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Dibutyl maleate

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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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.027 Edit this at Wikidata
EC Number
  • 203-328-4
MeSH maleate dibutyl maleate
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • CCCCOC(=O)/C=C\C(=O)OCCCC
Properties
Chemical formula C12H20O4
Molar mass 228.288 g·mol
Appearance Colorless to yellowish liquid with a characteristic odor
Density 0.99 g·cm
Melting point −85 °C (−121 °F; 188 K)
Boiling point 280 °C (536 °F; 553 K)
Solubility in water Very hardly soluble (0.17 g·l at 20 °C)
Vapor pressure 0.0027 hPa (20 °C)
Refractive index (nD) 1.445 (20 °C)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Hazard statements H317, H373, H411
Precautionary statements P273, P280, P302+P352, P314
Flash point 141 °C (286 °F; 414 K)
Autoignition
temperature 		265 °C (509 °F; 538 K)
Explosive limits
  • Lower limit: 0.5 vol-%
  • Upper limit: 3.4 vol-%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 3700 mg·kg (rat, oral)
  • 10000 mg·kg (rabbit, dermal)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

Preparation

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

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. 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.

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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