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Fumaric acid(CAS No. 110-17-8)

Fumaric acid C4H4O4 (cas 110-17-8) Molecular Structure

110-17-8 Structure

Identification and Related Records

【Name】
Fumaric acid
【CAS Registry number】
110-17-8
【Synonyms】
trans-2-Butenedioic acid
【EINECS(EC#)】
203-743-0
【Molecular Formula】
C4H4O4 (Products with the same molecular formula)
【Molecular Weight】
116.07
【Inchi】
InChI=1/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
【InChIKey】
VZCYOOQTPOCHFL-OWOJBTEDSA-N
【Canonical SMILES】
C(=CC(=O)O)C(=O)O
【Isomers smiles】
C(=C/C(=O)O)\C(=O)O
【MOL File】
110-17-8.mol

Chemical and Physical Properties

【Appearance】
white powder or colourless crystals
【Density】
1.625
【Melting Point】
295-300℃
【Boiling Point】
355.5°Cat760mmHg
【Flash Point】
230℃
【Water】
0.63 g/100 mL (25℃)
【Solubilities】
0.63 g/100 mL (25 oC)
【Color/Form】
Needles, monoclinic prisms or leaflets from water
Colorless crystals
WHITE CRYSTALLINE POWDER
【Stability】
Stable at room temperature. Decomposes at around 230 C. Incompatible with strong oxidizing agents, bases, reducing agents. Combustible.
【Spectral properties】
MAX ABSORPTION (WATER): 208 NM (LOG E= 4.20); SADTLER REFERENCE NUMBER: 472 (IR, PRISM); 127 (IR, GRATING)
IR: 1278 (Coblentz Society Spectral Collection)
UV: 165 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 4407 (Sadtler Research Laboratories Spectral Collection)
Raman: 12 (Sadtler Research Laboratories Spectral Collection)
MASS: 1989 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
【Computed Properties】
Molecular Weight:116.07216 [g/mol]
Molecular Formula:C4H4O4
XLogP3:-0.3
H-Bond Donor:2
H-Bond Acceptor:4
Rotatable Bond Count:2
Exact Mass:116.010959
MonoIsotopic Mass:116.010959
Topological Polar Surface Area:74.6
Heavy Atom Count:8
Formal Charge:0
Complexity:119
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:1
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Anion Count:2
Effective Rotor Count:2
Conformer Sampling RMSD:0.4
CID Conformer Count:5

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36
【Safety Statements 】
S26
【Safety】

Hazard Codes:?IrritantXi
Risk Statements: 36?
R36:Irritating to eyes.
Safety Statements: 26?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 9126
WGK Germany: 1
RTECS: LS9625000
Fumaric acid converts to the irritant maleic anhydride, upon partial combustion.

?

