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140-88-5

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140-88-5 Usage

Chemical Description

Ethyl acrylate, ethyl crotonate, and diethyl fumarate are all esters that can be used in similar reactions.

Description

Ethyl acrylate, with the chemical formula CH2CHCO2CH2CH3, is an organic compound and the ethyl ester of acrylic acid. It is a colorless liquid with a characteristic acrid odor and is mainly produced for use in the manufacturing of paints, textiles, and non-woven fibers. Additionally, it serves as a reagent in the synthesis of various pharmaceutical intermediates.

Uses

1. Used in Polymer and Copolymer Production:
Ethyl acrylate is used as a monomer for the production of polymers and copolymers, which are utilized in manufacturing textiles, latex paints, paper coatings, dirt release agents, and specialty plastics.
2. Used in Acrylic Resins:
Ethyl acrylate is employed as a monomer for acrylic resins, which are essential components in various industries.
3. Used in Textile and Paper Coatings:
Ethyl acrylate is used as a component in the manufacture of acrylic resins, acrylic fibers, textile, and paper coatings, providing enhanced properties and performance.
4. Used in Adhesives and Leather Finish Resins:
Ethyl acrylate is also utilized in the production of adhesives and leather finish resins, contributing to their bonding and finishing properties.
5. Used as a Flavoring Agent:
Ethyl acrylate is used as a flavoring agent, characterized by its clear, colorless appearance, and a fruity, harsh, penetrating, and lachrymatous odor. It is sparingly soluble in water and miscible in alcohol and ether.
6. Used in Pharmaceutical Synthesis:
Ethyl acrylate serves as a reagent in the synthesis of various pharmaceutical intermediates, playing a crucial role in the development of new medications.
7. Used in the Production of Paints and Plastics:
Ethyl acrylate is used to make paints and plastics, thanks to its ability to polymerize and form useful materials with desirable properties.
8. Used in the Synthesis of Fragrances:
Ethyl acrylate's characteristic penetrating and persistent odor makes it a valuable component in the synthesis of fragrances, contributing to their unique scents.

Preparation

By esterification of acrylic acid; by heating acetylene with HCl in alcoholic solution in the presence of Ni(CO)4; also from ethyl-3-chloropropionate passed over activated carbon at high temperature.

Production Methods

Ethyl acrylate is manufactured via oxidation of propylene to acrolein and then to acrylic acid. The acid is treated with ethanol to yield the ethyl ester . Vinyl chloride reacts at 270 °C at >6895 kPa (68 atm) with ethanol in the presence of a cobalt and palladium catalyst to give ethyl acrylate in a yield of 17% .

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

A flammable liquid, confirmed carcinogen. Ethyl acrylate can react vigorously with oxidizing reagents, peroxides,strong alkalis and polymerization initiators. [NTP] Ethyl acrylate reacts violently with chlorosulfonic acid [Sax, 9th ed., 1996, p. 1515]. When an inhibited monomer was placed in a clear glass bottle exposed to sunlight, exothermic polymerization set in and caused the bottle to burst. The use of brown glass or metal containers and increase in inhibitor concentration (to 200 ppm; tenfold) was recommended [MCA Case History No. 1759]. Ethyl acrylate may polymerize when exposed to light and Ethyl acrylate is subject to slow hydrolysis. Inhibitors do not function in the absence of air. Solutions in DMSO are stable for 24 hours under normal lab conditions. [NTP].

Hazard

Toxic by ingestion, inhalation, skin absorption; irritant to skin and eyes. Flammable, dangerous fire and explosion hazard. Possible carcinogen.

Health Hazard

Ethyl acrylate is a strong irritant to the eyes,skin, and mucous membranes. The liquid orits concentrated solutions can produce skinsensitization upon contact. It is toxic by allroutes of exposure. The toxicity is low inrats and mice and moderate in rabbits. Thetoxic effects from inhalation noted in animalswere congestion of lungs and degenerativechanges in the heart, liver, and kidney. Mon key exposed to 272 ppm for 28 days showedlethargy and weight loss; while exposure to1024 ppm caused death to the animals after2.2 days (Treon et al. 1949). By compari son, guinea pigs died of exposure to about1200 ppm for 7 hours. Ingestion of the liq uid may result in irritation of gastrointestinaltracts, nausea, lethargy, and convulsionsThe LD50 values varied significantly indifferent species of animals. The oral LD50values in rabbits, rats, and mice are in therange 400, 800, and 1800 mg/kg, respectively. Animals administered ethyl acrylateshowed increased incidence of tumors inforestomach. However, there is no evidenceof carcinogenicity caused by this compoundin humans.

Flammability and Explosibility

Flammable

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: May occur; exclude moisture, light; avoid exposure to high temperatures; store in presence of air; Inhibitor of Polymerization: 13-17 ppm monomethyl ether of hydroquinone.

Safety Profile

Confirmed carcinogen with experimental carcinogenic data. Poison by ingestion and inhalation. Moderately toxic by skin contact and intraperitoneal routes. Human systemic effects by inhalation: eye, olfactory, and pulmonary changes. A skin and eye irritant. Characterized in its terminal stages by dyspnea, cyanosis, and convulsive movements. It caused severe local irritation of the gastroenteric tract; and toxic degenerative changes of cardiac, hepatic, renal, and splenic tissues were observed. It gave no evidence of cumulative effects. When applied to the intact skin of rabbits, the ethyl ester caused marked local irritation, erythema, edema, thickening, and vascular damage. Animals subjected to a fairly high concentration of these esters suffered irritation of the mucous membranes of the eyes, nose, and mouth as well as lethargy, dpspnea, and convulsive movements. A substance that migrates to food from packagmg materials. Flammable liquid. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. Violent reaction with chlorosulfonic acid. To fight fire, use CO2, dry chemical, or alcohol foam. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

Safety

It is an acute toxin with an LD50 (rats, oral) of 1020 mg / kg and a TLV of 5 ppm. The International Agency for Research on Cancer stated, "Overall evaluation, Ethyl acrylate is possibly carcinogenic to humans (Group 2B)." The United States Environmental Protection Agency (EPA) states, "Human studies on occupational exposure to ethyl acrylate... have suggested a relationship between exposure to the chemical(s) and colorectal cancer, but the evidence is conflicting and inconclusive. In a study by the National Toxicology Program (NTP), increased incidences of squamous cell papillomas and carcinomas of the fore stomach were observed in rats and mice exposed via gavage (experimentally placing the chemical in the stomach). However, the NTP recently determined that these data were not relevant to human carcinogenicity since humans do not have a fore stomach, and removed ethyl acrylate from its list of carcinogens." (Occupational exposure generally involves exposure that occurs regularly, over an extended period of time.) One favorable safety aspect is that ethyl acrylate has good warning properties; the odor threshold is much lower than any level of health concern. In other words, the bad odor warns people of ethyl acrylate's presence long before the concentration reaches a level capable of creating a serious health risk.

