CS226444B2 - Method of preparing 2,3-dichloro-5-trichloromethylpyridine - Google Patents

Method of preparing 2,3-dichloro-5-trichloromethylpyridine Download PDF

Info

Publication number: CS226444B2
Authority: CS; Czechoslovakia
Prior art keywords: trichloromethylpyridine; chloro; dichloro; catalyst; tungsten
Prior art date: 1981-03-12

Application number

CS821716A

Other languages

Czech (cs)

English (en)

Inventor

John A Werner

Charles A Wilson

Craig E Mixan

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.)

1981-03-12

Filing date

1982-03-12

Publication date

1984-03-19

1982-03-12 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1984-03-19 Publication of CS226444B2 publication Critical patent/CS226444B2/cs

Links

XVBWGQSXLITICX-UHFFFAOYSA-N 2,3-dichloro-5-(trichloromethyl)pyridine Chemical compound ClC1=CC(C(Cl)(Cl)Cl)=CN=C1Cl XVBWGQSXLITICX-UHFFFAOYSA-N 0.000 title claims abstract description 9
238000000034 method Methods 0.000 title claims description 14
239000003054 catalyst Substances 0.000 claims abstract description 18
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 11
239000000460 chlorine Substances 0.000 claims abstract description 11
229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
VLJIVLGVKMTBOD-UHFFFAOYSA-N 2-chloro-5-(trichloromethyl)pyridine Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=N1 VLJIVLGVKMTBOD-UHFFFAOYSA-N 0.000 claims abstract description 10
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052750 molybdenum Inorganic materials 0.000 claims abstract description 8
239000011733 molybdenum Substances 0.000 claims abstract description 8
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052721 tungsten Inorganic materials 0.000 claims abstract description 6
239000010937 tungsten Substances 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 3
GICWIDZXWJGTCI-UHFFFAOYSA-I molybdenum pentachloride Chemical compound Cl[Mo](Cl)(Cl)(Cl)Cl GICWIDZXWJGTCI-UHFFFAOYSA-I 0.000 claims description 6
KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 claims description 6
FQNHWXHRAUXLFU-UHFFFAOYSA-N carbon monoxide;tungsten Chemical group [W].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] FQNHWXHRAUXLFU-UHFFFAOYSA-N 0.000 claims description 3
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
229910052707 ruthenium Inorganic materials 0.000 claims 1
150000003304 ruthenium compounds Chemical class 0.000 abstract 1
239000000203 mixture Substances 0.000 description 11
239000007788 liquid Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000004817 gas chromatography Methods 0.000 description 7
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
ABNQGNFVSFKJGI-UHFFFAOYSA-N 2,3-dichloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=C(Cl)C(Cl)=C1 ABNQGNFVSFKJGI-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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
230000008901 benefit Effects 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
DNDPLEAVNVOOQZ-UHFFFAOYSA-N 2,3,4,5,6-pentachloropyridine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=C1Cl DNDPLEAVNVOOQZ-UHFFFAOYSA-N 0.000 description 1
-1 2,3-dihydro-5-trichloromethylpyridine Chemical compound 0.000 description 1
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 description 1
SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 1
NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
238000010923 batch production Methods 0.000 description 1
239000011449 brick Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003303 ruthenium Chemical class 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/20—Carbonyls
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
- B01J2531/64—Molybdenum
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
- B01J2531/66—Tungsten
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Inorganic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Pyridine Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS821716A 1981-03-12 1982-03-12 Method of preparing 2,3-dichloro-5-trichloromethylpyridine CS226444B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/243,166 US4331811A (en)	1981-03-12	1981-03-12	Preparation of 2,3-dichloro-5-trichloromethylpyridine

Publications (1)

Publication Number	Publication Date
CS226444B2 true CS226444B2 (en)	1984-03-19

Family

ID=22917601

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS821716A CS226444B2 (en)	1981-03-12	1982-03-12	Method of preparing 2,3-dichloro-5-trichloromethylpyridine

Country Status (19)

