IL45647A - Process for the manufacture of cyclopropanecarbonitrile - Google Patents

Process for the manufacture of cyclopropanecarbonitrile

Info

Publication number: IL45647A
Authority: IL; Israel
Prior art keywords: parts; cyclopropanecarbonitrile; reaction; sodium; product
Prior art date: 1973-09-13

Application number

IL45647A

Other languages

English (en)

Other versions

IL45647A0 (en

Original Assignee

Ciba Geigy Ag

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.)

1973-09-13

Filing date

1974-09-12

Publication date

1977-10-31

1974-09-12 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1974-11-29 Publication of IL45647A0 publication Critical patent/IL45647A0/xx

1977-10-31 Publication of IL45647A publication Critical patent/IL45647A/en

Links

238000000034 method Methods 0.000 title claims description 28
AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 title claims description 17
238000004519 manufacturing process Methods 0.000 title description 3
150000004703 alkoxides Chemical class 0.000 claims description 12
ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 4-chlorobutanenitrile Chemical compound ClCCCC#N ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 0.000 claims description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
239000003513 alkali Substances 0.000 claims description 6
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical class [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 4
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
-1 ethoxides Chemical class 0.000 claims description 3
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 2
239000003795 chemical substances by application Substances 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
239000006227 byproduct Substances 0.000 claims 1
239000000047 product Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
238000010992 reflux Methods 0.000 description 12
238000004821 distillation Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000013019 agitation Methods 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
235000011118 potassium hydroxide Nutrition 0.000 description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 3
DESWHHQXGYOJKY-UHFFFAOYSA-N benzene cyclopropanecarbonitrile Chemical compound C1(CC1)C#N.C1=CC=CC=C1 DESWHHQXGYOJKY-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000010908 decantation Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
238000007086 side reaction Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
CQPGDDAKTTWVDD-UHFFFAOYSA-N 4-bromobutanenitrile Chemical compound BrCCCC#N CQPGDDAKTTWVDD-UHFFFAOYSA-N 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000011149 active material Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
229960004217 benzyl alcohol Drugs 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Chemical group 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
MAVLRJDQJZJTQP-UHFFFAOYSA-N n-(cyclopropylmethyl)propan-1-amine Chemical compound CCCNCC1CC1 MAVLRJDQJZJTQP-UHFFFAOYSA-N 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000004064 recycling Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000013341 scale-up Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Toxicology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL45647A 1973-09-13 1974-09-12 Process for the manufacture of cyclopropanecarbonitrile IL45647A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US00397211A US3853942A (en)	1973-09-13	1973-09-13	Process for the manufacture of cyclopropa-necarbonitrile

Publications (2)

Publication Number	Publication Date
IL45647A0 IL45647A0 (en)	1974-11-29
IL45647A true IL45647A (en)	1977-10-31

Family

ID=23570273

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL45647A IL45647A (en)	1973-09-13	1974-09-12	Process for the manufacture of cyclopropanecarbonitrile

Country Status (12)

Country	Link
US (1)	US3853942A (fr)
JP (1)	JPS5757467B2 (fr)
BE (1)	BE880265Q (fr)
BR (1)	BR7407605D0 (fr)
CA (1)	CA1021349A (fr)
CH (1)	CH597164A5 (fr)
DE (1)	DE2443142C2 (fr)
FR (1)	FR2243934B1 (fr)
GB (1)	GB1477499A (fr)
IL (1)	IL45647A (fr)
IT (1)	IT1021327B (fr)
NL (1)	NL179726C (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3974199A (en) *	1975-06-16	1976-08-10	The Dow Chemical Company	Process for production of cyclopropylcyanide
US4205009A (en) *	1979-02-07	1980-05-27	Velsicol Chemical Corporation	Process for the preparation of cyclopropylcyanide
US5380911A (en) *	1993-12-02	1995-01-10	American Cyanamid Company	Process for the manufacture of cyclopropylnitrile
US5502234A (en) *	1995-07-17	1996-03-26	Eastman Chemical Company	Process for the preparation and separation of cyclopropanecarbonitrile
US6222058B1 (en)	1998-03-30	2001-04-24	Eastman Chemical Company	Process for the manufacture of cyclopropanecarbonitrile
EP1243578A1 (fr)	2001-02-23	2002-09-25	Kuraray Co., Ltd.	Procédé de préparation de cyclopropanecarbonitrile

