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Adipic acid ( CASNO:124-04-9 )

Identification and Related Records
Name:
Adipic acid
CAS Registry number:
124-04-9
Iupac name:
hexanedioic acid
Synonyms:
FEMA No. 2011
Adipic acid
Hexane diacid
Heptanedoic
1, 4-Butanedicarboxylic acid
Adipinsaeure
Hexan-1,6-dicarboxylate
Kyselina adipova
Inipol DS
hexanedioic acid
1,4-butanedicarboxylic acid
Adipate
Hexanedioate
Adilactetten
Molten adipic acid
Acifloctin
1,6-Hexanedioic acid
Acinetten
EINECS(EC#):
204-673-3
Molecular Formula:
C6H10O4
Molecular Weight:
146.14
Inchi:
InChI=1/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
InChIKey:
WNLRTRBMVRJNCN-UHFFFAOYSA-N
Canonical SMILES:
C(CCC(=O)O)CC(=O)O
Chemical and Physical Properties
Appearance:
White crystalline powder.
Density:
1.36 g/cm3
Melting Point:
151-154℃(lit.)
Boiling Point:
337℃
Vapour:
1.81E-05mmHg at 25°C
Refractive Index:
1.439
Flash Point:
196℃
Water:
1.44 g/100 mL (15℃)
Solubilities:
1.44 g/100 mL (15℃) in water
methanol: 0.1 g/mL, clear, colorless
Color/Form:
Monoclinic prisms from ethyl acetate, water, or acetone and petroleum ether
Fine white crystals or powder
White solid
Colorless
Stability:
Stable. Substances to be avoided include ammonia, strong oxidizing agents.
HS Code:
29171210
Storage temp:
Keep away from sources of ignition. Store in a tightly closed container. Keep from contact with oxidizing materials. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep away from strong bases.
Spectral properties:
IR: 281 (Sadtler Research Laboratories Prism Collection)
MASS: 821 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
Intense mass spectral peaks: 55 m/z (100%), 41 m/z (55%), 100 m/z (46%), 45 m/z (37%)
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Computed Properties:
Molecular Weight:146.1412 [g/mol]
Molecular Formula:C6H10O4
XLogP3:0.1
H-Bond Donor:2
H-Bond Acceptor:4
Rotatable Bond Count:5
Exact Mass:146.057909
MonoIsotopic Mass:146.057909
Topological Polar Surface Area:74.6
Heavy Atom Count:10
Formal Charge:0
Complexity:114
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Anion Count:2
Feature 3D Hydrophobe Count:1
Effective Rotor Count:5
Conformer Sampling RMSD:0.6
CID Conformer Count:33
Safety and Handling
Hazard Codes:
Xi:Irritant
Risk Statements:
R36
Safety Statements:
S26
HazardClass:
9.2
Skin, Eye, and Respiratory Irritations:
Dust: Irritating to eyes, nose, and throat. Solid: Irritating to skin and eyes.
Cleanup Methods:
Environmental considerations- land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material.
SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner.
Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.
Environmental considerations- water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
Electrochemical measurements have been made on the system Cu(2+), adipic acid, nitric acid (which models the effluent from adipic acid plants) to investigate the reasons for the observed low current efficiency for copper deposition from such soln. The most probable cause is a cathodic shift in the deposition potential of copper making the reduction of NO3- the preferred process. Depletion experiments have been carried out on real effluent in two three-dimensional cells, a bipolar trickle tower and a porous reticulated carbon bed. Each performs reasonably well and, while the current efficiencies are low (about 20%), the deposition is essentially mass-transfer controlled.
Neutralizing agents for acids and caustics: Rinse with dilute soda ash solution.
Transport:
UN 9077
Fire Fighting Procedures:
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.
Fire Potential:
Combustible when exposed to heat or flame.
