Adipic Acid

HCID 196CAS 124-04-9

Basic information

Standard SMILES
O=C(O)CCCCC(=O)O
InChIKey
WNLRTRBMVRJNCN-UHFFFAOYSA-N
Molecular formula
C6H10O4
Average molar mass
146.14 g/mol
Monoisotopic mass
146.0579088

Names & identifiers

Preferred name
Adipic Acid
IUPAC
hexanedioic acid

Names & synonyms

adipic acidhexanedioic acid124-04-9Adipinic acid1,4-Butanedicarboxylic acidAdilactettenAcifloctinAcinetten1,6-Hexanedioic acidMolten adipic acidKyselina adipovaFEMA No. 2011
Show more names
AdipinsaureAcide adipiqueAdipidic acidDTXSID7021605NSC-762276A0JE0FKJINS NO.355AI3-03700

Database identifiers

CAS
124-04-9
PubChem CID
196
DTXSID
DTXSID7021605
ChEMBL
CHEMBL1157
ChEBI
CHEBI:30832
UNII
76A0JE0FKJ
EC Number
204-673-3
Nikkaji
J10.057I

Properties

Computed structural properties

XLogP
0.1
Topological polar surface area
74.6 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
10

Experimental & physicochemical properties

pHpH of saturated aqueous solution at 25 °C = 2.7; pH of 0.1% solution at 25 °C = 3.2
LogP · 3 items

log Kow = 0.08

0.08

0.08

OdorOdorless
Taste · 2 items

TART TASTE

Sour tasting

Density · 5 items

1.36 at 68 °F (USCG, 1999) - Denser than water; will sink

1.360 g/cu cm at 25 °C

Bulk density: 640-800 kg/cu m

1.36 g/cm³

1.36

ViscosityViscosity of melt: 4.54 cP at 160 °C; 2.64 cP at 193 °C

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (2 of 5531) of reports.

Hazard information

Regulatory Information · 4 items

Chemical: Hexanedioic acid

Hexanedioic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexanedioic acid are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 18-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15464

Hexanedioic acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Hexanedioic acid: Human health tier II assessment;IMAP assessments - Hexanedioic acid: Environment tier I assessment
DOT LabelClass 9
Fire Hazards · 2 items

Behavior in Fire: Melts and may decompose to give volatile acidic vapors of valeric acid and other substances. Dust may form explosive mixture with air. (USCG, 1999)

Combustible. Finely dispersed particles form explosive mixtures in air.

Fire PotentialCombustible when exposed to heat or flame ...
Health HazardsInhalation of vapor irritates mucous membranes of the nose and lungs, causing coughing and sneezing. Contact with liquid irritates eyes and has a pronounced drying effect on the skin; may produce dermatitis. (USCG, 1999)

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:;CAUTION: Fire involving Safety devices (UN3268) and Fire suppressant dispersing devices (UN3559) may have a delayed activation and a risk of hazardous projectiles. Extinguish the fire at a safe distance.;SMALL FIRE: Dry chemical, CO2, water spray or regular foam.;LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.;FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Rest. Refer for medical attention .

First AidINHALATION: remove victim to fresh air; get medical attention if irritation persists.;EYES: flush with water for at least 15 min.;SKIN: flush with water. (USCG, 1999)
Exposure Control and Personal Protection2.0 [mg/m3], inhalable fraction of the aerosol[German Research Foundation (DFG)]
Fire Fighting Procedures · 4 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Wear self-contained breathing apparatus for firefighting if necessary.

Stop discharge if possible, keep people away. Shut off ignition sources. Call fire department. Avoid contact with solid and dust. Isolate and remove discharged material.

If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.

Storage Conditions · 2 items

Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Non Combustible Solids.

Storage temperature: ambient; venting: open

Toxicology

Interactions · 1 item

A group of mice received intravaginally, three time weekly, applications of a powdered mixture containing urea, adipic acid, and carboxymethyl cellulose. There was a high incidence of vaginal cancer after prolonged treatment. Experiments extended over one year, in which the three ingredients were given separately, yielded no tumors.

