Product Name

  • Name

    ADIPIC ACID DIVINYL ESTER

  • EINECS
  • CAS No. 4074-90-2
  • Article Data20
  • CAS DataBase
  • Density 1.039g/cm3
  • Solubility
  • Melting Point 28 °C
  • Formula C10H14 O4
  • Boiling Point 261.1°Cat760mmHg
  • Molecular Weight 198.219
  • Flash Point 122.2°C
  • Transport Information
  • Appearance
  • Safety Low toxicity by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
  • Risk Codes
  • Molecular Structure Molecular Structure of 4074-90-2 (ADIPIC ACID DIVINYL ESTER)
  • Hazard Symbols
  • Synonyms Adipicacid, divinyl ester (6CI,7CI,8CI); Hexanedioic acid, diethenyl ester (9CI);Divinyl adipate; Divinyl hexanedioate
  • PSA 52.60000
  • LogP 1.92020

Synthetic route

vinyl acetate
108-05-4

vinyl acetate

Adipic acid
124-04-9

Adipic acid

divinyl adipate
4074-90-2

divinyl adipate

Conditions
ConditionsYield
With sulfuric acid; mercury(II) diacetate for 4h; Reflux; Inert atmosphere;52%
With mercury(II) sulfate
With sulfuric acid; mercury(II) diacetate; copper diacetate at 70℃;
With mercury(II) sulfate
trimethylsiloxyethene
6213-94-1

trimethylsiloxyethene

Adipic acid dichloride
111-50-2

Adipic acid dichloride

divinyl adipate
4074-90-2

divinyl adipate

Conditions
ConditionsYield
With potassium fluoride; 18-crown-6 ether In acetonitrile at 40 - 50℃; for 20h; Inert atmosphere;48%
Adipic acid
124-04-9

Adipic acid

ethene
74-85-1

ethene

divinyl adipate
4074-90-2

divinyl adipate

Conditions
ConditionsYield
With trihexyl(tetradecyl)phosphonium chloride; tetrabutyl-ammonium chloride; copper diacetate; tetrahexylammonium chloride; palladium; copper dichloride In 1,4-dioxane for 21h; Catalytic behavior; High pressure;16%
acetaldehyde
75-07-0

acetaldehyde

Adipic acid dichloride
111-50-2

Adipic acid dichloride

divinyl adipate
4074-90-2

divinyl adipate

Conditions
ConditionsYield
With pyridine
Adipic acid
124-04-9

Adipic acid

acetylene
74-86-2

acetylene

divinyl adipate
4074-90-2

divinyl adipate

Conditions
ConditionsYield
With chloroacetic acid; mercury(II) oxide at 80℃;
rhenium(I) pentacarbonyl chloride In toluene at 140℃; under 15001.5 Torr; for 6h; Product distribution / selectivity;96 %Chromat.
rhenium In toluene at 160℃; under 15001.5 Torr; for 6h; Product distribution / selectivity;
Adipic acid
124-04-9

Adipic acid

divinylmercury
1119-20-6

divinylmercury

divinyl adipate
4074-90-2

divinyl adipate

Conditions
ConditionsYield
In xylene for 1h; Heating;
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

disodium adipate

disodium adipate

divinyl adipate
4074-90-2

divinyl adipate

C22H26O6Se2

C22H26O6Se2

divinyl adipate
4074-90-2

divinyl adipate

Conditions
ConditionsYield
With diisopropylamine In chloroform for 12h; Reflux;0.15 g
divinyl adipate
4074-90-2

divinyl adipate

1H-4(5)-nitroimidazole
3034-38-6

1H-4(5)-nitroimidazole

1-(4-nitro-imidazol-1-yl)-ethyl vinyl adipate

1-(4-nitro-imidazol-1-yl)-ethyl vinyl adipate

Conditions
ConditionsYield
With Thermomyces lanuginosus lipase; potassium carbonate In dimethyl sulfoxide at 50℃; for 0.5h; Flow reactor; Enzymatic reaction;99%
With D-aminoacylase from Escherichia coli (EC 3.5.1.81) In dimethyl sulfoxide at 50℃; for 96h;95%
In various solvent(s) at 50℃; for 60h; Markovnikov's addition;94%
divinyl adipate
4074-90-2

divinyl adipate

ribavirin
36791-04-5

ribavirin

Hexanedioic acid (2R,3S,4R,5R)-5-(3-carbamoyl-[1,2,4]triazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester vinyl ester

Hexanedioic acid (2R,3S,4R,5R)-5-(3-carbamoyl-[1,2,4]triazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester vinyl ester

