Mitsubishi Gas Chemical Company, Inc.

Norio Fushimi

Makoto Takagawa

Toshio Hidaka

Takafumi Yoshimura

Kenji Inamasa

Ko Kedo

Takeshi Kawai

Kazuhiro Yamada

Yoshifumi Sato

Mitsuharu Kitamura

Takafumi Abe

Kenichi Nakamura

Yutaka Kanbara

Masaharu Doya

Kinji Kato

Akio Hashimoto

Junya Nishiuchi

Takayo Sasaki

Youichi Kyuuko

A process of production of an aromatic alcohol or a heterocyclic aromatic alcohol, containing a step of reacting an aromatic amine or a heterocyclic aromatic amine having an aromatic ring or a heterocyclic aromatic ring having thereon at least one substituent &#x2014;CHRNRR(wherein R, Rand Reach independently represent hydrogen, an alkyl group having from 1 to 4 carbon atoms, or a benzyl group), with an alcohol, in the presence of a basic catalyst.

Process for production of aromatic alcohol or heterocyclic aromatic alcohol

A process for effectively producing a 4-(4-alkylcyclohexyl)benzaldehyde, 4-(cyclohexyl)benzaldehyde, a 4-(trans-4-alkylcyclohexyl)benzaldehyde and a (trans-4-alkylcyclohexyl)benzene useful for electronic material applications such as liquid crystals and for pharmaceutical and agrochemical applications, etc., are disclosed. The present invention provides (1) a process for producing a 4-(4-alkylcyclohexyl)benzaldehyde or 4-(cyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene or cyclohexylbenzene with carbon monoxide, (2) a process for producing a 4-(trans-4-alkylcyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene having a cis/trans molar ratio of 0.3 or less with carbon monoxide, and (3) a process for producing a (trans-4-alkylcyclohexyl)benzene by isomerizing a mixture of the cis and trans isomers of a (4-alkylcyclohexyl)benzene, all of the processes being performed in the presence of HF and BF.

4-(4-alkylcyclohexyl)benzaldehyde

Provided is a production method for an iodine compound in which iodine is reacted with a substrate in the presence of a porous material having a pore diameter of 500 nm or less or in the presence of the above porous material and an oxidizing agent and a production process for high purity 5-iodo-2-methylbenzoic acid comprising an iodination reaction step carried out by the above-mentioned, a crystal precipitation and separation step in which a product is precipitated by adding water or cooling and then separated and a purification step in which crystal separated is recrystallized using an organic solvent. According to the production method for an iodine compound described above, iodine can be introduced into various substrates at a high selectivity. Since expensive metals and specific reagents do not have to be used, it can readily be carried out in an industrially scale, and the product having a high purity can be obtained. Further, the process comprising the iodination reaction, separation and purification steps described above makes it possible to readily obtain at a high yield, 5-iodo-2-methylbenzoic acid having a high purity which is useful in uses for functional chemical products such as medicines. The process of the present invention comprising iodination reaction, separation and purification steps is characterized by that it is simple in terms of a procedure and that the purification load is smaller, and it is very advantageous in industrially carrying out.

Process for production of iodine compounds and process for production of high-purity 5-iodo-2-methylbenzoic acid

The present invention provides a process for producing 5-iodo-2-methylbenzoic acid through iodination of 2-methylbenzoic acid, the process including, as essential steps, a reaction step of iodinating 2-methylbenzoic acid in the presence of a microporous compound, iodine, an oxidizing agent, and acetic anhydride, and a purification step including sublimation, distillation, crystallization, or a combination of two or more of these. According to the present invention, 5-iodo-2-methylbenzoic acid, which is useful for producing functional chemicals such as drugs, can be produced at high purity and high yield in a simple manner. Since the production process includes a simple reaction step and a simple separation/purification step, the load of purification is mitigated. In addition, the microporous compound such as a zeolite catalyst which has been separated and recovered from the reaction mixture can be repeatedly employed after performing of a simple treatment. Thus, the production process ensures a long service life of catalysts and high efficiency.

Process for producing 5-iodo-2-methylbenzoic acid

Provided is a one-step efficient production method for an &#x3b1;,&#x3b1;-difluoroamine of a general formula (1) below from an amide compound. The method is an economical method capable of producing the intended &#x3b1;,&#x3b1;-difluoroamine at high yield by reacting a starting amide compound with carbonyl fluoride and/or oxalyl fluoride under a specific condition. Formula (1) 

Method for producing fluoroamine

The process for producing a (fluoroalkyl)benzene derivative according to the present invention comprises a step of reducing the total content of group 3 to group 12 transition metals in an alkylbenzene derivative to 500 ppm or less in terms of metal atoms; a step of halogenating the branched alkyl group of the purified alkylbenzene derivative by a photohalogenation to obtain a (haloalkyl)benzene derivative; and a step of subjecting the (haloalkyl)benzene derivative to a halogen-fluorine exchange using HF in an amount of 10 mol or higher per one mole of the (haloalkyl)benzene derivative. The (fluoroalkyl)benzene derivative produced by the process is reduced in the content of impurities such as residual halogens and residual metals, and is useful as intermediates for functional chemical products for use in applications such as medicines and electronic materials.

