Fumaric acid
| Names | |
|---|---|
| IUPAC name
(2E)-But-2-enedioic acid
| |
| Other names
2-Butenedioic acid
Allomaleic acid Boletic acid Donitic acid E297 Lichenic acid trans-1,2-Ethylenedicarboxylic acid trans-Butenedioic acid | |
| Properties | |
| C4H4O4 (COOH)CH=CH(COOH) | |
| Molar mass | 116.072 g/mol |
| Odor | Odorless |
| Density | 1.635 g/cm3 (20 °C) |
| Melting point | 287 °C (549 °F; 560 K) (decomposition) |
| Boiling point | Decomposes |
| 0.49 g/100 ml (20 °C) 0.70 g/100 ml (25 °C) 1.07 g/100 ml (40 °C) 2.40 g/100 ml (60 °C) 9.80 g/100 ml (100 °C)[1] | |
| Solubility | Soluble in alcohols |
| Solubility in acetone | 1.29 g/100 ml (20 °C) 1.72 g/100 ml (29.7 °C)[2] |
| Solubility in benzene | 0.003 g/100 ml (25 °C) |
| Solubility in carbon tetrachloride | 0.027 g/100 ml (25 °C) |
| Solubility in chloroform | 0.02 g/100 ml (25 °C) |
| Solubility in diethyl ether | 1.01 g/100 ml (25 °C) |
| Vapor pressure | 1.54·10-4 mmHg at 25 °C |
| Acidity (pKa) | cis: pKa1= 3.03 pKa2= 4.44 |
| Thermochemistry | |
| Std molar
entropy (S |
168 J·mol−1·K−1 |
| Std enthalpy of
formation (ΔfH |
-811.7 kJ/mol |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 273 °C (523.4 °F; 546 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
9,300 mg/kg (rat, oral) |
| Related compounds | |
| Related compounds
|
Succinic acid Maleic acid |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Fumaric acid is an organic compound with the formula (COOH)CH=CH(COOH). A white solid, fumaric acid occurs widely in nature. It has a fruit-like taste and has been used as a food additive. Its E number is E297.
Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.
Contents
Properties
Chemical
Fumaric acid reacts with bases to form salts. The salts and esters are known as fumarates.
Physical
Fumaric acid is a colorless solid, poorly soluble in water.
Availability
Fumaric acid can be bought online from food suppliers as food additive.
Can also be bought from chemical suppliers, either as individual isomers, as well as mixture.
Preparation
A traditional synthesis involves oxidation of furfural (from the processing of maize) using sodium chlorate in the presence of a vanadium pentoxide-based catalyst.[5][6]
Fumaric acid can be prepared from succinic acid.[7]
The industrial synthesis of fumaric acid is mostly based on catalytic isomerisation of maleic acid in aqueous solutions at low pH. Maleic acid is accessible in large volumes as a hydrolysis product of maleic anhydride, produced by catalytic oxidation of benzene or butane.[8]
Projects
- Make fumarate salts and esters
- Food additive
- Make anti-psoriasis medication
Handling
Safety
Fumaric acid is irritant in its pure form and should be handled with care.
It is "practically non-toxic" but high doses are considered to be probably nephrotoxic after long-term use.
Storage
In closed bottles or plastic bags, away from acids.
Disposal
No special disposal is required. Can be neutralized with a base, diluted and poured down the drain.
References
- ↑ Справочник химика. - Т. 2. - Л.-М.: Химия, 1964 (Chemist's Handbook. - T. 2.- L.-M .: Chemistry, 1964)
- ↑ Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941
- ↑ Journal of Chemical and Engineering Data. - 2009. - Vol. 54, No. 11 pp. 3112
- ↑ Journal of Chemical and Engineering Data. - 2009. - Vol. 54, No. 11 pp. 3112
- ↑ http://www.orgsyn.org/demo.aspx?prep=CV2P0302
- ↑ http://www.orgsyn.org/content/pdfs/procedures/cv2p0302.pdf
- ↑ https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/jlac.18922680108
- ↑ https://onlinelibrary.wiley.com/doi/10.1002/14356007.a16_053
