Abstract: Provided is a method for producing aldehydes that brings an excellent alcohol conversion and aldehyde selectivity while suppressing generation of aldol condensates, etc. The method for producing aldehydes includes a step of dehydrogenating primary alcohol in the presence of a catalyst composition. The catalyst composition is a first catalyst composition obtained by adding a potassium salt of a weak acid to a dehydrogenation catalyst containing copper as an active species.

Abstract: Provided is a fragrance composition containing a compound that is highly harmonious with other various fragrances and that can impart a stronger floral feeling by being blended. A fragrance composition containing 3,6-dimethyl-heptane-2-ol. The fragrance composition may further contain at least one selected from the group consisting of, for example, 7-methyloctane-3-ol, esters, carbonates, aldehydes, ethers, lactones, and alcohols other than 3,6-dimethylheptane-2-ol.

Abstract: Provided is a method for producing aldehydes that brings an excellent alcohol conversion and aldehyde selectivity while suppressing generation of aldol condensates, etc. The method for producing aldehydes includes a step of dehydrogenating primary alcohol in the presence of a catalyst composition. The catalyst composition is a first catalyst composition obtained by adding a potassium salt of a weak acid to a dehydrogenation catalyst containing copper as an active species.

Abstract: The present invention relates to [1] a method of producing 1-(2-t-butylcyclohexyloxy)-2-butanol including a step of hydrogenating 1-(2-t-butylphenyloxy)-2-butanol under a condition at a hydrogen pressure of from 1 to 5 MPa in the presence of a palladium catalyst (A) supported on peat-derived active carbon and a metal catalyst (B) containing one or more kinds of members selected from ruthenium, rhodium, platinum, and nickel; and [2] a perfume composition containing 1-(2-t-butylcyclohexyloxy)-2-butanol obtained by the foregoing method. According to the present invention, 1-(2-t-butylcyclohexyloxy)-2-butanol having a woody or amber-like fragrance as a perfume material and excellent fragrance notes can be obtained in a high purity because of a small remaining amount of a reaction intermediate and in a high yield.

Abstract: Provided is an alicyclic alcohol compound which can be used as a raw material for a compound perfume, and which has excellent floral-green-like aromas which are crisp and fresh; also provided are a manufacturing method for the same, and a perfume composition which contains the alicyclic alcohol compound. An alicyclic alcohol compound having a specified structure represented by chemical formula (1) has excellent floral-green-like aromas which are crisp and fresh; and a method for manufacturing the alicyclic alcohol compound represented by chemical formula (1) by reacting, in the presence of hydrogen fluoride, 1-isopropyl-4-methylcyclohexene and carbon monoxide, reacting the resulting 4-isopropyl-1-methylcyclohexane carboxylic acid fluoride with alcohol, and, after having acquired a cyclohexane carbonyl compound, reducing the cyclohexane carbonyl compound.

Abstract: Provided is an alicyclic alcohol compound which can be used as a raw material for a compound perfume, and which has excellent floral-green-like aromas which are crisp and fresh; also provided are a manufacturing method for the same, and a perfume composition which contains the alicyclic alcohol compound. An alicyclic alcohol compound having a specified structure represented by chemical formula (1) has excellent floral-green-like aromas which are crisp and fresh; and a method for manufacturing the alicyclic alcohol compound represented by chemical formula (1) by reacting, in the presence of hydrogen fluoride, 4-isopropyl-1-methylcyclohexene and carbon monoxide, isomerizing the resulting 4-isopropyl-1-methylcyclohexane carboxylic acid fluoride, thus making 2-methyl-2-(4-methylcyclohexyl)-propionyl fluoride, reacting with alcohol and acquiring a cyclohexane carbonyl compound, and then reducing the cyclohexane carbonyl compound.

Abstract: Provided is a fragrance composition containing a compound that is highly harmonious with other various fragrances and that can impart a stronger floral feeling by being blended. A fragrance composition containing 3,6-dimethyl-heptane-2-ol. The fragrance composition may further contain at least one selected from the group consisting of, for example, 7-methyloctane-3-ol, esters, carbonates, aldehydes, ethers, lactones, and alcohols other than 3,6-dimethylheptane-2-ol.