Ecotoxicity Values · 5 items

LC50; Species: Lepomis machrochirus (bluegill sunfish); Concentration: = < 330 mg/L for 24 hr /Conditions of bioassay not specified/

LC50; Species: Pimephales promelas (fathead minnow); Conditions: /static bioassay/; Concentration: >300 mg/L for 1 hr

LC50; Species: Pimephales promelas (fathead minnow); Conditions: /static bioassay/; Concentration: 172 mg/L for 24 hr

LC50; Species: Pimephales promelas (fathead minnow); Conditions: /static bioassay/; Concentration: 97 mg/L for 72-96 hr

For more Ecotoxicity Values (Complete) data for ADIPIC ACID (6 total), please visit the HSDB record page.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from a structure estimation method(2), indicates that adipic acid is expected to have very high mobility in soil(SRC). The pKa values of adipic acid's two acid groups are 4.44 and 5.44(3), indicating that this compound will exist almost entirely in the anion form and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of adipic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-12 atm-cu m/mole(SRC) based upon its vapor pressure, 2.27X10-7 mm Hg(5), and water solubility, 2.43X10+4 mg/L(6). Adipic acid is not expected to volatilize from dry soil surfaces based on its vapor pressure(5). Biodegradation screening tests indicate that adipic acid is readily biodegradable in soil and water(7). An 84% conversion of adipic acid's carbon content to carbon dioxide was observed after 30 days aerobic incubation in a soil flask test(8).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from a structure estimation method(2), indicates that adipic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.8X10-12 atm-cu m/mole(SRC), derived from its vapor pressure, 2.27X10-7 mm Hg(4), and water solubility, 2.43X10+4 mg/L(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow of 0.08(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation screening tests indicate that adipic acid is readily biodegradable in soil and water(8). Adipic acid was rapidly degraded in a river die-away test using Main River (Germany) water with 50% and 90% degradation being achieved in 3.5 and 7 days, respectively, at concentration levels of 700 mg/L(9). Adipic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), adipic acid, which has a vapor pressure of 2.27.4X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase adipic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.9 days(SRC), calculated from its rate constant of 5.6X10-12 cu cm/molecule-sec at 25 °C that was derived using a structure estimation method(3). Particulate-phase adipic acid may be physically removed from the air by wet and dry deposition(SRC). Adipic acid has been detected in snow, sleet and rain precipitation(4).

Food Survey Values · 1 item

Aerosol emission rates of adipic acid from frying hamburger meat was 1.6 mg/kg of meat cooked; emission rates from charbroiling hamburger was 9.1 mg/kg of meat cooked for extra-lean hamburger (approx. 10.0% fat) and 17.2 mg/kg of meat cooked for regular hamburger (approx. 21% fat)(1). An adipic acid emission rate of 200 mg/kg of meat cooked was reported for charbroiling(2). An adipic acid concentration of 15-129 ng/kg was reported for the fine particulate material emitted from Chinese cooking(3).

Adverse EffectsAsthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol.

Regulatory information

Regulatory Information · 4 items

Chemical: Hexanedioic acid

Hexanedioic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexanedioic acid are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 18-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15464

Hexanedioic acid: Does not have an individual approval but may be used under an appropriate group standard

FDA Requirements · 2 items

Substance added directly to human food affirmed as generally recognized as safe (GRAS).

Adipic acid used as a buffer and neutralizing agent in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

Atmospheric Standards · 1 item

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Adipic acid is produced, as an intermediate or final product, by process units covered under this subpart.

CERCLA Reportable Quantities · 1 item

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act Requirements · 1 item

Adipic acid is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

Radioactive adipic acid was fed to fasted experimental rats and the metabolic products identified in the urine were urea, glutamic acid, lactic acid, beta-ketoadipic acid, and citric acid. The presence of beta-ketoadipic acid provided some evidence that adipic acid is metabolized by beta-oxidation in much the same fashion as fatty acids. Further evidence was provided by the appearance of succinate in the urine of rats fed radioactive (14)C-adipic acid and injected with malonic acid. The presence of radioactive acetyl-gamma-phenyl-alphaaminobutyric acid after feeding gamma-phenyl-alpha-aminobutyric acid and (14)C-labeled adipic acid provided very strong evidence that acetate is a metabolite of adipic acid. Radioactive glycogen was isolated following feeding of glucose and radioactive adipic acid.

