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Cellulose
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
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
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
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 investigation as an alternative fuel source. Cellulose
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 Assay 3.2 Biosynthesis 3.3 Breakdown (cellulolysis) 3.4 Breakdown (thermolysis)

4 Hemicellulose 5 Derivatives 6 Applications 7 See also 8 References 9 External links

History[edit] Cellulose
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
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
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
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
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
Cellulose
produced by bacteria and algae is enriched in Iα while cellulose of higher plants consists mainly of Iβ. Cellulose
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
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. 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
Cellulose
is soluble in Schweizer's reagent, cupriethylenediamine (CED), cadmiumethylenediamine (Cadoxen), N-methylmorpholine N-oxide, and lithium chloride / dimethylacetamide.[18] This is used in the production of regenerated celluloses (such as viscose and cellophane) from dissolving pulp. Cellulose
Cellulose
is also soluble in many kinds of ionic liquids.[19] Cellulose
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.[20] Recently, nanocrystalline cellulose was used as the filler phase in bio-based polymer matrices to produce nanocomposites with superior thermal and mechanical properties.[21] 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
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.[22] 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.[23] 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.[24] 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.[25] Cellulose
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.[26] Cellulose
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
Cellulose
is also synthesised by animals, particularly in the tests of ascidians (where the cellulose was historically termed "tunicine") although it is also a minor component of mammalian connective tissue.[27] 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.[28] However, this process can be significantly intensified in a proper solvent, e.g. in an ionic liquid.[29] 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.[30] 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.[31] 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.[32] Maximum yield of vapors which condense to a liquid called bio-oil is obtained at 500 °C.[33] 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.[34] Glycosidic bond
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.[35] Continuing decomposition of molten cellulose produces volatile compounds including levoglucosan, furans, pyrans, light oxygenates and gases via primary reactions.[36] Within thick cellulose samples, volatile compounds such as levoglucosan undergo ‘secondary reactions’ to volatile products including pyrans and light oxygenates such as glycolaldehyde.[37] Hemicellulose[edit] Main article: Hemicellulose 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
Hemicellulose
consists of shorter chains – between 500 and 3000 sugar units.[38] 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
Ester
derivatives include:

Cellulose
Cellulose
ester Reagent Example Reagent Group R

Organic esters Organic acids Cellulose
Cellulose
acetate Acetic acid
Acetic acid
and acetic anhydride H or -(C=O)CH3

Cellulose
Cellulose
triacetate Acetic acid
Acetic acid
and acetic anhydride -(C=O)CH3

Cellulose
Cellulose
propionate Propionic acid H or -(C=O)CH2CH3

Cellulose acetate
Cellulose acetate
propionate (CAP) Acetic acid
Acetic acid
and propanoic acid H or -(C=O)CH3 or -(C=O)CH2CH3

Cellulose acetate
Cellulose acetate
butyrate (CAB) Acetic acid
Acetic acid
and butyric acid H or -(C=O)CH3 or -(C=O)CH2CH2CH3

Inorganic esters Inorganic acids Nitrocellulose
Nitrocellulose
(cellulose nitrate) Nitric acid
Nitric acid
or another powerful nitrating agent H or -NO2

Cellulose
Cellulose
sulfate Sulfuric acid
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
Ether
derivatives include:

Cellulose
Cellulose
ethers Reagent Example Reagent Group R = H or Water
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
Chloromethane
and chloroethane -CH3 or -CH2CH3

E465

Hydroxyalkyl Epoxides Hydroxyethyl cellulose Ethylene oxide -CH2CH2OH Cold/hot water-soluble Gelling and thickening agent

Hydroxypropyl cellulose
Hydroxypropyl cellulose
(HPC) Propylene oxide -CH2CH(OH)CH3 Cold water-soluble

E463

Hydroxyethyl methyl cellulose Chloromethane
Chloromethane
and ethylene oxide -CH3 or -CH2CH2OH Cold water-soluble Production of cellulose films

Hydroxypropyl methyl cellulose
Hydroxypropyl methyl cellulose
(HPMC) Chloromethane
Chloromethane
and propylene oxide -CH3 or -CH2CH(OH)CH3 Cold water-soluble Viscosity modifier, gelling, foaming and binding agent E464

Ethyl hydroxyethyl cellulose Chloroethane
Chloroethane
and ethylene oxide -CH2CH3 or—CH2CH2OH

E467

Carboxyalkyl Halogenated carboxylic acids Carboxymethyl cellulose
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)

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Cellulose
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
Paper
products: Cellulose
Cellulose
is the major constituent of paper, paperboard, and card stock. Fibers: Cellulose
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
Lyocell
process. Consumables: Microcrystalline cellulose (E460i) and powdered cellulose (E460ii) are used as inactive fillers in drug tablets[39] and a wide range of soluble cellulose derivatives, E numbers E461 to E469, are used as emulsifiers, thickeners and stabilizers in processed foods. Cellulose
Cellulose
powder is, for example, used in Parmesan cheese to prevent caking inside the package. Cellulose
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.[40] Science: Cellulose
Cellulose
is used in the laboratory as a stationary phase for thin layer chromatography. Cellulose
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.[41] Typical non-food energy crops include industrial hemp (though outlawed in some countries), switchgrass, Miscanthus, Salix (willow), and Populus
Populus
(poplar) species. Biofuel: TU-103, a strain of Clostridium
Clostridium
bacteria found in zebra waste, can convert nearly any form of cellulose into butanol fuel.[42][43] Building material: Hydroxyl
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.[44] Cellulose insulation
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
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
Cellulose
is further used to make hydrophilic and highly absorbent sponges. Cellulose
Cellulose
is the raw material in the manufacture of nitrocellulose (cellulose nitrate) which is used in smokeless gunpowder.

