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Wikipedia

Cellulose

Cellulose is an organic compound with the formula (C
6
H
10
O
5
)
n
, a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units.[3][4] Cellulose is an important structural component of the primary cell wall of green plants, many forms of algae and the oomycetes. Some species of bacteria secrete it to form biofilms.[5] Cellulose is the most abundant organic polymer on Earth.[6] The cellulose content of cotton fiber is 90%, that of wood is 40–50%, and that of dried hemp is approximately 57%.[7][8][9]

Cellulose[1]
Identifiers
  • 9004-34-6 Y
ChEMBL
  • ChEMBL2109009 N
ChemSpider
  • None
ECHA InfoCard 100.029.692
EC Number
  • 232-674-9
E number E460 (thickeners, ...)
KEGG
  • C00760
  • 14055602
UNII
  • SMD1X3XO9M Y
  • DTXSID3050492
Properties
(C
12
H
20
O
10
)
n
Molar mass 162.1406 g/mol per glucose unit
Appearance white powder
Density 1.5 g/cm3
Melting point 260–270 °C; 500–518 °F; 533–543 K Decomposes[2]
none
Thermochemistry
−963,000 kJ/mol[clarification needed]
−2828,000 kJ/mol[clarification needed]
Hazards
NFPA 704 (fire diamond)
Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp)[2]
REL (Recommended)
TWA 10 mg/m3 (total) TWA 5 mg/m3 (resp)[2]
IDLH (Immediate danger)
N.D.[2]
Related compounds
Related compounds
Starch
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Cellulose is mainly used to produce paperboard and paper. Smaller quantities are converted into a wide variety of derivative products such as cellophane and rayon. Conversion of cellulose from energy crops into biofuels such as cellulosic ethanol is under development as a renewable fuel source. Cellulose for industrial use is mainly obtained from wood pulp and cotton.[6]

Some animals, particularly ruminants and termites, can digest cellulose with the help of symbiotic micro-organisms that live in their guts, such as Trichonympha. In human nutrition, cellulose is a non-digestible constituent of insoluble dietary fiber, acting as a hydrophilic bulking agent for feces and potentially aiding in defecation.

History edit

Cellulose was discovered in 1838 by the French chemist Anselme Payen, who isolated it from plant matter and determined its chemical formula.[3][10][11] Cellulose was used to produce the first successful thermoplastic polymer, celluloid, by Hyatt Manufacturing Company in 1870. Production of rayon ("artificial silk") from cellulose began in the 1890s and cellophane was invented in 1912. Hermann Staudinger determined the polymer structure of cellulose in 1920. The compound was first chemically synthesized (without the use of any biologically derived enzymes) in 1992, by Kobayashi and Shoda.[12]

 
The arrangement of cellulose and other polysaccharides in a plant cell wall

Structure and properties edit

 
Cellulose under a microscope.

Cellulose has no taste, is odorless, is hydrophilic with the contact angle of 20–30 degrees,[13] is insoluble in water and most organic solvents, is chiral and is biodegradable. It was shown to melt at 467 °C in pulse tests made by Dauenhauer et al. (2016).[14] It can be broken down chemically into its glucose units by treating it with concentrated mineral acids at high temperature.[15]

Cellulose is derived from D-glucose units, which condense through β(1→4)-glycosidic bonds. This linkage motif contrasts with that for α(1→4)-glycosidic bonds present in starch and glycogen. Cellulose is a straight chain polymer. Unlike starch, no coiling or branching occurs and the molecule adopts an extended and rather stiff rod-like conformation, aided by the equatorial conformation of the glucose residues. The multiple hydroxyl groups on the glucose from one chain form hydrogen bonds with oxygen atoms on the same or on a neighbor chain, holding the chains firmly together side-by-side and forming microfibrils with high tensile strength. This confers tensile strength in cell walls where cellulose microfibrils are meshed into a polysaccharide matrix. The high tensile strength of plant stems and of the tree wood also arises from the arrangement of cellulose fibers intimately distributed into the lignin matrix. The mechanical role of cellulose fibers in the wood matrix responsible for its strong structural resistance, can somewhat be compared to that of the reinforcement bars in concrete, lignin playing here the role of the hardened cement paste acting as the "glue" in between the cellulose fibers. Mechanical properties of cellulose in primary plant cell wall are correlated with growth and expansion of plant cells.[16] Live fluorescence microscopy techniques are promising in investigation of the role of cellulose in growing plant cells.[17]

 
A triple strand of cellulose showing the hydrogen bonds (cyan lines) between glucose strands
 
Cotton fibres represent the purest natural form of cellulose, containing more than 90% of this polysaccharide.

