4074-90-2

Basic information

• Product Name: ADIPIC ACID DIVINYL ESTER
• Synonyms: Hexanedioic acid 1,6-diethenyl ester;Divinyl Adipate DIVINYL ADIPATE;ADIPIC ACID DIVINYL ESTER;Divinyl hexanedioate;Hexanedioic acid, diethenyl ester;hexanedioicacid,diethenylester;Hexanedionic acid, diethenyl ester
• CAS NO: 4074-90-2
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.22
• EINECS: 223-792-1
• Mol File: 4074-90-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 28 °C
• Boiling Point: 261℃
• Flash Point: 28 °C
• Appearance: /
• Density: 1,05 g/cm3
• Vapor Pressure: 0.0118mmHg at 25°C
• Refractive Index: 1.4549
• Solubility: soluble in Methanol
• CAS DataBase Reference: ADIPIC ACID DIVINYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: ADIPIC ACID DIVINYL ESTER(4074-90-2)
• EPA Substance Registry System: ADIPIC ACID DIVINYL ESTER(4074-90-2)

Safety Data

• Safety Statements: 23-24/25
• RTECS: AV1800000
• Hazardous Substances Data: 4074-90-2(Hazardous Substances Data)

Usage

General Description

Adipic acid divinyl ester is a chemical compound that is derived from adipic acid, a carboxylic acid. It is a colorless liquid with a faint odor and is commonly used as a crosslinking agent in the production of polymers and resins. Adipic acid divinyl ester is also utilized in the manufacturing of coatings, adhesives, and plastics. It is considered to be a versatile compound with good chemical and thermal stability, making it suitable for a wide range of industrial applications. Additionally, it is known for its low volatility and low toxicity, making it relatively safe to handle and use in various processes.

InChI:InChI=1/C10H14O4/c1-3-13-9(11)7-5-6-8-10(12)14-4-2/h3-4H,1-2,5-8H2

Synthetic route

vinyl acetate (108-05-4) + Adipic acid (124-04-9) → divinyl adipate (4074-90-2)

Conditions	Yield
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) + Adipic acid dichloride (111-50-2) → divinyl adipate (4074-90-2)

Conditions	Yield
With potassium fluoride; 18-crown-6 ether In acetonitrile at 40 - 50℃; for 20h; Inert atmosphere;	48%

Adipic acid (124-04-9) + ethene (74-85-1) → divinyl adipate (4074-90-2)

Conditions	Yield
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) + Adipic acid dichloride (111-50-2) → divinyl adipate (4074-90-2)

Conditions	Yield
With pyridine

Adipic acid (124-04-9) + acetylene (74-86-2) → divinyl adipate (4074-90-2)

Conditions	Yield
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) + divinylmercury (1119-20-6) → divinyl adipate (4074-90-2)

Conditions	Yield
In xylene for 1h; Heating;

Vinyl chloroformate (5130-24-5) + disodium adipate → divinyl adipate (4074-90-2)

C22H26O6Se2 → divinyl adipate (4074-90-2)

Conditions	Yield
With diisopropylamine In chloroform for 12h; Reflux;	0.15 g

divinyl adipate (4074-90-2) + 1H-4(5)-nitroimidazole (3034-38-6) → 1-(4-nitro-imidazol-1-yl)-ethyl vinyl adipate

Conditions	Yield
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) + ribavirin (36791-04-5) → 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	Yield
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) + 5-nitrobenzimidazole (94-52-0) → C17H19N3O6

Conditions	Yield
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) + divinyl adipate (4074-90-2) → polymer; monomer(s): divinyl adipate, 0.3 mol/l; dimethyl 2,2\-azobis(isobutyrate), 0.01 mol/l

Conditions	Yield
In benzene at 80℃; for 4h;	93%

divinyl adipate (4074-90-2) + Sucrose (57-50-1) → sucrose-6-O-vinyl adipate

Conditions	Yield
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) + 2-methyl-4-nitro-1H-imidazole (696-23-1) → C14H19N3O6

Conditions	Yield
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) + divinyl adipate (4074-90-2) → polymer, Mn 1.68E4 g/mol by GPC, Mw/Mn 13.0; monomer(s): divinyl adipate; dimethyl 2,2\-azobis(isobutyrate)

Conditions	Yield
In benzene at 80℃; for 4h;	87%

divinyl adipate (4074-90-2) + arbutin (497-76-7) → 6-O-vinyladipoyl arbutin (681212-47-5)

