JPS6337781B2 - - Google Patents

Info

Publication number: JPS6337781B2
Authority: JP; Japan
Prior art keywords: group; reaction; oxidizing agent; imine; benzophenone
Prior art date: 1979-11-05
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

JP14294479A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5665855A (en

Inventor

Tomya Itsushiki

Tetsuo Tomita

Shuzo Sakaguchi

Toshiaki Kanzaki

Osamu Aoki

Norio Takeda

Yoshuki Aoki

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.)

Mitsubishi Gas Chemical Co Inc

Original Assignee

Mitsubishi Gas Chemical Co Inc

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.)

1979-11-05

Filing date

1979-11-05

Publication date

1988-07-27

1979-11-05 Application filed by Mitsubishi Gas Chemical Co Inc filed Critical Mitsubishi Gas Chemical Co Inc

1979-11-05 Priority to JP14294479A priority Critical patent/JPS5665855A/ja

1981-06-03 Publication of JPS5665855A publication Critical patent/JPS5665855A/ja

1988-07-27 Publication of JPS6337781B2 publication Critical patent/JPS6337781B2/ja

Status Granted legal-status Critical Current

Links

239000007800 oxidant agent Substances 0.000 claims description 25
229910044991 metal oxide Inorganic materials 0.000 claims description 9
150000004706 metal oxides Chemical class 0.000 claims description 9
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
SXZIXHOMFPUIRK-UHFFFAOYSA-N diphenylmethanimine Chemical compound C=1C=CC=CC=1C(=N)C1=CC=CC=C1 SXZIXHOMFPUIRK-UHFFFAOYSA-N 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
230000001590 oxidative effect Effects 0.000 claims description 5
229910052759 nickel Inorganic materials 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
229910052709 silver Inorganic materials 0.000 claims description 3
239000004332 silver Substances 0.000 claims description 3
229910052716 thallium Inorganic materials 0.000 claims description 3
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000001033 ether group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 description 20
150000002466 imines Chemical class 0.000 description 13
238000000034 method Methods 0.000 description 12
-1 benzophenone imines Chemical class 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
239000012965 benzophenone Substances 0.000 description 7
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
VQSIVLYYQQCXAF-UHFFFAOYSA-N n-(benzhydrylideneamino)-1,1-diphenylmethanimine Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)=NN=C(C=1C=CC=CC=1)C1=CC=CC=C1 VQSIVLYYQQCXAF-UHFFFAOYSA-N 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
150000008366 benzophenones Chemical class 0.000 description 4
YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
229910001873 dinitrogen Inorganic materials 0.000 description 3
229910001882 dioxygen Inorganic materials 0.000 description 3
150000004679 hydroxides Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
DZKRDHLYQRTDBU-UPHRSURJSA-N (z)-but-2-enediperoxoic acid Chemical compound OOC(=O)\C=C/C(=O)OO DZKRDHLYQRTDBU-UPHRSURJSA-N 0.000 description 2
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 2
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-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
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000005708 Sodium hypochlorite Substances 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 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
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
QZPSXPBJTPJTSZ-UHFFFAOYSA-N aqua regia Chemical compound Cl.O[N+]([O-])=O QZPSXPBJTPJTSZ-UHFFFAOYSA-N 0.000 description 2
ZJRXSAYFZMGQFP-UHFFFAOYSA-N barium peroxide Chemical compound [Ba+2].[O-][O-] ZJRXSAYFZMGQFP-UHFFFAOYSA-N 0.000 description 2
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000006757 chemical reactions by type Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000000975 co-precipitation Methods 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000004675 formic acid derivatives Chemical class 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000004898 kneading Methods 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
150000002823 nitrates Chemical class 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 2
230000001172 regenerating effect Effects 0.000 description 2
AYKOTYRPPUMHMT-UHFFFAOYSA-N silver;hydrate Chemical compound O.[Ag] AYKOTYRPPUMHMT-UHFFFAOYSA-N 0.000 description 2
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 2
LPHBARMWKLYWRA-UHFFFAOYSA-N thallium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Tl+3].[Tl+3] LPHBARMWKLYWRA-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
DRZBKQOLJGOKPI-UHFFFAOYSA-N (2,4-dimethylphenyl)-phenylmethanimine Chemical compound CC1=CC(C)=CC=C1C(=N)C1=CC=CC=C1 DRZBKQOLJGOKPI-UHFFFAOYSA-N 0.000 description 1
