公开(公告)号：JPS6391351A

公开(公告)日：1988-04-22

申请号：JP23635086

申请日：1986-10-06

Applicant: MITSUI PETROCHEMICAL IND

Inventor： TAKAHATA KAZUNORI ,  MURASHIGE TOSHIHIRO ,  HIROKANE SHINYA

IPC: C07B61/00 ,  B01J23/86 ,  C07C67/00 ,  C07C209/00 ,  C07C209/18 ,  C07C211/52

Abstract: PURPOSE:To obtain the titled compound useful as an intermediate for producing drugs, agricultural chemicals, etc., selectively and in high yield, by reacting a specific aromatic amine with a primary or secondary alcohol in the presence of an iron oxide catalyst containing copper oxide and chromium oxide. CONSTITUTION:An aromatic amine (e.g. aniline, o-tiluidine, p-tiluidine, etc.) containing at least one H in the amino group is reacted with a primary alcohol (e.g. methanol, ethanol, n-propanol, etc.) or a secondary alcohol (e.g. isopropanol, sec-butyl alcohol, etc.) in the presence of an iron oxide catalyst containing copper oxide and chromium oxide to give an N-alkylated aromatic amine. The catalyst is obtained by a method of calcining a mixture of metallic compounds capable of becoming iron oxide, copper oxide and chromium oxide, a method of completely drying the aqueous solution of the mixture and calcining, etc.

公开(公告)号：JPH0940639A

公开(公告)日：1997-02-10

申请号：JP3356096

申请日：1996-02-21

Applicant: MITSUI PETROCHEMICAL IND

Inventor： MATSUI NARIKAZU ,  FUJITA TERUNORI ,  TAKAI TOSHIHIRO ,  MATSUOKA HIDETO ,  KAGAYAMA AKISHI ,  KURODA HIROSHI ,  HIROKANE SHINYA

IPC: C07D239/42 ,  B01J31/22 ,  C07B61/00 ,  C07C211/14 ,  C07C229/16 ,  C07C229/76 ,  C07C255/24 ,  C07C311/18 ,  C07C407/00 ,  C07C409/10 ,  C07D213/38 ,  C07D213/74 ,  C07D213/81 ,  C07D215/40 ,  C07D241/20 ,  C07D401/04 ,  C07D401/12 ,  C07F1/08 ,  C07F7/00 ,  C07F7/28 ,  C07F11/00 ,  C07F13/00 ,  C07F15/00 ,  C07F15/02 ,  C07F15/04 ,  C07F15/06

Abstract: PROBLEM TO BE SOLVED: To produce an arylalkyl hydroperoxide selectively, in high conversion and in high concentration by oxidizing an arylalkylhydrocarbon with an oxygen- containing gas in the presence of a transition metal complex having a specific compound as a ligand as a catalyst. SOLUTION: This production of an arylalkyl hydroperoxide is to oxidize (A) an arylalkylhydrocarbon of formula II [P and Q are each H, an alkyl, etc.; (x) is 1-3 integer; Ar is an aromatic hydrocarbon having (x) valency] with (B) an oxygen-containing gas in the presence of a transition metal complex catalyst of formula I [A is independently a 1-6C alkylene, o-phenylene, 1,8- naphthylene, etc.; K to K are independently H, an alkyl, an aryl, pyridyl, etc.; M is a transition metal ion having +(a) valency as the central metal ion; X is a counter ion having -(b) valency and stable against oxidation; (a) is 1-4 integer; (b) is a positive integer; (n) is 1-4 integer, (n)=(a)/(b); (m) is an integer not less than 2] and convert reaction product into the corresponding arylalkyl hydroperoxide.

公开(公告)号：JPH01221339A

公开(公告)日：1989-09-04

申请号：JP4647588

申请日：1988-02-29

Applicant: MITSUI PETROCHEMICAL IND

Inventor： HIROKANE SHINYA ,  ONO HIROYASU ,  YOROZU KIYOTAKA ,  TANIGUCHI KATSUO

IPC: C07C37/08 ,  C07B61/00 ,  C07C27/00 ,  C07C39/08 ,  C07C39/14 ,  C07C67/00

Abstract: PURPOSE:To obtain the subject compound in one step at a low cost, by reacting an aromatic hydrocarbon containing alpha,alpha-hydrocarbon group-alpha-hydroxymethyl group in the presence of a solvent, an acid and hydrogen peroxide, wherein the acid is a combination of a heteropolyacid and a protonic acid. CONSTITUTION:A hydroxy-aromatic hydrocarbon is produced by reacting a compound of formula I (Ar is aryl; R and R are H or hydrocarbon group; m is 0, 1 or 2; n is 1, 2 or 3; R s and R s in n+m groups of formula II and formula III may be different from each other), carbinol (m=0) and/or carbinol hydroperoxide (m=1-2) in the presence of a solvent, an acid and hydrogen peroxide. In the above process, a mixture of a heteropolyacid and a protonic acid is used as the acid component. The oxidation reaction and the acid decomposition reaction can be performed in one step and the objective compound can be obtained in high selectivity and yield by this process.

