142-16-5

Basic information

• Product Name: Bis(2-ethylhexyl) maleate
• Synonyms: Bis(2-ethylhexyl) (2Z)-2-butenedioate;bis(2-ethylhexyl)-2butenedioate;bis(2-ethylhexyl)-2-butenedioate;Bis-(2-ethylhexyl)ester kyseliny maleinove;bis-(2-ethylhexyl)esterkyselinymaleinove;di(2-ethvlhexvl)maleate;Rc comonomer dom;rccomonomerdom
• CAS NO: 142-16-5
• Molecular Formula: C₂₀H₃₆O₄
• Molecular Weight: 340.5
• EINECS: 220-835-6
• Product Categories: Fatty Acid Esters (Plasticizer);Functional Materials;Plasticizer;Plasticizers;Polymer Additives;Polymer Science
• Mol File: 142-16-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: -50°C
• Boiling Point: 208-209°C 10mm
• Flash Point: >230 °F
• Appearance: /Liquid
• Density: 0.944 g/mL at 25 °C(lit.)
• Vapor Pressure: 0Pa at 20℃
• Refractive Index: n20/D 1.455(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Ethyl Acetate(Slightly),Methanol (Slightly)
• Water Solubility: 18μg/L at 20℃
• CAS DataBase Reference: Bis(2-ethylhexyl) maleate(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(2-ethylhexyl) maleate(142-16-5)
• EPA Substance Registry System: Bis(2-ethylhexyl) maleate(142-16-5)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 36/38-51/53-48/22
• Safety Statements: 26-36-61
• WGK Germany: 1
• RTECS: ON0160000
• Hazardous Substances Data: 142-16-5(Hazardous Substances Data)

Usage

Chemical Properties

It is a liquid between -60 and 164°C(boiling point at 10 mmHg).

Uses

Different sources of media describe the Uses of 142-16-5 differently. You can refer to the following data:
1. Bis(2-ethylhexyl) maleate is a derivative of malic acid, with emollient and skin-conditioning properties. It can also be used as a solvent in cosmetic preparations. It is synthetically manufactured.
2. These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

General Description

Bis(2-ethylhexyl) maleate is an aliphatic ester which is prepared by catalytic esterification of maleic acid and 2-ethylhexyl alcohol. It is used as a green plasticizer in variety of applications such as adhesives and coatings.

InChI:InChI=1/C20H36O4/c1-5-9-11-15(7-3)13-17(19(21)22)18(20(23)24)14-16(8-4)12-10-6-2/h15-16H,5-14H2,1-4H3,(H,21,22)(H,23,24)/p-2

Synthetic route

maleic anhydride (108-31-6) + 2-Ethylhexyl alcohol (104-76-7) → bis(2-ethylhexyl) maleate (142-16-5)

Conditions	Yield
With 3,3′-(2,2-bis(hydroxymethyl)propane-1,3-diyl)bis(1-methyl-1H-imidazol-3-ium) hydrogen sulfate for 2h; Dean-Stark; Reflux;	100%
Bei an einer mit einem Trockenmittel gefuellten Kolonne;

maleic anhydride (108-31-6) + rac-3-octanol (589-98-0) → bis(2-ethylhexyl) maleate (142-16-5)

Conditions	Yield
With sulfuric acid; 2,6-di-tert-butyl-4-hydroxytoluene In benzene at 90℃; for 2.5h; Heating / reflux;	90%

2-Ethylhexyl alcohol (104-76-7) + maleic acid (110-16-7) → bis(2-ethylhexyl) maleate (142-16-5)

"1,4-bis(2-ethylhexyl) but-2-ynedioate → bis(2-ethylhexyl) maleate (142-16-5) + bis(2-ethylhexyl) (2E)-2-butenedioate (141-02-6)

