CA1070333A - Procede pour la preparation de 1,1-dihalo-1,3-dienes - Google Patents

Procede pour la preparation de 1,1-dihalo-1,3-dienes

Info

Publication number: CA1070333A
Authority: CA; Canada
Prior art keywords: preparation; tertiary amine; dihalo; general formula; quinoline
Prior art date: 1975-06-02
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

CA251,627A

Other languages

English (en)

Inventor

Jan H. Wevers

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.)

1975-06-02

Filing date

1976-05-03

Publication date

1980-01-22

1976-05-03 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1980-01-22 Application granted granted Critical

1980-01-22 Publication of CA1070333A publication Critical patent/CA1070333A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 19
238000002360 preparation method Methods 0.000 title claims abstract description 7
150000003512 tertiary amines Chemical class 0.000 claims abstract description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052794 bromium Inorganic materials 0.000 claims abstract description 3
239000000460 chlorine Substances 0.000 claims abstract description 3
229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
229910052740 iodine Inorganic materials 0.000 claims abstract description 3
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
NEPBEPYINQHTKZ-UHFFFAOYSA-N 1,1,1,3-tetrachloro-4-methylpentane Chemical compound CC(C)C(Cl)CC(Cl)(Cl)Cl NEPBEPYINQHTKZ-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000005270 trialkylamine group Chemical group 0.000 claims description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine group Chemical group C(CCC)N(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
239000002917 insecticide Substances 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
YYOLVILSZOVWLS-UHFFFAOYSA-N 1,1-dichloro-4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C(Cl)Cl YYOLVILSZOVWLS-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
BWQCTTJXTNBYSJ-UHFFFAOYSA-N 1,1,1,3-tetrachloropentane Chemical compound CCC(Cl)CC(Cl)(Cl)Cl BWQCTTJXTNBYSJ-UHFFFAOYSA-N 0.000 description 1
BOGRNZQRTNVZCZ-UHFFFAOYSA-N 1,2-dimethyl-butadiene Natural products CC=C(C)C=C BOGRNZQRTNVZCZ-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
-1 phenyl-substituted pyridine Chemical class 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)

CA251,627A 1975-06-02 1976-05-03 Procede pour la preparation de 1,1-dihalo-1,3-dienes Expired CA1070333A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB23772/75A GB1536685A (en)	1975-06-02	1975-06-02	Process for the preparation of 1,1-dihalo-1,3-dienes

Publications (1)

Publication Number	Publication Date
CA1070333A true CA1070333A (fr)	1980-01-22

Family

ID=10201085

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA251,627A Expired CA1070333A (fr)	1975-06-02	1976-05-03	Procede pour la preparation de 1,1-dihalo-1,3-dienes

Country Status (11)

Country	Link
JP (1)	JPS51143602A (fr)
BE (1)	BE842180A (fr)
BR (1)	BR7603469A (fr)
CA (1)	CA1070333A (fr)
CH (1)	CH620185A5 (fr)
DE (1)	DE2624340C2 (fr)
FR (1)	FR2313334A1 (fr)
GB (1)	GB1536685A (fr)
IL (1)	IL49689A (fr)
IT (1)	IT1061059B (fr)
NL (1)	NL7605738A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1086778A (fr) *	1976-11-18	1980-09-30	Stauffer Chemical Company	Obtention a l'echelle industrielle de 1,1-dihalo-4- methyl-1,3-pentadienes
GB2062623B (en) *	1979-09-24	1983-06-29	Stauffer Chemical Co	Process for the preparation of 1,1-dihalo-4-methyl-1,3-pentadienes

1975
- 1975-06-02 GB GB23772/75A patent/GB1536685A/en not_active Expired
1976
- 1976-05-03 CA CA251,627A patent/CA1070333A/fr not_active Expired
- 1976-05-25 BE BE1007412A patent/BE842180A/fr not_active IP Right Cessation
- 1976-05-28 NL NL7605738A patent/NL7605738A/xx not_active Application Discontinuation
- 1976-05-31 IT IT23798/76A patent/IT1061059B/it active
- 1976-05-31 CH CH680976A patent/CH620185A5/de not_active IP Right Cessation
- 1976-05-31 IL IL49689A patent/IL49689A/xx unknown
- 1976-05-31 BR BR3469/76A patent/BR7603469A/pt unknown
- 1976-05-31 FR FR7616354A patent/FR2313334A1/fr active Granted
- 1976-05-31 JP JP51062452A patent/JPS51143602A/ja active Pending
- 1976-05-31 DE DE2624340A patent/DE2624340C2/de not_active Expired

Also Published As

Publication number	Publication date
IL49689A0 (en)	1976-07-30
NL7605738A (nl)	1976-12-06
BE842180A (fr)	1976-11-25
IL49689A (en)	1978-10-31
IT1061059B (it)	1982-10-20
DE2624340C2 (de)	1984-08-16
GB1536685A (en)	1978-12-20
FR2313334B1 (fr)	1978-11-17
DE2624340A1 (de)	1976-12-16
BR7603469A (pt)	1977-01-04
JPS51143602A (en)	1976-12-10
FR2313334A1 (fr)	1976-12-31
CH620185A5 (en)	1980-11-14

Legal Events

Date	Code	Title	Description
1997-01-22	MKEX	Expiry

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JPH0610158B2 (ja)	1994-02-09	３−フルオロ安息香酸類の製造方法
JPS6053039B2 (ja)	1985-11-22	Ｎ−アセチル／イラミン酸誘導体およびその製造方法
US5525722A (en)	1996-06-11	Process for producing biocozamycin benzoate
US4007216A (en)	1977-02-08	2-Methoxy-4-methyl-3-oxo-cyclopent-1-ene-1,4-dicarboxylic acid esters
JPH04273887A (ja)	1992-09-30	モノハロアルカノイルフェロセンの合成方法
KR910003635B1 (ko)	1991-06-07	2-(2-나프틸옥시)프로피온아닐리드 유도체의 제조방법
MXPA05004124A (es)	2005-06-24	Proceso para producir compuestos de acetileno.
CA1045150A (fr)	1978-12-26	Acide trans, trans-musconique
EP0064021B1 (fr)	1985-09-25	Procédé de synthèse d'acides carboxyliques et d'alcools à lonque chaîne
US4638082A (en)	1987-01-20	Method of producing the p-chlorophenol ester of p-chlorophenoxyisobutyric acid
JP2522926B2 (ja)	1996-08-07	２′−デオキシ−５−トリフルオロメチルウリジン誘導体の製造方法
SU1198066A1 (ru)	1985-12-15	Способ получени N-ацетил-1,2,3,4-тетрагидро-6-бромхинолона-4
KR910004605B1 (ko)	1991-07-08	2,4-디클로로플루오로벤젠의 제조방법
CA1049035A (fr)	1979-02-20	Procede pour la preparation de triesters et produits obtenus par ce procede
KR860000263B1 (ko)	1986-03-22	아세토니트릴로부터 디-치환된 니트릴 유도체의 제조방법
KR800000992B1 (ko)	1980-09-19	0-(2, 6-디클로로 아닐리노) 페닐 초산의 제조방법
JP3085698B2 (ja)	2000-09-11	チオフェン誘導体およびその製造方法
JPH0415232B2 (fr)	1992-03-17