Compared to starch, cellulose is also much more crystalline. Whereas starch undergoes a crystalline to amorphous transition when heated beyond 60–70 °C in water (as in cooking), cellulose requires a temperature of 320 °C and pressure of 25 MPa to become amorphous in water.[18]

Several types of cellulose are known. These forms are distinguished according to the location of hydrogen bonds between and within strands. Natural cellulose is cellulose I, with structures Iα and Iβ. Cellulose produced by bacteria and algae is enriched in Iα while cellulose of higher plants consists mainly of Iβ. Cellulose in regenerated cellulose fibers is cellulose II. The conversion of cellulose I to cellulose II is irreversible, suggesting that cellulose I is metastable and cellulose II is stable. With various chemical treatments it is possible to produce the structures cellulose III and cellulose IV.[19]

Many properties of cellulose depend on its chain length or degree of polymerization, the number of glucose units that make up one polymer molecule. Cellulose from wood pulp has typical chain lengths between 300 and 1700 units; cotton and other plant fibers as well as bacterial cellulose have chain lengths ranging from 800 to 10,000 units.[6] Molecules with very small chain length resulting from the breakdown of cellulose are known as cellodextrins; in contrast to long-chain cellulose, cellodextrins are typically soluble in water and organic solvents.

The chemical formula of cellulose is (C6H10O5)n where n is the degree of polymerization and represents the number of glucose groups.[20]

Plant-derived cellulose is usually found in a mixture with hemicellulose, lignin, pectin and other substances, while bacterial cellulose is quite pure, has a much higher water content and higher tensile strength due to higher chain lengths.[6]: 3384 

Cellulose consists of fibrils with crystalline and amorphous regions. These cellulose fibrils may be individualized by mechanical treatment of cellulose pulp, often assisted by chemical oxidation or enzymatic treatment, yielding semi-flexible cellulose nanofibrils generally 200 nm to 1 μm in length depending on the treatment intensity.[21] Cellulose pulp may also be treated with strong acid to hydrolyze the amorphous fibril regions, thereby producing short rigid cellulose nanocrystals a few 100 nm in length.[22] These nanocelluloses are of high technological interest due to their self-assembly into cholesteric liquid crystals,[23] production of hydrogels or aerogels,[24] use in nanocomposites with superior thermal and mechanical properties,[25] and use as Pickering stabilizers for emulsions.[26]

Processing edit

Biosynthesis edit

In plants cellulose is synthesized at the plasma membrane by rosette terminal complexes (RTCs). The RTCs are hexameric protein structures, approximately 25 nm in diameter, that contain the cellulose synthase enzymes that synthesise the individual cellulose chains.[27] Each RTC floats in the cell's plasma membrane and "spins" a microfibril into the cell wall.

RTCs contain at least three different cellulose synthases, encoded by CesA (Ces is short for "cellulose synthase") genes, in an unknown stoichiometry.[28] Separate sets of CesA genes are involved in primary and secondary cell wall biosynthesis. There are known to be about seven subfamilies in the plant CesA superfamily, some of which include the more cryptic, tentatively-named Csl (cellulose synthase-like) enzymes. These cellulose syntheses use UDP-glucose to form the β(1→4)-linked cellulose.[29]

Bacterial cellulose is produced using the same family of proteins, although the gene is called BcsA for "bacterial cellulose synthase" or CelA for "cellulose" in many instances.[30] In fact, plants acquired CesA from the endosymbiosis event that produced the chloroplast.[31] All cellulose synthases known belongs to glucosyltransferase family 2 (GT2).[30]

Cellulose synthesis requires chain initiation and elongation, and the two processes are separate. Cellulose synthase (CesA) initiates cellulose polymerization using a steroid primer, sitosterol-beta-glucoside, and UDP-glucose. It then utilizes UDP-D-glucose precursors to elongate the growing cellulose chain. A cellulase may function to cleave the primer from the mature chain.[32]

Cellulose is also synthesised by tunicate animals, particularly in the tests of ascidians (where the cellulose was historically termed "tunicine" (tunicin)).[33]

Breakdown (cellulolysis) edit

Cellulolysis is the process of breaking down cellulose into smaller polysaccharides called cellodextrins or completely into glucose units; this is a hydrolysis reaction. Because cellulose molecules bind strongly to each other, cellulolysis is relatively difficult compared to the breakdown of other polysaccharides.[34] However, this process can be significantly intensified in a proper solvent, e.g. in an ionic liquid.[35]

Most mammals have limited ability to digest dietary fiber such as cellulose. Some ruminants like cows and sheep contain certain symbiotic anaerobic bacteria (such as Cellulomonas and Ruminococcus spp.) in the flora of the rumen, and these bacteria produce enzymes called cellulases that hydrolyze cellulose. The breakdown products are then used by the bacteria for proliferation.[36] The bacterial mass is later digested by the ruminant in its digestive system (stomach and small intestine). Horses use cellulose in their diet by fermentation in their hindgut.[37] Some termites contain in their hindguts certain flagellate protozoa producing such enzymes, whereas others contain bacteria or may produce cellulase.[38]

The enzymes used to cleave the glycosidic linkage in cellulose are glycoside hydrolases including endo-acting cellulases and exo-acting glucosidases. Such enzymes are usually secreted as part of multienzyme complexes that may include dockerins and carbohydrate-binding modules.[39]

Breakdown (thermolysis) edit

At temperatures above 350 °C, cellulose undergoes thermolysis (also called 'pyrolysis'), decomposing into solid char, vapors, aerosols, and gases such as carbon dioxide.[40] Maximum yield of vapors which condense to a liquid called bio-oil is obtained at 500 °C.[41]

