ADIPIC ACID

CAS No.: 124-04-9
EC No.: 204-673-3

Synonyms:
ADIPIC ACID; adipic acid; adipic asit; adıbıc acide; adibik asit; abidik asit; adipik asit; akipik asit; ADİPİK ASİTE; adipil asit; adipik asit dihidrzat; hexanedioic acid; 1,4-Butanedicarboxylic acid; 1,4-dicarboxy; Adipinic acid; Hexanedioic acid; hekzanedoık asit; butanedikarboxyasit; Adipic acid Butane-1,4-dicarboxylic acid Hexane-1,6-dioic acid 1,4-butanedicarboxylic acid; Ethanedioic acid (Oxalic acid) C2H2O4; Propanedioic acid (Malonic acid) C3H4O4; Butandioic acid (Succinic acid) C4H6O4; Adipic dihydrazide; Adipohydrazide; 1071-93-8; Adipic acid dihydrazide; Hexanedihydrazide; Hexanedioic acid, dihydrazide; Hydrazidehexanedioic Acid; Monohydrazide Hexanedioic Acid; NSC 9926; Adipic acid; Acifloctin; Acinetten; Adilactetten; Hexanedioic acid [ACD/Index Name]; Adipic acid;Acifloctin; Acinetten; Adilactetten; 1,4-Butanedicarboxylic acid; 1,6-Hexanedioic acid; Adipinic acid; Kyselina adipova; Adi-pure; Hexanedioc acid; Monohydrazide Adipic Acid; 1-Hydrazidehexanedioic Acid; Monohydrazide Hexanedioic Acid; NSC 9926; DMSO (Slightly); Methanol (Slightly); heksanoık asit; adipike aide; adipik asit; Octanedioic acid (Suberic acid) C8H14O4; Nonanedioic acid (Azelaic acid); Hexanedioic acid; adipic acid; hexanedioic acid; 124-04-9; Adipinic acid; 1,4-Butanedicarboxylic acid; Adilactetten; Acifloctin; Acinetten; 1,6-Hexanedioic acid; Molten adipic acid; Kyselina adipova; Adipinsaure [German]; Acide adipique [French]; Kyselina adipova [Czech]; Hexanedioate; Adipinsaeure; Adi-pure; UNII-76A0JE0FKJ; NSC 7622; MFCD00004420; Adipic acid [NF]; Adipic acid, 99%; Hexan-1,6-dicarboxylate; 76A0JE0FKJ; butane-1,4-dicarboxylic acid; 1,6-HEXANE-DIOIC ACID; CHEBI:30832; NSC7622; Adipic acid (NF); NCGC00091345-01; E355; hexane-1,6-dioic acid; DSSTox_CID_1605; DSSTox_RID_76232; DSSTox_GSID_21605; Adipinsaure; Acide adipique; FEMA Number 2011; CAS-124-04-9; CCRIS 812; FEMA No. 2011; HSDB 188; EINECS 204-673-3; BRN 1209788; Adipinate; Molten adipate; AI3-03700; adipic acid group; hexane dioic acid; 1,6-Hexanedioate; 0L1; Neopentyl Glycol Flake; ACMC-1BBQS; C6-140-polymorph-I; C6-180-polymorph-I; C6-220-polymorph-I; C6-260-polymorph-I; C6-298-polymorph-I; 1, 6-Hexanedioic Acid; Adipic acid, >=99%; WLN: QV4VQ; bmse000424; EC 204-673-3; SCHEMBL4930; CHEMBL1157; NCIOpen2_001004; NCIOpen2_001222; HOOC-(CH2)4-COOH; Adipic acid, >=99.5%; 4-02-00-01956 (Beilstein Handbook Reference); BIDD:ER0342; INS No. 355; DTXSID7021605; Adipic acid, puriss., 99.8%; Pharmakon1600-01301012; NSC-7622; ZINC1530348; Tox21_111118; Tox21_202161; Tox21_300344; ANW-18185; BBL011615; LMFA01170048; NSC760121; SBB040846; STL163338; AKOS000119031; Tox21_111118_1; CCG-230896; CS-W018238; HY-W017522; MCULE-1336748609; NE10314; NSC-760121; NCGC00091345-02; NCGC00091345-03; NCGC00091345-04; NCGC00091345-05; NCGC00254389-01; NCGC00259710-01; AC-10343; BP-21150; BP-30248; Hexanedioic Acid, Butanedicarboxylic Acid; 101-EP2269610A2; 101-EP2269988A2; 101-EP2270002A1; 101-EP2270008A1; 101-EP2270113A1; 101-EP2272935A1; 101-EP2275413A1; 101-EP2275417A2; 101-EP2277507A1; 101-EP2277848A1; 101-EP2281559A1; 101-EP2284146A2; 101-EP2284147A2; 101-EP2284162A2; 101-EP2284163A2; 101-EP2284165A1; A0161; Adipic acid, BioXtra, >=99.5% (HPLC); Adipic acid, SAJ special grade, >=99.5%; E 355; E-355; FT-0606810; ST50214430; Adipic acid, Vetec(TM) reagent grade, >=99%; C06104; D08839; AB00988898-01; AB00988898-03; Q357415; SR-01000944270; J-005034; J-519542; SR-01000944270-2; Z57127533; Adipic acid, certified reference material, TraceCERT(R); F0001-0377; Adipic acid, European Pharmacopoeia (EP) Reference Standard; 1F1316F2-7A32-4339-8C2A-8CAA84696C95; Adipic acid, United States Pharmacopeia (USP) Reference Standard; Adipic acid, meets analytical specification of Ph.Eur., BP, E 355, 99.6-101.0% (calc. to the dried substance)

