1,6-HEXANEDIOIC ACID

1,6-HEXANEDIOIC ACID - Names and Identifiers

Name	Adipic acid
Synonyms	ADIPIC ACID Adipic acid hexanedioate adipinic acid Hexanedioic acid AKOS BBS-00004308 Refined adipic acid RARECHEM AL BO 0180 DICARBOXYLIC ACID C6 1,6-HEXANEDIOIC ACID 1,4-BUTANEDICARBOXYLIC ACID BUTANE-1,4-DICARBOXYLIC ACID 1,4-Butanedicarboxylic acid~Hexanedioic acid
CAS	124-04-9
EINECS	204-673-3
InChI	InChI=1/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)/p-2
InChIKey	WNLRTRBMVRJNCN-UHFFFAOYSA-N

1,6-HEXANEDIOIC ACID - Physico-chemical Properties

Molecular Formula	C6H10O4
Molar Mass	146.14
Density	1,36 g/cm3
Melting Point	151-154°C(lit.)
Boling Point	265°C100mm Hg(lit.)
Flash Point	385°F
JECFA Number	623
Water Solubility	1.44 g/100 mL (15 ºC)
Solubility	methanol: 0.1g/mL, clear, colorless
Vapor Presure	1 mm Hg ( 159.5 °C)
Vapor Density	5 (vs air)
Appearance	Solid
Color	White
Exposure Limit	ACGIH: TWA 5 mg/m3
Merck	14,162
BRN	1209788
pKa	4.43(at 25℃)
PH	3.74(1 mM solution);3.22(10 mM solution);2.71(100 mM solution);
Storage Condition	Store below +30°C.
Stability	Stable. Substances to be avoided include ammonia, strong oxidizing agents.
Refractive Index	1.4880
Physical and Chemical Properties	Character: white crystal, with the smell of burning bone. solubility: slightly soluble in water, soluble in most organic solvents such as alcohol and ether.
Use	Used as a raw material for the synthesis of high polymers, but also for the preparation of plasticizers and lubricants

1,6-HEXANEDIOIC ACID - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	R36 - Irritating to the eyes R41 - Risk of serious damage to eyes
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S24/25 - Avoid contact with skin and eyes.
WGK Germany	1
RTECS	AU8400000
TSCA	Yes
HS Code	29171210
Toxicity	LD50 orally in Rabbit: 5700 mg/kg LD50 dermal Rabbit > 7940 mg/kg

1,6-HEXANEDIOIC ACID - Upstream Downstream Industry

Raw Materials	Cyclohexanol Cyclohexanone Copper Vanadium pentoxide Nitric acid
Downstream Products	2,5-thiophenedicarboxylic acid Adipic acid monoethyl ester Monostearin 1,4-Dicyanobutane Nylon 6\|6 Polyurethane

1,6-HEXANEDIOIC ACID - Nature

Open Data Verified Data

white crystals, with the smell of burning bones. Melting point 153 °c. The boiling point of 332.7 deg C (lOlkPa decomposition). The relative density was 1. 360. Flash point (Open Cup) 209. 85 °c. Ignition point (Open Cup) 231. 85 °c. Melt viscosity 4. 54mPa -s(160 ℃). Slightly soluble in water, soluble in alcohol, ether and other most organic solvents.

Last Update：2024-01-02 23:10:35

1,6-HEXANEDIOIC ACID - Preparation Method

Open Data Verified Data

cyclohexane oxidation cyclohexane is oxidized to cyclohexanol and cyclohexanone in the first step under the action of cobalt catalyst, and the reaction conditions are 150-160 ℃,810-1013 kPa. Cyclohexanol and cyclohexanone were oxidized by nitric acid to adipic acid. The reaction conditions were 60~80 ℃,100 ~ 400kPa. The crude product was refined by recrystallization to obtain a finished product.
two-step carbonylation of butadiene with butadiene and carbon monoxide as raw materials, the first butadiene into 3 pentenoic acid methyl ester, and then by carbonylation of dimethyl adipate, and finally obtained by hydrolysis.
cyclohexene-water-in-one oxidation method cyclohexene is obtained by partial hydrogenation of benzene using benzene and hydrogen as raw materials, and cyclohexanol is produced by hydration, and cyclohexanol is oxidized with nitric acid to produce adipic acid.