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; lipase acrylic resin from Candida antartica In acetone at 50℃; for 4h;96%
With [bmim]BF4; Candida antarctica lipase acrylic resin In acetone at 50℃; for 12h;98.5 % Chromat.
divinyl adipate
4074-90-2

divinyl adipate

5-nitrobenzimidazole
94-52-0

5-nitrobenzimidazole

C17H19N3O6

C17H19N3O6

Conditions
ConditionsYield
With Thermomyces lanuginosus lipase; potassium carbonate In dimethyl sulfoxide at 50℃; for 0.5h; Flow reactor; Enzymatic reaction;95%
dimethyl 2,2'-azobis(isobutyrate)
2589-57-3

dimethyl 2,2'-azobis(isobutyrate)

divinyl adipate
4074-90-2

divinyl adipate

polymer; monomer(s): divinyl adipate, 0.3 mol/l; dimethyl 2,2\-azobis(isobutyrate), 0.01 mol/l

polymer; monomer(s): divinyl adipate, 0.3 mol/l; dimethyl 2,2\-azobis(isobutyrate), 0.01 mol/l

Conditions
ConditionsYield
In benzene at 80℃; for 4h;93%
divinyl adipate
4074-90-2

divinyl adipate

Sucrose
57-50-1

Sucrose

sucrose-6-O-vinyl adipate

sucrose-6-O-vinyl adipate

Conditions
ConditionsYield
With thermomyces lanuginosus lipase immobilized on tetramethylorthosilicate and methyltrimethoxysilane (3:1 ratio) In N,N-dimethyl-formamide at 30 - 50℃; Molecular sieve; Enzymatic reaction; regioselective reaction;92.8%
divinyl adipate
4074-90-2

divinyl adipate

2-methyl-4-nitro-1H-imidazole
696-23-1

2-methyl-4-nitro-1H-imidazole

C14H19N3O6

C14H19N3O6

Conditions
ConditionsYield
With Thermomyces lanuginosus lipase; potassium carbonate In dimethyl sulfoxide at 50℃; for 0.5h; Flow reactor; Enzymatic reaction;92%
dimethyl 2,2'-azobis(isobutyrate)
2589-57-3

dimethyl 2,2'-azobis(isobutyrate)

divinyl adipate
4074-90-2

divinyl adipate

polymer, Mn 1.68E4 g/mol by GPC, Mw/Mn 13.0; monomer(s): divinyl adipate; dimethyl 2,2\-azobis(isobutyrate)

polymer, Mn 1.68E4 g/mol by GPC, Mw/Mn 13.0; monomer(s): divinyl adipate; dimethyl 2,2\-azobis(isobutyrate)

Conditions
ConditionsYield
In benzene at 80℃; for 4h;87%
divinyl adipate
4074-90-2

divinyl adipate

arbutin
497-76-7

arbutin

6-O-vinyladipoyl arbutin
681212-47-5

6-O-vinyladipoyl arbutin

Conditions
ConditionsYield
Streptomyces sp.-derived alkaline protease In pyridine at 30℃; for 96h; Product distribution / selectivity;85%
divinyl adipate
4074-90-2

divinyl adipate

4-nitrophenyl N-acetyl-β-D-glucosaminide
3459-18-5

4-nitrophenyl N-acetyl-β-D-glucosaminide

6-O-(p-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl) vinyl adipate
1261582-34-6

6-O-(p-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl) vinyl adipate

Conditions
ConditionsYield
With lipase from Candida antarctica In acetone at 45℃; for 12h; Molecular sieve; Enzymatic reaction; regioselective reaction;83%
divinyl adipate
4074-90-2

divinyl adipate

Sucrose
57-50-1

Sucrose

C20H32O14
359707-34-9

C20H32O14

Conditions
ConditionsYield
Candida antarctica-derived lipase type A In DMF (N,N-dimethyl-formamide) at 30℃; for 48h; Product distribution / selectivity;81%
divinyl adipate
4074-90-2

divinyl adipate

thymin
65-71-4

thymin

C15H20N2O6
1038531-21-3

C15H20N2O6

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 2.5h;80%
dimethyl 2,2'-azobis(isobutyrate)
2589-57-3

dimethyl 2,2'-azobis(isobutyrate)

divinyl adipate
4074-90-2

divinyl adipate

polymer, Mn 1.85E4 g/mol by GPC, Mw/Mn 12.7; monomer(s): divinyl adipate; dimethyl 2,2\-azobis(isobutyrate)

polymer, Mn 1.85E4 g/mol by GPC, Mw/Mn 12.7; monomer(s): divinyl adipate; dimethyl 2,2\-azobis(isobutyrate)

