DD142331A5 - Verfahren zur herstellung von p-amino-diphenylamin - Google Patents

Verfahren zur herstellung von p-amino-diphenylamin Download PDF

Info

Publication number: DD142331A5
Authority: DD; German Democratic Republic
Prior art keywords: catalyst; reaction; solvent; palladium; platinum
Prior art date: 1978-03-11

Application number

DD79211479A

Other languages

German (de)

English (en)

Inventor

Hans-Georg Zengel

Manfred Bergfeld

Original Assignee

Akzo Nv

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.)

1978-03-11

Filing date

1979-03-08

Publication date

1980-06-18

1979-03-08 Application filed by Akzo Nv filed Critical Akzo Nv

1980-06-18 Publication of DD142331A5 publication Critical patent/DD142331A5/de

Links

238000000034 method Methods 0.000 title claims description 28
230000008569 process Effects 0.000 title claims description 16
ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title description 9
239000003054 catalyst Substances 0.000 claims description 30
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
239000002904 solvent Substances 0.000 claims description 24
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 17
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
229910052751 metal Inorganic materials 0.000 claims description 12
239000002184 metal Substances 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 10
238000005984 hydrogenation reaction Methods 0.000 claims description 9
229910052763 palladium Inorganic materials 0.000 claims description 9
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 8
229910052697 platinum Inorganic materials 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
150000002739 metals Chemical class 0.000 claims description 5
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
229910052707 ruthenium Inorganic materials 0.000 claims description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
229910052741 iridium Inorganic materials 0.000 claims description 3
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
229910052762 osmium Inorganic materials 0.000 claims description 3
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
229910052703 rhodium Inorganic materials 0.000 claims description 3
239000010948 rhodium Substances 0.000 claims description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
NRUVOKMCGYWODZ-UHFFFAOYSA-N sulfanylidenepalladium Chemical compound [Pd]=S NRUVOKMCGYWODZ-UHFFFAOYSA-N 0.000 claims description 3
JOKPITBUODAHEN-UHFFFAOYSA-N sulfanylideneplatinum Chemical compound [Pt]=S JOKPITBUODAHEN-UHFFFAOYSA-N 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
239000012876 carrier material Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
-1 hangane Chemical compound 0.000 description 4
239000000203 mixture Substances 0.000 description 4
230000009467 reduction Effects 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001448 anilines Chemical class 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
229910000510 noble metal Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
150000004982 aromatic amines Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
239000000975 dye Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
230000000737 periodic effect Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
150000004986 phenylenediamines Chemical class 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZRMMVODKVLXCBB-UHFFFAOYSA-N 1-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1=CC=CC=C1 ZRMMVODKVLXCBB-UHFFFAOYSA-N 0.000 description 1
FFDVTEHMPLVFMS-UHFFFAOYSA-N 2,3,5-trimethylaniline Chemical compound CC1=CC(C)=C(C)C(N)=C1 FFDVTEHMPLVFMS-UHFFFAOYSA-N 0.000 description 1
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 1
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
WKURVXXDGMYSDP-UHFFFAOYSA-N 2-propyl-aniline Chemical compound CCCC1=CC=CC=C1N WKURVXXDGMYSDP-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
OZXAIGIRPOOJTI-VLGMZSPHSA-N 7-hdohe Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C=C\C(O)C\C=C/CCC(O)=O OZXAIGIRPOOJTI-VLGMZSPHSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
NEFJYNHYLVYVKW-UHFFFAOYSA-N C1(=CC=CC=C1)NC1=CC=CC=C1.NN Chemical compound C1(=CC=CC=C1)NC1=CC=CC=C1.NN NEFJYNHYLVYVKW-UHFFFAOYSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
102000006835 Lamins Human genes 0.000 description 1
108010047294 Lamins Proteins 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000669298 Pseudaulacaspis pentagona Species 0.000 description 1
241000589614 Pseudomonas stutzeri Species 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000006471 dimerization reaction Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000000852 hydrogen donor Substances 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical class CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
210000005053 lamin Anatomy 0.000 description 1
238000002386 leaching Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052976 metal sulfide Inorganic materials 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
150000002832 nitroso derivatives Chemical class 0.000 description 1
125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003142 primary aromatic amines Chemical class 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
230000007306 turnover Effects 0.000 description 1
239000008096 xylene Substances 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
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups

