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Wikipedia

Vinyl chloride

Vinyl chloride is an organochloride with the formula H2C=CHCl. It is also called vinyl chloride monomer (VCM) or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer, poly(vinyl chloride) (PVC). Vinyl chloride monomer is among the top twenty largest petrochemicals (petroleum-derived chemicals) in world production.[2] The United States remains the largest vinyl chloride manufacturing region because of its low-production-cost position in chlorine and ethylene raw materials. China is also a large manufacturer and one of the largest consumers of vinyl chloride.[3] Vinyl chloride is a flammable gas that has a sweet odor and is carcinogenic. It can be formed in the environment when soil organisms break down chlorinated solvents. Vinyl chloride that is released by industries or formed by the breakdown of other chlorinated chemicals can enter the air and drinking water supplies. Vinyl chloride is a common contaminant found near landfills.[4] Before the 1970s, vinyl chloride was used as an aerosol propellant and refrigerant.[5][6]

Vinyl chloride
Structural formula of vinyl chloride
Space-filling model
Names
Preferred IUPAC name
Chloroethene
Other names
Vinyl chloride monomer
VCM
Chloroethylene
Refrigerant-1140
Identifiers
  • 75-01-4 Y
3D model (JSmol)
  • Interactive image
1731576
ChEBI
  • CHEBI:28509 Y
ChEMBL
  • ChEMBL2311071
ChemSpider
  • 6098 Y
ECHA InfoCard 100.000.756
EC Number
  • 200-831-0
100541
KEGG
  • C06793 Y
  • 6338
RTECS number
  • KU9625000
UNII
  • WD06X94M2D Y
UN number 1086
  • DTXSID8021434
  • InChI=1S/C2H3Cl/c1-2-3/h2H,1H2 Y
    Key: BZHJMEDXRYGGRV-UHFFFAOYSA-N Y
  • InChI=1/C2H3Cl/c1-2-3/h2H,1H2
    Key: BZHJMEDXRYGGRV-UHFFFAOYAW
  • ClC=C
Properties
C2H3Cl
Molar mass 62.50 g·mol−1
Appearance Colorless gas
Odor pleasant[1]
Density 0.911 g/cc
Melting point −153.8 °C (−244.8 °F; 119.3 K)
Boiling point −13.4 °C (7.9 °F; 259.8 K)
2.7 g/L (0.0432 mol/L)
Vapor pressure 2580 mmHg at 20 °C (68 °F)
-35.9·10−6 cm3/mol
Thermochemistry
0.8592 J/K/g (gas)
0.9504 J/K/g (solid)
−94.12 kJ/mol (solid)
Hazards
GHS labelling:
Danger
H220, H350
P201, P202, P210, P281, P308+P313, P377, P381, P403, P405, P501
NFPA 704 (fire diamond)
Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine 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 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3
4
2
Flash point −61 °C (−78 °F; 212 K)
Explosive limits 3.6–33%[1]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1 ppm C 5 ppm [15-minute][1]
REL (Recommended)
Ca[1]
IDLH (Immediate danger)
Ca [N.D.][1]
Related compounds
Related chloroethenes
dichloroethylenes, trichloroethylene, tetrachloroethylene
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 ?)

Uses edit

 
Poly(vinyl chloride) (PVC), the main end-product of vinyl chloride, is used extensively in sewage pipes due to its low cost, chemical resistance, and ease of jointing.

Vinyl chloride, also called vinyl chloride monomer (VCM), is exclusively used as a precursor to PVC. Due to its toxic nature, vinyl chloride is not found in other products. Poly(vinyl chloride) (PVC) is very stable, storable and not toxic.[2]

Until 1974, vinyl chloride was used in aerosol spray propellant.[7] Vinyl chloride was briefly used as an inhalational anaesthetic, in a similar vein to ethyl chloride, though its toxicity forced this practice to be abandoned.[8][9]

Production edit

To give a sense of scale, globally approximately 40 million tonnes of PVC resin are produced per year.[10] requiring a corresponding amount of vinyl chloride monomer.[11]

History edit

Vinyl chloride was first synthesized in 1835 by Justus von Liebig and his student Henri Victor Regnault. They obtained it by treating 1,2-dichloroethane with a solution of potassium hydroxide in ethanol.[12]

Acetylene-based routes edit

In 1912, Fritz Klatte, a German chemist working for Griesheim-Elektron, patented a means to produce vinyl chloride from acetylene and hydrogen chloride using mercuric chloride as a catalyst. The mercury-based technology is the main production method in China.[2] Acetylene reacts with hydrogen chloride over a mercuric chloride catalyst to give vinyl chloride:

C2H2 + HCl → CH2=CHCl

The reaction is exothermic and highly selective. Product purity and yields are generally very high.[2]

This route to vinyl chloride was common before ethylene became widely distributed. When vinyl chloride producers shifted to using the thermal cracking of EDC described below, some used byproduct HCl in conjunction with a colocated acetylene-based unit. The hazards of storing and shipping acetylene meant that the vinyl chloride facility needed to be located very close to the acetylene generating facility. China still uses this method to produce vinyl chloride due to the large reserves of coal from which acetylene is produced.[3][2]

In view of mercury's toxicity, gold- and platinum-based catalysts have been proposed.[13][14] This method was widely used during the 1930s and 1940s in the West.

Ethylene-based routes edit

In the United States and Europe, mercury-catalyzed routes have been superseded by more economical and greener processes based on ethylene. Ethylene is made by cracking ethane. Two steps are involved, chlorination and dehydrochlorination:

H2C=CH2 + Cl2 → H2ClC−CH2Cl
H2ClC−CH2Cl → H2C=CHCl + HCl

Possible routes from ethane edit

Numerous attempts have been made to convert ethane directly to vinyl chloride.[2] Ethane, which is even more readily available than ethylene, is a potential precursor to vinyl chloride. The conversion of ethane to vinyl chloride has been demonstrated by various routes:[2]

High-temperature chlorination:

H3C−CH3 + 2 Cl2 → H2C=CHCl + 3 HCl

High-temperature oxychlorination, which uses oxygen and hydrogen chloride in place of chlorine:

H3C−CH3 + O2 + HCl → H2C=CHCl + 2 H2O

High-temperature oxidative chlorination: 4 H3C−CH3 + 3 O2 + 2 Cl2 → 4 H2C=CHCl + 6 H2O