Conditions
ConditionsYield
In benzene at 80℃; for 4h;79%
divinyl adipate
4074-90-2

divinyl adipate

Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

O,O’-((terephthaloylbis(oxy))bis(ethane-2,1-diyl)) divinyl diadipate

O,O’-((terephthaloylbis(oxy))bis(ethane-2,1-diyl)) divinyl diadipate

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium Tetrafluoroborate; 2-hydroxyresorcinol In acetone at 65℃; for 40h; Enzymatic reaction;79%
divinyl adipate
4074-90-2

divinyl adipate

mephenesin
59-47-2

mephenesin

1-O-vinyladipoyl-mephenesin

1-O-vinyladipoyl-mephenesin

Conditions
ConditionsYield
With Lipozyme(R) In acetone at 50℃; for 2h;78.5%
(RS)-metoprolol
51384-51-1

(RS)-metoprolol

divinyl adipate
4074-90-2

divinyl adipate

N-(5-vinyloxycarbonylpentanoyl)metoprolol
1350627-08-5

N-(5-vinyloxycarbonylpentanoyl)metoprolol

Conditions
ConditionsYield
With Porcine pancreas lipase type II In tetrachloromethane at 50℃; for 72h; Enzymatic reaction;74%
divinyl adipate
4074-90-2

divinyl adipate

uracil
66-22-8

uracil

1-(uracil-1-yl)-ethyl vinyl adipate
1038531-17-7

1-(uracil-1-yl)-ethyl vinyl adipate

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 2.5h;73%
divinyl adipate
4074-90-2

divinyl adipate

chlorphenesin
104-29-0

chlorphenesin

1-O-vinyladipoyl-chlorphenesin

1-O-vinyladipoyl-chlorphenesin

Conditions
ConditionsYield
With Lipozyme(R) In acetone at 50℃; for 2h;72.5%
divinyl adipate
4074-90-2

divinyl adipate

thiocolchicoside
602-41-5

thiocolchicoside

C35H43NO13S
1261582-37-9

C35H43NO13S

Conditions
ConditionsYield
With lipase from Candida antarctica In acetone at 45℃; for 12h; Molecular sieve; Enzymatic reaction; regioselective reaction;72%
divinyl adipate
4074-90-2

divinyl adipate

phenyl-β-D-glucopyranoside
1464-44-4

phenyl-β-D-glucopyranoside

6-O-(phenyl β-D-glucopyranosyl) vinyl adipate
1261582-29-9

6-O-(phenyl β-D-glucopyranosyl) vinyl adipate

Conditions
ConditionsYield
With lipase from Candida antarctica In acetone at 45℃; for 12h; Molecular sieve; Enzymatic reaction; regioselective reaction;72%
D-Mannose
530-26-7

D-Mannose

divinyl adipate
4074-90-2

divinyl adipate

Hexanedioic acid (2R,3S,4S,5S)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester vinyl ester

Hexanedioic acid (2R,3S,4S,5S)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester vinyl ester

Conditions
ConditionsYield
With alkaline protease from Bacillus subtilis In pyridine at 50℃; for 96h;69%
dimethyl 2,2'-azobis(isobutyrate)
2589-57-3

dimethyl 2,2'-azobis(isobutyrate)

divinyl adipate
4074-90-2

divinyl adipate

polymer, Mn 1.71E4 g/mol by GPC, Mw/Mn 9.2; monomer(s): divinyl adipate; dimethyl 2,2\-azobis(isobutyrate)

polymer, Mn 1.71E4 g/mol by GPC, Mw/Mn 9.2; monomer(s): divinyl adipate; dimethyl 2,2\-azobis(isobutyrate)

Conditions
ConditionsYield
In benzene at 80℃; for 4h;68%
1H-imidazole
288-32-4

1H-imidazole

divinyl adipate
4074-90-2

divinyl adipate

C13H18N2O4

C13H18N2O4

Conditions
ConditionsYield
With Thermomyces lanuginosus lipase; potassium carbonate In dimethyl sulfoxide at 50℃; for 0.5h; Flow reactor; Enzymatic reaction;68%
divinyl adipate
4074-90-2

divinyl adipate

(rac)-mexiletine hydrochloride
5370-01-4

(rac)-mexiletine hydrochloride

C19H27NO4
1268813-08-6

C19H27NO4

Conditions
ConditionsYield
With sodium methylate In toluene for 12h; Inert atmosphere;67%
D-Glucose
2280-44-6