Abstract: The present invention relates to [1] a method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol including a step of adjusting a raw material mixture containing a 1-(2-t-butylphenyloxy)-2-alkanol represented by the formula (1) to a pH of from 7.5 to 10.0 and hydrogenating it in the presence of a palladium catalyst (A) and a metal catalyst (B) containing one or more kinds of members selected from ruthenium, rhodium, platinum, and nickel; and [2] a perfume composition containing a 1-(2-t-butylcyclohexyloxy)-2-alkanol obtained by the foregoing method. The present invention provides a method of efficiently producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol having a high trans-isomer content and a strong woody or amber-like fragrance as a perfume material and also having excellent persistence of aroma. (In the formula, R1 is a methyl group or an ethyl group.

Abstract: The present invention relates to [1] a method of producing 1-(2-t-butylcyclohexyloxy)-2-butanol including a step of hydrogenating 1-(2-t-butylphenyloxy)-2-butanol under a condition at a hydrogen pressure of from 1 to 5 MPa in the presence of a palladium catalyst (A) supported on peat-derived active carbon and a metal catalyst (B) containing one or more kinds of members selected from ruthenium, rhodium, platinum, and nickel; and [2] a perfume composition containing 1-(2-t-butylcyclohexyloxy)-2-butanol obtained by the foregoing method. According to the present invention, 1-(2-t-butylcyclohexyloxy)-2-butanol having a woody or amber-like fragrance as a perfume material and excellent fragrance notes can be obtained in a high purity because of a small remaining amount of a reaction intermediate and in a high yield.

Abstract: The present invention relates to [1] a method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol including a step of adjusting a raw material mixture containing a 1-(2-t-butylphenyloxy)-2-alkanol represented by the formula (1) to a pH of from 7.5 to 10.0 and hydrogenating it in the presence of a palladium catalyst (A) and a metal catalyst (B) containing one or more kinds of members selected from ruthenium, rhodium, platinum, and nickel; and [2] a perfume composition containing a 1-(2-t-butylcyclohexyloxy)-2-alkanol obtained by the foregoing method. The present invention provides a method of efficiently producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol having a high trans-isomer content and a strong woody or amber-like fragrance as a perfume material and also having excellent persistence of aroma. (In the formula, R1 is a methyl group or an ethyl group.

Abstract: Disclosed is a method for producing an alicyclic alcohol represented by general formula (III) which is useful as a starting material for a flavor mixture or the like at low cost in high yield. The alicyclic alcohol represented by general formula (III) is produced by preparing a cyclohexanecarbonyl compound represented by general formula (II) through the carbonylation of an unsaturated hydrocarbon represented by general formula (I) (preferably a compound obtained through the partial reduction of a diene compound) using carbon monoxide in the presence of HF, and thereafter reducing the cyclohexanecarbonyl compound. In formulae (I), (II), and (III), R1 represents an alkyl group having 1 to 4 carbon atoms, R2 represents an alkyl group having 1 to 4 carbon atoms, R3 represents an OH group, fluorine, or an OR4 group, and R4 represents an alkyl group having 1 to 4 carbon atoms.

Abstract: Provided is an alicyclic alcohol compound which can be used as a raw material for a compound perfume, and which has excellent floral-green-like aromas which are crisp and fresh; also provided are a manufacturing method for the same, and a perfume composition which contains the alicyclic alcohol compound. An alicyclic alcohol compound having a specified structure represented by chemical formula (1) has excellent floral-green-like aromas which are crisp and fresh; and a method for manufacturing the alicyclic alcohol compound represented by chemical formula (1) by reacting, in the presence of hydrogen fluoride, 4-isopropyl-1-methylcyclohexene and carbon monoxide, isomerising the resulting 4-isopropyl-1-methylcyclohexane carboxylic acid fluoride, thus making 2-methyl-2-(4-methylcyclohexyl)-propionyl fluoride, reacting with alcohol and acquiring a cyclohexane carbonyl compound, and then reducing the cyclohexane carbonyl compound.

Abstract: Provided is an alicyclic alcohol compound which can be used as a raw material for a compound perfume, and which has excellent floral-green-like aromas which are crisp and fresh; also provided are a manufacturing method for the same, and a perfume composition which contains the alicyclic alcohol compound. An alicyclic alcohol compound having a specified structure represented by chemical formula (1) has excellent floral-green-like aromas which are crisp and fresh; and a method for manufacturing the alicyclic alcohol compound represented by chemical formula (1) by reacting, in the presence of hydrogen fluoride, 1-isopropyl-4-methylcyclohexene and carbon monoxide, reacting the resulting 4-isopropyl-1-methylcyclohexane carboxylic acid fluoride with alcohol, and, after having acquired a cyclohexane carbonyl compound, reducing the cyclohexane carbonyl compound.

