Adipic acid

146.14

146.05790880

204-673-3

76A0JE0FKJ

0369

760121|7622

3077

DTXSID7021605

Monoclinic prisms from ethyl acetate, water, or acetone and petroleum ether|White monoclinic prisms|White crystalline solid|Colorless

2917120001

0.08 (LogP)|log Kow = 0.08|0.08

1.36 at 68 °F (USCG, 1999)|1.360 g/cu m at 25 °C|Bulk density: 640-800 kg/cu m|1.36 g/cm³|1.36

304 °F (USCG, 1999)|153.2 °C|151,5-154,0 °C|151.5 °C|151-154°C|152 °C|304°F

337.5 °C|337.5 °C at 760 mm Hg: 265 °C at 100 mm Hg: 240.5 °C at 40 mm Hg: 222 °Cat 20 mm Hg: 205.5 °C at 10 mm Hg; 191 °C at 5 mm Hg; 159.5 °C at 1.0 mm Hg|265.00°C.@100.00mmHg|338 °C

376 °F Combustible solid (USCG, 1999)|385 °F, 196 °C (closed cup)|196 °C c.c.|376°F

Slightly soluble in water. Freely soluble in ethanol|In water, 3.00X10+4 mg/L at 30 °C|In water, 0.633/100 parts (wt/wt) ether at 19 °C|In water, 160 g/100 mL boiling water|1.4 g/100 mL water at 10 °C|For more Solubility (Complete) data for ADIPIC ACID (7 total), please visit the HSDB record page.|30.8 mg/mL at 34 °C|Solubility in water, g/100ml at 15 °C: 1.4 (moderate)|slightly soluble in water; soluble in alcohol and acetone

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

3.18e-07 mmHg|3.02X10-5 Pa at 25 °C (2.27X10-7 mm Hg)|Vapor pressure, Pa at 18.5 °C: 10

5.04 (Air = 1)|Relative vapor density (air = 1): 5.04

Odorless

TART TASTE|Sour tasting

Henry's Law constant = 1.8X10-12 atm-cu m/mole at 25 °C (est)

K1 = 3.90X10-5 at 25 °C; K2 = 5.29X10-6 at 25 °C|pKa1 = 4.43; pKa2 = 5.41|pKa1 = 4.44 at 25 °C; pKa2 = 5.44 at 25 °C|pKa1 = 4.418; pKa2 = 5.412 at 25 °C

129.61 Ų [M+Na-2H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|132.4 Ų [M-2H+Na]-

PRACTICALLY NON-HYGROSCOPIC|Conversion factors at 25 °C: 1 ppm = 5.96 mg/cu m; 1 mg/cu m = 0.168 ppm (calc)|Heat of fusion 57 cal/g= 238.49 J/g= 34.853 J/mol|Specific heat of the liquid = 2.253 kJ/kg K; specific heat of the vapor (at 300 °C) = 1.680 kJ/kg K; heat of fusion = 115 kJ/kg|For more Other Experimental Properties (Complete) data for ADIPIC ACID (6 total), please visit the HSDB record page.

Dust may form explosive mixture with air (USCG, 1999). Insoluble in water.

Acids, Carboxylic

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 it 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.

788° F; 450° F (USCG, 1999)|788 °F, 420 °C|422 °C

-2800 kJ/mol

In air: (dust) 10-15 mg/l

Dust explosion possible if in powder or granular form, mixed with air. If dry, it can be charged electrostatically by swirling, pneumatic transport, pouring, etc.

Corrosion rate for ASTM grade 2 Titanium: 0.0 mm/yr at 232 °C for 67% (wt) concn.|Aqueous solutions of adipic acid are corrosive.

549 kJ/kg

AU8400000

Stable under recommended storage conditions.|RELATIVELY STABLE

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material.|Contaminated packaging: Dispose of as unused product.|Adipic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.|For more Disposal Methods (Complete) data for ADIPIC ACID (6 total), please visit the HSDB record page.

Incompatible materials: Strong oxidizing agents.|Can react with oxidizing materials.

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.

