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1. 发明专利

JPH02174752A PRODUCTION OF DL-SERINE 失效
公开(公告)号：JPH02174752A
公开(公告)日：1990-07-06
申请号：JP32985188
申请日：1988-12-27
申请人： LIGHT OIL UTILIZATION RES ASS
发明人： KUJIRA KATSUFUMI , YOKOI TAKASHI , ODAGIRI MASAKI , IMANARI MAKOTO
IPC分类号： C07C227/12 , C07C229/22
摘要： PURPOSE:To industrially obtain the subject compound useful as an amino acid transfusion solution, etc., in high yield at a low cost by subjecting glycolaldehyde as a reaction substrate to the Strecker reaction at specific raw material ratios under specified reaction conditions and then hydrolyzing the resultant reaction product. CONSTITUTION:Glycolaldehyde as a reaction substrate is subjected to the Strecker reaction at raw material molar ratios of 1.01-1.30 glycolaldehyde/ cyanogen compound (e.g. sodium cyanide), 1.01-1.50 ammonium chloride/ glycoladehyde and 1.0-7.0 ammonia/cyanogen compound under reaction conditions of 20-80 deg.C temperature for 15-120min time to synthesize serine, which is further hydrolyzed to afford DL-serine.

2. 发明专利

JPH02174742A PREPARATION OF GLYCOLALDEHYDE 失效
公开(公告)号：JPH02174742A
公开(公告)日：1990-07-06
申请号：JP32985088
申请日：1988-12-27
申请人： LIGHT OIL UTILIZATION RES ASS
发明人： YOKOI TAKASHI , SETO TAKATOSHI , ODAGIRI MASAKI , IMANARI MAKOTO
IPC分类号： B01J23/80 , C07B61/00 , C07C45/38 , C07C47/19
摘要： PURPOSE:To efficiently and continuously provide the subject highly pure compound in a high selectivity without causing the lowering of the activity of a catalyst during the reaction by reacting ethylene glycol in the co-existence of the specific complex catalyst and a slight amount of molecular O2. CONSTITUTION:Ethylene glycol is reacted in the presence of a complex catalyst such as a Cu-Zn catalyst comprising the copper in an amount of 1 pt.wt. converted into copper oxide and any other inorganic component such as the zinc in an amount of 0.3-3 pts.wt. converted into zinc oxide and also in the presence of molecular O2 in an amount of 0.001-0.3mol per mol of the ethylene glycol and water in an amount of usually 1-100mol per mol of the compound preferably at 100-400 deg.C at a LHSU of 0.05-20/hr under the normal pressure to provide the subject compound useful as a raw material for amino acids, medicines, agricultural chemicals, photographic chemicals or specific polymers or as a fiber-treating agent, etc., in a continuous operation state over a long period without requiring the exchange of the catalyst and the re-activation of the catalyst.

3. 发明专利

JPS61277664A METHOD FOR STABILIZING AZIRIDINE-2-CARBOXAMIDE 失效
公开(公告)号：JPS61277664A
公开(公告)日：1986-12-08
申请号：JP11781885
申请日：1985-05-31
申请人： LIGHT OIL UTILIZATION RES ASS
发明人： KITAGAWA SADAO , MINAFUJI MITSUMASA , YOKOI TAKASHI
IPC分类号： C07D203/08
摘要： PURPOSE:To prevent the deterioration in storage and transportation in a large amount or for long period, by adding a stabilizer selected form alkali (earth) metal hydroxides, etc., ammonia and organic amines to aziridine-2-carboxamide in the solid state. CONSTITUTION:A stabilizer consisting of a base is added to aziridine-2-car boxamide (A) in the solid state to allow the compound (A) in a more basic atmosphere than the basicity thereof. Thus, the compound (A) is stabilized. The above-mentioned stabilizer is selected from hydroxides, carbonates, phosphates, etc. of alkali (earth) metals, ammonia and organic amines, and ammonia and tertiary amines are preferred. The stabilizer is added by adding a solution thereof to a solvent, in which the stabilizer compound is soluble and the compound (A) is insoluble, or introducing gaseous ammonia into a container containing the compound (A). USE:An antitumor agent, intermediate for agricultural chemicals, raw material for functional resins, etc.

