Abstract: The invention provides a process for producing xylylenediamine, including supplying a solution of phthalonitrile dissolved in a solvent to a reactor filled with a catalyst and hydrogenating the phthalonitrile to produce xylylenediamine, characterized in that the process includes halting supply of the solution; (2) bringing a washing liquid into contact with the catalyst, the washing liquid having a phthalonitrile content of 3 mass % or less and a xylylenediamine content of 1 mass % or more; and after completion of the contact, resuming supply of the solution, and employing the catalyst continuously in hydrogenation. Through the production process of the invention, the catalyst can be employed continuously for a long period of time, and the catalyst-related cost can be considerably reduced.

Abstract: The invention provides a process for producing xylylenediamine, including supplying a solution of phthalonitrile dissolved in a solvent to a reactor filled with a catalyst and hydrogenating the phthalonitrile to produce xylylenediamine, characterized in that the process includes halting supply of the solution; (2) bringing a washing liquid into contact with the catalyst, the washing liquid having a phthalonitrile content of 3 mass % or less and a xylylenediamine content of 1 mass % or more; and after completion of the contact, resuming supply of the solution, and employing the catalyst continuously in hydrogenation. Through the production process of the invention, the catalyst can be employed continuously for a long period of time, and the catalyst-related cost can be considerably reduced.

Abstract: A method of producing xylylenediamine by a two-stage hydrogenation of a starting phthalonitrile in a solvent. The main steps of the method are a hydrogenation step 1 and a hydrogenation step 2. In the hydrogenation step 1, a solution of the starting phthalonitrile in the solvent containing liquid ammonia is fed to an inlet of a first reaction zone and the hydrogenation is carried out in the first reaction zone in the presence of a heterogeneous catalyst, to hydrogenate nitrile groups in the starting phthalonitrile to aminomethyl groups. A part of the hydrogenation product solution from the first reaction zone is circulated to the inlet of the first reaction zone and the rest is introduced into the hydrogenation step 2 where further undergoes the hydrogenation.

Abstract: A method of producing xylylenediamine of the present invention includes the steps of: subjecting a liquid mixture of phthalonitriles with liquid ammonia or a mixture of liquid ammonia and an organic solvent to a first catalytic hydrogenation treatment, thereby hydrogenating the phthalonitriles to obtain a reaction product (A), wherein a content of the liquid ammonia or the mixture of liquid ammonia and an organic solvent is 80 wt % or more; removing the liquid ammonia in the reaction product (A) to obtain a reaction product (B); subjecting the reaction product (B) to a second catalytic hydrogenation treatment, thereby hydrogenating cyanobenzylamine to obtain a reaction product (C); and distilling the reaction product (C) to purify xylylenediamine.

Abstract: In the production of carboxylic acid or carboxylic acid ester, a reaction product containing the carboxylic acid or carboxylic acid ester which has been produced by the reaction of an olefin, carbon monoxide, and water or an alcohol in the presence of HF is heat-treated in the presence of an acid catalyst and an acid adsorbent. By the heat treatment, the contamination of the carboxylic acid or carboxylic acid ester with HF and/or fluorine compounds such as acyl fluorides can be prevented, to enable the stable production of a high quality and high purity carboxylic acid or carboxylic acid ester without causing troubles such as corrosion of apparatus.

Abstract: A method of producing xylylenediamine by a two-stage hydrogenation of a starting phthalonitrile in a solvent. The main steps of the method are a hydrogenation step 1 and a hydrogenation step 2. In the hydrogenation step 1, a solution of the starting phthalonitrile in the solvent containing liquid ammonia is fed to an inlet of a first reaction zone and the hydrogenation is carried out in the first reaction zone in the presence of a heterogeneous catalyst, to hydrogenate nitrile groups in the starting phthalonitrile to aminomethyl groups. A part of the hydrogenation product solution from the first reaction zone is circulated to the inlet of the first reaction zone and the rest is introduced into the hydrogenation step 2 where further undergoes the hydrogenation.

