ZA200104895B - Method for preparing polyhalogenated paratrifluoromethylanilines. - Google Patents

Method for preparing polyhalogenated paratrifluoromethylanilines. Download PDF

Info

Publication number: ZA200104895B
Authority: ZA; South Africa
Prior art keywords: preparation; process according; formula; reaction; alkali metal
Prior art date: 1998-12-17

Application number

ZA200104895A

Other languages

English (en)

Inventor

Jean-Erick Ancel

Eliane Damand

Original Assignee

Aventis Cropscience Sa

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.)

1998-12-17

Filing date

2001-06-14

Publication date

2003-01-07

2001-06-14 Application filed by Aventis Cropscience Sa filed Critical Aventis Cropscience Sa

2003-01-07 Publication of ZA200104895B publication Critical patent/ZA200104895B/en

Links

238000000034 method Methods 0.000 title claims description 36
238000002360 preparation method Methods 0.000 claims description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
239000011541 reaction mixture Substances 0.000 claims description 9
239000000376 reactant Substances 0.000 claims description 8
229910021529 ammonia Inorganic materials 0.000 claims description 7
229910001508 alkali metal halide Inorganic materials 0.000 claims description 6
150000008045 alkali metal halides Chemical class 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
239000003495 polar organic solvent Substances 0.000 claims description 5
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 description 19
150000001448 anilines Chemical group 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
ITNMAZSPBLRJLU-UHFFFAOYSA-N 2,6-dichloro-4-(trifluoromethyl)aniline Chemical compound NC1=C(Cl)C=C(C(F)(F)F)C=C1Cl ITNMAZSPBLRJLU-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
-1 alkali metal amide Chemical class 0.000 description 4
150000001555 benzenes Chemical class 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000004821 distillation Methods 0.000 description 4
SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical class FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
FBKFIAIRSQOXJR-UHFFFAOYSA-N 1,2,3-trichloro-5-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=C(Cl)C(Cl)=C1 FBKFIAIRSQOXJR-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000000605 extraction Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
UQYVMQFUNZXYEK-UHFFFAOYSA-N 2-bromo-1,3-dichloro-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(Br)=C1Cl UQYVMQFUNZXYEK-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001875 compounds Chemical group 0.000 description 2
PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
150000005226 trifluoromethylbenzenes Chemical class 0.000 description 2
238000005406 washing Methods 0.000 description 2
NKCROTQPQZXJOL-UHFFFAOYSA-N 2,6-dichloro-3-(trifluoromethyl)aniline Chemical compound NC1=C(Cl)C=CC(C(F)(F)F)=C1Cl NKCROTQPQZXJOL-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical class NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
241001484259 Lacuna Species 0.000 description 1
229910001513 alkali metal bromide Inorganic materials 0.000 description 1
229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000203 mixture Substances 0.000 description 1
VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Polymers [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 description 1
230000006675 polyamination Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyethers (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

ZA200104895A 1998-12-17 2001-06-14 Method for preparing polyhalogenated paratrifluoromethylanilines. ZA200104895B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9816164A FR2787445B1 (fr)	1998-12-17	1998-12-17	Procede de preparation de para-trifluoromethylanilines polyhalogenees

Publications (1)

Publication Number	Publication Date
ZA200104895B true ZA200104895B (en)	2003-01-07

Family

ID=9534265

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200104895A ZA200104895B (en)	1998-12-17	2001-06-14	Method for preparing polyhalogenated paratrifluoromethylanilines.

Country Status (25)

Country	Link
US (1)	US6479703B1 (de)
EP (1)	EP1140785B1 (de)
JP (1)	JP2002532453A (de)
KR (1)	KR100656728B1 (de)
CN (1)	CN1215041C (de)
AT (1)	ATE286013T1 (de)
AU (1)	AU769242B2 (de)
BG (1)	BG64948B1 (de)
BR (2)	BRPI9916280B8 (de)
CA (1)	CA2355358C (de)
CZ (1)	CZ302234B6 (de)
DE (1)	DE69922999T2 (de)
DK (1)	DK1140785T3 (de)
EA (1)	EA004922B1 (de)
ES (1)	ES2235538T3 (de)
FR (1)	FR2787445B1 (de)
HR (1)	HRP20010457B1 (de)
HU (1)	HU229275B1 (de)
IL (1)	IL143750A (de)
PL (1)	PL196252B1 (de)
SI (1)	SI1140785T1 (de)
SK (1)	SK285288B6 (de)
TW (1)	TW576714B (de)
WO (1)	WO2000035851A1 (de)
ZA (1)	ZA200104895B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2846325B1 (fr)	2002-10-25	2006-09-08	Bayer Cropscience Sa	Nouveau procede de preparation d'un intermediaire de synthese de pesticide
ITTO20030850A1 (it) *	2003-10-29	2005-04-30	Finchimica Srl	Procedimento per la preparazione di 4-ammino-3,5-dicloro-benzotrifloruro.
CN101165044B (zh) *	2006-10-19	2010-08-18	上海赫腾精细化工有限公司	2,6-二氯-对三氟甲基苯胺的制备方法
CN101289400B (zh) *	2008-03-24	2011-07-20	浙江巍华化工有限公司	一种合成2,6-二氯-4-三氟甲基苯胺的方法
CN101289401B (zh) *	2008-03-24	2011-07-20	浙江巍华化工有限公司	一种制备2,6-二氯-4-三氟甲基苯胺的方法
AU2010100462A4 (en)	2010-03-03	2010-06-17	Keki Hormusji Gharda	A process for the synthesis of Fipronil

