CA1270490A - Methode de chloration selective de la 2-chloro-5- (trichloromethyl) pyridine en position 3 - Google Patents

Methode de chloration selective de la 2-chloro-5- (trichloromethyl) pyridine en position 3

Info

Publication number: CA1270490A
Authority: CA; Canada
Prior art keywords: pyridine; trichloromethyl; chloro; dichloro; reaction
Prior art date: 1986-05-20
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 - Lifetime

Application number

CA000509460A

Other languages

English (en)

Inventor

Thomas J. Dietsche

Paula L. Humphreys

James L. Bixby

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.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

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.)

1986-05-20

Filing date

1986-05-20

Publication date

1990-06-19

1986-05-20 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1986-05-20 Priority to CA000509460A priority Critical patent/CA1270490A/fr

1990-06-19 Application granted granted Critical

1990-06-19 Publication of CA1270490A publication Critical patent/CA1270490A/fr

2007-06-19 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

VLJIVLGVKMTBOD-UHFFFAOYSA-N 2-chloro-5-(trichloromethyl)pyridine Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=N1 VLJIVLGVKMTBOD-UHFFFAOYSA-N 0.000 title claims abstract description 22
238000000034 method Methods 0.000 title claims description 21
XVBWGQSXLITICX-UHFFFAOYSA-N 2,3-dichloro-5-(trichloromethyl)pyridine Chemical compound ClC1=CC(C(Cl)(Cl)Cl)=CN=C1Cl XVBWGQSXLITICX-UHFFFAOYSA-N 0.000 claims abstract description 16
238000005660 chlorination reaction Methods 0.000 claims abstract description 6
239000007791 liquid phase Substances 0.000 claims abstract description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 9
239000011541 reaction mixture Substances 0.000 claims description 8
229910052742 iron Inorganic materials 0.000 claims description 5
150000003222 pyridines Chemical class 0.000 claims description 3
XLZHJPALXIYDGU-UHFFFAOYSA-N 2,6-dichloro-3-(trichloromethyl)pyridine Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C(Cl)=N1 XLZHJPALXIYDGU-UHFFFAOYSA-N 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
239000003863 metallic catalyst Substances 0.000 claims description 2
239000012808 vapor phase Substances 0.000 claims description 2
ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims 1
239000003054 catalyst Substances 0.000 abstract description 11
150000001875 compounds Chemical class 0.000 abstract description 3
239000003905 agrochemical Substances 0.000 abstract description 2
238000002360 preparation method Methods 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 22
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
239000000460 chlorine Substances 0.000 description 13
229910052801 chlorine Inorganic materials 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000004821 distillation Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
229910015400 FeC13 Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000007670 refining Methods 0.000 description 2
GPAKJVMKNDXBHH-UHFFFAOYSA-N 2,3,6-trichloropyridine Chemical compound ClC1=CC=C(Cl)C(Cl)=N1 GPAKJVMKNDXBHH-UHFFFAOYSA-N 0.000 description 1
SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
230000000135 prohibitive effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000036647 reaction Effects 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1

Landscapes

Pyridine Compounds (AREA)

CA000509460A 1986-05-20 1986-05-20 Methode de chloration selective de la 2-chloro-5- (trichloromethyl) pyridine en position 3 Expired - Lifetime CA1270490A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000509460A CA1270490A (fr)	1986-05-20	1986-05-20	Methode de chloration selective de la 2-chloro-5- (trichloromethyl) pyridine en position 3

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000509460A CA1270490A (fr)	1986-05-20	1986-05-20	Methode de chloration selective de la 2-chloro-5- (trichloromethyl) pyridine en position 3

Publications (1)

Publication Number	Publication Date
CA1270490A true CA1270490A (fr)	1990-06-19

Family

ID=4133163

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000509460A Expired - Lifetime CA1270490A (fr)	1986-05-20	1986-05-20	Methode de chloration selective de la 2-chloro-5- (trichloromethyl) pyridine en position 3

Country Status (1)

Country	Link
CA (1)	CA1270490A (fr)

1986
- 1986-05-20 CA CA000509460A patent/CA1270490A/fr not_active Expired - Lifetime

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Legal Events

Date	Code	Title	Description
2007-06-19	MKEX	Expiry