DD149061A5 - Verfahren zur herstellung m-chlorsubstituierter aniline - Google Patents

Verfahren zur herstellung m-chlorsubstituierter aniline Download PDF

Info

Publication number: DD149061A5
Authority: DD; German Democratic Republic
Prior art keywords: chlorine; hydrogen; formula; item; points
Prior art date: 1979-02-15

Application number

DD80219035A

Other languages

German (de)

English (en)

Inventor

Georges Cordier

Original Assignee

Rhone Poulenc Agrochimie

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.)

1979-02-15

Filing date

1980-02-13

Publication date

1981-06-24

1980-02-13 Application filed by Rhone Poulenc Agrochimie filed Critical Rhone Poulenc Agrochimie

1981-06-24 Publication of DD149061A5 publication Critical patent/DD149061A5/de

Links

229910052801 chlorine Inorganic materials 0.000 title claims abstract description 16
239000000460 chlorine Substances 0.000 title claims abstract description 15
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title description 4
238000004519 manufacturing process Methods 0.000 title description 4
238000000034 method Methods 0.000 claims abstract description 39
239000001257 hydrogen Substances 0.000 claims abstract description 17
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
150000001768 cations Chemical class 0.000 claims abstract description 14
239000007791 liquid phase Substances 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
229910052797 bismuth Inorganic materials 0.000 claims abstract description 3
229910052753 mercury Inorganic materials 0.000 claims abstract description 3
229910052709 silver Inorganic materials 0.000 claims abstract description 3
229910052716 thallium Inorganic materials 0.000 claims abstract description 3
229910052718 tin Inorganic materials 0.000 claims abstract description 3
239000003054 catalyst Substances 0.000 claims description 20
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
-1 m-chloro-substituted anilines Chemical class 0.000 claims description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
229910000510 noble metal Inorganic materials 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
229910001385 heavy metal Inorganic materials 0.000 claims description 8
239000012429 reaction media Substances 0.000 claims description 8
229910052751 metal Inorganic materials 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 7
230000000737 periodic effect Effects 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
229910052763 palladium Inorganic materials 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
239000002609 medium Substances 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
239000001301 oxygen Chemical group 0.000 claims description 3
229910052760 oxygen Chemical group 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
239000012736 aqueous medium Substances 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
150000002500 ions Chemical class 0.000 claims description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
239000004332 silver Substances 0.000 claims description 2
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
150000005181 nitrobenzenes Chemical class 0.000 abstract description 2
150000001448 anilines Chemical class 0.000 abstract 2
238000006298 dechlorination reaction Methods 0.000 abstract 1
229910052745 lead Inorganic materials 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
239000002904 solvent Substances 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical class NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-UHFFFAOYSA-N 0.000 description 2
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical class NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001491 aromatic compounds Chemical class 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
