公开(公告)号：JPH11315036A

公开(公告)日：1999-11-16

申请号：JP9999698

申请日：1998-03-26

Applicant: DAICEL CHEM ,  ISHII YASUTAKA

Inventor： ISHII YASUTAKA ,  NAKANO TATSUYA

IPC: C07D307/33 ,  B01J31/02 ,  C07B41/06 ,  C07B41/12 ,  C07B61/00 ,  C07C27/00 ,  C07C45/29 ,  C07C47/12 ,  C07C47/52

Abstract: PROBLEM TO BE SOLVED: To obtain the corresponding acetal compound or carbonyl compound in high yield by reaction between an ether and nitrogen monoxide in the presence of an oxidative catalyst consisting of an imide compound. SOLUTION: This acetal compound of formula II or carbonyl compound of the formula: R CR O is obtained by reaction, in the presence of (A) an oxidative catalyst consisting of an imide compound of formula I (R and R are each H, a halogen, alkyl or the like; X is O or hydroxyl; (n) is 1-3) (e.g. N-hydroxyphthalimide), between (B) an ether of the formula: R CR HOR (R and R are each H, a hydrocarbon or the like; R is a hydrocarbon or heterocyclic ring) (e.g. dimethyl ether) and (C) nitrogen monoxide, e.g. at 0-300 deg.C for 30 min to 48 h; wherein it is preferable that the molar ratios A/B and C/B are 0.01-1 and >=0.5, respectively.

公开(公告)号：JPH11300212A

公开(公告)日：1999-11-02

申请号：JP10046098

申请日：1998-03-27

Applicant: DAICEL CHEM ,  ISHII YASUTAKA

Inventor： ISHII YASUTAKA ,  NAKANO TATSUYA

IPC: B01J31/02 ,  C07B61/00 ,  C07C45/33 ,  C07C45/36 ,  C07C49/453 ,  C07C49/67 ,  C07C49/675

Abstract: PROBLEM TO BE SOLVED: To generate an oxidation product in a high selectivity by oxidizing a substrate to be oxidized having a carbon-hydrogen bonding at a site adjacent to an unsaturated bonding to be oxidized in a high conversion rate in an oxygen atmosphere at a normal pressure by a method wherein an oxidation catalytic system composed of a specifically structured imide compound and a specific organic salt is used. SOLUTION: In the case where an oxidation catalyst useful in preparation of alcohols, carboxylic acids, or the like is prepared, an organic salt composed of an imide compound expressed by the formula (wherein, R , R are same or different, and are each hydrogen, a halogen, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group or the like; and R , R may from a double bond, or an aromatic or nonaromatic ring by being linked to each other; X indicates an oxygen atom or hydroxyl group, and (n) indicates an integer of 1 to 3), a polyatomic cation or a polyatomic anion including periodic table group 15 or group 16 elements wherein at least one organic group is bonded, and a counterion, is used.

公开(公告)号：JPH11226418A

公开(公告)日：1999-08-24

申请号：JP4887998

申请日：1998-02-13

Applicant: DAICEL CHEM ,  ISHII YASUTAKA

Inventor： ISHII YASUTAKA

IPC: B01J27/199 ,  B01J31/36 ,  C07B41/06 ,  C07B61/00 ,  C07C45/34 ,  C07C49/395 ,  C07C67/055 ,  C07C69/16

Abstract: PROBLEM TO BE SOLVED: To obtain an oxidation catalyst capable of efficiently oxidizing an org. material. SOLUTION: The oxidation catalyst comprises a divalent palladium compd. (A) and a heteropolyacid or its salt (B) and at least one of the catalyst components has been carried on activated carbon having 0-0.15 wt.% sulfur content. Palladium (II) acetate may be used as the divalent palladium compd. A. The heteropolyacid or its salt B is, e.g. a phosphovanadomolybdate. When an alkene or cycloalkene is oxidized with molecular oxygen in the presence of the oxidation catalyst, the corresponding ketone is obtd. in a high yield.

公开(公告)号：JPH11226416A

公开(公告)日：1999-08-24

申请号：JP5444498

申请日：1998-02-18

Applicant: DAICEL CHEM ,  ISHII YASUTAKA

Inventor： ISHII YASUTAKA ,  NAKANO TATSUYA

IPC: B01J31/02 ,  C07B33/00 ,  C07B61/00 ,  C07C46/04 ,  C07C50/18 ,  C07C315/02 ,  C07C317/14

Abstract: PROBLEM TO BE SOLVED: To form an objective oxidation product with a high selectivity by using an oxidation catalyst system consisting of a specified imide compd. and a prim. or sec. alcohol. SOLUTION: The oxidation catalyst system consists of an imide compd. of the formula and a prim. or sec. alcohol as a co-oxidizing agent. In the formula, R and R are mutually the same or different and are each H, a halogen, alkyl, aryl, cycloalkyl, hydroxyl, alkoxy, carboxyl or acyl, R and R may bond to each other to form a double bond or an arom. or nonarom. ring, X is O or hydroxyl and (n) is an integer of 1-3.