Semi-crystalline cellulose polymers react at pyrolysis temperatures (350–600 °C) in a few seconds; this transformation has been shown to occur via a solid-to-liquid-to-vapor transition, with the liquid (called intermediate liquid cellulose or molten cellulose) existing for only a fraction of a second.[42] Glycosidic bond cleavage produces short cellulose chains of two-to-seven monomers comprising the melt. Vapor bubbling of intermediate liquid cellulose produces aerosols, which consist of short chain anhydro-oligomers derived from the melt.[43]

Continuing decomposition of molten cellulose produces volatile compounds including levoglucosan, furans, pyrans, light oxygenates, and gases via primary reactions.[44] Within thick cellulose samples, volatile compounds such as levoglucosan undergo 'secondary reactions' to volatile products including pyrans and light oxygenates such as glycolaldehyde.[45]

Hemicellulose edit

Hemicelluloses are polysaccharides related to cellulose that comprises about 20% of the biomass of land plants. In contrast to cellulose, hemicelluloses are derived from several sugars in addition to glucose, especially xylose but also including mannose, galactose, rhamnose, and arabinose. Hemicelluloses consist of shorter chains – between 500 and 3000 sugar units.[46] Furthermore, hemicelluloses are branched, whereas cellulose is unbranched.

Regenerated cellulose edit

Cellulose is soluble in several kinds of media, several of which are the basis of commercial technologies. These dissolution processes are reversible and are used in the production of regenerated celluloses (such as viscose and cellophane) from dissolving pulp.

The most important solubilizing agent is carbon disulfide in the presence of alkali. Other agents include Schweizer's reagent, N-methylmorpholine N-oxide, and lithium chloride in dimethylacetamide. In general, these agents modify the cellulose, rendering it soluble. The agents are then removed concomitant with the formation of fibers.[47] Cellulose is also soluble in many kinds of ionic liquids.[48]

The history of regenerated cellulose is often cited as beginning with George Audemars, who first manufactured regenerated nitrocellulose fibers in 1855.[49] Although these fibers were soft and strong -resembling silk- they had the drawback of being highly flammable. Hilaire de Chardonnet perfected production of nitrocellulose fibers, but manufacturing of these fibers by his process was relatively uneconomical.[49] In 1890, L.H. Despeissis invented the cuprammonium process – which uses a cuprammonium solution to solubilize cellulose – a method still used today for production of artificial silk.[50] In 1891, it was discovered that treatment of cellulose with alkali and carbon disulfide generated a soluble cellulose derivative known as viscose.[49] This process, patented by the founders of the Viscose Development Company, is the most widely used method for manufacturing regenerated cellulose products. Courtaulds purchased the patents for this process in 1904, leading to significant growth of viscose fiber production.[51] By 1931, expiration of patents for the viscose process led to its adoption worldwide. Global production of regenerated cellulose fiber peaked in 1973 at 3,856,000 tons.[49]

Regenerated cellulose can be used to manufacture a wide variety of products. While the first application of regenerated cellulose was as a clothing textile, this class of materials is also used in the production of disposable medical devices as well as fabrication of artificial membranes.[51]

Cellulose esters and ethers edit

The hydroxyl groups (−OH) of cellulose can be partially or fully reacted with various reagents to afford derivatives with useful properties like mainly cellulose esters and cellulose ethers (−OR). In principle, although not always in current industrial practice, cellulosic polymers are renewable resources.

Ester derivatives include:

Cellulose ester Reagent Example Reagent Group R
Organic esters Organic acids Cellulose acetate Acetic acid and acetic anhydride H or −(C=O)CH3
Cellulose triacetate Acetic acid and acetic anhydride −(C=O)CH3
Cellulose propionate Propionic acid H or −(C=O)CH2CH3
Cellulose acetate propionate (CAP) Acetic acid and propanoic acid H or −(C=O)CH3 or −(C=O)CH2CH3
Cellulose acetate butyrate (CAB) Acetic acid and butyric acid H or −(C=O)CH3 or −(C=O)CH2CH2CH3
Inorganic esters Inorganic acids Nitrocellulose (cellulose nitrate) Nitric acid or another powerful nitrating agent H or −NO2
Cellulose sulfate Sulfuric acid or another powerful sulfating agent H or −SO3H

Cellulose acetate and cellulose triacetate are film- and fiber-forming materials that find a variety of uses. Nitrocellulose was initially used as an explosive and was an early film forming material. When plasticized with camphor, nitrocellulose gives celluloid.

