NO136537B - - Google Patents
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- Publication number
- NO136537B NO136537B NO319672A NO319672A NO136537B NO 136537 B NO136537 B NO 136537B NO 319672 A NO319672 A NO 319672A NO 319672 A NO319672 A NO 319672A NO 136537 B NO136537 B NO 136537B
- Authority
- NO
- Norway
- Prior art keywords
- aniline
- reaction
- mol
- ketone
- sieves
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 150000002466 imines Chemical class 0.000 claims description 13
- 239000002808 molecular sieve Substances 0.000 claims description 13
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 6
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000008365 aromatic ketones Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 56
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- YEYCASGOSICVMZ-UHFFFAOYSA-N n-phenylpropan-2-imine Chemical compound CC(C)=NC1=CC=CC=C1 YEYCASGOSICVMZ-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic ketones Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- RTAMRKGXSTZINR-UHFFFAOYSA-N 2-methyl-n-phenylpropan-1-imine Chemical compound CC(C)C=NC1=CC=CC=C1 RTAMRKGXSTZINR-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-ethyl-N-phenylamine Natural products CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
- B01J20/16—Alumino-silicates
- B01J20/18—Synthetic zeolitic molecular sieves
Landscapes
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2844571 | 1971-09-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO136537B true NO136537B (enrdf_load_stackoverflow) | 1977-06-13 |
| NO136537C NO136537C (no) | 1977-09-21 |
Family
ID=11223619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO319672A NO136537C (no) | 1971-09-10 | 1972-09-08 | Fremgangsm}te for fremstilling av iminer |
Country Status (14)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2525295C3 (de) * | 1975-06-06 | 1980-02-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Azomethinen |
| US4855500A (en) * | 1988-05-04 | 1989-08-08 | Pfizer Inc. | Process for preparing a ketimine |
| US5292953A (en) * | 1990-08-09 | 1994-03-08 | Bayer Aktiengesellschaft | Process for the preparation of azomethines |
| DE4025185A1 (de) * | 1990-08-09 | 1992-02-13 | Bayer Ag | Verfahren zur herstellung von azomethinen |
-
0
- BE BE788421D patent/BE788421A/xx unknown
-
1972
- 1972-08-22 ES ES406364A patent/ES406364A1/es not_active Expired
- 1972-08-24 GB GB3957372A patent/GB1396762A/en not_active Expired
- 1972-09-05 FR FR7231347A patent/FR2152101A5/fr not_active Expired
- 1972-09-08 DD DD16554972A patent/DD101148A5/xx unknown
- 1972-09-08 NO NO319672A patent/NO136537C/no unknown
- 1972-09-08 LU LU66025D patent/LU66025A1/xx unknown
- 1972-09-08 AT AT773972A patent/AT319201B/de not_active IP Right Cessation
- 1972-09-08 CA CA151,319A patent/CA983958A/en not_active Expired
- 1972-09-08 DE DE19722244238 patent/DE2244238A1/de active Pending
- 1972-09-08 NL NL7212214A patent/NL7212214A/xx unknown
- 1972-09-09 CH CH1321572A patent/CH551384A/fr not_active IP Right Cessation
- 1972-09-11 JP JP9048772A patent/JPS4856631A/ja active Pending
- 1972-09-11 SE SE1170472A patent/SE396380B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA983958A (en) | 1976-02-17 |
| FR2152101A5 (enrdf_load_stackoverflow) | 1973-04-20 |
| JPS4856631A (enrdf_load_stackoverflow) | 1973-08-09 |
| SE396380B (sv) | 1977-09-19 |
| DD101148A5 (enrdf_load_stackoverflow) | 1973-10-20 |
| NO136537C (no) | 1977-09-21 |
| CH551384A (fr) | 1974-07-15 |
| ES406364A1 (es) | 1975-07-01 |
| AT319201B (de) | 1974-12-10 |
| LU66025A1 (enrdf_load_stackoverflow) | 1973-01-17 |
| BE788421A (fr) | 1973-01-02 |
| GB1396762A (en) | 1975-06-04 |
| NL7212214A (enrdf_load_stackoverflow) | 1973-03-13 |
| DE2244238A1 (de) | 1973-03-15 |
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