Potential Exposure

This material is used in emulsion polymers for paints, textiles, adhesives, coatings and binders; as a monomer in the manufacture of homopolymer and copolymer resins for the production of paints and plastic films

Carcinogenicity

A retrospective study found an excess of colorectal cancers in one exposed population of workers; however, the data were confounded by other exposures and lack of association of causality and risk in similarly exposed populations from other locations. Therefore, there was inadequate evidence based on the study that ethyl acrylate is a human carcinogen . Ethyl acrylate is listed as USEPA group B2, “Probable human carcinogen”; IARC group B2, “Possibly carcinogenic in humans”; NIOSH, “Carcinogen with no further categorization”; NTP group 2, “Reasonably anticipated to be a carcinogen” and listed as a carcinogen by California Proposition 65 . Dermal studies of acrylic acid, ethyl acrylate, and n-butyl acrylate using mice did not result in local carcinogenesis, but several mice in the ethyl acrylate-treated group did exhibit dermatitis, dermal fibrosis, epidermal necrosis, and hyperkeratosis .

Environmental fate

Chemical/Physical. Polymerizes on standing and is catalyzed by heat, light, and peroxides (Windholz et al., 1983). Slowly hydrolyzes in water forming ethanol and acrylic acid. The reported rate constant for the reaction of ethyl acrylate with ozone in the gas phase was determined to be 5.70 x 10-18 cm3 mol/sec (Munshi et al., 1989). At an influent concentration of 1,015 mg/L, treatment with GAC resulted in an effluent concentration of 226 mg/L. The adsorbability of the carbon used was 157 mg/g carbon (Guisti et al., 1974).

Shipping

UN1917 Ethyl acrylate, Hazard Class: 3; Labels: 3-Flammable liquid

Purification Methods

Wash the ester repeatedly with aqueous NaOH until free from inhibitors such as hydroquinone, then wash it with saturated aqueous CaCl2 and distil it under reduced pressure. Hydroquinone should be added if the ethyl acrylate is to be stored for extended periods. [Beilstein 2 IV 1460.] LACHRYMATORY.

Toxicity evaluation

The toxic mode of action for ethyl acrylate is unknown. However, the parent compound may play a significant role since pretreatment of rats with a carboxylesterase inhibitor enhances the respiratory irritation and lethality produced by the inhalation of ethyl acrylate. The enhanced toxicity could be a direct effect of methyl acrylate on surrounding tissues and/or a secondary effect due to the increased conjugation of methyl acrylate with glutathione that occurs under these conditions which in turn can result in toxicity due to the depletion of local glutathione stores.

Incompatibilities

May form explosive mixture with air. Atmospheric moisture and strong alkalies may cause fire and explosions unless properly inhibited (Note: Inert gas blanket not recommended). Heat, light or peroxides can cause polymerization. Incompatible with oxidizers (may be violent), peroxides, polymerizers, strong alkalis; moisture, chlorosulfonic acid, strong acids; amines. May accumulate static electrical charges, and may cause ignition of its vapors. Polymerizes readily unless an inhibitor, such as hydroquinone is added. Uninhibited vapors may plug vents by the formation of polymers.

Waste Disposal

Incineration or by absorption and landfill disposal

Check Digit Verification of cas no

The CAS Registry Mumber 140-88-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 0 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 140-88:
(5*1)+(4*4)+(3*0)+(2*8)+(1*8)=45
45 % 10 = 5
So 140-88-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O2/c1-3-4(2)5(6)7/h2-3H2,1H3,(H,6,7)/p-1

140-88-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A15493)  Ethyl acrylate, 99%, stab. with ca 20ppm 4-methoxyphenol   

  • 140-88-5

  • 100ml

  • 185.0CNY

  • Detail
  • Alfa Aesar

  • (A15493)  Ethyl acrylate, 99%, stab. with ca 20ppm 4-methoxyphenol   

  • 140-88-5

  • 500ml

  • 231.0CNY

  • Detail
  • Alfa Aesar

  • (A15493)  Ethyl acrylate, 99%, stab. with ca 20ppm 4-methoxyphenol   

  • 140-88-5

  • 2500ml

  • 1025.0CNY

  • Detail
  • Alfa Aesar

  • (15400)  Ethyl acrylate, 99%, stab. with 65ppm MEHQ   

  • 140-88-5

  • 1kg

  • 493.0CNY

  • Detail
  • Sigma-Aldrich

  • (76130)  Ethylacrylate  analytical standard

  • 140-88-5

  • 76130-5ML-F

  • 685.62CNY

  • Detail
  • Aldrich

  • (E9706)  Ethylacrylate  contains 10-20 ppm MEHQ as inhibitor, 99%

  • 140-88-5

  • E9706-100ML

  • 418.86CNY

  • Detail
  • Aldrich

  • (E9706)  Ethylacrylate  contains 10-20 ppm MEHQ as inhibitor, 99%

  • 140-88-5

  • E9706-1L

  • 678.60CNY

  • Detail
  • Aldrich

  • (E9706)  Ethylacrylate  contains 10-20 ppm MEHQ as inhibitor, 99%

  • 140-88-5

  • E9706-2L

  • 1,275.30CNY

  • Detail
  • Aldrich

  • (E9706)  Ethylacrylate  contains 10-20 ppm MEHQ as inhibitor, 99%

  • 140-88-5

  • E9706-10L

  • 2,468.70CNY

  • Detail

140-88-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl acrylate

1.2 Other means of identification

Product number -
Other names Acrylic Acid Ethyl Ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Ethyl acrylate is used in the manufacture of water-based latex paints and adhesives, textile and paper coatings, leather finish resins, and in the production of acrylic fibers.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:140-88-5 SDS