Conditions	Yield
Streptomyces sp.-derived alkaline protease In pyridine at 30℃; for 96h; Product distribution / selectivity;	85%

divinyl adipate (4074-90-2) + 4-nitrophenyl N-acetyl-β-D-glucosaminide (3459-18-5) → 6-O-(p-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl) vinyl adipate (1261582-34-6)

Conditions	Yield
With lipase from Candida antarctica In acetone at 45℃; for 12h; Molecular sieve; Enzymatic reaction; regioselective reaction;	83%

divinyl adipate (4074-90-2) + Sucrose (57-50-1) → C20H32O14 (359707-34-9)

Conditions	Yield
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) + thymin (65-71-4) → C15H20N2O6 (1038531-21-3)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 2.5h;	80%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + divinyl adipate (4074-90-2) → polymer, Mn 1.85E4 g/mol by GPC, Mw/Mn 12.7; monomer(s): divinyl adipate; dimethyl 2,2\-azobis(isobutyrate)

Conditions	Yield
In benzene at 80℃; for 4h;	79%

divinyl adipate (4074-90-2) + Bis(2-Hydroxyethyl)terephthalat (959-26-2) → O,O’-((terephthaloylbis(oxy))bis(ethane-2,1-diyl)) divinyl diadipate

Conditions	Yield
With 1-butyl-3-methylimidazolium Tetrafluoroborate; 2-hydroxyresorcinol In acetone at 65℃; for 40h; Enzymatic reaction;	79%

divinyl adipate (4074-90-2) + mephenesin (59-47-2) → 1-O-vinyladipoyl-mephenesin

Conditions	Yield
With Lipozyme(R) In acetone at 50℃; for 2h;	78.5%

(RS)-metoprolol (51384-51-1) + divinyl adipate (4074-90-2) → N-(5-vinyloxycarbonylpentanoyl)metoprolol (1350627-08-5)

Conditions	Yield
With Porcine pancreas lipase type II In tetrachloromethane at 50℃; for 72h; Enzymatic reaction;	74%

divinyl adipate (4074-90-2) + uracil (66-22-8) → 1-(uracil-1-yl)-ethyl vinyl adipate (1038531-17-7)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 2.5h;	73%

divinyl adipate (4074-90-2) + chlorphenesin (104-29-0) → 1-O-vinyladipoyl-chlorphenesin

Conditions	Yield
With Lipozyme(R) In acetone at 50℃; for 2h;	72.5%

divinyl adipate (4074-90-2) + thiocolchicoside (602-41-5) → C35H43NO13S (1261582-37-9)

Conditions	Yield
With lipase from Candida antarctica In acetone at 45℃; for 12h; Molecular sieve; Enzymatic reaction; regioselective reaction;	72%

divinyl adipate (4074-90-2) + phenyl-β-D-glucopyranoside (1464-44-4) → 6-O-(phenyl β-D-glucopyranosyl) vinyl adipate (1261582-29-9)

Conditions	Yield
With lipase from Candida antarctica In acetone at 45℃; for 12h; Molecular sieve; Enzymatic reaction; regioselective reaction;	72%

D-Mannose (530-26-7) + divinyl adipate (4074-90-2) → Hexanedioic acid (2R,3S,4S,5S)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester vinyl ester

Conditions	Yield
With alkaline protease from Bacillus subtilis In pyridine at 50℃; for 96h;	69%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + divinyl adipate (4074-90-2) → polymer, Mn 1.71E4 g/mol by GPC, Mw/Mn 9.2; monomer(s): divinyl adipate; dimethyl 2,2\-azobis(isobutyrate)

Conditions	Yield
In benzene at 80℃; for 4h;	68%

1H-imidazole (288-32-4) + divinyl adipate (4074-90-2) → C13H18N2O4

Conditions	Yield
With Thermomyces lanuginosus lipase; potassium carbonate In dimethyl sulfoxide at 50℃; for 0.5h; Flow reactor; Enzymatic reaction;	68%

divinyl adipate (4074-90-2) + (rac)-mexiletine hydrochloride (5370-01-4) → C19H27NO4 (1268813-08-6)

Conditions	Yield
With sodium methylate In toluene for 12h; Inert atmosphere;	67%

D-Glucose (2280-44-6) + divinyl adipate (4074-90-2) → 6-O-vinyladipoyl-D-glucopyranose

