The invention provides a process for preparing an alcohol by hydrogenating an ester which is obtained by alkoxycarbonylating a C2 to C20 hydrocarbon having at least one multiple bond, preferably having at least one olefinic double bond, in which the homogeneous catalyst system used is separated from the product mixture by means of membrane separation. In a development of the present invention, the ester thus formed is converted to another ester by transesterification and then hydrogenated.

The invention provides a process for preparing an alcohol by hydrogenating an ester which is obtained by alkoxycarbonylating a C2 to C20 hydrocarbon having at least one multiple bond, preferably having at least one olefinic double bond, in which the homogeneous catalyst system used is separated from the product mixture by means of membrane separation. In a development of the present invention, the ester thus formed is converted to another ester by transesterification and then hydrogenated.

An object of the present invention is to provide an ester-based lubricating base oil for a fluid bearing that has a high viscosity index and excellent evaporation resistance, hydrolytic stability, and low-temperature fluidity. The present invention relates to a lubricating base oil for a fluid bearing containing a compound represented by general formula (1): ##STR00001##
wherein R.sup.1 represents a linear C.sub.2-C.sub.16 alkyl group, m represents an integer of 2 to 10, and n represents an integer of 4 to 14.

An object of the present invention is to provide an ester-based lubricating base oil for a fluid bearing that has a high viscosity index and excellent evaporation resistance, hydrolytic stability, and low-temperature fluidity. The present invention relates to a lubricating base oil for a fluid bearing containing a compound represented by general formula (1): ##STR00001##
wherein R.sup.1 represents a linear C.sub.2-C.sub.16 alkyl group, m represents an integer of 2 to 10, and n represents an integer of 4 to 14.

An object of the present invention is to provide a method for producing a propionic acid derivative with high productivity. The object can be achieved by a method for producing a compound represented by formula (1):

##STR00001##

wherein R.sup.1 is a halogen atom or the like, R.sup.2 and R.sup.3 are each independently a hydrogen atom, a halogen atom, or an organic group, X is an oxygen atom or a sulfur atom, R.sup.4 and R.sup.5 are each independently a hydrogen atom, a halogen atom, or a hydrocarbon group optionally having one or more substituents, R.sup.E is a hydrocarbon group optionally having one or more substituents; the method comprising step A of reacting a compound represented by formula (2):

##STR00002##

with a compound represented by formula (3):
M(R.sup.1).sub.n, wherein M is a cation, n is an integer corresponding to the valence of M, and a compound represented by formula (4):
R.sup.6—X—H; and
step B of separating, by filtration, the compound represented by formula (5): MF.sub.n from the mixture obtained by the above reaction.

An object of the present invention is to provide a method for producing a propionic acid derivative with high productivity. The object can be achieved by a method for producing a compound represented by formula (1):

##STR00001##

wherein R.sup.1 is a halogen atom or the like, R.sup.2 and R.sup.3 are each independently a hydrogen atom, a halogen atom, or an organic group, X is an oxygen atom or a sulfur atom, R.sup.4 and R.sup.5 are each independently a hydrogen atom, a halogen atom, or a hydrocarbon group optionally having one or more substituents, R.sup.E is a hydrocarbon group optionally having one or more substituents; the method comprising step A of reacting a compound represented by formula (2):

##STR00002##

with a compound represented by formula (3):
M(R.sup.1).sub.n, wherein M is a cation, n is an integer corresponding to the valence of M, and a compound represented by formula (4):
R.sup.6—X—H; and
step B of separating, by filtration, the compound represented by formula (5): MF.sub.n from the mixture obtained by the above reaction.

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (4), the method including the steps of: hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound (1) to obtain 7-methyl-3-methylene-7-octenal (2); reducing the 7-methyl-3-methylene-7-octenal (2) to obtain 7-methyl-3-methylene-7-octenol (3); and esterifying the 7-methyl-3-methylene-7-octenol (3) to obtain a 7-methyl-3-methylene-7-octenyl carboxylate compound (4). ##STR00001##

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (4), the method including the steps of: hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound (1) to obtain 7-methyl-3-methylene-7-octenal (2); reducing the 7-methyl-3-methylene-7-octenal (2) to obtain 7-methyl-3-methylene-7-octenol (3); and esterifying the 7-methyl-3-methylene-7-octenol (3) to obtain a 7-methyl-3-methylene-7-octenyl carboxylate compound (4). ##STR00001##

The present invention relates to the use of a transition metal catalyst TMC1, which comprises a transition metal M selected from metals of groups 7, 8, 9 and 10 of the periodic table of elements according to IUPAC and a tetradentate ligand of formula I wherein R.sup.1 are identical or different and are each an organic radical having from 1 to 40 carbon atoms, and R.sup.2 are identical or different and are each an organic radical having from 1 to 40 carbon atoms, as catalyst in processes for formation of compounds comprising at least one carboxylic acid ester functional group —O—C(═O)— starting from at least one primary alcohol and/or hydrogenation of compounds comprising at least one carboxylic acid ester functional group —O—C(═O)—. The present invention further relates to a process for hydrogenation of a compound comprising at least one carboxylic acid ester functional group —O—C(═O)—, to a process for the formation of a compound comprising at least one carboxylic acid ester functional group —O—C(═O)— by dehydrogenase coupling of at least one primary alcohol with a second alcoholic OH-group, to a transition metal complex comprising the tetradentate ligand of formula I and to a process for preparing said transition metal complex. ##STR00001##

The present invention relates to the use of a transition metal catalyst TMC1, which comprises a transition metal M selected from metals of groups 7, 8, 9 and 10 of the periodic table of elements according to IUPAC and a tetradentate ligand of formula I wherein R.sup.1 are identical or different and are each an organic radical having from 1 to 40 carbon atoms, and R.sup.2 are identical or different and are each an organic radical having from 1 to 40 carbon atoms, as catalyst in processes for formation of compounds comprising at least one carboxylic acid ester functional group —O—C(═O)— starting from at least one primary alcohol and/or hydrogenation of compounds comprising at least one carboxylic acid ester functional group —O—C(═O)—. The present invention further relates to a process for hydrogenation of a compound comprising at least one carboxylic acid ester functional group —O—C(═O)—, to a process for the formation of a compound comprising at least one carboxylic acid ester functional group —O—C(═O)— by dehydrogenase coupling of at least one primary alcohol with a second alcoholic OH-group, to a transition metal complex comprising the tetradentate ligand of formula I and to a process for preparing said transition metal complex. ##STR00001##