140-88-5Synthetic route

ethyl 3-(trifluoromethanesulfonyl)propionate
155201-03-9

ethyl 3-(trifluoromethanesulfonyl)propionate

A

Langlois reagent
2926-29-6

Langlois reagent

B

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃;A 100%
B n/a
ethanol
64-17-5

ethanol

acrylic acid
79-10-7

acrylic acid

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With iron(III) sulfate; sulfuric acid for 3h; Heating;98%
In neat (no solvent) at 80℃; for 2.5h;89%
With sulfuric acid for 12h; Reflux;82%
2,3-dibromopropionic acid ethyl ester
3674-13-3

2,3-dibromopropionic acid ethyl ester

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; sodium carbonate In dimethyl sulfoxide at 20℃; for 1.5h; Inert atmosphere; Irradiation;95%
With ethanol; sulfuric acid; zinc
With ethanol; zinc
With diethyl ether; zinc
With 2-methoxy-phenylamine In tetrahydrofuran at 20℃; stereospecific reaction;
Ethyl 3-bromopropionate
539-74-2

Ethyl 3-bromopropionate

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With P(MeNCH2CH2)3N In acetonitrile at 25℃; for 0.0833333h;92%
Multi-step reaction with 2 steps
1: 83 percent / dimethylformamide / 1.) 55 deg C, 60 h, 2.) room temperature, 6 h
2: 100 °C
View Scheme
With indole; dichloro bis(acetonitrile) palladium(II); potassium carbonate; norbornene In N,N-dimethyl acetamide; water Schlenk technique; Inert atmosphere; regioselective reaction;
ethene
74-85-1

ethene

acrylic acid
79-10-7

acrylic acid

A

diethyl ether
60-29-7

diethyl ether

B

ethanol
64-17-5

ethanol

C

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With water; cesium nitrate; tungstophosphoric acid; water; mixture of, dried, tabletted at 85.6 - 165℃; under 2250.23 Torr; Product distribution / selectivity; Gas phase;A 3.5%
B 4.3%
C 91.8%
{(NP3)RhH}
85233-91-6

{(NP3)RhH}

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

(N(CH2CH2P(C6H5)2)3Rh(C2CO2C2H5))

(N(CH2CH2P(C6H5)2)3Rh(C2CO2C2H5))

B

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
In tetrahydrofuran N2 or Ar atmosphere; refluxing (3 h, ratio Rh-compd. org. compd. 1:10), cooling (room temp.); addn. of EtOH, washing (EtOH and pentane), drying (N2 stream); elem. anal.;A 90%
B 8-15
In tetrahydrofuran N2 or Ar atmosphere; stirring (room temp., 24 h, ratio Rh-compd. org. compd. 1:10); addn. of EtOH, slow evapn., washing (EtOH and pentane), drying (N2 stream); elem. anal.;A 90%
B 8-15
formaldehyd
50-00-0

formaldehyd

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
In benzene Wittig reaction; Reflux;87%
In 1,4-dioxane at 50℃; for 16h;
formaldehyd
50-00-0

formaldehyd

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With potassium carbonate In water at 30℃; for 0.166667h;77%
With potassium carbonate In 1,4-dioxane at 70℃; for 5h;75%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 25℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;
Stage #2: formaldehyd In tetrahydrofuran; paraffin oil at 0 - 25℃; for 0.166667h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In toluene at 0℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Schlenk technique;
Stage #2: formaldehyd at 20℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Schlenk technique;
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 20 - 40℃; for 1h;
Stage #2: formaldehyd In tetrahydrofuran at 40℃; for 5h;
1-(trimethylsilyl)piperidin-2-one
3553-93-3

1-(trimethylsilyl)piperidin-2-one

Ethyl 2-bromopropionate
535-11-5, 41978-69-2

Ethyl 2-bromopropionate

A

piperidin-2-one
675-20-7

piperidin-2-one

B

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

C

2-(2-Oxo-piperidin-1-yl)-propionic acid ethyl ester

2-(2-Oxo-piperidin-1-yl)-propionic acid ethyl ester

D

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
at 155 - 180℃; for 3h; Yields of byproduct given;A n/a
B n/a
C 73%
D n/a
Ethyl 3-bromopropionate
539-74-2

Ethyl 3-bromopropionate

A

ethyl 3-hydroxypropanoate
623-72-3

ethyl 3-hydroxypropanoate

B

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With oxygen; tetraethylammonium perchlorate In N,N-dimethyl-formamide at 20℃; electroreduction at -1.1 V;A 70%
B 20 % Chromat.
With oxygen In N,N-dimethyl-formamide at 20℃; Product distribution; electrolysis of the oxygen saturated solution at -1,1 V; 0.1 M TEAP; further esters;A 70%
B 20 % Chromat.
Ethyl 2-bromopropionate
535-11-5, 41978-69-2

Ethyl 2-bromopropionate

1-trimethylsilanyl-azepan-2-one
3553-94-4

1-trimethylsilanyl-azepan-2-one

A

caprolactam
105-60-2

caprolactam

B

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

C

2-(2-Oxo-azepan-1-yl)-propionic acid ethyl ester

2-(2-Oxo-azepan-1-yl)-propionic acid ethyl ester

D

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
at 150 - 185℃; for 3h; Yields of byproduct given;A n/a
B n/a
C 65%
D n/a
zirconocene dichloride
1291-32-3

zirconocene dichloride

2-bromo-acrylic acid ethyl ester
5459-35-8

2-bromo-acrylic acid ethyl ester

hex-3-yne
928-49-4

hex-3-yne

A

ethyl 2,3,4,5-tetraethylbenzoate
1219618-63-9

ethyl 2,3,4,5-tetraethylbenzoate

B

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
Stage #1: zirconocene dichloride With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: hex-3-yne In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #3: 2-bromo-acrylic acid ethyl ester Further stages;
A 63%
B n/a
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