Conditions	Yield
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) + methyl shikimate (40983-58-2) → C16H22O8

Conditions	Yield
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 + divinyl adipate (4074-90-2) → O,O’-(7,7,9-trimethyl-4,13-dioxo-3,14-dioxa-5,12-diazahexadecane-1,16-diyl) divinyl diadipate

Conditions	Yield
With 2-hydroxyresorcinol at 65℃; for 40h; Enzymatic reaction;	65%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + divinyl adipate (4074-90-2) → polymer; monomer(s): divinyl adipate, 0.5 mol/l; dimethyl 2,2\-azobis(isobutyrate), 0.5 mol/l

Conditions	Yield
In benzene at 80℃; for 4h;	63%

divinyl adipate (4074-90-2) + Isosorbide (652-67-5) → O,O'-(hexahydrofuro[3,2-b]furan-3,6-diyl) divinyl diadipate

Conditions	Yield
With 2-hydroxyresorcinol In acetone at 65℃; for 40h; Enzymatic reaction;	62%

divinyl adipate (4074-90-2) + taxol (33069-62-4) → 7-epipaclitaxel 2'-vinyl adipate + paclitaxel 2'-vinyl adipate (188593-01-3)

Conditions	Yield
With thermolysin from Bacillus thermoproteolyticus Rokko In tert-Amyl alcohol at 35℃; for 96h;	A 18% B 60%

divinyl adipate (4074-90-2) + troxerutin (7085-55-4) → troxerutin vinyl adipate (1218941-81-1)

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

Upstream product

• 108-05-4 vinyl acetate 
• 124-04-9 Adipic acid 
• 75-07-0 acetaldehyde 
• 111-50-2 Adipic acid dichloride 
• 74-86-2 acetylene 
• 1119-20-6 divinylmercury 
• 6213-94-1 trimethylsiloxyethene 
• 74-85-1 ethene 
• 5130-24-5 Vinyl chloroformate 

Downstream Products

• 188593-01-3 paclitaxel 2'-vinyl adipate 
• 681212-47-5 6-O-vinyladipoyl arbutin 
• 1218941-81-1 troxerutin vinyl adipate 
• 1261582-29-9 6-O-(phenyl β-D-glucopyranosyl) vinyl adipate 
• 1261582-34-6 6-O-(p-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl) vinyl adipate 
• 1350627-08-5 N-(5-vinyloxycarbonylpentanoyl)metoprolol 

Relevant articles and documents

Lectin recognizing thermoresponsive double hydrophilic glycopolymer micelles by RAFT polymerization

Thermoresponsive double hydrophilic block glycopolymer poly(N- isopropylacrylamide-co-6-O-vinyladipoyl-d-glucose)-b-poly(N-isopropylacrylamide) (P(NIPAm-co-OVAG)-b-PNIPAm) was prepared by a combination of enzymatic synthesis and reversible addition-fragment chain transfer (RAFT) polymerization protocols using P(NIPAm-co-OVAG) as a macro-RAFT agent. All the precisely synthesized glycopolymers were characterized by nuclear magnetic resonance spectroscopy and gel permeation chromatography. Detections using laser light scattering and transmission electron microscopy revealed that the block glycopolymer was able to self-assemble into micelles with various sizes and sphere morphologies in aqueous solutions. The glucose pendants in the glycopolymers had obvious interaction with lectin, concanavalin A (Con A), and their capacity of interaction with Con A was controlled by the number of glucose units in the glycopolymers. The block glycopolymer micelles have excellent biocompatibility with pig iliac endothelial cells using the MTT assay, however the glycopolymer-Con A micelles could be used to induce apoptosis in human hepatoma SMMC-7721 cells.

PROCESS FOR THE PRODUCTION OF HIGHER CARBOXYLIC ACID VINYL ESTERS

This invention concerns a process for the production of vinyl esters of carboxylic acids with 3 to 20 carbon atoms, via vinylation in the presence of palladium (Pd) catalyst in combination with copper (Cu) as co-catalyst stabilized by organic salts in the presence of ethylene and air or oxygen.

METHOD FOR PRODUCING VINYL ESTERS OF CARBOXYLIC ACIDS

The present invention relates to a process for preparing vinyl carboxylates, wherein a carboxylic acid is reacted with an alkyne compound in the presence of a catalyst which is selected from salts of perrhenic acid at a temperature of =250° C. The process gives rise to the desired vinyl esters with a high yield.