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.

|Warning|H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|H319 (97.04%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|Aggregated GHS information provided by 5501 companies from 10 notifications to the ECHA C&L Inventory.|Danger|H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]|P261, P271, P280, P304+P340, P305+P351+P338, P310, P312, P403+P233, P405, and P501|P273, P280, P305+P351+P338, P310, and P501|P261, P264, P271, P273, P280, P304+P340, P305+P351+P338, P312, P337+P313, P403+P233, P405, and P501|H316: Causes mild skin irritation [Warning Skin corrosion/irritation]|P260, P261, P264, P270, P271, P280, P304+P312, P304+P340, P305+P351+P338, P312, P314, P332+P313, P337+P313, P403+P233, P405, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Normal protection against exposure to finely divided organic solids (rubber gloves, plastic goggles) (USCG, 1999)|Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Handle with gloves.|Body Protection: Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|For more Personal Protective Equipment (PPE) (Complete) data for ADIPIC ACID (6 total), please visit the HSDB record page.

Combustible when exposed to heat or flame ...

Dust may form explosive mixture with air.|The principal hazard in the handling of adipic acid is the danger of dust explosions. Minimum explosive concentration (dust) is 0.010-0.015 g/L.

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.

Accidental release measures. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.; Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.|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.

Precautions for safe handling: Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|If material not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary.|For more Preventive Measures (Complete) data for ADIPIC ACID (9 total), please visit the HSDB record page.

Dust: Irritating to eyes, nose, and throat. Solid: Irritating to skin and eyes.

Sweep spilled substance into covered plastic containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.

The substance is irritating to the eyes and respiratory tract. Inhalation of the aerosol may cause asthmatic reactions.

Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. Prevent build-up of electrostatic charges (e.g., by grounding).

PREVENT DISPERSION OF DUST! STRICT HYGIENE!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

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.

| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.| 1 - Materials that, under emergency conditions, can cause significant irritation.

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).

Adipic acid was detected in effluents from advanced treatment plants in Pomona, CA and Lake Tahoe, CA(1). Motor exhaust of two automobiles contained 1.07 and 4.75 ug/cu m of adipic acid(2). Adipic acid was detected in process retort water from the Occidental Oil Shale, Inc facility in Logan Wash, CO at a concentration of 4.7 mg/L(3). Groundwater samples contaminated by industrial pollution near Barcelona, Spain were found to contain adipic acid at concentrations ranging from <5 to 130 ng/L(4). Adipic acid was detected in both particulate phase and gas phase emissions from various biomass and wood burning fuels(5); gas phase emission from burning Ponderosa Pine was 3.52 mg/kg of biomass burned(5).

Soil samples taken at the University of California, Los Angeles campus contained 215 and 568 ppb of adipic acid whereas bog sediment samples from the Sierra Nevada foothills contained 2050 ppb(1).

URBAN/SUBURBAN: The concentration of adipic acid in nine 2 hr air samples taken on July 24, 1973 during a smog episode in West Covina, CA (30 km east of Los Angeles) ranged from 1.5 to 8.9 ug/cu m(1); the concentration peaked in mid-afternoon, coincident with the peak in ozone concentration, suggested that it was formed by photochemical reaction of cycloalkene or diolefin precursor(1). The diurnal variation of adipic acid in aerosol samples from Pasadena, CA was 0.04 to 0.78 ug/cu m with the peak concentration occurring shortly before noon(2). A suburban area of Japan had an atmospheric adipic acid concentration of 10 ng/cu m(3). The concentration of adipic acid in aerosol samples from West Los Angeles and Los Angeles, CA were 12 to 484 and 29 to 92 ng/cu m, respectively(4); dust samples from these areas contained 11.4 and 5.90 ppm of adipic acid, respectively(4). Aerosol samples collected from Tokyo, Japan in Feb and July 1992 contained adipic acid at concentrations ranging from 31 to 79 ng/cu m(5). Aerosol samples collected from Tokyo, Japan in 1988-89 contained adipic acid at an concentrations ranging from 2.6 to 55 ng/cu m(6). The ambient concentration of adipic acid in West Los Angeles, CA in Oct. 1982 was 7.9 ng/cu m(7). The average ambient annual concentration of adipic acid in fine particles collected from West Los Angeles, downtown Los Angeles, Pasadena, Rubidoux, and San Nicolas Island, CA in 1982 was 15.0, 14.1, 14.1, 24.3, and <0.02 ng/cu m, respectively(8). Average adipic acid concentrations ranged from 5.47-88.5 ng/cu m in PM10 aerosol samples collected at 12 sites in southern California during 1995 monitoring(9).|RURAL/REMOTE: The average daytime concentration of adipic acid in air samples collected from Takasaki and Karuizawa, Japan in July 1986 was 11.3 and 3.8 ng/cu m, respectively(1). The average concentration of adipic acid in airborne aerosols collected from Takasaki and Karuizawa, Japan in July 1986 was 5.2 and 2.3 ng/cu m, respectively(2). Remote aerosol samples collected over the North Pacific Ocean in May 1986 contained adipic acid at a concentration of 0.039 ng/cu m(3). Adipic acid was detected in PM2.5 aerosol samples collected in the summer of 2003 in the southeastern US(4); occurrence of the adipic acid in the aerosol samples may have due to atmospheric photooxidation of d-limonene as demonstrated in smog chamber tests(4). Several monitoring studies indicated that the global background level of adipic acid in atmospheric aerosol ranged from 0.9-7.9 ng/cu m with the lowest value occurring in Antarctica(5). Atmospheric aerosol samples collected between July 15 to August 25, 1995 at the Great Smoky Mountain National Park in rural Tennessee contained daytime adipic acid concentrations of 2.1-18.7 ng/cu m with no adipic acid detected during night-time sampling(6).