公开(公告)号：JPH11180913A

公开(公告)日：1999-07-06

申请号：JP35339797

申请日：1997-12-22

Applicant: DAICEL CHEM

Inventor： NAKANO TATSUYA ,  ISHII YASUTAKA

IPC: B01J31/04 ,  B01J31/22 ,  C07B61/00 ,  C07C27/12 ,  C07C29/50 ,  C07C33/20 ,  C07C33/22 ,  C07C45/36 ,  C07C47/54 ,  C07C49/76 ,  C07C49/78 ,  C07C51/265 ,  C07C63/06

Abstract: PROBLEM TO BE SOLVED: To obtain an oxide corresponding to a substrate by efficiently oxidizing an aromatic compound having methyl group or methylene group under mild conditions. SOLUTION: An aromatic compound having methyl group or methylene group is oxidized with oxygen in the presence of an oxidation catalyst system composed of an imide compound represented by the formula [R and R denote each a substituent group such as hydrogen atom or a halogen atom; R and R together may mutually be bound to form a double bond, an aromatic or a nonaromatic 5- to 12-membered ring; X denotes O or OH; (n) is 1-3] (N- hydroxyphthalimide or the like) and a cocatalyst containing an element selected from the group consisting of a group 2A of the periodic table, a transition metal (groups 3A to 7A, 8, 1B and 2B of the periodic table) and a group 3B of the periodic table and at least one reactional promoter selected from carboxylic acids or salts thereof and aldehydes to afford an oxide (ketones, alcohols, aldehydes, carboxylic acids or the like).

公开(公告)号：JPH11147870A

公开(公告)日：1999-06-02

申请号：JP3177198

申请日：1998-02-13

Applicant: DAICEL CHEM ,  ISHII YASUTAKA

Inventor： ISHII YASUTAKA ,  NAKANO TATSUYA

IPC: C07D207/323 ,  B01J27/08 ,  B01J31/12 ,  C07B61/00 ,  C07C249/02 ,  C07C251/10

Abstract: PROBLEM TO BE SOLVED: To easily obtain the subject compounds useful as an intermediate for producing physiologically active substances and the like in a good yield by reacting a specific imine compound with a carbonyl compound in the presence of a specific catalyst. SOLUTION: (A) An imine compound of formula I (R to R are each a non-reactive atom or organic group) (for example, N-butylidene-s-butylamine) is reacted with (B) a carbonyl compound of the formula: R CH2 COR (R and R are each a non-reactive atom or organic group) (for example, propionaldehyde) in the presence of (C) a catalyst comprising a compound of the group III element in the periodic table) [for example, scandium (III) trifluoromethanesulfonate] usually in an organic solvent such as terahydrofuran preferably at a temp. about 10 to 50 deg.C to obtain an α,β-unsaturated imine compound of formula II or III [for example, N-(2-methyl-2-hexylidene)-s-butylamine].

公开(公告)号：JPH1180080A

公开(公告)日：1999-03-23

申请号：JP24796797

申请日：1997-09-12

Applicant: DAICEL CHEM ,  ISHII YASUTAKA

Inventor： ISHII YASUTAKA ,  NAKANO TATSUYA

IPC: B01J31/22 ,  C07B61/00 ,  C07C67/20 ,  C07C67/29 ,  C07C67/293 ,  C07C67/44 ,  C07C69/16 ,  C07C69/28 ,  C07C69/44 ,  C07C69/75

Abstract: PROBLEM TO BE SOLVED: To obtain the subject compound that is useful as an intermediate for solvents, surfactants, monomers, medicines and agrochemicals by allowing a dicarboxylic divinyl ester to react with an aldehyde in the presence of a metal catalyst. SOLUTION: In the presence of a metal catalyst such as an element in group 2A or a transition metal element in the periodic table, preferably in an amount of 0.05-0.2 mol, 1 mole of a dicarboxylic divinyl ester of formula I (A is a divalent organic group; R -R are each H, a 1-5 alkyl) is allowed to react with 1.5-15 moles of an aldehyde of formula II (R and R are each a non reactive atom, a on-reactive tetrachloride at 10-40 deg.C to prepare a glycol ester derivative of formula III ((m) is 0, 1; (n) is 1, 2; R is a group represented by formula IV or formula V). After completion of the reaction, the product is separated and purified by filtration, concentration, extraction, crystallization, recrystallization, column chromatography and the like.

