NO137193B - PROCEDURES FOR THE PREPARATION OF DIFENYLAMINE AND DERIVATIVES THEREOF - Google Patents
PROCEDURES FOR THE PREPARATION OF DIFENYLAMINE AND DERIVATIVES THEREOF Download PDFInfo
- Publication number
- NO137193B NO137193B NO732573A NO257373A NO137193B NO 137193 B NO137193 B NO 137193B NO 732573 A NO732573 A NO 732573A NO 257373 A NO257373 A NO 257373A NO 137193 B NO137193 B NO 137193B
- Authority
- NO
- Norway
- Prior art keywords
- silicon dioxide
- imine
- oxygen
- reaction
- molar ratio
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 18
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 14
- 150000002466 imines Chemical class 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000377 silicon dioxide Substances 0.000 claims description 11
- 235000012239 silicon dioxide Nutrition 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229910001868 water Inorganic materials 0.000 claims description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- RPFGCUFAJAQNLJ-UHFFFAOYSA-N n-phenylcyclohexanimine Chemical compound C1CCCCC1=NC1=CC=CC=C1 RPFGCUFAJAQNLJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003701 inert diluent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- -1 silicon dioxide aluminate Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- VPRIGCVCJPKVFZ-UHFFFAOYSA-N 4-chloro-n-phenylaniline Chemical compound C1=CC(Cl)=CC=C1NC1=CC=CC=C1 VPRIGCVCJPKVFZ-UHFFFAOYSA-N 0.000 description 1
- OBHGSIGHEBGGFS-UHFFFAOYSA-N 4-methoxy-n-phenylaniline Chemical compound C1=CC(OC)=CC=C1NC1=CC=CC=C1 OBHGSIGHEBGGFS-UHFFFAOYSA-N 0.000 description 1
- AGHYMXKKEXDUTA-UHFFFAOYSA-N 4-methyl-n-phenylaniline Chemical compound C1=CC(C)=CC=C1NC1=CC=CC=C1 AGHYMXKKEXDUTA-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UPVOINJYKFQHCI-UHFFFAOYSA-N n-(4-chlorophenyl)cyclohexanimine Chemical compound C1=CC(Cl)=CC=C1N=C1CCCCC1 UPVOINJYKFQHCI-UHFFFAOYSA-N 0.000 description 1
- ONWDRYHADDRYDR-UHFFFAOYSA-N n-(4-methoxyphenyl)cyclohexanimine Chemical compound C1=CC(OC)=CC=C1N=C1CCCCC1 ONWDRYHADDRYDR-UHFFFAOYSA-N 0.000 description 1
- CYKKBANDRNLJHN-UHFFFAOYSA-N n-(4-methylphenyl)cyclohexanimine Chemical compound C1=CC(C)=CC=C1N=C1CCCCC1 CYKKBANDRNLJHN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 230000007306 turnover Effects 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
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)
Description
Foreliggende oppfinnelse angår en fremgangsmåte for fremstilling The present invention relates to a method for production
av difenylamin og derivater derav, hvor et imin med den generelle formel of diphenylamine and derivatives thereof, where an imine of the general formula
hvori R er en substituent valgt fra alkyl, hydrogen, fenyl, amin, wherein R is a substituent selected from alkyl, hydrogen, phenyl, amine,
alkoksy, hydroksy eller halogen omsettes med oksygen eller en oksygenholdig gass ved temperatur fra 300° til 450°C, og det særegne ved fremgangsmåten i henhold til oppfinnelsen er at omsetningen utfores ved et molart forhold mellom oksygen og imin fra 0,2:1 til 20:1, fortrinnsvis fra 0,8:1 til 10:1, idet omsetningen utfores i nærvær av et inert foftynningsmiddel valgt fra nitrogen, argon, karbondioksyd, vanndamp, benzen eller mettede hydrokarboner som er bestandige ved reaksjonsbetingélsene, Alkoxy, hydroxy or halogen is reacted with oxygen or an oxygen-containing gas at a temperature from 300° to 450°C, and the peculiarity of the method according to the invention is that the reaction is carried out at a molar ratio between oxygen and imine of from 0.2:1 to 20:1, preferably from 0.8:1 to 10:1, the reaction being carried out in the presence of an inert diluent selected from nitrogen, argon, carbon dioxide, water vapour, benzene or saturated hydrocarbons which are stable under the reaction conditions,
og i nærvær av kontaktmasser valgt fra silisiumdioksyd, aluminium- and in the presence of contact masses selected from silicon dioxide, aluminum-
oksyd, silisiumdioksyd-aluminiumoksyd, silisiumdioksydaluminat og oksyder eller oksydblandinger eller forbindelser av metaller tilhorende gruppene fra og med gruppe III til og med gruppe VIII oxide, silicon dioxide-alumina, silicon dioxide aluminate and oxides or oxide mixtures or compounds of metals belonging to the groups from and including group III to and including group VIII
i det periodiske system. in the periodic table.
