1PharmacologyATCvet code QP53AX19 WHO HazardsGHS labelling Pictograms 9 Signal word DangerHazard statements H301 H311 H314 H317 H331 H335 H341 H350 H370 9 Precautionary statements P201 P280 P303 P361 P353 P304 P340 P310 P305 P351 P338 P308 P310 9 NFPA 704 fire diamond 440CORFlash point 64 C 147 F 337 K Autoignitiontemperature 430 C 806 F 703 K Explosive limits 7 73 Lethal dose or concentration LD LC LD50 median dose 100 mg kg oral rat 12 LC50 median concentration 333 ppm mouse 2 h 815 ppm rat 30 min 13 LCLo lowest published 333 ppm cat 2 h 13 NIOSH US health exposure limits PEL Permissible TWA 0 75 ppm ST 2 ppm as formaldehyde and formalin 10 11 REL Recommended Ca TWA 0 016 ppm C 0 1 ppm 15 minute 10 IDLH Immediate danger Ca 20 ppm 10 Safety data sheet SDS MSDS Archived Related compoundsRelated aldehydes AcetaldehydeButyraldehydeDecanalHeptanalHexanalNonanalOctadecanalOctanalPentanalPropionaldehydeRelated compounds MethanolFormic acidExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Formaldehyde is classified as a carcinogen note 1 and can cause respiratory and skin irritation upon exposure 15 Contents 1 Forms 1 1 Structure and bonding 2 Occurrence 2 1 Interstellar formaldehyde 3 Synthesis and industrial production 3 1 Laboratory synthesis 3 2 Industry 4 Biochemistry 5 Organic chemistry 5 1 Polymerization and hydration 5 2 Oxidation and reduction 5 3 Hydroxymethylation and chloromethylation 5 4 Other reactions 6 Uses 6 1 Industrial applications 6 2 Niche uses 6 2 1 Disinfectant and biocide 6 2 2 Tissue fixative and embalming agent 6 2 3 Drug testing 6 3 Photography 7 Safety 7 1 Chronic inhalation 7 2 Acute irritation and allergic reaction 7 3 Other routes 8 Regulation 9 Contaminant in food 10 See also 11 References 12 Notes 13 External linksForms editFormaldehyde is more complicated than many simple carbon compounds in that it adopts several diverse forms These compounds can often be used interchangeably and can be interconverted Molecular formaldehyde A colorless gas with a characteristic pungent irritating odor It is stable at about 150 C but polymerizes when condensed to a liquid 1 3 5 Trioxane with the formula CH2O 3 It is a white solid that dissolves without degradation in organic solvents It is a trimer of molecular formaldehyde Paraformaldehyde with the formula HO CH2O nH It is a white solid that is insoluble in most solvents Methanediol with the formula CH2 OH 2 This compound also exists in equilibrium with various oligomers short polymers depending on the concentration and temperature A saturated water solution of about 40 formaldehyde by volume or 37 by mass is called 100 formalin A small amount of stabilizer such as methanol is usually added to suppress oxidation and polymerization A typical commercial grade formalin may contain 10 12 methanol in addition to various metallic impurities Formaldehyde was first used as a generic trademark in 1893 following a previous trade name formalin 16 Main forms of formaldehyde nbsp Monomeric formaldehyde subject of this article nbsp Trioxane is a stable cyclic trimer of formaldehyde nbsp Paraformaldehyde is a common form of formaldehyde for industrial applications nbsp Methanediol the predominant species in dilute aqueous solutions of formaldehydeStructure and bonding edit Molecular formaldehyde contains a central carbon atom with a double bond to the oxygen atom and a single bond to each hydrogen atom This structure is summarised by the condensed formula H2C O 17 The molecule is planar Y shaped and its molecular symmetry belongs to the C2v point group 18 The precise molecular geometry of gaseous formaldehyde has been determined by gas electron diffraction 17 19 and microwave spectroscopy 20 21 The bond lengths are 1 21 A for the carbon oxygen bond 17 19 20 21 22 and around 1 11 A for the carbon hydrogen bond 17 19 20 21 while the H C H bond angle is 117 20 21 close to the 120 angle found in an ideal trigonal planar molecule 17 Some excited electronic states of formaldehyde are pyramidal rather than planar as in the ground state 22 Occurrence editProcesses in the upper atmosphere contribute up to 90 of the total formaldehyde in the environment Formaldehyde is an intermediate in the oxidation or combustion of methane as well as of other carbon compounds e g in forest fires automobile exhaust and tobacco smoke When produced in the atmosphere by the action of sunlight and oxygen on atmospheric methane and other hydrocarbons it becomes part of smog Formaldehyde has also been detected in outer space Formaldehyde and its adducts are ubiquitous in nature Food may contain formaldehyde at levels 1 100 mg kg 23 Formaldehyde formed in the metabolism of the amino acids serine and threonine is found in the bloodstream of humans and other primates at concentrations of approximately 50 micromolar 24 Experiments in