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Adipic acid

Product Name
Adipic acid
CAS No.
124-04-9
Chemical Name
Adipic acid
Synonyms
adipic;adipate;Hexane diacid;Acifloctin;Hexanedioate;adipinic acid;AA, Adipic acid;Asapic;NA-9077;Adi-pure
CBNumber
CB0718158
Molecular Formula
C6H10O4
Formula Weight
146.14
MOL File
124-04-9.mol
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Adipic acid Property

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)
refractive index 
1.4880
FEMA 
2011 | ADIPIC ACID
Flash point:
385 °F
storage temp. 
Store below +30°C.
solubility 
methanol: 0.1 g/mL, clear, colorless
pka
4.43(at 25℃)
form 
Solid
color 
White
Odor
wh. monoclinic prisms, pract. odorless
PH
3.74(1 mM solution);3.22(10 mM solution);2.71(100 mM solution);
Water Solubility 
1.44 g/100 mL (15 ºC)
Merck 
14,162
JECFA Number
623
BRN 
1209788
Exposure limits
ACGIH: TWA 5 mg/m3
Dielectric constant
1.8（Ambient）
Stability:
Stable. Substances to be avoided include ammonia, strong oxidizing agents.
InChIKey
WNLRTRBMVRJNCN-UHFFFAOYSA-N
LogP
0.09 at 25℃
CAS DataBase Reference
124-04-9(CAS DataBase Reference)
NIST Chemistry Reference
Hexanedioic acid(124-04-9)
EPA Substance Registry System
Adipic acid (124-04-9)
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Safety

Hazard Codes 
Xi
Risk Statements 
36-41
Safety Statements 
26-39-24/25
WGK Germany 
1
RTECS 
AU8400000
Autoignition Temperature
788 °F
TSCA 
Yes
HS Code 
29171210
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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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR2341
Product name
Adipic Acid
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
200MG
Price
$200
Updated
2024/03/01
Sigma-Aldrich
Product number
8.18650
Product name
Adipic acid
Purity
for synthesis
Packaging
100G
Price
$43.2
Updated
2024/03/01
Sigma-Aldrich
Product number
8.18650
Product name
Adipic acid
Purity
for synthesis
Packaging
1KG
Price
$55.4
Updated
2024/03/01
Sigma-Aldrich
Product number
1.00090
Product name
Adipic acid
Purity
EMPROVE? ESSENTIAL, Ph. Eur., NF
Packaging
1KG
Price
$184
Updated
2024/03/01
Sigma-Aldrich
Product number
1.00090
Product name
Adipic acid
Purity
EMPROVE? ESSENTIAL Ph Eur,NF,FCC,E 355
Packaging
25kg
Price
$439
Updated
2024/03/01
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Adipic acid Chemical Properties,Usage,Production

Description

Adipic 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 Properties

Adipic 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 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.).

Uses

Adipic acid’s main use is in the production of 6,6 nylon. It is also used in resins, plasticizers, lubricants, polyurethanes, and food additives.

Uses

Adipic Acid is primarily used in the synthesis of nylon. It has been used as a reagent in the solid-state polymerization of nylon analogs.

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.

Definition

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

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.

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.

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.

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.

General Description

Adipic 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 Reactions

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

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.

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.

Flammability and Explosibility

Non flammable

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 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.

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.

Potential Exposure

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

storage

Adipic 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.

Shipping

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

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.]

Incompatibilities

Adipic 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 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

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.

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.

Adipic acid Preparation Products And Raw materials

Raw materials

Organic ester Copper METABORIC ACID 1,3-Butadiene Cyclohexene Cyclohexane Cupric acetate monohydrate Vanadium(V) oxide Nitric acid Cyclohexanol Sodium hydroxide Bromide Cyclohexanone Manganese(II) acetate

Preparation Products

Diethyl 2,5-dibromohexanedioate Dimethyl adipate 2,2-DIMETHYLCYCLOPENTANONE Polyurethane PolyesterPolyol Water-soluble resin polyesters containing quarternary ammonium groups Diethyl adipate NYLON 6 Monostearin 2,5-Bis(5-tert-butyl-2-benzoxazolyl)thiophene Hexamethylene Diisocyanate Dioctyl adipate Monoethyl Adipate Cyclopentanol Nylon 6/6 Dibutyl adipate Adiponitrile Hexamethylenediamine Glutaric anhydride Bis(2-ethylhexyl) adipate Glutaric acid Triethylene glycol dimethacrylate Cyclopentanone 2,5-Thiophenedicarboxylic acid LIGNOCERIC ACID Adipoyl chloride
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View Lastest Price from Adipic acid manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Adipic acid 124-04-9
Price
US $20.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000kg/Week
Release date
2024-05-06
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Adipic acid 124-04-9
Price
US $100.00-75.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-15
hebei hongtan Biotechnology Co., Ltd
Product
Adipic acid 124-04-9
Price
US $30.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
2000kg
Release date
2024-05-15

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  • FEMA 2011
  • HEXANDIOIC ACID
  • Adipic acid Manufacturer
  • Adipic acid 124-04-9
  • adipic acid, butane-1,4-dicarboxylic acid, hexanedioic acid, гександиовая кислота, 1,4-бутандикарбоновая кислота Гександиовая кислота, 1,4-бутандикарбоновая кислота
  • acideadipique
  • Acifloctin
  • Acinetten
  • Adilactetten
  • adipate
  • adipic
  • Adipinsαure
  • Adi-pure
  • ai3-03700
  • femanumber2011
  • Kyselina adipova
  • 1,4-Butanedicarboxylic acid~Hexanedioic acid
  • 1,4-Butanedicardicarboxylic acid
  • ADIPIC ACID 99.6+% FCC
  • ADIPIC ACID FREE ACID
  • ADIPIC ACID, 99+%
  • ADIPIC ACID EXTRA PURE
  • AdipicAcidPure
  • ADIPIC ACID ( 1,6-Hexanedioic Acid)
  • Adipic Acid-13C6
  • adi-pure high purity adipic acid
  • ADIPICACID,FCC
  • ADIPICACID,TECH(BULK
  • butenedicarboxylic acid
  • ADIPICACIDANDITSSODIUMSALTS
  • ADIPINSAEURE
  • Hexane diacid
  • Adipic Acid-1,6-13C6
  • ADI-PURE(R) high purity adipic acid, ADI-PURE(R) LGA adipic acid, Hexanedioic acid
  • 2-[(2R,4E,6E,8R,9R,11R,12S,13S,14R)-12-[(2S,3R,4S,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyl-oxan-2-yl]oxy-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]oxy-8-[(5S,6R)-5-dimethylamino-6-methyl-oxan-2-yl]oxy-14-hydroxy-13-methoxy-2,9-dimethyl-16-oxo-1-oxacyclohexadeca-4,6-dien-11-yl]acetaldehyde
  • Asapic
  • Hexanedioc acid
  • Inipol DS
  • NA-9077
  • (Hexanedioic acid)dianion
  • 1,4-Biscarboxylatobutane
  • Hexanedioate
  • Hexanedioic acidanion
  • Adipic Acid, Meets analytical specification of Ph.Eur.BP
  • AA, Adipic acid
  • Adipic acid;1,4-Butanedicardicarboxylic acid;Dicarboxylic acid C6;Hexanedioic acid
  • kyselinaadipova
  • kyselinaadipova(czech)
  • moltenadipicacid
  • oxoalcoholadipate