 Process and catalyst for olefin polymerization |
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Hydrocyanation of olefinic alkyl esters
| Details |
Inventors: Pesa, Frederick A.; Graham, Anne M.;
Assignee: The Standard Oil Company (Cleveland, OH)
Primary Examiner: Brust; Joseph Paul
Assistant Examiner:
Attorney, Agent or Firm: Pace; Salvatore P., Knudsen; Herbert D., Evans; Larry W.
Cyanoesters are prepared by contacting an olefinic carboxylate ester, e.g. methyl acrylate, with gaseous hydrogen cyanide in the presence of a catalyst containing an element selected from the group consisting of Group IA metals and Group IIA metals. |
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DETAILED DESCRIPTION OF THE INVENTION According to the present invention, cyanoesters are produced by the catalytic addition of hydrogen cyanide to carboxylate esters.
The overall reaction taking place in this process is represented by the following equation.
##STR1## wherein R.
sub.
1, R.
sub.
2, R.
sub.
3 and X are defined below.
Nitriles, such as cyanoesters are well known organic chemicals having a wide variety of uses as solvents and the like.
They are also important intermediates for the preparation of a broad spectrum of organic chemicals as described, for example in the text "The Chemistry of Organic Cyanogen Compounds" by V.
Migridichian, American Chemical Society Monograph No.
105, Reinhold Publishing Company (New York, 1947).
Reactants The activated olefin reactants which are employed in the process of the present invention are carboxylate esters which have one olefinic moiety, do not contain an acetylinic moiety or groups which would interfere with the hydrocyanation process, and may be represented by the general formula: ##STR2## wherein R.
sub.
1, R.
sub.
1 and R.
sub.
3 are each independently selected from the group consisting of: (1) hydrogen; (2) C.
sub.
1-4 alkyl; ##STR3## wherein R.
sub.
4 is hydrogen or a C.
sub.
1-4 alkyl and n is 0 to 4; and ##STR4## wherein R.
sub.
5 is hydrogen or a C.
sub.
1-4 alkyl and s is 0 to 4; and wherein X is represented by the formula ##STR5## wherein R.
sub.
6 is a C.
sub.
1-12 alkyl and t is 0 to 2.
Examples of carboxylate esters suitable as reactants in the process of the present invention include but are not limited to methyl acrylate, ethyl acrylate, higher alkyl acrylates, methylmethacrylate, ethyl methacrylate, ethyl crotonate and the like.
Preferably, R.
sub.
1, R.
sub.
2 and R.
sub.
3 are each independently selected from: (1) hydrogen; (2) C.
sub.
1-4 alkyl; and X is represented by the formula: ##STR6## wherein R.
sub.
6 is a C.
sub.
1-4 alkyl.
The activated olefin, that is the olefinic ester, is contacted in the vapor phase with gaseous hydrogen cyanide to produce the cyanoester
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Molecular Biology 