which animals are exposed to an atmosphere containing isotopically labeled formaldehyde have demonstrated that even in deliberately exposed animals the majority of formaldehyde DNA adducts found in non respiratory tissues are derived from endogenously produced formaldehyde 25 Formaldehyde does not accumulate in the environment because it is broken down within a few hours by sunlight or by bacteria present in soil or water Humans metabolize formaldehyde quickly converting it to formic acid so it does not accumulate 26 27 It nonetheless presents significant health concerns as a contaminant Interstellar formaldehyde edit Main article Interstellar formaldehyde Formaldehyde appears to be a useful probe in astrochemistry due to prominence of the 110 111 and 211 212 K doublet transitions It was the first polyatomic organic molecule detected in the interstellar medium 28 Since its initial detection in 1969 it has been observed in many regions of the galaxy Because of the widespread interest in interstellar formaldehyde it has been extensively studied yielding new extragalactic sources 29 A proposed mechanism for the formation is the hydrogenation of CO ice 30 H CO HCO HCO H CH2OHCN HNC H2CO and dust have also been observed inside the comae of comets C 2012 F6 Lemmon and C 2012 S1 ISON 31 32 Synthesis and industrial production editLaboratory synthesis edit Formaldehyde was first reported in 1859 by the Russian chemist Aleksandr Butlerov 1828 1886 33 In his paper Butlerov referred to formaldehyde as dioxymethylen methylene dioxide page 247 because his empirical formula for it was incorrect C4H4O4 It was conclusively identified by August Wilhelm von Hofmann who first announced the production of formaldehyde by passing methanol vapor in air over hot platinum wire 34 35 With modifications Hoffmann s method remains the basis of the present day industrial route Solution routes to formaldehyde also entail oxidation of methanol or methyl iodide 36 Industry edit Formaldehyde is produced industrially by the catalytic oxidation of methanol The most common catalysts are silver metal iron III oxide 37 iron molybdenum oxides e g iron III molybdate with a molybdenum enriched surface 38 or vanadium oxides In the commonly used formox process methanol and oxygen react at c 250 400 C in presence of iron oxide in combination with molybdenum and or vanadium to produce formaldehyde according to the chemical equation 39 2 CH3OH O2 2 CH2O 2 H2OThe silver based catalyst usually operates at a higher temperature about 650 C Two chemical reactions on it simultaneously produce formaldehyde that shown above and the dehydrogenation reaction CH3OH CH2O H2In principle formaldehyde could be generated by oxidation of methane but this route is not industrially viable because the methanol is more easily oxidized than methane 39 Biochemistry editFormaldehyde is produced via several enzyme catalyzed routes 40 Living beings including humans produce formaldehyde as part of their metabolism Formaldehyde are key to several bodily functions e g epigenetics 24 but its amount must also be tightly controlled to avoid self poisioning 41 Serine hydroxymethyltransferase can decompose serine into formaldehyde and glycine according to this reaction HOCH2CH NH2 CO2H CH2O H2C NH2 CO2H methylotrophic microbes convert methanol into formaldehyde and energy via methanol dehydrogenase CH3OH CH2O 2e 2H Other routes to formaldehyde include oxidative demethylations semicarbazide sensitive amine oxidases dimethylglycine dehydrogenases lipid peroxidases P450 oxidases and N methyl group demethylases 40 Formaldehyde is catabolized by alcohol dehydrogenase ADH5 and aldehyde dehydrogenase ALDH2 42 Organic chemistry editFormaldehyde is a building block in the synthesis of many other compounds of specialised and industrial significance It exhibits most of the chemical properties of other aldehydes but is more reactive Polymerization and hydration edit Gaseous formaldehyde polymerizes on the active sites of the vessel walls but the mechanism of the reaction is unknown 43 Small amounts of hydrogen chloride or boron trifluoride or stannic chloride present in gaseous formaldehyde provide the catalytic effect and make the polymerization rapid 44 Monomeric CH2O is a gas and is rarely encountered in the laboratory Formaldehyde in aqueous solutions unlike some other small aldehydes which need specific conditions to oligomerize through aldol condensation oligomerizes spontaneously at a common state The trimer is 1 3 5 trioxane CH2O 3 is typical oligomer Many cyclic oligomers of other sizes have been isolated Similarly formaldehyde hydrates to give the geminal diol methanediol which condenses further to form hydroxy terminated oligomers HO CH2O nH The polymer is called paraformaldehyde The higher concentration of formaldehyde the more equilibrium