benzaldehyde
100-52-7

benzaldehyde

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
C-200 (barium hydroxide) In tetrahydrofuran; water for 0.166667h; Ambient temperature; sonication;57%
zirconocene dichloride
1291-32-3

zirconocene dichloride

2-bromo-acrylic acid ethyl ester
5459-35-8

2-bromo-acrylic acid ethyl ester

4-Octyne
1942-45-6

4-Octyne

A

ethyl 2,3,4,5-tetrapropylbenzoate
1219618-70-8

ethyl 2,3,4,5-tetrapropylbenzoate

B

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
Stage #1: zirconocene dichloride With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: 4-Octyne In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #3: 2-bromo-acrylic acid ethyl ester Further stages;
A 57%
B n/a
ethyl 3-hydroxypropanoate
623-72-3

ethyl 3-hydroxypropanoate

A

acrylic acid
79-10-7

acrylic acid

B

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With ethanol; sulfuric acid; copper at 220℃; Product distribution / selectivity;A 50%
B 50 %Chromat.
With ethanol; NaH2PO4-silica at 250 - 275℃; Product distribution / selectivity;A 21%
B 14 - 49 %Chromat.
2-(2-(ethoxycarbonyl)ethylthio)pyridine N-oxide

2-(2-(ethoxycarbonyl)ethylthio)pyridine N-oxide

A

2-ethylthiopyridine
19006-76-9

2-ethylthiopyridine

B

(propionate d'ethyle-3)(pyridyl-2) sulfure
89407-42-1

(propionate d'ethyle-3)(pyridyl-2) sulfure

C

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
at 220℃; under 1 Torr;A 13%
B 16%
C 43%
at 220℃; under 1 Torr; Product distribution; other conditions, other substrates;A 13%
B 16%
C 43%
ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

acetylene
74-86-2

acetylene

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With bis(acetylacetonate)nickel(II); sodium acetylacetonate In tetrahydrofuran at 220℃; under 1500.15 - 35253.5 Torr; for 1h; Autoclave;42.1%
With copper(ll) bromide; nickel dibromide In tetrahydrofuran at 240℃; under 3750.38 Torr;
With 2-Picolinic acid In tetrahydrofuran at 210℃; under 1500.15 - 37503.8 Torr; for 0.5h; Autoclave; Inert atmosphere;
With 8-hydroxy-quinoline-2-carboxylic acid; triethylaluminum; nickel(II) acetate tetrahydrate; triphenylphosphine In tetrahydrofuran at 60℃; under 10501.1 - 12001.2 Torr; for 1h; Autoclave; Inert atmosphere;
N-trimethylsilyl-pyrrolidin-2-one
14468-90-7

N-trimethylsilyl-pyrrolidin-2-one

Ethyl 2-bromopropionate
535-11-5, 41978-69-2

Ethyl 2-bromopropionate

A

2-pyrrolidinon
616-45-5

2-pyrrolidinon

B

ethyl 2-(2-oxo-1-pyrrolidinyl)propanoate
70717-55-4

ethyl 2-(2-oxo-1-pyrrolidinyl)propanoate

C

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

D

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
at 170 - 200℃; for 3h; Yields of byproduct given;A n/a
B 37%
C n/a
D n/a
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

ethene
74-85-1

ethene

A

styrene
292638-84-7

styrene

B

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
Hoveyda-Grubbs catalyst second generation In dichloromethane at 40℃; under 562.556 Torr; for 24h; Product distribution / selectivity; Inert atmosphere;A 19%
B 28%
With Hoveyda-Grubbs catalyst second generation at 25℃; under 13187.6 Torr; for 21h; Catalytic behavior; Reagent/catalyst;A n/a
B 6.2%
zirconocene dichloride
1291-32-3

zirconocene dichloride

2-bromo-acrylic acid ethyl ester
5459-35-8

2-bromo-acrylic acid ethyl ester

diphenyl acetylene
501-65-5

diphenyl acetylene

A

ethyl-5',6'-diphenyl-[1,1':2',1''-terphenyl]-3'-carboxylate
96676-89-0

ethyl-5',6'-diphenyl-[1,1':2',1''-terphenyl]-3'-carboxylate

B

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
Stage #1: zirconocene dichloride With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: diphenyl acetylene In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #3: 2-bromo-acrylic acid ethyl ester Further stages;
A 26%
B n/a
1-butylene
106-98-9

1-butylene

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

A

styrene
292638-84-7

styrene

B

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
Hoveyda-Grubbs catalyst second generation In dichloromethane at 40℃; under 750.075 Torr; for 24h; Inert atmosphere;A 8%
B 8%
ethene
74-85-1

ethene

diethyl Fumarate
623-91-6

diethyl Fumarate

A

diethylitaconate
2409-52-1

diethylitaconate

B

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
Hoveyda-Grubbs catalyst second generation at 60℃; under 7757.43 Torr; for 4h; Conversion of starting material;A 4%
B 7%
ethene
74-85-1

ethene

diethyl Fumarate
623-91-6

diethyl Fumarate

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
[1,3-bis(2-methylphenyl)-2-(imidazolidene)dichloro(phenylmethylene)(tricyclohexylphosphine)]ruthenium (II) at 60℃; under 7757.43 Torr; for 4h; Conversion of starting material;1%
dichloro(tricyclohexylphosphino)(benzylidene)(1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)ruthenium(III) at 60℃; under 7757.43 Torr; for 4h; Conversion of starting material;1%
[1,3-bis(2,4,6-trimethylphenyl)-2-(imidazolidene)dichloro(3-methyl-2-butenylidene)(tricyclohexylphosphine)]ruthenium (II) at 60℃; under 7757.43 Torr; for 16h; Conversion of starting material;1%
formic acid
64-18-6

formic acid

potassium formate
590-29-4

potassium formate

1-(2-carbethoxyethyl)pyridinium bromide
86931-46-6

1-(2-carbethoxyethyl)pyridinium bromide

A

pyridine
110-86-1

pyridine

B

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 2-hydroxypropionate
97-64-3, 2676-33-7

ethyl 2-hydroxypropionate

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
at 450℃; ueber einen aus Natriumdihydrogenphosphat und Graphit hergestellten Katalysator;
Multi-step reaction with 2 steps
1: pyridine; diethyl ether; SOCl2 / -10 °C
2: 390 - 420 °C
View Scheme
Multi-step reaction with 2 steps
1: concentrated H2SO4 / bei der Destillation
2: quartz / 450 °C
View Scheme
diethyl sulfate
64-67-5

diethyl sulfate

β-Propiolactone
57-57-8

β-Propiolactone

ethyl acrylate
140-88-5

ethyl acrylate

β-Propiolactone
57-57-8

β-Propiolactone

ethyl sulfate
540-82-9

ethyl sulfate

ethanol
64-17-5

ethanol

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With iron(II) sulfate at 140℃;
β-Propiolactone
57-57-8

