The invention provides a method for producing an epoxy compound by hydrogen peroxide using an organic compound having a carbon-carbon double bond as a raw material, wherein a by-product is suppressed from being generated and the epoxy compound is produced in a high yield. In particular, the invention provides a method for producing an epoxy compound involving oxidizing a carbon-carbon double bond in an organic compound with hydrogen peroxide in the presence of a catalyst, wherein the catalyst comprises a tungsten compound; a phosphoric acid, a phosphonic acid or salts thereof; and an onium salt having an alkyl sulfate ion represented by formula (I) as an anion: ##STR00001##
wherein R.sup.1 is a linear or branched aliphatic hydrocarbon group having 1 to 18 carbons, which may be substituted with 1 to 3 phenyl groups.

The invention provides a method for producing an epoxy compound by hydrogen peroxide using an organic compound having a carbon-carbon double bond as a raw material, wherein a by-product is suppressed from being generated and the epoxy compound is produced in a high yield. In particular, the invention provides a method for producing an epoxy compound involving oxidizing a carbon-carbon double bond in an organic compound with hydrogen peroxide in the presence of a catalyst, wherein the catalyst comprises a tungsten compound; a phosphoric acid, a phosphonic acid or salts thereof; and an onium salt having an alkyl sulfate ion represented by formula (I) as an anion: ##STR00001##
wherein R.sup.1 is a linear or branched aliphatic hydrocarbon group having 1 to 18 carbons, which may be substituted with 1 to 3 phenyl groups.

Provided is a method for producing an optically active substance, the method including an asymmetric induction, wherein an asymmetry inducer is allowed to act on a chiral molecule having a half-life of enantiomeric excess of shorter than 10 hours, thereby increasing abundance of one enantiomer of the chiral molecule. According to this method, one enantiomer of a chiral molecule that is susceptible to racemization can be selectively and efficiently obtained.

Methods for the synthesis of methyl 2-fluoroacrylate (MFA) are provided. The methods include use of various hydrofluorination agents using a variety of starting materials and reaction schemes. The methyl 2-fluoroacrylate prepared by the methods described herein can further be used to prepare patiromer calcium sorbitex.

A process for making propene oxide involves reacting propene with hydrogen peroxide in the presence of methanol, a titanium zeolite epoxidation catalyst, and nitrogen containing compounds present in an amount of from 100 to 3000 mg/kg of hydrogen peroxide. Non-reacted propene is separated from the reaction mixture; the propene depleted reaction mixture Is continuously distilled in a distillation column providing an overhead product stream containing propene oxide and methanol and a bottoms product stream; and propene oxide is separated from the overhead product stream. An acid is added to the propane depleted reaction mixture and/or to the distillation column at the same level or above the feed point for the propene depleted reaction mixture and/or contacted to the feed to the distillation column to provide an apparent pH in the bottoms product stream of from 3 to 4.5, which reduces the nitrogen content of the separated propene oxide.

A process for making propene oxide involves reacting propene with hydrogen peroxide in the presence of methanol, a titanium zeolite epoxidation catalyst, and nitrogen containing compounds present in an amount of from 100 to 3000 mg/kg of hydrogen peroxide. Non-reacted propene is separated from the reaction mixture; the propene depleted reaction mixture Is continuously distilled in a distillation column providing an overhead product stream containing propene oxide and methanol and a bottoms product stream; and propene oxide is separated from the overhead product stream. An acid is added to the propane depleted reaction mixture and/or to the distillation column at the same level or above the feed point for the propene depleted reaction mixture and/or contacted to the feed to the distillation column to provide an apparent pH in the bottoms product stream of from 3 to 4.5, which reduces the nitrogen content of the separated propene oxide.