Conditions	Yield
With TPPMS (meta-monosulfonated triphenylphosphane, Na salt); water for 24h;

tetrahydrofuran (109-99-9) + bis(2-ethylhexyl) maleate (142-16-5) → 2-(tetrahydro-2-furanyl) butanedioic acid 1,4-bis(2-ethylhexyl) ester + 2-(tetrahydro-2-furanyl) butanedioic acid 1,4-bis(2-ethylhexyl) ester

Conditions	Yield
With di-tert-butyl peroxide at 20℃; for 4h; UV-irradiation; Inert atmosphere; Overall yield = 96 percent; diastereoselective reaction;	A 59% B 29%

DL-thiomalic acid (70-49-5) + bis(2-ethylhexyl) maleate (142-16-5) → sodium 3-<<1,2-bis<<(2-ethylhexyl)oxy>carbonyl>ethyl>thio>succinate (135513-30-3)

Conditions	Yield
With sodium hydroxide In water; N,N-dimethyl-formamide	50%

bis(2-ethylhexyl) maleate (142-16-5) + ethylenediamine (107-15-3) → [S,S]-[R,R]-[R,S]-ethylenediaminedisuccinic acid tetraisooctyl ester

Conditions	Yield
In toluene at 20 - 80℃; for 4h; Heating / reflux;	30%

bis(2-ethylhexyl) maleate (142-16-5) → bis(2-ethylhexyl) sulfosuccinate (10041-19-7)

Conditions	Yield
With water; sodium hydrogensulfite at 100℃;
With ethanol; water; sodium hydrogensulfite at 100℃;
With ethanol; water; sodium hydrogensulfite at 100℃;
With water; sodium hydrogensulfite at 100℃;

bis(2-ethylhexyl) maleate (142-16-5) → 3-thia-pentane-1,2,4,5-tetracarboxylic acid tetrakis-(2-ethyl-hexyl ester)

Conditions	Yield
With hydrogen sulfide; triethylamine at 50℃;
With hydrogen sulfide; triethylamine at 50℃;

bis(2-ethylhexyl) maleate (142-16-5) + butyraldehyde (123-72-8) → butyryl-succinic acid bis-(2-ethyl-hexyl ester)

Conditions	Yield
With dibenzoyl peroxide

bis(2-ethylhexyl) maleate (142-16-5) + O,O-Diethyl hydrogen phosphorodithioate (298-06-6) → diethoxythiophosphorylsulfanyl-succinic acid bis-(2-ethyl-hexyl ester)

Conditions	Yield
With triethylamine; benzene

bis(2-ethylhexyl) maleate (142-16-5) + phosphonic acid diethyl ester (762-04-9) → diethoxyphosphoryl-succinic acid bis-(2-ethyl-hexyl ester) (78897-69-5)

bis(2-ethylhexyl) maleate (142-16-5) + dicyclohexylphosphonate → (bis-cyclohexyloxy-phosphoryl)-succinic acid bis-(2-ethyl-hexyl ester) (121706-67-0)

Conditions	Yield
With sodium amide

carbon disulfide (75-15-0) + bis(2-ethylhexyl) maleate (142-16-5) + 2-butylamino-ethanol (111-75-1) → C27H51NO5S2

Conditions	Yield
at 50 - 70℃; for 4h;

carbon disulfide (75-15-0) + bis(2-ethylhexyl) maleate (142-16-5) + 2,2'-iminobis[ethanol] (111-42-2) → C25H47NO6S2

Conditions	Yield
In isopropyl alcohol at 50 - 80℃; for 4h;

carbon disulfide (75-15-0) + bis(2-ethylhexyl) maleate (142-16-5) + 2-(Ethylamino)ethanol (110-73-6) → C25H47NO5S2

Conditions	Yield
at 50 - 70℃; for 5h;

bis(2-ethylhexyl) maleate (142-16-5) + N,N-dibenzylhydroxylamine (621-07-8) → Di-2-ethylhexyl-2-(N,N-dibenzylaminoxy)succinate (110878-62-1)

Conditions	Yield
In tetrahydrofuran

bis(2-ethylhexyl) maleate (142-16-5) + N-ethyl-N-hydroxy-ethanamine (3710-84-7) → Di-2-ethylhexyl-2-(N,N-diethylaminoxy)succinate (110878-63-2)