β-Propiolactone

ethanol
64-17-5

ethanol

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With pyrographite at 250℃;
With sulfuric acid; hydroquinone
Vinyl bromide
593-60-2

Vinyl bromide

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With ethanol; tetracarbonyl nickel at 190℃;
3-amino-propionic acid ethyl ester
924-73-2

3-amino-propionic acid ethyl ester

ethyl acrylate
140-88-5

ethyl acrylate

piperidine
110-89-4

piperidine

ethyl acrylate
140-88-5

ethyl acrylate

ethyl piperidine-1-propionate
19653-33-9

ethyl piperidine-1-propionate

Conditions
ConditionsYield
cobalt(II) acetate In water at 20℃; for 15h; aza-type Michael addition;100%
ammonium cerium(IV) nitrate for 0.333333h; aza-Michael addition; ultrasonication;100%
With ammonium cerium(IV) nitrate In water at 20℃; for 12h; aza-Michael addition;99%
isopropylamine
75-31-0

isopropylamine

ethyl acrylate
140-88-5

ethyl acrylate

3-isopropylaminopropionic acid ethyl ester
16217-22-4

3-isopropylaminopropionic acid ethyl ester

Conditions
ConditionsYield
In tetrahydrofuran; ethanol at 0 - 20℃; for 16h;100%
In ethanol at 0 - 20℃; for 24h;100%
With poly(ethylene glycol) 2000; ruthenium trichloride at 50℃; for 8h; aza-Michael addition;91%
diethylamine
109-89-7

diethylamine

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 3-(diethylamino)propionate
5515-83-3

ethyl 3-(diethylamino)propionate

Conditions
ConditionsYield
With copper diacetate In water at 20℃; for 12h; aza-Michael addition;100%
iron(III) chloride In dichloromethane at 25℃; for 42h; Product distribution; various catalysts and further amines with various Michael acceptors;96%
iron(III) chloride In dichloromethane at 25℃; for 42h;96%
N-butylamine
109-73-9

N-butylamine

ethyl acrylate
140-88-5

ethyl acrylate

ethyl N-(n-butyl)-b-aminopropionate
10494-81-2

ethyl N-(n-butyl)-b-aminopropionate

Conditions
ConditionsYield
In ethanol at 20℃; for 2h; Michael addition;100%
With poly(ethylene glycol) 2000; ruthenium trichloride at 50℃; for 8h; aza-Michael addition;96%
Stage #1: N-butylamine With cerous nitrate for 4h; Reflux;
Stage #2: ethyl acrylate for 8h; Time;
93.8%
ethyl acrylate
140-88-5

ethyl acrylate

1-dodecylthiol
112-55-0

1-dodecylthiol

ethyl 3-n-dodecylthiopropionate
34137-13-8

ethyl 3-n-dodecylthiopropionate

Conditions
ConditionsYield
In acetonitrile electrolysis (0.01-0.1 N Et4NBr or Bu4NBr, Pt cathode, Mg anode);100%
With dibenzoyl peroxide at 240℃;
ethyl acrylate
140-88-5

ethyl acrylate

2,3-dibromopropionic acid ethyl ester
3674-13-3

2,3-dibromopropionic acid ethyl ester

Conditions
ConditionsYield
With bromine In acetone for 0.5h; Reflux;100%
With bromine In tetrachloromethane at 0 - 60℃; for 2h;99%
With bromine In dichloromethane at 0 - 20℃; for 4.33333h; Inert atmosphere;95%
ethyl acrylate
140-88-5

ethyl acrylate

Ethyl nipecotate
71962-74-8

Ethyl nipecotate

ethyl 1-[2-(ethoxycarbonyl)ethyl]-3-piperidinecarboxylate
128200-19-1

ethyl 1-[2-(ethoxycarbonyl)ethyl]-3-piperidinecarboxylate

Conditions
ConditionsYield
at 55℃;100%
In toluene at 18 - 52℃; for 12.9167 - 13.1667h;100%
In toluene at 18 - 52℃; for 12.9167 - 13.1667h; Product distribution / selectivity;97.6%
propylamine
107-10-8

propylamine

ethyl acrylate
140-88-5

ethyl acrylate

diethyl 3,3’-(propylazanediyl)dipropanoate
3619-65-6

diethyl 3,3’-(propylazanediyl)dipropanoate

Conditions
ConditionsYield
iron(III) chloride In water at 20℃; for 15h; aza-type Michael addition;100%
3-methoxy-N-methylaniline
14318-66-2

3-methoxy-N-methylaniline

ethyl acrylate
140-88-5

ethyl acrylate

3-(N-Methyl-N-m-methoxyphenylamino)-propionsaeure-aethylester
7280-98-0

3-(N-Methyl-N-m-methoxyphenylamino)-propionsaeure-aethylester

Conditions
ConditionsYield
at 60℃; for 2h;100%
In acetic acid
ethyl acrylate
140-88-5

ethyl acrylate

N,N-bis-[2-(ethylcarboxylato)ethyl]hydroxylamine
1609-27-4

N,N-bis-[2-(ethylcarboxylato)ethyl]hydroxylamine

Conditions
ConditionsYield
With hydroxylamine; triphenylphosphine In acetonitrile at 20℃; for 0.25h; Michael addition;100%
With hydroxylamine hydrochloride; sodium hydroxide In methanol for 0.25h; Inert atmosphere;72%
With hydroxylamine In methanol
With hydroxylamine hydrochloride; ammonia In ethanol at 20℃; for 15h;
piperidin-2-one
675-20-7