【PackingGroup 】
Z01
【Skin, Eye, and Respiratory Irritations】
It is a mild irritant of skin and mucous membranes ...
Dust: Irritating to eyes, nose and throat. If inhaled will cause coughing or difficult breathing. Solid: Irritating to skin and eyes.
May cause respiratory tract irritation. May cause skin irritation. Causes eye irritation.
【Cleanup Methods】
Environmental considerations - land spill: Dig a pit, lagoon, 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 fiefighting water. Neutralize with agricultural lime (CaO), crushed limestone (CaCO3), or sodium bicarbonate (NaHCO3).
Environmental considerations - water spill: Neutralize with agricultural lime (CaO), crushed limestone (CaCO3), or sodium bicarbonate (NaHCO3). If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Adjust pH to neutral (pH = 7). Use mechanical dredges or lifts to remove immobililzed masses of pollutants and precipitates.
Personal precautions: Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation.
Environmental precautions: Do not let product enter drains.
Methods for cleaning up: Pick up and arrange disposal withour creating dust. Keep in suitable, closed containers for disposal.
【Transport】
UN 9126
【Fire Fighting Procedures】
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 chemicals, or carbon dioxide.
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.
【Fire Potential】
SLIGHT
【Formulations/Preparations】
Grades: Technical; crystal; FCC /Food Chemicals Codex/.
ASTM D3504-76 > 99.5%
Resin grade: 99.6%
FCC /Food Chemicals Codex/; fine granular, fine powders, powder (80 mesh) and technical grades.
【Exposure Standards and Regulations】
Fumaric acid and its calcium, ferrous, magnesium, potassium, and sodium salts may be safely used in food in accordance with the following prescribed conditions: (a) The additives meet the following specifications: (1) Fumaric acid contains a minimum of 99.5 percent by weight of fumaric acid, calculated on the anhydrous basis. (2) The calcium, magnesium, potassium, and sodium salts contain a minimum of 99 percent by weight of the respective salt, calculated on the anhydrous basis. Ferrous fumarate contains a minimum of 31.3 percent total iron and not more than 2 percent ferric iron. (b) With the exception of ferrous fumarate, fumaric acid and the named salts are used singly or in combination in food at a level not in excess of the amount reasonably required to accomplish the intended effect. (c) Ferrous fumarate is used as a source of iron in foods for special dietary use, when the use is consistent with good nutrition practice.
Fumaric acid is an indirect food additive for use only as a component of adhesives.
【Reactivities and Incompatibilities】
Fumaric acid undergoes reactions typical of an organic acid.
Materials to avoid: Oxidizing agents, amines, strong bases.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.
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.
Handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.
In case of skin contact: Wash off with soap and plenty of water. Consult a physician.
In case of eye contact: Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Hygiene measures: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
【Protective Equipment and Clothing】
Wear appropriate chemical protective gloves, boots, and goggles.
Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Hand protection: The selected protective gloves have to satisfy the specifications of EU Directive 89/689/EEC and the standard EN 374 derived from it. Handle with gloves.
Eye protection: Safety glasses.
Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place.
【Specification】

?Fumaric acid ,?its cas register number is?110-17-8. It also can be called?1,2-Ethenedicarboxylic acid, trans- ; 1,2-Ethylenedicarboxylic acid, (E) ; 2-Butenedioic acid, (E)- ; Allomaleic acid ; Allomalenic acid ; Butenedioic acid, (E)- ; Kyselina fumarova ; Lichenic acid ; Tumaric acid ; trans-1,2-Ethylenedicarboxylic acid ;
?trans-Butenedioic acid .

【Octanol/Water Partition Coefficient】
log Kow = 0.46
【Disposal Methods】
SRP: 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.
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Commercially, fumaric acid may be prepared from glucose by the action of fungi such as Rhizopus nigricans, as a by-product in the manufacture of maleic and phthalic anhydrides, and by the isomerization of maleic acid using heat or a catalyst. On the laboratory scale, fumaric acid can be prepared by the oxidation of furfural with sodium chlorate in the presence of vanadium pentoxide.
Maleic acid or maleic anhydride, especially the maleic acid-containing wash water from the production of maleic anhydride or phthalic anhydride, serves as starting material for the manufacture of fumaric acid. The maleic acid concentration should be at least 30%. Maleic acid is converted almost quantitatively by thermal or catalytic isomerization into the sparingly soluble fumaric acid, which is recovered by filtration. Various substances have been proposed as catalysts: mineral acids (e.g., hydrochloric acid); sulfur compounds such as thiocyanates, thiazoles, thiosemicarbazides, thioureas; or bromine compounds in combination with peroxides (e.g., persulfate). Thiourea is most commonly used in practice. The maleic acid-containing wash water contains impurities that can affect quality and yield. This problem can be largely avoided (1) by thermal pretreatment of the wash water, (2) by adding urea if thiourea is used as catalyst, and (3) by addition of sulfites or passaged of sulfur dioxide and addition of mineral acids. The crude fumaric acid obtained is purified by recrystallization from water, combined with purification by active charcoal. Losses during purification are about 10%.
U.S. Exports

