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 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 (nD)

| 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

Tracking categories (test):

* SizeSet

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

## Contents

* 1 Preparation
* 2 Properties
* 3 Uses
* 4 References

## 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. ↑ 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.
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.
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.
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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*[CID]: Compound ID
*[H317]: May cause an allergic skin reaction
*[H373]: May cause damage to organs through prolonged or repeated exposure
*[H411]: Toxic to aquatic life with long lasting effects
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P314]: Get Medical advice/attention if you feel unwell