94-04-2

Usage

Uses

Polymers, emulsion paints.

InChI:InChI=1/C10H18O2/c1-4-7-8-9(5-2)10(11)12-6-3/h6,9H,3-5,7-8H2,1-2H3

Upstream product

• 149-57-5 2-Ethylhexanoic acid 
• 74-86-2 acetylene 
• 74-85-1 ethene 
• 108-05-4 vinyl acetate 

Downstream Products

• 151476-58-3 2-Ethyl-hexanoic acid 2-azido-1-phenylselanyl-ethyl ester 
• 151476-83-4 2-(1-Ethyl-pentyl)-5-phenylselanyl-4,5-dihydro-oxazole 

Relevant academic research and scientific papers

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

The present invention relates to a continuous, catalytic process for preparing a vinyl ester of the formula R—C(O)O—CH═CH2 by reaction of a carboxylic acid of the formula R—C(O)OH with a transvinylating reagent of the formula R1—C(O)O—CH═CH2, wherein the reaction is effected at a temperature of 90 to 160° C. and at a pressure of 0.5 to 15 MPa without withdrawal of a reactant in the presence of a transition metal catalyst containing at least one transition metal from the group of ruthenium, osmium, rhodium, iridium, palladium and platinum, and then the resulting reaction mixture is separated into its constituents.

Transvinylation as a First Stage of Coupling Production of Vinyl Esters and Acetic Acid or Propionic Acid Reaction Products

Process for coproduction of a vinyl ester of the formula R—C(O)O—CH═CH by transvinylation reaction of a carboxylic acid of the formula R—C(O)OH with a transvinylating reagent of the formula R1—C(O)O CH═CH2, characterized in that (a) the transvinylation reaction is conducted continuously at a temperature of 90 to 160° C. and at a pressure of 0.5 to 15 MPa without withdrawal of a reactant in the presence of a transition meta/catalyst containing at least one transition metal selected from the group of ruthenium, osmium, rhodium, iridium, palladium and platinum; (b) the resulting reaction mixture is separated into its constituents and the vinyl ester of the formula R—C(O)O—CH═CH2 and the carboxylic acid of the formula R1—C(O)—OH are removed; and (c) the carboxylic acid obtained after step (b) is converted to a derivative of the formula R1—C(O)—X, R1—CH2—OH or R6—C(O)—OH in which X is vinyloxy, O—CH—CH2, halogen, alkoxy of the formula OR2 in which R2 is a substituted or unsubstituted hydrocarbyl radical having 1 to 10 carbon atoms, amino of the formula NR3R4 in which R3 and R4 are each independently hydrogen or a substituted or unsubstituted hydrocarbyl radical having 1 to 10 carbon atoms, or carboxyl of the formula O—C(O)—R5 in which R5 is hydrogen or a substituted or unsubstituted hydrocarbyl radical having 1 to 10 carbon atoms, and R6 is the partly or fully halogen-substituted R1 radical.

Process for the semi-continuous transvinylation of carboxylic acids with vinyl acetate

A semi-continuous process is provided for selective formation of a vinyl ester by reactive distillation from a corresponding carboxylic acid. Carboxylic acid, vinyl acetate, and a palladium acetate—bidentate ligand catalyst complex are provided and reacted in a typical embodiment. Acetic acid and vinyl acetate are continuously removed from the reaction mixture and vinyl acetate is recycled to the reaction mixture. The vinyl ester product is separated from the vinyl acetate, residual carboxylic acid, residual acetic acid, and catalyst.

VINYL ESTER PRODUCTION FROM ACETYLENE AND CARBOXYLIC ACID UTILIZING HETEROGENEOUS CATALYST

A process for the selective production of vinyl ester by the reaction of a carboxylic acid with acetylene under heterogeneous catalytic conditions is disclosed and claimed. In a preferred embodiment of this invention, reaction of benzoic acid and acetylene in the presence of supported platinum catalyst at a temperature of from about 100 to 180°C results in quantitative yields of vinyl benzoate.

VINYL ESTER PRODUCTION FROM ACETYLENE AND CARBOXYLIC UTILIZING HOMOGENEOUS CATALYST

A process for the selective production of vinyl ester by the reaction of a carboxylic acid with acetylene with a homogeneous catalyst is disclosed and claimed. In a preferred embodiment of this invention, reaction of benzoic acid and acetylene in the presence of Group VIII metal complex catalyst at a temperature of about 50 to 1800C results in quantitative yields of vinyl benzoate.

Synthesis of enol and vinyl esters catalyzed by an iridium complex

Enol and vinyl esters were successfully synthesized by the use of an iridium complex as a catalyst. The reaction of carboxylic acid with terminal alkynes in the presence of catalytic amounts of [Ir(cod)Cl]2 and Na2CO3 gave the corresponding 1-alkenyl esters. The addition of carboxylic acids to alkynes principally took place in the Markovnikov fashion. In addition, by the use of an Ir complex combined with NaOAc various vinyl esters were prepared through the transvinylation between carboxylic acids and vinyl acetate.

A simple route to acylsilane enol esters from enol esters

A new methodology is described for the synthesis of enol esters of acylsilanes, from readily available vinyl esters. A solution of LDA is added to a mixture of an enol ester (preferably sterically congested, with only one α- carboxyl proton, eg 2-ethylhexanoate) and a chlorosilane at -78°C to afford the product.