| Identification | More | [Name]
Adipic acid | [CAS]
124-04-9 | [Synonyms]
1,4-BUTANEDICARBOXYLIC ACID
1,6-HEXANEDIOIC ACID
ADIPIC ACID
adipinic acid
AKOS BBS-00004308
BUTANE-1,4-DICARBOXYLIC ACID
DICARBOXYLIC ACID C6
FEMA 2011
HEXANDIOIC ACID
RARECHEM AL BO 0180
acideadipique
Acifloctin
Acinetten
Adilactetten
adipate
adipic
Adipinsαure
Adi-pure
ai3-03700
femanumber2011 | [EINECS(EC#)]
204-673-3 | [Molecular Formula]
C6H10O4 | [MDL Number]
MFCD00004420 | [Molecular Weight]
146.14 | [MOL File]
124-04-9.mol |
| Chemical Properties | Back Directory | [Description]
Adipic acid is a white crystalline solid/crystalline granule, and its odour has not been
characterised. It is stable and incompatible with ammonia and strong oxidising 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,
plasticisers, urethanes, adhesives, and food additives. | [Appearance]
Adipic acid is a combustible, white, crystalline solid or powder. Odorless. | [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 | [refractive index ]
1.4880 | [Fp ]
385 °F
| [storage temp. ]
Store below +30°C. | [solubility ]
methanol: 0.1 g/mL, clear, colorless
| [form ]
Solid | [pka]
4.43(at 25℃) | [color ]
White | [Odor]
wh. monoclinic prisms, pract. odorless | [PH]
2.7 (23g/l, H2O, 25℃) | [Stability:]
Stable. Substances to be avoided include ammonia, strong oxidizing agents. | [Water Solubility ]
1.44 g/100 mL (15 ºC) | [JECFA Number]
623 | [Merck ]
14,162 | [BRN ]
1209788 | [Dielectric constant]
1.8（Ambient） | [Exposure limits]
ACGIH: TWA 5 mg/m3 | [InChIKey]
WNLRTRBMVRJNCN-UHFFFAOYSA-N | [LogP]
0.09 at 25℃ | [Uses]
Adipic 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. | [CAS DataBase Reference]
124-04-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Hexanedioic acid(124-04-9) | [EPA Substance Registry System]
124-04-9(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
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. | [General Description]
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. | [Reactivity Profile]
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. | [Air & Water Reactions]
Dust may form explosive mixture with air [USCG, 1999]. Insoluble in water. | [Health Hazard]
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. | [Health Hazard]
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. | [Potential Exposure]
Workers in manufacture of nylon, plasticizers, urethanes, adhesives, and food additives | [Fire Hazard]
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. | [First aid]
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 | [Shipping]
UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required | [Incompatibilities]
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.
| [Waste Disposal]
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 | [Physical properties]
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. | [Occurrence]
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.). | [Definition]
ChEBI: An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane. | [Preparation]
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. | [Production Methods]
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. | [Production Methods]
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. | [Reactions]
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. | [Biotechnological Production]
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. | [Flammability and Explosibility]
Nonflammable | [Pharmaceutical Applications]
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. | [Safety]
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 | [Synthesis]
By oxidation of cyclohexanol with concentrated nitric acid; by catalytic oxidation of cyclohexanone with air. | [Purification Methods]
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.] | [Regulatory Status]
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. |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
1
| [RTECS ]
AU8400000
| [Autoignition Temperature]
788 °F | [TSCA ]
Yes | [HS Code ]
29171210 | [storage]
Adipic acid should be kept stored in a tightly closed container, in a cool, dry, ventilated
area and protected against physical damage. In storage, adipic acid should be isolated from
incompatible substances and dust formation and ignition sources should be avoided. | [Precautions]
Occupational 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. | [Safety Profile]
Poison 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. | [Hazardous Substances Data]
124-04-9(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 5700 mg/kg LD50 dermal Rabbit > 7940 mg/kg |
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