Last Update：2022-01-01 10:31:53

1,6-HEXANEDIOIC ACID - Use

Open Data Verified Data

The primary use is as a raw material for Nylon 66 and engineering plastics. The second is for the production of various ester products, used as plasticizers and advanced lubricants. In addition, adipic acid is also used as a raw material for polyurethane elastomers, an acidifying agent for various foods and beverages, which sometimes outperforms citric acid and tartaric acid. Adipic acid is also a raw material for medicine, yeast purification, pesticides, adhesives, synthetic leather, synthetic dyes and fragrances.

Last Update：2022-01-01 10:31:52

1,6-HEXANEDIOIC ACID - Safety

Open Data Verified Data

adipic acid is stable with low toxicity. Can be used with citric acid or tartaric acid, not deliquescent.
it was packed in a plastic-lined woven bag with a net weight of 25kg. Storage in a dry and cool place, should pay attention to the rain when transport. According to the general provisions of the storage and transportation of chemicals.

Last Update：2022-01-01 10:31:53

1,6-HEXANEDIOIC ACID - Reference Information

FEMA	2011 \| ADIPIC ACID
LogP	0.09 at 25℃
NIST chemical information	Information provided by: webbook.nist.gov (external link)
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
Introduction	Adipic acid, also known as fat acid, is a carboxylic acid organic compound that can be used as a chemical reagent, and also used in plastics and organic synthesis.. It is a white crystalline powder, slightly soluble in water, and acidic when dissolved in water. Adipic acid, as the basic unit of a variety of chemical products, is by far the most important aliphatic dicarboxylic acid in industrial production. About 3 million tons of adipic acid are used to synthesize nylon -66 monomer every year worldwide. In addition, adipic acid is also used to synthesize polyester, polyurethane, lubricant, plasticizer, adiponitrile, and gelling additives used as seasoning in food.
Application	Adipic acid is the most valuable diacid in aliphatic diacids. Adipic acid has the generality of aliphatic dibasic acid, including salt formation reaction, esterification reaction, amidation reaction, etc. The main use of adipic acid is as a raw material for three major categories of products, namely: synthetic nylon 66 salt, and then manufacture polyamide resin and fiber (nylon 66). Nylon 66 is the largest end market for adipic acid; synthetic polyester polyol, Used in the production of polyester polyurethane; adipic acid diester plasticizer. In addition, it can also be used to produce advanced lubricating oil and food additives (sour agents for food and beverage).
preparation method	74mmol cyclohexane, 7ml of solvent butanone (mass ratio of cyclohexane to butanone is 1.1:1), 33mg of activated carbon supported nano-gold catalyst (mass fraction of Au is 1. 25%; The mass ratio of cyclohexane to catalyst is 188. 7:1),0. 7mmol initiator cyclohexanone (mass ratio of cyclohexane to cyclohexanone is 90. 6:1), magnetic stirrer, magnetic stirring is started, oxygen is introduced at 130°C, oxygen pressure is maintained at 1. 5MPa, and cooled to room temperature after 8 hours of reaction. Centrifugal separation to obtain the activated carbon supported nano-gold catalyst and the reaction liquid, take a little part of the reaction liquid for the result detection, and the rest of the reaction liquid is extracted with deionized water for three times to obtain the oil phase and the water phase, and the water phase is cooled at 0°C for 12 hours to obtain the adipic acid crystalline solid; the oil phase is swirled in vacuum, the initiator cyclohexanone is collected, and it is returned to the reaction kettle for re-reaction; the activated carbon supported nano-gold catalyst is washed with acetone for three, after drying at 120°C for 5 hours, it is recycled.
content analysis	in a 250ml conical flask with glass plug, transfer about 3g of accurately weighed sample, add 50ml of methanol, dissolve carefully in a steam bath, cool, add several drops of phenolphthalein test solution (TS-167), titrate with 1mol/L sodium hydroxide to the reddish end point and maintain for 30s. At the same time, a blank test was made. Each mL1mol/L sodium hydroxide is equivalent to 73.07mg adipic acid.