D-Glucose

divinyl adipate
4074-90-2

divinyl adipate

6-O-vinyladipoyl-D-glucopyranose

6-O-vinyladipoyl-D-glucopyranose

Conditions
ConditionsYield
With alkaline protease from Streptomyces sp In N,N-dimethyl-formamide at 35℃; for 96h;66%
With pyridine at 50℃; Enzymatic reaction;
divinyl adipate
4074-90-2

divinyl adipate

methyl shikimate
40983-58-2

methyl shikimate

C16H22O8

C16H22O8

Conditions
ConditionsYield
With immobilized lipase from Mucor miehei In acetone at 30℃; for 12h;65.1%
bis(2-hydroxyethyl)(2,2,4-trimethylhexane-1,6-diyl)dicarbamate

bis(2-hydroxyethyl)(2,2,4-trimethylhexane-1,6-diyl)dicarbamate

divinyl adipate
4074-90-2

divinyl adipate

O,O’-(7,7,9-trimethyl-4,13-dioxo-3,14-dioxa-5,12-diazahexadecane-1,16-diyl) divinyl diadipate

O,O’-(7,7,9-trimethyl-4,13-dioxo-3,14-dioxa-5,12-diazahexadecane-1,16-diyl) divinyl diadipate

Conditions
ConditionsYield
With 2-hydroxyresorcinol at 65℃; for 40h; Enzymatic reaction;65%
dimethyl 2,2'-azobis(isobutyrate)
2589-57-3

dimethyl 2,2'-azobis(isobutyrate)

divinyl adipate
4074-90-2

divinyl adipate

polymer; monomer(s): divinyl adipate, 0.5 mol/l; dimethyl 2,2\-azobis(isobutyrate), 0.5 mol/l

polymer; monomer(s): divinyl adipate, 0.5 mol/l; dimethyl 2,2\-azobis(isobutyrate), 0.5 mol/l

Conditions
ConditionsYield
In benzene at 80℃; for 4h;63%
divinyl adipate
4074-90-2

divinyl adipate

Isosorbide
652-67-5

Isosorbide

O,O'-(hexahydrofuro[3,2-b]furan-3,6-diyl) divinyl diadipate

O,O'-(hexahydrofuro[3,2-b]furan-3,6-diyl) divinyl diadipate

Conditions
ConditionsYield
With 2-hydroxyresorcinol In acetone at 65℃; for 40h; Enzymatic reaction;62%
divinyl adipate
4074-90-2

divinyl adipate

A

7-epipaclitaxel 2'-vinyl adipate

7-epipaclitaxel 2'-vinyl adipate

B

paclitaxel 2'-vinyl adipate
188593-01-3

paclitaxel 2'-vinyl adipate

Conditions
ConditionsYield
With thermolysin from Bacillus thermoproteolyticus Rokko In tert-Amyl alcohol at 35℃; for 96h;A 18%
B 60%
divinyl adipate
4074-90-2

divinyl adipate

troxerutin
7085-55-4

troxerutin

troxerutin vinyl adipate
1218941-81-1

troxerutin vinyl adipate

Conditions
ConditionsYield
With pyridine at 55℃; for 96h; Enzymatic reaction;60%
With pyridine; alkaline protease from Bacillus subtilis at 50℃; for 120h; Enzymatic reaction; regioselective reaction;

Divinyl adipate Chemical Properties

Hexanedioic acid diethyl ester(4074-90-2)'s molecular formula is C10H18O4 and its formula weight is 202.25.
The density of hexanedioic acid diethyl ester(4074-90-2) is 1.009 and it has a  melting point of -18°C. Its Boiling point is 251°C and the refractive index is about 1.426-1.428.
 Hexanedioic acid diethyl ester(4074-90-2) has the property of being dissolved in alcohols and ethers, it is not soluble in water.
The molecular structure of hexanedioic acid diethyl ester(4074-90-2) :

Divinyl adipate Uses

Hexanedioic acid diethyl ester(4074-90-2) is used as a plasticizer for cellulose acetate, cellulose acetate butyrate and  pyroxylin. It is also used as a organic solvent or  in organic synthesis.

Divinyl adipate Toxicity Data With Reference

1.   

orl-rat LD50:6400 mg/kg

   GISAAA    Gigiena i Sanitariya. 35 (10)(1970),88.
2.   

orl-mus LD50:6400 mg/kg

   GISAAA    Gigiena i Sanitariya. 35 (10)(1970),88.
3.   

orl-gpg LD50:4300 mg/kg

   GISAAA    Gigiena i Sanitariya. 35 (10)(1970),88.
4.   

orl-rbt LD50:4300 mg/kg

   GISAAA    Gigiena i Sanitariya. 35 (10)(1970),88.

Divinyl adipate Safety Profile

Low toxicity by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
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