Maleic acid dibutyl ester

Maleic acid dibutyl ester
Names
	IUPAC name Dibutyl (2Z)-2-butenedioate
	Systematic IUPAC name not
	Other names Dibutyl maleate; DBM;
Identifiers
CAS Number	105-76-0;
3D model (JSmol)	Interactive image;
3DMet	CCCCOC(=O)/C=C\C(=O)OCCCC;
ChEMBL	ChEMBL1466826;
ChemSpider	4436356 ;
EC Number	203-328-4;
MeSH	maleate dibutyl maleate
PubChem CID	5271569;
UNII	4X371TMK9K;
	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−1
Appearance	Colorless to yellowish liquid with a characteristic odor
Density	0.99 g·cm−3
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−1 at 20 °C)
Vapor pressure	0.0027 hPa (20 °C)
Refractive index (nD)	1.445 (20 °C)
Hazards
GHS pictograms
GHS hazard statements	H317, H373, H411
GHS precautionary statements	P273, P280, P302+352, 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−1 (rat, oral); 10000 mg·kg−1 (rabbit, dermal);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Maleic acid dibutyl ester is a chemical compound in the group of carboxylic acid esters.

Preparation

Maleic acid dibutyl ester can be prepared by the reaction of maleic acid anhydride and 1-butanol in presence of p-toluenesulfonic acid.^[3]^[4]

Properties

Maleic acid dibutyl ester is a flammable, hard to ignite, oily, colorless to yellowish liquid with a characteristic odor, which has very low solubility in water.

Uses

Maleic acid dibutyl ester 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]

References

↑ ^1.00 ^1.01 ^1.02 ^1.03 ^1.04 ^1.05 ^1.06 ^1.07 ^1.08 ^1.09 ^1.10 ^1.11 ^1.12 ^1.13 ^1.14 Record of Maleinsäuredibutylester in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 3 April 2019.
↑ Sigma-Aldrich Co., Dibutyl maleate, 96%. Retrieved on 2019-04-03.
↑ 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.
↑ B. Trivedi (2013). Maleic Anhydride. Springer Science & Business Media. pp. 277. ISBN 978-1-4757-0940-7. https://books.google.com/books?id=c8XeBwAAQBAJ&pg=PA277.
↑ (pdf) Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Dibutyl maletate (Report). OECD. http://www.inchem.org/documents/sids/sids/105760.pdf. Retrieved 3 April 2019.

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[GESTIS-1] 1.00 ^1.01 ^1.02 ^1.03 ^1.04 ^1.05 ^1.06 ^1.07 ^1.08 ^1.09 ^1.10 ^1.11 ^1.12 ^1.13 ^1.14 Record of Maleinsäuredibutylester in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 3 April 2019.

[Sigma-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.

[B._Trivedi-4] B. Trivedi (2013). Maleic Anhydride. Springer Science & Business Media. pp. 277. ISBN 978-1-4757-0940-7. https://books.google.com/books?id=c8XeBwAAQBAJ&pg=PA277.

[INCHEM-5] (pdf) Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Dibutyl maletate (Report). OECD. http://www.inchem.org/documents/sids/sids/105760.pdf. Retrieved 3 April 2019.

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Maleic acid dibutyl ester

Topic: Chemistry

Contents

Preparation

Properties

Uses

References

Names

IUPAC name Dibutyl (2Z)-2-butenedioate
Systematic IUPAC name not
Other names Dibutyl maleate DBM
Identifiers
CAS Number	105-76-0
3D model (JSmol)	Interactive image
3DMet	CCCCOC(=O)/C=C\C(=O)OCCCC
ChEMBL	ChEMBL1466826
ChemSpider	4436356^Y
EC Number	203-328-4
MeSH	maleate dibutyl maleate
PubChem CID	5271569
UNII	4X371TMK9K
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⁻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]
Solubility in water	Very hardly soluble (0.17 g·l⁻¹ at 20 °C)^[1]
Vapor pressure	0.0027 hPa (20 °C)^[1]
Refractive index (n_D)	1.445 (20 °C)^[2]
Hazards
GHS pictograms	^[1]
GHS hazard statements	H317, H373, H411^[1]
GHS precautionary statements	P273, P280, P302+352, P314^[1]
Flash point	141 °C (286 °F; 414 K)^[1]
Autoignition temperature	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):
LD₅₀ (median dose)	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