YBCSBMLIXWHLQI-UHFFFAOYSA-N 1,2-dichloro-3-methoxy-4-nitrobenzene Chemical compound COC1=C(Cl)C(Cl)=CC=C1[N+]([O-])=O YBCSBMLIXWHLQI-UHFFFAOYSA-N 0.000 description 1
CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
LBKQVYCKFHARBV-UHFFFAOYSA-N 1,2-dichloro-4-nitro-5-phenoxybenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=CC=C1 LBKQVYCKFHARBV-UHFFFAOYSA-N 0.000 description 1
NTBYINQTYWZXLH-UHFFFAOYSA-N 1,2-dichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1 NTBYINQTYWZXLH-UHFFFAOYSA-N 0.000 description 1
KTPPCTQPGJFQHB-UHFFFAOYSA-N 1,2-dichloro-5-methoxy-3-nitrobenzene Chemical compound COC1=CC(Cl)=C(Cl)C([N+]([O-])=O)=C1 KTPPCTQPGJFQHB-UHFFFAOYSA-N 0.000 description 1
PXQYVHVDNPLNNM-UHFFFAOYSA-N 1,3-dichloro-2-methoxy-4-nitrobenzene Chemical compound COC1=C(Cl)C=CC([N+]([O-])=O)=C1Cl PXQYVHVDNPLNNM-UHFFFAOYSA-N 0.000 description 1
RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 description 1
YAXBAPKUQSMNNU-UHFFFAOYSA-N 1,5-dichlorocyclohexa-2,4-dien-1-amine Chemical class NC1(Cl)CC(Cl)=CC=C1 YAXBAPKUQSMNNU-UHFFFAOYSA-N 0.000 description 1
KHCZSJXTDDHLGJ-UHFFFAOYSA-N 2,3,4,5,6-pentachloroaniline Chemical compound NC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl KHCZSJXTDDHLGJ-UHFFFAOYSA-N 0.000 description 1
HEZIOZBMPKPOER-UHFFFAOYSA-N 2,3-dimethoxyaniline Chemical compound COC1=CC=CC(N)=C1OC HEZIOZBMPKPOER-UHFFFAOYSA-N 0.000 description 1
NJZMXYAVRVWZAS-UHFFFAOYSA-N 2,5-dichloro-1-methoxy-3-nitrobenzene Chemical compound COC1=CC(Cl)=CC([N+]([O-])=O)=C1Cl NJZMXYAVRVWZAS-UHFFFAOYSA-N 0.000 description 1
JHZWCHORDSEJQD-UHFFFAOYSA-N 2,5-dichloro-3-methoxyaniline Chemical compound COC1=CC(Cl)=CC(N)=C1Cl JHZWCHORDSEJQD-UHFFFAOYSA-N 0.000 description 1
PLVBBUUBVVJOIB-UHFFFAOYSA-N 2,5-dichloro-4-methylaniline Chemical compound CC1=CC(Cl)=C(N)C=C1Cl PLVBBUUBVVJOIB-UHFFFAOYSA-N 0.000 description 1
AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
NOLQSBARNJXSOO-UHFFFAOYSA-N 2-benzyl-3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1CC1=CC=CC=C1 NOLQSBARNJXSOO-UHFFFAOYSA-N 0.000 description 1
UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 1
LTKJFXIFJLXFNJ-UHFFFAOYSA-N 3-benzyl-1,2,5-trichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C=C(Cl)C(Cl)=C1CC1=CC=CC=C1 LTKJFXIFJLXFNJ-UHFFFAOYSA-N 0.000 description 1
LVFXXXPXOSABGF-UHFFFAOYSA-N 3-chloro-2-phenoxyaniline Chemical compound NC1=CC=CC(Cl)=C1OC1=CC=CC=C1 LVFXXXPXOSABGF-UHFFFAOYSA-N 0.000 description 1
XQVCBOLNTSUFGD-UHFFFAOYSA-N 3-chloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1Cl XQVCBOLNTSUFGD-UHFFFAOYSA-N 0.000 description 1
XLAVBRTYEPFKSD-UHFFFAOYSA-N 3-chloro-5-methoxyaniline Chemical compound COC1=CC(N)=CC(Cl)=C1 XLAVBRTYEPFKSD-UHFFFAOYSA-N 0.000 description 1
XUZCJDBXXYJXDD-UHFFFAOYSA-N 3-chloro-5-methylaniline Chemical compound CC1=CC(N)=CC(Cl)=C1 XUZCJDBXXYJXDD-UHFFFAOYSA-N 0.000 description 1
WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 1
SXEBHIMOUHBBOS-UHFFFAOYSA-N 5-chloro-2-phenoxyaniline Chemical compound NC1=CC(Cl)=CC=C1OC1=CC=CC=C1 SXEBHIMOUHBBOS-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
238000013329 compounding Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000005695 dehalogenation reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
DQNOIKMHTBFYTD-UHFFFAOYSA-N n,n,2,3-tetrachloroaniline Chemical compound ClN(Cl)C1=CC=CC(Cl)=C1Cl DQNOIKMHTBFYTD-UHFFFAOYSA-N 0.000 description 1
NDPOGQHCFNMYTR-UHFFFAOYSA-N n,n,2-trimethoxyaniline Chemical compound CON(OC)C1=CC=CC=C1OC NDPOGQHCFNMYTR-UHFFFAOYSA-N 0.000 description 1
NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
GBECUEIQVRDUKB-UHFFFAOYSA-M thallium monochloride Chemical compound [Tl]Cl GBECUEIQVRDUKB-UHFFFAOYSA-M 0.000 description 1
150000003568 thioethers 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
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