Slike iminer kan lett syntetiseres i henhold til fremgangsmåter Such imines can be easily synthesized according to methods
beskrevet i litteraturen, f.eks. ved å gå ut fra aromatiske aminer (spesielt anilin og derivater derav inneholdende substituenter i benzenringen) og cykloheksanon. described in the literature, e.g. starting from aromatic amines (especially aniline and derivatives thereof containing substituents in the benzene ring) and cyclohexanone.
Ved fremgangsmåten i henhold til oppfinnelsen er det således mulig å oppnå difenylamin og substituerte derivater derav ved i dampfase å omsette N-cykloheksylidenanilin og derivater derav med molekylært oksygen eller oksygenholdig gass, fortrinnsvis luft. With the method according to the invention, it is thus possible to obtain diphenylamine and substituted derivatives thereof by reacting in the vapor phase N-cyclohexylidenaniline and derivatives thereof with molecular oxygen or an oxygen-containing gas, preferably air.
Omsetningen utfores ved hoye temperaturer og i nærvær av inerte fortynningsmidler som nitrogen, argon, karbondioksyd, vanndamp, benzen og mettede hydrokarboner som er bestandige ved reaksjonsbetingelsene. The reaction is carried out at high temperatures and in the presence of inert diluents such as nitrogen, argon, carbon dioxide, water vapour, benzene and saturated hydrocarbons which are stable under the reaction conditions.
Molforholdet mellom oksygen og imin i tilforselen avhenger av iminstrukturen. Under enhver omstendighet varierer det fra 0,2:1 til 20:1 og fortrinnsvis fra 0,8:1 til 10:1. The molar ratio between oxygen and imine in the feed depends on the imine structure. In any case it ranges from 0.2:1 to 20:1 and preferably from 0.8:1 to 10:1.
Omsetningen utfores i nærvær av egnede katalysatorer og som eksempler på anvendbare katalysatorer eller kontaktmasser nevnes slike som vanligvis anvendes som oksydasjonskatalysatorer, f.eks. silisiumdioksyd, aluminiumoksyd, silisiumdioksyd-aluminiumoksyd, silisiumdioksyd-aluminater samt oksyder eller oksydblandinger eller forbindelser av metaller tilhorende gruppene III til og med VIII i det periodiske system. The reaction is carried out in the presence of suitable catalysts and as examples of usable catalysts or contact masses those which are usually used as oxidation catalysts are mentioned, e.g. silicon dioxide, aluminum oxide, silicon dioxide-alumina, silicon dioxide-aluminates as well as oxides or oxide mixtures or compounds of metals belonging to groups III to VIII inclusive of the periodic table.
En spesiell måte å.utfore fremgangsmåten i henhold til oppfinnelsen på består i å omsette et imin med molekylært oksygen, eller oksygenholdig gass i dampfase ved temperatur varierende fra 300° til 450°C på et kontaktmateriale, hovedsakelig bestående av aktivt silisiumdioksyd. A special way of carrying out the method according to the invention consists in reacting an imine with molecular oxygen, or oxygen-containing gas in vapor phase at a temperature varying from 300° to 450°C on a contact material, mainly consisting of active silicon dioxide.
Omsetningen kan utfores i hvilken som helst reaktortype, d.v.s. med fast, beveget eller fluidisert skikt. The turnover can be carried out in any type of reactor, i.e. with fixed, moving or fluidized bed.
Det anvendes som nevnt en temperatur varierende fra 400° til 450°C og trykket kan variere fra noen få mm Hg opp til: 10 atmosfærers trykk, men det foretrekkes å arbeide ved atmosfæretrykk. As mentioned, a temperature varying from 400° to 450°C is used and the pressure can vary from a few mm Hg up to: 10 atmospheres pressure, but it is preferred to work at atmospheric pressure.
