NL9200580A - Werkwijze voor de bereiding van 2-(2-cyanoethyl)-cyclopentanonen. - Google Patents

Werkwijze voor de bereiding van 2-(2-cyanoethyl)-cyclopentanonen. Download PDF

Info

Publication number: NL9200580A
Authority: NL; Netherlands
Prior art keywords: cyclopentanone; cyanoethyl; grams; reaction; acrylonitrile
Prior art date: 1992-03-30

Application number

NL9200580A

Other languages

English (en)

Dutch (nl)

Original Assignee

Dsm Nv

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.)

1992-03-30

Filing date

1992-03-30

Publication date

1993-10-18

1992-03-30 Application filed by Dsm Nv filed Critical Dsm Nv

1992-03-30 Priority to NL9200580A priority Critical patent/NL9200580A/nl

1993-03-24 Priority to EP93200851A priority patent/EP0564030B1/de

1993-03-24 Priority to DE69302617T priority patent/DE69302617T2/de

1993-03-24 Priority to AT93200851T priority patent/ATE138057T1/de

1993-03-29 Priority to JP09354993A priority patent/JP3237097B2/ja

1993-03-30 Priority to US08/039,745 priority patent/US5319125A/en

1993-10-18 Publication of NL9200580A publication Critical patent/NL9200580A/nl

Links

238000000034 method Methods 0.000 title claims abstract description 24
238000002360 preparation method Methods 0.000 title claims abstract description 12
-1 2-CYANOETHYL Chemical class 0.000 title description 4
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims abstract description 54
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 42
UVVOIPOAZZQJDF-UHFFFAOYSA-N 3-(2-oxocyclopentyl)propanenitrile Chemical compound O=C1CCCC1CCC#N UVVOIPOAZZQJDF-UHFFFAOYSA-N 0.000 claims abstract description 22
150000002825 nitriles Chemical class 0.000 claims abstract description 17
238000006243 chemical reaction Methods 0.000 claims abstract description 14
230000003197 catalytic effect Effects 0.000 claims abstract description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
150000001412 amines Chemical class 0.000 claims description 10
239000011541 reaction mixture Substances 0.000 claims description 10
150000007513 acids Chemical class 0.000 claims description 5
239000003054 catalyst Substances 0.000 abstract description 9
239000002253 acid Substances 0.000 abstract description 5
230000000694 effects Effects 0.000 abstract description 4
OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 20
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 12
238000004519 manufacturing process Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 7
KRNSYSYRLQDHDK-UHFFFAOYSA-N 6,7-dihydro-5h-cyclopenta[b]pyridine Chemical compound C1=CN=C2CCCC2=C1 KRNSYSYRLQDHDK-UHFFFAOYSA-N 0.000 description 6
239000005711 Benzoic acid Substances 0.000 description 6
235000010233 benzoic acid Nutrition 0.000 description 6
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
238000004821 distillation Methods 0.000 description 6
238000002474 experimental method Methods 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
150000003141 primary amines Chemical class 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000006356 dehydrogenation reaction Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
SPTVCXKSSRBTMN-UHFFFAOYSA-N 3-(2-oxocyclohexyl)propanenitrile Chemical compound O=C1CCCCC1CCC#N SPTVCXKSSRBTMN-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
GCMPNULCLNCRBA-UHFFFAOYSA-N propan-2-one;pyrrolidine Chemical compound CC(C)=O.C1CCNC1 GCMPNULCLNCRBA-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL9200580A 1992-03-30 1992-03-30 Werkwijze voor de bereiding van 2-(2-cyanoethyl)-cyclopentanonen. NL9200580A (nl)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
NL9200580A NL9200580A (nl)	1992-03-30	1992-03-30	Werkwijze voor de bereiding van 2-(2-cyanoethyl)-cyclopentanonen.
EP93200851A EP0564030B1 (de)	1992-03-30	1993-03-24	Verfahren zur Herstellung von 2-(2-Cyanoethyl)-Cyclopentanonen
DE69302617T DE69302617T2 (de)	1992-03-30	1993-03-24	Verfahren zur Herstellung von 2-(2-Cyanoethyl)-Cyclopentanonen
AT93200851T ATE138057T1 (de)	1992-03-30	1993-03-24	Verfahren zur herstellung von 2-(2-cyanoethyl)- cyclopentanonen
JP09354993A JP3237097B2 (ja)	1992-03-30	1993-03-29	２‐（２‐シアノエチル）シクロペンタノンの製造方法
US08/039,745 US5319125A (en)	1992-03-30	1993-03-30	Method for the preparation of 2-(2-cyanoethyl)-cyclopentanones

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL9200580A NL9200580A (nl)	1992-03-30	1992-03-30	Werkwijze voor de bereiding van 2-(2-cyanoethyl)-cyclopentanonen.
NL9200580		1992-03-30

Publications (1)

Publication Number	Publication Date
NL9200580A true NL9200580A (nl)	1993-10-18

Family

ID=19860628

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL9200580A NL9200580A (nl)	1992-03-30	1992-03-30	Werkwijze voor de bereiding van 2-(2-cyanoethyl)-cyclopentanonen.

Country Status (6)

Country	Link
US (1)	US5319125A (de)
EP (1)	EP0564030B1 (de)
JP (1)	JP3237097B2 (de)
AT (1)	ATE138057T1 (de)
DE (1)	DE69302617T2 (de)
NL (1)	NL9200580A (de)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1002342C2 (de) *	1955-10-13	1957-07-18	Bayer Ag	Verfahren zur Herstellung von ª‡-monocyanaethylierten Ketonen
NL7808605A (nl) *	1978-08-19	1980-02-21	Stamicarbon	Werkwijze voor de bereiding van delta-ketozuren en derivaten hiervan.

1992
- 1992-03-30 NL NL9200580A patent/NL9200580A/nl unknown
1993
- 1993-03-24 AT AT93200851T patent/ATE138057T1/de not_active IP Right Cessation
- 1993-03-24 DE DE69302617T patent/DE69302617T2/de not_active Expired - Fee Related
- 1993-03-24 EP EP93200851A patent/EP0564030B1/de not_active Expired - Lifetime
- 1993-03-29 JP JP09354993A patent/JP3237097B2/ja not_active Expired - Fee Related
- 1993-03-30 US US08/039,745 patent/US5319125A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0564030A1 (de)	1993-10-06
DE69302617D1 (de)	1996-06-20
DE69302617T2 (de)	1997-01-16
EP0564030B1 (de)	1996-05-15
JP3237097B2 (ja)	2001-12-10
ATE138057T1 (de)	1996-06-15
JPH07267914A (ja)	1995-10-17
US5319125A (en)	1994-06-07

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NL9200580A (nl)	1993-10-18	Werkwijze voor de bereiding van 2-(2-cyanoethyl)-cyclopentanonen.
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