Adipic acid is metabolized via beta-oxidation to succinic and acetic acids, and subsequently to other normal intermediary metabolites.

Absorption, Distribution and Excretion · 2 items

Absorbed adipic acid is primarily excreted in the urine unchanged or in the breath of carbon dioxide.

In man following ingestion, adipic acid is only partially metabolized; the balance is eliminated unchanged in the urine.

Tissue LocationsKidney;Liver
Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 6 items

CIR ingredient: Adipic Acid

Used to make nylon, polyurethane foams, lubricants, and plasticizers; Used in adhesives, baking powder, and food flavoring; [ACGIH]

The major markets for adipic acid include use as feedstocks for nylon 6,6 resins and fibers, polyester polyols and plasticzers.

... Applications documented for adipic acid are as a lubricant additive in coatings, and foams, and in shoe soles, as tanning agent in leather industry, pH regulator in processes such as in the production of cleaning agents, pelletizing agent in disinfectant pills for drinking water, additive in flue gas sulfurization, in the coating of dishwashing machine tablets and as an additive in chemicals

... As an acidulant in dry powdered food mixtures, especially in those products having delicate flavors & where addition of a tang to the flavor is undesirable.

/Adipic acid/ 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 ... For concentrations /of adipic acid ranging/ from 0.5-2.4 g/100 mL, the pH ... varies less than half a unit. ... pH is low enough to inhibit browning of most fruits and other foodstuffs.

U.S. Exports · 5 items

(1972) 1.95X10+9 G

(1975) 4.40X10+9 G

(1984) 2.52X10+10 g

(1987) 3,510,252 lb

CHEMICAL PROFILE: Adipic acid, Exports: 125 million pounds (1994)

U.S. Imports · 5 items

(1972) 7.72X10+8 G

(1975) 4.3X10+8 G

(1984) 4.38X10+9 g

(1986) 12,356,621 lb

CHEMICAL PROFILE: Adipic acid, Imports: 110 million pounds (1994)

U.S. Production · 6 items

2023: 1,000,000,000 - <2,500,000,000 lb;2022: 1,000,000,000 - <2,500,000,000 lb;2021: 1,000,000,000 - <2,500,000,000 lb;2020: 1,000,000,000 - <2,500,000,000 lb

(1972) 6.77X10+11 G

(1975) 6.10X10+11 G

(1985) 5.90X10+11 g

(1990) 1.62 billion lb

For more U.S. Production (Complete) data for ADIPIC ACID (10 total), please visit the HSDB record page.

Consumption Patterns · 5 items

80% FOR NYLON 6,6 FIBERS; 5% FOR NYLON 6,6 PLASTICS; 4% FOR POLYURETHANE RESINS; 4% FOR PLASTICIZERS AND SYNTHETIC LUBRICANTS; 0.5% FOR FOOD ADDITIVES; 0.5% FOR MISC APPLICATIONS INCLUDING POLYESTER RESINS (1971).

CHEMICAL PROFILE: Adipic acid. Total nylon 66, 87% (reactant for nylon 66 fibers, 77%; reactant for nylon 66 resins, 10%); polyurethane resins, 4%: plasticizers, 3%; miscellaneous including food and polyester resin uses, 2%; exports, 3%.

CHEMICAL PROFILE: Adipic acid. Demand: 1985: 1.5 billion lb; 1986: 1.68 billion lb; 1987: 1.66 billion lb.

CHEMICAL PROFILE: Adipic Acid. Total nylon 6/6, 88% (reactant for nylon 6/6 fibers, 77%; reactant for nylon 6/6 resins, 11%); polyurethane resins, 3%; plasticizers, 2.5%; exports, 4.5%: miscellaneous, including food and polyester resin uses, 2%.

For more Consumption Patterns (Complete) data for ADIPIC ACID (8 total), please visit the HSDB record page.

Consumer UsesSurfactant (surface active agent);Anti-freeze agent;Solvent;Other;Intermediate;Not Known or Reasonably Ascertainable

Related reactions

256 records

Linked notes

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