piperidin-2-one

ethyl acrylate
140-88-5

ethyl acrylate

1-(2-ethoxycarbonylethyl)-2-piperidinone
88948-40-7

1-(2-ethoxycarbonylethyl)-2-piperidinone

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran Michael addition reaction;100%
With tetraethoxy orthosilicate; cesium fluoride In neat (no solvent) at 25℃; for 0.166667h; Product distribution; Mechanism; variation of reaction time and amount of CsF; further α,β-unsaturated esters; further amides; presence of different solvents;98%
With tetraethoxy orthosilicate; cesium fluoride In neat (no solvent) at 25℃; for 0.166667h;98%
caprolactam
105-60-2

caprolactam

ethyl acrylate
140-88-5

ethyl acrylate

3-(2-Oxo-azepan-1-yl)-propionic acid ethyl ester
88948-41-8

3-(2-Oxo-azepan-1-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran Michael addition reaction;100%
With tetraethoxy orthosilicate; cesium fluoride In neat (no solvent) at 25℃; for 1h;89%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethyl acrylate
140-88-5

ethyl acrylate

diethyl Δ2-pyrazoline-3,5-dicarboxylate
82706-83-0

diethyl Δ2-pyrazoline-3,5-dicarboxylate

Conditions
ConditionsYield
at 22℃; for 5h;100%
In pyridine at 60℃; for 3h;99%
With water at 20℃; for 3h; Green chemistry;99%
tryptamine
61-54-1

tryptamine

ethyl acrylate
140-88-5

ethyl acrylate

3-<<2-(1H-indol-3-yl)ethyl>amino>propanoic acid ethyl ester
14487-98-0

3-<<2-(1H-indol-3-yl)ethyl>amino>propanoic acid ethyl ester

Conditions
ConditionsYield
In ethanol for 1h; Reflux;100%
In ethanol at 0℃; for 24h;83%
In tetrahydrofuran at 20℃; for 12h;83%
In ethanol at 0 - 20℃;80%
In ethanol
acetaldehyde
75-07-0

acetaldehyde

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 3-hydroxy-2-methylenebutanoate
98837-34-4, 130196-00-8, 19362-99-3

ethyl 3-hydroxy-2-methylenebutanoate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 216h;100%
With 1,4-diaza-bicyclo[2.2.2]octane at 25℃; for 168h;94%
1,4-diaza-bicyclo[2.2.2]octane for 168h; Ambient temperature;90%
thiophenol
108-98-5

thiophenol

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 3-(phenylthio)propionate
60805-64-3

ethyl 3-(phenylthio)propionate

Conditions
ConditionsYield
triethylamine Ambient temperature;100%
In acetonitrile electrolysis (0.01-0.1 N Et4NBr or Bu4NBr, Pt cathode, Mg anode);100%
perchloric acid; silica gel In dichloromethane at 20℃; for 0.166667h; thia-Michael addition;95%
2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 3-((2-hydroxyethyl)thio)propionate
77475-66-2

ethyl 3-((2-hydroxyethyl)thio)propionate

Conditions
ConditionsYield
In acetonitrile electrolysis (0.01-0.1 N Et4NBr or Bu4NBr, Pt cathode, Mg anode);100%
With triethylamine In methanol; acetone at 0 - 20℃; for 16h; Product distribution / selectivity;100%
With C15H22N4O4 In neat (no solvent) for 1h; Michael Addition; Irradiation;100 %Spectr.
bromobenzene
108-86-1

bromobenzene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl cinnamate
4192-77-2

ethyl cinnamate

Conditions
ConditionsYield
With potassium phosphate; tetrabutylammomium bromide; [PdCl{[η5-C5H5)]Fe[(η5-C5H3)C(CH3)=NC12H25]}]2 In N,N-dimethyl-formamide at 140℃; for 12h; Heck coupling;100%
With {4-[di(2-hydroxyethyl)amino]butyl}tri(n-butyl)ammonium bromide; palladium diacetate at 100℃; for 6h; Heck reaction; Inert atmosphere; stereoselective reaction;99%
With C37H38BrClFeN3Pd; potassium acetate In N,N-dimethyl acetamide at 150℃; for 12h; Heck reaction; Inert atmosphere; regioselective reaction;97%
iodobenzene
591-50-4

iodobenzene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl cinnamate
4192-77-2

ethyl cinnamate

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium acetate; Pd(0)-ferrocenyl In N,N-dimethyl-formamide at 60℃; for 2.5h;100%
With palladium nanoparticles on graphene; triethylamine In N,N-dimethyl-formamide at 120 - 125℃; for 2h; Heck Reaction;100%
With triethylamine; silica aerogel nanocomposite; palladium In acetonitrile for 8h; Mizoroki-Heck reaction; Heating;99%
Octanethiol
111-88-6

Octanethiol

ethyl acrylate
140-88-5

ethyl acrylate

3-octylsulfanyl-propionic acid ethyl ester
68749-03-1

3-octylsulfanyl-propionic acid ethyl ester

Conditions
ConditionsYield
In acetonitrile electrolysis (0.01-0.1 N Et4NBr or Bu4NBr, Pt cathode, Mg anode);100%
1-(1-diazo-2,2,2-trifluoroethyl)-4-methylbenzene
38512-35-5

1-(1-diazo-2,2,2-trifluoroethyl)-4-methylbenzene

ethyl acrylate
140-88-5

ethyl acrylate

3-carbethoxy-5-trifluoromethyl-5-(p-tolyl)-2-pyrazoline
136603-49-1

3-carbethoxy-5-trifluoromethyl-5-(p-tolyl)-2-pyrazoline

Conditions
ConditionsYield
at 20 - 25℃; for 0.083h;100%
carbon monoxide
201230-82-2

carbon monoxide

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 2-formylpropionate
27772-62-9

ethyl 2-formylpropionate

Conditions
ConditionsYield
With hydrogen; triethylamine; di(rhodium)tetracarbonyl dichloride; 1,4-di(diphenylphosphino)-butane at 25℃; under 15001.2 Torr; for 12h; Product distribution; other ligands: phosphanobornadiene;100%
With hydrogen; triethylamine; di(rhodium)tetracarbonyl dichloride; 1,4-di(diphenylphosphino)-butane at 25℃; under 15001.2 Torr; for 12h;100%
With hydrogen; [Rh(acac)(CO)2]-fluoropolymer ligand In carbon dioxide at 80℃; for 1h;
With hydrogen; C23H22NO5Rh In water; toluene at 85℃; under 30003 Torr; for 8h; Catalytic behavior; Autoclave; chemoselective reaction;
BD 1060
138356-10-2

