ChemicalBook > Product Catalog > Organic Chemistry > Carboxylic acids and derivatives > Acyclic carboxylic acid > Adipic acid
Adipic acid Chemical Properties
- Melting point:151-154 °C(lit.)
- Boiling point:265 °C100 mm Hg(lit.)
- Density 1,36 g/cm3
- vapor density 5 (vs air)
- vapor pressure 1 mm Hg ( 159.5 °C)
- FEMA 2011 | ADIPIC ACID
- refractive index 1.4880
- Flash point:385 °F
- storage temp. Store below +30°C.
- solubility methanol: 0.1 g/mL, clear, colorless
- pka4.43(at 25℃)
- form Solid
- color White
- PH2.7 (23g/l, H2O, 25℃)
- Water Solubility 1.44 g/100 mL (15 ºC)
- JECFA Number623
- Merck 14,162
- BRN 1209788
- Stability:Stable. Substances to be avoided include ammonia, strong oxidizing agents.
- CAS DataBase Reference124-04-9(CAS DataBase Reference)
- NIST Chemistry ReferenceHexanedioic acid(124-04-9)
- EPA Substance Registry SystemAdipic acid (124-04-9)
- Hazard Codes Xi
- Risk Statements 36-41
- Safety Statements 26-39-24/25
- RIDADR UN 9077
- WGK Germany 1
- RTECS AU8400000
- Autoignition Temperature788 °F
- TSCA Yes
- HS Code 29171210
- Hazardous Substances Data124-04-9(Hazardous Substances Data)
- ToxicityLD50 orally in Rabbit: 5700 mg/kg LD50 dermal Rabbit > 7940 mg/kg
Adipic acid Usage And Synthesis
- DescriptionAdipic acid is a crystalline powder with practically no odor. It has the lowest acidity of any of the acids commonly used in foods and has excellent buffering capacity in the range of pH 2.5 to 3.0. Like succinic and fumaric acid, adipic acid is practically nonhygroscopic. Its addition to foods imparts a smooth, tart taste. In grape-flavored products, it adds a lingering supplementary flavor and gives an excellent set to food powders containing gelatin. As a result, adipic acid has found a wide number of uses as an accidulant in dry powdered food mixtures, especially in those products having delicate flavors and where addition of tang to the flavor is undesirable.
Its aqueous solutions have the lowest acidity of any of the common food acids. For concentrations from 0.5 to 2.4 g/100 mL, the pH of its solution varies less than half a unit. Hence, it can be used as a buffering agent to maintain acidities within the range of 2.5 to 3.0. This is highly desirable in certain foods, yet the pH is low enough to inhibit the browning of most fruits and other foodstuffs.
- Chemical PropertiesAdipic acid is the organic compound with the formula (CH2)4(COOH)2. From the industrial perspective, it is the most important dicarboxylic acid: About 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon. Adipic acid otherwise rarely occurs in nature.
- Physical propertiesAdipic 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.
- OccurrenceReported 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.).
- UsesAdipic acid’s main use is in the production of 6,6 nylon. It is also used in resins, plasticizers, lubricants, polyurethanes, and food additives.
- UsesAdipic Acid is primarily used in the synthesis of nylon. It has been used as a reagent in the solid-state polymerization of nylon analogs.
- UsesAdipic Acid is an acidulant and flavoring agent. it is characterized as stable, nonhygroscopic, and slightly soluble, with a water solubility of 1.9 g/100 ml at 20°c. it has a ph of 2.86 at 0.6% usage level at 25°c. it is used in powdered drinks, beverages, gelatin desserts, loz- enges, and canned vegetables. it is also used as a leavening acidulant in baking powder. it can be used as a buffering agent to maintain acidities within a range of ph 2.5–3.0. it is occasionally used in edi- ble oils to prevent rancidity.
- Production MethodsAdipic 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.
- DefinitionChEBI: An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.
- Production MethodsAdipic 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.
- PreparationAdipic 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.
- ReactionsAdipic 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.
- Biotechnological ProductionAdipic 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.
- General DescriptionAdipic acid is a white crystalline solid. Adipic acid 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 is used to make plastics and foams and for other uses.
- Air & Water ReactionsDust may form explosive mixture with air [USCG, 1999]. Insoluble in water.
- Reactivity ProfileAdipic 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.
- Health HazardExposures 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.
- Pharmaceutical ApplicationsAdipic 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
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.
- Safety ProfilePoison by intraperitoneal route. Moderately toxic by other routes. A severe eye irritant. Combustible when exposed to heat or flame; can react with oxidzing materials. When heated to decomposition it emits acrid smoke and fumes.
- SafetyAdipic 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
- Chemical SynthesisBy oxidation of cyclohexanol with concentrated nitric acid; by catalytic oxidation of cyclohexanone with air.
- Potential ExposureWorkers in manufacture of nylon, plasticizers, urethanes, adhesives, and food additives
- storageAdipic acid is normally stable but decomposes above boiling point. It should be stored in a tightly closed container in a cool, dry place, and should be kept away from heat, sparks, and open flame.
- ShippingUN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
- Purification MethodsFor 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.]
- IncompatibilitiesAdipic acid is incompatible with strong oxidizing agents as well as strong bases and reducing agents. Contact with alcohols, glycols, aldehydes, epoxides, or other polymerizing compounds can result in violent reactions.
- Waste DisposalDissolve 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
- PrecautionsOccupational workers should avoid contact of the adipic acid with the eyes, avoid breathing dust, and keep the container closed. Workers should use adipic acid only with adequate ventilation. Workers should wash thoroughly after handling adipic acid and keep away from heat, sparks, and flame. Also, workers should use rubber gloves and laboratory coats, aprons, or coveralls, and avoid creating a dust cloud when handling, transferring, and cleaning up.
- Regulatory StatusGRAS 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.
Adipic acid Preparation Products And Raw materials
- Preparation ProductsCyclopentanonePolyurethane foams1,5-Pentanedioic acidTriethylene glycol dimethacrylate1,6-HEXANEDIAMINE1,6-DiisocyanatohexaneGlutaric anhydrideLIGNOCERIC ACIDFluorescent Brightener 184MonostearinCyclopentanol1,4-DicyanobutanePolyesterPolyol2,5-Thiophenedicarboxylic acidDiethyl adipate2,2-DIMETHYLCYCLOPENTANONEAdipoyl chlorideNYLON 6polyesters containing quarternary ammonium groupsNYLON 6/6Dioctyl adipateWater-soluble resinDiethyl 2,5-dibromohexanedioateDibutyl adipate Bis(2-ethylhexyl) adipateDimethyl adipateMonoethyl Adipate
- Raw materialsSodium hydroxideNitric acidCopperCyclohexaneCyclohexanone1,3-BUTADIENECupric acetate monohydrate CyclohexanolVanadium pentoxide CyclohexeneBromideMANGANESE(II) ACETATEMETABORIC ACID
- Carbon Black Adipic dihydrazide (Adipic acid dihydrazide), 98% Citric acid Stearic acid D-SACCHARIC ACID 1,4-LACTONE 1,4-Cyclohexanedicarboxylic acid 2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester 1,2,3,4-CYCLOPENTANETETRACARBOXYLIC ACID Diethyl succinosuccinate TETRAHYDROFURAN-2,3,4,5-TETRACARBOXYLIC ACID Cyclobutane-1,2,3,4-tetracarboxylic dianhydride MUCIC ACID Dimethyl 1,4-cyclohexanedicarboxylate RUBRATOXIN B L-2-Aminoadipic acid Adipic acid methyl ester Hyaluronic acid Diethyl adipate
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