DD149062A5 - Verfahren zur herstellung m-chlorsubstituierter aniline - Google Patents

Verfahren zur herstellung m-chlorsubstituierter aniline Download PDF

Info

Publication number: DD149062A5
Authority: DD; German Democratic Republic
Prior art keywords: hydrogen; formula; catalyst; items; reaction
Prior art date: 1979-02-15

Application number

DD80219036A

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 DD149062A5 publication Critical patent/DD149062A5/de

Links

239000000460 chlorine Substances 0.000 title claims description 14
229910052801 chlorine Inorganic materials 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title claims description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title description 8
238000000034 method Methods 0.000 claims abstract description 51
239000001257 hydrogen Substances 0.000 claims abstract description 34
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
238000006243 chemical reaction Methods 0.000 claims abstract description 27
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 9
239000007791 liquid phase Substances 0.000 claims abstract description 9
239000003054 catalyst Substances 0.000 claims description 28
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
-1 m-chloro-substituted anilines Chemical class 0.000 claims description 14
239000012429 reaction media Substances 0.000 claims description 12
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical class NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 claims description 10
229910052763 palladium Inorganic materials 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
229910000510 noble metal Inorganic materials 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
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
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000002609 medium Substances 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
150000001555 benzenes Chemical class 0.000 claims description 3
150000002500 ions Chemical class 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
230000000737 periodic effect Effects 0.000 claims description 3
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
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
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
150000002431 hydrogen Chemical class 0.000 claims 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 1
229940006461 iodide ion Drugs 0.000 claims 1
KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 claims 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract description 14
150000001448 anilines Chemical class 0.000 abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
230000015572 biosynthetic process Effects 0.000 abstract 1
230000000382 dechlorinating effect Effects 0.000 abstract 1
150000005181 nitrobenzenes Chemical class 0.000 abstract 1
238000003786 synthesis reaction Methods 0.000 abstract 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 21
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 9
150000001412 amines Chemical class 0.000 description 7
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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
229910052786 argon Inorganic materials 0.000 description 5
DQNOIKMHTBFYTD-UHFFFAOYSA-N n,n,2,3-tetrachloroaniline Chemical compound ClN(Cl)C1=CC=CC(Cl)=C1Cl DQNOIKMHTBFYTD-UHFFFAOYSA-N 0.000 description 5
BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical class NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
229910052715 tantalum Inorganic materials 0.000 description 4
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 4
GBKZRUCVLTWAML-UHFFFAOYSA-N 2,3,4,5-tetrachloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C(Cl)=C1Cl GBKZRUCVLTWAML-UHFFFAOYSA-N 0.000 description 3
UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001649 bromium compounds Chemical class 0.000 description 3
229940071870 hydroiodic acid Drugs 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
KUWAAZMPJBFLEO-UHFFFAOYSA-N n,n,2-trichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1Cl KUWAAZMPJBFLEO-UHFFFAOYSA-N 0.000 description 3
DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000007858 starting material Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 2
GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
238000001816 cooling Methods 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
150000004694 iodide salts Chemical class 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
239000000463 material Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
QFQSBAMTGUKFKS-UHFFFAOYSA-N 1,2-dichloro-4-methoxy-5-nitrobenzene Chemical compound COC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O QFQSBAMTGUKFKS-UHFFFAOYSA-N 0.000 description 1
UXJDZKJRGJNGTM-UHFFFAOYSA-N 1,2-dichloro-4-nitro-3-phenoxybenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1OC1=CC=CC=C1 UXJDZKJRGJNGTM-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
IIHRBBRFSOLMCD-UHFFFAOYSA-N 1,4-dichloro-2-nitro-5-propylbenzene Chemical compound CCCC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl IIHRBBRFSOLMCD-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
VNHGETRQQSYUGZ-UHFFFAOYSA-N 1-nitro-2-phenoxybenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1 VNHGETRQQSYUGZ-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
JXWUMFLJRZJKAZ-UHFFFAOYSA-N 2,3-dichloro-1-methoxy-4-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C(Cl)=C1Cl JXWUMFLJRZJKAZ-UHFFFAOYSA-N 0.000 description 1
LZYMHTVWOMZPEO-UHFFFAOYSA-N 2,3-dichloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C(Cl)=C1Cl LZYMHTVWOMZPEO-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
VCMXIPGKIUDONN-UHFFFAOYSA-N 2,5-dichloro-4-methoxyaniline Chemical compound COC1=CC(Cl)=C(N)C=C1Cl VCMXIPGKIUDONN-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
YCJWTHYCBOTYAL-UHFFFAOYSA-N 2,5-dichloro-4-propylaniline Chemical compound CCCC1=CC(Cl)=C(N)C=C1Cl YCJWTHYCBOTYAL-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
XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
UNOXQGBIAVFVBH-UHFFFAOYSA-N 2-benzyl-5-chloroaniline Chemical compound NC1=CC(Cl)=CC=C1CC1=CC=CC=C1 UNOXQGBIAVFVBH-UHFFFAOYSA-N 0.000 description 1
XOGYQVITULCUGU-UHFFFAOYSA-N 3,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C(Cl)=C1 XOGYQVITULCUGU-UHFFFAOYSA-N 0.000 description 1
VPZJHTWLWKFPQW-UHFFFAOYSA-N 3-chloro-2-methoxyaniline Chemical compound COC1=C(N)C=CC=C1Cl VPZJHTWLWKFPQW-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
LBGGMEGRRIBANG-UHFFFAOYSA-N 3-chloro-4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1Cl LBGGMEGRRIBANG-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
XUZCJDBXXYJXDD-UHFFFAOYSA-N 3-chloro-5-methylaniline Chemical compound CC1=CC(N)=CC(Cl)=C1 XUZCJDBXXYJXDD-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical class NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-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
WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-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
LMKKQQBWNMUMOW-UHFFFAOYSA-N ClC1(C)C(C=C(C=C1)Cl)[N+](=O)[O-] Chemical compound ClC1(C)C(C=C(C=C1)Cl)[N+](=O)[O-] LMKKQQBWNMUMOW-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-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
239000003513 alkali Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
229940107816 ammonium iodide Drugs 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
WTKZCLKPWJFCEF-UHFFFAOYSA-N aniline tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.NC1=CC=CC=C1 WTKZCLKPWJFCEF-UHFFFAOYSA-N 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000004820 halides Chemical class 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
239000000203 mixture Substances 0.000 description 1
WWSPYAPXNNFYPE-UHFFFAOYSA-N n,n-dichloro-4-methylaniline Chemical compound CC1=CC=C(N(Cl)Cl)C=C1 WWSPYAPXNNFYPE-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
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000000376 reactant Substances 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
229960004889 salicylic acid Drugs 0.000 description 1
238000007789 sealing Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000000967 suction filtration 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
- C07C209/68—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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD80219036A 1979-02-15 1980-02-13 Verfahren zur herstellung m-chlorsubstituierter aniline DD149062A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7904481A FR2449075A1 (fr)	1979-02-15	1979-02-15	Procede de preparation d'anilines metachlorees