Cellulose Ether[52] derivatives include:

Cellulose ethers Reagent Example Reagent Group R = H or Water solubility Application E number
Alkyl Halogenoalkanes Methylcellulose Chloromethane −CH3 Cold/Hot water-soluble[53] E461
Ethylcellulose Chloroethane −CH2CH3 Water-insoluble A commercial thermoplastic used in coatings, inks, binders, and controlled-release drug tablets E462
Ethyl methyl cellulose Chloromethane and chloroethane −CH3 or −CH2CH3 E465
Hydroxyalkyl Epoxides Hydroxyethyl cellulose Ethylene oxide −CH2CH2OH Cold/hot water-soluble Gelling and thickening agent
Hydroxypropyl cellulose (HPC) Propylene oxide −CH2CH(OH)CH3 Cold water-soluble E463
Hydroxyethyl methyl cellulose Chloromethane and ethylene oxide −CH3 or −CH2CH2OH Cold water-soluble Production of cellulose films
Hydroxypropyl methyl cellulose (HPMC) Chloromethane and propylene oxide −CH3 or −CH2CH(OH)CH3 Cold water-soluble Viscosity modifier, gelling, foaming and binding agent E464
Ethyl hydroxyethyl cellulose Chloroethane and ethylene oxide −CH2CH3 or −CH2CH2OH E467
Carboxyalkyl Halogenated carboxylic acids Carboxymethyl cellulose (CMC) Chloroacetic acid −CH2COOH Cold/Hot water-soluble Often used as its sodium salt, sodium carboxymethyl cellulose (NaCMC) E466

The sodium carboxymethyl cellulose can be cross-linked to give the croscarmellose sodium (E468) for use as a disintegrant in pharmaceutical formulations. Furthermore, by the covalent attachment of thiol groups to cellulose ethers such as sodium carboxymethyl cellulose, ethyl cellulose or hydroxyethyl cellulose mucoadhesive and permeation enhancing properties can be introduced.[54][55][56] Thiolated cellulose derivatives (see thiomers) exhibit also high binding properties for metal ions.[57][58]

Commercial applications edit

 
A strand of cellulose (conformation Iα), showing the hydrogen bonds (dashed) within and between cellulose molecules.

Cellulose for industrial use is mainly obtained from wood pulp and from cotton.[6]

  • Paper products: Cellulose is the major constituent of paper, paperboard, and card stock. Electrical insulation paper: Cellulose is used in diverse forms as insulation in transformers, cables, and other electrical equipment.[59]
  • Fibers: Cellulose is the main ingredient of textiles. Cotton and synthetics (nylons) each have about 40% market by volume. Other plant fibers (jute, sisal, hemp) represent about 20% of the market. Rayon, cellophane and other "regenerated cellulose fibers" are a small portion (5%).
  • Consumables: Microcrystalline cellulose (E460i) and powdered cellulose (E460ii) are used as inactive fillers in drug tablets[60] and a wide range of soluble cellulose derivatives, E numbers E461 to E469, are used as emulsifiers, thickeners and stabilizers in processed foods. Cellulose powder is, for example, used in processed cheese to prevent caking inside the package. Cellulose occurs naturally in some foods and is an additive in manufactured foods, contributing an indigestible component used for texture and bulk, potentially aiding in defecation.[61]
  • Building material: Hydroxyl bonding of cellulose in water produces a sprayable, moldable material as an alternative to the use of plastics and resins. The recyclable material can be made water- and fire-resistant. It provides sufficient strength for use as a building material.[62] Cellulose insulation made from recycled paper is becoming popular as an environmentally preferable material for building insulation. It can be treated with boric acid as a fire retardant.
  • Miscellaneous: Cellulose can be converted into cellophane, a thin transparent film. It is the base material for the celluloid that was used for photographic and movie films until the mid-1930s. Cellulose is used to make water-soluble adhesives and binders such as methyl cellulose and carboxymethyl cellulose which are used in wallpaper paste. Cellulose is further used to make hydrophilic and highly absorbent sponges. Cellulose is the raw material in the manufacture of nitrocellulose (cellulose nitrate) which is used in smokeless gunpowder.
  • Pharmaceuticals: Cellulose derivatives, such as microcrystalline cellulose (MCC), have the advantages of retaining water, being a stabilizer and thickening agent, and in reinforcement of drug tablets.[63]

Aspirational edit

Energy crops:

The major combustible component of non-food energy crops is cellulose, with lignin second. Non-food energy crops produce more usable energy than edible energy crops (which have a large starch component), but still compete with food crops for agricultural land and water resources.[64] Typical non-food energy crops include industrial hemp, switchgrass, Miscanthus, Salix (willow), and Populus (poplar) species. A strain of Clostridium bacteria found in zebra dung, can convert nearly any form of cellulose into butanol fuel.[65][66][67][68]

Another possible application is as Insect repellents.[69]

See also edit

References edit

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External links edit

  • "Cellulose" . Encyclopædia Britannica. Vol. 5 (11th ed.). 1911.
  • by Serge Pérez and William Mackie, CERMAV-CNRS
  • , by Martin Chaplin, London South Bank University
  • at the Cotton Fiber Biosciences unit of the USDA.
  • Cellulose films could provide flapping wings and cheap artificial muscles for robots – TechnologyReview.com