Adipic acid was detected in the organic film collected from indoor and outdoor glass windows at five sites in greater Toronto Canada during July 2000 sampling(1). Adipic acid has identified as a component of tobacco smoke(2).

IDENTIFICATION AND USE: Adipic acid is white crystalline solid. The major markets for adipic acid include use as feedstocks for nylon 6,6 resins and fibers, polyester polyols and plasticzers. Nylon 6,6 fibers and engineering resins accounted for approximately 85% of total adipic acid consumption in 2011. Polyester polyols and plasticizers, which combined accounted for 24-32% of global adipic acid consumption in 2010 . Other 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. Adipic acid has been identified as being used in hydraulic fracturing as a gelling agent. HUMAN EXPOSURE AND TOXICITY: Adipic acid exhibits an asthma hazard index of 0.75 using the chemical asthma hazard assessment program. Substances with indices of >0.5 have a high probability of being an asthmagen. Threshold for irritation of the human eye was 20 mg/cu m. ANIMAL STUDIES: Adipic acid is slightly toxic on acute exposure but produces moderate to severe eye irritation in rabbits (20 mg/24 hr). High concentrations of adipic acid can cause persistent pulmonary structural and functional alterations. In both mice and rabbits, lethal doses produce signs of inactivity, stomach and intestinal distention, and irritation and hemorrhage of the intestines. 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. Adipic acid is not mutagenic in Salmonella typhimurium strains TA98, TA100, TA1535, TA1537, and TA1538 or in Escherichia coli (WP2(uvrA)) with or without rat microsomal activation. ECOTOXICITY STUDIES: Adipic acid is slightly to moderately toxic to fish, daphnia, and algae in acute tests.

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.

Rat: inhalation: no effect level: 126 g/L, 15 x 6 hr (as in source)|LD50 Mouse iv 680 mg/kg /From table/|LD50 Mouse oral 1900 mg/kg /From table/|LD50 Mouse ip 275 mg/kg /From table/|For more Non-Human Toxicity Values (Complete) data for ADIPIC ACID (8 total), please visit the HSDB record page.

/AQUATIC SPECIES/ ... Adipic acid is slightly to moderately toxic to fish, daphnia, and algae in acute tests.

Adipic acid is found in beet juice(1) and tobacco(2). Adipic acid can be formed in the ambient atmosphere via photooxidation of olefins and hydrocarbons(3-5).

Adipic acid's production and use as a feedstock in the manufacture of nylon 6,6 resins and fibers, polyester polyols, plasticizers, and lubricant additives and as a food acidulant(2) may result in its release to the environment through various waste streams(SRC). Its use as an ingredient if hydraulic fracturing fluids(3) will result in its direct release to the environment(SRC). Adipic acid can be released into the environment via burning of biomass(4) and motor exhaust(5). Adipic acid is a chemical constituent of tobacco smoke(6). Adipic acid has been identified as a biodegradation product of di-2-ethylhexyl adipate(7).

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).