Formulations/Preparations:
GRADES: TECHNICAL; FCC
Grades of purity: Commercial, 99.8%
Food grades
Exposure Standards and Regulations:
Substance added directly to human food affirmed as generally recognized as safe (GRAS).
This substance is generally recognized as safe when used as a buffer and neutralizing agent in accordance with good manufacturing or feeding practice.
Adipic acid is an indirect food additive in polymer used as a basic component of single and repeated use food contact surfaces. Polyurethane resins (produced when one or more of the isocyanates listed in paragraph (a)(1) of this section is made to react with one or more of the substances listed in paragraph (a)(2) of this section in which adipic acid is included are approved for use on dry solids with the surface containing no free fat or oil (no end test required).
Adipic acid is an indirect food additive polymer for use as a basic component of single and repeated use food contact surfaces. Cross-linked polyester resins (produced by the condensation of one or more of the acids listed in paragraph (a)(1) of this section /in which adipic acid is included/ with one or more of the alcohols or epoxides listed in paragraph (a)(2) of this section, followed by copolymerization with one or more of the cross-linking agents listed in paragraph (a)(3) of this section), shall meet the following extractives limitations: net chloroform-soluble extractives not to exceed 0.1 mg/sq in of food contact surface tested when the prescribed food-simulating solvent is water or 8 or 50% alcohol; total nonvolatile extractives not to exceed 0.1 mg/sq in of food contact surface when solvent is heptane. In accordance with good manufacturing practice, finished articles containing the cross-linked polyester resins should be cleansed prior to first use in contact with food.
Reactivities and Incompatibilities:
Can react with oxidizing materials.
Other Preventative Measures:
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary.
Personnel protection: Avoid breathing vapors or dusts. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
Although there are no special precautions in the normal handling of adipic acid, good industrial housekeeping practices, personal hygiene, and avoidance of prolonged and repeated skin or eye contact is indicated.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Protective Equipment and Clothing:
Wear safety goggles, rubber gloves, as well as coveralls.
Personnel protection: Wear appropriate chemical protective gloves, boots and goggles.
Aprons should be used.
Octanol/Water Partition Coefficient:
log Kow= 0.08
Disposal Methods:
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Adipic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.
The following wastewater treatment technologies have been investigated for adipic acid: Biological treatment.
Landfill, incineration: Material can be burned in an approved incinerator. ...
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing
FROM CYCLOHEXANOL: BOUVEAULT, LOCQUIN, BULL SOC CHIM (4) 3: 438 (1908); ELLIS, ORG SYN COLL VOL (#1): 18 (2ND ED, 1941); FEAGEN, COPENHAVER, J AM CHEM SOC 62: 869 (1940); US PATENTS 2,191,786 (1940); 2,196,357 (1940); ZILBERMAN ET AL, J APPL CHEM (USSR) 29: 621 (1956).
BY ONE-STEP OXIDATION OF CYCLOHEXANE: ONOPCHENKO, SCHULZ, J ORG CHEM 38: 3729 (1973); TANAKA, 167TH AM CHEM SOC MEET (LOS ANGELES, MARCH-APRIL 1974) ABSTRACTS OF PAPERS, P 29. MANUFACTURER: FAITH, KEYES & CLARK'S INDUSTRIAL CHEMICALS, FA LOWENHEIM, MK MORAN, EDS (WILEY-INTERSCIENCE, NEW YORK, 4TH ED, 1975) PP 50-4.
Adipic acid can be prepared from acetylene and acetic acid in the presence of tert-butyl peroxide.
The predominant commercial route to adipic acid is via oxidation of cyclohexane in two processing steps. The first step involves oxidation of cyclohexane with air to form a mixture of cyclohexanone and cyclohexanol (termed ketone-alcohol, KA, or ol-one), followed by oxidation of the ketone-alcohol mixture with nitric acid to produce adipic acid. The balance of adipic acid is made from phenol by hydrogenation to cyclohexanol followed by similar nitric acid oxidation.