ADIPIC ACID

Adipic acid is produced from a mixture of cyclohexanone and cyclohexanol 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 › OC(CH2)5 + 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. Nitrous oxide is produced in about one to one mole ratio to the adipic acid, as well, via the intermediacy of a nitrolic acid.
Related processes start from cyclohexanol, which is obtained from the hydrogenation of phenol.
Alternative methods of production
Several methods have been developed by carbonylation of butadiene. For example, the hydrocarboxylation proceeds as follows:
CH2=CH-CH=CH2 + 2 CO + 2 H2O › HO2C(CH2)4CO2H
Another method is oxidative cleavage of cyclohexene using hydrogen peroxide. The waste product is water.
Historically, adipic acid was prepared by oxidation of various fats,thus the name (ultimately from Latin adeps, adipis - "animal fat"; cf. adipose tissue). Reactions
Adipic acid is a dibasic acid (it has two acidic groups). The pKa values for their successive deprotonations 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.
Uses
About 60% of the 2.5 billion kg of adipic acid produced annually is used as monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming nylon 66. Other major applications also involve polymers; it is a monomer for production of polyurethane and its esters are plasticizers, especially in PVC.
In medicine
Adipic acid has been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and 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 In foods
Small but significant amounts of adipic acid are used as a food ingredient as a flavorant and gelling aid. It is used in some calcium carbonate antacids to make them tart. As an acidulant in baking powders, it avoids the undesirable hygroscopic properties of tartaric acid.Adipic acid, rare in nature, does occur naturally in beets, but this is not an economical source for commerce compared to industrial synthesis.
Safety
Adipic acid, like most carboxylic acids, is a mild skin irritant. It is mildly toxic, with a median lethal dose of 3600 mg/kg for oral ingestion by rats.
Environmental
The production of adipic acid is linked to emissions of N
2O,a potent greenhouse gas and cause of stratospheric ozone depletion. At adipic acid producers DuPont and Rhodia (now Invista and Solvay, respectively), processes have been implemented to catalytically convert the nitrous oxide to innocuous products:
2 N2O › 2 N2 + O2
Adipic acid is a substance used for the preparation of nylon, polyurethanes, and other products of commercial interest. The industrial synthesis of adipic acid uses nitric acid oxidation of a mixture of cyclohexanone and cyclohexanol termed "KA oil" (ketone and alcohol-oil). This procedure generates nitrous oxide, a substance that increases greenhouse gases, damages the ozone layer, and causes acid rain. On a laboratory scale, it has been traditionally prepared from cyclohexene by oxidation with potassium permanganate. An alternative with less environmental impact than the traditional method involves the preparation of adipic acid from cyclohexene oxidation with H2O2 and sodium tungstate. This procedure is considered a green method and involves a series of events that make a low environmental impact:
The H2O2 is a green oxidant easy to handle and produces only water as a byproduct of the reaction.
The sodium tungstate is used in catalytic amounts, is of low toxicity, and can be used several times (recyclable).
This method is industrially applicable in laboratory scale experiments both at miniscale and microscale.
Adipic Acid
Traditional feedstock for the synthesis of adipic acid is benzene. Benzene is hydrogenated using Ni-Al2O3 catalyst at 370-800 psi to cyclohexane. This is oxidized using Co catalyst to a mixture of cyclohexanone and cyclohexanol. This is then converted to adipic acid using ammonium vanadate and nitric acid, with the help of a catalyst. Alternative feedstock in the synthesis of adipic acid is D glucose, which is converted to cis-muconic acid using E. coli, which is further hydrogenated to adipic acid using hydrogen gas. This approach eliminates several reaction and separation steps.
A typical route is that via cyclohexane, and cyclohexanol. To produce cyclohexane, benzene is subjected to continuous liquid phase hydrogenation at 340 lbf/in2 pressure and a temperature of 210°C using a Raney nickel catalyst. After cooling and separation of the catalyst the produce is fed to the cyclohexane store. In the next stage of the operation for cyclohexane is preheated and continuously oxidised in the liquid phase by air using a trace of cobalt naphthenate as catalyst. This gives an approximately 70% yield of a mixture of cyclohexanol and cyclohexanone with a small quantity of adipic acid. The cyclohexanol-cyclohexanone mixture is converted into adipic acid by continuous oxidation with 50% HNO3 at about 75°C using a copper-ammonium vanadate catalyst. The adipic acid is carefully purified by subjection to such processes as steam distillation and crystallisation. The pure material has a melting point of 151°C. Adipic acid is an important inudstrial dicarboxylic acid with about 2. 5 billion kilograms produced per year. It is used mainly in the production of nylon. It occurs relatively rarely in nature. It has a tart taste and is also used as an additive and gelling agent in jello or gelatins. It is also used in some calcium carbonate antacids to make them tart. Adipic acid has also been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidic drugs. Adipic acid in the urine and in the blood is typically exogenous in origin and is a good biomarker of jello consumption. In fact, a condition known as adipic aciduria is actually an artifact of jello consumption (PMID: 1779643). However, certain disorders (such as diabetes and glutaric aciduria type I. ) can lead to elevated levels of adipic acid snd other dicarboxcylic acids (such as suberic acid) in urine(PMID: 17520433, 6778884). Moreover, adipic acid is also found to be associated with 3-hydroxy-3-methylglutaryl-CoA lyase deficiency, carnitine-acylcarnitine translocase deficiency, malonyl-Coa decarboxylase deficiency, and medium Chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism. Adipic acid is a key component of nylon 6,6 and thermoplastic polyurethanes. Verdezyne is currently the only company that has demonstrated production and recovery of adipic acid at pilot scale through fermentation of low cost plant sourced oil feedstocks. Used in everyday products which contain adipic acid include clothing, footwear, furniture, carpets, automobile parts and nylon fabric. Catalogue Number
818650
Synonyms: Hexanedioic acid
CAS number: 124-04-9
EC index number: 607-144-00-9
EC number: 204-673-3
Hill Formula: C6H0°O4
Molar Mass: 146.14 g/mol
HS Code: 2917 12 00
Physicochemical Information
Density: 1.36 g/cm3 (25 °C)
Flash point: 196 °C
Ignition temperature: 405 °C
Melting Point: 150.9 °C
pH value: 2.7 (23 g/l, H²O, 25 °C)
Vapor pressure: 0.097 hPa (18.5 °C)
Bulk density: 700 kg/m3
Solubility: 15 g/l

