Fumaric acid

From Sciencemadness Wiki
Revision as of 16:37, 31 December 2021 by Mabus (Talk | contribs) (Created page with "{{Chembox | Name = Fumaric acid | Reference = | IUPACName = (2E)-But-2-enedioic acid | PIN = | SystematicName = | OtherNames = 2-Butenedioic acid<br>Allomaleic acid<br>Boletic...")

(diff) ← Older revision | Latest revision (diff) | Newer revision → (diff)
Jump to: navigation, search
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
168 J·mol−1·K−1
-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):
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.

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

  1. Справочник химика. - Т. 2. - Л.-М.: Химия, 1964 (Chemist's Handbook. - T. 2.- L.-M .: Chemistry, 1964)
  2. Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941
  3. Journal of Chemical and Engineering Data. - 2009. - Vol. 54, No. 11 pp. 3112
  4. Journal of Chemical and Engineering Data. - 2009. - Vol. 54, No. 11 pp. 3112
  5. http://www.orgsyn.org/demo.aspx?prep=CV2P0302
  6. http://www.orgsyn.org/content/pdfs/procedures/cv2p0302.pdf
  7. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/jlac.18922680108
  8. https://onlinelibrary.wiley.com/doi/10.1002/14356007.a16_053

Relevant Sciencemadness threads