Abstract: A method of producing xylylenediamine of the present invention includes the steps of: subjecting a liquid mixture of phthalonitriles with liquid ammonia or a mixture of liquid ammonia and an organic solvent to a first catalytic hydrogenation treatment, thereby hydrogenating the phthalonitriles to obtain a reaction product (A), wherein a content of the liquid ammonia or the mixture of liquid ammonia and an organic solvent is 80 wt % or more; removing the liquid ammonia in the reaction product (A) to obtain a reaction product (B); subjecting the reaction product (B) to a second catalytic hydrogenation treatment, thereby hydrogenating cyanobenzylamine to obtain a reaction product (C); and distilling the reaction product (C) to purify xylylenediamine.

Abstract: In a process for producing tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester by reacting tricyclo[5.2.1.02,6]deca-3-ene with carbon monoxide and alcohol in the presence of HF, carried out separately are (a) a step in which tricyclo[5.2.1.02,6]deca-3-ene is reacted with carbon monoxide to produce acyl fluoride and (b) a step in which acyl fluoride obtained in the step described above is reacted with alcohol to produce an ester. Also, the reaction conditions at the step (a) described above are selected or a step for carrying out isomerization reaction of tricyclo[5.2.1.02,6]decane-2-carboxylic fluoride obtained at the step (a) is interposed between the step (a) and the step (b). Further, the crude product of tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester thus obtained is subjected to contact treatment with specific glycol in the presence of an acid catalyst and then distilled.

Abstract: In the production method of the invention, a halogen-substituted aromatic compound is reacted with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride into a corresponding halogen-substituted aromatic aldehyde. By the use of hydrogen fluoride and boron trifluoride, the para position to halogen atom is selectively formylated to provide the halogen-substituted aromatic aldehyde in high yields in a short reaction time even at temperatures lower than room temperature.

Abstract: In the production of an alkylbenzaldehyde by a method comprising a step of preparing a solution of complex of a starting alkylbenzene and a hydrogen fluoride-boron trifluoride catalyst and a step of formylation by bringing the solution of complex into contact with carbon monoxide, an alkylbenzene having at least one primary alkyl group having two or more carbon atoms on its benzene ring is used as the starting alkylbenzene. The preparation of the solution of complex is carried out in the presence of an aliphatic or alicyclic saturated hydrocarbon having 6 to 10 carbon atoms which contains at least one tertiary carbon atom but contains no quaternary carbon atom. By the combined use of the specific alkylbenzene and the aliphatic or alicyclic saturated hydrocarbon, the disproportionation of the alkylbenzene is prevented and the alkylbenzaldehyde is produced at high yields.

Abstract: In the production of carboxylic acid or carboxylic acid ester, a reaction product containing the carboxylic acid or carboxylic acid ester which has been produced by the reaction of an olefin, carbon monoxide, and water or an alcohol in the presence of HF is heat-treated in the presence of an acid catalyst and an acid adsorbent. By the heat treatment, the contamination of the carboxylic acid or carboxylic acid ester with HF and/or fluorine compounds such as acyl fluorides can be prevented, to enable the stable production of a high quality and high purity carboxylic acid or carboxylic acid ester without causing troubles such as corrosion of apparatus.

Abstract: In the production of an alicyclic aldehyde, a starting aromatic aldehyde is converted into an aromatic acetal for protecting the formyl group. The aromatic ring of the aromatic acetal is then hydrogenated to convert the aromatic acetal into an alicyclic acetal, which is then hydrolyzed to cleave the acetal protecting group to obtain the aimed alicyclic aldehyde.

Abstract: 1,3-Naphthalenedicarboxylic acid is produced by oxidizing 1,3-dialkylnaphthalene in a liquid-phase with an oxygen-containing gas in the presence of a C2-C6 lower aliphatic carboxylic acid solvent and a catalyst comprising a heavy metal and a bromine compound. By regulating the ratio of the total number of bromine atoms fed into a reaction system to the total number of 1,3-dialkylnaphthalene molecules fed into the reaction system within a specific range, 1,3-naphthalenedicarboxylic acid is efficiently produced with low costs. Using 1,3-dimethylnaphthalene, as the starting 1,3-dialkylnaphthalene, which is produced by isomerizing dimethylnaphthalenes in a liquid phase in the presence of a catalyst comprising hydrogen fluoride and boron trifluoride together with a C5-C10 alicyclic saturated hydrocarbon having a five-membered or six-membered ring structure, a highly pure 1,3-naphthalenedicarboxylic acid is efficiently produced.