Kontakttiden mellom reagensene og katalysatoren velges mellom 0,1 og 20 sekunder, spesielt mellom 0,5 og 10 sekunder. Med kontakttid menes forholdet mellom reaktorvolumet hvori omsetningen finner sted og stromningen av reagensene i gassformig tilstand ved reaksjonsbetingelsene. The contact time between the reagents and the catalyst is chosen between 0.1 and 20 seconds, in particular between 0.5 and 10 seconds. By contact time is meant the ratio between the reactor volume in which the reaction takes place and the flow of the reagents in a gaseous state at the reaction conditions.
Oppfinnelsen vil lettere kunne forståes ut fra de folgende eksempler som er ment å illustrere noen av de mulige anvendelser av fremgangsmåten i henhold til oppfinnelsen for fremstilling av difenylamin og derivater derav og som kan ha industriell interesse. The invention will be easier to understand from the following examples which are intended to illustrate some of the possible applications of the method according to the invention for the production of diphenylamine and derivatives thereof and which may have industrial interest.
I eksemplene skal utrykkene omdannelse, selektivitet og utbytte forståes som folger: In the examples, the expressions conversion, selectivity and yield are to be understood as follows:
Eksempel 1 Example 1
I en reaktor med ca. 38 mm innvendig diameter ble innfort 600 cm<3 >katalysator bestående av silisiumdioksyd oppnådd ved å gå ut fra en kolloidal silisiumdioksydgel med 30% Si02 stabilisert med NH^In a reactor with approx. 38 mm internal diameter was inserted 600 cm<3 >catalyst consisting of silicon dioxide obtained by starting from a colloidal silicon dioxide gel with 30% SiO2 stabilized with NH^
("Silica Ludox AS") som ved forstovning og ekstrudering ble formet til tabletter med 4 mm diameter og derefter kalsinert ved 500°C. ("Silica Ludox AS") which, by atomization and extrusion, was formed into tablets with a diameter of 4 mm and then calcined at 500°C.
I reaktoren ble innfort N-cykloheksylidenanilin, luft og vann i et molforhold 1:30:60 ved 420°C og en kontakttid på 5 sekunder: Det ble oppnådd en omdannelse av imin på 38% ved en selektivitet til difenylamin på 65%. N-cyclohexylideneaniline, air and water were introduced into the reactor in a molar ratio of 1:30:60 at 420°C and a contact time of 5 seconds: A conversion of imine of 38% was achieved with a selectivity to diphenylamine of 65%.
Eksempel 2 Example 2
600 cm katalysator bestående av platina (0,7%) på silisiumdioksyd ble innfort i samme reaktor som i eksempel 1. N-cykloheksylidenanilin, luft og vann i et molforhold 1:7:20 ble innfort i reaktoren ved 450°C og en kontakttid på 2 sekunder. Det 600 cm of catalyst consisting of platinum (0.7%) on silicon dioxide was introduced into the same reactor as in example 1. N-cyclohexylidenaniline, air and water in a molar ratio of 1:7:20 were introduced into the reactor at 450°C and a contact time in 2 seconds. The
ble oppnådd en iminomdannelse på 43% og en sélektivitet til difenylamin på 50%. an imine conversion of 43% and a selectivity to diphenylamine of 50% was achieved.
Eksempel 3 Example 3
600 cm 3 katalysator bestående av celitt ble innfort i samme reaktor som i eks. 1. N-cykloheksyliden-para-toluidin, luft og vann i et molforhold på 1:10:50 ble innfort i reaktoren ved 430°C med en kontakttid på 2,5 sekunder. 600 cm 3 of catalyst consisting of celite was introduced into the same reactor as in ex. 1. N-cyclohexylidene-para-toluidine, air and water in a molar ratio of 1:10:50 were introduced into the reactor at 430°C with a contact time of 2.5 seconds.
Det ble oppnådd en omdannelse på 43% med en selektivitet til 4-metyldifenylamin på 61%. A conversion of 43% was achieved with a selectivity to 4-methyldiphenylamine of 61%.