公开(公告)号：JPH10316610A

公开(公告)日：1998-12-02

申请号：JP12252697

申请日：1997-05-13

Applicant: DAICEL CHEM ,  ISHII YASUTAKA

Inventor： ISHII YASUTAKA ,  NAKANO TATSUYA

IPC: C07D307/89 ,  B01J31/02 ,  B01J31/22 ,  C07B61/00 ,  C07C51/23 ,  C07C51/31 ,  C07C51/54 ,  C07C55/12 ,  C07C67/39 ,  C07C69/24 ,  C07C69/78 ,  C07D201/08 ,  C07D309/30 ,  C07D311/76 ,  C07D311/86 ,  C07D313/04 ,  C07D315/00

Abstract: PROBLEM TO BE SOLVED: To directly and efficiently produce a corresponding oxide (ester or acid anhydride) from an ether in high conversion and selectivity by bringing an ether into contact with oxygen in the presence of an oxidation catalyst constituted with a specific imide compound. SOLUTION: In the presence of an oxidation catalyst comprising an imide of the formula (R and R are each H, a halogen, an alkyl, an aryl, etc., R and R may link to each other to form a double bond or a ring; X is oxygen or hydroxyl; n is 1-3) or a mixture thereof with a cocatalyst (for example, an oxide, an organic acid salt, an inorganic acid salt, a halide, a complex and heteropolyacid of transition metal compound), an acyclic ether or a nonaromatic cyclic ether is brought into contact with oxygen in an organic solvent inactive to the reaction, at 0-300 deg.C, preferably 30-250 deg.C for 30 minutes to 48 hours, preferably for 2-24 hours to oxide the ether to the objective compound.

公开(公告)号：JPH10158209A

公开(公告)日：1998-06-16

申请号：JP31377796

申请日：1996-11-25

Applicant: DAICEL CHEM ,  ISHII YASUTAKA

Inventor： MATSUOKA KAZUYUKI ,  ISHII YASUTAKA

IPC: B01J27/199 ,  C07B61/00 ,  C07C45/34 ,  C07C49/757

Abstract: PROBLEM TO BE SOLVED: To obtain the subject compound suitable as an intermediate useful for medicine, perfume, seasoning and a polymer raw material in high yield industrially advantageously by using a specific catalyst and oxidizing a methylcycloalkenone. SOLUTION: A 3-methylcycloalkenone of formula II (Y is an aliphatic hydrocarbon group) (e.g. isophorone) is reacted with oxygen in the presence of a heteropolyacid, preferably a vanadomolybdophosphonic acid (salt) of formula I (A is one or more selected from H, NH4 , an alkali metal and an alkaline earth metal; (n) is 1-10, preferably 4-10) to give the objective compound of formula III (e.g. 5,5-dimethyl-3-formylcyclohexanone). Preferably, the heteropoly acid (salt) is supported on activated carbon of a carrier in the ratio of 0.1-100 pts.wt. to 100 pts.wt. of the carrier and used. The use of the catalyst can raise the yield of the compound from the 3-methylcycloalkenone from 15-25wt.% of references to 48-58wt.%.

公开(公告)号：JPH0987227A

公开(公告)日：1997-03-31

申请号：JP26909395

申请日：1995-09-22

Applicant: ISHII YASUTAKA ,  DAICEL CHEM

Inventor： ISHII YASUTAKA ,  ONO MITSURU ,  SHIBATA HIKARI

IPC: C07C45/29 ,  C07B61/00 ,  C07C49/17 ,  C07C49/213 ,  C07C49/417

Abstract: PROBLEM TO BE SOLVED: To provide a method for producing a ketone, capable of producing the ketone in high conversion and in high selectivity by oxidizing the corresponding secondary alcohol with bromic acid or its salt. SOLUTION: This method for producing a ketone comprises oxidizing the corresponding secondary alcohol with bromic acrid or its salt in an amount of 0.4-1 mole based on the hydroxyl group of the secondary alcohol under an acidic condition containing at least an inorganic acid selected from hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid or an organic acrid (e.g. an organic carboxylic acid). The secondary alcohol includes aliphatic alcohols and alicyclic alcohols, and may be a monovalent car polyvalent alcohol. In the reaction, bromine is produced together with the ketone.