4. 发明专利

JPS61277663A METHOD FOR STABILIZING AZIRIDINE-2-CARBOXAMIDE 失效
公开(公告)号：JPS61277663A
公开(公告)日：1986-12-08
申请号：JP11781785
申请日：1985-05-31
申请人： LIGHT OIL UTILIZATION RES ASS
发明人： KITAGAWA SADAO , MINAFUJI MITSUMASA , YOKOI TAKASHI
IPC分类号： C07D203/08
摘要： PURPOSE:To stabilize aziridine-2-carboxamide, by adding a stabilizer selected from alkali (earth) metal hydroxides, ammonia and organic amines to a solution containing the aziridine-2-carboxamide having an ammonia concentration of a specific value or below. CONSTITUTION:A stabilizer consisting of a base is added to a solution con taining aziridine-2-carboxamide (A) having

5. 发明专利

JPH02288851A SEPARATION AND PURIFICATION OF DL-SERINE 失效
公开(公告)号：JPH02288851A
公开(公告)日：1990-11-28
申请号：JP1971790
申请日：1990-01-30
申请人： LIGHT OIL UTILIZATION RES ASS
发明人： KUJIRA KATSUFUMI , YOKOI TAKASHI , ODAGIRI MASAKI , IMANARI MAKOTO
IPC分类号： C07C227/40 , C07C229/22
摘要： PURPOSE:To advantageously separate and purify DL-serine by hydrolysis of a product of the (oxidative) dehydrogenation-Strecker reaction of ethylene glycol followed by ion-exclusion chromatography twice with a neutralization interposed therein using a strong-acidity cation exchange resin. CONSTITUTION:A reaction liquid containing glycolaldehyde formed by dehydrogenation or oxidative dehydrogenation of ethylene glycol is directly put to Strecker reaction without the separation and purification of said intermediate difficult in such separation and purification, and the resulting reaction product is hydrolyzed with a strong base, and then ammonia is recovered from an aqueous solution containing the resultant DL-serine alkali salt. Thence, the above- mentioned aqueous solution is put to ion-exclusion chromatography using a strong-acidity cation exchange resin, and the resulting DL-serine fraction is neutralized to ca. the isoelectric point of serine followed by ion-exclusion chromatography again to simply eliminate unreacted raw materials and/or inorganic salts contained, thus industrially obtaining at a low cost high-purity DL-serine useful for amino acid infusion solutions, etc.

6. 发明专利

JPS63233959A CONCENTRATION OF AROMATIC AMINO ACID 失效
公开(公告)号：JPS63233959A
公开(公告)日：1988-09-29
申请号：JP6558587
申请日：1987-03-23
申请人： LIGHT OIL UTILIZATION RES ASS
发明人： HOYA TAKAO , YOKOI TAKASHI
IPC分类号： C07D209/20 , C07C67/00 , C07C227/00 , C07C227/28 , C07C227/40 , C07C229/36
摘要： PURPOSE:To concentrate the titled amino acid without requiring a lot of energy, by adsorbing an aromatic amino acid in an aqueous solution on a non-ion exchange high porous polymer resin and passing a mixed solution of a compound trialkylamine, etc., through the resin. CONSTITUTION:An aromatic amino acid (e.g. tryptophan) in an aqueous solution is adsorbed on a non-ion exchange high porous polymer resin, a mixed solution of water and a trialkylamine and/or N-alkylpiperidine showing properties of water solubility changing with temperature from slightly soluble to readily soluble is passed through the resin at = a temperature wherein the solution is separated into two layers, the aromatic amino acid is concentrated in a layer solution of the lower layer comprising water as a main compound and obtained. This method can be carried out without requiring a lot of energy and an auxiliary.

7. 发明专利

JPH02204474A SEPARATION AND PURIFICATION OF DL-SERINE 失效
公开(公告)号：JPH02204474A
公开(公告)日：1990-08-14
申请号：JP2551889
申请日：1989-02-03
申请人： LIGHT OIL UTILIZATION RES ASS
发明人： KUJIRA KATSUFUMI , YOKOI TAKASHI , ODAGIRI MASAKI , IMANARI MAKOTO
IPC分类号： G01N30/88 , B01D15/08 , C07C227/40 , C07C229/22
摘要： PURPOSE:To profitably provide the subject substance having a high purity by inexpensively preparing glycolaldehyde from ethylene glycol as a starting material, subjecting the glycolaldehyde to a Strecker reaction and to a hydrolysis reaction as such without being isolated and subsequently subjected the crude product to a separation, purification process using active carbon. CONSTITUTION:Ethylene glycol as a raw material is subjected to a dehydrogenation or oxidative hydrogenation reaction to give a reaction solution containing glycolaldehyde. The reaction solution as such is subjected to a Strecker reaction using a cyano compound, ammonium chloride and ammonia. The reaction solution is subjected to a hydrolysis reaction using an acid or alkali to give a crude serine aqueous solution. The aqueous solution is subjected to a liquid chromatography to separate and recover ethylene glycol. The active carbon- treated aqueous solution is preferably subjected to an ion-removing chromatography using a strong acidic cation exchange resin for the separation of inorganic salts to provide the objective compound.

8. 发明专利

JPS62192354A PRODUCTION OF AZIRIDINE-2-CARBOXAMIDE 失效
公开(公告)号：JPS62192354A
公开(公告)日：1987-08-22
申请号：JP3584486
申请日：1986-02-20
申请人： LIGHT OIL UTILIZATION RES ASS
发明人： KITAGAWA SADAO , YOKOI TAKASHI , MINAFUJI MITSUMASA
IPC分类号： C07D203/08
摘要： PURPOSE:To obtain the titled compound useful as an intermediate for pharmaceuticals, agricultural chemicals, etc., in high yield and short time, by using a specific 2,3-dihalopropionic acid derivative, etc., as raw material and reacting the material with NH3 in the presence of an alkali metal or alkaline earth metal hydroxide. CONSTITUTION:The objective compound having physiological activity such as antitumor activity can be produced by reacting (A) a 2,3-dihalopropionic acid derivative of formula I (X is halogen; Y is 1-10C alkoxycarbonyl, carbamoyl or cyano) easily producible by the halogen addition reaction of an acrylic acid ester, acrylamide and acrylonitrile or a haloacrylic acid derivative of formula II produced by the reaction of the above halogen-addition product and an alkali, etc., with (B) NH3 in a solvent in the presence of an alkali metal or alkaline earth metal hydroxide such as Ca(OH)2 at 0-200 deg.C for 5sec-48hr. EFFECT:The process is remarkably improved from the viewpoints of raw material and cost and has industrial advantage. USE:Intermediate for alpha-amino acid, etc.

9. 发明专利

JPS61186361A PRODUCTION OF AZIRIDINE-2-CARBOXYLIC ACID CALCIUM SALT 失效
公开(公告)号：JPS61186361A
公开(公告)日：1986-08-20
申请号：JP2577585
申请日：1985-02-13
申请人： LIGHT OIL UTILIZATION RES ASS
发明人： KITAGAWA SADAO , YOKOI TAKASHI , MINAFUJI MITSUMASA
IPC分类号： C07D203/08
摘要： PURPOSE:To obtain the titled compound in high yield, with single reaction operation, from 2,3-dihalopropionic acid derivative or alpha-haloacrylic acid derivative, by reacting the above derivative with ammonia in an aqueous medium in the presence of calcium hydroxide. CONSTITUTION:The objective aziridine-2-carboxylic acid calcium salt useful as an intermediate for pharmaceuticals, agricultural chemicals, and alpha-amino acids such as serine, economically with simple operation reaction, by reacting a 2,3-dihalopropionic acid derivative of formula I (X is F, Cl, Br or I, especially Cl; Y is CO2R , CONR 2 or CN; R is 1-10C hydrocarbon residue; R is H or 1-10C hydrocarbon residue) or an alpha-haloacrylic acid derivative of formula II with ammonia in water or in a mixture of water and an organic solvent (preferably methanol, ethanol, i-propanol, etc.), preferably in water, in the presence of calcium hydroxide.

10. 发明专利

JPS61186360A PRODUCTION OF AZIRIDINE-2-CARBOXYLIC ACID SALT 失效
公开(公告)号：JPS61186360A
公开(公告)日：1986-08-20
申请号：JP2577385
申请日：1985-02-13
申请人： LIGHT OIL UTILIZATION RES ASS
发明人： KITAGAWA SADAO , YOKOI TAKASHI , MINAFUJI MITSUMASA
IPC分类号： C07D203/08
摘要： PURPOSE:To obtain the titled compound useful as an intermediate for pharmaceuticals, etc. and free from halogen ions, easily in high yield, by reacting aziridine-2-carboxylic acid amide with an alkali metal or alkaline earth metal hydroxide in an aqueous medium. CONSTITUTION:An aziridine-2-carboxylic acid salt useful also as an inter-mediate for agricultural chemicals and alpha-amino acids can be produced economically on an industrial scale, by reacting aziridine-2-carboxylic acid amide with an alkali metal or alkaline earth metal hydroxide (preferably hydroxide of lithium, sodium, potassium or calcium, especially calcium) in water or in a mixture of water and an organic solvent (preferably methanol, ethanol, i-propanol, etc.). Since the compound is essentially free from halogen ions, it can be used for the production of serine, etc. without necessitating the troublesome operations for the removal of halgen ions.

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