BD 1060

ethyl acrylate
140-88-5

ethyl acrylate

N-<2-(3,4-dichlorophenyl)-1-ethyl>-N-<1-(ethoxypropionyl)>-2-(1-pyrrolidinyl)ethylamine
141044-90-8

N-<2-(3,4-dichlorophenyl)-1-ethyl>-N-<1-(ethoxypropionyl)>-2-(1-pyrrolidinyl)ethylamine

Conditions
ConditionsYield
In toluene for 72h; Heating;100%
ethyl acrylate
140-88-5

ethyl acrylate

3,4-methylenedioxyphenylacetonitrile
4439-02-5

3,4-methylenedioxyphenylacetonitrile

4-Benzo[1,3]dioxol-5-yl-4-cyano-heptanedioic acid diethyl ester
76934-80-0

4-Benzo[1,3]dioxol-5-yl-4-cyano-heptanedioic acid diethyl ester

Conditions
ConditionsYield
With N-benzyl-trimethylammonium hydroxide In acetonitrile100%
7-Fluoro-5-piperidin-4-ylidene-5,11-dihydro-10-oxa-4-aza-dibenzo[a,d]cycloheptene

7-Fluoro-5-piperidin-4-ylidene-5,11-dihydro-10-oxa-4-aza-dibenzo[a,d]cycloheptene

ethyl acrylate
140-88-5

ethyl acrylate

3-[4-(7-Fluoro-11H-10-oxa-4-aza-dibenzo[a,d]cyclohepten-5-ylidene)-piperidin-1-yl]-propionic acid ethyl ester

3-[4-(7-Fluoro-11H-10-oxa-4-aza-dibenzo[a,d]cyclohepten-5-ylidene)-piperidin-1-yl]-propionic acid ethyl ester

Conditions
ConditionsYield
In ethanol Heating;100%
4-(8-Chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-ylidene)piperidine
126570-60-3

4-(8-Chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-ylidene)piperidine

ethyl acrylate
140-88-5

ethyl acrylate

3-[4-(8-Chloro-11H-10-oxa-4-aza-dibenzo[a,d]cyclohepten-5-ylidene)-piperidin-1-yl]-propionic acid ethyl ester

3-[4-(8-Chloro-11H-10-oxa-4-aza-dibenzo[a,d]cyclohepten-5-ylidene)-piperidin-1-yl]-propionic acid ethyl ester

Conditions
ConditionsYield
In ethanol Heating;100%
5-Piperidin-4-ylidene-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cycloheptene

5-Piperidin-4-ylidene-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cycloheptene

ethyl acrylate
140-88-5

ethyl acrylate

3-[4-(11H-10-Oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene)-piperidin-1-yl]-propionic acid ethyl ester

3-[4-(11H-10-Oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene)-piperidin-1-yl]-propionic acid ethyl ester

Conditions
ConditionsYield
In ethanol Heating;100%
8-Fluoro-5-piperidin-4-ylidene-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cycloheptene
161522-66-3

8-Fluoro-5-piperidin-4-ylidene-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cycloheptene

ethyl acrylate
140-88-5

ethyl acrylate

3-[4-(8-Fluoro-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene)-piperidin-1-yl]-propionic acid ethyl ester

3-[4-(8-Fluoro-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene)-piperidin-1-yl]-propionic acid ethyl ester

Conditions
ConditionsYield
In ethanol Heating;100%
8-Chloro-5-piperidin-4-ylidene-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cycloheptene

8-Chloro-5-piperidin-4-ylidene-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cycloheptene

ethyl acrylate
140-88-5

ethyl acrylate

3-[4-(8-Chloro-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene)-piperidin-1-yl]-propionic acid ethyl ester

3-[4-(8-Chloro-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene)-piperidin-1-yl]-propionic acid ethyl ester

Conditions
ConditionsYield
In ethanol Heating;100%
iodobenzene
591-50-4

iodobenzene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 3,3-diphenylacrylate
17792-17-5

ethyl 3,3-diphenylacrylate

Conditions
ConditionsYield
With silver(I) acetate; palladium diacetate; acetic acid at 110℃; for 6h; Inert atmosphere;100%
With dipalladium(II)(1,1'-di-t-butyl-3,3'-(1,2-ethanediyl)bisimidazolium)dipyridinetetradichloride; tetrabutylammomium bromide; sodium acetate In N,N-dimethyl acetamide at 120℃; for 18h; Heck Reaction; Inert atmosphere;95%
With silver(I) acetate; palladium diacetate; acetic acid at 110℃; for 6h; Heck reaction;94%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In acetonitrile at 140℃; under 7500600 Torr; for 4h;76%

140-88-5Related news

Volumetric Properties of the Ternary System 1,4-Dioxane + Butyl Acrylate + Ethyl acrylate (cas 140-88-5) and Its Binary Butyl Acrylate + Ethyl acrylate (cas 140-88-5) at 298.15 K10/01/2019

Densities of the ternary system 1,4-dioxane + butyl acrylate + ethyl acrylate and its binary butyl acrylate + ethyl acrylate have been measured in the whole composition range, at 298.15 K and atmospheric pressure, using an Anton Paar DMA 5000 oscillating U-tube densimeter. The calculated excess ...detailed

140-88-5Relevant articles and documents

Asymmetric Counter-Anion-Directed Aminomethylation: Synthesis of Chiral β-Amino Acids via Trapping of an Enol Intermediate

Kang, Zhenghui,Wang, Yongheng,Zhang, Dan,Wu, Ruibo,Xu, Xinfang,Hu, Wenhao

, p. 1473 - 1478 (2019)

A novel enantioselective aminomethylation reaction of diazo compound, alcohol and α-aminomethyl ether enabled by asymmetric counteranion-directed catalysis is disclosed that offers an efficient and convenient access to furnish optically active α-hydroxyl-β-amino acids in high yield with high to excellent enantioselectivities. Control experiments and DFT calculations indicate that the transformation proceeds through trapping the in situ generated enol intermediate with methylene iminium ion, and the asymmetric induction was enabled by chiral pentacarboxycyclopentadiene anion via H-bonding and electrostatic interaction.

