124-04-9

Adipic acid is a white crystalline solid/granule; its odor has not been characterized. It is stable and incompatible with ammonia and strong oxidizing agents. It may form combustible dust concentrations in air. The likely routes of exposure to workers are by skin contact and inhalation at workplaces. It is used in the manufacture of nylon, plasticizers, urethanes, adhesives, and food additives.

ADIPIC ACID(124-04-9) is a white crystalline solid. ADIPIC ACID(124-04-9) is insoluble in water. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. ADIPIC ACID(124-04-9) is used to make plastics and foams and for other uses.

ADIPIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in ADIPIC ACID to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. Behavior in Fire: Melts and may decompose to give volatile acidic vapors of valeric acid and other substances.

Dust may form explosive mixture with air [USCG, 1999]. Insoluble in water.

Exposures to adipic acid cause pain, redness of the skin and eyes, tearing or lacrimation. Adipic acid has been reported as a non-toxic chemical. Excessive concentrations of adipic acid dust are known to cause moderate eye irritation, irritation to the skin, and dermatitis.It may be harmful if swallowed or inhaled. It causes respiratory tract irritation with symptoms of coughing, sneezing, and blood-tinged mucous.

Inhalation of vapor irritates mucous membranes of the nose and lungs, causing coughing and sneezing. Contact with liquid irritates eyes and has a pronounced drying effect on the skin; may produce dermatitis.

Workers in manufacture of nylon, plasticizers, urethanes, adhesives, and food additives

Behavior in Fire: Melts and may decompose to give volatile acidic vapors of valeric acid and other substances. Dust may form explosive mixture with air.

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. If this chemical has been inhaled, remove from exposure and transfer promptly to a medical facility

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

Dust may form explosive mixture with air. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates, and dithionites (releasing hydrogen sulfate and oxides of sulfur). Reacts with oxidizers, reducing agents; and strong bases. Dust forms an explosive mixture with air. Frictionfrom stirring, pouring, or pneumatic transfer can form electrostatic charge on dry material. React violently with strong oxidizers, bromine, 90% hydrogen peroxide, phosphorus trichloride, silver powders or dust. Mixture with some silver compounds forms explosive salts of silver oxalate. Incompatible with silver compounds. Corrosive to some metals.

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed

Adipic acid is a straight-chain dicarboxylic acid that exists as a white crystalline compound at standard temperature and pressure. Adipic acid is one of the most important industrial chemicals and typically ranks in the top 10 in terms of volume used annually by the chemical industry.

Reported found as a minor constituent in butter, and has been found in other fats as a product of oxidative rancidity. It also occurs in beet juice, pork fat, guava fruit (Psidium guajava L.), papaya (Carica papaya L.) and raspberry (Rubus idaeus L.).

ChEBI: An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.

Adipic acid is produced from a mixture of cyclohexanol and cyclohexanone called "KA oil", the abbreviation of "ketone-alcohol oil." The KA oil is oxidized with nitric acid to give adipic acid, via a multistep pathway. Early in the reaction the cyclohexanol is converted to the ketone, releasing nitrous acid:
HOC₆H₁₁ + HNO₃ → OC₆H₁₀ + HNO₂ + H₂O
Among its many reactions, the cyclohexanone is nitrosated, setting the stage for the scission of the C- C bond:
HNO₂ + HNO₃ → NO+NO₃^- + H₂O
OC₆H₁₀ + NO⁺→ OC₆H₉^-2 - NO + H⁺
Side products of the method include glutaric and succinic acids.
Related processes start from cyclohexanol, which is obtained from the hydrogenation of phenol.

Adipic acid can be manufactured using several methods, but the traditional and main route of preparation is by the two-step oxidation of cyclohexane (C₆H₁₂). In the first step, cyclohexane is oxidized to cyclohexanone and cyclohexanol with oxygen or air. This occurs at a temperature of approximately 150°C in the presence of cobalt or manganese catalysts. The second oxidation is done with nitric acid and air using copper or vanadium catalysts. In this step, the ring structure is opened and adipic acid and nitrous oxide are formed. Other feedstocks such as benzene and phenol may be use to synthesize adipic acid. Adipic acid production used to be a large emitter of nitrous oxide, a greenhouse gas, but these have been controlled in recent years using pollution abatement technology.

