ChemicalBook
Chinese Japanese Germany Korea

Adipic acid

Adipic acid
Adipic acid structure
CAS No.
124-04-9
Chemical Name:
Adipic acid
Synonyms
adipic;Asapic;adipate;NA-9077;Adi-pure;FEMA 2011;Acinetten;ai3-03700;Inipol DS;adipicaci
CBNumber:
CB0718158
Molecular Formula:
C6H10O4
Formula Weight:
146.14
MOL File:
124-04-9.mol

Adipic acid 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)
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
PH
2.7 (23g/l, H2O, 25℃)
Water Solubility 
1.44 g/100 mL (15 ºC)
JECFA Number
623
Merck 
14,162
BRN 
1209788
Stability:
Stable. Substances to be avoided include ammonia, strong oxidizing agents.
InChIKey
WNLRTRBMVRJNCN-UHFFFAOYSA-N
FDA 21 CFR
184.1009; 582.1009; 175.300; 175.320; 177.1680
Substances Added to Food (formerly EAFUS)
ADIPIC ACID
SCOGS (Select Committee on GRAS Substances)
Adipic acid
CAS DataBase Reference
124-04-9(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
76A0JE0FKJ
NIST Chemistry Reference
Hexanedioic acid(124-04-9)
EPA Substance Registry System
Adipic acid (124-04-9)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS08,GHS07
Signal word  Warning
Hazard statements  H335-H372-H402-H319
Precautionary statements  P280i-P337+P313-P305+P351+P338-P260-P264-P270-P271-P273-P280-P304+P340+P312-P305+P351+P338+P337+P313-P314-P403+P233-P405-P501
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
Toxicity LD50 orally in Rabbit: 5700 mg/kg LD50 dermal Rabbit > 7940 mg/kg
NFPA 704
1
1 0

Adipic acid price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 09582 Adipic acid BioXtra, ≥99.5% (HPLC) 124-04-9 250g $35.5 2021-03-22 Buy
Sigma-Aldrich 09582 Adipic acid BioXtra, ≥99.5% (HPLC) 124-04-9 50g $25.4 2021-03-22 Buy
Sigma-Aldrich PHR2341 Adipic Acid Pharmaceutical Secondary Standard; Certified Reference Material 124-04-9 200MG $149 2021-03-22 Buy
Sigma-Aldrich Y0000110 Adipic acid European Pharmacopoeia (EP) Reference Standard 124-04-9 $190 2021-03-22 Buy
Sigma-Aldrich 1.00090 Adipic acid EMPROVE? ESSENTIAL Ph Eur,NF,FCC,E 355 124-04-9 25 kg $426 2021-03-22 Buy

Adipic acid Chemical Properties,Uses,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.
Adipic acid
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.

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.

Definition

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

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.

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

Chemical 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

Preparation Products


Adipic acid Suppliers

Global( 564)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Hebei Runbin Biotechnology Co. LTD
13180553332 13180553332
2179877681@qq.com CHINA 1000 58
Dayang Chem (Hangzhou) Co.,Ltd.
17705817739 +86-571-88938639
+86-571-88938652,+86-571- 88492614 info@dycnchem.com CHINA 52932 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8909 55
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418679
86-0551-65418697 info@tnjchem.com China 3000 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29954 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293
+86 0531-67809011 sales@sdzschem.com CHINA 2941 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
Jinan Finer Chemical Co., Ltd
+8615508631887 +86-531-88989536
+86-531-88989539 sales@finerchem.com CHINA 1697 58
Hebei Guanlang Biotechnology Co., Ltd.
+8619930503282
sales3@crovellbio.com China 5873 58

View Lastest Price from Adipic acid manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-26 Adipic acid
124-04-9
US $20.00 / KG 100g 99% 20tons Hanhong Medicine Technology (Hubei) Co., Ltd.
2021-11-26 Adipic acid
124-04-9
US $4.70 / KG 1ASSAYS 99% 10tons Baoji Guokang Bio-Technology Co., Ltd.
2021-11-15 Adipic acid
124-04-9
US $1.80 / KG 1000KG 98% 50ton/Month Hebei Yirun Sega Biological Technology Co. Ltd

Adipic acid Spectrum


124-04-9(Adipic acid)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved