Mitsui Toatsu Chemicals, Incorporated

Tsutomu Takase

Yoshio Morimoto

Teruo Yuasa

Minoru Hattori

Takayoshi Masuda

Noboru Yamazaki

Nobukatsu Kato

Yoshimoto Watanabe

Kunio Hanauye

Mitsuhiro Iwasa

Nobukatu Kato

Satoshi Numata

Masaru Honjo

Mizuo Ito

Fumio Yamazaki

Toshio Itakura

Takashi Kataoka

Kosuke Mimaki

Tomitaka Yamamori

Kunio Aoi

This invention provides a method for purifying crude fatty acid esters of saccharide containing at least fatty acid glycerides as impurity, and which method comprises decomposing the fatty acid glycerides by the treatment thereof with a lipid splitting enzyme or with a combination of a lipid splitting enzyme and a reducing agent in the presence of water.

Method for purifying fatty acid esters of saccharide

Disclosed is a heat-resistant and fast-curing thermosetting resin composition suitably for insulating materials and comprising (a) a bismaleimide and/or a polymaleimide compound and (b) at least one compound selected from alkenylphenol derivatives, linear dimers thereof, and polymers thereof. In addition to components (a) and (b), this resin composition can contain (c) a polymerizable unsaturated compound.

Thermosetting resin composition from maleimide compound and alkenyl

An improved process for producing hydroquinone from p-isopropenyl phenol is disclosed. Hydroquinone is obtained by oxidizing p-isopropenyl phenol with hydrogen peroxide or an organic peroxide as an oxidizing agent at a temperature of 28.degree. to 50.degree. C. in the presence of a strong acid catalyst using a slightly or hardly water-soluble high-boiling polar solvent. In the oxidation reaction, the mole ratio of the oxidizing agent to p-isopropenyl phenol is kept at less than 1. After the reaction, in order to effectively decompose or consume the undecomposed p-isopropenyl phenol hydroperoxide and the unreacted oxidizing agent remaining in the reaction mixture, the reaction mixture is aged. Alternatively, or subsequently to the aging reaction, SO.sub.2 is added to the reaction mixture to completely decompose the undecomposed or unreacted peroxide. Thus, hydroquinone of high purity is obtained.

Process for producing hydroquinone

A novel process for producing alkenyl phenols, which comprises continuously feeding a dihydroxydiphenyl alkane such as 2,2-(4,4'-dihydroxydiphenyl)propane, 2,2-(4,4'-dihydroxy-3,3'-dimethyldiphenyl)propane, 2,2-(4,4'-dihydroxydiphenyl)butane, 2,2-(4,4'-dihydroxydiphenyl)-4-methylpentane, 1,1,1-(4,4'-dihydroxytriphenyl)ethane and 1,1-(4,4'-dihydroxydiphenyl)cyclohexane into a high-boiling inert organic reaction medium such as an alkylnaphthalene containing a basic catalyst and heated at 150.degree. to 250.degree. C. under 10 to 100 mmHg while maintaining the concentration of the dihydroxydiphenyl alkane in the reaction medium at not more than 30% by weight, thereby cleaving it in the reaction medium; and continuously distilling off the cleavage product out of the reaction system and recovering it. This process can afford the corresponding highly pure alkenyl phenol as a monomer and/or its polymer almost quantitatively.

Process for cleaving dihydroxydiphenyl alkanes

A novel process for producing isopropenyl phenol such as p-isopropenyl phenol which comprises continuously feeding oligomers of isopropenyl phenol having a degree of polymerization of 2 to 5 into a high-boiling inert organic reaction medium such as an alkylnaphthalene heated at 150.degree. to 250.degree. C. under a pressure of 10 to 100 mmHg while maintaining the concentration of the oligomers in the reaction medium at not more than 30% by weight, thereby thermally decomposing the oligomers in the reaction medium; and continuously distilling off the resulting isopropenyl phenol out of the reaction system and recovering it. The process almost quantitatively gives isopropenyl phenol having reduced contents of impurities.

Process for preparing isopropenyl phenol

An improved process for the production of polytetramethylene ether glycol is disclosed. Polytetramethylene ether glycol is obtained with a high yield by subjecting tetrahydrofuran to ring opening polymerization in the presence or absence of an organic solvent with the use of, as a catalyst, a lithium halide in conjunction with fuming sulfuric acid. Average molecular weight of the glycol product can be controlled in the range of 1000-3000 at will by varying the amounts of the lithium halide and fuming sulfuric acid used.

