NL8006203A - Werkwijze voor het hydrogeneren van een aromatisch dinitril. - Google Patents

Werkwijze voor het hydrogeneren van een aromatisch dinitril. Download PDF

Info

Publication number: NL8006203A
Authority: NL; Netherlands
Prior art keywords: catalyst; cobalt; rhodium; ether; solvent
Prior art date: 1979-11-16

Application number

NL8006203A

Other languages

English (en)

Dutch (nl)

Original Assignee

Suntech

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.)

1979-11-16

Filing date

1980-11-13

Publication date

1981-06-16

1980-11-13 Application filed by Suntech filed Critical Suntech

1981-06-16 Publication of NL8006203A publication Critical patent/NL8006203A/nl

Links

238000000034 method Methods 0.000 title claims description 26
230000008569 process Effects 0.000 title claims description 20
239000003054 catalyst Substances 0.000 claims description 85
229910017052 cobalt Inorganic materials 0.000 claims description 52
239000010941 cobalt Substances 0.000 claims description 52
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 52
229910052703 rhodium Inorganic materials 0.000 claims description 43
239000010948 rhodium Substances 0.000 claims description 43
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 43
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
239000002904 solvent Substances 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
238000005984 hydrogenation reaction Methods 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical group N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 claims description 9
229910021529 ammonia Inorganic materials 0.000 claims description 8
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical group COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
239000004721 Polyphenylene oxide Substances 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
229920000570 polyether Polymers 0.000 claims description 2
238000005470 impregnation Methods 0.000 claims 1
150000002825 nitriles Chemical class 0.000 description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
229910052739 hydrogen Inorganic materials 0.000 description 12
239000001257 hydrogen Substances 0.000 description 12
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
239000006227 byproduct Substances 0.000 description 3
230000007423 decrease Effects 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
-1 aromatic nitriles Chemical class 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
SUCYXRASDBOYGB-UHFFFAOYSA-N cobalt rhodium Chemical compound [Co].[Rh] SUCYXRASDBOYGB-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001354 calcination Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
230000008570 general process Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
XBENBKUMYAUPFF-UHFFFAOYSA-N naphthalene-1,8-dicarbonitrile Chemical compound C1=CC(C#N)=C2C(C#N)=CC=CC2=C1 XBENBKUMYAUPFF-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
239000003921 oil Substances 0.000 description 1
WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
229920006391 phthalonitrile polymer Polymers 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000036632 reaction speed Effects 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
150000003283 rhodium Chemical class 0.000 description 1
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8913—Cobalt and noble metals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

NL8006203A 1979-11-16 1980-11-13 Werkwijze voor het hydrogeneren van een aromatisch dinitril. NL8006203A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/095,189 US4247478A (en)	1979-11-16	1979-11-16	Process and catalyst for hydrogenation of aromatic dinitriles
US9518979		1979-11-16

Publications (1)

Publication Number	Publication Date
NL8006203A true NL8006203A (nl)	1981-06-16

Family

ID=22250563

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8006203A NL8006203A (nl)	1979-11-16	1980-11-13	Werkwijze voor het hydrogeneren van een aromatisch dinitril.

Country Status (10)

Country	Link
US (1)	US4247478A (fr)
JP (1)	JPS5683451A (fr)
BE (1)	BE886181A (fr)
CA (1)	CA1152971A (fr)
DE (1)	DE3043115A1 (fr)
FR (1)	FR2469394B1 (fr)
GB (1)	GB2063258B (fr)
IL (1)	IL61393A (fr)
IT (1)	IT1141090B (fr)
NL (1)	NL8006203A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4973746A (en) *	1988-10-24	1990-11-27	General Electric Company	Process for converting pet scrap to diamine monomers
CN1091001C (zh) *	1999-08-19	2002-09-18	中国石油化工集团公司	用于制备间苯二甲胺的催化剂
DE102005045806A1 (de) *	2005-09-24	2007-03-29	Basf Ag	Verfahren zur Herstellung von Xylylendiamin

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2165515A (en) *	1933-05-18	1939-07-11	Ig Farbenindustrie Ag	Production of amines by the catalytic hydrogenation of nitriles
US2953490A (en) *	1957-03-14	1960-09-20	Monsanto Chemicals	Propylamine fungicides
US3177258A (en) *	1960-02-24	1965-04-06	Engelhard Ind Inc	Hydrogenation process using rutheniumcontaining catalysts
US3117162A (en) *	1960-03-30	1964-01-07	Engelhard Ind Inc	Hydrogenation of nitriles
US3110747A (en) *	1960-06-13	1963-11-12	Shell Oil Co	Homogeneous hydrogenation catalysis
US3152184A (en) *	1962-01-19	1964-10-06	Hercules Powder Co Ltd	Catalytic hydrogenation of nitriles
US3558709A (en) *	1968-04-19	1971-01-26	Huels Chemische Werke Ag	Process for the preparation of amines or diamines by the catalytic hydrogenation of nitriles and dinitriles
DE1793452B2 (de) *	1968-09-19	1976-11-18	Basf Ag, 6700 Ludwigshafen	Verfahren zur verbesserung der waermeabfuehrung bei katalytischen hydrierungen
US4163025A (en) *	1975-01-16	1979-07-31	Miles Laboratories, Inc.	Process for the production of benzylamine and dibenzylamine
FR2303789A1 (fr) *	1975-01-28	1976-10-08	Miles Lab	Procede de preparation de l'alpha-ethylbenzylamine
US4140720A (en) *	1977-05-19	1979-02-20	Phillips Petroleum Company	Cobalt hydrogenation catalyst activation
US4215019A (en) *	1978-11-14	1980-07-29	Phillips Petroleum Company	Ruthenium-cobalt-gold catalyst for hydrogenation of unsaturated dinitriles
US4186146A (en) *	1979-02-01	1980-01-29	Suntech, Inc.	Hydrogenation of aromatic nitriles to primary amines

1979
- 1979-11-16 US US06/095,189 patent/US4247478A/en not_active Expired - Lifetime
1980
- 1980-11-02 IL IL61393A patent/IL61393A/xx unknown
- 1980-11-05 IT IT25793/80A patent/IT1141090B/it active
- 1980-11-06 CA CA000364079A patent/CA1152971A/fr not_active Expired
- 1980-11-06 GB GB8035749A patent/GB2063258B/en not_active Expired
- 1980-11-11 JP JP15777180A patent/JPS5683451A/ja active Pending
- 1980-11-13 NL NL8006203A patent/NL8006203A/nl not_active Application Discontinuation
- 1980-11-14 DE DE19803043115 patent/DE3043115A1/de not_active Withdrawn
- 1980-11-14 BE BE0/202810A patent/BE886181A/fr not_active IP Right Cessation
- 1980-11-14 FR FR8024201A patent/FR2469394B1/fr not_active Expired

Also Published As

Publication number	Publication date
IT1141090B (it)	1986-10-01
FR2469394A1 (fr)	1981-05-22
IL61393A (en)	1984-05-31
GB2063258B (en)	1984-07-11
IL61393A0 (en)	1980-12-31
CA1152971A (fr)	1983-08-30
GB2063258A (en)	1981-06-03
BE886181A (fr)	1981-05-14
FR2469394B1 (fr)	1985-06-07
DE3043115A1 (de)	1981-05-21
US4247478A (en)	1981-01-27
JPS5683451A (en)	1981-07-08
IT8025793A0 (it)	1980-11-05

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1988-01-04	BV	The patent application has lapsed

Publication	Publication Date	Title
CA1109491A (fr)	1981-09-22	Procede d'obtention d'amines aliphatiques
JPH107627A (ja)	1998-01-13	場合により置換された４−アミノジフエニルアミン類の調製方法
EP0476404B1 (fr)	1995-06-21	Procédé pour la préparation d'aniline de grande pureté
KR940006762B1 (ko)	1994-07-27	고순도 아닐린의 제조방법
DE60307686T2 (de)	2006-12-07	Hydrogenierung von einringigen aromatischen Diaminen
CA1126760A (fr)	1982-06-29	Hydrogenation de nitriles aromatiques en amines primaires
NL8006203A (nl)	1981-06-16	Werkwijze voor het hydrogeneren van een aromatisch dinitril.
JP2002521356A (ja)	2002-07-16	６−アミノカプロニトリルおよびヘキサメチレンジアミンの同時製造のための改良方法
JPH02233A (ja)	1990-01-05	Ｎ−置換アミンの製造方法
EP0052511B1 (fr)	1984-03-07	Préparation de p-phénylènediamine
JPH02234A (ja)	1990-01-05	Ｎ−置換アミンの製造方法
US4320032A (en)	1982-03-16	Catalyst for hydrogenation of aromatic dinitriles
JPH08500368A (ja)	1996-01-16	アセタールをエーテルに転化する方法
NL8000538A (nl)	1980-08-05	Hydrogeneringswerkwijze.
JPS6362525B2 (fr)	1988-12-02
US3261869A (en)	1966-07-19	Method for the production of benzyl anilines
US4792631A (en)	1988-12-20	Preparation of di-tert.-butylethylenediamine
JPS6144848B2 (fr)	1986-10-04
JPH01160947A (ja)	1989-06-23	ジアルキルアミノエタノールの精製法
JPH02202855A (ja)	1990-08-10	第２級アミンの製造方法
KR0138789B1 (ko)	1998-05-01	아미노디페닐아민의 제조방법
JPH01102045A (ja)	1989-04-19	Ｎ−置換アミンの製造方法
JP3177350B2 (ja)	2001-06-18	ジノニルジフェニルアミンの製造法
JPS5965031A (ja)	1984-04-13	２−シス−ｔ−ブチルシクロヘキサノ−ルの製法
JPH0227981B2 (fr)	1990-06-20