cellulose, organic, compound, with, formula, polysaccharide, consisting, linear, chain, several, hundred, many, thousands, linked, glucose, units, important, structural, component, primary, cell, wall, green, plants, many, forms, algae, oomycetes, some, specie. Cellulose is an organic compound with the formula C6 H10 O5 n a polysaccharide consisting of a linear chain of several hundred to many thousands of b 1 4 linked D glucose units 3 4 Cellulose is an important structural component of the primary cell wall of green plants many forms of algae and the oomycetes Some species of bacteria secrete it to form biofilms 5 Cellulose is the most abundant organic polymer on Earth 6 The cellulose content of cotton fiber is 90 that of wood is 40 50 and that of dried hemp is approximately 57 7 8 9 Cellulose 1 IdentifiersCAS Number 9004 34 6 YChEMBL ChEMBL2109009 NChemSpider NoneECHA InfoCard 100 029 692EC Number 232 674 9E number E460 thickeners KEGG C00760PubChem CID 14055602UNII SMD1X3XO9M YCompTox Dashboard EPA DTXSID3050492PropertiesChemical formula C12 H20 O10 nMolar mass 162 1406 g mol per glucose unitAppearance white powderDensity 1 5 g cm3Melting point 260 270 C 500 518 F 533 543 K Decomposes 2 Solubility in water noneThermochemistryStd enthalpy offormation DfH 298 963 000 kJ mol clarification needed Std enthalpy ofcombustion DcH 298 2828 000 kJ mol clarification needed HazardsNFPA 704 fire diamond 110NIOSH US health exposure limits PEL Permissible TWA 15 mg m3 total TWA 5 mg m3 resp 2 REL Recommended TWA 10 mg m3 total TWA 5 mg m3 resp 2 IDLH Immediate danger N D 2 Related compoundsRelated compounds StarchExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Cellulose is mainly used to produce paperboard and paper Smaller quantities are converted into a wide variety of derivative products such as cellophane and rayon Conversion of cellulose from energy crops into biofuels such as cellulosic ethanol is under development as a renewable fuel source Cellulose for industrial use is mainly obtained from wood pulp and cotton 6 Some animals particularly ruminants and termites can digest cellulose with the help of symbiotic micro organisms that live in their guts such as Trichonympha In human nutrition cellulose is a non digestible constituent of insoluble dietary fiber acting as a hydrophilic bulking agent for feces and potentially aiding in defecation Contents 1 History 2 Structure and properties 3 Processing 3 1 Biosynthesis 3 2 Breakdown cellulolysis 3 3 Breakdown thermolysis 4 Hemicellulose 5 Regenerated cellulose 6 Cellulose esters and ethers 7 Commercial applications 7 1 Aspirational 8 See also 9 References 10 External linksHistory editCellulose was discovered in 1838 by the French chemist Anselme Payen who isolated it from plant matter and determined its chemical formula 3 10 11 Cellulose was used to produce the first successful thermoplastic polymer celluloid by Hyatt Manufacturing Company in 1870 Production of rayon artificial silk from cellulose began in the 1890s and cellophane was invented in 1912 Hermann Staudinger determined the polymer structure of cellulose in 1920 The compound was first chemically synthesized without the use of any biologically derived enzymes in 1992 by Kobayashi and Shoda 12 nbsp The arrangement of cellulose and other polysaccharides in a plant cell wallStructure and properties edit nbsp Cellulose under a microscope Cellulose has no taste is odorless is hydrophilic with the contact angle of 20 30 degrees 13 is insoluble in water and most organic solvents is chiral and is biodegradable It was shown to melt at 467 C in pulse tests made by Dauenhauer et al 2016 14 It can be broken down chemically into its glucose units by treating it with concentrated mineral acids at high temperature 15 Cellulose is derived from D glucose units which condense through b 1 4 glycosidic bonds This linkage motif contrasts with that for a 1 4 glycosidic bonds present in starch and glycogen Cellulose is a straight chain polymer Unlike starch no coiling or branching occurs and the molecule adopts an extended and rather stiff rod like conformation aided by the equatorial conformation of the glucose residues The multiple hydroxyl groups on the glucose from one chain form hydrogen bonds with oxygen atoms on the same or on a neighbor chain holding the chains firmly together side by side and forming microfibrils with high tensile strength This confers tensile strength in cell walls where cellulose microfibrils are meshed into a polysaccharide matrix The high tensile strength of plant stems and of the tree wood also arises from the arrangement of cellulose fibers intimately distributed into the lignin matrix The mechanical role of cellulose fibers in the wood matrix responsible for its strong structural resistance can somewhat be compared to that of the reinforcement bars in concrete lignin playing here the role of the hardened cement paste acting as the glue in between the cellulose fibers Mechanical properties of cellulose in primary plant cell wall are correlated with growth and expansion of plant cells 16 Live fluorescence microscopy techniques are promising in investigation of the role of cellulose in growing plant cells 17 nbsp A triple strand of cellulose showing the hydrogen bonds cyan lines between glucose strands nbsp Cotton fibres represent the purest natural form of cellulose containing more than 90 of this polysaccharide Compared to starch cellulose is also much more crystalline Whereas starch undergoes a crystalline to amorphous transition when heated beyond 60 70 C in water as in cooking cellulose requires a temperature of 320 C and pressure of 25 MPa to become amorphous in water 18 Several types of cellulose are known These forms are distinguished according to the