A process of generating a glycerol ether is provided. The process includes reacting isobutylene with an alcohol to obtain a tertiary alkyl ether through an etherification reaction and generating a glycerol ether from the tertiary alkyl ether and glycerol through a transetherification reaction, A system for generating a glycerol ether is also provided.

To provide a novel method for producing a halogenated acrylic acid derivative.

A compound represented by the formula (1):

##STR00001##

(wherein each of R.sup.1 and R.sup.2 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom, or R.sup.1 and R.sup.2 together form a ring, R.sup.3 is a monovalent group capable of being desorbed by R.sup.3OH removal reaction, and each of R.sup.4 and R.sup.5 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom) and having a boiling point of at most 500 C., is subjected to R.sup.3OH removal reaction in a vapor phase in the presence of a solid catalyst to obtain an ethene derivative represented by the formula (2):

##STR00002##

the ethene derivative represented by the formula (2) and a halogenated methane represented by the formula (3):

CHXYZ(3)

(wherein each of X, Y and Z which are independent of one another, is a halogen atom) are reacted in the presence of a basic compound and a phase transfer catalyst, to obtain a cyclopropane derivative represented by the formula (4):

##STR00003##

and the cyclopropane derivative represented by the formula (4) is reacted by heating in a liquid phase or in a vapor phase to obtain a halogenated acrylic acid ester derivative represented by the formula (5):

##STR00004##

To provide a novel method for producing a halogenated acrylic acid derivative.

A compound represented by the formula (1):

##STR00001##

(wherein each of R.sup.1 and R.sup.2 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom, or R.sup.1 and R.sup.2 together form a ring, R.sup.3 is a monovalent group capable of being desorbed by R.sup.3OH removal reaction, and each of R.sup.4 and R.sup.5 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom) and having a boiling point of at most 500 C., is subjected to R.sup.3OH removal reaction in a vapor phase in the presence of a solid catalyst to obtain an ethene derivative represented by the formula (2):

##STR00002##

the ethene derivative represented by the formula (2) and a halogenated methane represented by the formula (3):

CHXYZ(3)

(wherein each of X, Y and Z which are independent of one another, is a halogen atom) are reacted in the presence of a basic compound and a phase transfer catalyst, to obtain a cyclopropane derivative represented by the formula (4):

##STR00003##

and the cyclopropane derivative represented by the formula (4) is reacted by heating in a liquid phase or in a vapor phase to obtain a halogenated acrylic acid ester derivative represented by the formula (5):

##STR00004##

To provide a novel method for producing a halogenated acrylic acid derivative.

A compound represented by the formula (1):

##STR00001##

(wherein each of R.sup.1 and R.sup.2 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom, or R.sup.1 and R.sup.2 together form a ring, R.sup.3 is a monovalent group capable of being desorbed by R.sup.3OH removal reaction, and each of R.sup.4 and R.sup.5 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom) and having a boiling point of at most 500 C., is subjected to R.sup.3OH removal reaction in a vapor phase in the presence of a solid catalyst to obtain an ethene derivative represented by the formula (2):

##STR00002##

the ethene derivative represented by the formula (2) and a halogenated methane represented by the formula (3):

CHXYZ(3)

(wherein each of X, Y and Z which are independent of one another, is a halogen atom) are reacted in the presence of a basic compound and a phase transfer catalyst, to obtain a cyclopropane derivative represented by the formula (4):

##STR00003##

and the cyclopropane derivative represented by the formula (4) is reacted by heating in a liquid phase or in a vapor phase to obtain a halogenated acrylic acid ester derivative represented by the formula (5):

##STR00004##

The present disclosure provides a device for continuously preparing 2,6-dihydroxybenzaldehyde and use thereof. The device includes a first continuous reaction unit for hydroxy protection reaction, a second continuous reaction unit for lithiation and hydroformylation, and a third continuous reaction unit for deprotection reaction that are connected in series. The third continuous reaction unit includes: a first columnar continuous reactor, connected to the second continuous reaction unit and used for deprotection of the lithiated hydroformylated product while performing liquid separation to obtain an organic phase containing 2,6-dihydroxybenzaldehyde and an aqueous phase.