Abstract: The present invention relates to [1] a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), which includes the step of subjecting a 2-(1-hydroxyalkyl)cycloalkan-1-one to dehydration and isomerization in the co-existence of an acid and a platinum group metal catalyst, and [2] a process for producing an alkyl(3-oxo-alkylcycloalkyl)acetate which is useful as a perfume material, using the 2-alkyl-2-cycloalken-1-one: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.

Abstract: The present invention relates to a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), including the step of reacting a 2-alkylidene cycloalkanone in the presence of a palladium and/or platinum catalyst which is treated in the following steps (a) and (b); and a method for activating the palladium and/or platinum catalyst including the following steps (a) and (b): Step (a): activating the palladium and/or platinum catalyst in an atmosphere containing a hydrogen gas; and Step (b): replacing the hydrogen gas being present as the atmosphere for the catalyst in the step (a), with an inert gas to remove the hydrogen gas out of the reaction system, wherein m is 0 to 3; n is 1 or 2; R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; and R3 is an alkyl group having 1 to 5 carbon atoms. In accordance with the present invention, the 2-alkyl-2-cycloalken-1-one can be produced with a high purity and a high productivity.

Abstract: The present invention relates to a process for producing a 2-(1-hydroxyalkyl)cycloalkanone which includes the steps of (i) continuously mixing a cycloalkanone and an alkyl aldehyde in the water and a base catalyst to form a reaction system and allow both the compounds to react with each other; (ii) continuously withdrawing a reaction mixture produced in the step (i) out of the reaction system while allowing the step (i) to proceed; and (iii) adding an additional amount of water containing the base catalyst to the reaction system to maintain a constant concentration of the base catalyst and/or a constant amount of water in the reaction system while allowing the step (ii) to proceed.

Abstract: Disclosed is a method for producing an alicyclic alcohol represented by general formula (III) which is useful as a starting material for a flavor mixture or the like at low cost in high yield. The alicyclic alcohol represented by general formula (III) is produced by preparing a cyclohexanecarbonyl compound represented by general formula (II) through the carbonylation of an unsaturated hydrocarbon represented by general formula (I) (preferably a compound obtained through the partial reduction of a diene compound) using carbon monoxide in the presence of HF, and thereafter reducing the cyclohexanecarbonyl compound. In formulae (I), (II), and (III), R1 represents an alkyl group having 1 to 4 carbon atoms, R2 represents an alkyl group having 1 to 4 carbon atoms, R3 represents an OH group, fluorine, or an OR4 group, and R4 represents an alkyl group having 1 to 4 carbon atoms.

Abstract: The present invention relates to industrially useful production processes in which (±)-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-ones and further (±)-3a,6,6,9a-tetramethyldo decahydronaphtho[2,1-b]furans are produced from raw materials which are readily available at low costs, through short steps and in a simple manner.

Abstract: The present invention relates to a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), including the step of reacting a 2-alkylidene cycloalkanone in the presence of a palladium and/or platinum catalyst which is treated in the following steps (a) and (b); and a method for activating the palladium and/or platinum catalyst including the following steps (a) and (b): Step (a): activating the palladium and/or platinum catalyst in an atmosphere containing a hydrogen gas; and Step (b): replacing the hydrogen gas being present as the atmosphere for the catalyst in the step (a), with an inert gas to remove the hydrogen gas out of the reaction system, wherein m is 0 to 3; n is 1 or 2; R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; and R3 is an alkyl group having 1 to 5 carbon atoms. In accordance with the present invention, the 2-alkyl-2-cycloalken-1-one can be produced with a high purity and a high productivity.

Abstract: The present invention relates to [1] a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), which includes the step of subjecting a 2-(1-hydroxyalkyl)cycloalkan-1-one to dehydration and isomerization in the co-existence of an acid and a platinum group metal catalyst, and [2] a process for producing an alkyl(3-oxo-alkylcycloalkyl)acetate which is useful as a perfume material, using the 2-alkyl-2-cycloalken-1-one: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.