DE1289530B - Verfahren zur Herstellung von Aminobenzolen - Google Patents
Verfahren zur Herstellung von AminobenzolenInfo
- Publication number
- DE1289530B DE1289530B DEH49974A DEH0049974A DE1289530B DE 1289530 B DE1289530 B DE 1289530B DE H49974 A DEH49974 A DE H49974A DE H0049974 A DEH0049974 A DE H0049974A DE 1289530 B DE1289530 B DE 1289530B
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- phenol
- aminobenzenes
- aniline
- ammonia
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000001448 anilines Chemical class 0.000 title claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 235000012239 silicon dioxide Nutrition 0.000 claims description 5
- 150000005204 hydroxybenzenes Chemical class 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 22
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 15
- 229960003742 phenol Drugs 0.000 description 11
- VXSCPERJHPWROZ-UHFFFAOYSA-N 2,4,5-trimethylphenol Chemical compound CC1=CC(C)=C(O)C=C1C VXSCPERJHPWROZ-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 1
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- HHUIAYDQMNHELC-UHFFFAOYSA-N [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O HHUIAYDQMNHELC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000012808 vapor phase 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
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US216063A US3272865A (en) | 1962-08-10 | 1962-08-10 | Preparation of aminated benzenes from hydroxy benzenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1289530B true DE1289530B (de) | 1969-02-20 |
Family
ID=22805523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH49974A Pending DE1289530B (de) | 1962-08-10 | 1963-08-10 | Verfahren zur Herstellung von Aminobenzolen |
Country Status (9)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0449546A1 (en) * | 1990-03-26 | 1991-10-02 | Indspec Chemical Corporation | Process for the preparation of m-aminophenols from resorcinol |
| WO2012160072A1 (de) | 2011-05-24 | 2012-11-29 | Basf Se | Verfahren zur herstellung von polyisocyanaten aus biomasse |
| US8933262B2 (en) | 2011-05-24 | 2015-01-13 | Basf Se | Process for preparing polyisocyanates from biomass |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3361818A (en) * | 1966-12-07 | 1968-01-02 | Halcon International Inc | Process for preparing aminated benzenes from aminated cyclohexanes |
| US3860650A (en) * | 1969-05-27 | 1975-01-14 | Halcon International Inc | Process for the production of organic amines |
| US3931298A (en) * | 1971-03-11 | 1976-01-06 | Ethyl Corporation | Chemical process for forming 2,6-dimethylaniline |
| US4252742A (en) * | 1979-07-13 | 1981-02-24 | Ciba-Geigy Corporation | Chemical process for the preparation of 2,6-dialkylcyclohexylamines from 2,6-dialkylphenols |
| US4380669A (en) * | 1981-04-08 | 1983-04-19 | Mobil Oil Corporation | Process for synthesizing aniline |
| DE3147734A1 (de) * | 1981-06-27 | 1983-01-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von alkylsubstituierten anilinen |
| US4395554A (en) * | 1981-12-01 | 1983-07-26 | Mobil Oil Corporation | Process for producing alpha-picoline |
| US4388461A (en) * | 1981-12-01 | 1983-06-14 | Mobil Oil Corporation | Process for producing alpha-picoline |
| US4404399A (en) * | 1982-09-30 | 1983-09-13 | The Halcon Sd Group, Inc. | Coproduction of aniline and diphenylamine |
| US4480127A (en) * | 1983-05-20 | 1984-10-30 | The Halcon Sd Group, Inc. | Process for the production of variable amounts of DPA and aniline using only phenol and ammonia as the feedstock |
| CA1244836A (en) * | 1984-03-14 | 1988-11-15 | Teruyuki Nagata | Process for producing diphenylamines or n,n'-diphenyl- phenylenediamines |
| US5545753A (en) * | 1986-11-17 | 1996-08-13 | Mitsui Petrochemical Industries, Ltd. | Process for preparing anilines, catalysts used therefor and process for preparing same |
| JPH0813791B2 (ja) * | 1987-12-18 | 1996-02-14 | 三井石油化学工業株式会社 | アニリン類の製造方法 |
| US4922024A (en) * | 1988-04-14 | 1990-05-01 | The Dow Chemical Company | Amination process employing group vib metal catalysts |