The present disclosure provides a device for continuously preparing 2,6-dihydroxybenzaldehyde and use thereof. The device includes a first continuous reaction unit for hydroxy protection reaction, a second continuous reaction unit for lithiation and hydroformylation, and a third continuous reaction unit for deprotection reaction that are connected in series. The third continuous reaction unit includes: a first columnar continuous reactor, connected to the second continuous reaction unit and used for deprotection of the lithiated hydroformylated product while performing liquid separation to obtain an organic phase containing 2,6-dihydroxybenzaldehyde and an aqueous phase.

The present disclosure provides a device for continuously preparing 2,6-dihydroxybenzaldehyde and use thereof. The device includes a first continuous reaction unit for hydroxy protection reaction, a second continuous reaction unit for lithiation and hydroformylation, and a third continuous reaction unit for deprotection reaction that are connected in series. The third continuous reaction unit includes: a first columnar continuous reactor, connected to the second continuous reaction unit and used for deprotection of the lithiated hydroformylated product while performing liquid separation to obtain an organic phase containing 2,6-dihydroxybenzaldehyde and an aqueous phase.

The present invention relates to a process for preparing a (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound of the following general formula (3-Z): wherein Y represents a halogen atom, Ar represents, independently of each other, an aryl group, and R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.1 and R.sup.2 may form together a divalent hydrocarbon group, R.sup.1-R.sup.2, having 2 to 10 carbon atoms, the process comprising: subjecting a (7Z)-11-halo-1,1-dialkoxy-7-undecene compound of the following general formula (1-Z): wherein X.sup.1 represents a halogen atom, and R.sup.1 and R.sup.2 are as defined above to a phosphonium salt formation reaction with a phosphine compound of the following general formula (2): wherein Ar is as defined above to form the (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound (3-Z). ##STR00001##

The present invention relates to a process for preparing a (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound of the following general formula (3-Z): wherein Y represents a halogen atom, Ar represents, independently of each other, an aryl group, and R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.1 and R.sup.2 may form together a divalent hydrocarbon group, R.sup.1-R.sup.2, having 2 to 10 carbon atoms, the process comprising: subjecting a (7Z)-11-halo-1,1-dialkoxy-7-undecene compound of the following general formula (1-Z): wherein X.sup.1 represents a halogen atom, and R.sup.1 and R.sup.2 are as defined above to a phosphonium salt formation reaction with a phosphine compound of the following general formula (2): wherein Ar is as defined above to form the (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound (3-Z). ##STR00001##

The present invention is directed to a process for the manufacture of 1,1,4,4-tetramethoxy-2-butene from 2,5-dimethoxy-2,5-dihydrofuran with methanol in the presence of an acidic ion exchanger as catalyst, whereby the molar ratio of 2,5-dimethoxy-2,5-dihydrofuran to methanol is 1:45. The present invention is further directed to a process of separating 1,1,4,4-tetramethoxy-2-butene, methanol and 2,5-dimethoxy-2,5-dihydrofuran from each other and H2O whereby a basic compound, preferably a basic metal salt or a basic ion exchanger, is present. Both processes can be carried out on an industrial scale, batch-wise or in continuous mode and are sustainable since the selectivity and the space-time-yields are high and less waste compared to known processes is produced. Further objects of the present invention are the use of a basic compound in the distillation of a mixture comprising H2O, 1,1,4,4-tetramethoxy-2-butene and 2,5-dimethoxy-2,5-dihydrofuran, as well as the use of an acidic ion exchanger as catalyst in a reaction of 2,5-dimethoxy-2,5-dihydrofuran with methanol to 1,1,4,4-tetramethoxy-2-butene, whereby the molar ratio of 2,5-dimethoxy-2,5-dihydrofuran to methanol is 1:45.