Dibutyl maleate

Dibutyl maleate is an organic compound with the formula (CHCO2Bu)2 (Bu = butyl). It is the diester of the unsaturated dicarboxylic acid maleic acid. It is a colorless oily liquid, although impure samples can appear yellow.

Maleic acid dibutyl ester
Chemical structure of maleic acid dibutyl ester
Names
Preferred IUPAC name
Dibutyl (2Z)-but-2-enedioate
Other names
  • Maleic acid dibutyl ester
  • DBM
Identifiers
3D model (JSmol)
3DMet
ChEMBL
ChemSpider
ECHA InfoCard 100.003.027
EC Number
  • 203-328-4
MeSH maleate dibutyl maleate
UNII
  • InChI=1S/C12H20O4/c1-3-5-9-15-11(13)7-8-12(14)16-10-6-4-2/h7-8H,3-6,9-10H2,1-2H3/b8-7-
    Key: JBSLOWBPDRZSMB-FPLPWBNLSA-N
  • CCCCOC(=O)/C=C\C(=O)OCCCC
Properties
C12H20O4
Molar mass 228.288 g·mol−1
Appearance Colorless to yellowish liquid with a characteristic odor[1]
Density 0.99 g·cm−3[1]
Melting point −85 °C (−121 °F; 188 K)[1]
Boiling point 280 °C (536 °F; 553 K)[1]
Very hardly soluble (0.17 g·l−1 at 20 °C)[1]
Vapor pressure 0.0027 hPa (20 °C)[1]
1.445 (20 °C)[2]
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard[1]
H317, H373, H411[1]
P273, P280, P302+P352, P314[1]
Flash point 141 °C (286 °F; 414 K)[1]
265 °C (509 °F; 538 K)[1]
Explosive limits
  • Lower limit: 0.5 vol-%[1]
  • Upper limit: 3.4 vol-%[1]
Lethal dose or concentration (LD, LC):
  • 3700 mg·kg−1 (rat, oral)[1]
  • 10000 mg·kg−1 (rabbit, dermal)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation

Dibutyl maleate can be prepared by the reaction of maleic acid anhydride and 1-butanol in presence of p-toluenesulfonic acid.[3][4]

Uses

Dibutyl maleate is mainly used as a plasticizer for aqueous dispersions of copolymers with vinyl acetate and as an intermediate in the preparation of other chemical compounds.[5] With the invention of polyaspartic technology the material found another use. In this situation, an amine is reacted with a dialkyl maleate - usually diethyl maleate but also dibutyl maleate may be used- utilizing the Michael addition reaction. The resulting products, polyaspartic esters products are then used in coatings, adhesives, sealants and elastomers.[6]

See also

References
  1. Record of Maleinsäuredibutylester in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 3 April 2019.
  2. Sigma-Aldrich Co., Dibutyl maleate, 96%. Retrieved on 2019-04-03.
  3. R. Wen, L. Long, L. Ding, Silas Yu (2001). "Study on synthesis of dibutyl maleate". Jishou Daxue Xuebao/Journal of Jishou University. 22 (1): 78–80.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. B. Trivedi (2013). Maleic Anhydride. Springer Science & Business Media. p. 277. ISBN 978-1-4757-0940-7.
  5. Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Dibutyl maletate (PDF) (Report). OECD. Retrieved 3 April 2019.
  6. Howarth, GA (2003-06-01). "Polyurethanes, polyurethane dispersions and polyureas: Past, present and future". Surface Coatings International Part B: Coatings Transactions. 86 (2): 111–118. doi:10.1007/BF02699621. ISSN 1476-4865. S2CID 93574741.
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