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Dibutyl maleate

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Name Dibutyl maleate EINECS 203-328-4
CAS No. 105-76-0 Density 1.004 g/cm3
Solubility Insoluble in water Melting Point -85 °C
Formula C12H20O4 Boiling Point 280 °C at 760 mmHg
Molecular Weight 228.29 Flash Point 136.4 °C
Transport Information Appearance clear colourless to slightly yellowish liquid
Safety 26-36-61-37-29-24 Risk Codes 36/37/38-51/53-43
Molecular Structure Molecular Structure of 105-76-0 (Dibutyl maleate) Hazard Symbols IrritantXi,DangerousN
Synonyms

Dibutyl maleate;DBM

 

Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The CAS registry number of Dibutyl maleate is 105-76-0. Its EINECS registry number is 203-328-4. The systematic name is dibutyl but-2-enedioate. In addition, the molecular formula is C12H20O4 and the molecular weight is 228.28. What's more, it is a kind of clear colourless to slightly yellowish liquid and belongs to the classes of Plasticizer; Carbonyl Compounds; Esters. It can be used as raw material for synthetic resin, and used as organic synthesis intermediates.

Physical properties about this chemical are: (1)ACD/LogP: 3.81; (2)ACD/LogD (pH 5.5): 3.81; (3)ACD/LogD (pH 7.4): 3.81; (4)ACD/BCF (pH 5.5): 461.68; (5)ACD/BCF (pH 7.4): 461.68; (6)ACD/KOC (pH 5.5): 2810.22; (7)ACD/KOC (pH 7.4): 2810.22; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 10; (10)Polar Surface Area: 52.6 Å2; (11)Index of Refraction: 1.451; (12)Molar Refractivity: 61.25 cm3; (13)Molar Volume: 227.1 cm3; (14)Polarizability: 24.28 ×10-24cm3; (15)Surface Tension: 33.4 dyne/cm; (16)Density: 1.004 g/cm3; (17)Flash Point: 136.4 °C; (18)Enthalpy of Vaporization: 51.87 kJ/mol; (19)Boiling Point: 280 °C at 760 mmHg; (20)Vapour Pressure: 0.00388 mmHg at 25°C.

Preparation of Dibutyl maleate: it can be prepared by cisbutenedioic anhydride and butanol in the presence of sulfuric acid through esterification reaction. After a series of neutralization, washing, dehydroxylation, distillation and filtration you can get the desired product from the reaction product.

Uses of Dibutyl maleate: it is used as impregnants, dispersants, lubricants and plasticizers. And it can react with 1H-imidazole to get 2-imidazol-1-yl-succinic acid dibutyl ester. The reaction time is 7 hours at reaction temperature of 100 °C. The yield is about 50%.

Dibutyl maleate can react with 1H-imidazole to get 2-imidazol-1-yl-succinic acid dibutyl ester

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. It may cause sensitization by skin contact. In addition, it is very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing and gloves and avoid contact with skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Moreover, you should avoid release to the environment and you can refer to special instructions safety data sheet. You can not empty it into drains.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCCCC)C=CC(=O)OCCCC
(2)InChI: InChI=1/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
(3)InChIKey: JBSLOWBPDRZSMB-UHFFFAOYAY

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 150mg/kg (150mg/kg)   National Technical Information Service. Vol. AD691-490,
rabbit LD50 skin 10gm/kg (10000mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 2, Pg. 19, 1975.
rat LD50 oral 3700mg/kg (3700mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 2, Pg. 19, 1975.

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