Country	Link
US (1)	US4331811A (es)
EP (1)	EP0060462B1 (es)
JP (1)	JPS6017788B2 (es)
KR (1)	KR860000584B1 (es)
AR (1)	AR229175A1 (es)
AU (1)	AU549161B2 (es)
BR (1)	BR8201194A (es)
CA (1)	CA1162550A (es)
CS (1)	CS226444B2 (es)
DE (1)	DE3261579D1 (es)
DK (1)	DK157855C (es)
ES (1)	ES510354A0 (es)
GB (1)	GB2094788B (es)
HU (1)	HU186912B (es)
IL (1)	IL64939A (es)
NZ (1)	NZ199723A (es)
SU (1)	SU1151202A3 (es)
YU (1)	YU52082A (es)
ZA (1)	ZA82716B (es)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS56125369A (en) *	1980-03-07	1981-10-01	Ishihara Sangyo Kaisha Ltd	Preparation of 3-halogeno-5-trifluoromethylpyridine compound
JPS5877863A (ja) *	1981-11-04	1983-05-11	Ishihara Sangyo Kaisha Ltd	３―クロロ―５―トリフルオロメチルピリジン系化合物の製造方法
US4701532A (en) *	1983-03-25	1987-10-20	The Dow Chemical Company	Method of selectively chlorinating 2-chloro-5-(trichloromethyl) pyridine in the 3-position
US4483993A (en) *	1983-04-08	1984-11-20	Kalama Chemical, Inc.	Production of polychlorinated pyridine mixtures by liquid phase chlorination of beta-picoline or beta-picoline hydrochloride
FR2569191B1 (fr) *	1984-08-20	1987-07-10	Solvay	Procede pour la preparation de derives chlores de composes pyridiniques et initiateurs radicalaires utilises dans ce procede
US4939263A (en) *	1989-09-28	1990-07-03	The Dow Chemical Company	Control of isomer distribution in a chlorination process
DE69014101T2 (de) *	1989-12-26	1995-03-23	Sagami Chem Res	Katalysator zur hydrierung, dehydrosilylierung oder hydrosilylierung und dessen verwendung.
US5319088A (en) *	1991-11-26	1994-06-07	Dowelanco	Selective gas phase chlorination of polychlorinated β-picolines to produce 2,3,5,6-tetrachloropyridine and its precursors
FI95219C (sv) *	1992-04-30	1996-01-10	Kwh Pipe Ab Oy	Svetsningsförfarande vid framställning av spirallindat rör och svetshuvud för utförande av förfarandet
DK3008040T3 (en) *	2013-06-14	2017-07-31	Cheminova As	Process for preparing 2,3-dichloro-5- (trichloromethyl) pyridine.
CN104557683B (zh) *	2013-10-09	2016-11-02	李波	2，3-二氯-5-三氟甲基吡啶的制备方法
JP2017537887A (ja) *	2014-10-22	2017-12-21	アクシアルオハイオ、インコーポレイテッド	多価モリブデン化合物の存在下で塩化炭化水素を生成するためのプロセス
CN104529882A (zh) *	2014-12-26	2015-04-22	扬州大学	一种2,3-二氯-5-三氯甲基吡啶的合成方法
CN107935920A (zh) *	2017-11-30	2018-04-20	山东汇盟生物科技有限公司	2‑氟‑3‑氯‑5‑三氟甲基吡啶的制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL285543A (es) *	1961-11-15
US3186994A (en) *	1962-10-18	1965-06-01	Dow Chemical Co	Polychloropyridines
US3244722A (en) *	1964-01-28	1966-04-05	Dow Chemical Co	Certain ethers of (trichloromethyl) pyridine compounds
US3420833A (en) *	1967-09-08	1969-01-07	Dow Chemical Co	Vapor phase production of polychlorinated compounds
US3538100A (en) *	1968-03-15	1970-11-03	Olin Corp	Process for preparing highly chlorinated pyridines
US3732230A (en) *	1970-12-07	1973-05-08	Dow Chemical Co	Liquid phase polychlorination of pyridine hydrochlorides
CA1089468A (en) *	1978-04-24	1980-11-11	The Dow Chemical Company	Process for preparing 2,3,5,6-tetrachloropyridine and pentachloropyridine
US4256894A (en) *	1978-04-24	1981-03-17	The Dow Chemical Company	Preparation of chlorinated pyridines
CA1084936A (en) *	1978-06-19	1980-09-02	Dow Chemical Company	Preparation of polychlorinated pyridines from 2,4- dichloro-6-(trichloromethyl) pyridines