shifts towards polymerization Diluting with water or increasing the solution temperature as well as adding alcohols such as methanol or ethanol lowers that tendency Oxidation and reduction edit It is readily oxidized by atmospheric oxygen into formic acid For this reason commercial formaldehyde is typically contaminated with formic acid Formaldehyde can be hydrogenated into methanol In the Cannizzaro reaction formaldehyde and base react to produce formic acid and methanol a disproportionation reaction Hydroxymethylation and chloromethylation edit Formaldehyde reacts with many compounds resulting in hydroxymethylation X H CH2O X CH2OH X R2N RC O NR SH The resulting hydroxymethyl derivatives typically react further Thus amines give hexahydro 1 3 5 triazines 3 RNH2 3 CH2O RNCH2 3 3 H2OSimilarly when combined with hydrogen sulfide it forms trithiane 45 3 CH2O 3 H2S CH2S 3 3 H2OIn the presence of acids it participates in electrophilic aromatic substitution reactions with aromatic compounds resulting in hydroxymethylated derivatives ArH CH2O ArCH2OHWhen conducted in the presence of hydrogen chloride the product is the chloromethyl compound as described in the Blanc chloromethylation If the arene is electron rich as in phenols elaborate condensations ensue With 4 substituted phenols one obtains calixarenes 46 Phenol results in polymers Other reactions edit Many amino acids react with formaldehyde 40 Cysteine converts to thioproline Uses editIndustrial applications edit Formaldehyde is a common precursor to more complex compounds and materials In approximate order of decreasing consumption products generated from formaldehyde include urea formaldehyde resin melamine resin phenol formaldehyde resin polyoxymethylene plastics 1 4 butanediol and methylene diphenyl diisocyanate 39 The textile industry uses formaldehyde based resins as finishers to make fabrics crease resistant 47 nbsp Two steps in formation of urea formaldehyde resin which is widely used in the production of particle boardWhen treated with phenol urea or melamine formaldehyde produces respectively hard thermoset phenol formaldehyde resin urea formaldehyde resin and melamine resin These polymers are permanent adhesives used in plywood and carpeting They are also foamed to make insulation or cast into moulded products Production of formaldehyde resins accounts for more than half of formaldehyde consumption Formaldehyde is also a precursor to polyfunctional alcohols such as pentaerythritol which is used to make paints and explosives Other formaldehyde derivatives include methylene diphenyl diisocyanate an important component in polyurethane paints and foams and hexamine which is used in phenol formaldehyde resins as well as the explosive RDX nbsp Condensation with acetaldehyde affords pentaerythritol a chemical necessary in synthesizing PETN a high explosive 48 Condensation with phenols gives phenol formaldehyde resins Niche uses edit Disinfectant and biocide edit An aqueous solution of formaldehyde can be useful as a disinfectant as it kills most bacteria and fungi including their spores It is used as an additive in vaccine manufacturing to inactivate toxins and pathogens 49 Formaldehyde releasers are used as biocides in personal care products such as cosmetics Although present at levels not normally considered harmful they are known to cause allergic contact dermatitis in certain sensitised individuals 50 Aquarists use formaldehyde as a treatment for the parasites Ichthyophthirius multifiliis and Cryptocaryon irritans 51 Formaldehyde is one of the main disinfectants recommended for destroying anthrax 52 Formaldehyde is also approved for use in the manufacture of animal feeds in the US It is an antimicrobial agent used to maintain complete animal feeds or feed ingredients Salmonella negative for up to 21 days 53 Formaldehyde is commonly used to disinfect via fumigating sprinklers and spray sleds poultry and swine confinement buildings egg hatcheries rooms railway cars mushroom houses tools and equipment Formaldehyde is a valuable packaged preservative in the food and beverage industry 54 better source needed Tissue fixative and embalming agent edit nbsp Injecting a giant squid specimen with formalin for preservationFormaldehyde preserves or fixes tissue or cells The process involves cross linking of primary amino groups The European Union has banned the use of formaldehyde as a biocide including embalming under the Biocidal Products Directive 98 8 EC due to its carcinogenic properties 55 56 Countries with a strong tradition of embalming corpses such as Ireland and other colder weather countries have raised concerns Despite reports to the contrary 57 no decision on the inclusion of formaldehyde on Annex I of the Biocidal Products Directive for product type 22 embalming and taxidermist fluids had been