The invention relates in a first aspect to a process for the preparation of propylene oxide, comprising: (i) providing a reaction mixture comprising propylene, water, organic solvent, and hydrogen peroxide; (ii) contacting the reaction mixture provided in (i) in an epoxidation zone with an epoxidation catalyst comprising a zeolitic material having a framework structure comprising Si, O, and Ti, and subjecting the reaction mixture to epoxidation reaction conditions in the epoxidation zone, obtaining, in the epoxidation zone, a mixture comprising propylene oxide, water, and organic solvent; (iii) removing an effluent stream from the epoxidation zone, the effluent stream comprising propylene oxide, water, and organic solvent; wherein the reaction mixture provided in (i) and subjected to (ii) contains in an amount of at most 500 mg per kg hydrogen peroxide comprised in said reaction mixture at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms. The invention further relates in a second aspect to a reaction mixture for preparing propylene oxide, comprising propylene, water, organic solvent, and hydrogen peroxide, wherein the reaction mixture comprises at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms in an amount of at most 500 mg per kg hydrogen peroxide comprised in the reaction mixture. In a third aspect, the invention relates to a system comprising an epoxidation catalyst comprising a zeolitic material having a framework structure comprising Si, O, and Ti, and further comprising the reaction mixture comprising propylene, water, and organic solvent according to the second aspect. In a fourth aspect, the invention relates to the use of an aqueous hydrogen peroxide solution as epoxidation agent for preparing propylene oxide in the presence of an organic solvent and an epoxidation catalyst comprising a zeolitic material having a framework structure comprising Si, O, and Ti, wherein the aqueous hydrogen peroxide solution comprises at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms in an amount of at most 500 mg per kg hydrogen peroxide comprised in the aqueous hydrogen peroxide solution.

The invention relates in a first aspect to a process for the preparation of propylene oxide, comprising: (i) providing a reaction mixture comprising propylene, water, organic solvent, and hydrogen peroxide; (ii) contacting the reaction mixture provided in (i) in an epoxidation zone with an epoxidation catalyst comprising a zeolitic material having a framework structure comprising Si, O, and Ti, and subjecting the reaction mixture to epoxidation reaction conditions in the epoxidation zone, obtaining, in the epoxidation zone, a mixture comprising propylene oxide, water, and organic solvent; (iii) removing an effluent stream from the epoxidation zone, the effluent stream comprising propylene oxide, water, and organic solvent; wherein the reaction mixture provided in (i) and subjected to (ii) contains in an amount of at most 500 mg per kg hydrogen peroxide comprised in said reaction mixture at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms. The invention further relates in a second aspect to a reaction mixture for preparing propylene oxide, comprising propylene, water, organic solvent, and hydrogen peroxide, wherein the reaction mixture comprises at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms in an amount of at most 500 mg per kg hydrogen peroxide comprised in the reaction mixture. In a third aspect, the invention relates to a system comprising an epoxidation catalyst comprising a zeolitic material having a framework structure comprising Si, O, and Ti, and further comprising the reaction mixture comprising propylene, water, and organic solvent according to the second aspect. In a fourth aspect, the invention relates to the use of an aqueous hydrogen peroxide solution as epoxidation agent for preparing propylene oxide in the presence of an organic solvent and an epoxidation catalyst comprising a zeolitic material having a framework structure comprising Si, O, and Ti, wherein the aqueous hydrogen peroxide solution comprises at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms in an amount of at most 500 mg per kg hydrogen peroxide comprised in the aqueous hydrogen peroxide solution.

Epoxidized fatty acid alkyl ester and methods for making epoxidized fatty acid alkyl ester. The epoxidized fatty acid alkyl ester is prepared from a fatty acid alkyl ester starting material comprising at least one of mono-unsaturated and di-unsaturated fatty acid alkyl ester molecules in a combined amount of at least 85 weight percent. Such epoxidized fatty acid alkyl esters can be employed in plasticizer compositions, either alone or in combination with other plasticizers, such as epoxidized natural oils. Such plasticizers in turn may be used in the formation of polymeric compositions.

Epoxidized fatty acid alkyl ester and methods for making epoxidized fatty acid alkyl ester. The epoxidized fatty acid alkyl ester is prepared from a fatty acid alkyl ester starting material comprising at least one of mono-unsaturated and di-unsaturated fatty acid alkyl ester molecules in a combined amount of at least 85 weight percent. Such epoxidized fatty acid alkyl esters can be employed in plasticizer compositions, either alone or in combination with other plasticizers, such as epoxidized natural oils. Such plasticizers in turn may be used in the formation of polymeric compositions.