Publications (1)

Publication Number	Publication Date
DD149062A5 true DD149062A5 (de)	1981-06-24

Family

ID=9222290

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80219036A DD149062A5 (de)	1979-02-15	1980-02-13	Verfahren zur herstellung m-chlorsubstituierter aniline

Country Status (17)

Country	Link
US (1)	US4351959A (da)
EP (1)	EP0015219B1 (da)
JP (1)	JPS5848541B2 (da)
AT (1)	ATE398T1 (da)
BR (1)	BR8000918A (da)
CA (1)	CA1139314A (da)
DD (1)	DD149062A5 (da)
DE (1)	DE3060055D1 (da)
DK (1)	DK152667C (da)
ES (1)	ES488571A1 (da)
FR (1)	FR2449075A1 (da)
GB (1)	GB2041375A (da)
HU (1)	HU185215B (da)
IE (1)	IE49642B1 (da)
IL (1)	IL59297A (da)
SU (1)	SU1103793A3 (da)
YU (1)	YU42324B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL63297A (en) *	1980-08-01	1984-05-31	Rhone Poulenc Agrochimie	Selective preparation of meta-chloroanilines
DE3042242A1 (de) *	1980-11-08	1982-06-09	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von m-halogensubstituierten anilinen
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
CN117065668A (zh) *	2023-08-19	2023-11-17	浙江永合新材料科技有限公司	一种快速制备3,5-二氯苯胺的装置及方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3683025A (en) *	1969-05-06	1972-08-08	Henry W Pons	Hydrogenation of nitrobenzenes
US3546297A (en) *	1969-07-01	1970-12-08	Du Pont	Process for preparation of aromatic chloroamines
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 FR7904481A patent/FR2449075A1/fr active Granted
1980
- 1980-01-28 US US06/116,154 patent/US4351959A/en not_active Expired - Lifetime
- 1980-02-04 IL IL59297A patent/IL59297A/xx unknown
- 1980-02-12 SU SU802880051A patent/SU1103793A3/ru active
- 1980-02-13 GB GB8004749A patent/GB2041375A/en not_active Withdrawn
- 1980-02-13 CA CA000345562A patent/CA1139314A/en not_active Expired
- 1980-02-13 DD DD80219036A patent/DD149062A5/de unknown
- 1980-02-13 IE IE275/80A patent/IE49642B1/en unknown
- 1980-02-13 YU YU379/80A patent/YU42324B/xx unknown
- 1980-02-14 DK DK062680A patent/DK152667C/da not_active IP Right Cessation
- 1980-02-14 AT AT80420018T patent/ATE398T1/de active
- 1980-02-14 HU HU80338A patent/HU185215B/hu unknown
- 1980-02-14 ES ES488571A patent/ES488571A1/es not_active Expired
- 1980-02-14 EP EP80420018A patent/EP0015219B1/fr not_active Expired
- 1980-02-14 BR BR8000918A patent/BR8000918A/pt unknown
- 1980-02-14 DE DE8080420018T patent/DE3060055D1/de not_active Expired
- 1980-02-14 JP JP55017163A patent/JPS5848541B2/ja not_active Expired