Adipic acid, or more formally hexanedioic acid, is a white crystalline solid that melts at 152 ºC. It is one of the most important monomers in the polymer industry.

Adipic acid is found in beet juice, but the article of commerce—≈2.5 million tonnes of it per year—is manufactured. In 1906, French chemists L. Bouveault and R. Locquin reported that adipic acid can be produced by oxidizing cyclohexanol. Today, the most common manufacturing process is the nitric acid (HNO3) oxidation of a cyclohexanol–cyclohexanone mixture called KA (for ketone–alcohol) oil.

Almost all adipic acid is used as a comonomer with hexamethylenediamine to produce nylon 6-6. It is also used to manufacture other polymers such as polyurethanes.

Using HNO3 to produce adipic acid has its downside: Copious amounts of nitrous oxide (N2O), a greenhouse gas, are coproduced and released into the atmosphere. In late 2014, K. C. Hwang and A. Sagadevan of National Tsing Hua University (Hsinchu City, Taiwan) reported a process that uses ozone and ultraviolet (UV) light to oxidize KA oil to adipic acid. This method eliminates the production of N2O; but before the process can be used commercially, problems associated with the formation of organic peroxides from ozone and the difficulty of using UV light on a large scale must be overcome.

Adipic Acid
CAS: 124-04-9

Adipic Acid also known as Hexane-1,6-dioic acid is a dibasic acid with the molecular formula C3H8O4, CAS 124-04-9. Adipic acid is slightly soluble in water and soluble in alcohol and acetone.

adipic acid

Production
Adipic acid is white, crystalline compound mainly obtained by oxidation of cyclohexanol and cyclohexanone with nitric acid. An alternative method of production of adipic acid is the hydrocarbonylation of butadiene, oxidation cleavage of cyclohexene.

