A process for the reactivation of an acidic ion exchange resin is described. The invention relates to the treatment of an at least partially deactivated resin which has been deactivated by contact with an impure ethylenically unsaturated acid or ester containing target impurities. The reactivation includes the step of contacting the at least partially deactivated resin with an alcohol to thereby increase the activity thereof. The invention extends to reactivating a resin deactivated by contact with an impure ethylenically unsaturated acid, ester or nitrile containing target impurities by contacting the at least partially deactivated resin with an alcohol and a carboxylic acid to thereby increase the activity thereof. A reactivated resin and a process for preparing and purifying an ethylenically unsaturated acid or ester of the following formula:
R.sup.1—C(═(CH.sub.2).sub.m)—COOR.sup.2
are also described.

A process for the reactivation of an acidic ion exchange resin is described. The invention relates to the treatment of an at least partially deactivated resin which has been deactivated by contact with an impure ethylenically unsaturated acid or ester containing target impurities. The reactivation includes the step of contacting the at least partially deactivated resin with an alcohol to thereby increase the activity thereof. The invention extends to reactivating a resin deactivated by contact with an impure ethylenically unsaturated acid, ester or nitrile containing target impurities by contacting the at least partially deactivated resin with an alcohol and a carboxylic acid to thereby increase the activity thereof. A reactivated resin and a process for preparing and purifying an ethylenically unsaturated acid or ester of the following formula:
R.sup.1—C(═(CH.sub.2).sub.m)—COOR.sup.2
are also described.

A process for the reactivation of an acidic ion exchange resin is described. The invention relates to the treatment of an at least partially deactivated resin which has been deactivated by contact with an impure ethylenically unsaturated acid or ester containing target impurities. The reactivation includes the step of contacting the at least partially deactivated resin with an alcohol to thereby increase the activity thereof. The invention extends to reactivating a resin deactivated by contact with an impure ethylenically unsaturated acid, ester or nitrile containing target impurities by contacting the at least partially deactivated resin with an alcohol and a carboxylic acid to thereby increase the activity thereof. A reactivated resin and a process for preparing and purifying an ethylenically unsaturated acid or ester of the following formula:
R.sup.1—C(═(CH.sub.2).sub.m)—COOR.sup.2
are also described.

A method for producing a fatty acid ester through desulfurization of sulfur from a fatty acid ester using a catalyst, wherein the catalyst carries a catalyst metal on a support, (a) the catalyst contains as the catalyst metal one or more elements selected from the elements of group 9, group 10 and group 11 of the periodic table, (b) the total pore volume of the catalyst is 0.05 mL/g or more, and (c) the volume of pores with a pore size of 0.1 μm or more and 500 μm or less is 50% or more of the total pore volume of the catalyst. A desulfurization method using the desulfurization and a method for producing an alcohol through hydrogenation of the fatty acid ester obtained through the desulfurization are also provided.

A method for producing a fatty acid ester through desulfurization of sulfur from a fatty acid ester using a catalyst, wherein the catalyst carries a catalyst metal on a support, (a) the catalyst contains as the catalyst metal one or more elements selected from the elements of group 9, group 10 and group 11 of the periodic table, (b) the total pore volume of the catalyst is 0.05 mL/g or more, and (c) the volume of pores with a pore size of 0.1 μm or more and 500 μm or less is 50% or more of the total pore volume of the catalyst. A desulfurization method using the desulfurization and a method for producing an alcohol through hydrogenation of the fatty acid ester obtained through the desulfurization are also provided.

A method for producing a fatty acid ester through desulfurization of sulfur from a fatty acid ester using a catalyst, wherein the catalyst carries a catalyst metal on a support, (a) the catalyst contains as the catalyst metal one or more elements selected from the elements of group 9, group 10 and group 11 of the periodic table, (b) the total pore volume of the catalyst is 0.05 mL/g or more, and (c) the volume of pores with a pore size of 0.1 μm or more and 500 μm or less is 50% or more of the total pore volume of the catalyst. A desulfurization method using the desulfurization and a method for producing an alcohol through hydrogenation of the fatty acid ester obtained through the desulfurization are also provided.

The present invention relates to a process for preparing a (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (S,R)-(2), wherein R.sup.1 represents a monovalent hydrocarbon group having 1 to 6 carbon atoms, and a bold wedged bond represents the absolute configuration, and a (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (R,S)-(3), wherein R.sup.1 is as defined above, a hashed wedged bond represents the absolute configuration, and Ac represents an acetyl group, the process comprising: subjecting a (1RS,2SR)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (RS,SR)-(2), wherein R.sup.1 is as defined above, and a hashed unwedged bond represents a relative configuration, to a kinetic resolution reaction with a lipase in the presence of vinyl acetate to obtain the (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((S,R)-(2)) and the (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((R,S)-(3)).

##STR00001##

The present invention relates to a process for preparing a (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (S,R)-(2), wherein R.sup.1 represents a monovalent hydrocarbon group having 1 to 6 carbon atoms, and a bold wedged bond represents the absolute configuration, and a (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (R,S)-(3), wherein R.sup.1 is as defined above, a hashed wedged bond represents the absolute configuration, and Ac represents an acetyl group, the process comprising: subjecting a (1RS,2SR)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (RS,SR)-(2), wherein R.sup.1 is as defined above, and a hashed unwedged bond represents a relative configuration, to a kinetic resolution reaction with a lipase in the presence of vinyl acetate to obtain the (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((S,R)-(2)) and the (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((R,S)-(3)).

##STR00001##

This invention outlines a method for synthesizing a blended resin system in a one pot reaction that may utilize, for example, bio-based anhydrosugars such as isosorbide as a principle component to produce isosorbide dimethacrylate and other monomeric materials for thermosetting applications. This invention establishes a one-pot procedure for reacting a hydroxy group containing compound with methacrylic anhydride in the first step and using the by-product methacrylic acid to react with glycidyl ethers to form additional methacrylate compounds in the second step. This methodology can be formulated to produce a wide array of resin systems that have controlled ratios of hydroxy group containing compound/crosslinker/reactive diluent. Additionally, the novel resin systems may be partially to fully biobased, promoting global sustainability and reducing costs, and when free radically polymerized have properties that meet or exceed their petroleum derived counterparts.

A neutralization/water separation device for an esterified product including: a neutralization tank in which a crude product mixture containing alcohol and an ester compound, a neutralizing agent, and water are put to produce a neutralized mixture; a water separation tank disposed below the neutralization tank to divide the neutralization mixture into a floating layer and an aqueous layer; a partition wall extending downward from a ceiling of the water separation tank to provide a lower passage in the water separation tank; and a transfer line that transfers the neutralized mixture from the neutralization tank to the water separation tank, where the water separation tank includes: a first water separation part into which the neutralized mixture is introduced from the neutralization tank through the transfer line; and a second water separation part into which the neutralized mixture is introduced from the first water separation part through the lower passage, where the first water separation part and the second water separation part are partitioned by the partition wall.