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE292238C (de)	1914-06-23
US4096185A (en) *	1976-01-08	1978-06-20	E. I. Du Pont De Nemours And Company	Preparation of p-aminobenzotrifluoride
US4197259A (en)	1979-02-22	1980-04-08	Ppg Industries, Inc.	Preparation of haloaniline
DE3431827A1 (de)	1984-08-30	1986-03-13	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von chlor-o-nitroanilinen
ES2022443B3 (es) *	1986-03-04	1991-12-01	Ciba-Geigy Ag	Utilizacion fungicida de un derivado de cianopirrol.
DE3737983A1 (de) *	1987-11-09	1989-08-03	Bayer Ag	3-cyano-4-phenyl-pyrrol-derivate
EP0543633B1 (de)	1991-11-20	1996-10-30	Sumitomo Chemical Company Limited	Verfahren zur Herstellung von 4-Amino-3-Fluorobenzotrifluorid
NZ246433A (en) *	1991-12-20	1995-10-26	Schering Corp	Process for the preparation of 2-methyl-3-trifluoromethyl-aniline and a pivalanilide intermediate thereof
JPH05255206A (ja)	1992-03-12	1993-10-05	Toray Ind Inc	フルオロアニリンの製造方法

1998
- 1998-12-17 FR FR9816164A patent/FR2787445B1/fr not_active Expired - Fee Related
1999
- 1999-12-10 IL IL14375099A patent/IL143750A/en not_active IP Right Cessation
- 1999-12-10 BR BRPI9916280A patent/BRPI9916280B8/pt unknown
- 1999-12-10 PL PL349434A patent/PL196252B1/pl unknown
- 1999-12-10 HU HU0104648A patent/HU229275B1/hu unknown
- 1999-12-10 AU AU15690/00A patent/AU769242B2/en not_active Ceased
- 1999-12-10 SK SK854-2001A patent/SK285288B6/sk not_active IP Right Cessation
- 1999-12-10 BR BRPI9916280-6A patent/BR9916280B1/pt not_active IP Right Cessation
- 1999-12-10 SI SI9930735T patent/SI1140785T1/xx unknown
- 1999-12-10 DE DE69922999T patent/DE69922999T2/de not_active Expired - Lifetime
- 1999-12-10 KR KR1020017007577A patent/KR100656728B1/ko active IP Right Grant
- 1999-12-10 JP JP2000588113A patent/JP2002532453A/ja active Pending
- 1999-12-10 CA CA2355358A patent/CA2355358C/fr not_active Expired - Lifetime
- 1999-12-10 CZ CZ20012124A patent/CZ302234B6/cs not_active IP Right Cessation
- 1999-12-10 AT AT99958293T patent/ATE286013T1/de active
- 1999-12-10 US US09/868,349 patent/US6479703B1/en not_active Expired - Lifetime
- 1999-12-10 WO PCT/FR1999/003090 patent/WO2000035851A1/fr active IP Right Grant
- 1999-12-10 CN CNB998145696A patent/CN1215041C/zh not_active Expired - Lifetime
- 1999-12-10 ES ES99958293T patent/ES2235538T3/es not_active Expired - Lifetime
- 1999-12-10 EA EA200100667A patent/EA004922B1/ru not_active IP Right Cessation
- 1999-12-10 DK DK99958293T patent/DK1140785T3/da active
- 1999-12-10 EP EP99958293A patent/EP1140785B1/de not_active Expired - Lifetime
- 1999-12-16 TW TW088122115A patent/TW576714B/zh not_active IP Right Cessation
2001
- 2001-06-14 ZA ZA200104895A patent/ZA200104895B/en unknown
- 2001-06-15 HR HR20010457A patent/HRP20010457B1/xx not_active IP Right Cessation
- 2001-06-25 BG BG105647A patent/BG64948B1/bg unknown