Abstract: In the production method of the invention, a halogen-substituted aromatic compound is reacted with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride into a corresponding halogen-substituted aromatic aldehyde. By the use of hydrogen fluoride and boron trifluoride, the para position to halogen atom is selectively formylated to provide the halogen-substituted aromatic aldehyde in high yields in a short reaction time even at temperatures lower than room temperature.

Abstract: An object of the present invention is to provide a process for producing high purity tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester which has a small content of an unsaturated compound and which has an excellent fragrance and is useful as a perfume or a perfume component. In a process for producing tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester by reacting tricyclo[5.2.1.02,6]deca-3-ene with carbon monoxide and alcohol in the presence of HF, carried out separately are (a) a step in which tricyclo[5.2.1.02,6]deca-3-ene is reacted with carbon monoxide to produce acyl fluoride and (b) a step in which acyl fluoride obtained in the step described above is reacted with alcohol to produce an ester, whereby tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester having a small content of an unsaturated compound can be obtained at a high yield. Also, the reaction conditions at the step (a) described above are selected or a step for carrying out isomerization reaction of tricyclo[5.2.1.

Abstract: In the production of an alkylbenzaldehyde by a method comprising a step of preparing a solution of complex of a starting alkylbenzene and a hydrogen fluoride-boron trifluoride catalyst and a step of formylation by bringing the solution of complex into contact with carbon monoxide, an alkylbenzene having at least one primary alkyl group having two or more carbon atoms on its benzene ring is used as the starting alkylbenzene. The preparation of the solution of complex is carried out in the presence of an aliphatic or alicyclic saturated hydrocarbon having 6 to 10 carbon atoms which contains at least one tertiary carbon atom but contains no quaternary carbon atom. By the combined use of the specific alkylbenzene and the aliphatic or alicyclic saturated hydrocarbon, the disproportionation of the alkylbenzene is prevented and the alkylbenzaldehyde is produced at high yields.

Abstract: In the process of the present invention, a polyalkyl-substituted aromatic aldehyde is produced by the formylation of a corresponding polyalkyl-substituted aromatic compound with carbon monoxide in the presence of hydrogen fluoride/boron trifluoride catalyst. By limiting the amount of hydrogen fluoride to a specific range, the formylation rapidly proceeds under mild conditions without causing the precipitation of solid matters even when the starting polyalkyl-substituted aromatic compound has alkyl groups on both the carbon atoms adjacent to the site to be formylated.

Abstract: In the production of an alicyclic aldehyde, a starting aromatic aldehyde is converted into an aromatic acetal for protecting the formyl group. The aromatic ring of the aromatic acetal is then hydrogenated to convert the aromatic acetal into an alicyclic acetal, which is then hydrolyzed to cleave the acetal protecting group to obtain the aimed alicyclic aldehyde.

Abstract: In the process of the present invention, a polyalkyl-substituted aromatic aldehyde is produced by the formylation of a corresponding polyalkyl-substituted aromatic compound with carbon monoxide in the presence of hydrogen fluoride/boron trifluoride catalyst. By limiting the amount of hydrogen fluoride to a specific range, the formylation rapidly proceeds under mild conditions without causing the precipitation of solid matters even when the starting polyalkyl-substituted aromatic compound has alkyl groups on both the carbon atoms adjacent to the site to be formylated.

Abstract: An information retrieval scheme using classification trees with respect to a plurality of information sources connected to a network is disclosed, where each classification tree having a hierarchical structure defined in terms of entries. In the information retrieval apparatus, classification tree class information for each classification tree class defined among entries constituting each classification tree is managed, where each classification tree class information indicating retrieval condition parameters for each classification tree class.