Synthesis of Terminal Alkenes From Internal Alkenes Via Olefin Metathesis
First Claim
1. A method for synthesizing a terminal olefin, the method comprising:
- providing an olefinic substrate having at least one internal olefin;
providing an alpha olefin having at least 3 carbon atoms; and
contacting the olefinic substrate with the alpha olefin in the presence of less than approximately 100 ppm of a metathesis catalyst relative to the number of olefinic substrate double bonds, under reaction conditions effective to allow cross-metathesis to occur;
wherein the contacting yields a product having at least 10 wt % 9DA, and the catalyst has a TON9DA of approximately 10,000 or greater.
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Abstract
This disclosure relates generally to olefin metathesis, and more particularly relates to the synthesis of terminal alkenes from internal alkenes using a cross-metathesis reaction catalyzed by an olefin metathesis catalyst. According to one aspect, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting, in the presence of a ruthenium alkylidene metathesis catalyst, an olefinic substrate comprised of at least one internal olefin with a cross metathesis partner comprised of an alpha olefinic reactant, under reaction conditions effective to allow cross-metathesis to occur, wherein the reaction conditions include a reaction temperature of at least 35° C. The methods, compositions, reactions and reaction systems herein disclosed have utility in the fields of catalysis, organic synthesis, and industrial chemistry.
213 Citations
69 Claims
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1. A method for synthesizing a terminal olefin, the method comprising:
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providing an olefinic substrate having at least one internal olefin; providing an alpha olefin having at least 3 carbon atoms; and contacting the olefinic substrate with the alpha olefin in the presence of less than approximately 100 ppm of a metathesis catalyst relative to the number of olefinic substrate double bonds, under reaction conditions effective to allow cross-metathesis to occur; wherein the contacting yields a product having at least 10 wt % 9DA, and the catalyst has a TON9DA of approximately 10,000 or greater. - View Dependent Claims (2, 4, 6, 7, 9, 10, 11, 12, 13, 14, 17, 19, 21, 33, 63, 64, 65, 66)
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41. A method for synthesizing a terminal olefin, the method comprising:
- contacting, under an inert or oxygen atmosphere and in the presence of a ruthenium alkylidene metathesis catalyst, an olefinic substrate comprised of at least one internal olefin with a cross metathesis partner comprised of an alpha olefin having at least 3 carbon atoms, under reaction conditions effective to ensure that the olefinic substrate and the cross-metathesis partner are in liquid form and to allow cross-metathesis to occur, wherein the catalyst is present in an amount ranging from about 1 ppm to about 100 ppm relative to the number of olefinic substrate double bonds.
- View Dependent Claims (61, 62)
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67. A method for synthesizing a terminal olefin, the method comprising:
- contacting, in the presence of a ruthenium alkylidene metathesis catalyst, an olefinic substrate comprised of at least one internal olefin with an alpha olefin having at least 3 carbon atoms, under reaction conditions effective to allow cross-metathesis to occur, wherein the ruthenium alkylidene metathesis catalyst has the structure of formula (IV);
- View Dependent Claims (68, 69)
- contacting, in the presence of a ruthenium alkylidene metathesis catalyst, an olefinic substrate comprised of at least one internal olefin with an alpha olefin having at least 3 carbon atoms, under reaction conditions effective to allow cross-metathesis to occur, wherein the ruthenium alkylidene metathesis catalyst has the structure of formula (IV);
Specification