Hexenuronic acid

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Hexenuronic acid
Hexenuronic acid.svg
Names
IUPAC name
(2S,3R,4S)-3,4-dihydroxy-2-[(2R,3R,4S,5R)-4-hydroxy-2,5-dimethoxyoxan-3-yl]oxy-3,4-dihydro-2H-pyran-6-carboxylic acid
Other names
4-deoxy-4-hexenopyranosyluronic acid
4-deoxy-beta-L-threo-hex-4-enopyranosyluronic acid
Identifiers
3D model (JSmol)
AbbreviationsHexA
MeSH C095263
PubChem CID
  • InChI=1S/C13H20O10/c1-19-7-4-21-13(20-2)10(9(7)16)23-12-8(15)5(14)3-6(22-12)11(17)18/h3,5,7-10,12-16H,4H2,1-2H3,(H,17,18)/t5-,7+,8+,9-,10+,12+,13+/m0/s1
    Key: YIUVUZOUGAOFMC-CAIVYNQRSA-N
  • COC1COC(C(C1O)OC2C(C(C=C(O2)C(=O)O)O)O)OC
Properties
C13H20O10
Molar mass 336.293 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Hexenuronic acid (HexA) is a bicyclic organic compound with the formula C13H20O10. [1] [2] It is an unsaturated sugar produced during the kraft process in the creation of wood pulp. [2]

Contents

Kraft process

During the kraft process, which is the turning of wood into wood pulp for papermaking, wood chips are treated with sodium hydroxide and sodium sulfide. Sodium hydroxide catalyzes the demethylation of 4-O-methyl-D-glucuronoxylan, which is found at the ends of the polysaccharide xylan. [2] [1] [3]

Break down of 4-O-methyl-D-glucuronoxylan into HexA Dehydration of 4-O-methyl-D-glucuronoxylan.png
Break down of 4-O-methyl-D-glucuronoxylan into HexA

Hexenuronic acid decreases a wood's kappa number, which is a measure of bleachability of wood pulp, by 3-7. [3] It readily reacts with common wood pulp bleaching agents like ozone, peracetic acid, and chlorine dioxide. [2] [1] Consequently, research has focused on ways to break down hexenuronic acid prior to bleaching to decrease dangerous waste products and costs. [3]

The main method of destroying hexenuronic acid is to treat the wood pulp post kraft processing with strong acids at high temperatures. HexA is hydrolyzed and broken down into aldehydes and alcohols like 2-furoic acid and 5-carboxy-2-furaldehdye. [3] [2] This process has led to a 50% reduction in bleaching costs of the wood pulp in some cases. [2]

In microbes

Polysaccharide lyases (PL) are a type of enzyme that is found in numerous microorganisms including bacteriophages that break down parts of wood. [4] PL catalyzses β-elimination of uronic acid-containing polysaccharides into HexA. [4] [5]

Related Research Articles

<span class="mw-page-title-main">Hemicellulose</span> Class of plant cell wall polysaccharides

A hemicellulose is one of a number of heteropolymers, such as arabinoxylans, present along with cellulose in almost all terrestrial plant cell walls. Cellulose is crystalline, strong, and resistant to hydrolysis. Hemicelluloses are branched, shorter in length than cellulose, and also show a propensity to crystallize. They can be hydrolyzed by dilute acid or base as well as a myriad of hemicellulase enzymes.

<span class="mw-page-title-main">Sodium hydroxide</span> Chemical compound with formula NaOH

Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations Na+ and hydroxide anions OH.

<span class="mw-page-title-main">Sodium hypochlorite</span> Chemical compound (known in solution as bleach)

Sodium hypochlorite is an alkaline inorganic chemical compound with the formula NaOCl. It is commonly known in a dilute aqueous solution as bleach or chlorine bleach. It is the sodium salt of hypochlorous acid, consisting of sodium cations and hypochlorite anions.

<span class="mw-page-title-main">Pulp (paper)</span> Fibrous material used notably in papermaking

Pulp is a fibrous lignocellulosic material prepared by chemically, semi-chemically or mechanically producing cellulosic fibers from wood, fiber crops, waste paper, or rags. Mixed with water and other chemicals or plant-based additives, pulp is the major raw material used in papermaking and the industrial production of other paper products.

<span class="mw-page-title-main">Calcium hydroxide</span> Inorganic compound of formula Ca(OH)2

Calcium hydroxide (traditionally called slaked lime) is an inorganic compound with the chemical formula Ca(OH)2. It is a colorless crystal or white powder and is produced when quicklime (calcium oxide) is mixed with water. Annually, approximately 125 million tons of calcium hydroxide are produced worldwide.

<span class="mw-page-title-main">Pulpwood</span> Timber intended for processing into wood pulp for paper production

Pulpwood can be defined as timber that is ground and processed into a fibrous pulp. It is a versatile natural resource commonly used for paper-making but also made into low-grade wood and used for chips, energy, pellets, and engineered products.

<span class="mw-page-title-main">Kraft process</span> Process of converting wood into wood pulp

The kraft process (also known as kraft pulping or sulfate process) is a process for conversion of wood into wood pulp, which consists of almost pure cellulose fibres, the main component of paper. The kraft process involves treatment of wood chips with a hot mixture of water, sodium hydroxide (NaOH), and sodium sulfide (Na2S), known as white liquor, that breaks the bonds that link lignin, hemicellulose, and cellulose. The technology entails several steps, both mechanical and chemical. It is the dominant method for producing paper. In some situations, the process has been controversial because kraft plants can release odorous products and in some situations produce substantial liquid wastes.