Process for the production of polytetramethylene ether glycol

A novel trimer of p-isopropenyl phenol of the structure ##STR1## which is useful as a material or a curing agent for epoxy resins. The linear trimer includes a cis-isomer (m.p. 225.5.degree.-227.degree. C.) and a trans-isomer (m.p. 167.degree.-168.degree. C.). It is prepared by reacting p-isopropenyl phenol or its linear polymer in the presence of an acid catalyst such as sulfuric acid, boron fluoride or activated clay in an aromatic hydrocarbon, halogenated hydrocarbon, substituted aromatic hydrocarbon or aprotic polar solvent (e.g., benzene, carbon tetrachloride, nitrobenzene or dioxane).

Process for producing a linear trimer of paraisopropenyl phenol

A new resol-type phenol resin is described which is obtained by heat-reacting isopropenylphenol oligomer as partial or whole phenol component of the resin with an aldehyde in the presence of a basic catalyst. Varnishes are obtained by adding a suitable vehicle to the resin. Laminates manufactured by impregnating a base with the phenol resin and heating the impregnated base to cure the resin are obtained with superior mechanical and electrical characteristics.

Laminates prepared from resol-type phenol resins

A drying oil such as isomerized linseed oil, dehydrated castor oil or the like oil which has an iodine value of more than 140 and a content of conjugated double bonds of less than 50% is reacted with isopropenylphenol and/or oligomers thereof in an amount, by weight, of 0.1-2 times as great as that of the drying oil in the presence of a small amount of an acid at a temperature of 65-150.degree. C. for 0.5-3 hours. By the reaction, isopropenylphenol and/or its oligomers are introduced to the drying oil while leaving the double bonds of the oil as they are without disappearance. The thus introduced oil is further reacted with a phenol or phenols under strongly acidic conditions to introduce the phenols thereto. The drying oil which has been introduced with the isopropenylphenol and/or its oligomers and also with the phenols is mixed with a phenol or phenols and then reacted with formaldehyde to give a modified phenolic resin. This phenolic resin is useful for making a phenolic laminate with improved flexibility, punching quality and water proof.

Process for producing modified phenolic resin

Chemically stable p-isopropenyl phenol is produced in the form of a solution by contacting p-isopropenyl phenol, in the form of a gas or a liquid obtained immediately after condensation of said gas, with a polar solvent such as an alcohol, an ester, or an acid amide. The resultant solution of p-isopropenyl phenol can be used as the starting material for subsequent reaction to obtain useful compounds such as hydroquinone. Alternatively, p-isopropenyl phenol may be isolated in crystalline form by adding to the solution a poor solvent for the phenol such as water, or by cooling the solution.

Method for the preparation of p-isopropenyl phenol

Unsaturated dimers which contain 2,4-diphenyl-4-methyl-1-pentene as their main component (i.e., in an amount of greater than 95%) are produced by reacting an .alpha.-methylstyrene at a temperature of from 20.degree. to 100.degree.C. in the presence of a sulfonic acid type cation-exchange resin catalyst and in the further presence of a primary or secondary monohydric alcohol containing from 2 to 5 carbon atoms. By this reaction, side products including a saturated dimer of 1,1,3-trimethyl-3-phenylindane, trimers and higher polymers are produced only in an extremely small amount. The unsaturated dimers are very useful as a molecular weight modifier when employed, instead of dodecylmercaptans, for the production of polymers such as an ABS resin, an AS resin, and the like.

Method for the preparation of unsaturated dimers of

2,6-DI-TERT.-BUTYL-4-CUMYL PHENOL IS PRODUCED BY REACTING P-CUMYL PHENOL WITH ISOBUTYLENE, AT A REACTION TEMPERATURE OF FROM 40.degree. TO 120.degree.C. in the presence of from 0.01 to 20% by weight of p-toluene sulfonic acid based on the weight of the p-cumyl phenol. Isobutylene is charged into the reaction system at a high rate and is always present in the reaction system during the reaction. A substantially 100% conversion of p-cumyl phenol is attained and the weight ratio of 2,6-di-tert.-butyl-4-cumyl phenol/2-tert.-butyl-4-cumyl phenol in the reaction product is greater than 10, while splitting off of the cumyl group at the para position is suppressed.

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Nagoya, Japan

Tsutomu Takase