The present invention is to provide a method of producing a glyceric acid ester which is easy for production and high in yield, and in which a pyridine to be used for the reaction is easily reused. Provided is a method of producing a compound represented by the following formula (II), including a step of oxidatively esterifying Compound A represented by the following formula (I) with Compound B selected from an organic nitroxyl radical, an N-hydroxy form thereof, and a salt containing an oxo ammonium cation of them, and an oxidizing agent in the presence of a pyridine having an alkyl substituent, wherein the use amount of Compound B is 0.0001 or more and 0.1 or less in terms of a molar ratio relative to Compound A: ##STR00001##
wherein, in the formulae (I) and (II), R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a monovalent hydrocarbon group, or R.sup.1 and R.sup.2 are bonded to each other to form a divalent hydrocarbon group for constituting a ring structure.

The present invention relates to providing a novel glyceric acid ester which can be produced in a high yield and is expected to be applied as a synthetic intermediate, and a method of producing the same. In addition, the present invention relates to providing a novel glyceric acid ester which exhibits a high recovery in a water-washing step after the reaction and a small work load at the time of production, and is expected to be applied as a synthetic intermediate, and a method of producing the same. The present invention provides a method of producing a compound represented by the following formula (II), including a step of oxidatively esterifying a compound represented by the following formula (I): ##STR00001##
wherein, in the formulae (I) and (II), R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a monovalent hydrocarbon group, or R.sup.1 and R.sup.2 are bonded to each other to form a divalent hydrocarbon group for constituting a ring structure, provided that the case where R.sup.1 and R.sup.2 are a methyl group at the same time is excluded.

The present invention relates to uses of vanadium to convert aldehydes and ozonides into their respective acids and/or ketones. More particularly, this invention relates to the oxidative work-ups following ozonolysis using vanadium during ozonolysis, and using vanadium to oxidize aldehydes in general. The invention also relates to methods comprising the ozonolysis of oleyl alcohol in the presence of either an acid or an alcohol.

The present invention relates to uses of vanadium to convert aldehydes and ozonides into their respective acids and/or ketones. More particularly, this invention relates to the oxidative work-ups following ozonolysis using vanadium during ozonolysis, and using vanadium to oxidize aldehydes in general. The invention also relates to methods comprising the ozonolysis of oleyl alcohol in the presence of either an acid or an alcohol.

The present invention relates to providing a novel glyceric acid ester which can be produced in a high yield and is expected to be applied as a synthetic intermediate, and a method of producing the same. In addition, the present invention relates to providing a novel glyceric acid ester which exhibits a high recovery in a water-washing step after the reaction and a small work load at the time of production, and is expected to be applied as a synthetic intermediate, and a method of producing the same. The present invention provides a method of producing a compound represented by the following formula (II), including a step of oxidatively esterifying a compound represented by the following formula (I):

##STR00001##

wherein, in the formulae (I) and (II), R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a monovalent hydrocarbon group, or R.sup.1 and R.sup.2 are bonded to each other to form a divalent hydrocarbon group for constituting a ring structure, provided that the case where R.sup.1 and R.sup.2 are a methyl group at the same time is excluded.

Method for preparing a -hydroxyketone having 4 to 8 carbon atoms by reacting formaldehyde with a branched or unbranched dialkyl ketone having 3 to 7 carbon atoms in the liquid phase in a reactor in the presence of a basic component at a temperature of 50 to 150 C. and a pressure of 0.2 to 10 MPa abs, in which (a) a trialkylamine having 1 to 4 carbon atoms per alkyl group is used as basic component and the reaction (b) is carried out in the presence of 1 to 25% by weight water, based on the liquid phase, and (c) at a molar ratio of trialkylamine to formaldehyde in the liquid phase of from 1 to 5.

Method for preparing a -hydroxyketone having 4 to 8 carbon atoms by reacting formaldehyde with a branched or unbranched dialkyl ketone having 3 to 7 carbon atoms in the liquid phase in a reactor in the presence of a basic component at a temperature of 50 to 150 C. and a pressure of 0.2 to 10 MPa abs, in which (a) a trialkylamine having 1 to 4 carbon atoms per alkyl group is used as basic component and the reaction (b) is carried out in the presence of 1 to 25% by weight water, based on the liquid phase, and (c) at a molar ratio of trialkylamine to formaldehyde in the liquid phase of from 1 to 5.

Method for preparing a -hydroxyketone having 4 to 8 carbon atoms by reacting formaldehyde with a branched or unbranched dialkyl ketone having 3 to 7 carbon atoms in the liquid phase in a reactor in the presence of a basic component at a temperature of 50 to 150 C. and a pressure of 0.2 to 10 MPa abs, in which (a) a trialkylamine having 1 to 4 carbon atoms per alkyl group is used as basic component and the reaction (b) is carried out in the presence of 1 to 25% by weight water, based on the liquid phase, and (c) at a molar ratio of trialkylamine to formaldehyde in the liquid phase of from 1 to 5.

Method for preparing 1-hydroxy-2-methyl-3-pentanone (I) by reacting formaldehyde with diethyl ketone in a reactor in the presence of water and a basic component at a temperature of 50 to 150 C. and a pressure of 0.2 to 10 MPa abs, in which the basic component used is a trialkylamine from the group comprising trimethylamine, N,N-dimethylethylamine, N,N-diethylmethylamine, triethylamine, N,N-dimethyl-n-propylamine, N-ethyl-N-methyl-n-propylamine, N,N-dimethylisopropylamine, N-ethyl-N-methylisopropylamine, N,N-dimethyl-n-butylamine, N,N-dimethylisobutylamine and N,N-dimethyl-sec-butylamine, and from the reaction mixture obtained, trialkylamine as low boiler and a bottom product comprising 1-hydroxy-2-methyl-3-pentanone (I) as high boiler are separated in a distillation apparatus, wherein the distillation apparatus is operated at a top pressure of 0.2 to 1 MPa abs.

Method for preparing 1-hydroxy-2-methyl-3-pentanone (I) by reacting formaldehyde with diethyl ketone in a reactor in the presence of water and a basic component at a temperature of 50 to 150 C. and a pressure of 0.2 to 10 MPa abs, in which the basic component used is a trialkylamine from the group comprising trimethylamine, N,N-dimethylethylamine, N,N-diethylmethylamine, triethylamine, N,N-dimethyl-n-propylamine, N-ethyl-N-methyl-n-propylamine, N,N-dimethylisopropylamine, N-ethyl-N-methylisopropylamine, N,N-dimethyl-n-butylamine, N,N-dimethylisobutylamine and N,N-dimethyl-sec-butylamine, and from the reaction mixture obtained, trialkylamine as low boiler and a bottom product comprising 1-hydroxy-2-methyl-3-pentanone (I) as high boiler are separated in a distillation apparatus, wherein the distillation apparatus is operated at a top pressure of 0.2 to 1 MPa abs.