Daicel Chemical Industries, Ltd.

Daicel Corporation

Hiroto Tanigawa

Katsuya Maruo

Hiroto Miyake

Hiroshi Sakurai

Hiroshi Koyama

Hideyuki Takai

Takeshi Naito

Masanori Sakane

Kango Fujitani

Yoshiaki Morimoto

Kazuyuki Akita

Koichi Okumura

Kenji Oka

Akihiko Fujita

Toshihiko Nijukken

Yoshihiro Kihara

Hiroko Inoue

Tomoyuki Ono

Hiroshi Kimura

Tomio Ozaki

Masaya Uenoya

Provided is an alicyclic epoxy compound product used in applications for forming a cured product excellent in transparency and heat resistance. An alicyclic epoxy compound product of the present disclosure has a purity of a compound represented by Formula (1) of 85 wt. % or greater; and a total content of a compound represented by Formula (a) and a compound represented by Formula (b) of 0.5 wt. % or less, where X represents a single bond or a linking group. The alicyclic epoxy compound product of the present disclosure can be produced through subjecting a compound represented by Formula (1″) to a dehydration reaction to obtain a compound represented by Formula (1′), and reacting the resulting compound represented by Formula (1′) with an organic peracid.

Alicyclic epoxy compound product

Provided is an epoxy-amine adduct. The epoxy-amine adduct is a compound that may be a compound I containing two or more amino groups per molecule, a compound corresponding to the compound I, except being modified with a compound II-1 containing two or more (meth)acryloyl groups per molecule, a compound corresponding to the compound I, except being modified with a lactone II-2, or a salt of the compound I. The compound I is an adduct between an epoxide (A) containing two or more cycloaliphatic epoxy groups per molecule and an amine (B) containing two or more amino groups per molecule. The compound I includes a constitutional unit represented by Formula (I) and a constitutional unit represented by Formula (II) and contains amino groups at both ends. Formulae (I) and (II) are expressed as follows: 

Epoxy-amine adduct, thermoplastic resin composition, sizing agent, sizing agent coated carbon fiber, and fiber-reinforced composite material

A high-purity cycloaliphatic diepoxy compound of General Formula (II) is an epoxidized product of a cycloaliphatic diolefinic compound of General Formula (I) having an isomer content as detected in gas chromatography (GC) of 15% or less: wherein X represents a bivalent group selected from the group consisting of, for example, O, S, &#x2014;SO&#x2014;, &#x2014;SO&#x2014;, &#x2014;CH&#x2014;, and &#x2014;C(CH)&#x2014;; and Rto Rmay be the same as or different from each other and each represent hydrogen atom, a halogen atom, a hydrocarbon group which may contain oxygen atom or a halogen atom, or an alkoxy group which may be substituted. Such a high-purity cycloaliphatic diepoxy compound is prepared by producing the cycloaliphatic diolefinic compound through distillation, epoxidizing the compound with an aliphatic percarboxylic acid containing substantially no water, carrying out desolvation, and further purifying the epoxidized compound through distillation.

High-purity cycloaliphatic diepoxy compound and preparation process thereof

The present invention No. I is to obtain a high purity 3-alkoxy-1-propanol having the content of alcoholic impurities of not more than 0.3% by weight by allowing to react acrolein with a linear or branched alcohol having a carbon number of 1-4 using acrolein having the content of propionaldehyde of not more than 1% by weight as a raw material, a 3-alkoxy-1-propanol is produced by a hydrogenation reaction using hydrogen of a reaction mass under the presence of a catalyst, followed by recovering through a distillation of the 3-alkoxy-1-propanol having the content of alcoholic impurities of not more than 0.3% by weight from a crude solution in the hydrogenation reaction.

High purity 1,3-propanediol derivative solvent, process for producing the same, and use thereof

An alicyclic unsaturated alcohol (for example, tetrahydrobenzyl alcohol) having the purity of 99% by weight or more, the water content of 0.1% by weight or less and the acid value of 0.1 mg KOH/g or less can be produced, with high selectivity, by hydrogenating using an unsaturated cyclic aldehyde having the acid value of 10 mg KOH/g or less as a raw material; terminating the hydrogenation in the conversion of 70 to 99.8%; and rectifying the reaction product containing the unreacted unsaturated cyclic aldehyde. The high purity alicyclic unsaturated alcohol is useful as raw material chemicals for synthesizing drugs, agricultural chemicals, perfumes, and dyes etc.

Process for producing an alicyclic unsaturated alcohol

Heliotropin is oxidized with a percarboxylic acid in the presence of formic acid and an optionally added organic solvent, to thereby produce sesamol at high efficiency while suppressing by-production of heliotropic acid.

Method of producing sesamol formic acid ester and sesamol

Process for producing acetic anhydride alone or acetic anhydride and

A concentrated catalyst solution provided in the carbonylation reaction in which methyl acetate or dimethyl ether is chemically bonded with carbon monoxide in the presence of a catalyst system comprising a rhodium compound and an alkali metal iodide to produce acetic anhydride is subjected to a carbonylation treatment with carbon monoxide or a mixture of carbon monoxide and hydrogen before it is applied to a process for separating the tar contained in the catalyst solution, thereby increasing the iodide ion content of the catalyst solution, thus enabling the rhodium compound to be stabilized. When the concentration of the iodide ion in the concentrated catalyst solution is increased by this method, there is no possibility of the balances between the rhodium concentration and, the alkali metal concentration and the iodine concentration of the carbonylation reaction system being disturbed even when the catalyst solution as reprocessed is returned to the carbonylation reaction system. Further, the increase in the iodide ion concentration of the concentrated catalyst solution enables the rhodium compound contained in the concentrated catalyst solution to be stabilized, which prevents the rhodium compound from settling from the catalyst solution even during the heat treatment conducted for the purpose of removing components each having a low-boiling point contained in the catalyst solution before the process for separating and removing tar from the concentrated catalyst solution, so that the loss of the very expensive rhodium compound can be minimized.

Method for stabilizing rhodium compound

A concentrated catalyst solution used in a carbonylation reaction in which methyl acetate or dimethyl ether is chemically bonded with carbon monoxide in the presence of a catalyst system comprising a rhodium compound and an alkali metal iodide to produce acetic anhydride is subjected to a carbonylation treatment with carbon monoxide, or a mixture of carbon monoxide and hydrogen, before it is applied to a process for separating the tar contained in the catalyst solution, thereby increasing the iodide ion content of the catalyst solution and enabling the rhodium compound to be stabilized. The balances between the rhodium concentration, the alkali metal concentration and the iodine concentration of the carbonylation reaction system are not disturbed, even when the catalyst solution as reprocessed is returned to the carbonylation reaction system. Further, the increase in the iodide ion concentration of the concentrated catalyst solution enables the rhodium compound contained in the concentrated catalyst solution to be stabilized, and prevents the rhodium compound from settling from the catalyst solution, even during heat treatment conducted for the purpose of removing components having a low-boiling point contained in the catalyst solution before the process for separating and removing tar from the concentrated catalyst solution, so that the loss of the very expensive rhodium compound can be minimized.

A process for producing a carbonic acid ester which comprises reacting an alcohol with carbon monoxide and oxygen in the presence of a catalyst comprising a compound of divalent copper is disclosed, wherein the catalyst deactivated as a result of the carbonic acid ester-producing reaction is regenerated by subjecting a reaction mixture or a concentrate thereof containing the deactivated catalyst to water-replacement treatment, followed by heat treatment and weak-acid treatment.

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Ohtake, Japan

Hiroto Tanigawa