Names | |
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Preferred IUPAC name
Dibutyl (2Z)-but-2-enedioate | |
Other names
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Identifiers | |
3D model (
JSmol)
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3DMet | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.027 |
EC Number |
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MeSH | maleate dibutyl maleate |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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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] |
Refractive index (nD)
|
1.445 (20 °C) [2] |
Hazards | |
GHS labelling: | |
[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 | |
Lethal dose or concentration (LD, LC): | |
LD50 (
median dose)
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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.
Dibutyl maleate can be prepared by the reaction of maleic acid anhydride and 1-butanol in presence of p-toluenesulfonic acid. [3] [4]
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]
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