made as of September 2009 update 58 Formaldehyde based crosslinking is exploited in ChIP on chip or ChIP sequencing genomics experiments where DNA binding proteins are cross linked to their cognate binding sites on the chromosome and analyzed to determine what genes are regulated by the proteins Formaldehyde is also used as a denaturing agent in RNA gel electrophoresis preventing RNA from forming secondary structures A solution of 4 formaldehyde fixes pathology tissue specimens at about one mm per hour at room temperature Drug testing edit Formaldehyde and an 18 M concentrated sulfuric acid makes Marquis reagent which can identify alkaloids and other compounds Photography edit In photography formaldehyde is used in low concentrations for the process C 41 color negative film stabilizer in the final wash step 59 as well as in the process E 6 pre bleach step to make it unnecessary in the final wash Safety editIn view of its widespread use toxicity and volatility formaldehyde poses a significant danger to human health 60 61 In 2011 the US National Toxicology Program described formaldehyde as known to be a human carcinogen 62 63 64 Chronic inhalation edit This section may require cleanup to meet Wikipedia s quality standards The specific problem is A little too scattered among different types of risks Needs some reorganization Please help improve this section if you can November 2023 Learn how and when to remove this template message However concerns are associated with chronic long term exposure by inhalation as may happen from thermal or chemical decomposition of formaldehyde based resins and the production of formaldehyde resulting from the combustion of a variety of organic compounds for example exhaust gases As formaldehyde resins are used in many construction materials it is one of the more common indoor air pollutants 65 At concentrations above 0 1 ppm in air formaldehyde can irritate the eyes and mucous membranes 66 Formaldehyde inhaled at this concentration may cause headaches a burning sensation in the throat and difficulty breathing and can trigger or aggravate asthma symptoms 67 68 The CDC considers formaldehyde as a systemic poison Formaldehyde poisoning can cause permanent changes in the nervous system s functions 69 A 1988 Canadian study of houses with urea formaldehyde foam insulation found that formaldehyde levels as low as 0 046 ppm were positively correlated with eye and nasal irritation 70 A 2009 review of studies has shown a strong association between exposure to formaldehyde and the development of childhood asthma 71 A theory was proposed for the carcinogenesis of formaldehyde in 1978 72 In 1987 the United States Environmental Protection Agency EPA classified it as a probable human carcinogen and after more studies the WHO International Agency for Research on Cancer IARC in 1995 also classified it as a probable human carcinogen Further information and evaluation of all known data led the IARC to reclassify formaldehyde as a known human carcinogen 73 associated with nasal sinus cancer and nasopharyngeal cancer 74 Studies in 2009 and 2010 have also shown a positive correlation between exposure to formaldehyde and the development of leukemia particularly myeloid leukemia 75 76 Nasopharyngeal and sinonasal cancers are relatively rare with a combined annual incidence in the United States of lt 4 000 cases 77 78 About 30 000 cases of myeloid leukemia occur in the United States each year 79 80 Some evidence suggests that workplace exposure to formaldehyde contributes to sinonasal cancers 81 Professionals exposed to formaldehyde in their occupation such as funeral industry workers and embalmers showed an increased risk of leukemia and brain cancer compared with the general population 82 Other factors are important in determining individual risk for the development of leukemia or nasopharyngeal cancer 81 83 84 In yeast formaldehyde is found to perturb pathways for DNA repair and cell cycle 85 In the residential environment formaldehyde exposure comes from a number of routes formaldehyde can be emitted by treated wood products such as plywood or particle board but it is produced by paints varnishes floor finishes and cigarette smoking as well 86 In July 2016 the U S EPA released a prepublication version of its final rule on Formaldehyde Emission Standards for Composite Wood Products 87 These new rules impact manufacturers importers distributors and retailers of products containing composite wood including fiberboard particleboard and various laminated products who must comply with more stringent record keeping and labeling requirements 88 External media nbsp Audio nbsp Episode 202 Where Have All the FEMA Trailers Gone Tracing Toxicity from Bust to Boom Distillations September 2 2015 Science History InstituteVideo nbsp Where Have All the Trailers