Thermal decomposition of dichloroethane edit

1,2-Dichloroethane, ClCH2CH2Cl (also known as ethylene dichloride, EDC), can be prepared by halogenation of ethane or ethylene, inexpensive starting materials. EDC thermally converts into vinyl chloride and anhydrous HCl. This production method has become the major route to vinyl chloride since the late 1950s.[2]

ClCH2−CH2Cl → CH2=CHCl + HCl

The thermal cracking reaction is highly endothermic, and is generally carried out in a fired heater. Even though residence time and temperature are carefully controlled, it produces significant quantities of chlorinated hydrocarbon side products. In practice, the yield for EDC conversion is relatively low (50 to 60 percent). The furnace effluent is immediately quenched with cold EDC to minimize undesirable side reactions. The resulting vapor-liquid mixture then goes to a purification system. Some processes use an absorber-stripper system to separate HCl from the chlorinated hydrocarbons, while other processes use a refrigerated continuous distillation system.[2]

Storage and transportation edit

Vinyl chloride is stored as a liquid. The accepted upper limit of safety as a health hazard is 500 ppm. Often, the storage containers for the product vinyl chloride are high capacity spheres. The spheres have an inside sphere and an outside sphere. Several inches of space separate the inside sphere from the outside sphere. The interstitial space between the spheres is purged with an inert gas such as nitrogen. As the nitrogen purge gas exits the interstitial space it passes through an analyzer that detects whether any vinyl chloride is leaking from the internal sphere. If vinyl chloride starts to leak from the internal sphere or if a fire is detected on the outside of the sphere then the contents of the sphere are automatically dumped into an emergency underground storage container. Containers used for handling vinyl chloride at atmospheric temperature are always under pressure. Inhibited vinyl chloride may be stored at normal atmospheric conditions in suitable pressure vessels. Uninhibited vinyl chloride may be stored either under refrigeration or at normal atmospheric temperature in the absence of air or sunlight but only for a duration of a few days. If stored for longer periods, regular checks must be made to confirm no polymerization has taken place.[15][better source needed]

In addition to its toxicity risk, transporting vinyl chloride also presents the same risks as transporting other flammable gases such as propane, butane, or natural gas.[16] Examples of incidents in which this danger was observed include the 2023 Ohio train derailment,[17][18] in which derailed tank cars dumped 100,000 gallons of hazardous materials, including vinyl chloride.[19][20]

Fire and explosion hazard edit

In the U.S., OSHA lists vinyl chloride as a Class IA Flammable Liquid, with a National Fire Protection Association Flammability Rating of 4. Because of its low boiling point, liquid vinyl chloride will undergo flash evaporation (i.e., autorefrigerate) upon its release to atmospheric pressure. The portion vaporized will form a dense cloud (more than twice as heavy as the surrounding air). The risk of subsequent explosion or fire is significant. According to OSHA, the flash point of vinyl chloride is −78 °C (−108.4 °F).[21] Its flammable limits in air are: lower 3.6 volume% and upper 33.0 volume%. The explosive limits are: lower 4.0%, upper 22.05% by volume in air. Fire may release toxic hydrogen chloride (HCl) and carbon monoxide (CO) and trace levels of phosgene.[22][23] Vinyl chloride can polymerise rapidly due to heating and under the influence of air, light and contact with a catalyst, strong oxidisers and metals such as copper and aluminium, with fire or explosion hazard. As a gas mixed with air, vinyl chloride is a fire and explosion hazard. On standing[clarification needed], vinyl chloride can form peroxides, which may then explode. Vinyl chloride will react with iron and steel in the presence of moisture.[6][24]

Health effects edit

Since it is a gas under most ambient conditions, primary exposure is via inhalation, as opposed to the consumption of contaminated food or water, with occupational hazards being highest. Prior to 1974, workers were commonly exposed to 1,000 ppm vinyl chloride, causing "vinyl chloride illness" such as acroosteolysis and Raynaud's Phenomenon. The symptoms of vinyl chloride exposure are classified by ppm levels in ambient air with 4,000 ppm having a threshold effect.[25] The intensity of symptoms varies from acute (1,000–8,000 ppm), including dizziness, nausea, visual disturbances, headache, and ataxia, to chronic (above 12,000 ppm), including narcotic effect, cardiac arrhythmias, and fatal respiratory failure.[26] RADS (Reactive Airway Dysfunction Syndrome) may be caused by acute exposure to vinyl chloride.[27]

Vinyl chloride is a mutagen having clastogenic effects which affect lymphocyte chromosomal structure.[26][28] Vinyl chloride is a IARC group 1 Carcinogen posing elevated risks of rare angiosarcoma, brain and lung tumors, and malignant haematopoeitic lymphatic tumors.[29] Chronic exposure leads to common forms of respiratory failure (emphysema, pulmonary fibrosis) and focused hepatotoxicity (hepatomegaly, hepatic fibrosis). Continuous exposure can cause CNS depression including euphoria and disorientation. Decreased male libido, miscarriage, and birth defects are known major reproductive defects associated with vinyl chloride.

Vinyl chloride can have acute dermal and ocular effects. Dermal exposure effects are thickening of skin, edema, decreased elasticity, local frostbites, blistering, and irritation.[26] The complete loss of skin elasticity expresses itself in Raynaud's Phenomenon.[28]

Liver toxicity edit

The hepatotoxicity of vinyl chloride has long been established since the 1930s when the PVC industry was just in its early stages. In the very first study about the dangers of vinyl chloride, published by Patty in 1930, it was disclosed that exposure of test animals to just a single short-term high dose of vinyl chloride caused liver damage.[30] In 1949, a Russian publication discussed the finding that vinyl chloride caused liver injury among workers.[31] In 1954, B.F. Goodrich Chemical stated that vinyl chloride caused liver injury upon short-term exposures. Almost nothing was known about its long-term effects. They also recommended long-term animal toxicology studies. The study noted that if a chemical did justify the cost of testing, and its ill-effects on workers and the public were known, the chemical should not be made.[32] In 1963, research paid for in part by Allied Chemical found liver damage in test animals from exposures below 500 parts per million (ppm).[33] Also in 1963, a Romanian researcher published findings of liver disease in vinyl chloride workers.[34] In 1968, Mutchler and Kramer, two Dow researchers, reported their finding that exposures as low as 300 ppm caused liver damage in vinyl chloride workers thus confirming earlier animal data in humans.[35] In a 1969 presentation given in Japan, P. L. Viola, a European researcher working for the European vinyl chloride industry, indicated, "every monomer used in V.C. manufacture is hazardous....various changes were found in bone and liver. Particularly, much more attention should be drawn to liver changes. The findings in rats at the concentration of 4 to 10 ppm are shown in pictures." In light of the finding of liver damage in rats from just 4–10 ppm of vinyl chloride exposure, Viola added that he "should like some precautions to be taken in the manufacturing plants polymerizing vinyl chloride, such as a reduction of the threshold limit value of monomer."[36] Vinyl chloride was first reported to induce angiosarcoma of the liver in 1974[37] and further research has demonstrated the carcinogenicity of VC to other organs and at lower concentrations,[38][39] with evidence now extending to jobs associated with poly(vinyl chloride) exposure, indicating the need for prudent control of PVC dust in the industrial setting.[40]

