CA1085873A - Preparation de cyclopropanecarbonitriles - Google Patents

Preparation de cyclopropanecarbonitriles

Info

Publication number: CA1085873A
Authority: CA; Canada
Prior art keywords: general formula; hal; preparation; aprotic solvent; polar aprotic
Prior art date: 1976-06-22
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.): Expired

Application number

CA279,843A

Other languages

English (en)

Inventor

Petrus A. Kramer

Helena Austermuhle-Bertola

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.)

Shell Canada Ltd

Original Assignee

Shell Canada Ltd

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.)

1976-06-22

Filing date

1977-06-03

Publication date

1980-09-16

1977-06-03 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1980-09-16 Application granted granted Critical

1980-09-16 Publication of CA1085873A publication Critical patent/CA1085873A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 10
238000002360 preparation method Methods 0.000 title claims abstract description 7
238000010438 heat treatment Methods 0.000 claims abstract description 7
239000003880 polar aprotic solvent Substances 0.000 claims abstract description 7
125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 5
229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 claims abstract description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
239000000460 chlorine Substances 0.000 claims abstract description 3
AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
239000011737 fluorine Substances 0.000 claims abstract description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
229910021529 ammonia Inorganic materials 0.000 claims description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
229960001760 dimethyl sulfoxide Drugs 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 11
LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
150000001735 carboxylic acids Chemical class 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
239000000243 solution Substances 0.000 description 6
150000001412 amines Chemical class 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
-1 cyano-substituted cyclopropane Chemical class 0.000 description 2
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
YCSKLPVYSJOCMO-UHFFFAOYSA-N 1-cyano-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate;dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1.CC1(C)C(C=C(Cl)Cl)C1(C#N)C([O-])=O YCSKLPVYSJOCMO-UHFFFAOYSA-N 0.000 description 1
QUBRLGZRCKCFDY-UHFFFAOYSA-N 1-cyano-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1(C#N)C(O)=O QUBRLGZRCKCFDY-UHFFFAOYSA-N 0.000 description 1
HFUWHULRJBGIQJ-UHFFFAOYSA-N 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonitrile Chemical compound CC1(C)C(C=C(Cl)Cl)C1C#N HFUWHULRJBGIQJ-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
238000004458 analytical method 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
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

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)

CA279,843A 1976-06-22 1977-06-03 Preparation de cyclopropanecarbonitriles Expired CA1085873A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB25895/76		1976-06-22
GB2589576A GB1580202A (en)	1976-06-22	1976-06-22	Process for the preparation of cyclopropanecarbonitriles

Publications (1)

Publication Number	Publication Date
CA1085873A true CA1085873A (fr)	1980-09-16

Family

ID=10235106

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA279,843A Expired CA1085873A (fr)	1976-06-22	1977-06-03	Preparation de cyclopropanecarbonitriles

Country Status (11)

Country	Link
JP (1)	JPS52156838A (fr)
BE (1)	BE855693A (fr)
BR (1)	BR7703996A (fr)
CA (1)	CA1085873A (fr)
CH (1)	CH628326A5 (fr)
DE (1)	DE2727612C2 (fr)
DK (1)	DK155829C (fr)
FR (1)	FR2355810A1 (fr)
GB (1)	GB1580202A (fr)
IT (1)	IT1080224B (fr)
NL (1)	NL188639C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2606635A1 (de) *	1976-02-19	1977-08-25	Bayer Ag	Verfahren zur herstellung von 2,2-dimethyl-3-(2',2'-dichlorvinyl) -cyclopropan-1-carbonsaeure

1976
- 1976-06-22 GB GB2589576A patent/GB1580202A/en not_active Expired
1977
- 1977-06-03 CA CA279,843A patent/CA1085873A/fr not_active Expired
- 1977-06-15 BE BE1008192A patent/BE855693A/xx not_active IP Right Cessation
- 1977-06-20 FR FR7718842A patent/FR2355810A1/fr active Granted
- 1977-06-20 BR BR7703996A patent/BR7703996A/pt unknown
- 1977-06-20 CH CH752577A patent/CH628326A5/de not_active IP Right Cessation
- 1977-06-20 DK DK271777A patent/DK155829C/da not_active IP Right Cessation
- 1977-06-20 DE DE19772727612 patent/DE2727612C2/de not_active Expired
- 1977-06-20 NL NL7706754A patent/NL188639C/xx not_active IP Right Cessation
- 1977-06-20 IT IT2486777A patent/IT1080224B/it active
- 1977-06-20 JP JP7226077A patent/JPS52156838A/ja active Pending

Also Published As

Publication number	Publication date
DK155829B (da)	1989-05-22
DK271777A (da)	1977-12-23
IT1080224B (it)	1985-05-16
NL188639B (nl)	1992-03-16
FR2355810B1 (fr)	1978-10-20
DE2727612C2 (de)	1986-03-06
JPS52156838A (en)	1977-12-27
FR2355810A1 (fr)	1978-01-20
NL188639C (nl)	1992-08-17
CH628326A5 (en)	1982-02-26
GB1580202A (en)	1980-11-26
DK155829C (da)	1989-10-02
DE2727612A1 (de)	1978-01-05
NL7706754A (nl)	1977-12-27
BR7703996A (pt)	1978-04-25
BE855693A (nl)	1977-12-15

Legal Events

Date	Code	Title	Description
1997-09-16	MKEX	Expiry

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