Gone Video by Mariel Carr Videographer amp Nick Shapiro Researcher 2015 Science History InstituteThe U S EPA allows no more than 0 016 ppm formaldehyde in the air in new buildings constructed for that agency 89 failed verification A U S Environmental Protection Agency study found a new home measured 0 076 ppm when brand new and 0 045 ppm after 30 days 90 The Federal Emergency Management Agency FEMA has also announced limits on the formaldehyde levels in trailers purchased by that agency 91 The EPA recommends the use of exterior grade pressed wood products with phenol instead of urea resin to limit formaldehyde exposure since pressed wood products containing formaldehyde resins are often a significant source of formaldehyde in homes 74 The eyes are most sensitive to formaldehyde exposure The lowest level at which many people can begin to smell formaldehyde ranges between 0 05 and 1 ppm The maximum concentration value at the workplace is 0 3 ppm 92 need quotation to verify In controlled chamber studies individuals begin to sense eye irritation at about 0 5 ppm 5 to 20 percent report eye irritation at 0 5 to 1 ppm and greater certainty for sensory irritation occurred at 1 ppm and above While some agencies have used a level as low as 0 1 ppm as a threshold for irritation the expert panel found that a level of 0 3 ppm would protect against nearly all irritation In fact the expert panel found that a level of 1 0 ppm would avoid eye irritation the most sensitive endpoint in 75 95 of all people exposed 93 nbsp Some air purifiers include filtering technology that is supposed to lower indoor formaldehyde concentration Formaldehyde levels in building environments are affected by a number of factors These include the potency of formaldehyde emitting products present the ratio of the surface area of emitting materials to volume of space environmental factors product age interactions with other materials and ventilation conditions Formaldehyde emits from a variety of construction materials furnishings and consumer products The three products that emit the highest concentrations are medium density fiberboard hardwood plywood and particle board Environmental factors such as temperature and relative humidity can elevate levels because formaldehyde has a high vapor pressure Formaldehyde levels from building materials are the highest when a building first opens because materials would have less time to off gas Formaldehyde levels decrease over time as the sources suppress In operating rooms formaldehyde is produced as a byproduct of electrosurgery and is present in surgical smoke exposing surgeons and healthcare workers to potentially unsafe concentrations 94 Formaldehyde levels in air can be sampled and tested in several ways including impinger treated sorbent and passive monitors 95 The National Institute for Occupational Safety and Health NIOSH has measurement methods numbered 2016 2541 3500 and 3800 96 In June 2011 the twelfth edition of the National Toxicology Program NTP Report on Carcinogens RoC changed the listing status of formaldehyde from reasonably anticipated to be a human carcinogen to known to be a human carcinogen 62 63 64 Concurrently a National Academy of Sciences NAS committee was convened and issued an independent review of the draft U S EPA IRIS assessment of formaldehyde providing a comprehensive health effects assessment and quantitative estimates of human risks of adverse effects 97 Acute irritation and allergic reaction edit nbsp Patch testFor most people irritation from formaldehyde is temporary and reversible although formaldehyde can cause allergies and is part of the standard patch test series In 2005 06 it was the seventh most prevalent allergen in patch tests 9 0 98 People with formaldehyde allergy are advised to avoid formaldehyde releasers as well e g Quaternium 15 imidazolidinyl urea and diazolidinyl urea 99 People who suffer allergic reactions to formaldehyde tend to display lesions on the skin in the areas that have had direct contact with the substance such as the neck or thighs often due to formaldehyde released from permanent press finished clothing or dermatitis on the face typically from cosmetics 50 Formaldehyde has been banned in cosmetics in both Sweden citation needed and Japan 100 Other routes edit Formaldehyde occurs naturally and is an essential intermediate in cellular metabolism in mammals and humans 39 According to the American Chemistry Council Formaldehyde is found in every living system from plants to animals to humans It metabolizes quickly in the body breaks down rapidly is not persistent and does not accumulate in the body 101 The twelfth edition of NTP Report on Carcinogens notes that food and water contain measureable concentrations of formaldehyde but the significance of ingestion as a source of formaldehyde exposure