Homogeneous and Heterogeneous Catalyzed Esterification of Acrylic Acid with Ethanol: Reaction Kinetics and Modeling

Jyoti, Ghoshna,Keshav, Amit,Anandkumar,Bhoi, Stutee

, p. 370 - 380 (2018)

Kinetics of esterification of acrylic acid with ethanol in the presence of homogeneous (H2SO4, HCl, p-TSA, HI) catalysts as well as heterogeneous catalysts (Dowex 50WX, Amberlyst 15) was studied. The effects and performance of these catalysts on the conversion of acrylic acid were evaluated. In the kinetics of homogeneous catalyzed reaction, both concentration and activity-based model were employed. Activity coefficients were predicted by the Universal Functional group Contribution (UNIFAC) method to consider nonideal behavior of the liquid phase. The heterogeneous catalyzed reaction mechanisms were developed using Eley–Rideal theory. The model results were compared with the experimental results and were in good agreement. The temperature dependency of the constants, reaction enthalpy, and entropy, and activation energy were determined. The conversion of acrylic acid was obtained as 63.2%, 61.02%, 53.3%, 21.4%, 34.96%, and 14.84% for H2SO4, p-TSA, HCl, HI, Dowex 50WX, and Amberlyst 15, respectively, under process temperature of 70°C, reactant molar ratio of 1:1, and catalyst concentration of 2% (v/v) for homogeneous and 2.17 g for heterogeneous catalyst. These outcomes provide an approach to understand the significant effect of each catalyst on the esterification kinetics of acrylic acid and ethanol.

Elucidating colorization in the functionalization of hydroxyl-containing polymers using unsaturated anhydrides/acyl chlorides in the presence of triethylamine

Cai, Lei,Wang, Shanfeng

, p. 304 - 307 (2010)

-

Efficient and selective conversion of methyl lactate to acrylic acid using Ca3(PO4)2-Ca2(P2O 7) composite catalysts

Hong, Ju Hyeong,Lee, Jong-Min,Kim, Hyungrok,Hwang, Young Kyu,Chang, Jong-San,Halligudi, Shiva B.,Han, Yo-Han

, p. 194 - 200 (2011)

Calcium phosphate Ca3(PO4)2 and calcium pyrophosphate Ca2(P2O7) composite catalysts of different weight ratios were prepared by a slurry-mixing method. These composite catalysts were calcined at 500 °C in air and characterized by N2 sorption for specific surface area by XRD for crystal phases and by TPD-NH 3 (acidity), TPD-CO2 (basicity) and SEM for morphological features. All the Ca3(PO4)2-Ca 2(P2O7) composite catalysts were found to be active in the vapor phase conversion of methyl lactate (ML) to give mainly acrylic acid (AA) and methyl acrylate (MA) as products. The catalyst Ca 3(PO4)2-Ca2(P2O 7) of 50:50 wt% ratio was the most efficient and selective catalyst in the conversion of ML, which gave 91% conversion of ML with selectivity for AA (75%) and MA (5%) together (80%) under optimized reaction conditions. The higher conversion of ML and formation of AA by Ca3(PO 4)2-Ca2(P2O7) [50:50 wt%] composite catalyst has been attributed to moderate acid-base strength regulated with surface properties.

Controlling the Lewis Acidity and Polymerizing Effectively Prevent Frustrated Lewis Pairs from Deactivation in the Hydrogenation of Terminal Alkynes

Geng, Jiao,Hu, Xingbang,Liu, Qiang,Wu, Youting,Yang, Liu,Yao, Chenfei

, p. 3685 - 3690 (2021/05/31)

Two strategies were reported to prevent the deactivation of Frustrated Lewis pairs (FLPs) in the hydrogenation of terminal alkynes: reducing the Lewis acidity and polymerizing the Lewis acid. A polymeric Lewis acid (P-BPh3) with high stability was designed and synthesized. Excellent conversion (up to 99%) and selectivity can be achieved in the hydrogenation of terminal alkynes catalyzed by P-BPh3. This catalytic system works quite well for different substrates. In addition, the P-BPh3 can be easily recycled.

Acid- And base-switched palladium-catalyzed γ-C(sp3)-H alkylation and alkenylation of neopentylamine

Zhang, Jinquan,Zhang, Shuaizhong,Zou, Hongbin

supporting information, p. 3466 - 3471 (2021/05/31)

The functionalization of remote unactivated C(sp3)-H and the reaction selectivity are among the core pursuits for transition-metal catalytic system development. Herein, we report Pd-catalyzed γ-C(sp3)-H-selective alkylation and alkenylation with removable 7-azaindole as a directing group. Acid and base were found to be the decisive regulators for the selective alkylation and alkenylation, respectively, on the same single substrate under otherwise the same reaction conditions. Various acrylates were compatible for the formation of C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. The alkenylation protocol could be further extended to acrylates with natural product units and α,β-unsaturated ketones. The preliminary synthetic manipulation of the alkylation and alkenylation products demonstrates the potential of this strategy for structurally diverse aliphatic chain extension and functionalization. Mechanistic experimental studies showed that the acidic and basic catalytic transformations shared the same six-membered dimer palladacycle.

Palladium-catalyzed regioselective synthesis of B(4,5)-or B(4)-substituted: O-carboranes containing α,β-unsaturated carbonyls

Li, Jiaoyi,Lu, Jian,Tian, Song,Wang, Qian,Zhang, Chuyi,Zhang, Jianwei,Zhou, Ling

supporting information, p. 4723 - 4727 (2020/07/13)

With the help of a carboxylic acid directing group, Pd-catalyzed regioselective synthesis of B(4,5)-or B(4)-substituted o-carboranes containing α,β-unsaturated carbonyls has been reported. The-COOH, removed during the course of the reaction, is responsible for controlling the regioselectivity. The desired products could be obtained in moderate to good yields.

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