High-purity (fluoroalkyl)benzene derivative and process for producing the same

A method for producing 2-amino-5-iodobenzoic acid which comprises bringing 2-aminobenzoic acid (A) and molecular iodine (B) into reaction with each other in the liquid phase in the presence of an oxidizing agent. Hydrogen peroxide is preferable as the oxidizing agent. This method does not require a step for purifying 2-amino-5-iodobenzoic acid or a step for recovering iodine, and 2-amino-5-iodobenzoic acid having excellent quality can be produced economically advantageously with a great yield. The product can be advantageously used as an intermediate for drugs, an agricultural chemical and a raw material for functional chemicals.

Method for producing 2-amino-5-iodobenzoic acid

A fluorine compound represented by Formula (1) is provided. The above fluorine compound is effective for introducing a fluorine atom into a compound having an active group such as an oxygen-containing functional group, and it can be used for uses of surface treatment, cleaning and coating. Further, after the fluorination reaction, the above compound is recovered and can be reused as a starting material for producing the above fluorine compound, and it is useful for various fluorination processes. (wherein X represents a nitrogen or phosphorus atom; R, R, and Rrepresent hydrogen, an alkyl group or aryl group which may have a substituent, and they each may be the same or different; and R, R, and Rmay be combined with each other to form a ring).

Fluorine compound and fluorinating agent comprising the compound

A fluorine compound represented by Formula (1) is provided. The above fluorine compound is effective for introducing a fluorine atom into a compound having an active group such as an oxygen-containing functional group, and it can be used for uses of surface treatment, cleaning and coating. Further, after the fluorination reaction, the above compound is recovered and can be reused as a starting material for producing the above fluorine compound, and it is useful for various fluorination processes.(wherein X represents a nitrogen or phosphorus atom; R, R, and Rrepresent hydrogen, an alkyl group or aryl group which may have a substituent, and they each may be the same or different; and R, R, and Rmay be combined with each other to form a ring).

5-Tolyl-pent-2-ene is cyclized in liquid phase in the present of an aliphatic hydrocarbon to produce the corresponding dimethyltetralin. The use of the aliphatic hydrocarbon effectively prevents a side reaction such as dimerization of 5-tolyl-pent-2-ene to provide dimethyltetralin in a high yield. Also, 5-tolyl-pent-2-ene is cyclized in liquid phase or vapor phase in the presence of a catalyst comprising a carrier supporting sulfate ions to produce the corresponding dimethyltetralin. The catalyst supporting sulfate ions shows a high catalytic activity event at low temperatures. Therefore, the cyclization of 5-tolyl-pent-2-ene is conducted in a wide temperature range from low temperatures to high temperatures.

Process for producing dimethyltetralin

A process for producing a monoalkenyl aromatic hydrocarbon which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom at the .alpha.-position of a side chain (such as o-xylene) with a conjugated diene having 4 or 5 carbon atoms in the presence of a catalyst slurry prepared by adding an aromatic hydrocarbon compound to a catalyst comprising a alkali metal and an alkali metal compound. In the aforementioned process, it is particularly effective that the catalyst slurry is prepared by adding the aromatic hydrocarbon compound after the aromatic hydrocarbon compound has been deoxygenated and dehydrated by distillation, and the catalyst slurry thus prepared is supplied to the reaction system. According to the aforementioned process, an industrially useful monoalkenyl aromatic hydrocarbon compound, such as a monoalkenylbenzene, can be produced at a high selectivity, in a high yield, and with enhanced safety and stability for a long time.

Process for producing a monoalkenyl aromatic hydrocarbon compound

Provided is a process for producing alkylbenzoyl chloride which comprises reacting alkylbenzaldehyde with chlorine at a temperature of -10.degree. to 80.degree. C. under a pressure of 5 kg/cm.sup.2 or below in a liquid phase, whereby alkylbenzoyl chloride can be produced in a high yield and at a low price.

Process for producing alkylbenzoyl chloride

There is disclosed a process for producing a monoalkenylbenzene which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom bonded at .alpha.-position of the side chain (such as xylene) with a conjugated diene having 4 or 5 carbon atoms (such as butadiene) in the presence of a catalyst produced by calcining the mixture of a basic potassium compound and alumina and then heat treating the calcined product together with metallic sodium in an atmosphere of an inert gas. According to the aforesaid process, an industrially useful monoalkenylbenzene can be produced in high yield at a low cost with enhanced safety.

There is disclosed a process for producing a monoalkenylbenzene which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom bonded at .alpha.-position of the side chain (such as xylene) with a conjugated diene having 4 or 5 carbon atoms (such as butadiene) in the presence of a catalyst produced by calcining the mixture of potassium hydroxide and aluminum hydroxide and then heat treating the calcined product together with metallic sodium in an atmosphere of an inert gas. According to the aforesaid process, an industrially useful monoalkenylbenzene can be produced in high yield at a low cost with enhanced safety.

A process for producing a monoalkenyl aromatic hydrocarbon compound which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom bonded at an .alpha.-position of the side chain (such as xylene) with a conjugated diene having 4 or 5 carbon atoms (such as butadiene) in the presence of a catalyst comprising a mixture obtained by heat treating metallic sodium together with a mixture of an aluminum oxide and a potassium compound in an inert gas atmosphere. The process produces a commercially useful monoalkenyl aromatic hydrocarbon compounds in a high yields and at a low cost with enhanced safety.

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Okayama, Japan

Norio Fushimi