See also[edit]

Microbial cellulose Zeoform

References[edit]

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External links[edit]

 "Cellulose". Encyclopædia Britannica. 5 (11th ed.). 1911.  Structure and morphology of cellulose by Serge Pérez and William Mackie, CERMAV-CNRS Cellulose, by Martin Chaplin, London South Bank University Clear description of a cellulose assay method at the Cotton
Cotton
Fiber Biosciences unit of the USDA. Cellulose
Cellulose
films could provide flapping wings and cheap artificial muscles for robots – TechnologyReview.com CDC - NIOSH Pocket Guide to Chemical Hazards - Cellulose

v t e

Types of carbohydrates

General

Aldose Ketose Furanose Pyranose

Geometry

Anomer Cyclohexane conformation Mutarotation

Monosaccharides

Dioses

Aldodiose

Glycolaldehyde

Trioses

Aldotriose

Glyceraldehyde

Ketotriose

Dihydroxyacetone

Tetroses

Aldotetroses

Erythrose Threose

Ketotetrose

Erythrulose

Pentoses

Aldopentoses

Arabinose Lyxose Ribose Xylose

Ketopentoses

Ribulose Xylulose

Deoxy sugars

Deoxyribose

Hexoses

Aldohexoses

Allose Altrose Galactose Glucose Gulose Idose Mannose Talose

Ketohexoses

Fructose Psicose Sorbose Tagatose

Deoxy sugars

Fucose Fuculose Rhamnose

Heptoses

Ketoheptoses

Mannoheptulose Sedoheptulose

Above 7

Octoses Nonoses

Neuraminic acid

Multiple

Disaccharides

Cellobiose Isomaltose Isomaltulose Lactose Lactulose Maltose Sucrose Trehalose Turanose

Trisaccharides

Maltotriose Melezitose Raffinose

Tetrasaccharides

Stachyose

Other oligosaccharides

Acarbose Fructooligosaccharide (FOS) Galactooligosaccharide
Galactooligosaccharide
(GOS) Isomaltooligosaccharide (IMO) Maltodextrin Mannan-oligosaccharides (MOS)

Polysaccharides

Beta-glucan

Oat beta-glucan Lentinan Sizofiran Zymosan Cellulose Chitin

Chitosan Dextrin
Dextrin
/ Dextran Fructose
Fructose
/ Fructan

Inulin

Galactose
Galactose
/ Galactan Glucose
Glucose
/ Glucan

Glycogen

Hemicellulose Levan beta 2→6 Lignin Mannan Pectin Starch

Amylopectin Amylose

Xanthan gum

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Paper

History Manufacture/Papermaking

Types

Bible Blotting Bond Cardboard Cartridge Coated paper Construction Cotton
Cotton
(rag) Crêpe Display Dó Asphalt Glassine India Korean Kraft Laid Manila Newsprint Oatmeal Onionskin Origami Baking Building Rice Rolling Scritta Paperboard Security Seed Copy Stone Tar Thermal Tissue Tracing Transfer Tree-free Wallpaper Washi Waterproof Wax Wood-free Wove Writing Xuan

Materials

China clay Fiber crop Paper
Paper
chemicals Papyrus Wood
Wood
pulp

Specifications

Grammage Density Paper
Paper
sizes Units of paper quantity Surface chemistry of paper Wet strength

Manufacture and process

Bleaching of wood pulp Calender Conical refiner Deinking Paper
Paper
pollution Environmental impact of paper Handmade paper Hollander beater Kraft process Organosolv Paper
Paper
machine Paper
Paper
recycling Papermaking Soda pulping Sulfite process

Industry

Paper
Paper
industry In Europe In Canada In India In Japan In the United States Paper
Paper
mill List of paper mills

  Category:Paper   Commons

v t e

Wood
Wood
products

Lumber/ timber

Batten Beam Bressummer Cruck Flitch beam Flooring Joist Lath Molding Panelling Plank Plate Post Purlin Rafter Railroad ties Reclaimed Shingle Siding Sill Stud Timber truss Treenail Truss Utility pole

Engineered wood

Glued laminated timber

veneer LVL parallel strand

I-joist Fiberboard

hardboard Masonite MDF

Oriented strand board Oriented structural straw board Particle board Plywood Structural insulated panel Wood-plastic composite

lumber

Fuelwood

Charcoal

biochar

Firelog Firewood Pellet fuel Wood
Wood
fuel

Fibers

Cardboard Corrugated fiberboard Paper Paperboard Pulp Pulpwood Rayon

Derivatives

Birch-tar Cellulose

nano

Hemicellulose Cellulosic ethanol Dyes Lignin Liquid smoke Lye Methanol Pyroligneous acid Pine tar Pitch Sandalwood oil Tannin Wood
Wood
gas

By-products

Barkdust Black liquor Ramial chipped wood Sawdust Tall oil Wood
Wood
flour Wood
Wood
wool Woodchips

Historical

Axe ties Clapboard Dugout canoe Potash Sawdust
Sawdust
brandy Split-rail fence Tanbark Timber framing Wooden masts

See also

Biomass Certified wood Destructive distillation Dry distillation Engineered bamboo Forestry List of woods Mulch Non-timber forest products Papermaking Wood
Wood
drying Wood
Wood
preservation Wood
Wood
processing Woodworking

Forestry
Forestry
portal Trees portal Category Commons WikiProject Forestry

Authority control

GND: 4147454-5 N