Vinyl chloride is now an IARC group 1 carcinogen known to cause hepatic angiosarcoma (HAS) in highly exposed industrial workers.[41] Vinyl chloride monomer, a component in the production of poly(vinyl chloride) (PVC) resins, is a halogenated hydrocarbon with acute toxic effects, as well as chronic carcinogenic effects.[42]

Cancerous tumors edit

Animals exposed to 30,000 ppm of vinyl chloride developed cancerous tumors. Studies on vinyl chloride workers were a "red flag" to B.F. Goodrich and the industry.[43] In 1972, Maltoni, another Italian researcher for the European vinyl chloride industry, found liver tumors (including angiosarcoma) from vinyl chloride exposures as low as 250 ppm for four hours a day.[44]

In 1997 the U.S. Centers for Disease Control and Prevention (CDC) concluded that the development and acceptance by the PVC industry of a closed loop polymerization process in the late 1970s "almost completely eliminated worker exposures" and that "new cases of hepatic angiosarcoma in vinyl chloride polymerization workers have been virtually eliminated."[45]

The Houston Chronicle claimed in 1998 that the vinyl industry manipulated vinyl chloride studies to avoid liability for worker exposure and hid extensive and severe chemical spills in local communities.[46]

Environment pollution edit

According to the U.S. EPA, "vinyl chloride emissions from poly(vinyl chloride) (PVC), ethylene dichloride (EDC), and vinyl chloride monomer (VCM) plants cause or contribute to air pollution that may reasonably be anticipated to result in an increase in mortality or an increase in serious irreversible, or incapacitating reversible illness. Vinyl chloride is a known human carcinogen that causes a rare cancer of the liver."[47] EPA's 2001 updated Toxicological Profile and Summary Health Assessment for vinyl chloride in its Integrated Risk Information System (IRIS) database lowers EPA's previous risk factor estimate by a factor of 20 and concludes that "because of the consistent evidence for liver cancer in all the studies...and the weaker association for other sites, it is concluded that the liver is the most sensitive site, and protection against liver cancer will protect against possible cancer induction in other tissues."[48]

Mechanism edit

The carcinogenicity of VC is attributed to the action of two metabolites, chloroethylene oxide and chloroacetaldehyde. The former is produced by the action of cytochrome P-450 on VC. Both chloroethylene oxide and chloroacetaldehyde are alkylating agents.

Microbial remediation edit

The bacteria species Nitrosomonas europaea can degrade a variety of halogenated compounds including trichloroethylene, and vinyl chloride.[49]

See also edit

References edit

Additional references for environmental pollution edit

  • International Programme on Chemical Safety (IPCS) (1999). Vinyl chloride. Environmental Health Criteria 215. WHO, Geneva.
  • National Poisons Information Service (NPIS) (2004). "Vinyl chloride." TOXBASE®.
  • World Health Organisation (WHO) (2000). "Air quality guidelines for Europe." WHO Regional Publications, European Series, No. 91. 2nd edition. WHO Regional Office for Europe. Copenhagen.
  • Hathaway G.J. and Proctor N.H. (2004). Chemical Hazards of the Workplace. 5th edition. John Wiley & Sons, New Jersey.
  • Risk Assessment Information System (RAIS) (1993). "Toxicity summary for vinyl chloride. "Chemical Hazard Evaluation and Communication Group, Biomedical and Environmental Information Analysis Section, Health and Safety Research Division.