Conditions	Yield
In diethylene glycol dimethyl ether

bis(2-ethylhexyl) maleate (142-16-5) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → C29H58O7SSi

Conditions	Yield
With potassium tert-butylate In toluene at 0 - 20℃; for 1h;

bis(2-ethylhexyl) maleate (142-16-5) → sodium docusate (577-11-7)

Conditions	Yield
With sodium disulfite In water at 104℃; for 3.16667h; Inert atmosphere;

bis(2-ethylhexyl) maleate (142-16-5) + N-[(2,2,2-trifluoroethyliden)amino]acetamide (1564258-91-8) → bis(2-ethylhexyl) 3,4-cis-2-acetyl-5-(trifluoromethyl)pyrazolidine-3,4-dicarboxylate + bis(2-ethylhexyl) 3,4-trans-2-acetyl-5-(trifluoromethyl)pyrazolidine-3,4-dicarboxylate

Conditions	Yield
With potassium carbonate In toluene for 30h; Reflux; Overall yield = 47 %; Overall yield = 46 mg;	A n/a B n/a

bis(2-ethylhexyl) maleate (142-16-5) + C10H9F3N2O → bis(2-ethylhexyl) 3,4-cis-2-(2-methylbenzoyl)-5-(trifluoromethyl)-pyrazolidine-3,4-dicarboxylate + bis(2-ethylhexyl) 3,4-trans-2-(2-methylbenzoyl)-5-(trifluoromethyl)-pyrazolidine-3,4-dicarboxylate

Conditions	Yield
With potassium carbonate In toluene for 30h; Reflux; Overall yield = 80 %; Overall yield = 102 mg;	A n/a B n/a

p-Aminophenethylamine (13472-00-9) + bis(2-ethylhexyl) maleate (142-16-5) → C28H48N2O4

Conditions	Yield
for 24h;

Upstream product

• 108-31-6 maleic anhydride 
• 104-76-7 2-Ethylhexyl alcohol 
• 110-16-7 maleic acid 
• 589-98-0 rac-3-octanol 

Downstream Products

• 10041-19-7 bis(2-ethylhexyl) sulfosuccinate 
• 78897-69-5 diethoxyphosphoryl-succinic acid bis-(2-ethyl-hexyl ester) 
• 577-11-7 sodium docusate 
• 110878-62-1 Di-2-ethylhexyl-2-(N,N-dibenzylaminoxy)succinate 

Relevant articles and documents

Subsititue Material As Well As Production Process And Application

The invention relates to a production process of a functionalized material containing acid groups and an application thereof. The material is used as a nonhomogenous catalyst, and can be used for removing organic and inorganic compounds in product streams, process streams and waste liquid, or can be used as a cation and anion exchanger, a metal chromatography material, a solid phase purifying or extracting material, a fixed biological moleculaar material, a solid phase sythesizing material and a chromatography material. The invention also relates to a novel sulfonic acid or hypophosphorous organic funtionalized silica gel and metal salts thereof.

FUNCTIONALISED MATERIALS, PROCESS FOR THE PRODUCTION AND USES THEREOF

The invention relates both to processes for the production of functionalised materials containing alkyl sulfonic acids groups and their use as heterogeneous catalysts. The invention also relates to precursors of these new products and new organopolysiloxane sulfonic acids.

Chemistry in Water - Part VI. Catalytic Isomerization and Stereochemistry of Reduction of Acetylenics Mediated by Water-Soluble Phosphines

Reaction of water-soluble phosphines with disubstituted electrodeficient alkynes in H2O (D2O) gives rise either to mixtures of cis and trans (dideuterated) olefins or specifically to trans (dideuterated) olefins, by simple control of the phosphine amount.A cis-trans olefin isomerization catalyzed by sulfonated phosphines occurs in water and allows the obtention of specifically trans disubstituted alkenes from the corresponding cis isomers.