105-38-4

Basic information

• Product Name: Vinyl propionate
• Synonyms: Propionicacid, vinyl ester (6CI,8CI); NSC 5275; Vinyl propanoate; Vinyl propionate
• CAS NO: 105-38-4
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.13
• EINECS: 203-293-5
• Mol File: 105-38-4.mol

Chemical Properties

• Boiling Point: 94-95°C(lit.)
• Flash Point: 43°F
• Appearance: /
• Density: 0.919g/mLat 25°C(lit.)
• Vapor Pressure: 50.4mmHg at 25°C
• Refractive Index: 1.402
• CAS DataBase Reference: Vinyl propionate(CAS DataBase Reference)
• NIST Chemistry Reference: Vinyl propionate(105-38-4)
• EPA Substance Registry System: Vinyl propionate(105-38-4)

Safety Data

• Statements: R11:Highly flammable.
• Safety Statements: S16:Keep away from sources of ignition - No smoking.; S23:Do not inhale gas/fumes/vapour/spray.; S33:Take precauti
• Hazardous Substances Data: 105-38-4(Hazardous Substances Data)

Usage

Uses

Used in Polymer and Resin Production:
Vinyl propionate is used as a monomer for the production of various polymers and resins, primarily due to its ability to enhance the properties of these materials. It contributes to the creation of adhesives and coatings, improving their adhesive strength and durability.
Used in Chemical Synthesis:
In the chemical industry, vinyl propionate is utilized as a chemical intermediate, playing a crucial role in the synthesis of other compounds. Its reactivity and functional groups make it a valuable component in the development of new chemical products.
Used in Adhesive and Coating Manufacturing:
Vinyl propionate is used as a key ingredient in the manufacturing of adhesives and coatings, where it imparts specific characteristics such as improved bonding and resistance to environmental factors. Its incorporation into these products enhances their performance and extends their applications across various industries.

InChI:InChI=1/C5H8O2/c1-3-5(6)7-4-2/h4H,2-3H2,1H3

Synthetic route

bis(formylmethyl)mercury (4387-13-7) + propionyl chloride (79-03-8) → vinyl propionate (105-38-4)

Conditions	Yield
In tetrahydrofuran Heating;	90%

vinyl acetate (108-05-4) + propionic acid (802294-64-0) → vinyl propionate (105-38-4)

Conditions	Yield
With sulfuric acid; mercury(II) diacetate; copper (I) acetate at 20℃; for 2h; 30 deg C, 72 h;	30%
With [fac-Ru(CO)3(η2-CH3CH2COO)(η1-CH3CH2COO)] at 100℃; Kinetics; Reagent/catalyst;
With sulfuric acid; mercury(II) diacetate

propionic acid (802294-64-0) + acetylene (74-86-2) → vinyl propionate (105-38-4)

Conditions	Yield
With copper(I) monacetylide at 200℃; under 8826.09 Torr;
With zinc(II) propionate; pyrographite at 250℃;
With mercury(II) sulfate at 95 - 105℃;
With mercury salt-boron fluoride at 27 - 30℃;
With mercury salt-boron fluoride at 27 - 30℃;

2-acetoxyethyl propionate → vinyl acetate (108-05-4) + vinyl propionate (105-38-4)

Conditions	Yield
With methanolate In gas
With methanolate In gas Product distribution; also with base F(1-);

ethylene glycol dipropionate → vinyl propionate (105-38-4)

Conditions	Yield
at 550 - 560℃; Pyrolysis;

vinyl acetate (108-05-4) → vinyl propionate (105-38-4)

Conditions	Yield
With propionic acid; tin(IV) chloride

ethene (74-85-1) + propionic acid (802294-64-0) + benzene (71-43-2) → styrene (292638-84-7) + (E)-1,2-diphenyl-ethene (103-30-0) + vinyl propionate (105-38-4) + phenol (108-95-2)

Conditions	Yield
With air; 1,3-diphenylpropanedione; palladium diacetate at 90℃; under 1900.13 Torr; for 8h; Product distribution; Further Variations:; Pressures; Reagents; Solvents; Temperatures; ethylene/air ratio;	A 0.213 mmol B 0.043 mmol C 0.038 mmol D 0.030 mmol

Upstream product

• 802294-64-0 propionic acid 
• 74-86-2 acetylene 
• 9004-34-6 cellulose 
• 74-85-1 ethene 
• 71-43-2 benzene 
• 108-05-4 vinyl acetate 
• 4387-13-7 bis(formylmethyl)mercury 
• 79-03-8 propionyl chloride 