公开(公告)号：JPS6330437A

公开(公告)日：1988-02-09

申请号：JP17510286

申请日：1986-07-25

Applicant: MITSUI PETROCHEMICAL IND

Inventor： MIKI HISAYA ,  TAGUCHI TORU ,  HIROKANE SHINYA

IPC: C07B61/00 ,  C07C27/00 ,  C07C29/132 ,  C07C37/08 ,  C07C39/12 ,  C07C39/14 ,  C07C67/00 ,  C07C69/16 ,  C07C409/12

Abstract: PURPOSE:Diisopropylnaphthalene is oxidized with O2 in the presence of a base and the product is subjected to acidolysis, allowed to react with an acyloxylating agent whereby the title compound of high purity, which is used as a starting material for liquid crystal polymers, is obtained in high yield. CONSTITUTION:Diisopropylnaphthalene is oxidized molecular oxygen in the presence of a base to give an oxidation product containing Diisopropylnaphthalene hydroperoxide. The product is subjected to acidolysis, an acyloxylating agent such as acetic anhydride is allowed to react with the acidolysis reaction mixture containing dihydroxynaphthalene in the presence of a catalyst. Diacyloxynaphthalene is separated from the reaction mixture.

公开(公告)号：JPS61238766A

公开(公告)日：1986-10-24

申请号：JP8105885

申请日：1985-04-16

Applicant: MITSUI PETROCHEMICAL IND

Inventor： TAKAHATA KAZUNORI ,  MURASHIGE TOSHIHIRO ,  HIROKANE SHINYA

IPC: C07B61/00 ,  B01J23/00 ,  B01J23/26 ,  B01J23/34 ,  B01J23/74 ,  B01J23/745 ,  B01J23/825 ,  B01J23/835 ,  B01J23/86 ,  C07C67/00 ,  C07C209/00 ,  C07C209/68 ,  C07C211/43 ,  C07C211/45 ,  C07C211/46 ,  C07C211/47 ,  C07C211/57

Abstract: PURPOSE:To obtain the titled compound useful as a synthetic intermediate for agricultural chemicals, pharmaceuticals, dyes, resin stabilizer, etc., in high yield and selectivity, by reacting an aromatic amine having H at the ortho- position with a primary or secondary alcohol in the presence of a specific catalyst under heating. CONSTITUTION:The objective compound can be produced by reacting an aromatic amine having at least one H atom at the ortho-position (e.g. aniline, o-alkylaniline) with a primary or secondary alcohol (e.g. methanol, isopropanol, etc.) in the presence of a catalyst at 250-450 deg.C in vapor phase. The catalyst is the one containing transition metal oxide (e.g. a catalyst containing iron oxide, etc., as main component) and obtained by calcining a component composed mainly of a transition metal compound at 550-850 deg.C. It has improved durability and long life.

公开(公告)号：JPH0761982A

公开(公告)日：1995-03-07

申请号：JP21153993

申请日：1993-08-26

Applicant: MITSUI PETROCHEMICAL IND

Inventor： TSUKAMOTO KOJI ,  KATOU KOUJI ,  FUKUHARA HIROSHI ,  ISAYAMA SHIGERU ,  HIROKANE SHINYA ,  KUWABARA MASAHIRO

IPC: B01J27/188 ,  B01J27/19 ,  B01J27/195 ,  B01J27/198 ,  C07B61/00 ,  C07D307/33 ,  C07D309/30 ,  C07D313/04 ,  C07D313/18

Abstract: PURPOSE:To produce a lactone from a cyclic ketone in high yield and in high selectivity by using an inexpensive acetaldehyde. CONSTITUTION:In a method for producing a lactone by reacting a cyclic ketone with an oxygen containing gas in the presence of an aldehyde having >=2 carbon, a hetero polyacid or its salt is used as a catalyst.

公开(公告)号：JPH026841A

公开(公告)日：1990-01-11

申请号：JP15616488

申请日：1988-06-24

Applicant: MITSUI PETROCHEMICAL IND

Inventor： ONO HIROYASU ,  HIROKANE SHINYA ,  TANIGUCHI KATSUO

IPC: B01J19/00 ,  B01J19/24

Abstract: PURPOSE:To carry out an efficient continuous reaction by providing a partition preventing raw material or an intermediate product from being mixed with the product during the progressive state of reaction and forming an evaporation space allowing the evaporation of a solvent or a part of reaction liquid. CONSTITUTION:The partition 3 is provided so that the reaction liquid is flowed along the partition 8 in a continuous reaction vessel 1 in which a reaction is carried out under heating and refluxing. And, the evaporation space 4 is formed in the upper part of the vessel so that the reaction solvent or a part of the reaction liquid is allowed to evaporate from each part of the reaction liquid. The reaction is carried out while the reaction liquid is moved so that the raw material or the intermediate product supplied into the reaction vessel is not mixed with the product. One of the examples of this reaction is such a reaction that resorcinol is produced from the air oxidation product of m- diisopropyl benzene. As a result, the reaction is continuously and efficiently carried out while the reaction heat is removed without the reaction between raw material and the reacted product.