VKQBAMNSOYATFC-UHFFFAOYSA-N (2,4-dinitrophenyl)-phenylmethanimine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1C(=N)C1=CC=CC=C1 VKQBAMNSOYATFC-UHFFFAOYSA-N 0.000 description 1
ONIUSLYNUDAJPW-UHFFFAOYSA-N (2-chloro-4-methylphenyl)-phenylmethanone Chemical compound ClC1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 ONIUSLYNUDAJPW-UHFFFAOYSA-N 0.000 description 1
CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 1
URBLVRAVOIVZFJ-UHFFFAOYSA-N (3-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 URBLVRAVOIVZFJ-UHFFFAOYSA-N 0.000 description 1
BTAPKJQUBUQJHY-UHFFFAOYSA-N (4-butyl-2-methylphenyl)-phenylmethanimine Chemical compound CC1=CC(CCCC)=CC=C1C(=N)C1=CC=CC=C1 BTAPKJQUBUQJHY-UHFFFAOYSA-N 0.000 description 1
BTWVUNYJERXYOJ-UHFFFAOYSA-N (4-butylphenyl)-phenylmethanimine Chemical compound C1=CC(CCCC)=CC=C1C(=N)C1=CC=CC=C1 BTWVUNYJERXYOJ-UHFFFAOYSA-N 0.000 description 1
PKBDBEIGGVURKI-UHFFFAOYSA-N (4-chlorophenyl)-phenylmethanimine Chemical compound C1=CC(Cl)=CC=C1C(=N)C1=CC=CC=C1 PKBDBEIGGVURKI-UHFFFAOYSA-N 0.000 description 1
OFYULLYNFNGACP-UHFFFAOYSA-N (4-cyclohexylphenyl)-phenylmethanimine Chemical compound C=1C=C(C2CCCCC2)C=CC=1C(=N)C1=CC=CC=C1 OFYULLYNFNGACP-UHFFFAOYSA-N 0.000 description 1
BRIQAWAIQIIECA-UHFFFAOYSA-N (4-decylphenyl)-phenylmethanimine Chemical compound C1=CC(CCCCCCCCCC)=CC=C1C(=N)C1=CC=CC=C1 BRIQAWAIQIIECA-UHFFFAOYSA-N 0.000 description 1
HWHRFBMTBQRKNB-UHFFFAOYSA-N (4-ethylphenyl)-phenylmethanimine Chemical compound C1=CC(CC)=CC=C1C(=N)C1=CC=CC=C1 HWHRFBMTBQRKNB-UHFFFAOYSA-N 0.000 description 1
KKXHZQYGRFEPIW-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanimine Chemical compound C1=CC(OC)=CC=C1C(=N)C1=CC=CC=C1 KKXHZQYGRFEPIW-UHFFFAOYSA-N 0.000 description 1
YOFJTMBUKFBJRU-UHFFFAOYSA-N (4-pentylphenyl)-phenylmethanimine Chemical compound C1=CC(CCCCC)=CC=C1C(=N)C1=CC=CC=C1 YOFJTMBUKFBJRU-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
ZKYXDHOGIQEYQB-UHFFFAOYSA-N 1-[4-(benzenecarboximidoyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C(=N)C1=CC=CC=C1 ZKYXDHOGIQEYQB-UHFFFAOYSA-N 0.000 description 1
PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
KUKQOSHHTHVRDB-UHFFFAOYSA-N 4-(benzenecarboximidoyl)benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(=N)C1=CC=CC=C1 KUKQOSHHTHVRDB-UHFFFAOYSA-N 0.000 description 1
RPZDWCSUGSQAMO-UHFFFAOYSA-N 4-(benzenecarboximidoyl)phenol Chemical compound C1=CC(O)=CC=C1C(=N)C1=CC=CC=C1 RPZDWCSUGSQAMO-UHFFFAOYSA-N 0.000 description 1
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000003570 air Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
FMJLJZORCRAZHN-UHFFFAOYSA-N bis(4-methylphenyl)methanimine Chemical compound C1=CC(C)=CC=C1C(=N)C1=CC=C(C)C=C1 FMJLJZORCRAZHN-UHFFFAOYSA-N 0.000 description 1
238000007664 blowing Methods 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
238000001354 calcination Methods 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001875 compounds Chemical class 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
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
229940045803 cuprous chloride Drugs 0.000 description 1
WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
239000004914 cyclooctane Substances 0.000 description 1
UAMZXLIURMNTHD-UHFFFAOYSA-N dialuminum;magnesium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Mg+2].[Al+3].[Al+3] UAMZXLIURMNTHD-UHFFFAOYSA-N 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
229960001826 dimethylphthalate Drugs 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
AVFCREGJOCVASG-UHFFFAOYSA-N dithallium Chemical compound [Tl]#[Tl] AVFCREGJOCVASG-UHFFFAOYSA-N 0.000 description 1
238000004880 explosion Methods 0.000 description 1
SFYLVTNFLRJWTA-UHFFFAOYSA-N fluoren-1-imine Chemical compound C1=CC=C2C3=CC=CC(=N)C3=CC2=C1 SFYLVTNFLRJWTA-UHFFFAOYSA-N 0.000 description 1
YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000007866 imination reaction Methods 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
XMFOQHDPRMAJNU-UHFFFAOYSA-N lead(ii,iv) oxide Chemical compound O1[Pb]O[Pb]11O[Pb]O1 XMFOQHDPRMAJNU-UHFFFAOYSA-N 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
GNMQOUGYKPVJRR-UHFFFAOYSA-N nickel(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Ni+3].[Ni+3] GNMQOUGYKPVJRR-UHFFFAOYSA-N 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
FYEOPTYALPEIAU-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanimine Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=N)C1=CC=CC=C1 FYEOPTYALPEIAU-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000005245 sintering Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP14294479A 1979-11-05 1979-11-05 Production of benzophenodiazine Granted JPS5665855A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP14294479A JPS5665855A (en)	1979-11-05	1979-11-05	Production of benzophenodiazine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP14294479A JPS5665855A (en)	1979-11-05	1979-11-05	Production of benzophenodiazine