Uses
More than 92% of the production of adipic acid is dedicated for the production of nylon 6,6 by a reaction with HMD Hexamethylene diamine. Nylon is utilized in fibbers, clothing, plastics, filaments, food packaging. Adipic acid is also used in polyurethane resins, foam, shoe soles, and as food additive. Esters of adipic Acid are used as plasticizers for PVC (Polyvinyl Chloride) resins and lubricant component.

Adipic acid
Adipic acid (butane-1,4-dicarboxylic acid, C6H10O4) (Figure 27) is a white crystalline powder of C6-straight chain dicarboxylic acid, and is one of the most used chemicals in the world today (Table 1). It is slightly soluble in water and soluble in alcohol and acetone.

Adipic acid was first obtained by Dieterle and his colleagues in 1884 by oxidation of castor oil with nitric acid.

Adipic acid, despite its name (in Latin adipis is fat), is a product of the oxidative rancidity of fats (lipid peroxidation).

Adipic acid consumption is linked almost 90% to nylon (nylon-6.6) production by the polycondensation with 1,6-hexamethylenediamine. Adipic acid is used in manufacturing plasticizers, lubricant components, and polyester polyols for polyurethane systems. The acid and its derivatives are also used in the food industry (as gelling aid, acidulant, flavoring, leavening, and buffering reagents), and for the preparation of pesticides, dyes, textile treatment agents, fungicides, and pharmaceuticals (e.g., cephalosporin intermediates).

Presently, almost all of the commercial adipic acid is produced from cyclohexane, obtained by the hydrogenation of benzene, through two sequential oxidation processes.

Adipic acid, from an 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. About 60% of the 2.5 billion kg of adipic acid produced annually is used as monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming nylon 66. . Other major applications also involve polymers; it is a monomer for production of polyurethane and its esters are plasticizers.

Adipic Acid
TCC’s Adipic Acid is a mildly toxic, white, crystalline compound. The C6 straight-chain dicarboxylic acid is slightly soluble in water and soluble in alcohol and acetone. Nearly all commercial adipic acid is produced from cyclohexane.

Almost 90 percent of adipic acid produced is used in the production of nylon 66. The nylon, which has a protein-like structure, is further processed into fibers for applications in carpeting, automobile tire cord, and clothing. Adipic acid is also used to manufacture plasticizers and lubricant components.

Food grade adipic acid is used as a gelling aid, an acidulant, and as a leavening and buffering agent.

Applications
The majority of the 2.5 billion kg of adipic acid produced annually is used as a monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming 6,6-nylon. Other applications include some Polyurethanes. Esters of Adipic Acid, such as DOA (Di-2-Ethylhexyl Adipate) are used as plasticizers for PolyVinyl Chloride (PVC) resins.

Adipic acid has been incorporated into controlled-release tablets to obtain a pH-independent release for both weakly basic and weakly acidic drugs. It has also been incorporated into polymeric coatings of hydrophilic monolithic systems to modulate the pH, resulting in zero-order release of a hydrophilic drug.

In foods, small but significant amounts of adipic acid are used as a food ingredient as a flavorant and gelling aid. It is used in some calcium carbonate antacids to make them tart.

Abstract
Research efforts to find more sustainable pathways for the synthesis of adipic acid have led to the introduction of new catalytic processes for producing this commodity chemical from alternative resources. With a focus on the performance of oxygen and hydrogen peroxide as preferred oxidants, this minireview summarizes recent advances made in the selective oxidation of cyclohexene, cyclohexane, cyclohexanone and n-hexane to adipic acid. Special attention is paid to the exploration of catalytic pathways involving lignocellulosic biomass-derived chemicals such as 5-hydroxymethylfurfural, D-glucose, γ-valerolactone and compounds representative of lignin and lignin-derived bio-oils.

Adipic acid (AA), also referred to as hexanedioic acid, is one of the most produced commodity chemicals worldwide. With a projected global market size of more than 6 billion pounds by 2017,1 Adipic acid is known to be a versatile building block for an array of processes in the chemical, pharmaceutical and food industries.2 Its primary use is as a precursor for the synthesis of the polyamide Nylon-6,6. Additionally, Adipic acid is widely used for the production of polyester and polyurethane resins, as a plasticizer in the production of polyvinyl chloride (PVC) and polyvinyl butyral (PVB), and as an approved additive in cosmetics, gelatins, lubricants, fertilizers, adhesives, insecticides, paper and waxes. Notably, approximately 75 years after DuPont's development of the first commercial Adipic acid process,2 long-standing interest in the improvement of its synthesis strategy continues to inspire the catalytic community to explore new processes and resources.