Downstream Products

• 53075-94-8 2-(ethoxycarbonyl)ethyl phenyl sulfoxide 
• 116809-20-2 propionic acid-((S)-1-methyl-2-phenyl-ethyl ester) 
• 116809-20-2 Propionic acid (R)-1-methyl-2-phenyl-ethyl ester 
• 1266334-64-8 (R)-2-hydroxymethyl-5-phenylpentyl propanoate 
• 1266334-68-2 5-phenyl-2-propanoyloxymethylpentyl propanoate 
• 1247075-54-2 C₁₁H₉Cl₂NO₂ 
• 1152090-21-5 C₁₄H₁₈O₄ 
• 105-90-8 geranyl propionate 
• 81176-43-4 (S)-trans-4-phenyl-3-buten-2-ol 
• 10420-89-0 (S)-1-(1-Naphthyl)ethylamine 
• 116837-58-2 N-[(R)-1-(naphthalen-1-yl)ethyl]propanamide 
• 6283-04-1 N-phenethylpropionamide 

Related news

Polymer paperEmulsion polymerization of Vinyl propionate (cas 105-38-4) using a newly developed redox pair initiation system08/18/2019

The kinetics of emulsion polymerization of vinyl propionate (VP) using the redox system potassium persulfate (KPS)/acetone-sodium bisulfite (ASBS) as redox pair initiation system is studied at 25°C. The effect of different initiator concentrations on the rate of polymerization and on the number...detailed

Gas phase kinetics for the ozonolysis of n-butyl methacrylate, ethyl crotonate and Vinyl propionate (cas 105-38-4) under atmospheric conditions08/15/2019

Rate coefficients for the reactions of ozone with n-butyl methacrylate, ethyl crotonate and vinyl propionate have been determined at 298 ± 1 K and atmospheric pressure. The following room temperature rate coefficients (in cm3 molecule−1 s−1 units) were obtained: k1(O3 + CH2C(CH3)C(O)OC4H9) = (1...detailed

Atmospheric photodegradation of ethyl vinyl ketone and Vinyl propionate (cas 105-38-4) initiated by OH radicals08/13/2019

Rate coefficients for the reactions of hydroxyl radicals with ethyl vinyl ketone and vinyl propionate were determined at 298 K and atmospheric pressure. A collapsible chamber with gas chromatography was used to perform relative kinetic determinations. The room temperature rate coefficients (in c...detailed

Relevant articles and documents

A novel synthesis of vinyl esters from vinylversatate-10

Vinylversatate-10 (VV10)1 1 VV 10 Vinyl Monomer, Development Product, Shell Chemical Company has successfully been used to synthesise a large number of lower vinyl esters by transvinylation in presence of mercuric acetate and sulfuric acid. The synthesis of vinylhalo esters proceeds with more difficulty. It has been observed that neither Hg(OAc)2 nor H2SO4 alone is capable of initiating the transvinylation. Furthermore, it has been found that a molar ratio 2:1 of VV10 to carboxylic acid is sufficient to drive the reaction to the right by continuous distillation of the vinyl ester formed, and as a result a high yield of vinyl ester is obtained. A mechanism for this reaction and for the formation of side products has been proposed.

Catalytic pyrolysis of cellulose in ionic liquid [bmim]OTf

This study discussed the catalytic cracking process of cellulose in ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate ([bmim]OTF) under 180 °C, 240 °C and 340 °C, found that [bmim]OTF is an effective catalyst which can effectively reduce the pyrolysis temperature(nearly 200 °C) of the cellulose. FRIR, XRD and SEM were used to analyze the structure characterization of fiber before and after the cracking; GC-MS was used for liquid phase products analysis; GC was used to analyze gas phase products. The results showed that the cellulose pyrolysis in [bmim]OTf mainly generated CO2, CO and H2, also generated 2-furfuryl alcohol, 2,5-dimethyl-1,5-diallyl-3-alcohol, 1,4-butyrolactone, 5-methyl furfural, 4-hydroxy butyric acid, vinyl propionate, 1-acetoxyl group-2-butanone, furan formate tetrahydrofuran methyl ester liquid product, and thus simulated the evolution mechanism of cellulose pyrolysis products based on the basic model of cellulose monomer.