1981
- 1981-03-12 US US06/243,166 patent/US4331811A/en not_active Expired - Fee Related
1982
- 1982-01-29 CA CA000395224A patent/CA1162550A/en not_active Expired
- 1982-02-04 ZA ZA82716A patent/ZA82716B/xx unknown
- 1982-02-04 AU AU80201/82A patent/AU549161B2/en not_active Ceased
- 1982-02-05 IL IL64939A patent/IL64939A/xx unknown
- 1982-02-12 GB GB8204260A patent/GB2094788B/en not_active Expired
- 1982-02-12 NZ NZ199723A patent/NZ199723A/en unknown
- 1982-03-03 BR BR8201194A patent/BR8201194A/pt unknown
- 1982-03-05 DE DE8282101747T patent/DE3261579D1/de not_active Expired
- 1982-03-05 EP EP82101747A patent/EP0060462B1/en not_active Expired
- 1982-03-10 YU YU00520/82A patent/YU52082A/xx unknown
- 1982-03-11 ES ES510354A patent/ES510354A0/es active Granted
- 1982-03-11 DK DK107482A patent/DK157855C/da not_active IP Right Cessation
- 1982-03-11 KR KR8201049A patent/KR860000584B1/ko not_active Expired
- 1982-03-11 AR AR288711A patent/AR229175A1/es active
- 1982-03-11 HU HU82753A patent/HU186912B/hu not_active IP Right Cessation
- 1982-03-11 SU SU823407196A patent/SU1151202A3/ru active
- 1982-03-12 JP JP57039262A patent/JPS6017788B2/ja not_active Expired
- 1982-03-12 CS CS821716A patent/CS226444B2/cs unknown

Also Published As

Publication number	Publication date
GB2094788B (en)	1984-10-31
NZ199723A (en)	1984-12-14
DK107482A (da)	1982-09-13
IL64939A (en)	1984-09-30
DK157855C (da)	1990-07-30
US4331811A (en)	1982-05-25
BR8201194A (pt)	1983-01-18
GB2094788A (en)	1982-09-22
ZA82716B (en)	1983-09-28
ES8303339A1 (es)	1983-02-01
ES510354A0 (es)	1983-02-01
HU186912B (en)	1985-10-28
SU1151202A3 (ru)	1985-04-15
KR860000584B1 (ko)	1986-05-17
AR229175A1 (es)	1983-06-30
YU52082A (en)	1985-03-20
EP0060462A1 (en)	1982-09-22
EP0060462B1 (en)	1984-12-19
DK157855B (da)	1990-02-26
JPS57165367A (en)	1982-10-12
AU8020182A (en)	1982-09-16
CA1162550A (en)	1984-02-21
DE3261579D1 (en)	1985-01-31
JPS6017788B2 (ja)	1985-05-07
AU549161B2 (en)	1986-01-16
KR830009026A (ko)	1983-12-17
IL64939A0 (en)	1982-04-30

Publication	Publication Date	Title
US3186994A (en)	1965-06-01	Polychloropyridines
CS226444B2 (en)	1984-03-19	Method of preparing 2,3-dichloro-5-trichloromethylpyridine
US4256894A (en)	1981-03-17	Preparation of chlorinated pyridines
US3538100A (en)	1970-11-03	Process for preparing highly chlorinated pyridines
US3732230A (en)	1973-05-08	Liquid phase polychlorination of pyridine hydrochlorides
JPH0794441B2 (ja)	1995-10-11	５−クロロメチルピリジンの製法
JP2806998B2 (ja)	1998-09-30	置換された‐２‐クロロ‐ピリジン類の製造方法
US4752644A (en)	1988-06-21	Vapor phase production of chlorinated pyridines from alpha-picoline
US4420618A (en)	1983-12-13	Process for producing 5-chloro-β-trifluoromethylpyridines
US5468863A (en)	1995-11-21	Process for the preparation of substituted 2,3-difluoropyridines
JPH0231076B2 (es)	1990-07-11
EP0092117B1 (en)	1987-07-15	Process for producing chloronicotinic acid compounds
JPS639495B2 (es)	1988-02-29
US4563530A (en)	1986-01-07	Preparation of fluoropyridines
EP0246349A1 (en)	1987-11-25	Method of selectively chlorinating 2-chloro-5-(Trichloromethyl) pyridine in the 3-position
US4705859A (en)	1987-11-10	Polychloropyridine production from polychloro-2,3-lutidines
US4968807A (en)	1990-11-06	Preparation of symmetrical tetrachloropyridine from chlorinated beta(trichloromethyl) pyridines employing a catalyst
US6051714A (en)	2000-04-18	Processes for dechlorinating pyridines
KR100331155B1 (ko)	2002-09-25	2,6-디클로로피리딘의제조방법
NO820371L (no)	1982-08-10	Fremgangsmaate for fremstilling av pirbuterol og analoger derav
EP0204848B1 (en)	1989-11-23	Preparation of symmetrical tetrachloropyridine from chlorinated beta - (trichloromethyl) pyridines employing a catalyst
JPH0219108B2 (es)	1990-04-27
EP0007160A1 (en)	1980-01-23	Preparation of polychlorinated pyridines from 2,4-dichloro-6-(trichloromethyl)pyridine
US4891108A (en)	1990-01-02	Process for preparing tetrahalopyridines
JPS6130666B2 (es)	1986-07-15