JPS6121215B2 - - Google Patents

Info

Publication number: JPS6121215B2
Authority: JP; Japan
Prior art keywords: ethylaniline; indole; catalyst; oxide; reaction
Prior art date: 1981-02-24
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

Application number

JP56025001A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57139064A (en

Inventor

Sukeishi Suyama

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.)

Resonac Holdings Corp

Original Assignee

Showa Denko KK

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.)

1981-02-24

Filing date

1981-02-24

Publication date

1986-05-26

1981-02-24 Application filed by Showa Denko KK filed Critical Showa Denko KK

1981-02-24 Priority to JP56025001A priority Critical patent/JPS57139064A/ja

1982-08-27 Publication of JPS57139064A publication Critical patent/JPS57139064A/ja

1986-05-26 Publication of JPS6121215B2 publication Critical patent/JPS6121215B2/ja

Status Granted legal-status Critical Current

Links

MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 claims description 48
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 40
239000003054 catalyst Substances 0.000 claims description 23
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 20
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 20
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
229910001882 dioxygen Inorganic materials 0.000 claims description 8
239000007789 gas Substances 0.000 claims description 8
239000000203 mixture Chemical class 0.000 claims description 6
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 6
239000010937 tungsten Substances 0.000 claims description 6
229910052721 tungsten Inorganic materials 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 3
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 description 13
238000000034 method Methods 0.000 description 11
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
229910001930 tungsten oxide Inorganic materials 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
238000001354 calcination Methods 0.000 description 2
-1 copper-barium chromate-chromium Chemical compound 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
229910052748 manganese Inorganic materials 0.000 description 2
239000011572 manganese Substances 0.000 description 2
PPNAOCWZXJOHFK-UHFFFAOYSA-N manganese(2+);oxygen(2-) Chemical class [O-2].[Mn+2] PPNAOCWZXJOHFK-UHFFFAOYSA-N 0.000 description 2
229910052750 molybdenum Inorganic materials 0.000 description 2
239000011733 molybdenum Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-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
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
WZECUPJJEIXUKY-UHFFFAOYSA-N [O-2].[O-2].[O-2].[U+6] Chemical compound [O-2].[O-2].[O-2].[U+6] WZECUPJJEIXUKY-UHFFFAOYSA-N 0.000 description 1
150000001339 alkali metal compounds Chemical class 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
229910000410 antimony oxide Inorganic materials 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
229910000416 bismuth oxide Inorganic materials 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
KYYSIVCCYWZZLR-UHFFFAOYSA-N cobalt(2+);dioxido(dioxo)molybdenum Chemical compound [Co+2].[O-][Mo]([O-])(=O)=O KYYSIVCCYWZZLR-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
XAYGUHUYDMLJJV-UHFFFAOYSA-Z decaazanium;dioxido(dioxo)tungsten;hydron;trioxotungsten Chemical compound [H+].[H+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O XAYGUHUYDMLJJV-UHFFFAOYSA-Z 0.000 description 1
TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 1
CRLHSBRULQUYOK-UHFFFAOYSA-N dioxido(dioxo)tungsten;manganese(2+) Chemical compound [Mn+2].[O-][W]([O-])(=O)=O CRLHSBRULQUYOK-UHFFFAOYSA-N 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
235000020776 essential amino acid Nutrition 0.000 description 1
239000003797 essential amino acid Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
230000014509 gene expression Effects 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
239000001307 helium Substances 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
229910000476 molybdenum oxide Inorganic materials 0.000 description 1
VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000002304 perfume Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
229910000439 uranium oxide Inorganic materials 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
229910001935 vanadium oxide Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000010457 zeolite Substances 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

Indole Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP56025001A 1981-02-24 1981-02-24 Preparation of indole Granted JPS57139064A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP56025001A JPS57139064A (en)	1981-02-24	1981-02-24	Preparation of indole

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP56025001A JPS57139064A (en)	1981-02-24	1981-02-24	Preparation of indole

Publications (2)

Publication Number	Publication Date
JPS57139064A JPS57139064A (en)	1982-08-27
JPS6121215B2 true JPS6121215B2 (de)	1986-05-26

Family

ID=12153720

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP56025001A Granted JPS57139064A (en)	1981-02-24	1981-02-24	Preparation of indole

Country Status (1)

Country	Link
JP (1)	JPS57139064A (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date
JPS61124777U (de) *	1985-01-25	1986-08-06
JPS62201315U (de) *	1986-06-11	1987-12-22
JPS632011U (de) *	1986-06-19	1988-01-08
JPH0429302Y2 (de) *	1986-05-02	1992-07-16

1981
- 1981-02-24 JP JP56025001A patent/JPS57139064A/ja active Granted

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date
JPS61124777U (de) *	1985-01-25	1986-08-06
JPH0429302Y2 (de) *	1986-05-02	1992-07-16
JPS62201315U (de) *	1986-06-11	1987-12-22
JPS632011U (de) *	1986-06-19	1988-01-08

Also Published As

Publication number	Publication date
JPS57139064A (en)	1982-08-27

Publication	Publication Date	Title
US6143928A (en)	2000-11-07	Catalysts for low temperature selective oxidation of propylene, methods of making and using the same
US3972920A (en)	1976-08-03	Process for producing unsaturated aldehydes, unsaturated fatty acids or conjugated dienes
CA2411000C (en)	2006-11-14	Process for the production of vinyl acetate
RU2198869C2 (ru)	2003-02-20	Способ селективного получения уксусной кислоты и используемый катализатор
US4816603A (en)	1989-03-28	Process for the production of methacrolein and methacrylic acid
US4155938A (en)	1979-05-22	Oxidation of olefins
JP4377051B2 (ja)	2009-12-02	エタンを接触酸化する酢酸の選択的製造方法
US4052450A (en)	1977-10-04	Catalytic oxidation of α-olefins
RU2036888C1 (ru)	1995-06-09	Способ получения этилена и/или уксусной кислоты и каталитическая композиция для его осуществления
CA1095076A (en)	1981-02-03	Process for the catalytic gas phase oxidation of toluene with a gas containing molecular oxygen
US4025565A (en)	1977-05-24	Process for preparing unsaturated aldehyde having three to four carbon atoms
JPH03238051A (ja)	1991-10-23	メタクリル酸製造用触媒の調製法
US3200081A (en)	1965-08-10	Mixed antimony oxide-manganese oxide oxidation catalyst
US4218572A (en)	1980-08-19	Process for the production of polyphenyls
US4541964A (en)	1985-09-17	Production of methacrylonitrile
JPH0242033A (ja)	1990-02-13	メタクリル酸および／またはメタクロレインの製造方法
UA67799C2 (uk)	2004-07-15	Способи одержання оцтової кислоти та вінілацетату
JPS6121215B2 (de)	1986-05-26
US3904653A (en)	1975-09-09	Synthesis of maleic anhydride
US3287394A (en)	1966-11-22	Catalytic synthesis of unsaturated nitriles
US3742079A (en)	1973-06-26	Oxidative dehydrogenation of ethylbenzene to styrene using a gold on titania catalyst
US3933686A (en)	1976-01-20	Catalyst for the production of acrylonitrile, acrylic acid and acrolein
US4523016A (en)	1985-06-11	Process for the catalytic dehydrogenation of piperidine
JPH0479697B2 (de)	1992-12-16
JP2631866B2 (ja)	1997-07-16	ピリミジン類の製造法

JPS6121215B2 - - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=12153720

Family Applications (1)

Country Status (1)

Cited By (4)

Cited By (4)

Also Published As

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