Diethyl maleate Property

Melting point:

-10 °C (lit.)

Boiling point:

225 °C (lit.)

Density 

1.064 g/mL at 25 °C (lit.)

vapor density 

5.93 (vs air)

vapor pressure 

1 mm Hg ( 14 °C)

refractive index 

n20/D 1.441(lit.)

Flash point:

200 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

14mg/l

form 

Liquid

color 

Clear

Odor

at 100.00 %. fruity banana citrus

Odor Type

fruity

Water Solubility 

insoluble

Merck 

14,3123

BRN 

1100825

Dielectric constant

8.6（23℃）

Stability:

Stable. Combustible. Incompatible with oxidizing agents, bases, acids, reducing agents.

InChIKey

IEPRKVQEAMIZSS-AATRIKPKSA-N

LogP

2.2

CAS DataBase Reference

141-05-9(CAS DataBase Reference)

NIST Chemistry Reference

2-Butenedioic acid (Z)-, diethyl ester(141-05-9)

EPA Substance Registry System

2-Butenedioic acid (2Z)-, 1,4-diethyl ester (141-05-9)

Safety

Hazard Codes 

Xi

Risk Statements 

36-43-52/53

Safety Statements 

26-36/37-37-24-24/25

RIDADR 

3334

WGK Germany 

2

RTECS 

ON1225000

Autoignition Temperature

662 °F

TSCA 

Yes

HS Code 

29171990

Toxicity

LD50 orally in rats: 0.30 g/kg (Smyth)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Diethyl maleate Chemical Properties,Usage,Production

Chemical Properties

Diethyl maleate is a colorless clear liquid between the temperatures of -10°C (pour point) and 225°C (boiling point). Insoluble in water, soluble in ethanol and ether. its odor type is fruity and its odor at 100% is described as "fruity bananacitrus". It is prohibited by lFRA and theEU because of sensitization and is notused anymore as fragrance.

Occurrence

Has apparently not been reported to occur in nature.

Uses

Diethyl maleate can be used for the preparation of organophosphorus insecticide malathion. It is unsaturated polyester resins that are used in applications, such as reinforced glass fiber for boats, piping, bathtubs, roof panels, etc., and as protective coatings, finishes, and lacquers.

Uses

Diethyl Maleate is used as a reagent in the synthesis of several organic compounds including that of polyaspartic acid ester based polyurea coatings. It was found to inhibit MCA and TPA transformed cell growth via modulation of glutathione, mitogen-activated protein kinase and cancer pathways.

Definition

ChEBI: Diethyl maleate is a maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10℃) with boiling point 220℃ at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis. It has a role as a glutathione depleting agent. It is a maleate ester and an ethyl ester. It derives from an ethanol.

Preparation

Diethyl maleate is synthesized by the direct esterification of maleic anhydride and ethanol in the presence of sulfuric acid. Esterification is a commonly used reaction in organic synthesis.

General Description

Diethyl maleate is reported to occur in the cabernet sauvignon wine.

Synthesis

5g maleic anhydride, 12g dehydrated alcohol, 0.3g acid zeolite, 15ml benzene are added to the reaction vessel, install water trap, reflux condensing tube, and thermometer on the reaction vessel, reflux water-dividing is carried out in heating, reaction reacts 30min again after occurring without the globule, stops heating, after normal temperature cooling 30min, release water layer, reaction solution washes with water, distill after drying, first steam front-end volatiles, the cut regathering 216 ~ 220 DEG C is product Diethyl maleate.

Metabolism

α/β-Unsaturated compounds, such as diethyl maleate, react enzymically with gluta thione. The reaction has been demonstrated in fractions of rat liver (Boyland & Chasseaud, 1967) and avian liver (Wit & Snel, 1968). The enzyme differs from other known S-alkyl, S-aryl and S- epoxide transferase enzymes responsible for glutathione-conjugate formation (Boyland & Chasseaud, 1967). Diethyl maleate, administered parenterally to rats, reduced the hepatic glutathione content (Boyland & Chasseaud, 1970; Varga, Fischer & Szily, 1974). The latter workers also showed that diethyl maleate pretreatment of rats inhibited the glutathione conjugation of subsequently-adminis tered bromsulphthalein.