The rate constant for the vapor-phase reaction of adipic acid with photochemically-produced hydroxyl radicals has been estimated as 5.6X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.9 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the reaction of hydroxyl radicals in aqueous solutions at pH 2.0-2.2 is 2.0X10+9 L/mol-sec(2); this corresponds to an aquatic half-life of 1.1 years at an aquatic concentration of 1X10-17 hydroxyl radicals per liter(3). Adipic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Results of UV-assisted ozonolysis tests indicate that environmental reaction of ozone is not a significant removal pathway for adipic acid(5).|Aquatic reactions: photo-oxidation by UV in aqueous medium at 90-95 °C; time for the formation of carbon dioxide (% of theoretical): at 25%: 2.0 hr; at 75%: 32.4 hr; and at 50%: 5.0 hr.

An estimated BCF of 3 was calculated in fish for adipic acid(SRC), using a log Kow of 0.08(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of adipic acid can be estimated to be 24(SRC). According to a classification scheme(2), this estimated Koc value suggests that adipic acid is expected to have very high mobility in soil. 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).

The Henry's Law constant for adipic acid is estimated as 1.8X10-12 atm-cu m/mole(SRC) derived from its vapor pressure, 2.27X10-7 mm Hg(1), and water solubility, 2.43X10+4(2). This Henry's Law constant indicates that adipic acid is expected to be essentially nonvolatile from water surfaces(3). In addition, adipic acid has pKa values of 4.44 and 5.44(4) indicating that adipic acid will exist almost entirely in the ionized form under environmental pHs which will attenuate volatilization(SRC). Adipic acid's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Adipic acid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER: Groundwater samples contaminated by industrial pollution near Barcelona, Spain were found to contain adipic acid at concentrations ranging from <5 to 130 ng/L(1).|RAIN/SNOW: Wet precipitation samples (snow, sleet, rain) collected from Tokyo, Japan in 1992 contained adipic acid at concentrations ranging from 0.18 to 7.78 ug/L(1). Adipic acid was detected in rain and snow samples collected in southern California between 1982-84 at concentrations ranging from 0.006 to 0.47 uM(2). Adipic acid was identified in rainwater from Waseca, MN at an unspecified concentration(3). Adipic acid was qualitatively detected in rainwater samples collected from New Brunswick, NJ during 1999-2000 sampling(4).

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).

According to the 2012 TSCA Inventory Update Reporting data, 19 reporting facilities estimate the number of persons reasonably likely to be exposed manufacturing, processing, or use of adipic acid in the United States may be as low as <10 workers and as high as 1000-9999 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 140,635 workers (77,996 of these are female) are potentially exposed to adipic acid in the US(1). Occupational exposure to adipic acid may occur through inhalation of dust particles and dermal contact with this compound at workplaces where adipic acid is produced or used(SRC). Monitoring and use data indicate that the general population may be exposed to adipic acid via inhalation of ambient air, ingestion of foods and dermal contact with consumer products containing adipic acid(SRC).

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.

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.

Inhalation 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)

INHALATION: 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)

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.

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep victim quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed) Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... Monitor for shock and treat if necessary ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective. Do not attempt to neutralize, because of exothermic reaction. cover skin burns with dry, sterile dressing after decontamination ... . /Organic acids and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