for the general population is questionable Food formaldehyde generally occurs in a bound form and formaldehyde is unstable in an aqueous solution 64 In humans ingestion of as little as 30 millilitres 1 0 US fl oz of 37 formaldehyde solution can cause death Other symptoms associated with ingesting such a solution include gastrointestinal damage vomiting abdominal pain and systematic damage dizziness 69 Testing for formaldehyde is by blood and or urine by gas chromatography mass spectrometry Other methods include infrared detection gas detector tubes etc of which high performance liquid chromatography is the most sensitive 102 Regulation editSeveral web articles like whom claim that formaldehyde has been banned from manufacture or import into the European Union EU under REACH Registration Evaluation Authorization and restriction of Chemical substances legislation That is a misconception as formaldehyde is not listed in the Annex I of Regulation EC No 689 2008 export and import of dangerous chemicals regulation nor on a priority list for risk assessment However formaldehyde is banned from use in certain applications preservatives for liquid cooling and processing systems slimicides metalworking fluid preservatives and antifouling products under the Biocidal Products Directive 103 104 In the EU the maximum allowed concentration of formaldehyde in finished products is 0 2 and any product that exceeds 0 05 has to include a warning that the product contains formaldehyde 50 In the United States Congress passed a bill July 7 2010 regarding the use of formaldehyde in hardwood plywood particle board and medium density fiberboard The bill limited the allowable amount of formaldehyde emissions from these wood products to 0 09 ppm and required companies to meet this standard by January 2013 105 The final U S EPA rule specified maximum emissions of 0 05 ppm formaldehyde for hardwood plywood 0 09 ppm formaldehyde for particleboard 0 11 ppm formaldehyde for medium density fiberboard and 0 13 ppm formaldehyde for thin medium density fiberboard 106 Formaldehyde was declared a toxic substance by the 1999 Canadian Environmental Protection Act 107 The FDA is proposing a ban on hair relaxers with formaldehyde due to cancer concerns 108 Contaminant in food editScandals have broken in both the 2005 Indonesia food scare and 2007 Vietnam food scare regarding the addition of formaldehyde to foods to extend shelf life In 2011 after a four year absence Indonesian authorities found foods with formaldehyde being sold in markets in a number of regions across the country 109 In August 2011 at least at two Carrefour supermarkets the Central Jakarta Livestock and Fishery Sub Department found cendol containing 10 parts per million of formaldehyde 110 In 2014 the owner of two noodle factories in Bogor Indonesia was arrested for using formaldehyde in noodles 50 kg of formaldehyde was confiscated 111 Foods known to be contaminated included noodles salted fish and tofu Chicken and beer were also rumored to be contaminated In some places such as China manufacturers still use formaldehyde illegally as a preservative in foods which exposes people to formaldehyde ingestion 112 In the early 1900s it was frequently added by US milk plants to milk bottles as a method of pasteurization due to the lack of knowledge and concern 113 regarding formaldehyde s toxicity 114 115 In 2011 in Nakhon Ratchasima Thailand truckloads of rotten chicken were treated with formaldehyde for sale in which a large network including 11 slaughterhouses run by a criminal gang were implicated 116 In 2012 1 billion rupiah almost US 100 000 of fish imported from Pakistan to Batam Indonesia were found laced with formaldehyde 117 Formalin contamination of foods has been reported in Bangladesh with stores and supermarkets selling fruits fishes and vegetables that have been treated with formalin to keep them fresh 118 However in 2015 a Formalin Control Bill was passed in the Parliament of Bangladesh with a provision of life term imprisonment as the maximum punishment as well as a maximum fine of 2 000 000 BDT but not less than 500 000 BDT for importing producing or hoarding formalin without a license 119 Formaldehyde was one of the chemicals used in 19th century industrialised food production that was investigated by Dr Harvey W Wiley with his famous Poison Squad as part of the US Department of Agriculture This led to the 1906 Pure Food and Drug Act a landmark event in the early history of food regulation in the United States See also editTransition metal complexes of aldehydes and ketones includes several complexes of formaldehyde 1 3 Dioxetane DMDM hydantoin Sawdust Health impacts of sawdust Sulphobes Wood glue Wood preservativeReferences edit a b Front Matter Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 Blue Book Cambridge