HU176576B - Eljárás N-szubsztituált aminvegyületek előállítására - Google Patents

Eljárás N-szubsztituált aminvegyületek előállítására Download PDF

Info

Publication number: HU176576B
Authority: HU; Hungary
Prior art keywords: compounds; alkyl; weight; amine; reductive alkylation
Prior art date: 1976-12-17

Application number

Other languages

English (en)

Hungarian (hu)

Inventor

Istvan Gemes

Istvan Peter

Daniel Kriza

Tamas Mandy

Istvan Szabados

Janos Frostner

Laszlo Torkos

Original Assignee

Magyar Szenhidrogenipari

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.)

1976-12-17

Filing date

1976-12-17

Publication date

1981-03-28

1976-12-17 Application filed by Magyar Szenhidrogenipari filed Critical Magyar Szenhidrogenipari

1976-12-17 Priority to HUNA001047 priority Critical patent/HU176576B/hu

1977-12-15 Priority to YU298977A priority patent/YU298977A/xx

1977-12-15 Priority to CS843177A priority patent/CS197311B2/cs

1977-12-15 Priority to RO7792485A priority patent/RO75156A/ro

1977-12-15 Priority to SU772554499A priority patent/SU799648A3/ru

1977-12-15 Priority to DD20266877A priority patent/DD133322A1/de

1977-12-17 Priority to PL20308277A priority patent/PL108060B1/pl

1981-03-28 Publication of HU176576B publication Critical patent/HU176576B/hu

Links

-1 amine compounds Chemical class 0.000 title description 19
238000004519 manufacturing process Methods 0.000 title 1
239000003054 catalyst Substances 0.000 claims description 34
238000000034 method Methods 0.000 claims description 28
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
238000005932 reductive alkylation reaction Methods 0.000 claims description 15
229910052697 platinum Inorganic materials 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 9
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 4
229910052702 rhenium Inorganic materials 0.000 claims description 4
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
101150059448 cdk7 gene Proteins 0.000 claims 1
230000005021 gait Effects 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 22
230000000694 effects Effects 0.000 description 13
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 9
230000007423 decrease Effects 0.000 description 8
239000000203 mixture Substances 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000006227 byproduct Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000000654 additive Substances 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 3
239000012467 final product Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000010970 precious metal Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
238000007126 N-alkylation reaction Methods 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
CXKAZTSHVRMSRT-UHFFFAOYSA-N 1-ethoxypropan-2-one Chemical compound CCOCC(C)=O CXKAZTSHVRMSRT-UHFFFAOYSA-N 0.000 description 1
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
229910000975 Carbon steel Inorganic materials 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
206010029897 Obsessive thoughts Diseases 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000005055 alkyl alkoxy group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
239000002199 base oil Substances 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
239000010962 carbon steel Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
239000003085 diluting agent Substances 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
150000002148 esters Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 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
238000000926 separation method Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
230000019635 sulfation Effects 0.000 description 1
238000005670 sulfation reaction Methods 0.000 description 1
238000005486 sulfidation Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

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

HUNA001047 1976-12-17 1976-12-17 Eljárás N-szubsztituált aminvegyületek előállítására HU176576B (hu)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
HUNA001047 HU176576B (hu)	1976-12-17	1976-12-17	Eljárás N-szubsztituált aminvegyületek előállítására
YU298977A YU298977A (en)	1976-12-17	1977-12-15	Process for preparing n-substituted amine compounds
CS843177A CS197311B2 (cs)	1976-12-17	1977-12-15	Zpusob katalýzy chemické přeměny aminosloučenin
RO7792485A RO75156A (ro)	1976-12-17	1977-12-15	Procedeu de obtinere a unor amine secundare
SU772554499A SU799648A3 (ru)	1976-12-17	1977-12-15	Способ получени -замещенныхАМиНОВ
DD20266877A DD133322A1 (de)	1976-12-17	1977-12-15	Verfahren zur herstellung n-substituierter aminoverbindungen
PL20308277A PL108060B1 (pl)	1976-12-17	1977-12-17	Method of producing n-substituted amines sposob wytwarzania n-podstawionych amin

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUNA001047 HU176576B (hu)	1976-12-17	1976-12-17	Eljárás N-szubsztituált aminvegyületek előállítására

Publications (1)

Publication Number	Publication Date
HU176576B true HU176576B (hu)	1981-03-28

Family

ID=10999856

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HUNA001047 HU176576B (hu)	1976-12-17	1976-12-17	Eljárás N-szubsztituált aminvegyületek előállítására

Country Status (7)

Country	Link
CS (1)	CS197311B2 (de)
DD (1)	DD133322A1 (de)
HU (1)	HU176576B (de)
PL (1)	PL108060B1 (de)
RO (1)	RO75156A (de)
SU (1)	SU799648A3 (de)
YU (1)	YU298977A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4116117A1 (de) *	1991-05-17	1992-11-19	Bayer Ag	Verfahren zur herstellung von dicyclohexylaminenn

1976
- 1976-12-17 HU HUNA001047 patent/HU176576B/hu not_active IP Right Cessation
1977
- 1977-12-15 SU SU772554499A patent/SU799648A3/ru active
- 1977-12-15 YU YU298977A patent/YU298977A/xx unknown
- 1977-12-15 DD DD20266877A patent/DD133322A1/de unknown
- 1977-12-15 RO RO7792485A patent/RO75156A/ro unknown
- 1977-12-15 CS CS843177A patent/CS197311B2/cs unknown
- 1977-12-17 PL PL20308277A patent/PL108060B1/pl unknown

Also Published As

Publication number	Publication date
DD133322A1 (de)	1978-12-27
CS197311B2 (cs)	1980-04-30
PL203082A1 (pl)	1978-12-04
YU298977A (en)	1983-01-21
PL108060B1 (pl)	1980-03-31
SU799648A3 (ru)	1981-01-23
RO75156A (ro)	1980-11-30

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628
1993-05-28	HPC4	Succession in title of patentee	Owner name: MOL MAGYAR OLAJ- ES GAZIPARI RT., HU
1996-08-28	HMM4	Cancellation of final prot. due to non-payment of fee

Publication	Publication Date	Title
EP0231788B1 (de)	1990-05-09	Hydrierung von Methylendianilin zur Herstellung von bis-(Para-aminocyclohexyl)methanen
JP4979877B2 (ja)	2012-07-18	ジエチレントリアミンおよび高級ポリエチレンポリアミンの製造のための方法
JPH10174875A (ja)	1998-06-30	アルキレンオキシド、アルコール、アルデヒドおよびケトンのアミノ化用触媒、およびその製造方法
RU2213088C2 (ru)	2003-09-27	Каталитическое гидрирование нитробензола с образованием 4-аминодифениламина
JP2002515474A (ja)	2002-05-28	４−アミノジフェニルアミンの調製方法
JP4105663B2 (ja)	2008-06-25	アミノエーテルアルコールをアミノエーテルアミンへ転化する方法
JPS60130551A (ja)	1985-07-12	第３級アミンの製造方法
JP2001316337A (ja)	2001-11-13	アルミニウム含有率が低い触媒を用いる芳香族ニトロ化化合物の連続式水素化
EP0618895B1 (de)	1997-09-03	Verfahren zur herstellung von aminonitrilen durch partielle hydrierung von nitrilen mit zwei oder mehr nitrilgruppen
US5994584A (en)	1999-11-30	Process for the preparation of 4-aminodiphenylamine
CN1194973A (zh)	1998-10-07	胺的n－烷基化反应
US3196179A (en)	1965-07-20	Preparation of cyclohexylamine by hydrogenation of aniline using a rhodium catalyst
HU176576B (hu)	1981-03-28	Eljárás N-szubsztituált aminvegyületek előállítására
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
US4760185A (en)	1988-07-26	Process for the ortho-alkylation of optionally alkyl-substituted m-phenylenediamines
US5922917A (en)	1999-07-13	Process for the preparation of 2-amino-1,3-propanediol
EP3613725B1 (de)	2022-04-06	Verfahren zur herstellung von indancarbaldehyd
US4226809A (en)	1980-10-07	Hydrogenation of unsaturated dinitriles using catalyst comprising reaction products of nickel compound and of a palladium compound each with an alkali metal borohydride
US4480127A (en)	1984-10-30	Process for the production of variable amounts of DPA and aniline using only phenol and ammonia as the feedstock
JPH06239809A (ja)	1994-08-30	第３級アミンの製造方法
JPH0948746A (ja)	1997-02-18	アミンの製造方法
JPH061758A (ja)	1994-01-11	アミノ化合物の製造方法
JP3089772B2 (ja)	2000-09-18	シクロヘキサン環を有するジオール化合物の製造方法
US4353841A (en)	1982-10-12	Aromatic isocyanate preparation
JP3972444B2 (ja)	2007-09-05	ジアリールアミン類の製造方法