/CASE REPORTS/ We present the first case of occupational asthma to colophony-free solder wire containing an adipic acid flux, previously only reported in a pharmaceutical factory worker who was in contact with spiramycin powder. The 43-yr-old female presented with rhinitic symptoms in 1992. She had worked as a solderer and desolderer of alternator parts since June 1989. The process used a colophony-free solder wire containing an adipic acid flux from 1996, but, when desoldering, colophony fluxes may still have been present. From 1998, she experienced a gradual onset of breathlessness and chest tightness, which she noticed was affecting her keep-fit. She had had no asthma, hay fever or eczema in childhood, and there was no family history of these conditions. She was a lifelong nonsmoker and gave negative skin-prick test results to common environmental allergens. She started to show nocturnal waking and shortness of breath in the morning, feeling better on days away from work, particularly on holiday. She also noticed that she felt better when not soldering at work. She carried out serial peak expiratory flow measurements four times daily for a total of 4 weeks. When plotted using the Oasys program, they showed work-related changes, with an Oasys score of 3.1 (probable occupational asthma; a score of >2.50 has a sensitivity of 75% and specificity of 94% for occupational asthma diagnosis) and an area between the curves (ABC) score of 15 L/min x hr (an ABC score of >/= 15 L/min x hr has a sensitivity of 69% and specificity of 100%). She was admitted for specific inhalation challenge testing to colophony- and adipic-acid-fluxed solder wires. She melted /about/ 1 m of solder wire (using an iron heated to 170 °C) over three challenges, totalling 30 min for the colophony-containing wire and 12 min for the adipic acid wire. ... She exhibited a late asthmatic reaction after the adipic acid exposure, with her forced expiratory volume in 1 sec falling by a maximum of 28% from baseline. She showed no reaction to the colophony-fluxed solder wire. Her methacholine reactivity before challenge was 3,450 ug methacholine (normal) using the method of Yan et al., halving following adipic acid wire challenge to 1,729 ug (mildly hyperreactive). Adipic acid exhibits an asthma hazard index of 0.75 using the chemical asthma hazard assessment program. Substances with indices of >0.5 have a high probability of being an asthmagen. Other non-colophony-based fluxes, such as palmitic acid and dodecanedioic acid, also have high hazard indices (0.92 and 0.94, respectively). On follow-up, the worker had joined a different company as a toilet cistern assembler. She still showed significant asthma, with occasional nocturnal wakening and a St George's Respiratory Questionnaire score of 50.8. Her methacholine reactivity was normal at >4,800 ug. Thus adipic-acid-fluxed solder wire is a new cause of occupational asthma.|/CASE REPORTS/ Two cases of bronchial asthma due to spiramycin in workers of a pharmaceutical factory are reported. The subjects complained of cough, breathlessness and symptoms of asthma at work when coming into contact with spiramycin's powder. The symptoms cleared when away from work for more than 3 or 4 days. Inhalation challenge tests by aerosolization of solutions of spiramycin reproduced asthmatic reactions dual in type in both patients, the immediate component of the response has not been previously described for this antibiotic. Furthermore, one of the patients developed an immediate asthmatic reaction also after inhalation of a solution of adipic acid, and additive to bind spiramycin and diminish its irritant action. The reaction was obtained at a non-irritant concentration of the acid, was reproducible and inhibited by previous administration of sodium cromoglycate: this finding and the failure to elicit the reaction in the other patient suggest a hypersensitivity reaction to this substance.|/OTHER TOXICITY INFORMATION/ Threshold for irritation of the human eye was 20 mg/cu m.

adipate

The substance can be absorbed into the body by inhalation of its aerosol.

Cough. Sore throat.

Redness. Pain.

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.

GRADES: Technical; FCC.|Grades of purity: Commercial, 99.8%|Food grades

All other basic organic chemical manufacturing|Hexanedioic acid: ACTIVE|Each year, an estimated 35,000 wells are hydraulically-fractured in the U.S. Although the oil and gas extraction industry as a whole has a relatively higher fatality rate compared to most of the U.S. general industry... there is currently no worker injury/illness or fatality data publicly available for hydraulic fracturing or flowback operations. Regardless of the availability of data, more workers are potentially exposed to the hazards created by hydraulic fracturing and flowback operations due to the large increase in the number of these operations in the past decade. /Hydraulic fracturing/|48th highest-volume chemical produced in USA (1985).|Since about 90% of worldwide adipic acid production is used in nylon-6.6, synthetic fiber producers are the predominant adipic acid manufacturers.|Adiponitrile can be the precursor of hexamethylenediamine and adipic acid by hydrolysis in the manufacture of nylon 6.6.|46th highest-volume chemical produced in the U.S. (1991).

Gas-liquid chromatographic determination of adipic acid in cracking candy and soft drinks (food additive).|Chromatographic determination of the esters has also become the method of choice for determining adipic acid in oxidation mixtures, synthetic fatty acid mixtures, and synthetic polyamides.|Gas-liquid chromatographic determination of adipate content of acetylated di-starch adipate was studied.|The analytical procedures for food-grade adipic acid are described .... Assay is by direct titration. ... Ash is determined gravimetrically as the residue remaining after ashing 100 g of adipic acid at 850 °C in a platinum dish.

EPA Safer Chemical Functional Use Classes -> Processing Aids and Additives|Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern|Food additives|Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]|Cosmetics -> Buffering

Flavouring Agent -> FLAVOURING_AGENT; Food Additives -> ACIDITY_REGULATOR;|Flavoring Agents