DD80219035A 1979-02-15 1980-02-13 Verfahren zur herstellung m-chlorsubstituierter aniline DD149061A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7904482A FR2449076A2 (fr)	1979-02-15	1979-02-15	Procede de preparation d'anilines metachlorees

Publications (1)

Publication Number	Publication Date
DD149061A5 true DD149061A5 (de)	1981-06-24

Family

ID=9222291

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80219035A DD149061A5 (de)	1979-02-15	1980-02-13	Verfahren zur herstellung m-chlorsubstituierter aniline

Country Status (17)

Country	Link
US (1)	US4340759A (da)
EP (1)	EP0015220B1 (da)
JP (1)	JPS5848542B2 (da)
AT (1)	ATE1006T1 (da)
BR (1)	BR8000911A (da)
CA (1)	CA1139315A (da)
DD (1)	DD149061A5 (da)
DE (1)	DE3060394D1 (da)
DK (1)	DK153391C (da)
ES (1)	ES488570A1 (da)
FR (1)	FR2449076A2 (da)
GB (1)	GB2043066A (da)
HU (1)	HU185213B (da)
IE (1)	IE49885B1 (da)
IL (1)	IL59191A (da)
SU (1)	SU1149871A3 (da)
YU (1)	YU42206B (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2487824A1 (fr) *	1980-08-01	1982-02-05	Rhone Poulenc Agrochimie	Procede de preparation selective d'anilines metachlorees
IL63297A (en) *	1980-08-01	1984-05-31	Rhone Poulenc Agrochimie	Selective preparation of meta-chloroanilines
DE3127026A1 (de) *	1981-07-09	1983-01-20	Bayer Ag, 5090 Leverkusen	Verrfahren zur herstellung von m-chlorsubstituiertenanilinen
FR2521132A1 (fr) *	1982-02-05	1983-08-12	Rhone Poulenc Agrochimie	Procede de preparation de metahalogeno-anilines
FR2532305A1 (fr) *	1982-08-24	1984-03-02	Rhone Poulenc Agrochimie	Procede de preparation d'anilines metachlorees

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3666813A (en) *	1969-08-27	1972-05-30	Engelhard Min & Chem	Process for preparing aromatic haloamines from aromatic nitroamines
BE792080A (fr) *	1971-11-30	1973-05-29	Rhone Progil	Procede de deshalogenation de composes aromatiques polyhalogenes
DE2503187C3 (de) *	1975-01-27	1979-05-31	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung durch Chlor meta-substituierte Aniline

1979
- 1979-02-15 FR FR7904482A patent/FR2449076A2/fr active Granted
1980
- 1980-01-22 IL IL59191A patent/IL59191A/xx unknown
- 1980-01-24 US US06/115,137 patent/US4340759A/en not_active Expired - Lifetime
- 1980-02-13 CA CA000345563A patent/CA1139315A/en not_active Expired
- 1980-02-13 IE IE276/80A patent/IE49885B1/en unknown
- 1980-02-13 GB GB8004747A patent/GB2043066A/en not_active Withdrawn
- 1980-02-13 DD DD80219035A patent/DD149061A5/de unknown
- 1980-02-13 YU YU380/80A patent/YU42206B/xx unknown
- 1980-02-14 ES ES488570A patent/ES488570A1/es not_active Expired
- 1980-02-14 SU SU802882800A patent/SU1149871A3/ru active
- 1980-02-14 DE DE8080420019T patent/DE3060394D1/de not_active Expired
- 1980-02-14 AT AT80420019T patent/ATE1006T1/de not_active IP Right Cessation
- 1980-02-14 JP JP55017164A patent/JPS5848542B2/ja not_active Expired
- 1980-02-14 BR BR8000911A patent/BR8000911A/pt unknown
- 1980-02-14 HU HU80336A patent/HU185213B/hu unknown
- 1980-02-14 EP EP80420019A patent/EP0015220B1/fr not_active Expired
- 1980-02-14 DK DK062780A patent/DK153391C/da active