Eksempel 4 Example 4
Det ble gjort bruk av den samme katalysator og reaktor som i The same catalyst and reactor were used as in
eks. 3. Det ble i reaktoren innfort N-cykloheksyliden-para-kloranilin, luft og vann i et molforhold på 1:10:50 ved 410°C e.g. 3. N-cyclohexylidene-para-chloroaniline, air and water in a molar ratio of 1:10:50 at 410°C were introduced into the reactor
og 5 sekunder som kontakttid. and 5 seconds as contact time.
Det ble oppnådd 4-klordifenylamin ved 63% selektivitet og en iminomdannelse på 29%. 4-chlorodiphenylamine was obtained at 63% selectivity and an imine conversion of 29%.
Eksempel 5 Example 5
N-cykloheksyliden-para-metoksyanilin, luft og vann ble innfort N-cyclohexylidene-para-methoxyaniline, air and water were introduced
i samme reaktor og under anvendelse av samme katalysator som i eks. 3 i et molforhold på 1:8:30 ved 420°C og 3 sekunders kontakttid. in the same reactor and using the same catalyst as in ex. 3 in a molar ratio of 1:8:30 at 420°C and 3 seconds contact time.
Det ble oppnådd 4-metoksydifenylamin ved 58% selektivitet og en iminomdannelse på 35%. 4-Methoxydiphenylamine was obtained at 58% selectivity and an imine conversion of 35%.
Eksempel 6 Example 6
Det ble gjort bruk av samme reaktor som ble tilfort 600 cm 3 av en katalysator med sammensetning 0,6V20,-.lBi^C^ «1,6M0O3 på 15 % silisiumdioksyd som katalysatorbærer. Det ble i reaktoren innfort The same reactor was used, which was supplied with 600 cm 3 of a catalyst with the composition 0.6V20,-.1Bi^C^ -1.6M0O3 on 15% silicon dioxide as catalyst carrier. It was installed in the reactor
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT26169/72A IT961239B (en) | 1972-06-24 | 1972-06-24 | PROCESS FOR THE PRODUCTION OF DIPHENYLAMINE AND ITS DERIVATIVES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO137193B true NO137193B (en) | 1977-10-10 |
| NO137193C NO137193C (en) | 1978-01-18 |
Family
ID=11218819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO732573A NO137193C (en) | 1972-06-24 | 1973-06-21 | PROCEDURES FOR THE PREPARATION OF DIFENYLAMINE AND DERIVATIVES THEREOF |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS4949924A (en) |
| AR (1) | AR197133A1 (en) |
| AT (1) | AT323716B (en) |
| AU (1) | AU477211B2 (en) |
| BE (1) | BE801095A (en) |
| BG (1) | BG25983A3 (en) |
| BR (1) | BR7304613D0 (en) |
| CA (1) | CA998692A (en) |
| CH (1) | CH574901A5 (en) |
| DD (1) | DD104507A5 (en) |
| DE (1) | DE2331960A1 (en) |
| EG (2) | EG11382A (en) |
| ES (1) | ES416625A1 (en) |
| FR (1) | FR2189376B1 (en) |
| GB (1) | GB1426929A (en) |
| IE (1) | IE38690B1 (en) |
| IT (1) | IT961239B (en) |
| LU (1) | LU67837A1 (en) |
| NL (1) | NL152542B (en) |
| NO (1) | NO137193C (en) |
| PH (1) | PH9588A (en) |
| PL (1) | PL81085B1 (en) |
| RO (1) | RO62808A (en) |
| SE (1) | SE396595B (en) |
| TR (1) | TR17184A (en) |
| ZA (1) | ZA733780B (en) |
| ZM (1) | ZM9973A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1244836A (en) * | 1984-03-14 | 1988-11-15 | Teruyuki Nagata | Process for producing diphenylamines or n,n'-diphenyl- phenylenediamines |
| JPS60193949A (en) * | 1984-03-14 | 1985-10-02 | Mitsui Toatsu Chem Inc | Production of diphenylamine or its nucleus-substituted derivative |