A patent describes a direct synthesis of adipic acid from butadiene by reaction under pressure with carbon monoxide and water (about 220 deg C) in the presence of a rhodium catalyst.
LAB PREPN FROM CYCLOHEXANONE: LF FIESER, ORGANIC EXPERIMENTS (HEATH, BOSTON, 1964) PP 106-8.

U.S. Exports
(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
(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
(1972) 6.77X10+11 G
(1975) 6.10X10+11 G
(1985) 5.90X10+11 g
(1990) 1.62 billion lb
(1991) 1.70 billion lb
(1992) 1.56 billion lb
(1993) 1.56 billion lb

Consumption Patterns
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).
Nylon 6,6 fibers, 79%; Nylon 6,6 plastics, 8%; Plasticizers and synthetic lubricants, 4%; Polyurethanes, 7%; Other (includes food) 2% (1984).
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%.
CHEMICAL PROFILE: Adipic acid. Demand: 1988: 1.64 billion lb; 1989: 1.65 billion lb; 1993 /projected/: 1.85 billion lb. (Includes exports, but not imports, which totaled 42 million lb last year.)
CHEMICAL PROFILE: Adipic acid, Demand: 1.8 billion pounds, 1994; 1.85 billion pounds, 1995; 2 billion pounds /projected/, 1999 (Demand is for the US and includes exports, which were 125 million pounds in 1994, but not imports which were 110 million pounds.)
CHEMICAL PROFILE: Adipic acid, Uses: Nylon 6/6, 85 % (fibers, 75%; resins, 10%); polyurethane resins, 8%; plasticizers, 3%; miscellaneous, including unsaturated polyester resins and food applications, 4%.
Usage:
Raw material for pharmaceuticals, perfume fixative.
Biomedical Effects and Toxicity
Biomedical Effects and Toxicity:
When ingested, it is apparently only partially metabolized in the human system, the balance being eliminated unchanged in the urine.
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 26(SRC), determined from a measured log Kow of 0.08(2) and a recommended regression-derived equation(3), indicates that adipic acid is expected to have very high mobility in soil(SRC). Volatilization of adipic acid is not expected to be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 4.7X10-12 atm-cu m/mole(SRC) from its extrapolated vapor pressure, 7.4X10-7 at 30 deg C(4), and measured water solubility, 3.0X10+4 mg/l at 30 deg C(5). Adipic acid is not expected to volatilize from dry soil surfaces based on its extrapolated vapor pressure(4). Biodegradability screening tests indicate that adipic acid is readily biodegradable(SRC). An 84% conversion of adipic acid's carbon content to carbon dioxide was observed after 30 days aerobic incubation in soil biometer flasks at an initial adipic acid concn of 1 mg/g soil(6).
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 26(SRC), determined from a measured log Kow of 0.08(2) and a recommended regression-derived equation(3), indicates that adipic acid is not expected to adsorb to suspended solids and sediment in water(SRC). Adipic acid is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 4.7X10-12 atm-cu m/mole(SRC) from its extrapolated vapor pressure, 7.4X10-7 mm Hg at 30 deg C(4), and measured water solubility, 3.0X10+4 mg/l at 30 deg C(5). Adipic acid's pKa's of 4.44 and 5.4(6) indicate that adipic acid will exist predominately in the ionized form under environmental pHs(SRC). Volatilization of the ionized form from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(7), an estimated BCF value of 0.68(3,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Biodegradability screening tests indicate that adipic acid is readily biodegradable(SRC). Adipic acid was rapidly degraded in a river die-away test using Main River (Germany) water; 50% and 90% degradation being achieved in 3.5 and 7 days, respectively, at concn levels of 700 mg/l(8).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), adipic acid, which has an extrapolated vapor pressure of 7.4X10-7 mm Hg at 30 deg 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 about 2.9 days(3,SRC). Particulate-phase adipic acid may be physically removed from the air by wet and dry deposition(SRC).
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