Adipic acid CAS 124-04-9
Introduction：Basic information about Adipic acid CAS 124-04-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Adipic acid Basic information
| Product Name: | Adipic acid |
| Synonyms: | RARECHEM AL BO 0180;AKOS BBS-00004308;ADIPIC ACID;adipinic acid;1,6-HEXANEDIOIC ACID;1,4-BUTANEDICARBOXYLIC ACID;BUTANE-1,4-DICARBOXYLIC ACID;DICARBOXYLIC ACID C6 |
| CAS: | 124-04-9 |
| MF: | C6H10O4 |
| MW: | 146.14 |
| EINECS: | 204-673-3 |
| Product Categories: | alpha,omega-Alkanedicarboxylic Acids;alpha,omega-Bifunctional Alkanes;Industrial/Fine Chemicals;Monofunctional & alpha,omega-Bifunctional Alkanes;Food additive and acidulant;plasticizer;bc0001;124-04-9 |
| Mol File: | 124-04-9.mol |
Adipic acid Chemical Properties
| Melting point | 151-154 °C(lit.) |
| Boiling point | 265 °C100 mm Hg(lit.) |
| bulk density | 700kg/m3 |
| 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 |
| Fp | 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); |
| biological source | synthetic |
| Water Solubility | 1.44 g/100 mL (15 ºC) |
| Merck | 14,162 |
| JECFA Number | 623 |
| BRN | 1209788 |
| Dielectric constant | 1.8（Ambient） |
| Exposure limits | ACGIH: TWA 5 mg/m3 |
| Stability: | Stable. Substances to be avoided include ammonia, strong oxidizing agents. |
| Major Application | flavors and fragrances |
| Cosmetics Ingredients Functions | FRAGRANCE BUFFERING |
| Cosmetic Ingredient Review (CIR) | Adipic acid (124-04-9) |
| InChI | 1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10) |
| InChIKey | WNLRTRBMVRJNCN-UHFFFAOYSA-N |
| SMILES | OC(=O)CCCCC(O)=O |
| 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) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36-41 |
| Safety Statements | 26-39-24/25 |
| RIDADR | UN3077 |
| WGK Germany | 1 |
| RTECS | AU8400000 |
| Autoignition Temperature | 788 °F |
| TSCA | TSCA listed |
| HazardClass | 9 |
| HS Code | 29171210 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Dam. 1 |
| Hazardous Substances Data | 124-04-9(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 5700 mg/kg LD50 dermal Rabbit > 7940 mg/kg |
| 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 oxidativerancidity. It also occurs in beet juice, pork fat, guava fruit (Psidium guajava L.), papaya (Carica papaya L.) and raspberry (Rubusidaeus 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 orcyclohexanone or a mixture of the two compounds. Recently,oxidation of cyclohexene with 30% aqueous hydrogen peroxideunder organic solvent- and halide-free conditions has beenproposed as an environmentally friendly alternative for obtainingcolorless 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, thereare new efforts to develop an adipic acid production process using biorenewablesources. A direct biosynthesis route has not yet been reported. The possibleprecursors Z,Z-muconic acid and glucaric acid can be produced biotechnologicallyby fermentation. Z,Z-muconic acid can be made from benzoate with concentrationsup to 130 mM with a yield of close to 100 % (mol/mol) by Pseudomonas putidaKT2440-JD1 grown on glucose. Alternatively, it can be produced by engineeredE. coli directly from glucose at up to 260 mM with a yield of 0.2 mol Z,Zmuconicacid per mole glucose . The production of the second possible precursor, glucaric acid, by engineeredE. coli growing on glucose has been reported. However, the product titers werelow (e.g. 4.8 and 12 mM. To overcome the problem of low productconcentrations, an alternative synthetic pathway has been suggested but not yetdemonstrated . In a hydrogenation process, Z,Z-muconic acid and glucaric acid could beconverted chemically into adipic acid. Therefore, bimetallic nanoparticles orplatinum on activated carbon as catalysts have been studied . In particular,nanoparticles of Ru10Pt2 anchored within pores of mesoporous silica showed highselectivity and conversion rates, greater than 0.90 mol adipic acid per mole Z,Zmuconicacid. With platinum on activated carbon, conversion rates of0.97 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 thea–aminoadipate pathway ]. Finally, the production of adipic acid from longchaincarbon substrates has been suggested. The conversion of fatty acids intodicarboxylic 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 adipicacid 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 symptomsof coughing, sneezing, and blood-tinged mucous. |
| Flammability and Explosibility | Non flammable |
| Pharmaceutical Applications | Adipic acid is used as an acidifying and buffering agent inintramuscular, intravenous and vaginal formulations. It is alsoused in food products as a leavening, pH-controlling, or flavoringagent. Adipic acid has been incorporated into controlled-releaseformulation matrix tablets to obtain pH-independent release forboth weakly basicand weakly acidic drugs.It has also beenincorporated into the polymeric coating of hydrophilic monolithicsystems to modulate the intragel pH, resulting in zero-order releaseof a hydrophilic drug.The disintegration at intestinal pH of theenteric polymer shellac has been reported to improve when adipicacid was used as a pore-forming agent without affecting release inthe acidic media.Other controlled-release formulations haveincluded adipic acid with the intention of obtaining a late-burstrelease 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 foodproducts. The pure form of adipic acid is toxic by the IP route, andmoderately toxic by other routes. It is a severe eye irritant, and maycause 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 asstrong bases and reducing agents. Contact with alcohols, glycols,aldehydes, epoxides, or other polymerizing compounds can result inviolent reactions. |
| Toxics Screening Level | The initial threshold screening level (ITSL) for adipic acid is 50 μg/m3 based on an 8 hour averaging time. |
| 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 breathingdust, and keep the container closed. Workers should use adipic acid only with adequateventilation. Workers should wash thoroughly after handling adipic acid and keepaway from heat, sparks, and flame. Also, workers should use rubber gloves and laboratorycoats, 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 foodadditive in Europe. Included in an oral pastille formulationavailable in the UK. Included in the Canadian List of AcceptableNon-medicinal Ingredients. |
Adipic acid Preparation Products And Raw materials
| Raw materials | Sodium hydroxide-->Nitric acid-->Copper-->Cyclohexane-->Cyclohexanone-->1,3-Butadiene-->Copper (II) acetate monohydrate-->Cyclohexanol-->Vanadium(V) oxide-->Cyclohexene-->Bromide-->Manganese(II) acetate-->METABORIC ACID |
| Preparation Products | Cyclopentanone-->Polyurethane-->Glutaric acid-->Triethylene glycol dimethacrylate-->Hexamethylenediamine-->Hexamethylene Diisocyanate-->Glutaric anhydride-->LIGNOCERIC ACID-->2,5-Bis(5-tert-butyl-2-benzoxazolyl)thiophene-->Monostearin-->Cyclopentanol-->Adiponitrile-->PolyesterPolyol-->2,5-Thiophenedicarboxylic acid-->Diethyl adipate-->2,2-DIMETHYLCYCLOPENTANONE-->Adipoyl chloride-->NYLON 6-->polyesters containing quarternary ammonium groups-->Nylon 6/6-->Dioctyl adipate-->Water-soluble resin-->Diethyl 2,5-dibromohexanedioate-->Dibutyl adipate-->Bis(2-ethylhexyl) adipate-->Dimethyl adipate-->Monoethyl Adipate |