| DE4100514A1 (en) * | 1991-01-10 | 1992-07-16 | Bayer Ag | Di:phenylamine and derivs. prodn. from corresp. N=cyclohexylidene aniline |
| US5382690A (en) * | 1992-08-11 | 1995-01-17 | Mitsui Toatsu Chemicals, Incorporated | Method for preparing aromatic secondary amino compound |
| US5536878A (en) * | 1992-08-11 | 1996-07-16 | Mitsui Toatsu Chemicals, Inc. | Method for preparing aromatic secondary amino compound |
| CN1054368C (en) * | 1992-10-28 | 2000-07-12 | 三井化学株式会社 | Process for the preparation of diphenylamine or nucleus-substituted derivative thereof |
-
1972
- 1972-06-24 IT IT26169/72A patent/IT961239B/en active
-
1973
- 1973-04-04 AR AR247398A patent/AR197133A1/en active
- 1973-05-16 AU AU55762/73A patent/AU477211B2/en not_active Expired
- 1973-05-22 TR TR17184A patent/TR17184A/en unknown
- 1973-05-27 EG EG196/73A patent/EG11382A/en active
- 1973-05-29 EG EG202/73A patent/EG11504A/en active
- 1973-06-05 BG BG023797A patent/BG25983A3/en unknown
- 1973-06-05 ZA ZA733780A patent/ZA733780B/en unknown
- 1973-06-06 IE IE912/73A patent/IE38690B1/en unknown
- 1973-06-11 RO RO7300075103A patent/RO62808A/en unknown
- 1973-06-12 GB GB2797273A patent/GB1426929A/en not_active Expired
- 1973-06-15 PH PH14728*UA patent/PH9588A/en unknown
- 1973-06-18 FR FR7322028A patent/FR2189376B1/fr not_active Expired
- 1973-06-19 BE BE1005173A patent/BE801095A/en unknown
- 1973-06-20 BR BR4613/73A patent/BR7304613D0/en unknown
- 1973-06-20 LU LU67837A patent/LU67837A1/xx unknown
- 1973-06-21 CH CH900273A patent/CH574901A5/xx not_active IP Right Cessation
- 1973-06-21 CA CA174,597A patent/CA998692A/en not_active Expired
- 1973-06-21 NO NO732573A patent/NO137193C/en unknown
- 1973-06-21 SE SE7308846A patent/SE396595B/en unknown
- 1973-06-22 JP JP48069953A patent/JPS4949924A/ja active Pending
- 1973-06-22 AT AT552673A patent/AT323716B/en not_active IP Right Cessation
- 1973-06-22 DE DE2331960A patent/DE2331960A1/en active Pending
- 1973-06-22 DD DD171771A patent/DD104507A5/xx unknown
- 1973-06-23 ES ES416625A patent/ES416625A1/en not_active Expired
- 1973-06-25 NL NL737308823A patent/NL152542B/en unknown
- 1973-06-26 PL PL1973163513A patent/PL81085B1/pl unknown
- 1973-07-01 ZM ZM99/73*7A patent/ZM9973A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG25983A3 (en) | 1979-01-12 |
| NL152542B (en) | 1977-03-15 |
| RO62808A (en) | 1977-10-15 |
| LU67837A1 (en) | 1973-08-28 |
| IT961239B (en) | 1973-12-10 |
| AU477211B2 (en) | 1976-10-21 |
| AR197133A1 (en) | 1974-03-15 |
| PH9588A (en) | 1976-01-19 |
| DE2331960A1 (en) | 1974-01-10 |
| FR2189376B1 (en) | 1976-06-11 |
| PL81085B1 (en) | 1975-08-30 |
| IE38690B1 (en) | 1978-05-10 |
| NL7308823A (en) | 1973-12-28 |
| ZM9973A1 (en) | 1974-05-21 |
| JPS4949924A (en) | 1974-05-15 |
| AU5576273A (en) | 1974-11-21 |
| BR7304613D0 (en) | 1974-08-29 |
| SE396595B (en) | 1977-09-26 |
| IE38690L (en) | 1973-12-24 |
| ES416625A1 (en) | 1976-02-01 |
| GB1426929A (en) | 1976-03-03 |
| EG11382A (en) | 1977-12-31 |
| ZA733780B (en) | 1974-05-29 |
| CA998692A (en) | 1976-10-19 |
| BE801095A (en) | 1973-10-15 |
| CH574901A5 (en) | 1976-04-30 |
| EG11504A (en) | 1977-08-15 |
| NO137193C (en) | 1978-01-18 |
| AT323716B (en) | 1975-07-25 |
| FR2189376A1 (en) | 1974-01-25 |
| TR17184A (en) | 1974-04-25 |
| DD104507A5 (en) | 1974-03-12 |
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