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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)

DD79211479A 1978-03-11 1979-03-08 Verfahren zur herstellung von p-amino-diphenylamin DD142331A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2810666A DE2810666B2 (de)	1978-03-11	1978-03-11	Verfahren zur Herstellung von p-Amino-diphenylamin

Publications (1)

Publication Number	Publication Date
DD142331A5 true DD142331A5 (de)	1980-06-18

Family

ID=6034193

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79211479A DD142331A5 (de)	1978-03-11	1979-03-08	Verfahren zur herstellung von p-amino-diphenylamin

Country Status (19)

Country	Link
JP (1)	JPS54128530A (fr)
AT (1)	AT367017B (fr)
BE (1)	BE874713A (fr)
BR (1)	BR7901401A (fr)
CA (1)	CA1127666A (fr)
CH (1)	CH639937A5 (fr)
CS (1)	CS203035B2 (fr)
DD (1)	DD142331A5 (fr)
DE (1)	DE2810666B2 (fr)
ES (1)	ES478478A1 (fr)
FR (1)	FR2419276A1 (fr)
GB (1)	GB2015998B (fr)
HU (1)	HU180419B (fr)
IT (1)	IT1114098B (fr)
NL (1)	NL7901809A (fr)
PL (1)	PL113863B1 (fr)
RO (1)	RO76866A (fr)
SU (1)	SU828961A3 (fr)
ZA (1)	ZA791041B (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8486223B2 (en)	2003-07-04	2013-07-16	Jiangsu Sinorgchem Technology Co., Ltd.	Falling film evaporator
US7176333B2 (en)	2003-07-04	2007-02-13	Sinorgchem Company, Shandong	Process for preparing 4-aminodiphenylamine
US8686188B2 (en)	2003-07-04	2014-04-01	Jiangsu Sinorgchem Technology Co., Ltd.	Process for preparing 4-aminodiphenylamine
CA2515238C (fr)	2003-07-04	2011-06-28	Nongyue Wang	Procede de preparation de 4-aminodiphenylamine
CN102259029B (zh)	2010-05-24	2014-12-10	江苏圣奥化学科技有限公司	固体碱催化剂
CN119661372B (zh) *	2023-09-19	2026-01-06	中国石油化工股份有限公司	一种苯胺合成二苯胺的方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1296211A (fr) *	1969-01-27	1972-11-15
DE2355737C2 (de) *	1973-11-08	1982-10-21	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von 4-Amino-diphenylamin

1978
- 1978-03-11 DE DE2810666A patent/DE2810666B2/de not_active Withdrawn
1979
- 1979-03-06 ZA ZA791041A patent/ZA791041B/xx unknown
- 1979-03-06 CS CS791503A patent/CS203035B2/cs unknown
- 1979-03-07 CH CH221879A patent/CH639937A5/de not_active IP Right Cessation
- 1979-03-07 NL NL7901809A patent/NL7901809A/xx not_active Application Discontinuation
- 1979-03-08 BR BR7901401A patent/BR7901401A/pt unknown
- 1979-03-08 CA CA323,034A patent/CA1127666A/fr not_active Expired
- 1979-03-08 DD DD79211479A patent/DD142331A5/de unknown
- 1979-03-09 IT IT48277/79A patent/IT1114098B/it active
- 1979-03-09 RO RO7996829A patent/RO76866A/fr unknown
- 1979-03-09 GB GB7908332A patent/GB2015998B/en not_active Expired
- 1979-03-09 AT AT0180079A patent/AT367017B/de not_active IP Right Cessation
- 1979-03-09 BE BE0/193920A patent/BE874713A/fr not_active IP Right Cessation
- 1979-03-09 SU SU792738051A patent/SU828961A3/ru active
- 1979-03-09 JP JP2680779A patent/JPS54128530A/ja active Pending
- 1979-03-09 ES ES478478A patent/ES478478A1/es not_active Expired
- 1979-03-09 FR FR7906137A patent/FR2419276A1/fr active Pending
- 1979-03-09 HU HU79AO475A patent/HU180419B/hu unknown
- 1979-03-10 PL PL1979214043A patent/PL113863B1/pl unknown