toxicity	LD50 orally in Rabbit: 5700 mg/kg LD50 dermal Rabbit > 7940 mg/kg
usage limit	GB 2760-96: solid beverage, 0.01 g/kg; Chewing gum 4.0 mg/kg; Jelly powder, 0.15 g/kg (calculated as diluted 6 times); Spices for food. FDA,§ 184.1009(1994): Baked foods, 0.05%; Alcohol-free beverages, 0.005%; Seasonings, 5.0%; Dairy products, 0.45%; Oil 0.3%; Frozen milk sweets, 0.0004%; Gelatin and pudding, 0.55%; Gravy, 0.1%; Meat products, 0.3%; Snacks, 1.3%; Other foods, 0.02%. FEMA(mg/kg): soft drink 40, pudding 5000.
use	is mainly used as a raw material for nylon 66 and engineering plastics, is also used to produce various ester products, and is also used as a raw material for polyurethane elastomer adipic acid has a soft and durable sour taste, has little change in Ph value in a larger concentration range, and is a better Ph value regulator. It can be used for jelly powder and solid beverage powder with maximum usage of 0.15 g/kg and 0.01 g/kg respectively. It is mainly used as raw material for nylon 66 and engineering plastics. The second is for the production of various ester products, used as plasticizers and advanced lubricants. In addition, adipic acid is also used as a raw material for polyurethane elastomers, an acidifying agent for various foods and beverages, and its effect is sometimes better than citric acid and tartaric acid. Adipic acid is also a raw material for medicine, yeast purification, pesticides, adhesives, synthetic leather, synthetic dyes and fragrances. Used as a chemical reagent, also used in plastics and organic synthesis Used as a raw material for synthesizing polymers, and also used for making plasticizers and lubricants Organic synthesis, flux, resin, plastic.
production method	in nature, adipic acid exists in sweet radish.. Other production methods of adipic acid include: chlorocyclohexane method, recovery of adipic acid from cyclohexane oxidation by-products, production of adipic acid from acrylate, etc. Asahi Kasei Japan also carried out one-step air oxidation of cyclohexane to adipic acid research. I cyclohexane one-step oxidation method uses cyclohexane as raw material, acetic acid as solvent, cobalt and bromide as catalyst, at 2MP. and reaction at 90 ℃ for 10~13h. The yield is 75%. 2 Cyclohexane stepwise oxidation method (1) The preparation of KA oil can be directly oxidized with air at 1.0~2.5MPa and 145~180 ℃, with a yield of 70% ~ 75%. Metaboric acid can also be used as a catalyst for air oxidation at 1.0 ~ 2.0MPa and 165 ℃, and the yield can reach 90%, and the alcohol-ketone ratio is 10:1; the reactant is treated with hot water, which can hydrolyze and delaminate the ester, and the water layer Recover boric acid, which is dehydrated into metaboric acid for recycling; the organic layer is saponified with caustic soda, and the acid is removed, and the alcohol-ketone mixture is obtained after cyclohexane is recovered by distillation. (2) oxidation of KA oil with excess 50% ~ 60% nitric acid in a two-stage series reactor, at 60~80 ℃ and 0.1 ~ 0.4MPa oxidation of KA oil. The catalyst is copper-vanadium system (copper 0.1% ~ 0.5%, vanadium 0.1% ~ 0.2%), and the yield is 92% ~ 96% of the theoretical value. After the reactants are steamed out of nitric acid, high-purity adipic acid can be obtained through two crystallization and refining.
category	flammable liquid
toxicity classification	poisoning
acute toxicity	oral administration-rat LDL0: 273 mg/kg; Oral administration-mouse LD50: 1900 mg/kg
stimulation data	eye-rabbit 20 mg/24 hours moderate
flammability hazard characteristics	combustible in case of open flame, high temperature and strong oxidant; Combustion emission stimulates smoke
storage and transportation characteristics	complete packaging, light loading and unloading; warehouse ventilation, away from open flames, high temperature, separate storage from oxidant
fire extinguishing agent	foam, dry powder, carbon dioxide, sand
occupational standard	STEL 4 mg/m3
auto-ignition temperature	788 °F
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)