Inline citations edit

  1. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0658". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b c d e f g h i Dreher, Eberhard-Ludwig; Torkelson, Theodore R.; Beutel, Klaus K. (2011). "Chlorethanes and Chloroethylenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o06_o01. ISBN 978-3527306732.
  3. ^ a b "Vinyl Chloride Monomer (VCM) – Chemical Economics Handbook". S&P Global. from the original on 18 August 2014. Retrieved 5 April 2018.
  4. ^ "Vinyl Chloride". Wisconsin Department of Health Services. 2018-01-30. from the original on 2023-02-07. Retrieved 2023-02-07.
  5. ^ Fralish, Matthew S.; Downs, John W. (June 21, 2022). "Vinyl Chloride Toxicity". National Library of Medicine. PMID 31335054. from the original on February 21, 2023. Retrieved February 21, 2023.
  6. ^ a b "Vinyl Chloride Monomer (VCM)". Department of Climate Change, Energy, the Environment and Water. from the original on 2023-02-06.
  7. ^ Markowitz, Gerald; Rosner, David (2013). Deceit and Denial: The Deadly Politics of Industrial Pollution. Berkeley, California Press: University of California Press. p. 185.[dead link]
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  10. ^ "PVC applications". The European Council of Vinyl Manufacturers. Retrieved 2023-02-25.
  11. ^ "Investigating the Safety of Vinyl Chloride in PVC Pipes for Drinking Water. Plumbing Navigator". Plumbingnav. Grabowski, B. Retrieved April 12, 2023.
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  13. ^ Malta, Grazia; Kondrat, Simon A.; Freakley, Simon J.; Davies, Catherine J.; Lu, Li; Dawson, Simon; Thetford, Adam; Gibson, Emma K.; Morgan, David J.; Jones, Wilm; Wells, Peter P.; Johnston, Peter; Catlow, C. Richard A.; Kiely, Christopher J.; Hutchings, Graham J. (2017). "Identification of single-site gold catalysis in acetylene hydrochlorination". Science. 355 (6332): 1399–1403. Bibcode:2017Sci...355.1399M. doi:10.1126/science.aal3439. PMID 28360324. S2CID 206655247.
  14. ^ Kaiser, Selina K.; Fako, Edvin; Manzocchi, Gabriele; Krumeich, Frank; Hauert, Roland; Clark, Adam H.; Safonova, Olga V.; López, Núria; Pérez-Ramírez, Javier (2020). "Nanostructuring unlocks high performance of platinum single-atom catalysts for stable vinyl chloride production". Nature Catalysis. 3 (4): 376–385. doi:10.1038/s41929-020-0431-3. PMC 7156288. PMID 32292878.
  15. ^ (PDF). Archived from the original (PDF) on 2013-10-20. Retrieved 2013-10-06.
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  17. ^ Orsagos, Patrick; Seewer, John (February 6, 2023). "Crews release toxic chemicals from derailed tankers in Ohio". Associated Press. from the original on February 7, 2023. Retrieved February 14, 2023.
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  21. ^ (PDF). Archived from the original (PDF) on 2013-10-20. Retrieved 2013-10-06.
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  28. ^ a b Agency for Toxic Substances and Disease Registry (July 2006). Toxicological profile for vinyl chloride (PDF) (Report). Atlanta, US: U.S. Department of Health and Human Services. (PDF) from the original on 2023-02-15. Retrieved 2023-02-07.
  29. ^ International Agency for Research on Cancer (IARC). "Vinyl chloride, polyvinyl chloride, and vinyl chloride-vinyl acetate copolymers." Vol 19, 1979. IARC. "Vinyl chloride." Supplement 7, 1987. Lyon.
  30. ^ Patty, F. A.; Yant, W. P.; Waite, C. P. (1930). "Acute Response of Guinea Pigs to Vapors of Some New Commercial Organic Compounds: V. Vinyl Chloride". Public Health Reports. 45 (34): 1963. doi:10.2307/4579760. JSTOR 4579760. from the original on 2020-02-09. Retrieved 2023-02-08.
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  34. ^ Suciu, I.; Prodan, L.; Ilea, Elena; Păduraru, A.; Pascu, Livia (January 1975). "Clinical Manifestations in Vinyl Chloride Poisoning". Annals of the New York Academy of Sciences. 246 (1): 53–69. Bibcode:1975NYASA.246...53S. doi:10.1111/j.1749-6632.1975.tb51080.x. ISSN 0077-8923. PMID 1054970. S2CID 30706677.
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  36. ^ Viola, P.L. "Pathology of Vinyl Chloride" International Congress on Occupational Health. Japan. 1969.
  37. ^ Wagoner, Joseph K. (1983). "Toxicity of Vinyl Chloride and Poly(Vinyl Chloride): A Critical Review". Environmental Health Perspectives. 52: 61–66. doi:10.2307/3429651. ISSN 0091-6765. JSTOR 3429651. PMC 1569348. PMID 6360677.
  38. ^ Winsten, Jay A.; Watson, James D.; Hiatt, Howard H.; Cold Spring Harbor Laboratory, eds. (1977). Origins of human cancer. Cold Spring Harbor conferences on cell proliferation. Vol. Book A. Incidence of cancer in humans. Cold Spring Harbor, N.Y.: Cold Spring Harbor Laboratory. p. 119. ISBN 978-0-87969-119-6.
  39. ^ Maltoni, C.; Lefemine, G.; Ciliberti, A.; Cotti, G.; Carretti, D. (1981-10-01). "Carcinogenicity bioassays of vinyl chloride monomer: a model of risk assessment on an experimental basis". Environmental Health Perspectives. 41: 3–29. doi:10.1289/ehp.81413. ISSN 0091-6765. PMC 1568874. PMID 6800782.
  40. ^ Wagoner, J K (1983-10-01). "Toxicity of vinyl chloride and poly(vinyl chloride): a critical review". Environmental Health Perspectives. 52: 61–66. doi:10.1289/ehp.835261. ISSN 0091-6765. PMC 1569348. PMID 6360677.
  41. ^ Sass, Jennifer Beth; Castleman, Barry; Wallinga, David (2005-07-01). "Vinyl chloride: a case study of data suppression and misrepresentation". Environmental Health Perspectives. 113 (7): 809–812. doi:10.1289/ehp.7716. ISSN 1552-9924. PMC 1257639. PMID 16002366.
  42. ^ PMC, Europe. "Europe PMC". europepmc.org. Retrieved 2023-02-18.
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  44. ^ Maltoni, C. "Cancer Detection and Prevention" (1972) Presented at the Second International Symposium on Cancer Detection and Prevention. Bologna, April 9–12, 1973.
  45. ^ Epidemiologic Notes and Reports Angiosarcoma of the Liver Among Polyvinyl Chloride Workers – Kentucky 2010-09-16 at the Wayback Machine. Centers for Disease Control and Prevention. 1997.
  46. ^ Jim Morris, "In Strictest Confidence. The chemical industry's secrets," Houston Chronicle. Part One: "Toxic Secrecy," June 28, 1998, pp. 1A, 24A–27A; Part Two: "High-Level Crime," June 29, 1998, pp. 1A, 8A, 9A; and Part Three: "Bane on the Bayou," July 26, 1998, pgs. 1A, 16A.
  47. ^ National Emission Standards for Hazardous Air Pollutants (NESHAP) for Vinyl Chloride Subpart F, OMB Control Number 2060-0071, EPA ICR Number 0186.09 (Federal Register: September 25, 2001 (Volume 66, Number 186) March 22, 2003, at the Wayback Machine)
  48. ^ EPA Toxicological Review of Vinyl Chloride in Support of Information on the IRIS. May 2000
  49. ^ . genome.jgi-psf.org. Archived from the original on 3 July 2009. Retrieved 5 April 2018.

Further reading edit

  • . Time. May 13, 1974. Archived from the original on June 12, 2007. Retrieved 2 July 2010.

External links edit

  • ATSDR Toxicological Profile for chloroethene / vinyl chloride
  • CDC – NIOSH Pocket Guide to Chemical Hazards
  • Chemical Identifiers for Vinyl Chloride from CAMEO Chemicals