The Royal Society of Chemistry 2014 p 908 doi 10 1039 9781849733069 FP001 ISBN 978 0 85404 182 4 a b SIDS Initial Assessment Report PDF International Programme on Chemical Safety Archived from the original PDF on 2019 03 28 Retrieved 2019 04 21 Spence Robert Wild William 1935 114 The vapour pressure curve of formaldehyde and some related data Journal of the Chemical Society Resumed 506 509 doi 10 1039 jr9350000506 PubChem Compound Database CID 712 National Center for Biotechnology Information Archived from the original on 2019 04 12 Retrieved 2017 07 08 Acidity of aldehydes Chemistry Stack Exchange Archived from the original on 2018 09 01 Retrieved 2019 04 21 Nelson R D Jr Lide D R Maryott A A 1967 Selected Values of electric dipole moments for molecules in the gas phase NSRDS NBS10 PDF Archived PDF from the original on 2018 06 08 Retrieved 2019 04 21 Weast Robert C ed 1981 CRC Handbook of Chemistry and Physics 62nd ed Boca Raton FL CRC Press pp C 301 E 61 ISBN 0 8493 0462 8 CRC handbook of chemistry and physics a ready reference book of chemical and physical data William M Haynes David R Lide Thomas J Bruno 2016 2017 97th ed Boca Raton Florida 2016 ISBN 978 1 4987 5428 6 OCLC 930681942 Archived from the original on 2022 05 04 Retrieved 2022 04 12 a href Template Cite book html title Template Cite book cite book a CS1 maint location missing publisher link CS1 maint others link a b c Record of Formaldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health accessed on 13 March 2020 a b c NIOSH Pocket Guide to Chemical Hazards 0293 National Institute for Occupational Safety and Health NIOSH NIOSH Pocket Guide to Chemical Hazards 0294 National Institute for Occupational Safety and Health NIOSH Substance Name Formaldehyde USP ChemlDplus US National Library of Medicine Archived from the original on 2017 09 18 a b Formaldehyde Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH Humans IARC Working Group on the Evaluation of Carcinogenic Risks to 2006 Summary of Data Reported and Evaluation International Agency for Research on Cancer Archived from the original on 2024 02 02 Retrieved 2023 03 06 a b Formaldehyde and Cancer Risk 10 June 2011 Archived from the original on 2023 09 20 Retrieved 2023 09 21 Formalin Merriam Webster Inc 15 January 2020 archived from the original on 18 April 2020 retrieved 18 February 2020 a b c d e Wells A F 1984 Structural Inorganic Chemistry 5th ed Oxford University Press pp 915 917 926 ISBN 978 0 19 965763 6 Greenwood Norman N Earnshaw Alan 1997 Chemistry of the Elements 2nd ed Butterworth Heinemann p 1291 ISBN 978 0 08 037941 8 a b c Chuichi Kato Shigehiro Konaka Takao Iijima Masao Kimura 1969 Electron Diffraction Studies of Formaldehyde Acetaldehyde and Acetone Bull Chem Soc Jpn 42 8 2148 2158 doi 10 1246 bcsj 42 2148 a b c d William M Haynes ed 2012 CRC Handbook of Chemistry and Physics 93rd ed CRC Press pp 9 39 ISBN 978 1439880500 a b c d Duncan J L 1974 The ground state average and equilibrium structures of formaldehyde and ethylene Mol Phys 28 5 1177 1191 Bibcode 1974MolPh 28 1177D doi 10 1080 00268977400102501 a b Smith Michael B March Jerry 2007 March s Advanced Organic Chemistry 6th ed John Wiley amp Sons pp 24 25 335 ISBN 978 0 471 72091 1 Chapter 5 8 Formaldehyde PDF Air Quality Guidelines 2nd ed Copenhagen Denmark WHO Regional Office for Europe 2001 Archived PDF from the original on 2023 02 18 Retrieved 2023 02 18 a b Pham Vanha N Bruemmer Kevin J Toh Joel D W Ge Eva J Tenney Logan Ward Carl C Dingler Felix A Millington Christopher L Garcia Prieto Carlos A Pulos Holmes Mia C Ingolia Nicholas T Pontel Lucas B Esteller Manel Patel Ketan J Nomura Daniel K Chang Christopher J 2023 Formaldehyde regulates S adenosylmethionine biosynthesis and one carbon metabolism Science 382 6670 eabp9201 doi 10 1126 science abp9201 PMID 37917677 S2CID 264935787 Swenberg J A Lu K Moeller B C Gao L Upton P B Nakamura J Starr T B 2011 Endogenous versus Exogenous DNA Adducts Their Role in Carcinogenesis Epidemiology and Risk Assessment Toxicological Sciences 120 Suppl 1 S130 S145 doi 10 1093 toxsci kfq371 PMC 3043087 PMID 21163908 Formaldehyde Is Biodegradable Quickly Broken Down in the Air By Sunlight or By Bacteria in Soil or Water Press release Formaldehyde Panel of the American Chemistry Council 2014 01 29 Archived from the original on 2019 03 28 Retrieved 2017 04 22 PDF 2019 03 28 https web archive org web 20190328010414 https www atsdr cdc gov ToxProfiles tp111 pdf Archived from the original PDF on 2019 03 28 Retrieved 2023 02 18 a href Template Cite web html title Template Cite web cite web a Missing or empty title help Zuckerman B Buhl D Palmer P Snyder L E 1970 Observation of interstellar formaldehyde Astrophys J 160 485 506 Bibcode 1970ApJ 160 485Z doi 10 1086 150449 Mangum Jeffrey G Darling Jeremy Menten Karl M Henkel Christian 