Cellulose - Wikipedia

14/10/2020 Cellulose - Wikipedia
Cellulose
Cellulose is an organic compound with the formula (C6H10O5)n, a
polysaccharide consisting of a linear chain of several hundred to many Cellulose[1]
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 Identifiers
obtained from wood pulp and cotton.[6] CAS Number 9004-34-6 (http://www.
commonchemistry.org/
Some animals, particularly ruminants and termites, can digest
cellulose with the help of symbiotic micro-organisms that live in their ChemicalDetail.aspx?r
guts, such as Trichonympha. In human nutrition, cellulose is a non- ef=9004-34-6)
digestible constituent of insoluble dietary fiber, acting as a hydrophilic ChEMBL ChEMBL2109009 (http
bulking agent for feces and potentially aiding in defecation.
s://www.ebi.ac.uk/chem
bldb/index.php/compou
nd/inspect/ChEMBL210
Contents 9009)
History ChemSpider None

Structure and properties ECHA InfoCard 100.029.692 (https://ec
Processing ha.europa.eu/substanc
Biosynthesis e-information/-/substan
Breakdown (cellulolysis) ceinfo/100.029.692)
Breakdown (thermolysis) EC Number 232-674-9
Hemicellulose E number E460 (thickeners, ...)
Regenerated cellulose PubChem CID 14055602 (https://pubc
Cellulose esters and ethers hem.ncbi.nlm.nih.gov/c
Commercial applications ompound/14055602)
Aspirational UNII SMD1X3XO9M (https://
See also fdasis.nlm.nih.gov/srs/s
References rsdirect.jsp?regno=SM
D1X3XO9M)
External links
CompTox DTXSID3050492 (http
Dashboard (EPA)
s://comptox.epa.gov/da
History shboard/DTXSID30504
92)
Cellulose was discovered in 1838 by the French chemist Anselme
Properties
Payen, who isolated it from plant matter and determined its chemical
formula.[3][10][11] Cellulose was used to produce the first successful Chemical formula (C6H10O5)n
thermoplastic polymer, celluloid, by Hyatt Manufacturing Company Molar mass 162.1406 g/mol per
in 1870. Production of rayon ("artificial silk") from cellulose began in glucose unit
the 1890s and cellophane was invented in 1912. Hermann Staudinger
Appearance white powder
https://en.wikipedia.org/wiki/Cellulose 1/11
determined the polymer structure of cellulose in 1920. The compound Density 1.5 g/cm3
was first chemically synthesized (without the use of any biologically Melting point 260–270 °C; 500–
derived enzymes) in 1992, by Kobayashi and Shoda.[12]
518 °F; 533–543 K
Decomposes[2]
Structure and properties Solubility in water none
Thermochemistry
Cellulose has no taste, is odorless, is hydrophilic with the contact
angle of 20–30 degrees,[13] is insoluble in water and most organic Std enthalpy of −963,000 J/mol
solvents, is chiral and is biodegradable. It was shown to melt at 467 °C formation
in pulse tests made by Dauenhauer et al. (2016).[14] It can be broken (ΔfH⦵298)
down chemically into its glucose units by treating it with concentrated Std enthalpy of −2828,000 J/mol
mineral acids at high temperature.[15] combustion
(ΔcH⦵298)
Cellulose is derived from D-glucose units, which condense through
Hazards
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 NFPA 704
straight chain polymer. Unlike starch, no coiling or branching occurs (fire diamond) 1
and the molecule adopts an extended and rather stiff rod-like
1 0
conformation, aided by the equatorial conformation of the glucose
residues. The multiple hydroxyl groups on the glucose from one chain
NIOSH (US health exposure limits):
form hydrogen bonds with oxygen atoms on the same or on a
neighbor chain, holding the chains firmly together side-by-side and PEL TWA 15 mg/m3 (total)
(Permissible) TWA 5 mg/m3 (resp)[2]
forming microfibrils with high tensile strength. This confers tensile
strength in cell walls where cellulose microfibrils are meshed into a REL TWA 10 mg/m3 (total)
polysaccharide matrix. The high tensile strength of plant stems and of (Recommended) TWA 5 mg/m3 (resp)[2]
the tree wood also arises from the arrangement of cellulose fibers
intimately distributed into the lignin matrix. The mechanical role of IDLH N.D.[2]
(Immediate
cellulose fibers in the wood matrix responsible for its strong structural danger)
resistance, can somewhat be compared to that of the reinforcement
bars in concrete, lignin playing here the role of the hardened cement Related compounds
paste acting as the "glue" in between the cellulose fibers. Mechanical Related Starch
properties of cellulose in primary plant cell wall are correlated with compounds
growth and expansion of plant cells.[16] Live fluorescence microscopy Except where otherwise noted, data are
techniques are promising in investigation of the role of cellulose in given for materials in their standard state
growing plant cells. [17] (at 25 °C [77 °F], 100 kPa).
verify (what is ?)
Compared to starch, cellulose is also much more crystalline. Whereas
starch undergoes a crystalline to amorphous transition when heated Infobox references
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 The arrangement of cellulose and
Cellulose under a microscope. between and within strands. Natural other polysaccharides in a plant cell
cellulose is cellulose I, with structures Iα wall.
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] A triple strand of cellulose showing
the hydrogen bonds (cyan lines)
Plant-derived cellulose is usually found in a mixture with hemicellulose, between glucose strands
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] Cotton fibres represent the purest
These nanocelluloses are of high technological interest due to their self- natural form of cellulose, containing
assembly into cholesteric liquid crystals,[23] production of hydrogels or more than 90% of this
aerogels,[24] use in nanocomposites with superior thermal and mechanical polysaccharide.
properties,[25] and use as Pickering stabilizers for emulsions.[26]
Processing
Biosynthesis
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)
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)
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
Hemicelluloses are polysaccharides related to cellulose that comprise 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
Cellulose is soluble in several kinds of media, several of which are the basis of commercial technologies. These
dissolution process is 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

