Cellulose

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Cellulose[1]
Cellulose, a linear polymer of D-glucose units (two are shown) linked by β(1→4)-glycosidic bonds.
Three-dimensional structure of cellulose
Identifiers
ChEMBL
ChemSpider
  • None
ECHA InfoCard 100.029.692
EC Number 232-674-9
E number E460 (thickeners, ...)
UNII
Properties
(C
6H
10O
5)
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 J/mol
−2828,000 J/mol
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
US health exposure limits (NIOSH):
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 ☑Y☒N ?)
Infobox references

Cellulose is an organic compound with the formula (C
6H
10O
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 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 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 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.

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.[16]

Several different crystalline structures of cellulose are known, corresponding 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.[17]

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.

Cellulose contains 44.44% carbon, 6.17% hydrogen, and 49.39% oxygen. The chemical formula of cellulose is (C6H10O5)n where n is the degree of polymerization and represents the number of glucose groups.[18]

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 is soluble in Schweizer's reagent, cupriethylenediamine (CED), cadmiumethylenediamine (Cadoxen), N-methylmorpholine N-oxide, and lithium chloride / dimethylacetamide.[19] This is used in the production of regenerated celluloses (such as viscose and cellophane) from dissolving pulp. Cellulose is also soluble in many kinds of ionic liquids.[20]

Cellulose consists of crystalline and amorphous regions. By treating it with strong acid, the amorphous regions can be broken up, thereby producing nanocrystalline cellulose, a novel material with many desirable properties.[21] Recently, nanocrystalline cellulose was used as the filler phase in bio-based polymer matrices to produce nanocomposites with superior thermal and mechanical properties.[22]

Processing[edit]

Assay[edit]

Given a cellulose-containing material, the carbohydrate portion that does not dissolve in a 17.5% solution of sodium hydroxide at 20 °C is α cellulose, which is true cellulose.[clarification needed] Acidification of the extract precipitates β cellulose. The portion that dissolves in base but does not precipitate with acid is γ cellulose.[citation needed]

Cellulose can be assayed using a method described by Updegraff in 1969, where the fiber is dissolved in acetic and nitric acid to remove lignin, hemicellulose, and xylosans. The resulting cellulose is allowed to react with anthrone in sulfuric acid. The resulting coloured compound is assayed spectrophotometrically at a wavelength of approximately 635 nm.

In addition, cellulose is represented by the difference between acid detergent fiber (ADF) and acid detergent lignin (ADL).

Luminescent conjugated oligothiophenes can also be used to detect cellulose using fluorescence microscopy or spectrofluorometric methods.[23]

Biosynthesis[edit]

In vascular 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.[24] 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 genes, in an unknown stoichiometry.[25] Separate sets of CesA genes are involved in primary and secondary cell wall biosynthesis. There are known to be about seven subfamilies in the CesA superfamily. These cellulose synthases use UDP-glucose to form the β(1→4)-linked cellulose.[26]

Cellulose synthesis requires chain initiation and elongation, and the two processes are separate. CesA glucosyltransferase initiates cellulose polymerization using a steroid primer, sitosterol-beta-glucoside, and UDP-glucose.[27] Cellulose synthase utilizes UDP-D-glucose precursors to elongate the growing cellulose chain. A cellulase may function to cleave the primer from the mature chain.

Cellulose is also synthesised by tunicate animals, particularly in the tests of ascidians (where the cellulose was historically termed "tunicine" (tunicin)).[28]

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.[29] However, this process can be significantly intensified in a proper solvent, e.g. in an ionic liquid.[30]

Most mammals have limited ability to digest dietary fiber such as cellulose. Some ruminants like cows and sheep contain certain symbiotic anaerobic bacteria (like Cellulomonas) in the flora of the rumen, and these bacteria produce enzymes called cellulases that help the microorganism to digest cellulose; the breakdown products are then used by the bacteria for proliferation. 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 via symbiotic bacteria which produce cellulase to digest cellulose.[citation needed] Similarly, some termites contain in their hindguts certain flagellate protozoa producing such enzymes, whereas others contain bacteria or may produce cellulase.[31]

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.[32]

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.[33] Maximum yield of vapors which condense to a liquid called bio-oil is obtained at 500 °C.[34]

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.[35] 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.[36]

Continuing decomposition of molten cellulose produces volatile compounds including levoglucosan, furans, pyrans, light oxygenates and gases via primary reactions.[37] Within thick cellulose samples, volatile compounds such as levoglucosan undergo ‘secondary reactions’ to volatile products including pyrans and light oxygenates such as glycolaldehyde.[38]

Hemicellulose[edit]

Main article: Hemicellulose

Hemicellulose is a polysaccharide related to cellulose that comprises about 20% of the biomass of most plants. In contrast to cellulose, hemicellulose is derived from several sugars in addition to glucose, especially xylose but also including mannose, galactose, rhamnose, and arabinose. Hemicellulose consists of shorter chains – between 500 and 3000 sugar units.[39] Furthermore, hemicellulose is branched, whereas cellulose is unbranched.

Derivatives[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, though 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 sulfuring agent H or -SO3H

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

Ether derivatives include:

Cellulose ethers Reagent Example Reagent Group R = H or Water solubility Application E number
Alkyl Halogenoalkanes Methylcellulose Chloromethane -CH3 Cold water-soluble 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.

Applications[edit]

A strand of cellulose (conformation Iα), 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 cotton.[6] The kraft process is used to separate cellulose from lignin, another major component of plant matter.

  • Paper products: Cellulose is the major constituent of paper, paperboard, and card stock.
  • Fibers: Cellulose is the main ingredient of textiles made from cotton, linen, and other plant fibers. It can be turned into rayon, an important fiber that has been used for textiles since the beginning of the 20th century. Both cellophane and rayon are known as "regenerated cellulose fibers"; they are identical to cellulose in chemical structure and are usually made from dissolving pulp via viscose. A more recent and environmentally friendly method to produce a form of rayon is the Lyocell process.
  • Consumables: Microcrystalline cellulose (E460i) and powdered cellulose (E460ii) are used as inactive fillers in drug tablets[40] 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 Parmesan 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.[41]
  • Science: Cellulose is used in the laboratory as a stationary phase for thin layer chromatography. Cellulose fibers are also used in liquid filtration, sometimes in combination with diatomaceous earth or other filtration media, to create a filter bed of inert material.
  • Energy crops:
    Main article: Energy crop
    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.[42] Typical non-food energy crops include industrial hemp (though outlawed in some countries), switchgrass, Miscanthus, Salix (willow), and Populus (poplar) species.
  • Biofuel: TU-103, a strain of Clostridium bacteria found in zebra waste, can convert nearly any form of cellulose into butanol fuel.[43][44]
  • 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.[45] 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.[46]

See also[edit]

References[edit]

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External links[edit]

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