(1984) Negligible
CHEMICAL PROFILE: Fumaric acid. US Imports: 1991: 2.9 million pounds.
CHEMICAL PROFILE: Fumaric acid. US Imports: 1993: 3.3 million pounds.
CHEMICAL PROFILE: Fumaric acid. US Imports: 1998: 2.7 million pounds; 1999: 1.9 million pounds.
U.S. Imports

(1971) 1.1 X 10+8 g (Princpl Custms Dists)
(1975) 3.98 X 10+8 g (Princpl Custms Dists)
(1984) 3.04 X 10+8 g
CHEMICAL PROFILE: Fumaric acid. US Imports: 1988: 4 million pounds.
CHEMICAL PROFILE: Fumaric acid. US Imports: 1991: 8.9 million pounds.
CHEMICAL PROFILE: Fumaric acid. US Imports: 1993: 14.2 million pounds.
CHEMICAL PROFILE: Fumaric acid. US Imports: 1998: 30 million pounds; 1999: 34.3 million pounds.
U.S. Production

(1972) 2.34 X 10+10 g
(1975) 9.46 X 10+9 g
(1984) 2.24 X 10+10 g
2-Butenedioic acid (2E)- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >50 million - 100 million 1990 >10 million - 50 million 1994 >1 million - 10 million 1998 >10 million - 50 million 2002 >10 million - 50 million
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2-Butenedioic acid (2E)-. Aggreated National Production Volume: 1 to
CHEMICAL PROFILE: Fumaric acid. US Production Capacity: 1989: 39 million pounds.
CHEMICAL PROFILE: Fumaric acid. US Production Capacity: 1991: 39 million pounds.
CHEMICAL PROFILE: Fumaric acid. US Production Capacity: 1994: 45 million pounds.
CHEMICAL PROFILE: Fumaric acid. US Production Capacity: 1999: 50 million pounds.
Consumption Patterns

31% as a fortifier in paper size resins; 26% as a fortifier in unsaturated polyester resins; 12% as a fortifier in alkyd surface coating resins; 12% as a food acidulant in gelatin desserts and dry beverage powders; 7% as a chemical intermediate for plasticizers including dibutyl fumarate; 12% in miscellaneous applications (1974)
50% is used to produce paper size resins; 20% for food acidulant; 10% for unsaturated polyester resins; 5% for alkyds; 5% for plasticizers; and 10% for miscellaneous (1983)
CHEMICAL PROFILE: Fumaric acid. US End-use Pattern for Fumaric Acid in 1985. US End-use pattern for fumaric acid in 1985 End-use Percent Paper size resins 48 Food acidulant 20 Unsaturated polyester resins 16 Alkyds 5 Exports 5 Miscellaneous 6
CHEMICAL PROFILE: Fumaric Acid. US End-use Pattern for Fumaric Acid in 1988. US End-use pattern for fumaric acid in 1988 End-use Percent Paper size resins 45 Food acidulant 20 Unsaturated polyester resins 15 Alkyds 5 Exports 9 Miscellaneous 6
CHEMICAL PROFILE: Fumaric Acid. US End-use Pattern for Fumaric Acid in 1991. US End-use pattern for fumaric acid in 1991 End-use Percent Paper size resins 39 Food acidulants 20 Unsaturated polyester resins 13 Alkyd resins 5 Other, including lubricating oils and oil field fluids, organic synthesis of esters, inks, lacquers, carboxylating agent 23
CHEMICAL PROFILE: Fumaric Acid. US End-use Pattern for Fumaric Acid in 1994. US End-use pattern for fumaric acid in 1994 End-use Percent Paper size resins 40 Food acidulant 20 Unsaturated polyester resins 15 Alkyd resins 5 Miscellaneous, including lubricating oils and oil field fluids, esters, inks, lacquers, carboxylating agent for styrene-butadiene rubber 20
CHEMICAL PROFILE: Fumaric Acid. US End-use Pattern for Fumaric Acid in 1999. US End-use pattern for fumaric acid in 1999 End-use Percent Paper size resins 35 Food acidulant 22 Unsaturated polyester resins 15 Alkyd resins 6 Plasticizers 5 Miscellaneous, including lubricating oils and oil field fluids, esters, inks, lacquers, and as a carboxylating agent for styrene-butadiene rubber 17
CHEMICAL PROFILE: Fumaric acid. US Demand: 1985: 30 million pounds; 1986: 30 million pounds; 1990: 33.2 million pounds /projected/.
CHEMICAL PROFILE: Fumaric acid. US Demand: 1988: 31 million pounds; 1989: 32 million pounds; 1993: 36 million pounds /projected/.
CHEMICAL PROFILE: Fumaric acid. US Demand: 1991: 28 million pounds; 1992: 28 million pounds; 1996: 29 million pounds /projected/.
CHEMICAL PROFILE: Fumaric acid. US Demand: 1994: 38 million pounds; 1995: 38.4 million pounds; 1999: 40 million pounds /projected/.
CHEMICAL PROFILE: Fumaric acid. US Demand: 1998: 40 million pounds; 1999: 40.7 million pounds; 2003: 43.4 million pounds /projected/.
【Usage】
Occurs in many plants. Essential to vegetable and tissue respiration. Used as an antioxidant.