location of hydrogen bonds between and within strands Natural cellulose is cellulose I with structures Ia and Ib Cellulose produced by bacteria and algae is enriched in Ia while cellulose of higher plants consists mainly of Ib Cellulose in regenerated cellulose fibers is cellulose II The conversion of cellulose I to cellulose II is irreversible suggesting that cellulose I is metastable and cellulose II is stable With various chemical treatments it is possible to produce the structures cellulose III and cellulose IV 19 Many properties of cellulose depend on its chain length or degree of polymerization the number of glucose units that make up one polymer molecule Cellulose from wood pulp has typical chain lengths between 300 and 1700 units cotton and other plant fibers as well as bacterial cellulose have chain lengths ranging from 800 to 10 000 units 6 Molecules with very small chain length resulting from the breakdown of cellulose are known as cellodextrins in contrast to long chain cellulose cellodextrins are typically soluble in water and organic solvents The chemical formula of cellulose is C6H10O5 n where n is the degree of polymerization and represents the number of glucose groups 20 Plant derived cellulose is usually found in a mixture with hemicellulose lignin pectin and other substances while bacterial cellulose is quite pure has a much higher water content and higher tensile strength due to higher chain lengths 6 3384 Cellulose consists of fibrils with crystalline and amorphous regions These cellulose fibrils may be individualized by mechanical treatment of cellulose pulp often assisted by chemical oxidation or enzymatic treatment yielding semi flexible cellulose nanofibrils generally 200 nm to 1 mm in length depending on the treatment intensity 21 Cellulose pulp may also be treated with strong acid to hydrolyze the amorphous fibril regions thereby producing short rigid cellulose nanocrystals a few 100 nm in length 22 These nanocelluloses are of high technological interest due to their self assembly into cholesteric liquid crystals 23 production of hydrogels or aerogels 24 use in nanocomposites with superior thermal and mechanical properties 25 and use as Pickering stabilizers for emulsions 26 Processing editBiosynthesis edit In plants cellulose is synthesized at the plasma membrane by rosette terminal complexes RTCs The RTCs are hexameric protein structures approximately 25 nm in diameter that contain the cellulose synthase enzymes that synthesise the individual cellulose chains 27 Each RTC floats in the cell s plasma membrane and spins a microfibril into the cell wall RTCs contain at least three different cellulose synthases encoded by CesA Ces is short for cellulose synthase genes in an unknown stoichiometry 28 Separate sets of CesA genes are involved in primary and secondary cell wall biosynthesis There are known to be about seven subfamilies in the plant CesA superfamily some of which include the more cryptic tentatively named Csl cellulose synthase like enzymes These cellulose syntheses use UDP glucose to form the b 1 4 linked cellulose 29 Bacterial cellulose is produced using the same family of proteins although the gene is called BcsA for bacterial cellulose synthase or CelA for cellulose in many instances 30 In fact plants acquired CesA from the endosymbiosis event that produced the chloroplast 31 All cellulose synthases known belongs to glucosyltransferase family 2 GT2 30 Cellulose synthesis requires chain initiation and elongation and the two processes are separate Cellulose synthase CesA initiates cellulose polymerization using a steroid primer sitosterol beta glucoside and UDP glucose It then utilizes UDP D glucose precursors to elongate the growing cellulose chain A cellulase may function to cleave the primer from the mature chain 32 Cellulose is also synthesised by tunicate animals particularly in the tests of ascidians where the cellulose was historically termed tunicine tunicin 33 Breakdown cellulolysis edit Cellulolysis is the process of breaking down cellulose into smaller polysaccharides called cellodextrins or completely into glucose units this is a hydrolysis reaction Because cellulose molecules bind strongly to each other cellulolysis is relatively difficult compared to the breakdown of other polysaccharides 34 However this process can be significantly intensified in a proper solvent e g in an ionic liquid 35 Most mammals have limited ability to digest dietary fiber such as cellulose Some ruminants like cows and sheep contain certain symbiotic anaerobic bacteria such as Cellulomonas and Ruminococcus spp in the flora of the rumen and these bacteria produce enzymes called cellulases that hydrolyze cellulose The breakdown products are then used by the bacteria for proliferation 36 The bacterial mass is later digested by the ruminant in its digestive system stomach and small intestine Horses use cellulose in their diet by fermentation in their hindgut 37 Some termites contain in their hindguts certain flagellate protozoa producing such enzymes whereas others contain bacteria or may produce cellulase 38 The enzymes used to cleave the glycosidic linkage in cellulose are glycoside hydrolases including endo acting cellulases and exo acting glucosidases Such enzymes are usually secreted as part of multienzyme complexes that may include dockerins and carbohydrate binding modules 39 Breakdown thermolysis edit See also Wood ash Composition At temperatures above 350 C cellulose undergoes thermolysis also called pyrolysis decomposing into solid char vapors aerosols and gases such as carbon dioxide 40 Maximum yield of vapors which condense to a liquid called bio oil is obtained at 500 C 41 Semi crystalline cellulose polymers react at pyrolysis temperatures 350 600 