JPS58189141A - エーテル基含有脂肪族溶剤中での芳香族第一アミンの製造法 - Google Patents

エーテル基含有脂肪族溶剤中での芳香族第一アミンの製造法

Info

Publication number: JPS58189141A
Authority: JP; Japan
Prior art keywords: imine; cycloaliphatic; catalyst; method described; compound
Prior art date: 1982-04-22
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.): Granted

Application number

JP58068489A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0416457B2 (de

Inventor

リユ−デイゲル・ベルトホルト

ウエルネル・ハインリツヒ・ミユ−レル

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.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1982-04-22

Filing date

1983-04-20

Publication date

1983-11-04

1983-04-20 Application filed by Hoechst AG filed Critical Hoechst AG

1983-11-04 Publication of JPS58189141A publication Critical patent/JPS58189141A/ja

1992-03-24 Publication of JPH0416457B2 publication Critical patent/JPH0416457B2/ja

Status Granted legal-status Critical Current

Links

150000004982 aromatic amines Chemical class 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title claims description 5
239000003054 catalyst Substances 0.000 claims description 22
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 19
238000000034 method Methods 0.000 claims description 18
150000002466 imines Chemical class 0.000 claims description 11
150000002576 ketones Chemical class 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
229910021529 ammonia Inorganic materials 0.000 claims description 9
-1 aromatic amino acid Chemical class 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
125000001033 ether group Chemical group 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
239000007791 liquid phase Substances 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
229910000510 noble metal Inorganic materials 0.000 claims description 2
230000000737 periodic effect Effects 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
150000002828 nitro derivatives Chemical class 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
WWAQPAKSFODDQR-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-2H-naphthalen-1-imine Chemical compound C1(CCCC2CC=CC=C12)=N WWAQPAKSFODDQR-UHFFFAOYSA-N 0.000 claims 1
QFNABHBYVSJWLO-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-2h-naphthalen-1-one Chemical compound C1C=CC=C2C(=O)CCCC21 QFNABHBYVSJWLO-UHFFFAOYSA-N 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 12
238000009835 boiling Methods 0.000 description 11
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
238000003756 stirring Methods 0.000 description 5
150000001983 dialkylethers Chemical class 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000000047 product Substances 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 3
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
229910052705 radium Inorganic materials 0.000 description 2
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 1
CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
NOQKKFBBAODEHN-UHFFFAOYSA-N 3,5-dimethylcyclohex-2-en-1-one Chemical compound CC1CC(C)=CC(=O)C1 NOQKKFBBAODEHN-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
238000006418 Brown reaction Methods 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001346 alkyl aryl ethers Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
IHNDUGMUECOVKK-UHFFFAOYSA-N aluminum chromium(3+) oxygen(2-) Chemical compound [O-2].[Cr+3].[O-2].[Al+3] IHNDUGMUECOVKK-UHFFFAOYSA-N 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
238000003287 bathing Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052593 corundum Inorganic materials 0.000 description 1
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical class O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
NNGAQKAUYDTUQR-UHFFFAOYSA-N cyclohexanimine Chemical compound N=C1CCCCC1 NNGAQKAUYDTUQR-UHFFFAOYSA-N 0.000 description 1
JHIVVAPYMSGYDF-PTQBSOBMSA-N cyclohexanone Chemical class O=[13C]1CCCCC1 JHIVVAPYMSGYDF-PTQBSOBMSA-N 0.000 description 1
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
238000007700 distillative separation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000010574 gas phase reaction Methods 0.000 description 1
125000000879 imine group Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
238000012805 post-processing Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052596 spinel Inorganic materials 0.000 description 1
239000011029 spinel Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
229910001845 yogo sapphire Inorganic materials 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

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

JP58068489A 1982-04-22 1983-04-20 エーテル基含有脂肪族溶剤中での芳香族第一アミンの製造法 Granted JPS58189141A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE3215060		1982-04-22
DE3215060.1		1982-04-22
DE3240548.0		1982-11-03

Publications (2)

Publication Number	Publication Date
JPS58189141A true JPS58189141A (ja)	1983-11-04
JPH0416457B2 JPH0416457B2 (de)	1992-03-24

Family

ID=6161685

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58068489A Granted JPS58189141A (ja)	1982-04-22	1983-04-20	エーテル基含有脂肪族溶剤中での芳香族第一アミンの製造法

Country Status (1)

Country	Link
JP (1)	JPS58189141A (de)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3219702A (en) *	1961-02-02	1965-11-23	Monsanto Co	Manufacture of aromatic amines by aromatization

1983
- 1983-04-20 JP JP58068489A patent/JPS58189141A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3219702A (en) *	1961-02-02	1965-11-23	Monsanto Co	Manufacture of aromatic amines by aromatization

Also Published As

Publication number	Publication date
JPH0416457B2 (de)	1992-03-24

Publication	Publication Date	Title
EP0101111B1 (de)	1986-01-22	Verfahren und katalytische Zusammensetzung zur Herstellung von Aldehyden, und so erhaltene Aldehyde
Debenneville et al.	1950	The behavior of aliphatic aldehydes in the Leuckart-Wallach reaction
JPH01151941A (ja)	1989-06-14	５員飽和窒素含有複素環化合物の製造用触媒組成物
JPH0362710B2 (de)	1991-09-26
JPH0321547B2 (de)	1991-03-22
JPS61109782A (ja)	1986-05-28	１‐アルキル‐又は１‐シクロアルキル‐ピペラジンの製法
JPS58189141A (ja)	1983-11-04	エーテル基含有脂肪族溶剤中での芳香族第一アミンの製造法
US4250093A (en)	1981-02-10	Process for the preparation of laotams
US4082748A (en)	1978-04-04	Process for production of oxazine diones
JPH0410451B2 (de)	1992-02-25
JP2004537405A (ja)	2004-12-16	パラジウム触媒
US3951996A (en)	1976-04-20	Process for making nicotinic acid hydrazides
JP2003516372A (ja)	2003-05-13	アリルアルコールの異性化の方法
US4463196A (en)	1984-07-31	Process for the preparation of citral
JP2012503616A (ja)	2012-02-09	３−メチルピリジンの調製方法
EP0093892B1 (de)	1986-05-28	Verfahren zur Herstellung von aromatischen Aminen
Humphlett et al.	1948	Preparation of Ketones from γ-Diethylaminobutyronitrile and Aromatic Grignard Reagents and their Conversion to Diamines. Synthesis of Quinacrine Analogs1, 2
US2496958A (en)	1950-02-07	1-alkyl-benzylaminopiperidines and their production
US4375561A (en)	1983-03-01	Process for the preparation of aromatic amines
JPH0667936B2 (ja)	1994-08-31	エルゴリンのｎ−メチル誘導体の製法
JP3238508B2 (ja)	2001-12-17	１−（４−ピリジル）ピペラジン類の製造法
US2773098A (en)	1956-12-04	Preparation of n, n'-dibenzylethylenediamine
US6184384B1 (en)	2001-02-06	Dechlorination of pyridines in acidic, zinc-containing mediums
JPH0381241A (ja)	1991-04-05	３，５―ジメチル―４―ヒドロキシベンズアルデヒドの製造方法
JPS61118348A (ja)	1986-06-05	ヒドロキシメチレンアルコキシ酢酸エステルの製造方法