2008 Formaldehyde Densitometry of Starburst Galaxies Astrophys J 673 2 832 46 arXiv 0710 2115 Bibcode 2008ApJ 673 832M doi 10 1086 524354 S2CID 14035123 Woon David E 2002 Modeling Gas Grain Chemistry with Quantum Chemical Cluster Calculations I Heterogeneous Hydrogenation of CO and H2CO on Icy Grain Mantles Astrophys J 569 1 541 48 Bibcode 2002ApJ 569 541W doi 10 1086 339279 Zubritsky Elizabeth Neal Jones Nancy 11 August 2014 RELEASE 14 038 NASA s 3 D Study of Comets Reveals Chemical Factory at Work NASA Archived from the original on 12 August 2014 Retrieved 12 August 2014 Cordiner M A et al 11 August 2014 Mapping the Release of Volatiles in the Inner Comae of Comets C 2012 F6 Lemmon and C 2012 S1 ISON Using the Atacama Large Millimeter Submillimeter Array The Astrophysical Journal 792 1 L2 arXiv 1408 2458 Bibcode 2014ApJ 792L 2C doi 10 1088 2041 8205 792 1 L2 S2CID 26277035 Butlerow A 1859 Ueber einige Derivate des Jodmethylens On some derivatives of methylene iodide Vol 111 pp 242 252 Archived from the original on 2023 01 12 Retrieved 2015 06 27 a href Template Cite book html title Template Cite book cite book a work ignored help See A W Hofmann 14 October 1867 Zur Kenntnis des Methylaldehyds Contributions to our knowledge of methylaldehyde Monatsbericht der Koniglich Preussischen Akademie der Wissenschaften zu Berlin Monthly Report of the Royal Prussian Academy of Sciences in Berlin vol 8 pages 665 669 Reprinted in A W Hofmann 1868 Zur Kenntnis des Methylaldehyds Annalen der Chemie und Pharmacie Annals of Chemistry and Pharmacy vol 145 no 3 pages 357 361 A W Hofmann 1868 Zur Kenntnis des Methylaldehyds Journal fur praktische Chemie Journal for Practical Chemistry vol 103 no 1 pages 246 250 However it was not until 1869 that Hofmann determined the correct empirical formula of formaldehyde See A W Hofmann 5 April 1869 Beitrage zur Kenntnis des Methylaldehyds Monatsbericht der Koniglich Preussischen Akademie der Wissenschaften zu Berlin vol pages 362 372 Reprinted in Hofmann A W 1869 Beitrage zur Kenntnis des Methylaldehyds Journal fur Praktische Chemie 107 1 414 424 doi 10 1002 prac 18691070161 A W Hofmann 1869 Beitrage zur Kenntnis des Methylaldehyds Berichte der Deutschen Chemischen Gesellschaft Reports of the German Chemical Society vol 2 pages 152 159 Read J 1935 Text Book of Organic Chemistry London G Bell amp Sons Hooker Jacob M Schonberger Matthias Schieferstein Hanno Fowler Joanna S 2008 A Simple Rapid Method for the Preparation of 11C Formaldehyde Angewandte Chemie 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authors list link Was Death in the Milk The Indianapolis News 1900 07 31 p 5 Archived from the original on 2018 11 17 Retrieved 2014 08 20 via Newspapers com nbsp Wants New Law Enacted Food Inspector Farnsworth Would Have Use of Formaldehyde in Milk Stopped The Topeka Daily Capital 1903 08 30 p 8 Archived from the original on 2018 11 17 Retrieved 2014 08 20 via Newspapers com nbsp Illegal business being run by a gang The Nation 2011 06 16 Archived from the original on 2011 06 16 Import of formaldehyde fish from Pakistan foiled in Batam The Jakarta Post 2012 02 23 Archived from the original on 2018 12 16 Trader Fined for Selling Fish Treated with Formalin The Daily Star 2009 08 31 Archived from the original on 2019 04 29 Formalin Control Bill 2015 passed ntv online 2015 02 16 Archived from the original on 2018 03 23 Retrieved 2015 03 04 Notes edit Formaldehyde is classified as a carcinogen according to the Environmental Protection Agency International Agency for Research on Cancer IARC and U S National Toxicology Program 15 External links edit nbsp Wikisource has the text of the 1911 Encyclopaedia Britannica article Formalin International Chemical Safety Card 0275 gas International Chemical Safety Card 0695 solution NIOSH Pocket Guide to Chemical Hazards 0293 National Institute for Occupational Safety and Health NIOSH Entry for Formaldehyde on the Australian National Pollutant Inventory Formaldehyde from ChemSub Online Prevention guide Formaldehyde in the Workplace PDF from the IRSST Formaldehyde from the National Institute for Occupational Safety and Health IPCS Health and Safety Guide 57 Formaldehyde IPCS Environmental Health Criteria 89 Formaldehyde SIDS Initial Assessment Report for Formaldehyde from the Organisation for Economic Co operation and Development OECD Formaldehyde Added to Known Carcinogens List Despite Lobbying by Chemical Industry video report by Democracy Now Do you own a post Katrina FEMA trailer Check your VIN So you re living in one of FEMA s Katrina trailers What can you do Formaldehyde in the Pesticide Properties DataBase PPDB Retrieved from https en wikipedia org w index php title Formaldehyde amp oldid 1205992816, wikipedia, wiki, book, books, library,

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