Also Published As

Publication number	Publication date
SI1140785T1 (en)	2005-04-30
CN1215041C (zh)	2005-08-17
BG64948B1 (bg)	2006-10-31
DK1140785T3 (da)	2005-03-14
CZ20012124A3 (cs)	2001-11-14
KR20010102956A (ko)	2001-11-17
EP1140785B1 (de)	2004-12-29
CZ302234B6 (cs)	2011-01-05
ES2235538T3 (es)	2005-07-01
WO2000035851A1 (fr)	2000-06-22
EP1140785A1 (de)	2001-10-10
AU1569000A (en)	2000-07-03
CN1330625A (zh)	2002-01-09
HUP0104648A3 (en)	2004-09-28
FR2787445B1 (fr)	2001-01-19
DE69922999D1 (de)	2005-02-03
BR9916280B1 (pt)	2012-08-07
DE69922999T2 (de)	2005-05-19
HRP20010457B1 (en)	2010-02-28
PL196252B1 (pl)	2007-12-31
HRP20010457A2 (en)	2002-06-30
BRPI9916280B1 (de)	2012-08-07
PL349434A1 (en)	2002-07-29
BG105647A (en)	2002-02-28
ATE286013T1 (de)	2005-01-15
SK285288B6 (sk)	2006-10-05
KR100656728B1 (ko)	2006-12-12
IL143750A0 (en)	2002-04-21
JP2002532453A (ja)	2002-10-02
CA2355358A1 (fr)	2000-06-22
HU229275B1 (en)	2013-10-28
BRPI9916280B8 (pt)	2022-07-05
FR2787445A1 (fr)	2000-06-23
CA2355358C (fr)	2010-02-16
TW576714B (en)	2004-02-21
IL143750A (en)	2004-09-27
HUP0104648A2 (hu)	2002-03-28
SK8542001A3 (en)	2001-12-03
EA200100667A1 (ru)	2001-12-24
BRPI9916280A (de)	2001-12-04
EA004922B1 (ru)	2004-10-28
US6479703B1 (en)	2002-11-12
AU769242B2 (en)	2004-01-22
BR9916280A (pt)	2001-12-04

Publication	Publication Date	Title
AU769242B2 (en)	2004-01-22	Method for preparing polyhalogenated paratrifluoromethylanilines
US3435074A (en)	1969-03-25	Process for producing nitrodiarylamines
HU214818B (hu)	1998-10-28	Eljárás (o-nitro-fenil)-ciklopropil-keton herbicid köztitermék előállítására
US4410724A (en)	1983-10-18	Process for production of o-(2,6-dichloroanilino)-phenylacetic acid
US5233082A (en)	1993-08-03	Method of making 3-hydroxy-2,4,5-trifluorobenzoic acid
MXPA01006142A (en)	2002-06-05	Method for preparing polyhalogenated paratrifluoromethylanilines
JP2840560B2 (ja)	1998-12-24	塩化プロパルギルアンモニウム誘導体の製造方法
US5536877A (en)	1996-07-16	Preparation of arylbenzylamines
US4609759A (en)	1986-09-02	Process for preparing amino-2, 4-dinitroaromatic herbicides
US4289906A (en)	1981-09-15	Chemical process for preparing methylene bis-anilines
GB2026475A (en)	1980-02-06	Method of preparing n-alkyl benzothiazolone derivatives
US4987266A (en)	1991-01-22	Process for the manufacture of nitrophenetole
US3965183A (en)	1976-06-22	Preparation of p-fluoro-m-phenylenediamine
JPS5826905B2 (ja)	1983-06-06	ジフエニルアミン化合物の改良製造法
US4224245A (en)	1980-09-23	Method of making 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds which are useful as agricultural fungicides
JPS6270350A (ja)	1987-03-31	ベンゾフエノン誘導体の製造法
CA2461574C (en)	2011-01-11	Process for preparing vanillylamine hyrochloride
FR2549828A1 (fr)	1985-02-01	Procede de preparation de chlorhydrate de trimethobenzamide
JPH03232843A (ja)	1991-10-16	アルキルアリルアミンの精製方法
NO801549L (no)	1980-12-01	Fremgangsmaate for fremstilling av pyrrolinderivater
JPH07233130A (ja)	1995-09-05	アミノ安息香酸アルキルエステルの製造法
JPH08119954A (ja)	1996-05-14	フェニルピペラジン類の製造方法
JPH083126A (ja)	1996-01-09	Ｎ，ｏ−ジメチルヒドロキシルアミンの製造方法
JPS58180461A (ja)	1983-10-21	ｍ−ニトロフエニルアルキルエ−テルの製造方法
JPH0597781A (ja)	1993-04-20	アルキルアミノフエノールの製造法