Publications (2)

Publication Number	Publication Date
JPS5665855A JPS5665855A (en)	1981-06-03
JPS6337781B2 true JPS6337781B2 (sk)	1988-07-27

Family

ID=15327270

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP14294479A Granted JPS5665855A (en)	1979-11-05	1979-11-05	Production of benzophenodiazine

Country Status (1)

Country	Link
JP (1)	JPS5665855A (sk)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4420548A (en) *	1980-11-28	1983-12-13	Canon Kabushiki Kaisha	Electrophotographic member with hydrazone or ketazine compounds

1979
- 1979-11-05 JP JP14294479A patent/JPS5665855A/ja active Granted

Also Published As

Publication number	Publication date
JPS5665855A (en)	1981-06-03

Publication	Publication Date	Title
JP2018164910A (ja)	2018-10-25	改良された選択的アンモ酸化触媒
WO1999058241A1 (fr)	1999-11-18	Procede de regeneration d'un catalyseur a lit fluidise a oxyde contenant du molybdenum
JP2000037623A (ja)	2000-02-08	酸化用触媒の調製方法
JP2000254496A (ja)	2000-09-19	アクリル酸製造用の触媒
JP4081824B2 (ja)	2008-04-30	アクリル酸の製造方法
JPS6337781B2 (sk)	1988-07-27
JPH11226408A (ja)	1999-08-24	金属酸化物触媒の製造方法
JP2005320331A (ja)	2005-11-17	アクロレインおよび／またはアクリル酸を製造する方法
JP3854442B2 (ja)	2006-12-06	高選択的酸化反応用触媒
JPH07289907A (ja)	1995-11-07	ニトリル製造用触媒の製造方法
JP3522087B2 (ja)	2004-04-26	モリブデン含有酸化物流動層触媒の使用法
US4032620A (en)	1977-06-28	Process for preparing dicyan
JPS5826907B2 (ja)	1983-06-06	ベンゾフエノンアジン類の製造法
JPH0975740A (ja)	1997-03-25	メタクリル酸製造用触媒及びこれを用いてなるメタクリル酸の製造方法
JP3912074B2 (ja)	2007-05-09	水素の選択的酸化触媒、水素の選択的酸化方法、及び炭化水素の脱水素方法
JP3794235B2 (ja)	2006-07-05	水素の選択的酸化触媒、水素の選択的酸化方法及び炭化水素の脱水素方法
JP2003320248A (ja)	2003-11-11	酸化用触媒の調製方法とその触媒を用いたニトリルの製法
JP2002102706A (ja)	2002-04-09	メタクリル酸製造用触媒の再活性化方法
JP4090232B2 (ja)	2008-05-28	芳香族化合物の製造方法
JP2001300310A (ja)	2001-10-30	金属酸化物触媒の製造方法
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
JPS6059899B2 (ja)	1985-12-27	ベンゾフエノンアジン類の製造方法
JP2002205964A (ja)	2002-07-23	芳香族カルボニル化合物の製造方法
JPH0717550B2 (ja)	1995-03-01	フルオロベンゼンの製造法
JPH11290684A (ja)	1999-10-26	酢酸及びエチレンの製造方法