1973
- 1973-09-13 US US00397211A patent/US3853942A/en not_active Expired - Lifetime
1974
- 1974-08-21 CH CH1143674A patent/CH597164A5/xx not_active IP Right Cessation
- 1974-09-04 CA CA208,474A patent/CA1021349A/en not_active Expired
- 1974-09-10 DE DE2443142A patent/DE2443142C2/de not_active Expired
- 1974-09-10 NL NLAANVRAGE7412037,A patent/NL179726C/xx not_active IP Right Cessation
- 1974-09-11 JP JP49104821A patent/JPS5757467B2/ja not_active Expired
- 1974-09-12 IT IT27231/74A patent/IT1021327B/it active
- 1974-09-12 BR BR7605/74A patent/BR7407605D0/pt unknown
- 1974-09-12 FR FR7430861A patent/FR2243934B1/fr not_active Expired
- 1974-09-12 IL IL45647A patent/IL45647A/en unknown
- 1974-09-12 GB GB3984774A patent/GB1477499A/en not_active Expired
1979
- 1979-11-27 BE BE0/198290A patent/BE880265Q/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB1477499A (en)	1977-06-22
NL179726C (nl)	1986-11-03
DE2443142C2 (de)	1985-10-03
US3853942A (en)	1974-12-10
JPS5053351A (fr)	1975-05-12
FR2243934B1 (fr)	1976-10-22
JPS5757467B2 (fr)	1982-12-04
DE2443142A1 (de)	1975-03-20
NL179726B (nl)	1986-06-02
IT1021327B (it)	1978-01-30
BR7407605D0 (pt)	1975-07-08
CH597164A5 (fr)	1978-03-31
CA1021349A (en)	1977-11-22
FR2243934A1 (fr)	1975-04-11
BE880265Q (fr)	1980-03-17
NL7412037A (nl)	1975-03-17
IL45647A0 (en)	1974-11-29

Publication	Publication Date	Title
US2342101A (en)	1944-02-22	Preparation of dihydro mucononitrile and product
US3711549A (en)	1973-01-16	Process for manufacturing cyclopropylamine
US2436311A (en)	1948-02-17	Preparation of n, n'ethyleneurea
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US3853942A (en)	1974-12-10	Process for the manufacture of cyclopropa-necarbonitrile
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US5508396A (en)	1996-04-16	Process for preparing n-alkyllactams
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CA1224493A (fr)	1987-07-21	Fabrication de nitrodiarylamines
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KR100250415B1 (ko)	2000-09-01	고순도 1,3-디알킬-2-이미다졸리디논의 제조방법
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US2792395A (en)	1957-05-14	Preparation of guanamines
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US3190909A (en)	1965-06-22	Preparation of alpha, omegadicyanoolefins
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US2678319A (en)	1954-05-11	Preparation of 2,3-dihalotetrahydro-2-methylfurans
US3742063A (en)	1973-06-26	Dihydroxybutanones
US2429391A (en)	1947-10-21	Bis (carboxy methyl propyl) sulfide
JPS6337779B2 (fr)	1988-07-27
JPS5850991B2 (ja)	1983-11-14	オキシランの製造方法
JPH0729994B2 (ja)	1995-04-05	Ｎ−アルキルアルキレンジアミンの製造方法
JP2867633B2 (ja)	1999-03-08	フリルプロパルギルカルビノール類の製造方法
US3210426A (en)	1965-10-05	Preparation of iminobisalkylamines