DE2244169A1 - Verfahren zur herstellung von iminen - Google Patents
Verfahren zur herstellung von iminenInfo
- Publication number
- DE2244169A1 DE2244169A1 DE19722244169 DE2244169A DE2244169A1 DE 2244169 A1 DE2244169 A1 DE 2244169A1 DE 19722244169 DE19722244169 DE 19722244169 DE 2244169 A DE2244169 A DE 2244169A DE 2244169 A1 DE2244169 A1 DE 2244169A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- molecular sieves
- ketone
- amine
- carried out
- 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 19
- 150000002466 imines Chemical class 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000002808 molecular sieve Substances 0.000 claims description 18
- 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 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 12
- 150000002576 ketones Chemical class 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical group CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000008365 aromatic ketones Chemical class 0.000 claims description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000008929 regeneration Effects 0.000 description 7
- 238000011069 regeneration method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- -1 nitrogen-containing heterocyclic compounds Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 206010035148 Plague Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000002317 scanning near-field acoustic microscopy Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2844471 | 1971-09-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2244169A1 true DE2244169A1 (de) | 1973-03-22 |
Family
ID=11223617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722244169 Pending DE2244169A1 (de) | 1971-09-10 | 1972-09-08 | Verfahren zur herstellung von iminen |
Country Status (14)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0470460A1 (de) * | 1990-08-09 | 1992-02-12 | Bayer Ag | Verfahren zur Herstellung von Azomethinen |
| US5292953A (en) * | 1990-08-09 | 1994-03-08 | Bayer Aktiengesellschaft | Process for the preparation of azomethines |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2901863A1 (de) * | 1979-01-18 | 1980-07-31 | Bayer Ag | Verfahren zur herstellung von schiff'schen basen durch umsetzung von aromatischen aminen mit ketonen |
| JPS61200953A (ja) * | 1985-03-04 | 1986-09-05 | Agency Of Ind Science & Technol | イミン類及びその製造方法 |
| US4855500A (en) * | 1988-05-04 | 1989-08-08 | Pfizer Inc. | Process for preparing a ketimine |
| JP5057672B2 (ja) * | 2006-02-24 | 2012-10-24 | コニシ株式会社 | イミン系化合物又はオキサゾリジン系化合物の製造方法 |
| JP2020189809A (ja) * | 2019-05-23 | 2020-11-26 | 旭化成株式会社 | イミンの製造方法 |
-
0
- BE BE788420D patent/BE788420A/xx unknown
-
1972
- 1972-08-18 ES ES406354A patent/ES406354A1/es not_active Expired
- 1972-08-24 GB GB3957472A patent/GB1357256A/en not_active Expired
- 1972-09-05 FR FR7231346A patent/FR2152100A5/fr not_active Expired
- 1972-09-07 NL NL7212197A patent/NL7212197A/xx unknown
- 1972-09-08 CA CA151,318A patent/CA983957A/en not_active Expired
- 1972-09-08 DE DE19722244169 patent/DE2244169A1/de active Pending
- 1972-09-08 LU LU66026D patent/LU66026A1/xx unknown
- 1972-09-08 DD DD16555272A patent/DD100712A5/xx unknown
- 1972-09-08 HU HUSA002400 patent/HU167519B/hu unknown
- 1972-09-08 PL PL15765672A patent/PL85136B1/pl unknown
- 1972-09-09 CH CH1321472A patent/CH551383A/fr not_active IP Right Cessation
- 1972-09-11 JP JP47090486A patent/JPS4834837A/ja active Pending
- 1972-09-11 CS CS622572A patent/CS188881B2/cs unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0470460A1 (de) * | 1990-08-09 | 1992-02-12 | Bayer Ag | Verfahren zur Herstellung von Azomethinen |
| US5292953A (en) * | 1990-08-09 | 1994-03-08 | Bayer Aktiengesellschaft | Process for the preparation of azomethines |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2152100A5 (enrdf_load_stackoverflow) | 1973-04-20 |
| DD100712A5 (enrdf_load_stackoverflow) | 1973-10-05 |
| CS188881B2 (en) | 1979-03-30 |
| LU66026A1 (enrdf_load_stackoverflow) | 1973-01-17 |
| CH551383A (fr) | 1974-07-15 |
| JPS4834837A (enrdf_load_stackoverflow) | 1973-05-22 |
| ES406354A1 (es) | 1975-10-01 |
| NL7212197A (enrdf_load_stackoverflow) | 1973-03-13 |
| CA983957A (en) | 1976-02-17 |
| GB1357256A (en) | 1974-06-19 |
| PL85136B1 (enrdf_load_stackoverflow) | 1976-04-30 |
| HU167519B (enrdf_load_stackoverflow) | 1975-10-28 |
| BE788420A (fr) | 1973-01-02 |
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