Also Published As

Publication number	Publication date
ZA791041B (en)	1980-03-26
NL7901809A (nl)	1979-09-13
DE2810666B2 (de)	1981-01-29
CH639937A5 (de)	1983-12-15
HU180419B (en)	1983-03-28
AT367017B (de)	1982-05-25
GB2015998A (en)	1979-09-19
ATA180079A (de)	1981-10-15
SU828961A3 (ru)	1981-05-07
PL113863B1 (en)	1981-01-31
FR2419276A1 (fr)	1979-10-05
RO76866A (fr)	1982-03-24
CA1127666A (fr)	1982-07-13
JPS54128530A (en)	1979-10-05
GB2015998B (en)	1982-07-14
DE2810666A1 (de)	1979-09-27
IT7948277A0 (it)	1979-03-09
IT1114098B (it)	1986-01-27
PL214043A1 (fr)	1979-11-05
BR7901401A (pt)	1979-10-09
BE874713A (fr)	1979-07-02
CS203035B2 (en)	1981-02-27
ES478478A1 (es)	1979-06-01

Publication	Publication Date	Title
EP0053696A1 (fr)	1982-06-16	Procédé pour la préparation d'amines cycloaliphatiques et/ou aromatiques
DE19600722A1 (de)	1997-07-17	Verfahren zur Herstellung von gegebenenfalls substituierten 4-Aminodiphenylaminen
DE2362780A1 (de)	1975-06-19	Verfahren zur herstellung ungesaettigter aminoverbindungen
DE2503187C3 (de)	1979-05-31	Verfahren zur Herstellung durch Chlor meta-substituierte Aniline
DE2713373B2 (de)	1979-04-12	Verfahren zur Entpyrophorisierung von pyrophoren Raney-Katalysatoren
EP0415158B1 (fr)	1993-12-29	Procédé pour la préparation d'amines aromatiques substituées par du chlore
DE3443385C2 (fr)	1987-05-27
EP0057871B1 (fr)	1984-10-03	Procédé de préparation de 2,6-diaminotoluène, le cas échéant p-chlorosubstitué
CH639937A5 (de)	1983-12-15	Verfahren zur herstellung von p-amino-diphenylamin.
DE2357370A1 (de)	1974-05-22	Verfahren zur herstellung aromatischer hydroxylamine in gegenwart von katalysatoren
DE2355737C2 (de)	1982-10-21	Verfahren zur Herstellung von 4-Amino-diphenylamin
EP0479877B1 (fr)	1994-10-12	Procede de production de n-alkylanilines halogenes
DE2456308A1 (de)	1976-08-12	Verfahren zur herstellung von aminoverbindungen
DE2455238A1 (de)	1975-05-22	Verfahren zur herstellung aromatischer hydroxylamine durch hydrierung aromatischer nitroderivate
DE4210311C2 (fr)	1994-01-20
EP0470375B1 (fr)	1994-03-23	Procédé pour la préparation d'amines aromatiques substitués dans la position p par C1-4 alkoxy
DE2715785A1 (de)	1977-10-20	Verfahren zur herstellung von hydroxylamino- und aminoverbindungen
DE2819826A1 (de)	1979-11-08	Verfahren zur herstellung von urethanen
DE19804556B4 (de)	2005-04-07	Verbessertes Verfahren zur Herstellung von p-Aminophenolen
CH622240A5 (en)	1981-03-31	Process for the preparation of 1,5- and/or 1,8-diaminonaphthalene
DE881658C (de)	1953-07-02	Verfahren zur Herstellung von Aminoverbindungen
DE69328046T2 (de)	2000-10-05	Verfahren zur Herstellung von Diphenylamin oder kernsubstituierten Derivaten
DE19754571A1 (de)	1999-06-10	Verfahren zur Herstellung von variablen Gemischen aus Cyclohexylamin und Dicyclohexylamin
EP0481316A1 (fr)	1992-04-22	Procédé pour la préparation du 2,2-bis(aminophényl)-propane
DE2452015A1 (de)	1976-05-06	Verfahren zur herstellung von diaminonaphthalin