<span class="mw-page-title-main">Pulp mill</span> Facility which pulps wood or plant fibre

A pulp mill is a manufacturing facility that converts wood chips or other plant fiber sources into a thick fiber board which can be shipped to a paper mill for further processing. Pulp can be manufactured using mechanical, semi-chemical, or fully chemical methods. The finished product may be either bleached or non-bleached, depending on the customer requirements.

Resin acid refers to mixtures of several related carboxylic acids, primarily abietic acid, found in tree resins. Nearly all resin acids have the same basic skeleton: three fused rings having the empirical formula C19H29COOH. Resin acids are tacky, yellowish gums that are water-insoluble. They are used to produce soaps for diverse applications, but their use is being displaced increasingly by synthetic acids such as 2-ethylhexanoic acid or petroleum-derived naphthenic acids.

<span class="mw-page-title-main">Black liquor</span> Industrial by-product

In industrial chemistry, black liquor is the by-product from the kraft process when digesting pulpwood into paper pulp removing lignin, hemicelluloses and other extractives from the wood to free the cellulose fibers.

Resin soap is a mix of salts of resin acids. It is a yellow gelatinous pasty soap with use in bleaching and cleaning and as a compound of some varnishes. It also finds use in rubber industry as an emulsifier. Often the soap is pretreated with formaldehyde and maleic anhydride.

<span class="mw-page-title-main">Bleach</span> Chemicals used to whiten or disinfect

Bleach is the generic name for any chemical product that is used industrially or domestically to remove colour from fabric or fiber or to disinfect after cleaning. It often refers specifically to a dilute solution of sodium hypochlorite, also called "liquid bleach".

Bleaching of wood pulp is the chemical processing of wood pulp to lighten its color and whiten the pulp. The primary product of wood pulp is paper, for which whiteness is an important characteristic. These processes and chemistry are also applicable to the bleaching of non-wood pulps, such as those made from bamboo or kenaf.

The sulfite process produces wood pulp that is almost pure cellulose fibers by treating wood chips with solutions of sulfite and bisulfite ions. These chemicals cleave the bonds between the cellulose and lignin components of the lignocellulose. A variety of sulfite/bisulfite salts are used, including sodium (Na+), calcium (Ca2+), potassium (K+), magnesium (Mg2+), and ammonium (NH4+). The lignin is converted to lignosulfonates, which are soluble and can be separated from the cellulose fibers. For the production of cellulose, the sulfite process competes with the Kraft process which produces stronger fibers and is less environmentally costly.

<span class="mw-page-title-main">Mannuronate-specific alginate lyase</span>

The enzyme mannuronate-specific alginate lyase catalyzes the degradation of alginate into various monosaccharide and polysaccharide products:

Deinking is the industrial process of removing printing ink from paperfibers of recycled paper to make deinked pulp.

Soda pulping is a chemical process for making wood pulp with sodium hydroxide as the cooking chemical. In the Soda-AQ process, anthraquinone (AQ) may be used as a pulping additive to decrease the carbohydrate degradation. The soda process gives pulp with lower tear strength than other chemical pulping processes, but has still limited use for easily pulped materials like straw and some hardwoods.

White liquor is a strongly alkaline solution mainly of sodium hydroxide and sodium sulfide. It is used in the first stage of the Kraft process in which lignin and hemicellulose are separated from cellulose fiber for the production of pulp. The white liquor breaks the bonds between lignin and cellulose. It is called white liquor due to its white opaque colour.

In industrial paper-making processes, organosolv is a pulping technique that uses an organic solvent to solubilise lignin and hemicellulose. It has been considered in the context of both pulp and paper manufacture and biorefining for subsequent conversion of cellulose to fuel ethanol. The process was invented by Theodor Kleinert in 1968 as an environmentally benign alternative to kraft pulping.

<span class="mw-page-title-main">Paper chemicals</span> Chemicals used in paper manufacturing

Paper chemicals designate a group of chemicals that are used for paper manufacturing, or modify the properties of paper. These chemicals can be used to alter the paper in many ways, including changing its color and brightness, or by increasing its strength and resistance to water. The chemicals can be defined on basis of their usage in the process.

References

  1. 1 2 3 Cadena EM, Vidal T, Torres AL (May 2010). "Influence of the hexenuronic acid content on refining and ageing in eucalyptus TCF pulp". Bioresource Technology. 101 (10): 3554–3560. Bibcode:2010BiTec.101.3554C. doi:10.1016/j.biortech.2009.11.105. PMID   20074936.
  2. 1 2 3 4 5 6 Chakar FS, Allison L, Ragauskas AJ, McDonough TJ, Sezgi US (November 2000). "Influence of hexenuronic acids on us bleaching operations". TAPPI Journal. 83 (11).
  3. 1 2 3 4 Petit-Breuilh X, Zaror C, Melo R (December 2004). "Hexenuronic acid removal from unbleached kraft eucalyptus pulp by peroxymonosulfuric acid". Journal of the Chilean Chemical Society. 49 (4): 355–360. doi: 10.4067/S0717-97072004000400016 . ISSN   0717-9707.
  4. 1 2 Sutherland IW (July 1995). "Polysaccharide lyases". FEMS Microbiology Reviews. 16 (4): 323–347. doi: 10.1111/j.1574-6976.1995.tb00179.x . PMID   7654407.
  5. Quan Y, da Silva NM, de Souza Lima BJ, de Hoog S, Vicente VA, Mayer V, et al. (March 2022). "Black fungi and ants: a genomic comparison of species inhabiting carton nests versus domatia". IMA Fungus. 13 (1): 4. doi: 10.1186/s43008-022-00091-5 . PMC   8900376 . PMID   35256015.