C in a few seconds this transformation has been shown to occur via a solid to liquid to vapor transition with the liquid called intermediate liquid cellulose or molten cellulose existing for only a fraction of a second 42 Glycosidic bond cleavage produces short cellulose chains of two to seven monomers comprising the melt Vapor bubbling of intermediate liquid cellulose produces aerosols which consist of short chain anhydro oligomers derived from the melt 43 Continuing decomposition of molten cellulose produces volatile compounds including levoglucosan furans pyrans light oxygenates and gases via primary reactions 44 Within thick cellulose samples volatile compounds such as levoglucosan undergo secondary reactions to volatile products including pyrans and light oxygenates such as glycolaldehyde 45 Hemicellulose editMain article Hemicellulose Hemicelluloses are polysaccharides related to cellulose that comprises about 20 of the biomass of land plants In contrast to cellulose hemicelluloses are derived from several sugars in addition to glucose especially xylose but also including mannose galactose rhamnose and arabinose Hemicelluloses consist of shorter chains between 500 and 3000 sugar units 46 Furthermore hemicelluloses are branched whereas cellulose is unbranched Regenerated cellulose editCellulose is soluble in several kinds of media several of which are the basis of commercial technologies These dissolution processes are reversible and are used in the production of regenerated celluloses such as viscose and cellophane from dissolving pulp The most important solubilizing agent is carbon disulfide in the presence of alkali Other agents include Schweizer s reagent N methylmorpholine N oxide and lithium chloride in dimethylacetamide In general these agents modify the cellulose rendering it soluble The agents are then removed concomitant with the formation of fibers 47 Cellulose is also soluble in many kinds of ionic liquids 48 The history of regenerated cellulose is often cited as beginning with George Audemars who first manufactured regenerated nitrocellulose fibers in 1855 49 Although these fibers were soft and strong resembling silk they had the drawback of being highly flammable Hilaire de Chardonnet perfected production of nitrocellulose fibers but manufacturing of these fibers by his process was relatively uneconomical 49 In 1890 L H Despeissis invented the cuprammonium process which uses a cuprammonium solution to solubilize cellulose a method still used today for production of artificial silk 50 In 1891 it was discovered that treatment of cellulose with alkali and carbon disulfide generated a soluble cellulose derivative known as viscose 49 This process patented by the founders of the Viscose Development Company is the most widely used method for manufacturing regenerated cellulose products Courtaulds purchased the patents for this process in 1904 leading to significant growth of viscose fiber production 51 By 1931 expiration of patents for the viscose process led to its adoption worldwide Global production of regenerated cellulose fiber peaked in 1973 at 3 856 000 tons 49 Regenerated cellulose can be used to manufacture a wide variety of products While the first application of regenerated cellulose was as a clothing textile this class of materials is also used in the production of disposable medical devices as well as fabrication of artificial membranes 51 Cellulose esters and ethers editThe hydroxyl groups OH of cellulose can be partially or fully reacted with various reagents to afford derivatives with useful properties like mainly cellulose esters and cellulose ethers OR In principle although not always in current industrial practice cellulosic polymers are renewable resources Ester derivatives include Cellulose ester Reagent Example Reagent Group ROrganic esters Organic acids Cellulose acetate Acetic acid and acetic anhydride H or C O CH3Cellulose triacetate Acetic acid and acetic anhydride C O CH3Cellulose propionate Propionic acid H or C O CH2CH3Cellulose acetate propionate CAP Acetic acid and propanoic acid H or C O CH3 or C O CH2CH3Cellulose acetate butyrate CAB Acetic acid and butyric acid H or C O CH3 or C O CH2CH2CH3Inorganic esters Inorganic acids Nitrocellulose cellulose nitrate Nitric acid or another powerful nitrating agent H or NO2Cellulose sulfate Sulfuric acid or another powerful sulfating agent H or SO3HCellulose acetate and cellulose triacetate are film and fiber forming materials that find a variety of uses Nitrocellulose was initially used as an explosive and was an early film forming material When plasticized with camphor nitrocellulose gives celluloid Cellulose Ether 52 derivatives include Cellulose ethers Reagent Example Reagent Group R H or Water solubility Application E numberAlkyl Halogenoalkanes Methylcellulose Chloromethane CH3 Cold Hot water soluble 53 E461Ethylcellulose Chloroethane CH2CH3 Water insoluble A commercial thermoplastic used in coatings inks binders and controlled release drug tablets E462Ethyl methyl cellulose Chloromethane and chloroethane CH3 or CH2CH3 E465Hydroxyalkyl Epoxides Hydroxyethyl cellulose Ethylene oxide CH2CH2OH Cold hot water soluble Gelling and thickening agentHydroxypropyl cellulose HPC Propylene oxide CH2CH OH CH3 Cold water soluble E463Hydroxyethyl methyl cellulose Chloromethane and ethylene oxide CH3 or CH2CH2OH Cold water soluble Production of cellulose filmsHydroxypropyl methyl cellulose HPMC Chloromethane and propylene oxide CH3 or CH2CH OH CH3 Cold water soluble Viscosity modifier gelling foaming and binding agent E464Ethyl hydroxyethyl cellulose Chloroethane and ethylene oxide CH2CH3 or CH2CH2OH E467Carboxyalkyl Halogenated carboxylic acids Carboxymethyl cellulose CMC Chloroacetic acid CH2COOH Cold