公开(公告)号：JPS63264540A

公开(公告)日：1988-11-01

申请号：JP9823987

申请日：1987-04-21

Applicant: MITSUI PETROCHEMICAL IND

Inventor： ISHIGURO MASAHARU ,  MIKI HISAYA ,  HIROKANE SHINYA ,  NITAHARA MASATOSHI ,  TAGUCHI TORU

IPC: C07C43/20 ,  C07B61/00 ,  C07C27/00 ,  C07C37/11 ,  C07C39/14 ,  C07C39/38 ,  C07C41/00 ,  C07C41/30 ,  C07C43/225 ,  C07C43/23 ,  C07C67/00 ,  C07C69/035

Abstract: PURPOSE:To produce the titled compound useful as a raw material for asymmetric polymer, additive for polymer production, etc., in high yield, by reacting naphthalenes in the presence of a peroxide and an acid and, if necessary, acylating the reaction product. CONSTITUTION:1,1'-Binaphthols of formula II (e.g. 2,2',6,6'-tetraphydroxy-1,1'- binaphthyl) can be produced by reacting naphthalenes of formula I (R is H or alkyl; R is H, hydroxy, alkyl, alkoxy or halogen) (e.g. 2,6-dihydroxynaph thalene) in the presence of a peroxide (e.g. hydrogen peroxide) and an acid (e.g. sulfuric acid) and, if necessary, reacting the product with an acylation agent (e.g. formic acid and acetic acid). The process can be performed without brominating a naphthalene compound as a raw material, using decreased amount of catalyst and preventing coloring of the product.

公开(公告)号：JPS61238767A

公开(公告)日：1986-10-24

申请号：JP8105985

申请日：1985-04-16

Applicant: MITSUI PETROCHEMICAL IND

Inventor： TAKAHATA KAZUNORI ,  MURASHIGE TOSHIHIRO ,  HIROKANE SHINYA

IPC: C07C211/46 ,  B01J23/86 ,  C07B61/00 ,  C07C67/00 ,  C07C209/00 ,  C07C209/68 ,  C07C211/45 ,  C07C211/47 ,  C07C211/57

Abstract: PURPOSE:To obtain the titled compound useful as a synthetic intermediate for agricultural chemicals, pharmaceuticals, dyes, resin stabilizers, etc., in high yield and selectivity, by reacting an aromatic amine having H at the ortho- position with a primary or secondary alcohol in the presence of a specific catalyst. CONSTITUTION:The objective compound can be produced by reacting an aromatic amine having at least one H atom at the ortho-position (e.g. aniline, o-alkylaniline) with a primary or secondary alcohol (e.g. methanol, isopropanol, etc.) in the presence of a catalyst at 250-450 deg.C in vapor phase. The catalyst is the one containing transition metal oxide (e.g. a catalyst containing iron oxide, etc., as main component) and obtained by calcining a component composed mainly of a transition metal compound, impregnating an aqueous solution of the salt of Cr, Al or Mg to the calcined product and again calcining the impregnated product. It has improved durability and long life.

公开(公告)号：JPH03148231A

公开(公告)日：1991-06-25

申请号：JP28543889

申请日：1989-11-01

Applicant: MITSUI PETROCHEMICAL IND

Inventor： ONO HIROYASU ,  HIROKANE SHINYA

IPC: B01J21/08 ,  B01J21/12 ,  B01J27/02 ,  B01J31/02 ,  C07B61/00 ,  C07C37/08 ,  C07C39/10

Abstract: PURPOSE:To continuously obtain the title substance in high yield by further oxidizing a reaction liquid obtained by subjecting an aromatic compound having alkyl group on an aromatic ring to air oxidation under neutral or basic conditions using H2O2, etc., and subjecting the oxidation product to acid decomposition. CONSTITUTION:An aromatic compound having 1-5 alkyl groups on an aromatic ring is subjected to air oxidation to give a carbinol group-containing compound and carbinolhydroperoxy group-containing compound, which are then brought into contact with hydrogen peroxide and an acid catalyst (e.g. sulfuric acid or benzenesulfonic acid) to provide the title substance. The contact of H2O2 with the acid catalyst is continuously carried out in twin reaction tanks arranged in series and simultaneously conditions in the first reaction tank are set so that carbinol group-containing compound may be preferentially converted into a carbinol hydroperoxy group-containing compound in a solvent such as nitriles, etc., and then subjected to acid decomposition in the second reaction tank to provide the aimed compound.