DE2347905A1 - Verfahren zur herstellung von heptamethylenimin - Google Patents
Verfahren zur herstellung von heptamethyleniminInfo
- Publication number
- DE2347905A1 DE2347905A1 DE19732347905 DE2347905A DE2347905A1 DE 2347905 A1 DE2347905 A1 DE 2347905A1 DE 19732347905 DE19732347905 DE 19732347905 DE 2347905 A DE2347905 A DE 2347905A DE 2347905 A1 DE2347905 A1 DE 2347905A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- yield
- reaction
- lactam
- hydrogenation
- 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 26
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 22
- 239000012071 phase Substances 0.000 claims description 8
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 7
- CJYXCQLOZNIMFP-UHFFFAOYSA-N azocan-2-one Chemical compound O=C1CCCCCCN1 CJYXCQLOZNIMFP-UHFFFAOYSA-N 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 5
- -1 aminohexyl Chemical group 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- ZFYIQPIHXRFFCZ-QMMMGPOBSA-N (2s)-2-(cyclohexylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC1CCCCC1 ZFYIQPIHXRFFCZ-QMMMGPOBSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000530268 Lycaena heteronea Species 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate trihydrate Substances [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 150000003571 thiolactams Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/02—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom not condensed with other 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)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001280 HU170390B (enrdf_load_stackoverflow) | 1972-09-29 | 1972-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2347905A1 true DE2347905A1 (de) | 1974-04-04 |
Family
ID=10994459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732347905 Pending DE2347905A1 (de) | 1972-09-29 | 1973-09-24 | Verfahren zur herstellung von heptamethylenimin |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4985079A (enrdf_load_stackoverflow) |
| CA (1) | CA1015359A (enrdf_load_stackoverflow) |
| DE (1) | DE2347905A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2201291B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1403143A (enrdf_load_stackoverflow) |
| HU (1) | HU170390B (enrdf_load_stackoverflow) |
| SU (1) | SU512699A3 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4786727A (en) * | 1978-08-26 | 1988-11-22 | Basf Aktiengesellschaft | Preparation of hexamethyleneimine |
-
1972
- 1972-09-29 HU HUCI001280 patent/HU170390B/hu unknown
-
1973
- 1973-09-24 DE DE19732347905 patent/DE2347905A1/de active Pending
- 1973-09-27 GB GB4538373A patent/GB1403143A/en not_active Expired
- 1973-09-28 FR FR7334806A patent/FR2201291B1/fr not_active Expired
- 1973-09-28 CA CA182,166A patent/CA1015359A/en not_active Expired
- 1973-09-28 SU SU1965042A patent/SU512699A3/ru active
- 1973-09-28 JP JP48110102A patent/JPS4985079A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4786727A (en) * | 1978-08-26 | 1988-11-22 | Basf Aktiengesellschaft | Preparation of hexamethyleneimine |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1403143A (en) | 1975-08-13 |
| JPS4985079A (enrdf_load_stackoverflow) | 1974-08-15 |
| FR2201291B1 (enrdf_load_stackoverflow) | 1977-08-19 |
| HU170390B (enrdf_load_stackoverflow) | 1977-06-28 |
| SU512699A3 (ru) | 1976-04-30 |
| CA1015359A (en) | 1977-08-09 |
| FR2201291A1 (enrdf_load_stackoverflow) | 1974-04-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1593272A1 (de) | Verfahren zur Herstellung von Halogen-Tetracyclinen | |
| DE1620191C3 (de) | Verfahren zur Herstellung von am Stickstoff substituierten Derivaten des alpha-Pyrrolidons | |
| DE2347905A1 (de) | Verfahren zur herstellung von heptamethylenimin | |
| DE1795193A1 (de) | Verfahren zur Herstellung von Morphinanderivaten | |
| DE2626676A1 (de) | Verfahren zur herstellung von 2-pyrrolidon | |
| DE1221637B (de) | Verfahren zur Herstellung von Vinylverbindungen | |
| DE2407096A1 (de) | Hydrierungsverfahren mit metallhydroxydkatalysatoren der gruppe viii, die keine traeger enthalten | |
| DE2149917A1 (de) | Verfahren zur Herstellung von 2-Pyrrolidinon | |
| DE1620381A1 (de) | Derivate des 2-Aminopyrazins und Verfahren zu ihrer Herstellung | |
| DE2409313C2 (de) | 1-[2-Pyrrolyl-(1)-phenoxy]-2-hydroxy-3-aminopropan-derivate, Verfahren zu deren Herstellung und pharmazeutische Präparate | |
| DE2249993A1 (de) | Verfahren zur spaltung von ketonen | |
| DE1037464B (de) | Verfahren zur Herstellung unsymmetrischer Dialkylhydrazine durch katalytische Reduktion von Dialkylnitrosaminen | |
| US2739159A (en) | Process for the preparation of tetrahydrofurfurylamine | |
| DE2164392A1 (de) | Verfahren zu der Herstellung von 5-(A-Aminobutyl)-hydantoin | |
| DE3020298C2 (de) | Verfahren zur Herstellung von 2,2,4,5,5-Pentamethyl-3-formyl-3-pyrrolin | |
| DE2715518C2 (enrdf_load_stackoverflow) | ||
| CH495979A (de) | Verfahren zur Herstellung von substituierten Phenylessigsäureamiden | |
| AT251560B (de) | Verfahren zur Herstellung von neuen Phenylisopropylaminen und deren Salzen | |
| AT291196B (de) | Verfahren zur Herstellung von neuen Rutheniumkomplexen | |
| DE1795034C3 (de) | Racemisches cis-3-(2-Dimethylamino-1 -propyl)-2-methyl-3-phenylindolin, dessen Salze, Verfahren zu deren Herstellung und Arzneimittel | |
| DE1668950C3 (de) | Sulfonamidsubstituierte Benzylaniline Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE2463468C2 (enrdf_load_stackoverflow) | ||
| AT238180B (de) | Verfahren zur Herstellung neuer Pyrrolidinverbindungen | |
| DE1941261B2 (de) | N hoch 1-Glycyl-N hoch 2 (2,3,4trihydroxybenzyl)-hydrazid, Verfahren zu dessen Herstellung sowie dessen Säureadditionssalze und dieses enthaltende Arzneimittel | |
| DE2360407A1 (de) | Herstellung von omega-amino-betaalkoxycarbonsauren estern |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |