NL8403258A - Werkwijze voor de bereiding van pyrimidine. - Google Patents

Werkwijze voor de bereiding van pyrimidine. Download PDF

Info

Publication number: NL8403258A
Authority: NL; Netherlands
Prior art keywords: catalyst; diaminopropane; process according; pyrimidine; methanol
Prior art date: 1984-10-26

Application number

NL8403258A

Other languages

English (en)

Dutch (nl)

Original Assignee

Stamicarbon

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.)

1984-10-26

Filing date

1984-10-26

Publication date

1986-05-16

1984-10-26 Application filed by Stamicarbon filed Critical Stamicarbon

1984-10-26 Priority to NL8403258A priority Critical patent/NL8403258A/nl

1985-10-10 Priority to US06/785,998 priority patent/US4719299A/en

1985-10-22 Priority to AT85201725T priority patent/ATE50991T1/de

1985-10-22 Priority to EP85201725A priority patent/EP0181026B1/de

1985-10-22 Priority to DE8585201725T priority patent/DE3576501D1/de

1985-10-25 Priority to JP60237761A priority patent/JPS61103875A/ja

1986-05-16 Publication of NL8403258A publication Critical patent/NL8403258A/nl

Links

CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims abstract description 23
238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 45
239000003054 catalyst Substances 0.000 claims abstract description 33
238000006243 chemical reaction Methods 0.000 claims abstract description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 17
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 13
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 13
239000003153 chemical reaction reagent Substances 0.000 claims abstract description 9
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
150000001340 alkali metals Chemical class 0.000 claims abstract description 6
229910052763 palladium Inorganic materials 0.000 claims abstract description 5
ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 claims description 12
239000011734 sodium Substances 0.000 claims description 7
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 abstract description 24
239000003863 metallic catalyst Substances 0.000 abstract description 3
239000011541 reaction mixture Substances 0.000 abstract description 3
238000004519 manufacturing process Methods 0.000 abstract 1
RILVNLMOTMFTMQ-UHFFFAOYSA-N 2-ethylpyrimidine Chemical compound CCC1=NC=CC=N1 RILVNLMOTMFTMQ-UHFFFAOYSA-N 0.000 description 7
LNJMHEJAYSYZKK-UHFFFAOYSA-N 2-methylpyrimidine Chemical compound CC1=NC=CC=N1 LNJMHEJAYSYZKK-UHFFFAOYSA-N 0.000 description 7
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000012071 phase Substances 0.000 description 3
229910018967 Pt—Rh Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000007792 gaseous phase Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 description 1
229910018404 Al2 O3 Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910002090 carbon oxide Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
-1 for example Chemical class 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000004476 plant protection product Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
239000012495 reaction gas Substances 0.000 description 1
238000005070 sampling Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/58—Platinum group metals with alkali- or alkaline earth metals

Landscapes

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

NL8403258A 1984-10-26 1984-10-26 Werkwijze voor de bereiding van pyrimidine. NL8403258A (nl)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
NL8403258A NL8403258A (nl)	1984-10-26	1984-10-26	Werkwijze voor de bereiding van pyrimidine.
US06/785,998 US4719299A (en)	1984-10-26	1985-10-10	Process for preparing pyrimidine
AT85201725T ATE50991T1 (de)	1984-10-26	1985-10-22	Verfahren zur herstellung von pyrimidin.
EP85201725A EP0181026B1 (de)	1984-10-26	1985-10-22	Verfahren zur Herstellung von Pyrimidin
DE8585201725T DE3576501D1 (de)	1984-10-26	1985-10-22	Verfahren zur herstellung von pyrimidin.
JP60237761A JPS61103875A (ja)	1984-10-26	1985-10-25	ピリミジンの製法

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8403258A NL8403258A (nl)	1984-10-26	1984-10-26	Werkwijze voor de bereiding van pyrimidine.
NL8403258		1984-10-26

Publications (1)

Publication Number	Publication Date
NL8403258A true NL8403258A (nl)	1986-05-16

Family

ID=19844660

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8403258A NL8403258A (nl)	1984-10-26	1984-10-26	Werkwijze voor de bereiding van pyrimidine.

Country Status (6)

Country	Link
US (1)	US4719299A (de)
EP (1)	EP0181026B1 (de)
JP (1)	JPS61103875A (de)
AT (1)	ATE50991T1 (de)
DE (1)	DE3576501D1 (de)
NL (1)	NL8403258A (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL8603168A (nl) *	1986-12-12	1988-07-01	Stamicarbon	Werkwijze voor de bereiding van een 2-alkyl-1,4,5,6-tetrahydropyrimidine.
US4999427A (en) *	1988-05-16	1991-03-12	Dowelanco	Process for the preparation of 2-alkylpyrimidines
FR2635471A1 (fr) *	1988-08-22	1990-02-23	Solvay	Compositions catalytiques, procede pour leur obtention et procede d'hydrogenation de 1,1,2-trichloro-1,2,2-trifluorethane au moyen de ces compositions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB930090A (de) *

1984
- 1984-10-26 NL NL8403258A patent/NL8403258A/nl not_active Application Discontinuation
1985
- 1985-10-10 US US06/785,998 patent/US4719299A/en not_active Expired - Fee Related
- 1985-10-22 DE DE8585201725T patent/DE3576501D1/de not_active Expired - Lifetime
- 1985-10-22 EP EP85201725A patent/EP0181026B1/de not_active Expired - Lifetime
- 1985-10-22 AT AT85201725T patent/ATE50991T1/de active
- 1985-10-25 JP JP60237761A patent/JPS61103875A/ja active Pending

Also Published As

Publication number	Publication date
ATE50991T1 (de)	1990-03-15
EP0181026A1 (de)	1986-05-14
JPS61103875A (ja)	1986-05-22
EP0181026B1 (de)	1990-03-14
US4719299A (en)	1988-01-12
DE3576501D1 (de)	1990-04-19

Legal Events

Date	Code	Title	Description
1986-05-16	A1B	A search report has been drawn up
1986-08-18	DNT	Communications of changes of names of applicants whose applications have been laid open to public inspection	Free format text: STAMICARBON B.V. TE GELEEN
1988-06-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US4824869A (en)	1989-04-25	Base-modified metal oxide catalysts for the conversion of synthesis gas to alcohols
KR860001601B1 (ko)	1986-10-13	인돌류의 제조방법
HU178079B (en)	1982-02-28	Process for dehalogenating aromatic compounds containing halogenes
EP0181026B1 (de)	1990-03-14	Verfahren zur Herstellung von Pyrimidin
US5034560A (en)	1991-07-23	Synthesis of ethylamines
NL8502796A (nl)	1986-09-01	Werkwijze voor de bereiding van pyrimidine en 2-alkylpyrimidine.
CA2736305A1 (en)	2010-04-01	Method for the preparation of 3-methylpyridine
JPH0373535B2 (de)	1991-11-22
JPH10147557A (ja)	1998-06-02	不均一系触媒を使用して、ｎ−アルキル置換アミノアルキンを製造する方法
EP0276503B1 (de)	1992-07-22	Verfahren zur Herstellung eines 2-Alkyl- oder 2-Phenyl-1,4,5,6-tetrahydropyrimidins und Verfahren zur Herstellung von 2-Alkyl- oder 2-Phenyl-pyrimidinen
NL8403259A (nl)	1986-05-16	Werkwijze voor de bereiding van pyrimidine.
KR100710546B1 (ko)	2007-04-24	고수율로 ＤＬ-α-토코페롤을 제조하는 방법
NL8301416A (nl)	1984-11-16	Werkwijze voor de bereiding van een pyridon-2.
NL8502797A (nl)	1986-09-01	Werkwijze voor de bereiding van 2-alkylpyrimidine.
NL8500431A (nl)	1986-09-01	Werkwijze voor de bereiding van pyrimidine.
NL8105278A (nl)	1983-06-16	Werkwijze voor de bereiding van een lactam.
EP0200923A2 (de)	1986-11-12	Herstellung von Aminen aus Olefinen mit Verwendung von Ammonium-Halogenid-Katalysatoren
EP0137567B1 (de)	1988-10-19	Verfahren zur Herstellung von Pyrimidin
EP0013554A1 (de)	1980-07-23	Verfahren zur Herstellung von 1,17-Diamino-9-azaheptadecan
US5118846A (en)	1992-06-02	Synthesis of N-disubstituted amides by reaction of amides with certain organic hydroxyl compounds
EP0066346B1 (de)	1985-10-30	Verfahren zur Herstellung von 2-Alkylpyrrol
US4473699A (en)	1984-09-25	Process for the preparation of indole and skatole
WO1988000189A1 (en)	1988-01-14	A process for the preparation of nitrogen-containing heterocyclic compounds
US4827031A (en)	1989-05-02	Process for preparing amines from olefins with ammonium halide catalysts
SU255203A1 (ru)		Способ приготовления катализатора для получения ксилидина