Hot water soluble Often used as its sodium salt sodium carboxymethyl cellulose NaCMC E466The sodium carboxymethyl cellulose can be cross linked to give the croscarmellose sodium E468 for use as a disintegrant in pharmaceutical formulations Furthermore by the covalent attachment of thiol groups to cellulose ethers such as sodium carboxymethyl cellulose ethyl cellulose or hydroxyethyl cellulose mucoadhesive and permeation enhancing properties can be introduced 54 55 56 Thiolated cellulose derivatives see thiomers exhibit also high binding properties for metal ions 57 58 Commercial applications edit nbsp A strand of cellulose conformation Ia showing the hydrogen bonds dashed within and between cellulose molecules See also dissolving pulp and pulp paper Cellulose for industrial use is mainly obtained from wood pulp and from cotton 6 Paper products Cellulose is the major constituent of paper paperboard and card stock Electrical insulation paper Cellulose is used in diverse forms as insulation in transformers cables and other electrical equipment 59 Fibers Cellulose is the main ingredient of textiles Cotton and synthetics nylons each have about 40 market by volume Other plant fibers jute sisal hemp represent about 20 of the market Rayon cellophane and other regenerated cellulose fibers are a small portion 5 Consumables Microcrystalline cellulose E460i and powdered cellulose E460ii are used as inactive fillers in drug tablets 60 and a wide range of soluble cellulose derivatives E numbers E461 to E469 are used as emulsifiers thickeners and stabilizers in processed foods Cellulose powder is for example used in processed cheese to prevent caking inside the package Cellulose occurs naturally in some foods and is an additive in manufactured foods contributing an indigestible component used for texture and bulk potentially aiding in defecation 61 Building material Hydroxyl bonding of cellulose in water produces a sprayable moldable material as an alternative to the use of plastics and resins The recyclable material can be made water and fire resistant It provides sufficient strength for use as a building material 62 Cellulose insulation made from recycled paper is becoming popular as an environmentally preferable material for building insulation It can be treated with boric acid as a fire retardant Miscellaneous Cellulose can be converted into cellophane a thin transparent film It is the base material for the celluloid that was used for photographic and movie films until the mid 1930s Cellulose is used to make water soluble adhesives and binders such as methyl cellulose and carboxymethyl cellulose which are used in wallpaper paste Cellulose is further used to make hydrophilic and highly absorbent sponges Cellulose is the raw material in the manufacture of nitrocellulose cellulose nitrate which is used in smokeless gunpowder Pharmaceuticals Cellulose derivatives such as microcrystalline cellulose MCC have the advantages of retaining water being a stabilizer and thickening agent and in reinforcement of drug tablets 63 Aspirational editEnergy crops Main article Energy cropThe major combustible component of non food energy crops is cellulose with lignin second Non food energy crops produce more usable energy than edible energy crops which have a large starch component but still compete with food crops for agricultural land and water resources 64 Typical non food energy crops include industrial hemp switchgrass Miscanthus Salix willow and Populus poplar species A strain of Clostridium bacteria found in zebra dung can convert nearly any form of cellulose into butanol fuel 65 66 67 68 Another possible application is as Insect repellents 69 See also editGluconic acid Isosaccharinic acid a degradation product of cellulose Lignin ZeoformReferences edit Nishiyama Yoshiharu Langan Paul Chanzy Henri 2002 Crystal Structure and Hydrogen Bonding System in Cellulose Ib from Synchrotron X ray and Neutron Fiber Diffraction J Am Chem Soc 124 31 9074 9082 doi 10 1021 ja0257319 PMID 12149011 a b c d NIOSH Pocket Guide to Chemical Hazards 0110 National Institute for Occupational Safety and Health NIOSH a b Crawford R L 1981 Lignin biodegradation and transformation New York John Wiley and Sons ISBN 978 0 471 05743 7 Updegraff D M 1969 Semimicro determination of cellulose in biological materials Analytical Biochemistry 32 3 420 424 doi 10 1016 S0003 2697 69 80009 6 PMID 5361396 Romeo Tony 2008 Bacterial biofilms Berlin Springer pp 258 263 ISBN 978 3 540 75418 3 a b c d e Klemm Dieter Heublein Brigitte Fink Hans Peter Bohn Andreas 2005 Cellulose Fascinating Biopolymer and Sustainable Raw Material Angew Chem Int Ed 44 22 3358 3393 doi 10 1002 anie 200460587 PMID 15861454 Cellulose 2008 In Encyclopaedia Britannica Retrieved January 11 2008 from Encyclopaedia Britannica Online Chemical Composition of Wood Archived 2018 10 13 at the Wayback Machine ipst gatech edu Piotrowski Stephan and Carus Michael May 2011 Multi criteria evaluation of lignocellulosic niche crops for use in biorefinery processes Archived 2021 04 03 at the Wayback Machine nova Institut GmbH Hurth Germany Payen A 1838 Memoire sur la composition du tissu propre des plantes et du ligneux Memoir on the composition of the tissue of plants and of woody material Comptes rendus vol 7 pp 1052 1056 Payen added appendices to this paper on December 24 1838 see Comptes rendus vol 8 p 169 1839 and on February 4 1839 see Comptes rendus vol 9 p 149 1839 A committee of the French Academy of Sciences reviewed Payen s findings in Jean Baptiste Dumas 1839 Rapport sur un memoire de M Payen reltes rendus vol 8 pp 51 53 In this report the word cellulose is coined and author points out the similarity between the empirical 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