| US5030740A (en) * | 1988-10-14 | 1991-07-09 | The Dow Chemical Company | Process for preparing linearly-extended polyalkylenepolyamines |
| US5091579A (en) * | 1989-07-14 | 1992-02-25 | Aristech Chemical Corporation | Aniline catalyst |
| US5214210A (en) * | 1991-09-05 | 1993-05-25 | Aristech Chemical Corporation | Catalyst and process for making aniline from phenol |
| DE10347438A1 (de) * | 2003-10-13 | 2005-05-04 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| DE102005006692A1 (de) * | 2005-02-15 | 2006-08-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di-und Polyaminen der Diphenylmethanreihe |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE530736C (de) * | 1929-05-25 | 1931-07-31 | Rheinische Kampfer Fabrik G M | Verfahren zur katalytischen Arylierung von Phenolen und aromatischen Aminen |
| DE570365C (de) * | 1930-01-17 | 1933-02-15 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung aromatischer Amine aus Oxyverbindungen der Benzolreihe |
| FR850743A (fr) * | 1938-02-24 | 1939-12-23 | Ig Farbenindustrie Ag | Dérivés de l'aniline substitués dans le noyau et leur procédé de préparation |
| DE1055540B (de) | 1957-12-10 | 1959-04-23 | Bayer Ag | Verfahren zur Herstellung von Diarylaminen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1449423A (en) * | 1922-04-01 | 1923-03-27 | Lowy Alexander | Production of naphthyl amines |
| US1475502A (en) * | 1922-06-16 | 1923-11-27 | Manning Refining Equipment Cor | Method of revivifying finely-divided fuller's earth, bone char, and the like |
| US1935209A (en) * | 1930-01-16 | 1933-11-14 | Ig Farbenindustrie Ag | Production of aromatic amines from phenols |
| US2113241A (en) * | 1931-12-29 | 1938-04-05 | Nat Aniline & Chem Co Inc | Catalytic synthesis of amines |
| US2226635A (en) * | 1937-09-23 | 1940-12-31 | Celanese Corp | Production of lower alkylamines |
| US2389500A (en) * | 1940-09-07 | 1945-11-20 | Sharples Chemicals Inc | Manufacture of amines |
-
0
- NL NL296184D patent/NL296184A/xx unknown
-
1962
- 1962-08-10 US US216063A patent/US3272865A/en not_active Expired - Lifetime
-
1963
- 1963-07-30 GB GB30148/63A patent/GB1046790A/en not_active Expired
- 1963-08-07 BE BE635927A patent/BE635927A/fr unknown
- 1963-08-08 CH CH983463A patent/CH443333A/fr unknown
- 1963-08-08 LU LU44224D patent/LU44224A1/xx unknown
- 1963-08-10 DE DEH49974A patent/DE1289530B/de active Pending
- 1963-08-10 ES ES290763A patent/ES290763A1/es not_active Expired
- 1963-08-12 SE SE08791/63A patent/SE335138B/xx unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE530736C (de) * | 1929-05-25 | 1931-07-31 | Rheinische Kampfer Fabrik G M | Verfahren zur katalytischen Arylierung von Phenolen und aromatischen Aminen |
| DE570365C (de) * | 1930-01-17 | 1933-02-15 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung aromatischer Amine aus Oxyverbindungen der Benzolreihe |
| FR850743A (fr) * | 1938-02-24 | 1939-12-23 | Ig Farbenindustrie Ag | Dérivés de l'aniline substitués dans le noyau et leur procédé de préparation |
| DE1055540B (de) | 1957-12-10 | 1959-04-23 | Bayer Ag | Verfahren zur Herstellung von Diarylaminen |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0449546A1 (en) * | 1990-03-26 | 1991-10-02 | Indspec Chemical Corporation | Process for the preparation of m-aminophenols from resorcinol |
| WO2012160072A1 (de) | 2011-05-24 | 2012-11-29 | Basf Se | Verfahren zur herstellung von polyisocyanaten aus biomasse |
| US8933262B2 (en) | 2011-05-24 | 2015-01-13 | Basf Se | Process for preparing polyisocyanates from biomass |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1046790A (en) | 1966-10-26 |
| BE635927A (fr) | 1964-02-07 |
| ES290763A1 (es) | 1963-10-16 |
| NL296184A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1900-01-01 |
| US3272865A (en) | 1966-09-13 |
| SE335138B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-05-17 |
| LU44224A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-02-08 |
| DE1667104B2 (de) | 1975-12-04 |
| CH443333A (fr) | 1967-09-15 |
| DE1667104A1 (de) | 1971-06-09 |
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