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US 9,416,091 B1Granted
Catalytic transesterification of ester compounds with groups reactive under transesterification conditions
AssigneeSirrus, Inc.
InventorsJeffrey M. Sullivan, Aniruddha Sudhir Palsule, Peter Rulon Stevenson, Kshitij Kishen Parab
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Abstract
Disclosed are methods for the catalytic transesterification of compounds having one or more ester groups and groups reactive under transesterification conditions, such as 1,1-disubstituted alkene compounds, with alcohols or esters and novel compositions prepared therefrom. Further disclosed are novel compounds and compositions prepared as a result of the methods.
Claims22
A method comprising:
- contacting a first ester compound having one or more ester groups with hydrocarbyl moieties as part of each of the ester groups and a functional group which may undergo undesired side reactions under transesterification reaction conditions, with one or more alcohols having a hydrocarbon backbone and one or more hydroxyl groups or one or more second ester compounds having one or more ester groups with hydrocarbyl moieties different from the hydrocarbyl moieties on the first ester compounds, in the presence of one or more acids having a pKa in a polar aprotic solvent of about −5 to about 14 or esters of the acid under conditions that at least one of the hydrocarbyl moieties on the first ester compound is replaced by the alcohol hydrocarbon backbone or hydrocarbyl moieties from the second ester compounds;
- wherein the alcohols comprise a mixture of alcohols or the second ester compounds comprise a mixture of ester compounds.
A method comprising:
- contacting a first ester compound having one or more ester groups with hydrocarbyl moieties as part of each of the ester groups and a functional group which may undergo undesired side reactions under transesterification reaction conditions, with one or more alcohols having a hydrocarbon backbone and one or more hydroxyl groups or one or more second ester compounds having one or more ester groups with hydrocarbyl moieties different from the hydrocarbyl moieties on the first ester compounds, in the presence of one or more acids having a pKa in a polar aprotic solvent of about −5 to about 14 or esters of the acid under conditions that at least one of the hydrocarbyl moieties on the first ester compound is replaced by the alcohol hydrocarbon backbone or hydrocarbyl moieties from the second ester compounds;
- wherein the method is performed at a temperature of about 50° C. to about 160° C.
A method comprising:
- contacting a first ester compound having one or more ester groups with hydrocarbyl moieties as part of each of the ester groups and a functional group which may undergo undesired side reactions under transesterification reaction conditions, with one or more alcohols having a hydrocarbon backbone and one or more hydroxyl groups or one or more second ester compounds having one or more ester groups with hydrocarbyl moieties different from the hydrocarbyl moieties on the first ester compounds, in the presence of one or more acids having a pKa in a polar aprotic solvent of about −5 to about 14 or esters of the acid under conditions that at least one of the hydrocarbyl moieties on the first ester compound is replaced by the alcohol hydrocarbon backbone or hydrocarbyl moieties from the second ester compounds;
- wherein the one or more second compounds having one or more ester moieties is an acetate ester or a formate ester.
A method comprising:
- contacting a first ester compound having one or more ester groups with hydrocarbyl moieties as part of each of the ester groups and a functional group which may undergo undesired side reactions under transesterification reaction conditions, with one or more alcohols having a hydrocarbon backbone and one or more hydroxyl groups or one or more second ester compounds having one or more ester groups with hydrocarbyl moieties different from the hydrocarbyl moieties on the first ester compounds, in the presence of one or more acids having a pKa in a polar aprotic solvent of about −5 to about 14 or esters of the acid under conditions that at least one of the hydrocarbyl moieties on the first ester compound is replaced by the alcohol hydrocarbon backbone or hydrocarbyl moieties from the second ester compounds:
- wherein the first ester compound is one or more 1,1-disubstituted alkene compounds which are contacted with one or more alcohols having two or more hydroxyl groups or one or more second ester compounds having two or more ester groups wherein the resulting product contains the core unit of two or more 1,1-disubstituted alkene compounds linked by the hydrocarbon backbone of the alcohols or the second ester compounds.
A composition comprising a 1,1-disubstituted alkenes bonded to through an oxygen bond to the alkyl group which is further bonded to a hydroxyl alkyl acrylate which is illustrated by the formula:
- wherein:
- R1 is separately in each occurrence hydrocarbyl groups;
- R is separately in each occurrence a hydrocarbyl group substituted with a functional group which may undergo undesired side reactions under transesterification reaction conditions;
- R6 is the residue of an alkyl acrylate;
- c is separately in each occurrence an integer of 3 or more;
- d is separately in each occurrence an integer of 2 or more and is less than c.
3 more elements
Dependencies are inferred from the claim text.