vinyl, chloride, organochloride, with, formula, chcl, also, called, vinyl, chloride, monomer, chloroethene, this, colorless, compound, important, industrial, chemical, chiefly, used, produce, polymer, poly, vinyl, chloride, monomer, among, twenty, largest, pet. Vinyl chloride is an organochloride with the formula H2C CHCl It is also called vinyl chloride monomer VCM or chloroethene This colorless compound is an important industrial chemical chiefly used to produce the polymer poly vinyl chloride PVC Vinyl chloride monomer is among the top twenty largest petrochemicals petroleum derived chemicals in world production 2 The United States remains the largest vinyl chloride manufacturing region because of its low production cost position in chlorine and ethylene raw materials China is also a large manufacturer and one of the largest consumers of vinyl chloride 3 Vinyl chloride is a flammable gas that has a sweet odor and is carcinogenic It can be formed in the environment when soil organisms break down chlorinated solvents Vinyl chloride that is released by industries or formed by the breakdown of other chlorinated chemicals can enter the air and drinking water supplies Vinyl chloride is a common contaminant found near landfills 4 Before the 1970s vinyl chloride was used as an aerosol propellant and refrigerant 5 6 Vinyl chloride Structural formula of vinyl chloride Space filling model Names Preferred IUPAC name Chloroethene Other names Vinyl chloride monomerVCMChloroethyleneRefrigerant 1140 Identifiers CAS Number 75 01 4 Y 3D model JSmol Interactive image Beilstein Reference 1731576 ChEBI CHEBI 28509 Y ChEMBL ChEMBL2311071 ChemSpider 6098 Y ECHA InfoCard 100 000 756 EC Number 200 831 0 Gmelin Reference 100541 KEGG C06793 Y PubChem CID 6338 RTECS number KU9625000 UNII WD06X94M2D Y UN number 1086 CompTox Dashboard EPA DTXSID8021434 InChI InChI 1S C2H3Cl c1 2 3 h2H 1H2 YKey BZHJMEDXRYGGRV UHFFFAOYSA N YInChI 1 C2H3Cl c1 2 3 h2H 1H2Key BZHJMEDXRYGGRV UHFFFAOYAW SMILES ClC C Properties Chemical formula C 2H 3Cl Molar mass 62 50 g mol 1 Appearance Colorless gas Odor pleasant 1 Density 0 911 g cc Melting point 153 8 C 244 8 F 119 3 K Boiling point 13 4 C 7 9 F 259 8 K Solubility in water 2 7 g L 0 0432 mol L Vapor pressure 2580 mmHg at 20 C 68 F Magnetic susceptibility x 35 9 10 6 cm3 mol Thermochemistry Heat capacity C 0 8592 J K g gas 0 9504 J K g solid Std enthalpy offormation DfH 298 94 12 kJ mol solid Hazards GHS labelling Pictograms Signal word Danger Hazard statements H220 H350 Precautionary statements P201 P202 P210 P281 P308 P313 P377 P381 P403 P405 P501 NFPA 704 fire diamond 342 Flash point 61 C 78 F 212 K Explosive limits 3 6 33 1 NIOSH US health exposure limits PEL Permissible TWA 1 ppm C 5 ppm 15 minute 1 REL Recommended Ca 1 IDLH Immediate danger Ca N D 1 Related compounds Related chloroethenes dichloroethylenes trichloroethylene tetrachloroethylene Except 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 Contents 1 Uses 2 Production 2 1 History 2 2 Acetylene based routes 2 3 Ethylene based routes 2 4 Possible routes from ethane 2 4 1 Thermal decomposition of dichloroethane 3 Storage and transportation 4 Fire and explosion hazard 5 Health effects 5 1 Liver toxicity 5 2 Cancerous tumors 5 3 Environment pollution 5 4 Mechanism 6 Microbial remediation 7 See also 8 References 8 1 Additional references for environmental pollution 8 2 Inline citations 9 Further reading 10 External linksUses edit nbsp Poly vinyl chloride PVC the main end product of vinyl chloride is used extensively in sewage pipes due to its low cost chemical resistance and ease of jointing Vinyl chloride also called vinyl chloride monomer VCM is exclusively used as a precursor to PVC Due to its toxic nature vinyl chloride is not found in other products Poly vinyl chloride PVC is very stable storable and not toxic 2 Until 1974 vinyl chloride was used in aerosol spray propellant 7 Vinyl chloride was briefly used as an inhalational anaesthetic in a similar vein to ethyl chloride though its toxicity forced this practice to be abandoned 8 9 Production editTo give a sense of scale globally approximately 40 million tonnes of PVC resin are produced per year 10 requiring a corresponding amount of vinyl chloride monomer 11 History edit Vinyl chloride was first synthesized in 1835 by Justus von Liebig and his student Henri Victor Regnault They obtained it by treating 1 2 dichloroethane with a solution of potassium hydroxide in ethanol 12 Acetylene based routes edit In 1912 Fritz Klatte a German chemist working for Griesheim Elektron patented a means to produce vinyl chloride from acetylene and hydrogen chloride using mercuric chloride as a catalyst The mercury based technology is the main production method in China 2 Acetylene reacts with hydrogen chloride over a mercuric chloride catalyst to give vinyl chloride C2H2 HCl CH2 CHCl The reaction is exothermic and highly selective Product purity and yields are generally very high 2 This route to vinyl chloride was common before ethylene became widely distributed When vinyl chloride producers shifted to using the thermal cracking of EDC described below some used byproduct HCl in conjunction with a colocated acetylene based unit The hazards of storing and shipping acetylene meant that the vinyl chloride facility needed to be located very close to the acetylene generating facility China still uses this method to produce vinyl chloride due to the large reserves of coal from which acetylene is produced 3 2 In view of mercury s toxicity gold and platinum based catalysts have been proposed 13 14 This method was widely used during the 1930s and 1940s in the West Ethylene based routes edit In the United States and Europe mercury catalyzed routes have been superseded by more economical and greener processes based on ethylene Ethylene is made by cracking ethane Two steps are involved chlorination and dehydrochlorination H2C CH2 Cl2 H2ClC CH2Cl H2ClC CH2Cl H2C CHCl HCl Possible routes from ethane edit Numerous attempts have been made to convert ethane directly to vinyl chloride 2 Ethane which is even more readily available than ethylene is a potential precursor to vinyl chloride The conversion of ethane to vinyl chloride has been demonstrated by various routes 2 High temperature chlorination H3C CH3 2 Cl2 H2C CHCl 3 HCl High temperature oxychlorination which uses oxygen and hydrogen chloride in place of chlorine H3C CH3 O2 HCl H2C CHCl 2 H2O High temperature oxidative chlorination 4 H3C CH3 3 O2 2 Cl2 4 H2C CHCl 6 H2O Thermal decomposition of dichloroethane edit 1 2 Dichloroethane ClCH2CH2Cl also known as ethylene dichloride EDC can be prepared by halogenation of ethane or ethylene inexpensive starting materials EDC thermally converts into vinyl chloride and anhydrous