Disclosed are integrated systems and methods for the conversion of epoxides to beta lactones and to multiple C.sub.3 products and/or C.sub.4 products.

The object of the present invention is to provide a process for preparing a 5-alken-1-yne compound efficiently at low costs and a process for preparing (2E,6Z)-2,6-nonadienal by making use of the aforesaid process for preparing the 5-alken-1-yne compound. There is provided a process for preparing a 5-alken-1-yne compound of the following formula (4): YZCR.sup.1CR.sup.2(CH.sub.2).sub.2CCH (4) in which Y in formula (4) represents a hydrogen atom or a hydroxyl group, the process comprising at least steps of: subjecting (i) an alkenylmagnesium halide compound prepared from a haloalkene compound of the following formula (1): YZCR.sup.1CR.sup.2(CH.sub.2).sub.2X.sup.1 (1) and (ii) an alkyne compound of the following formula (2): X.sup.2CCSi(R.sup.3)(R.sup.4)(R.sup.5) (2) to a coupling reaction to form a silane compound of the following formula (3): YZCR.sup.1CR.sup.2(CH.sub.2).sub.2CCSi(R.sup.3)(R.sup.4)(R.sup.5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).

The object of the present invention is to provide a process for preparing a 5-alken-1-yne compound efficiently at low costs and a process for preparing (2E,6Z)-2,6-nonadienal by making use of the aforesaid process for preparing the 5-alken-1-yne compound. There is provided a process for preparing a 5-alken-1-yne compound of the following formula (4): YZCR.sup.1CR.sup.2(CH.sub.2).sub.2CCH (4) in which Y in formula (4) represents a hydrogen atom or a hydroxyl group, the process comprising at least steps of: subjecting (i) an alkenylmagnesium halide compound prepared from a haloalkene compound of the following formula (1): YZCR.sup.1CR.sup.2(CH.sub.2).sub.2X.sup.1 (1) and (ii) an alkyne compound of the following formula (2): X.sup.2CCSi(R.sup.3)(R.sup.4)(R.sup.5) (2) to a coupling reaction to form a silane compound of the following formula (3): YZCR.sup.1CR.sup.2(CH.sub.2).sub.2CCSi(R.sup.3)(R.sup.4)(R.sup.5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).

A method of producing an epoxy compound, which comprises reacting hydrogen peroxide with a compound having a carbon-carbon double bond, in the presence of at least one of a tungsten compound and a molybdenum compound; and an onium salt comprising 20 or more carbon atoms and one or more of substituents convertible to a functional group containing an active hydrogen or a salt thereof.

A compound represented by formula (II): ##STR00001## (where Ar represents a phenyl group optionally substituted by 1 to 3 substituents selected from the group consisting of a halogen atom and a trifluoromethyl group, and R represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms) is produced by step A: reacting trimethyl oxosulfonium salt or trimethyl sulfonium salt with a base in a solvent, and removing the resulting solid to obtain a trimethyl oxosulfonium ylide solution or a trimethyl sulfonium ylide solution; and step B: reacting a compound represented by formula (I): ##STR00002## and the solution obtained in step A, and the compound represented by formula (II) can be derived to a compound represented by formula (V): ##STR00003## that is useful for production of an antifungal agent.

A compound represented by formula (II): ##STR00001## (where Ar represents a phenyl group optionally substituted by 1 to 3 substituents selected from the group consisting of a halogen atom and a trifluoromethyl group, and R represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms) is produced by step A: reacting trimethyl oxosulfonium salt or trimethyl sulfonium salt with a base in a solvent, and removing the resulting solid to obtain a trimethyl oxosulfonium ylide solution or a trimethyl sulfonium ylide solution; and step B: reacting a compound represented by formula (I): ##STR00002## and the solution obtained in step A, and the compound represented by formula (II) can be derived to a compound represented by formula (V): ##STR00003## that is useful for production of an antifungal agent.

An ethylene bis-12-hydroxystearamide grafted glycidyl citrate (EBH-g-ECA) and a preparation method thereof are provided; the EBH-g-ECA can be used as a multifunctional auxiliary agent in a polymer material, and particularly has a chain extension and a crystal nucleation effect in a polyester polymer material. A heat-resistant polylactic acid continuously-extruded foamed material containing EBH-g-ECA is further provided. The continuous foaming technology can be realized by using the heat-resistant polylactic acid foamed material, and the prepared foamed product has a high heat resistance, a uniform appearance, a low density, and complete biodegradation. A polylactic acid foamed material preparation method for a heat-resistant is provided, which is easy to be industrialized and has a great significance for realizing the large-scale replacement of petroleum-based plastic disposable foamed products such as PP and PS.

An ethylene bis-12-hydroxystearamide grafted glycidyl citrate (EBH-g-ECA) and a preparation method thereof are provided; the EBH-g-ECA can be used as a multifunctional auxiliary agent in a polymer material, and particularly has a chain extension and a crystal nucleation effect in a polyester polymer material. A heat-resistant polylactic acid continuously-extruded foamed material containing EBH-g-ECA is further provided. The continuous foaming technology can be realized by using the heat-resistant polylactic acid foamed material, and the prepared foamed product has a high heat resistance, a uniform appearance, a low density, and complete biodegradation. A polylactic acid foamed material preparation method for a heat-resistant is provided, which is easy to be industrialized and has a great significance for realizing the large-scale replacement of petroleum-based plastic disposable foamed products such as PP and PS.

A compound represented by formula (II):

##STR00001##

(where Ar represents a phenyl group optionally substituted by 1 to 3 substituents selected from the group consisting of a halogen atom and a trifluoromethyl group, and R represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms)
is produced by
step A: reacting trimethyl oxosulfonium salt or trimethyl sulfonium salt with a base in a solvent, and removing the resulting solid to obtain a trimethyl oxosulfonium ylide solution or a trimethyl sulfonium ylide solution; and
step B: reacting a compound represented by formula (I):

##STR00002##

and the solution obtained in step A,
and the compound represented by formula (II) can be derived to a compound represented by formula (V):

##STR00003##

that is useful for production of an antifungal agent.

A compound represented by formula (II):

##STR00001##

(where Ar represents a phenyl group optionally substituted by 1 to 3 substituents selected from the group consisting of a halogen atom and a trifluoromethyl group, and R represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms)
is produced by
step A: reacting trimethyl oxosulfonium salt or trimethyl sulfonium salt with a base in a solvent, and removing the resulting solid to obtain a trimethyl oxosulfonium ylide solution or a trimethyl sulfonium ylide solution; and
step B: reacting a compound represented by formula (I):

##STR00002##

and the solution obtained in step A,
and the compound represented by formula (II) can be derived to a compound represented by formula (V):

##STR00003##

that is useful for production of an antifungal agent.