Adipic acid is prepared by nitric acid oxidation of cyclohexanol or cyclohexanone or a mixture of the two compounds. Recently, oxidation of cyclohexene with 30% aqueous hydrogen peroxide under organic solvent- and halide-free conditions has been proposed as an environmentally friendly alternative for obtaining colorless crystalline adipic acid.

Adipic acid is a dibasic acid (can be deprotonated twice). Its pKa's are 4.41 and 5.41.
With the carboxylate groups separated by four methylene groups, adipic acid is suited for intramolecular condensation reactions. Upon treatment with barium hydroxide at elevated temperatures, it undergoes ketonization to give cyclopentanone.

Adipic acid is industrially produced by chemical synthesis. However, there are new efforts to develop an adipic acid production process using biorenewable sources. A direct biosynthesis route has not yet been reported. The possible precursors Z,Z-muconic acid and glucaric acid can be produced biotechnologically by fermentation. Z,Z-muconic acid can be made from benzoate with concentrations up to 130 mM with a yield of close to 100 % (mol/mol) by Pseudomonas putida KT2440-JD1 grown on glucose. Alternatively, it can be produced by engineered E. coli directly from glucose at up to 260 mM with a yield of 0.2 mol Z,Zmuconic acid per mole glucose .
The production of the second possible precursor, glucaric acid, by engineered E. coli growing on glucose has been reported. However, the product titers were low (e.g. 4.8 and 12 mM. To overcome the problem of low product concentrations, an alternative synthetic pathway has been suggested but not yet demonstrated .
In a hydrogenation process, Z,Z-muconic acid and glucaric acid could be converted chemically into adipic acid. Therefore, bimetallic nanoparticles or platinum on activated carbon as catalysts have been studied . In particular, nanoparticles of Ru10Pt2 anchored within pores of mesoporous silica showed high selectivity and conversion rates, greater than 0.90 mol adipic acid per mole Z,Zmuconicacid. With platinum on activated carbon, conversion rates of 0.97 mol.mol-1 of Z,Z-muconic acid into adipic acid have been shown. Another possibility would be the production of adipic acid from glucose via the a–aminoadipate pathway ]. Finally, the production of adipic acid from longchain carbon substrates has been suggested. The conversion of fatty acids into dicarboxylic acids by engineered yeast strains has been reported.

Nonflammable

Adipic acid is used as an acidifying and buffering agent in intramuscular, intravenous and vaginal formulations. It is also used in food products as a leavening, pH-controlling, or flavoring agent.
Adipic acid has been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basicand weakly acidic drugs.It has also been incorporated into the polymeric coating of hydrophilic monolithic systems to modulate the intragel pH, resulting in zero-order release of a hydrophilic drug.The disintegration at intestinal pH of the enteric polymer shellac has been reported to improve when adipic acid was used as a pore-forming agent without affecting release in the acidic media.Other controlled-release formulations have included adipic acid with the intention of obtaining a late-burst release profile.

Adipic acid is used in pharmaceutical formulations and food products. The pure form of adipic acid is toxic by the IP route, and moderately toxic by other routes. It is a severe eye irritant, and may cause occupational asthma.
LD₅₀ (mouse, IP): 0.28 g/kg
LD₅₀ (mouse, IV): 0.68 g/kg
LD₅₀ (mouse, oral): 1.9 g/kg
LD₅₀ (rat, IP): 0.28 g/kg
LD₅₀ (rat, oral): >11 g/kg

By oxidation of cyclohexanol with concentrated nitric acid; by catalytic oxidation of cyclohexanone with air.

For use as a volumetric standard, adipic acid is crystallised once from hot water with the addition of a little animal charcoal, dried at 120o for 2hours, then recrystallised from acetone and again dried at 120o for 2hours. Other purification procedures include crystallisation from ethyl acetate and from acetone/petroleum ether, fusion followed by filtration and crystallisation from the melt, and preliminary distillation under vacuum. [Beilstein 2 IV 1956.]

GRAS listed. Included in the FDA Inactive Ingredients Database (IM, IV, and vaginal preparations). Accepted for use as a food additive in Europe. Included in an oral pastille formulation available in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.