HCl This production method has become the major route to vinyl chloride since the late 1950s 2 ClCH2 CH2Cl CH2 CHCl HCl The thermal cracking reaction is highly endothermic and is generally carried out in a fired heater Even though residence time and temperature are carefully controlled it produces significant quantities of chlorinated hydrocarbon side products In practice the yield for EDC conversion is relatively low 50 to 60 percent The furnace effluent is immediately quenched with cold EDC to minimize undesirable side reactions The resulting vapor liquid mixture then goes to a purification system Some processes use an absorber stripper system to separate HCl from the chlorinated hydrocarbons while other processes use a refrigerated continuous distillation system 2 Storage and transportation editVinyl chloride is stored as a liquid The accepted upper limit of safety as a health hazard is 500 ppm Often the storage containers for the product vinyl chloride are high capacity spheres The spheres have an inside sphere and an outside sphere Several inches of space separate the inside sphere from the outside sphere The interstitial space between the spheres is purged with an inert gas such as nitrogen As the nitrogen purge gas exits the interstitial space it passes through an analyzer that detects whether any vinyl chloride is leaking from the internal sphere If vinyl chloride starts to leak from the internal sphere or if a fire is detected on the outside of the sphere then the contents of the sphere are automatically dumped into an emergency underground storage container Containers used for handling vinyl chloride at atmospheric temperature are always under pressure Inhibited vinyl chloride may be stored at normal atmospheric conditions in suitable pressure vessels Uninhibited vinyl chloride may be stored either under refrigeration or at normal atmospheric temperature in the absence of air or sunlight but only for a duration of a few days If stored for longer periods regular checks must be made to confirm no polymerization has taken place 15 better source needed In addition to its toxicity risk transporting vinyl chloride also presents the same risks as transporting other flammable gases such as propane butane or natural gas 16 Examples of incidents in which this danger was observed include the 2023 Ohio train derailment 17 18 in which derailed tank cars dumped 100 000 gallons of hazardous materials including vinyl chloride 19 20 Fire and explosion hazard editIn the U S OSHA lists vinyl chloride as a Class IA Flammable Liquid with a National Fire Protection Association Flammability Rating of 4 Because of its low boiling point liquid vinyl chloride will undergo flash evaporation i e autorefrigerate upon its release to atmospheric pressure The portion vaporized will form a dense cloud more than twice as heavy as the surrounding air The risk of subsequent explosion or fire is significant According to OSHA the flash point of vinyl chloride is 78 C 108 4 F 21 Its flammable limits in air are lower 3 6 volume and upper 33 0 volume The explosive limits are lower 4 0 upper 22 05 by volume in air Fire may release toxic hydrogen chloride HCl and carbon monoxide CO and trace levels of phosgene 22 23 Vinyl chloride can polymerise rapidly due to heating and under the influence of air light and contact with a catalyst strong oxidisers and metals such as copper and aluminium with fire or explosion hazard As a gas mixed with air vinyl chloride is a fire and explosion hazard On standing clarification needed vinyl chloride can form peroxides which may then explode Vinyl chloride will react with iron and steel in the presence of moisture 6 24 Health effects editSince it is a gas under most ambient conditions primary exposure is via inhalation as opposed to the consumption of contaminated food or water with occupational hazards being highest Prior to 1974 workers were commonly exposed to 1 000 ppm vinyl chloride causing vinyl chloride illness such as acroosteolysis and Raynaud s Phenomenon The symptoms of vinyl chloride exposure are classified by ppm levels in ambient air with 4 000 ppm having a threshold effect 25 The intensity of symptoms varies from acute 1 000 8 000 ppm including dizziness nausea visual disturbances headache and ataxia to chronic above 12 000 ppm including narcotic effect cardiac arrhythmias and fatal respiratory failure 26 RADS Reactive Airway Dysfunction Syndrome may be caused by acute exposure to vinyl chloride 27 Vinyl chloride is a mutagen having clastogenic effects which affect lymphocyte chromosomal structure 26 28 Vinyl chloride is a IARC group 1 Carcinogen posing elevated risks of rare angiosarcoma brain and lung tumors and malignant haematopoeitic lymphatic tumors 29 Chronic exposure leads to common forms of respiratory failure emphysema pulmonary fibrosis and focused hepatotoxicity hepatomegaly hepatic fibrosis Continuous exposure can cause CNS depression including euphoria and disorientation Decreased male libido miscarriage and birth defects are known major reproductive defects associated with vinyl chloride Vinyl chloride can have acute dermal and ocular effects Dermal exposure effects are thickening of skin edema decreased elasticity local frostbites blistering and irritation 26 The complete loss of skin elasticity expresses itself in Raynaud s Phenomenon 28 Liver toxicity edit The hepatotoxicity of vinyl chloride has long been established since the 1930s when the PVC industry was just in its early stages In the very first study about the dangers of vinyl chloride published by Patty in 1930 it was disclosed that exposure of test animals to just a single short term high dose of vinyl chloride caused liver damage 30 In 1949 a Russian publication discussed the finding that vinyl chloride caused liver injury among workers 31 In 1954 B F Goodrich Chemical stated that vinyl chloride caused liver injury upon short term exposures Almost nothing was known about its long term effects They also recommended long term animal toxicology studies The study noted that if a chemical did justify the cost of testing and its ill effects on workers and the public were known the chemical should not be made 32 In 1963 research paid for in part by Allied Chemical found liver damage in test animals from exposures below 500 parts per million ppm 33 Also in 1963 a Romanian researcher published findings of liver disease in vinyl chloride workers 34 In 1968 Mutchler and Kramer two Dow researchers reported their finding that exposures as low as 300 ppm caused liver damage in vinyl chloride workers thus confirming earlier animal data in humans 35 In a 1969 presentation given in Japan P L Viola a European researcher working for the European vinyl chloride industry indicated