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
Reagent Example Reagent Group R
ester
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

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

Acetic acid and butyric acid
(CAB) (C=O)CH2CH2CH3
Nitrocellulose (cellulose Nitric acid or another powerful

H or -NO2
Inorganic Inorganic nitrate) nitrating agent
esters acids Sulfuric acid or another powerful
Cellulose sulfate H or -SO3H
sulfuring agent
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 Water E
Reagent Example Reagent Group R = H or Application
ethers solubility number
Cold
Methylcellulose Chloromethane -CH3 water- E461
soluble
A commercial
thermoplastic
used in
Water- coatings, inks,
Alkyl Halogenoalkanes Ethylcellulose Chloroethane -CH2CH3 E462
insoluble binders, and
controlled-
release drug
tablets
Chloromethane -CH3 or -
Ethyl methyl
and E465
cellulose CH2CH3
chloroethane
Cold/hot Gelling and
Hydroxyethyl
Ethylene oxide -CH2CH2OH water- thickening
cellulose
soluble agent
Hydroxypropyl Cold
Propylene -
cellulose water- E463
oxide CH2CH(OH)CH3
(HPC) soluble
Hydroxyethyl Chloromethane -CH3 or - Cold
Production of
methyl and ethylene water-
CH2CH2OH cellulose films
Hydroxyalkyl Epoxides cellulose oxide soluble
Viscosity
Hydroxypropyl
Chloromethane -CH3 or - Cold modifier,
methyl
and propylene water- gelling, E464
cellulose CH2CH(OH)CH3
oxide soluble foaming and
(HPMC)
binding agent
Ethyl Chloroethane -CH2CH3 or—
hydroxyethyl and ethylene E467
CH2CH2OH
cellulose oxide
Often used as
its sodium
Carboxymethyl Cold/Hot
Halogenated Chloroacetic salt, sodium
Carboxyalkyl cellulose -CH2COOH water- E466
carboxylic acids acid carboxymethyl
(CMC) soluble
cellulose
(NaCMC)
The sodium carboxymethyl cellulose can be cross-linked to give the croscarmellose sodium (E468) for use as a
disintegrant in pharmaceutical formulations.
Commercial applications
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.[52]
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%). A strand of cellulose (conformation
Iα), showing the hydrogen bonds
Consumables: Microcrystalline cellulose (E460i) and powdered cellulose
(dashed) within and between
(E460ii) are used as inactive fillers in drug tablets[53] and a wide range of
cellulose molecules.
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.[54]
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.[55] 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.[56]
Aspirational
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.[57] Typical non-food energy crops include
industrial hemp, switchgrass, Miscanthus, Salix (willow), and Populus (poplar) species. A strain of Clostridium
bacteria found in zebra waste, can convert nearly any form of cellulose into butanol fuel.[58][59]
See also
Gluconic acid
Isosaccharinic acid, a degradation product of cellulose
Lignin
Zeoform
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"Cellulose" (https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Cellulose). Encyclopædia
Britannica. 5 (11th ed.). 1911.
Structure and morphology of cellulose (https://web.archive.org/web/20090426122947/http://www.cermav.cnr
s.fr/glyco3d/lessons/cellulose/index.html) by Serge Pérez and William Mackie, CERMAV-CNRS
Cellulose (https://web.archive.org/web/20051001072830/http://www.lsbu.ac.uk/water/hycel.html), by Martin
Chaplin, London South Bank University
Clear description of a cellulose assay method (https://web.archive.org/web/20050426105859/http://msa.ars.
usda.gov/la/srrc/fb/ca.html) at the Cotton Fiber Biosciences unit of the USDA.
Cellulose films could provide flapping wings and cheap artificial muscles for robots (http://www.technologyrev
iew.com/read_article.aspx?ch=infotech&sc=&id=17127&pg=1) – TechnologyReview.com
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Cellulose - Wikipedia

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14/10/2020 Cellulose - Wikipedia

Cellulose is mainly used to produce paperboard and paper. Smaller

History ChemSpider None

Several types of cellulose are known.

The chemical formula of cellulose is (C6H10O5)n where n is the degree of

Cellulose consists of fibrils with crystalline and amorphous regions. These

Cellulose esters and ethers

Ester derivatives include:

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

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

Cellulose acetate butyrate H or -(C=O)CH3 or -

Nitrocellulose (cellulose Nitric acid or another powerful

Ether derivatives include:

Paper products: Cellulose is the major constituent of paper, paperboard,

37. Bowen, Richard. "Digestive Function of Horses" (http://www.vivo.colostate.edu/hbooks/pathphys/digestion/h

Retrieved from "https://en.wikipedia.org/w/index.php?title=Cellulose&oldid=982718556"

This page was last edited on 9 October 2020, at 22:04 (UTC).

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