GB1587962A - Manufacture of n-alkylanilines and their nuclear substituted homologs - Google Patents
Manufacture of n-alkylanilines and their nuclear substituted homologs Download PDFInfo
- Publication number
- GB1587962A GB1587962A GB42621/77A GB4262177A GB1587962A GB 1587962 A GB1587962 A GB 1587962A GB 42621/77 A GB42621/77 A GB 42621/77A GB 4262177 A GB4262177 A GB 4262177A GB 1587962 A GB1587962 A GB 1587962A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carried out
- pressure
- reaction
- homolog
- catalyst
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- 239000010941 cobalt Substances 0.000 claims description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 239000011572 manganese Substances 0.000 claims description 3
- 150000003333 secondary alcohols Chemical class 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 125000000075 primary alcohol group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 150000003138 primary alcohols Chemical class 0.000 claims 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- YQYUUNRAPYPAPC-UHFFFAOYSA-N n,n-diethyl-2-methylaniline Chemical compound CCN(CC)C1=CC=CC=C1C YQYUUNRAPYPAPC-UHFFFAOYSA-N 0.000 description 4
- MWOUGPLLVVEUMM-UHFFFAOYSA-N n-ethyl-2-methylaniline Chemical compound CCNC1=CC=CC=C1C MWOUGPLLVVEUMM-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 238000007126 N-alkylation reaction Methods 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001448 anilines Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- FEUISMYEFPANSS-UHFFFAOYSA-N 2-methylcyclohexan-1-amine Chemical compound CC1CCCCC1N FEUISMYEFPANSS-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GGARKJIWYNVMBF-UHFFFAOYSA-N n-(2-methylpropyl)aniline Chemical compound CC(C)CNC1=CC=CC=C1 GGARKJIWYNVMBF-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002459 sustained effect 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
- C07C209/04—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2646379A DE2646379C3 (de) | 1976-10-14 | 1976-10-14 | Verfahren zur Herstellung von N-Alkylanilinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1587962A true GB1587962A (en) | 1981-04-15 |
Family
ID=5990441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB42621/77A Expired GB1587962A (en) | 1976-10-14 | 1977-10-13 | Manufacture of n-alkylanilines and their nuclear substituted homologs |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4196147A (https=) |
| BE (1) | BE859689A (https=) |
| DE (1) | DE2646379C3 (https=) |
| FR (1) | FR2367735A1 (https=) |
| GB (1) | GB1587962A (https=) |
| NL (1) | NL7711156A (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH633520A5 (de) * | 1978-06-30 | 1982-12-15 | Lonza Ag | Verfahren zur herstellung von n-alkylarylaminen. |
| EP0031089B1 (de) * | 1979-12-20 | 1984-02-15 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von N,N'-Diarylalkylendiaminen oder N,N',N"-Triaryldialkylen-triaminen |
| US4404399A (en) * | 1982-09-30 | 1983-09-13 | The Halcon Sd Group, Inc. | Coproduction of aniline and diphenylamine |
| DE3309354C2 (de) * | 1983-03-16 | 1994-02-24 | Basf Ag | Verfahren zur Herstellung von 2-substituierten 6-Methylanilinen |
| CN100408179C (zh) * | 2005-05-20 | 2008-08-06 | 中国科学院大连化学物理研究所 | 用于苯胺与醇气相合成n-烷基苯胺的过渡金属催化剂 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE361696A (https=) * | 1929-01-26 | 1929-07-31 | Alais & Froges & Camarque Cie | |
| US2813124A (en) * | 1955-04-18 | 1957-11-12 | Rip G Rice | Preparation of secondary aromatic amines |
| DE1155136B (de) * | 1961-06-08 | 1963-10-03 | Basf Ag | Verfahren zur Herstellung von N, N'-Dialkyl-aryldiaminen |
| FR1324155A (fr) * | 1962-06-04 | 1963-04-12 | Basf Ag | Procédé pour la production d'amines aromatiques alcoylées |
| US3316261A (en) * | 1963-10-28 | 1967-04-25 | Jefferson Chem Co Inc | Process for making a 2-aminoketone |
| BE757840A (fr) * | 1969-10-23 | 1971-04-22 | Basf Ag | Procede de preparation d'amines a partir d'alcools |
| JPS5140060B1 (https=) * | 1969-12-15 | 1976-11-01 | ||
| US4082802A (en) * | 1970-04-28 | 1978-04-04 | Sumitomo Chemical Company, Limited | Process for the preparation of aromatic secondary or tertiary amino compounds |
| US3819709A (en) * | 1970-12-09 | 1974-06-25 | New Japan Chem Co Ltd | Synthesis of n-methylaniline |
-
1976
- 1976-10-14 DE DE2646379A patent/DE2646379C3/de not_active Expired
-
1977
- 1977-09-29 US US05/837,938 patent/US4196147A/en not_active Expired - Lifetime
- 1977-10-11 NL NL7711156A patent/NL7711156A/xx not_active Application Discontinuation
- 1977-10-13 GB GB42621/77A patent/GB1587962A/en not_active Expired
- 1977-10-13 BE BE181711A patent/BE859689A/xx not_active IP Right Cessation
- 1977-10-14 FR FR7731008A patent/FR2367735A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2367735A1 (fr) | 1978-05-12 |
| NL7711156A (nl) | 1978-04-18 |
| BE859689A (fr) | 1978-04-13 |
| FR2367735B1 (https=) | 1980-08-29 |
| DE2646379C3 (de) | 1982-04-08 |
| DE2646379B2 (de) | 1981-06-11 |
| DE2646379A1 (de) | 1978-04-27 |
| US4196147A (en) | 1980-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19931013 |