CH701181B1 - Verfahren zur Herstellung von polyhalogeniertem Perhalogenalkylanilin. - Google Patents

Verfahren zur Herstellung von polyhalogeniertem Perhalogenalkylanilin. Download PDF

Info

Publication number: CH701181B1
Authority: CH; Switzerland
Prior art keywords: perhaloalkylaniline; trifluoromethylaniline; polyhalogenated; chloro; ammonia
Prior art date: 2009-11-12

Application number

CH01098/10A

Other languages

German (de)

English (en)

Inventor

Keki Hormusji Gharda

Original Assignee

Keki Hormusji Gharda

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.)

2009-11-12

Filing date

2010-07-05

Publication date

2010-12-15

2010-07-05 Application filed by Keki Hormusji Gharda filed Critical Keki Hormusji Gharda

2010-12-15 Publication of CH701181B1 publication Critical patent/CH701181B1/de

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 40
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims abstract description 21
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 17
229910021529 ammonia Inorganic materials 0.000 claims abstract description 11
239000003513 alkali Substances 0.000 claims abstract description 10
235000003270 potassium fluoride Nutrition 0.000 claims abstract description 10
239000011698 potassium fluoride Substances 0.000 claims abstract description 10
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims abstract description 10
239000003795 chemical substances by application Substances 0.000 claims abstract description 9
150000004820 halides Chemical class 0.000 claims abstract description 9
KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims abstract description 8
230000002140 halogenating effect Effects 0.000 claims abstract description 8
239000002798 polar solvent Substances 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 7
238000006243 chemical reaction Methods 0.000 claims description 25
ITNMAZSPBLRJLU-UHFFFAOYSA-N 2,6-dichloro-4-(trifluoromethyl)aniline Chemical group NC1=C(Cl)C=C(C(F)(F)F)C=C1Cl ITNMAZSPBLRJLU-UHFFFAOYSA-N 0.000 claims description 16
238000004519 manufacturing process Methods 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 11
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 claims 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
XILPLWOGHPSJBK-UHFFFAOYSA-N 1,2-dichloro-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(Cl)=C1 XILPLWOGHPSJBK-UHFFFAOYSA-N 0.000 description 22
MBBUTABXEITVNY-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1Cl MBBUTABXEITVNY-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 14
VKTTYIXIDXWHKW-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1Cl VKTTYIXIDXWHKW-UHFFFAOYSA-N 0.000 description 13
QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 description 12
ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 10
238000005915 ammonolysis reaction Methods 0.000 description 10
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
230000014759 maintenance of location Effects 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000000470 constituent Substances 0.000 description 6
238000004817 gas chromatography Methods 0.000 description 6
239000012429 reaction media Substances 0.000 description 6
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 5
239000005749 Copper compound Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
150000001880 copper compounds Chemical class 0.000 description 5
-1 halide salt Chemical class 0.000 description 5
150000001502 aryl halides Chemical class 0.000 description 4
238000005660 chlorination reaction Methods 0.000 description 4
238000005194 fractionation Methods 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
239000000376 reactant Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
230000026030 halogenation Effects 0.000 description 3
238000005658 halogenation reaction Methods 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
229910001220 stainless steel Inorganic materials 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
JCVFAVWOYUUQOZ-UHFFFAOYSA-N N,2,3-trichloro-N-(trifluoromethyl)aniline Chemical compound ClC=1C(=C(N(C(F)(F)F)Cl)C=CC1)Cl JCVFAVWOYUUQOZ-UHFFFAOYSA-N 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
150000001879 copper Chemical class 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 description 2
229910000069 nitrogen hydride Inorganic materials 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
PVRJKVZQZVDIQH-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl PVRJKVZQZVDIQH-UHFFFAOYSA-N 0.000 description 1
GZWGTVZRRFPVAS-UHFFFAOYSA-N 1-isocyanato-2-(trifluoromethyl)benzene Chemical class FC(F)(F)C1=CC=CC=C1N=C=O GZWGTVZRRFPVAS-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
XKYLCLMYQDFGKO-UHFFFAOYSA-N 1-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(C(F)(F)F)C=C1 XKYLCLMYQDFGKO-UHFFFAOYSA-N 0.000 description 1
QVGXDVUFEAAYHW-UHFFFAOYSA-N 2,3-dichloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC(Cl)=C1Cl QVGXDVUFEAAYHW-UHFFFAOYSA-N 0.000 description 1
HFHAVERNVFNSHL-UHFFFAOYSA-N 2-chloro-1,3-dinitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1Cl HFHAVERNVFNSHL-UHFFFAOYSA-N 0.000 description 1
OVENUGPMQDFGLE-UHFFFAOYSA-N 3-chloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(Cl)=CC(C(F)(F)F)=C1 OVENUGPMQDFGLE-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910001508 alkali metal halide Inorganic materials 0.000 description 1
150000008045 alkali metal halides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000001500 aryl chlorides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001503 aryl iodides Chemical class 0.000 description 1
150000003842 bromide salts Chemical class 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000020335 dealkylation Effects 0.000 description 1
238000006900 dealkylation reaction Methods 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
IYVXSTYCOQHADR-UHFFFAOYSA-N n-[2-(trifluoromethyl)phenyl]nitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1C(F)(F)F IYVXSTYCOQHADR-UHFFFAOYSA-N 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
239000003973 paint Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000005891 transamination reaction Methods 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

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

CH01098/10A 2009-11-12 2010-07-05 Verfahren zur Herstellung von polyhalogeniertem Perhalogenalkylanilin. CH701181B1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IN2611MU2009		2009-11-12

Publications (1)

Publication Number	Publication Date
CH701181B1 true CH701181B1 (de)	2010-12-15

Family

ID=42168027

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH01098/10A CH701181B1 (de)	2009-11-12	2010-07-05	Verfahren zur Herstellung von polyhalogeniertem Perhalogenalkylanilin.