every monomer used in V C manufacture is hazardous various changes were found in bone and liver Particularly much more attention should be drawn to liver changes The findings in rats at the concentration of 4 to 10 ppm are shown in pictures In light of the finding of liver damage in rats from just 4 10 ppm of vinyl chloride exposure Viola added that he should like some precautions to be taken in the manufacturing plants polymerizing vinyl chloride such as a reduction of the threshold limit value of monomer 36 Vinyl chloride was first reported to induce angiosarcoma of the liver in 1974 37 and further research has demonstrated the carcinogenicity of VC to other organs and at lower concentrations 38 39 with evidence now extending to jobs associated with poly vinyl chloride exposure indicating the need for prudent control of PVC dust in the industrial setting 40 Vinyl chloride is now an IARC group 1 carcinogen known to cause hepatic angiosarcoma HAS in highly exposed industrial workers 41 Vinyl chloride monomer a component in the production of poly vinyl chloride PVC resins is a halogenated hydrocarbon with acute toxic effects as well as chronic carcinogenic effects 42 Cancerous tumors edit Animals exposed to 30 000 ppm of vinyl chloride developed cancerous tumors Studies on vinyl chloride workers were a red flag to B F Goodrich and the industry 43 In 1972 Maltoni another Italian researcher for the European vinyl chloride industry found liver tumors including angiosarcoma from vinyl chloride exposures as low as 250 ppm for four hours a day 44 In 1997 the U S Centers for Disease Control and Prevention CDC concluded that the development and acceptance by the PVC industry of a closed loop polymerization process in the late 1970s almost completely eliminated worker exposures and that new cases of hepatic angiosarcoma in vinyl chloride polymerization workers have been virtually eliminated 45 The Houston Chronicle claimed in 1998 that the vinyl industry manipulated vinyl chloride studies to avoid liability for worker exposure and hid extensive and severe chemical spills in local communities 46 Environment pollution edit According to the U S EPA vinyl chloride emissions from poly vinyl chloride PVC ethylene dichloride EDC and vinyl chloride monomer VCM plants cause or contribute to air pollution that may reasonably be anticipated to result in an increase in mortality or an increase in serious irreversible or incapacitating reversible illness Vinyl chloride is a known human carcinogen that causes a rare cancer of the liver 47 EPA s 2001 updated Toxicological Profile and Summary Health Assessment for vinyl chloride in its Integrated Risk Information System IRIS database lowers EPA s previous risk factor estimate by a factor of 20 and concludes that because of the consistent evidence for liver cancer in all the studies and the weaker association for other sites it is concluded that the liver is the most sensitive site and protection against liver cancer will protect against possible cancer induction in other tissues 48 Mechanism edit The carcinogenicity of VC is attributed to the action of two metabolites chloroethylene oxide and chloroacetaldehyde The former is produced by the action of cytochrome P 450 on VC Both chloroethylene oxide and chloroacetaldehyde are alkylating agents Microbial remediation editThe bacteria species Nitrosomonas europaea can degrade a variety of halogenated compounds including trichloroethylene and vinyl chloride 49 See also editVinyl group List of refrigerants for R 1140 2023 Ohio train derailment in which a large amount of vinyl chloride was spilledReferences editAdditional references for environmental pollution edit International Programme on Chemical Safety IPCS 1999 Vinyl chloride Environmental Health Criteria 215 WHO Geneva National Poisons Information Service NPIS 2004 Vinyl chloride TOXBASE World Health Organisation WHO 2000 Air quality guidelines for Europe WHO Regional Publications European Series No 91 2nd edition WHO Regional Office for Europe Copenhagen Hathaway G J and Proctor N H 2004 Chemical Hazards of the Workplace 5th edition John Wiley amp Sons New Jersey Risk Assessment Information System RAIS 1993 Toxicity summary for vinyl chloride Chemical Hazard Evaluation and Communication Group Biomedical and Environmental Information Analysis Section Health and Safety Research Division Inline citations edit a b c d e NIOSH Pocket Guide to Chemical Hazards 0658 National Institute for Occupational Safety and Health NIOSH a b c d e f g h i Dreher Eberhard Ludwig Torkelson Theodore R Beutel Klaus K 2011 Chlorethanes and Chloroethylenes Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 o06 o01 ISBN 978 3527306732 a b Vinyl Chloride Monomer VCM Chemical Economics Handbook S amp P Global Archived from the original on 18 August 2014 Retrieved 5 April 2018 Vinyl Chloride Wisconsin Department of Health Services 2018 01 30 Archived from the original on 2023 02 07 Retrieved 2023 02 07 Fralish Matthew S Downs John W June 21 2022 Vinyl Chloride Toxicity National Library of Medicine PMID 31335054 Archived from the original on February 21 2023 Retrieved February 21 2023 a b Vinyl Chloride Monomer VCM Department of Climate Change Energy the Environment and Water Archived from the original on 2023 02 06 Markowitz Gerald Rosner David 2013 Deceit and Denial The Deadly Politics of Industrial Pollution Berkeley California Press University of California Press p 185 dead link Tamburro CH 1978 Health effects of vinyl chloride Texas Reports on Biology and Medicine 37 126 44 146 51 PMID 572591 Oster RH Carr CJ July 1947 Anesthesia narcosis with vinyl chloride Anesthesiology 8 4 359 61 doi 10 1097 00000542 194707000 00003 PMID 20255056 S2CID 73229069 Archived from the original on 2023 02 15 Retrieved 2023 02 15 PVC applications The European Council of Vinyl Manufacturers Retrieved 2023 02 25 Investigating the Safety of Vinyl Chloride in PVC Pipes for Drinking Water Plumbing Navigator Plumbingnav Grabowski B Retrieved April 12 2023 Regnault H V 1835 Sur la Composition de la Liqueur des Hollandais et sur une nouvelle Substance etheree Annales de Chimie et de Physique 5858 Gay Lussac amp Arago 301 320 Archived from the original on 2019 07 11 Retrieved 2019 07 11 Malta Grazia Kondrat Simon A Freakley Simon J Davies Catherine J Lu Li Dawson Simon Thetford Adam Gibson Emma K Morgan David J Jones Wilm Wells Peter P Johnston Peter Catlow C Richard A Kiely Christopher J Hutchings Graham J 2017 Identification of single site gold catalysis in acetylene hydrochlorination Science 355 6332 1399 1403 Bibcode 2017Sci 355 1399M doi 10 1126 science aal3439 PMID 28360324 S2CID 206655247 Kaiser Selina K Fako Edvin Manzocchi Gabriele Krumeich Frank Hauert Roland Clark Adam H