Ruthenium-catalyzed transvinylation - New insights

The use of ruthenium complexes in transvinylation catalysis has been well established since the 1980s. However, the reaction mechanism and the active catalyst species, which is presumed to contain ruthenium carbonyl carboxylate entities, have so far remained elusive. In this work the synthesis and characterization of three novel ruthenium complexes comprising ruthenium carbonyl carboxylate structural motifs including two single crystal structures as well as the crystal structures of two known ruthenium complexes are reported. These new complexes and four known ruthenium complexes with appropriate structural motifs were applied in transvinylation catalysis. Mechanistic studies including identification and characterization of the active species, isotope labeling experiments and examination of the regioand stereoselectivity of the transvinylation reaction are presented, resulting in the proposal of a probable reaction mechanism, which is supported by DFT calculations on the B3LYP/6-31G* level of theory.

Oxidative arylation of ethylene with benzene catalyzed by Pd(OAc) 2/heteropoly acid/O2 system

Oxidative arylation of ethylene with benzene was examined by using a Pd(OAc)2/heteropoly acid/O2 system under mild conditions. The reaction of benzene with ethylene in the presence of catalytic amounts of Pd(OAc)2 combined

Competitive reactivity as a probe for reaction coordinates in gas-phase ion-molecule chemistry

Using the method of competitive reactivity of two functional groups in the same molecule, anionic elimination reactions show considerable kinetic selectivity for small differences in leaving group thermochemistry, in structures of the general type YCH2CH2CH2Z, where Y and Z are good anionic leaving groups.

Poly(vinyl propionate) and Poly(ethyl acrylate) - A Miscible Polymer Pair

A new miscible polymer pair, viz. poly(vinyl propionate) (PVPr) and poly(ethyl acrylate) (PEA) is reported.Blends of these polymers form clear films, clear solutions in common solvents and have single glass transition temperatures.Miscibility of these two polymers in binary combinations with poly(methyl acrylate) (PMA) or poly(vinyl acetate) PVA was also examined.Differential scanning calorimetry (D.S.C.) reveals that PVPr + PVA, PEA + PVA, PMA + PVPr and PMA + PEA are immiscible, although the first three pairs form clear films.

Method for the preparation of alkenyl esters of carboxylic acids

A novel and effective catalyst system is provided for application in the preparation of alkenyl esters of carboxylic acids by transesterification reaction. The catalyst system consists of a palladium compound as the main ingredient and a cocatalyst formed of an alkali metal compound and a copper compound, at least one of which is a halide. The catalyst ingredients are adsorbed on a solid catalyst carrier, so that repeated use of the combined catalyst or a continuous operation of the reaction can easily be facilitated.

Acyl Transfer Reactions in the Gas Phase. Ion-Molecule Chemistry of Vinyl Acetate

An ion cyclotron resonance study of the ion-molecule reactions of vinyl acetate with methanol in the gas phase has revealed the formation of structurally different ions having the composition of protonated vinyl acetate.Deuterium-labeled reactants (CD3CO2CH=CH2 with CH3OH or CD3OD) gave product ions showing incorporation of up to two deuteriums in the vinyl group, indicating coexistence and interconversion of O-protonated and C-protonated vinyl acetate.Evidence was also obtained for a third MH+ ion for which the proposed structure is protonated 3-oxobutanal.This ion is believed to be formed by attack of CH3CO+ at the terminal vinylic carbon with loss of the ester acyl group as ketene.The ion reacts with methanol to give m/z 101 by loss of water.In contrast, protonated vinyl acetate reacts with methanol by an acyl transfer process to give (AcOCH3)H+, m/z 75.The related ion chemistry of vinyl propanoate, vinyl 2,2-dimethylpropanoate, and isopropenyl acetate is also described.Each of the acyl transfer reactions observed is consistent with formation of intermediate acylium ion complexes rather than tetracovalent addition complexes.Attempts were made to generate tetracovalent intermediates by an independent route from ortho esters of vinyl acetate.Dissociation of the ortho ester CH3C(OCH=CH2)2(OCH3) to dioxacarbocations was the dominant reaction, but the product ions were unreactive with H2O, CH3OH, or t-C4H9OH.The mechanistic implications of these results are discussed.

Transesterification of carboxylic acids

Carboxylic acids may be esterified by reaction with esters in the presence of a catalytic amount of a tin halide catalyst, the reaction being effected at temperatures ranging from about 0° to about 150° C.