Biomedical Effects and Toxicity

【Pharmacological Action】
Inhalation of dust may cause respiratory irritation. Compound is non-toxic when ingested. Prolonged contact with eyes or skin may cause irritation.
【Therapeutic Uses】
Fumaric acid is used in oral pharmaceutical formulations and food products, and is generally regarded as a relatively nontoxic and nonirritant material.
Fumaric acid preparations are used as long term and effective treatment of psoriasis. /Fumaric acid preparation/ [Raschka C, Koch Hj; Hum Exp Toxicol 18 (12): 738-9 (1999). Available from, as of January 7, 2009:]
【Biomedical Effects and Toxicity】
The total activity of labeled carbon dioxide in the blood entering and leaving the brain was determined following a single injection of fumarate-2-(14)C in four normal human subjects. Blood samples were drawn simultaneously from the femoral artery and the superior bulb of the internal jugular vein. Also, cerebrospinal fluid specimens were collected. Evidence from the experiments indicates that there was an immmediate formation of (14)CO2 by the brain after injection of the isotope. It suggests that fumarate penetrates the blood-brain barrier with little difficulty.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7(SRC), determined from a structure estimation method(2), indicates that fumaric acid is expected to have very high mobility in soil(SRC). The pKa values of fumaric acid are 3.03 and 4.54(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of fumaric acid from moist soil surfaces is not expected to be an important fate process(SRC) given its pKa(3). Fumaric acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.54X10-4 mm Hg(5). Using a Warburg respirometer and a sewage inoculum, 5 day Theoretical BODs of 57-70% were reported(6), suggesting that biodegradation may be an important environmental fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7(SRC), determined from a structure estimation method(2), indicates that fumaric acid is not expected to adsorb to suspended solids and sediment(SRC). A pKa values of 3.03 and 4.54(3) indicate fumaric acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of 0.46(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Fumaric acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(8). The rate constant for the aqueous reaction of fumaric acid with photochemically produced hydroxyl radicals (pH 4.5-10) is 6.0X10+9/M-sec(9); using a hydroxyl radical concentration of 3X10-17 M in brightly sunlit natural water(10), the half-life would be 45 days(SRC). The half-life of fumaric acid in various natural waters ranged from 1-15 days using river die-away studies, indicating that biodegradation is an important environmental fate process in water(11).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fumaric acid, which has a vapor pressure of 1.54X10-4 mm Hg at 25 deg C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase fumaric acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC); the half-lives for these reactions in air are estimated to be 7 hours and 6 days(SRC), calculated from rate constants of 5.3X10-11 cu cm/molecule-sec(3) and 1.8X10-18 cu cm/molecule-sec(4), respectively. Particulate-phase fumaric acid may be removed from the air by wet or dry deposition(SRC). Fumaric acid does not absorb UV light above 290 nm in methanol, acidic methanol, or basic methanol solution(5) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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