Also Published As

Publication number	Publication date
YU42324B (en)	1988-08-31
DK62680A (da)	1980-08-16
IE800275L (en)	1980-08-15
US4351959A (en)	1982-09-28
DK152667B (da)	1988-04-11
FR2449075B1 (da)	1983-03-11
BR8000918A (pt)	1980-10-29
FR2449075A1 (fr)	1980-09-12
IL59297A0 (en)	1980-05-30
IL59297A (en)	1983-06-15
HU185215B (en)	1984-12-28
ES488571A1 (es)	1980-10-01
DE3060055D1 (en)	1982-01-07
YU37980A (en)	1983-01-21
GB2041375A (en)	1980-09-10
CA1139314A (en)	1983-01-11
JPS5848541B2 (ja)	1983-10-28
ATE398T1 (de)	1981-11-15
EP0015219A1 (fr)	1980-09-03
EP0015219B1 (fr)	1981-10-28
IE49642B1 (en)	1985-11-13
SU1103793A3 (ru)	1984-07-15
DK152667C (da)	1988-08-22
JPS55149231A (en)	1980-11-20

Publication	Publication Date	Title
DE2441650C3 (de)	1979-05-23	Verfahren zur Herstellung von halogenierten aromatischen primären Aminen
DE19600722A1 (de)	1997-07-17	Verfahren zur Herstellung von gegebenenfalls substituierten 4-Aminodiphenylaminen
DE2549900C3 (de)	1981-02-05	Verfahren zur Herstellung chlorierter aromatischer Amine
DE2308105B2 (de)	1978-07-13	Verfahren zur Herstellung eines halogenierten aromatischen Amins
DE2118369A1 (de)	1971-10-28	Selektive Hydrierung von Nitroaromaten
DE2615079A1 (de)	1976-10-28	Verfahren zur katalytischen reduktion von halogensubstituierten mononitroaromatischen kohlenwasserstoffen
DD149062A5 (de)	1981-06-24	Verfahren zur herstellung m-chlorsubstituierter aniline
DE3003960C2 (da)	1990-07-05
DE3443385C2 (da)	1987-05-27
DE3928329A1 (de)	1991-02-28	Verfahren zur herstellung von chlorsubstituierten aromatischen aminen
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
DE2820854A1 (de)	1979-11-22	Verfahren zur herstellung von p-hydroxyphenylessigsaeure
DD149061A5 (de)	1981-06-24	Verfahren zur herstellung m-chlorsubstituierter aniline
DD299175A5 (de)	1992-04-02	Verfahren zur hydrierung von halogenierten nitroaromatischen verbindungen in gegenwart von katalysatoren auf der grundlage von edelmetallen
DE68907969T2 (de)	1993-11-11	Katalytische Hydrierung von rohen methylenüberbrückten Polyphenylenaminen zur Herstellung von Polycyclohexylaminen.
EP1335041B1 (de)	2009-08-12	Verfahren zum Schutz von metallischen Werkstoffen in stark alkalischem Medium
DE856294C (de)	1952-11-20	Verfahren zur Herstellung ª‡,ª‰-ungesaettigter Carbonsaeuren und ihrer Abkoemmlinge
DE2835314A1 (de)	1979-03-01	Verfahren zur herstellung von o-phenylendiamin
DE2328757C3 (de)	1987-07-09	Verfahren zur Herstellung von Aminen
DE69508428T2 (de)	1999-07-22	Verfahren zur herstellung von fluoroanilinen aus fluoronitrobenzolen
DE2258769A1 (de)	1973-06-07	Verfahren zur herstellung von aromatischen halogenverbindungen
EP0051782B1 (de)	1984-05-23	Verfahren zur Herstellung von m-halogensubstituierten Anilinen
DD201584A5 (de)	1983-07-27	Verfahren zur selektiven herstellung m-chlorierter aniline
DE2416722B2 (de)	1978-05-11	Verfahren zur Herstellung von 2-Nitrohalogenophenolen