JPH0529384B2 - - Google Patents

Info

Publication number: JPH0529384B2
Authority: JP; Japan
Prior art keywords: reaction; oximes; solvent; catalyst; dmq
Prior art date: 1989-08-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP1217065A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0381249A (ja

Inventor

Katsuomi Takehira

Yoshito Watanabe

Masao Shimizu

Takashi Hayakawa

Hideo Orita

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

National Institute of Advanced Industrial Science and Technology AIST

Original Assignee

Agency of Industrial Science and Technology

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-08-23

Filing date

1989-08-23

Publication date

1993-04-30

1989-08-23 Application filed by Agency of Industrial Science and Technology filed Critical Agency of Industrial Science and Technology

1989-08-23 Priority to JP1217065A priority Critical patent/JPH0381249A/ja

1991-04-05 Publication of JPH0381249A publication Critical patent/JPH0381249A/ja

1993-04-30 Publication of JPH0529384B2 publication Critical patent/JPH0529384B2/ja

Status Granted legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 23
239000002904 solvent Substances 0.000 claims description 22
150000002923 oximes Chemical class 0.000 claims description 21
150000007522 mineralic acids Chemical class 0.000 claims description 20
-1 hydroxylamines Chemical class 0.000 claims description 17
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
239000005749 Copper compound Substances 0.000 claims description 14
150000001880 copper compounds Chemical class 0.000 claims description 14
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 13
150000002443 hydroxylamines Chemical class 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
229910017464 nitrogen compound Inorganic materials 0.000 claims description 9
150000002830 nitrogen compounds Chemical class 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 6
SENUUPBBLQWHMF-UHFFFAOYSA-N 2,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=C(C)C1=O SENUUPBBLQWHMF-UHFFFAOYSA-N 0.000 claims description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 42
238000000034 method Methods 0.000 description 16
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 10
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
239000000654 additive Substances 0.000 description 7
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
239000012046 mixed solvent Substances 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
229960003280 cupric chloride Drugs 0.000 description 5
229910001882 dioxygen Inorganic materials 0.000 description 5
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
239000007800 oxidant agent Substances 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
230000001590 oxidative effect Effects 0.000 description 4
JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000000996 additive effect Effects 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
150000004054 benzoquinones Chemical class 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
229920001002 functional polymer Polymers 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
239000002994 raw material Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
VTWKXBJHBHYJBI-SOFGYWHQSA-N (ne)-n-benzylidenehydroxylamine Chemical compound O\N=C\C1=CC=CC=C1 VTWKXBJHBHYJBI-SOFGYWHQSA-N 0.000 description 1
229940044613 1-propanol Drugs 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
229920000106 Liquid crystal polymer Polymers 0.000 description 1
239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 1
GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
238000005273 aeration Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
150000008365 aromatic ketones Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
229940045803 cuprous chloride Drugs 0.000 description 1
150000003997 cyclic ketones Chemical class 0.000 description 1
IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
125000005594 diketone group Chemical group 0.000 description 1
BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003925 fat Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229960001330 hydroxycarbamide Drugs 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
WHIVNJATOVLWBW-SNAWJCMRSA-N methylethyl ketone oxime Chemical compound CC\C(C)=N\O WHIVNJATOVLWBW-SNAWJCMRSA-N 0.000 description 1
VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
229940100595 phenylacetaldehyde Drugs 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920006380 polyphenylene oxide Polymers 0.000 description 1
CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP1217065A 1989-08-23 1989-08-23 ２，６―ジメチル―ｐ―ベンゾキノンの製造方法 Granted JPH0381249A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP1217065A JPH0381249A (ja)	1989-08-23	1989-08-23	２，６―ジメチル―ｐ―ベンゾキノンの製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP1217065A JPH0381249A (ja)	1989-08-23	1989-08-23	２，６―ジメチル―ｐ―ベンゾキノンの製造方法

Publications (2)

Publication Number	Publication Date
JPH0381249A JPH0381249A (ja)	1991-04-05
JPH0529384B2 true JPH0529384B2 (sk)	1993-04-30

Family

ID=16698284

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1217065A Granted JPH0381249A (ja)	1989-08-23	1989-08-23	２，６―ジメチル―ｐ―ベンゾキノンの製造方法

Country Status (1)

Country	Link
JP (1)	JPH0381249A (sk)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP3140273A1 (en) *	2014-05-09	2017-03-15	DSM IP Assets B.V.	Process for the production of 2,6-dimethylbenzoquinone

1989
- 1989-08-23 JP JP1217065A patent/JPH0381249A/ja active Granted

Also Published As

Publication number	Publication date
JPH0381249A (ja)	1991-04-05

Legal Events

Date	Code	Title	Description
2009-08-23	EXPY	Cancellation because of completion of term

Publication	Publication Date	Title
US6664423B2 (en)	2003-12-16	Two-phase ammoximation
US3932518A (en)	1976-01-13	Methylation of cyclohexanone with simultaneous dehydrogenation
JPH0451536B2 (sk)	1992-08-19
JPH0529384B2 (sk)	1993-04-30
KR100569560B1 (ko)	2006-04-10	히드록시디페닐아민으로부터 ｎ-페닐-벤조퀴논이민을제조하는 방법
JPS6049173B2 (ja)	1985-10-31	フエノ−ルの酸化法
JPH0529378B2 (sk)	1993-04-30
EP0369823B1 (en)	1993-06-16	Method for the preparation of 2,3,5-trimethylbenzoquinone
EP1027327B1 (en)	2003-09-03	Formation of quinonediimines from phenylenediamines by catalytic oxidation
JP4294209B2 (ja)	2009-07-08	オルト位アルキル化ヒドロキシ芳香族化合物の製造方法
JPH0529382B2 (sk)	1993-04-30
JPH02264739A (ja)	1990-10-29	２，３，５―トリメチルベンゾキノンの製造方法
JP3218044B2 (ja)	2001-10-15	シクロヘキサノールおよびシクロヘキサノンの製造方法
JPS61172851A (ja)	1986-08-04	オルソフタル酸エステルの酸化脱水素二量化法
EP0038708B1 (en)	1983-08-24	Process for producing benzophenone-azines
JP2000072737A (ja)	2000-03-07	オキシムの製造方法
JPH0477447A (ja)	1992-03-11	２，６―ジメチル―４―アルコキシメチルフェノール類の製造方法
JPS60332B2 (ja)	1985-01-07	シクロヘキサノンの製造方法
JP2000072738A (ja)	2000-03-07	オキシムの製造方法
JPS6042166B2 (ja)	1985-09-20	ベンゾフエノンイミン類からのアンモニアの回収方法
JPS6337781B2 (sk)	1988-07-27
JPH0529339B2 (sk)	1993-04-30
MXPA00006983A (en)	2002-03-26	Preparation of n-phenyl-benzoquinoneimine from hydroxydiphenylamines
JPH0142251B2 (sk)	1989-09-11
JP2000136164A (ja)	2000-05-16	ジカルボン酸のジエステルの製造方法