Also Published As

Publication number	Publication date
DE3060394D1 (en)	1982-07-01
IL59191A (en)	1983-06-15
DK62780A (da)	1980-08-16
FR2449076A2 (fr)	1980-09-12
IE800276L (en)	1980-08-15
SU1149871A3 (ru)	1985-04-07
EP0015220B1 (fr)	1982-05-12
GB2043066A (en)	1980-10-01
YU38080A (en)	1983-01-21
DK153391C (da)	1988-11-28
IE49885B1 (en)	1986-01-08
CA1139315A (en)	1983-01-11
ES488570A1 (es)	1980-10-01
IL59191A0 (en)	1980-05-30
ATE1006T1 (de)	1982-05-15
BR8000911A (pt)	1980-10-29
US4340759A (en)	1982-07-20
JPS5848542B2 (ja)	1983-10-28
JPS55149232A (en)	1980-11-20
YU42206B (en)	1988-06-30
HU185213B (en)	1984-12-28
EP0015220A1 (fr)	1980-09-03
DK153391B (da)	1988-07-11
FR2449076B2 (da)	1983-05-20

Publication	Publication Date	Title
DE2549900A1 (de)	1977-05-12	Chlorierte aromatische amine
DE2118369A1 (de)	1971-10-28	Selektive Hydrierung von Nitroaromaten
DE2634419A1 (de)	1977-02-10	Verfahren zur herstellung von aromatischen aethern
DE2503187B2 (de)	1978-10-05	Verfahren zur Herstellung durch Chlor meta-substituierte Aniline
DE2316028B2 (de)	1979-08-09	Verfahren zur gleichzeitigen Verringerung des Gehalts an Verbindungen mit hydrolysierbarem Chlor und an sauer wirkenden Verbindungen in einem organischen Roh-Isocyanat
CH436326A (de)	1967-05-31	Verfahren zur Herstellung von Aminen
DE2816637A1 (de)	1978-10-26	Verfahren zur denitrosierung organischer n-nitrosamine
DE3443385C2 (da)	1987-05-27
DE3003960C2 (da)	1990-07-05
DD149061A5 (de)	1981-06-24	Verfahren zur herstellung m-chlorsubstituierter aniline
DE2436111C2 (de)	1983-10-27	Verfahren zur Herstellung eines Phenylendiamins
DD295339A5 (de)	1991-10-31	Verfahren zur hydrierung von halogenierten nitroaromaten in gegenwart einer schwefelverbindung
DE3856098T2 (de)	1998-05-07	Verfahren zur selektiven Reduktion von 2-Chinoxalinol-4-Oxiden zu 2-Chinoxalinolen
DE19720341C1 (de)	1998-08-27	Verfahren zur Herstellung von 3,5-Difluoranilin
DD149062A5 (de)	1981-06-24	Verfahren zur herstellung m-chlorsubstituierter aniline
DE2604276C2 (de)	1984-09-06	Verfahren zur &alpha;-Monochlorierung kernchlorierter Toluole
DD299175A5 (de)	1992-04-02	Verfahren zur hydrierung von halogenierten nitroaromatischen verbindungen in gegenwart von katalysatoren auf der grundlage von edelmetallen
DE2743610C3 (de)	1980-09-18	Verfahren zur Herstellung von chlorsubstituierten aromatischen Aminen
EP0479877B1 (de)	1994-10-12	Verfahren zur herstellung von n-alkyl-halogenanilinen
DD201584A5 (de)	1983-07-27	Verfahren zur selektiven herstellung m-chlorierter aniline
EP0051782B1 (de)	1984-05-23	Verfahren zur Herstellung von m-halogensubstituierten Anilinen
DE1493629A1 (de)	1969-03-13	Verfahren zur Herstellung von Halogenaminen
DE2844305C2 (da)	1988-01-21
DE2258769A1 (de)	1973-06-07	Verfahren zur herstellung von aromatischen halogenverbindungen
EP0396134A1 (de)	1990-11-07	Verfahren zur Herstellung von 5H-Dibenz (b,f) azepin