Country Status (5)

Country	Link
AR (1)	AR078133A1 (pt)
AU (1)	AU2010100312A6 (pt)
BR (1)	BRPI1002140A2 (pt)
CH (1)	CH701181B1 (pt)
WO (1)	WO2011058576A1 (pt)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2010100462A4 (en) *	2010-03-03	2010-06-17	Keki Hormusji Gharda	A process for the synthesis of Fipronil
CN102746108A (zh) *	2012-08-01	2012-10-24	山东道可化学有限公司	3,4-二氯三氟甲苯的制备方法
CN107311873B (zh) *	2017-07-24	2019-12-10	连云港埃森化学有限公司	一种制备99％含量2，6-二氯-4-三氟甲基苯胺的方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0543633B1 (en) *	1991-11-20	1996-10-30	Sumitomo Chemical Company Limited	Process for producing 4-amino-3-fluorobenzotrifluoride

2010
- 2010-04-02 AU AU2010100312A patent/AU2010100312A6/en not_active Expired
- 2010-06-08 WO PCT/IN2010/000381 patent/WO2011058576A1/en not_active Ceased
- 2010-06-24 BR BRPI1002140-0A patent/BRPI1002140A2/pt active Search and Examination
- 2010-06-28 AR ARP100102303A patent/AR078133A1/es active IP Right Grant
- 2010-07-05 CH CH01098/10A patent/CH701181B1/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU2010100312A6 (en)	2010-08-12
WO2011058576A1 (en)	2011-05-19
AR078133A1 (es)	2011-10-19
BRPI1002140A2 (pt)	2012-03-13
AU2010100312A4 (en)	2010-05-13

Legal Events

Date

Code

Title

Description

2011-03-15

PFA

Name/firm changed

Owner name: KEKI HORMUSJI GHARDA

Free format text: KEKI HORMUSJI GHARDA#GHARDA HOUSE, 48 HILL ROAD BANDRA (WEST)#MUMBAI 400 050, MAHARASHTRA (IN) -TRANSFER TO- KEKI HORMUSJI GHARDA#GHARDA HOUSE, 48 HILL ROAD BANDRA (WEST)#MUMBAI 400 050, MAHARASHTRA (IN)

2025-02-28

PL

Patent ceased

Publication	Publication Date	Title
EP2303828B1 (de)	2014-07-30	Verfahren zur herstellung von substituierten biphenylen
CH701924B1 (de)	2011-03-15	Verfahren zur Synthese von Fipronil.
EP0562435B1 (de)	1995-06-07	Verfahren zur Herstellung von 3,5-Difluoranilin
CH701181B1 (de)	2010-12-15	Verfahren zur Herstellung von polyhalogeniertem Perhalogenalkylanilin.
EP0083442B1 (de)	1986-08-20	Verfahren zur Herstellung von 2,4,6-Trichloranilin
DE2313496C3 (de)	1979-07-19	Verfahren zur Herstellung von m- und p- Phenylendiamin
EP1418163A1 (de)	2004-05-12	Verfahren zur Herstellung von Polyhalogenalkanen
DE2614240C3 (de)	1980-03-06	Verfahren zur Herstellung von Acylcyaniden
EP0539765B1 (de)	1994-07-20	Verfahren zur Herstellung von 2,4-Dichlorfluorbenzol
EP0667337B1 (de)	1998-01-21	Verfahren zur Herstellung von Fluoranilinen
DE3148971A1 (de)	1982-07-29	Verfahren zur herstellung von monomethylhydrazin
EP0059241A1 (de)	1982-09-08	Verfahren zur Herstellung von aromatischen Sulfohalogeniden
CH701180B1 (de)	2010-12-15	Verfahren zur Synthese von polyhalogenierten Perhalogenalkylanilinverbindungen.
EP1099686B1 (de)	2007-04-04	Verfahren zur Herstellung von Trifluormethylanilinen
DE3909142A1 (de)	1990-10-04	Verfahren zur herstellung von aminen
DE3308659C2 (pt)	1991-08-22
WO2004022520A1 (de)	2004-03-18	Verfahren zum herstellen von phthalsäuredichlorid
DE3431826A1 (de)	1986-03-13	Verfahren zur herstellung aromatischer bromverbindungen
WO2003051817A1 (de)	2003-06-26	Verfahren zur herstellung von aminen
DE2216115A1 (de)	1973-10-04	Verfahren zur herstellung von mund p-phenylendiamin
DE3043206A1 (de)	1982-07-01	Verfahren zur herstellung von 4-chlor-2,6-dialkylanilinen
DE3875501T2 (de)	1993-03-18	Verfahren zur herstellung eines benzoesaeurederivates.
DE102004058519A1 (de)	2006-06-14	Verfahren zum Herstellen von 3-Halophthalsäuredichloriden
DE2616612C2 (de)	1984-04-12	Verfahren zur Herstellung von Chlorsulfonylbenzoylchlorid
DE3308658C2 (pt)	1988-01-28