Mitsui Chemicals, Inc.

Mitsui Petrochemical Industries, Ltd.

Masayasu Ishibashi

Terunori Fujita

Hiroshi Iwasaki

Toshihiro Takai

Nobuya Hirokane

Tsuneyuki Ohkubo

Shigekazu Matsui

Katsuo Taniguchi

Kenji Fujiwara

Michio Tanaka

Akifumi Kagayama

Hideto Matsuoka

Hiroshi Kuroda

Masao Imai

Kazunori Takahata

Satoshi Inoki

Shinobu Aoki

Yoshito Kurano

Masahide Tanaka

Kinya Mizui

Shoji Hiraoka

Takashi Hayashi

Tetsuo Hayashi

Hiroyasu Ohno

Hajime Oyoshi

Naoya Sakamoto

Hideo Oikawa

Kozo Yasuda

Hiromi Ueki

Hiroshi Tomita

Toru Matsuyoshi

An object of the present invention is to provide a method of producing a corresponding olefin such as propylene with a high activity and a high selectivity even in a high LHSV range by an intramolecular dehydration reaction of an alcohol such as isopropyl alcohol. The present invention provides a method of producing an olefin represented by General Formula (II) below from an alcohol represented by General Formula (I) below, which method uses, as a dehydration catalyst, a chemically treated silica gel (X) in which an aluminum compound is supported onto a silica gel (A) with an average fine pore diameter of 10 to 50 nm in the amount of 1,000 to 10,000 ppm by weight in terms of aluminum element. (In General Formulae (I) and (II), Ris selected from alkyl groups of 1 to 5 carbon atoms and Ris selected from a hydrogen atom and alkyl groups of 1 to 5 carbon atoms.) 

Production method for olefin, and dehydration catalyst employed in same

The invention has objects of providing an olefin production method which can produce an olefin with high efficiency by the dehydration reaction of an alcohol even in the presence of a ketone without the occurrence of side reactions such as the Aldol condensation of the ketone, as well as providing an olefin production method which can produce an olefin with high activity and high selectivity in a single reaction step by directly reacting a corresponding ketone and hydrogen. The former olefin production method of the invention produces an olefin from an alcohol using a silica gel (A) as a dehydration catalyst which is obtained by bringing a silica gel (X) prepared from an alkyl orthosilicate into contact with a water-soluble aluminum compound and calcining the contact product or is obtained from a wet-process silica gel (Y) prepared from an alkali silicate and which contains an aluminum compound at 10 to 1000 ppm in terms of aluminum element as well as an alkali metal and an alkaline earth metal at a total of 0 to 350 ppm. The latter olefin production method produces an olefin from a ketone and hydrogen in a single reaction step in the presence of the silica gel (A) and a silver-containing inorganic substance (B).

Olefin production method

A novel olefin production process is provided which can be established as an industrial and practical process capable of producing olefins by directly reacting a ketone and hydrogen in a single reaction step. In particular, a novel olefin production process is provided in which propylene is obtained with high selectivity by directly reacting acetone and hydrogen. The olefin production process according to the present invention includes reacting a ketone and hydrogen in the presence of at least one dehydration catalyst and a silver-containing catalyst, and the at least one dehydration catalyst is selected from metal oxide catalysts containing a Group 6 element, zeolites, aluminas and heteropoly acid salts in which part or all the protons in heteropoly acids are exchanged with metal cations.

Olefin production process

A method for producing an alkylated aromatic compound includes a step (i) of producing a reaction product (a1) containing the alkylated aromatic compound and water by the reaction of an aromatic compound, a ketone, and hydrogen using a metal component containing at least one metallic element of copper, nickel, cobalt, and rhenium and a solid acid substance; a step (ii) of forming a dehydrated product (a2) from at least a portion of the reaction product (a1) by removing at least a portion of the water in the reaction product (a1); and a step (iii) of producing a reaction product (a3) containing the alkylated aromatic compound by bringing at least a portion of the dehydrated product (a2) into contact with a solid acid substance.

Method for producing alkylated aromatic compound, method for producing cumene, and method for producing phenol

According to a process of the invention, a ketone, an aromatic compound and hydrogen as starting materials are reacted together in a single reaction step to produce an alkylaromatic compound in high yield. A process for producing phenols in the invention includes a step of performing the above alkylation process and does not increase the number of steps compared to the conventional cumene process. The process for producing alkylated aromatic compounds includes reacting an aromatic compound such as benzene, a ketone such as acetone and hydrogen in the presence of a solid acid substance, preferably a zeolite, and a silver-containing catalyst.

