Adipic acid

Adipic acid

Chembox new
Name = Adipic acid
ImageFile = Adipic_acid_structure.png ImageName = Adipic acid
ImageFile1 = Adipic acid-3d.png IUPACName = hexanedioic acid
OtherNames = butane-1,4-dicarboxylic acid
Section1 = Chembox Identifiers
SMILES = OC(=O)CCCCC(=O)O
CASNo = 124-04-9
ChemSpiderID = 191
RTECS =
Section2 = Chembox Properties
C=6|H=10|O=4
Appearance = White crystals
Density = 1.36 g/cm³
Solubility = slightly soluble
MeltingPt = 152 °C (425 K)
BoilingPt = 337 °C (610 K)
pKa = 4.43, 5.41
Section3 = Chembox Structure
Coordination =
CrystalStruct =
Dipole =
Section7 = Chembox Hazards
MainHazards = flammable
FlashPt = 232 °C
RPhrases = R: R36
Section8 = Chembox Related
Function = dicarboxylic acids
OtherFunctn = glutaric acid
pimelic acid
OtherCpds = hexanoic acid

Adipic acid (IUPAC systematic name: hexanedioic acid) is a dicarboxylic acid. It is a white crystalline powder. Due to its long aliphatic chain, it is not very soluble in water.

Preparation

Historically, adipic acid was prepared from various fats using oxidation. Current commercial adipic acid is produced from cyclohexane by two oxidation steps.

# Cyclohexane + O2 → cyclohexanol and cyclohexanone+byproducts
# cyclohexanol/cyclohexanone + nitric acid + air → adipic acid + nitrous oxide

(The mixture of cyclohexanol and cyclohexanone produced from cyclohexane is commercially called "KA oil", the abbreviation of "Ketone-Alcohol oil".)

Other patented processes include those using phenol as feedstock. For example, phenol can be oxidized to KA oil, which is further processed give adipic acid. [US patent|7,250,537] Utilizing principles of green chemistry, a new method of synthesis has been developed, which involves oxidizing cyclohexene with hydrogen peroxide via a tungsten catalyst and a phase transfer catalyst to produce adipic acid. [cite journal |author=Sato, K.; Aoki, M.; Noyori, R. |title=A "Green" route to adipic acid: direct oxidation of cyclohexenes with 30 percent hydrogen peroxide |journal=Science |volume=281 |issue=5383 |pages=1646–7 |year=1998|doi = 10.1126/science. |doi_brokendate=2008-06-22] The waste product is water.

Uses

By far the main use of adipic acid is as monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming 6,6-nylon. Other uses include:

* Monomer for production of Polyurethane

* reactant to form plasticizers and lubricant components

* Food Ingredient as a flavorant and gelling aid.E-number E355.

* FDA citations - GRAS (21 CFR 184.1009), Indirect additive (21 CFR 175.300, 21 CFR 175.320, 21 CFR 176.170, 21 CFR 176.180, 21 CFR 177.1200, 21 CFR 177.1390 , 21 CFR 177.1500, 21 CFR 177.1630 , 21 CFR 177.1680, 21 CFR 177.2420, 21 CFR 177.2600)

* European Union Citations - Decision 1999/217/EC - Flavoing Substance; Directive 95/2/EC, Annex IV - Permitted Food Additive; 2002/72/EC, Annex A - Authorized monomer for Food Contact Plastics

References

External links

* [http://www.chemicalland21.com/arokorhi/industrialchem/organic/ADIPIC%20ACID.htm adipic acid on chemicalland]
* [http://www.solutia.com/pages/corporate/products/product.asp?product=164 Solutia Inc product website]
* [http://ptcl.chem.ox.ac.uk/MSDS/AD/adipic_acid.html Safety data from Oxford University]


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Look at other dictionaries:

  • adipic acid — an aliphatic dicarboxylic acid ({HO.CO.(CH2)4.CO.OH}), containing six carbon atoms in a linear chain. It is found in beet juice. It is used in the manufacture of synthetic plastics such as Nylon, as well as other products. [PJC] …   The Collaborative International Dictionary of English

  • adipic acid — adipo rūgštis statusas T sritis chemija formulė HOOC(CH₂)₄COOH atitikmenys: angl. adipic acid rus. адипиновая кислота ryšiai: sinonimas – heksano dirūgštis …   Chemijos terminų aiškinamasis žodynas

  • Adipic acid dihydrazide — Abbreviated ADH, Adipic acid dihydrazide is a special chemical used in the cross linking of water based emulsions. It can also be used as a hardener for certain epoxy resins. ADH is a symmetrical molecule with a C4 backbone and the reactive group …   Wikipedia

  • adipic acid — noun A white crystalline di carboxylic acid, CH(COOH); it has many industrial applications; when condensed with hexamethylene diamine it produces nylon. Syn: E355, acidity regulator, hexanedioic acid, butane 1, 4 dicarboxylic acid, butaned …   Wiktionary

  • adipic acid — Hexanedioic acid; the dicarboxylic acid, HOOC(CH2)4COOH. * * * adip·ic acid ə dip ik n a white crystalline dicarboxylic acid C6H10O4 formed by oxidation of various fats and also made synthetically for use esp. in the manufacture of nylon …   Medical dictionary

  • adipic acid — noun a carboxylic acid used in the manufacture of nylon • Syn: ↑hexanedioic acid • Hypernyms: ↑carboxylic acid …   Useful english dictionary

  • adipic acid — noun Etymology: International Scientific Vocabulary Date: 1877 a white crystalline dicarboxylic acid C6H10O4 formed by oxidation of various fats and also made synthetically for use especially in the manufacture of nylon …   New Collegiate Dictionary

  • adipic acid — /euh dip ik/, Chem. a white, crystalline, slightly water soluble solid, C6H10O4, used chiefly in the synthesis of nylon. Also called hexanedioic acid. [ADIP + IC] * * * …   Universalium

  • adipic acid — [ə dɪpɪk] noun Chemistry a crystalline fatty acid obtained from natural fats, used in making nylon. Origin C19: from L. adeps, adip fat + ic …   English new terms dictionary

  • adipic acid — a•dip′ic ac′id [[t]əˈdɪp ɪk[/t]] n. chem. a white, crystalline, slightly water soluble solid, C6H10O4, used chiefly in the synthesis of nylon • Etymology: 1875–90; < Ladip (see adipo ) + ic (the acid was obtained by oxidation of fats) …   From formal English to slang

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