Safonova Olga V Lopez Nuria Perez Ramirez Javier 2020 Nanostructuring unlocks high performance of platinum single atom catalysts for stable vinyl chloride production Nature Catalysis 3 4 376 385 doi 10 1038 s41929 020 0431 3 PMC 7156288 PMID 32292878 aseh net PDF Archived from the original PDF on 2013 10 20 Retrieved 2013 10 06 Vinyl Chloride Monomer VCM Production The European Council of Vinyl Manufacturers Archived from the original on 2019 01 07 Orsagos Patrick Seewer John February 6 2023 Crews release toxic chemicals from derailed tankers in Ohio Associated Press Archived from the original on February 7 2023 Retrieved February 14 2023 Ohio catastrophe is wake up call to dangers of deadly train derailments The Guardian February 11 2023 Archived from the original on February 13 2023 Retrieved February 13 2023 NTSB Issues Investigative Update on Ohio Train Derailment National Transportation Safety Board 2023 Archived from the original on February 19 2023 Retrieved April 19 2023 TRAIN 32N EAST PALESTINE xlsx PDF Environmental Protection Agency 2023 Archived PDF from the original on February 17 2023 Retrieved April 19 2023 Aseh net PDF Archived from the original PDF on 2013 10 20 Retrieved 2013 10 06 Occupational Safety and Health Guideline for Vinyl Chloride 1988 O Mara M M Grider L B Daniel R L March 1971 Combustion Products from Vinyl Chloride Monomer American Industrial Hygiene Association Journal 32 3 153 156 doi 10 1080 0002889718506429 PMID 5551110 Vinyl chloride health effects incident management and toxicology www gov uk Archived from the original on 10 February 2018 Retrieved 5 April 2018 Harrison Henrietta 2008 Vinyl chloride Toxicological overview Health Protecction Agency UK a b c International Programme on Chemical Safety IPCS 1999 Vinyl chloride Environmental Health Criteria 215 WHO Geneva UK Department for Environment Food and Rural Affairs DEFRA and Environment Agency EA 2004 Contaminants in soil Collation of toxicological data and intake values for humans Vinyl chloride a b Agency for Toxic Substances and Disease Registry July 2006 Toxicological profile for vinyl chloride PDF Report Atlanta US U S Department of Health and Human Services Archived PDF from the original on 2023 02 15 Retrieved 2023 02 07 International Agency for Research on Cancer IARC Vinyl chloride polyvinyl chloride and vinyl chloride vinyl acetate copolymers Vol 19 1979 IARC Vinyl chloride Supplement 7 1987 Lyon Patty F A Yant W P Waite C P 1930 Acute Response of Guinea Pigs to Vapors of Some New Commercial Organic Compounds V Vinyl Chloride Public Health Reports 45 34 1963 doi 10 2307 4579760 JSTOR 4579760 Archived from the original on 2020 02 09 Retrieved 2023 02 08 Tribukh S L et al Working Conditions and Measures for Their Improvement in Production and Use of Vinylchloride Plastics 1949 Wilson Rex H et al Toxicology of Plastics and Rubber Plastomers and Monomers Reprinted from Industrial Medicine and Surgery 23 11 479 786 November 1954 Lester D Greenberg L A Adams W Robert May 1963 Effects of Single and Repeated Exposures of Humans and Rats to Vinyl Chloride American Industrial Hygiene Association Journal 24 3 265 275 doi 10 1080 00028896309342963 ISSN 0002 8894 PMID 13929916 Archived from the original on 2023 02 18 Retrieved 2023 02 07 Suciu I Prodan L Ilea Elena Păduraru A Pascu Livia January 1975 Clinical Manifestations in Vinyl Chloride Poisoning Annals of the New York Academy of Sciences 246 1 53 69 Bibcode 1975NYASA 246 53S doi 10 1111 j 1749 6632 1975 tb51080 x ISSN 0077 8923 PMID 1054970 S2CID 30706677 Kramer G C M D The Correlation of Clinical and Environmental Measurements for Workers Exposed to Vinyl Chloride The Dow Chemical Company Midland Michigan Viola P L Pathology of Vinyl Chloride International Congress on Occupational Health Japan 1969 Wagoner Joseph K 1983 Toxicity of Vinyl Chloride and Poly Vinyl Chloride A Critical Review Environmental Health Perspectives 52 61 66 doi 10 2307 3429651 ISSN 0091 6765 JSTOR 3429651 PMC 1569348 PMID 6360677 Winsten Jay A Watson James D Hiatt Howard H Cold Spring Harbor Laboratory eds 1977 Origins of human cancer Cold Spring Harbor conferences on cell proliferation Vol Book A Incidence of cancer in humans Cold Spring Harbor N Y Cold Spring Harbor Laboratory p 119 ISBN 978 0 87969 119 6 Maltoni C Lefemine G Ciliberti A Cotti G Carretti D 1981 10 01 Carcinogenicity bioassays of vinyl chloride monomer a model of risk assessment on an experimental basis Environmental Health Perspectives 41 3 29 doi 10 1289 ehp 81413 ISSN 0091 6765 PMC 1568874 PMID 6800782 Wagoner J K 1983 10 01 Toxicity of vinyl chloride and poly vinyl chloride a critical review Environmental Health Perspectives 52 61 66 doi 10 1289 ehp 835261 ISSN 0091 6765 PMC 1569348 PMID 6360677 Sass Jennifer Beth Castleman Barry Wallinga David 2005 07 01 Vinyl chloride a case study of data suppression and misrepresentation Environmental Health Perspectives 113 7 809 812 doi 10 1289 ehp 7716 ISSN 1552 9924 PMC 1257639 PMID 16002366 PMC Europe Europe PMC europepmc org Retrieved 2023 02 18 Viola P L Carcinogenic Effect of Vinyl Chloride Presented at the Tenth International Cancer Congress Houston Texas May 22 29 1970 Maltoni C Cancer Detection and Prevention 1972 Presented at the Second International Symposium on Cancer Detection and Prevention Bologna April 9 12 1973 Epidemiologic Notes and Reports Angiosarcoma of the Liver Among Polyvinyl Chloride Workers Kentucky Archived 2010 09 16 at the Wayback Machine Centers for Disease Control and Prevention 1997 Jim Morris In Strictest Confidence The chemical industry s secrets Houston Chronicle Part One Toxic Secrecy June 28 1998 pp 1A 24A 27A Part Two High Level Crime June 29 1998 pp 1A 8A 9A and Part Three Bane on the Bayou July 26 1998 pgs 1A 16A National Emission Standards for Hazardous Air Pollutants NESHAP for Vinyl Chloride Subpart F OMB Control Number 2060 0071 EPA ICR Number 0186 09 Federal Register September 25 2001 Volume 66 Number 186 Archived March 22 2003 at the Wayback Machine EPA Toxicological Review of Vinyl Chloride in Support of Information on the IRIS May 2000 Home Nitrosomonas europaea genome jgi psf org Archived from the original on 3 July 2009 Retrieved 5 April 2018 Further reading edit Medicine The Plastic Peril Time May 13 1974 Archived from the original on June 12 2007 Retrieved 2 July 2010 External links editInformation on the aerosol propellant controversy ATSDR Toxicological Profile for chloroethene vinyl chloride CDC NIOSH Pocket Guide to Chemical Hazards Chemical Identifiers for Vinyl Chloride from CAMEO Chemicals Retrieved from https en wikipedia org w index php title Vinyl chloride amp oldid 1214132365, wikipedia, wiki, book, books, library,

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