Process for producing alkylated aromatic compounds and process for producing phenols

A process for producing an aromatic carboxylic acid by a liquid phase oxidation of an alkylaromatic compound with molecular oxygen in a reaction solvent comprising a lower aliphatic carboxylic acid in the presence of an oxidation catalyst, in which an aromatic carboxylic acid having an improved hue of the powdery product thereof and exhibiting an improved light transmittance when dissolved in an aqueous solution of a base can be produced efficiently in a simple manner by suppressing contamination due to the intermediates and by-products formed by side reactions, the said process comprising performing the liquid phase oxidation of the alkylaromatic compound in the presence of a hydrogen gas-treated liquid containing the catalyst.

Process for producing aromatic carboxylic acid

A method for producing aryl alkyl hydroperoxides which comprises selectively oxidizing an aryl alkyl hydrocarbon having the formula: ##STR1## wherein P and Q are hydrogen or an alkyl and may be the same or different from each other; x is an integer of 1-3; and Ar is an aromatic hydrocarbon group having a valence of x, with an oxygen-containing gas in the presence of a transition metal complex which contains, as a ligand, a cyclic polyfunctional amine compound having at least three nitrogen atoms in the ring forming molecular chain or an open chain polyfunctional amine compound having at least three nitrogen atoms in the main chain of the molecule.

Method for producing aryl aklyl hydroperoxides

Method for producing aryl alkyl hydroperoxides

Method for purifying crude naphthalenedicarboxylic acid

Process for producing polyethylene naphthalate

Lubricating oil containing aromatic ether compounds

A process for producing an alkyl-substituted aromatic hydrocarbon, which comprises alkylating an aromatic hydrocarbon with an alkylating agent in the presence of a heteropoly-acid or a salt thereof such as phosphorus tungstate and silicon tungstate as a catalyst. The process is particularly useful for preparing alkyl-substituted naphthalene or naphthalene derivatives.

Process for producing alkyl-substituted aromatic hydrocarbon using

In a process of producing isopropylnaphthols by oxidizing diisopropylnaphthalenes with molecular oxygen in a liquid phase to provide a reaction mixture which contains therein diisopropylnaphthalene monohydroperoxides and then acid decomposing the monohydroperoxides to isopropylnaphthols, the improvement comprising separating an organic layer from the reaction mixture, adding lower aliphatic alcohols of 1-4 carbons to the organic layer, crystallizing the diisopropylnaphthalenes while allowing the diisopropylnaphthalene monohydroperoxides to remain dissolved in the lower aliphatic alcohols, thereby to separate the monohydroperoxides from the diisopropylnaphthalenes. A further improvement in the process comprises crystallizing the isopropylnaphthols from aromatic hydrocarbons of 6-12 carbons.

Process of producing isopropylnaphthols

A process is disclosed which is capable of producing p,p'-biphenol of high purity by the dealkylation reaction of 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl and which yet allows isobutene to be recovered in high yield. The process performs the dealkylation reaction of 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl in the presence of an acid catalyst using as a solvent a saturated hydrocarbon having a boiling point of 190.degree. C. or above, an alicyclic hydrocarbon having a boiling point of 190.degree. C. or above, a hydrocarbon with an iodine value of no more than 1, sulfolane, or a mixture of these solvents. Also disclosed is a process for producing p,p'-biphenol from a mixture of 2,6-di-t-butyl-phenol and 3,3',5,5'-tetra-t-butyl-4,4'-diphenoquinone or from a mixture of 2,6-di-t-butylphenol, 3,3',5,5'-tetra-t-butyl-4,4'-diphenoquinone and 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl. In this process, the synthesis of 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl by the redox reaction between 2,6-di-t-butylphenol and 3,3',5,5'-tetra-t-butyl-4,4'-diphenoquinone and the production of p,p'-biphenol by the dealkylation reaction of 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl are performed at one stage in the presence of both an acid catalyst and a solvent at a temperature of 120.degree.-280.degree. C.

Process for producing p,p'-biphenol

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Yamaguchi, Japan

Masayasu Ishibashi