DE2414930C2 - Verfahren zur kontinuierlichen Herstellung von Hexamethylenimin - Google Patents
Verfahren zur kontinuierlichen Herstellung von HexamethyleniminInfo
- Publication number
- DE2414930C2 DE2414930C2 DE2414930A DE2414930A DE2414930C2 DE 2414930 C2 DE2414930 C2 DE 2414930C2 DE 2414930 A DE2414930 A DE 2414930A DE 2414930 A DE2414930 A DE 2414930A DE 2414930 C2 DE2414930 C2 DE 2414930C2
- Authority
- DE
- Germany
- Prior art keywords
- hexamethyleneimine
- hexamethylenediamine
- reaction
- hydrogen
- continuous production
- 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
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 13
- 238000010924 continuous production Methods 0.000 title claims 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 36
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 11
- 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 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 239000011572 manganese Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- -1 polymethylene Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2414930A DE2414930C2 (de) | 1974-03-28 | 1974-03-28 | Verfahren zur kontinuierlichen Herstellung von Hexamethylenimin |
| US05/556,469 US4229346A (en) | 1974-03-28 | 1975-03-07 | Production of hexamethylenimine |
| NL7503442A NL7503442A (nl) | 1974-03-28 | 1975-03-21 | Werkwijze voor het bereiden van hexamethyleen- imine. |
| IT21636/75A IT1034523B (it) | 1974-03-28 | 1975-03-24 | Processo per la produzione di esametilenimina |
| FR7509451A FR2265745B3 (en:Method) | 1974-03-28 | 1975-03-26 | |
| BE154782A BE827199A (fr) | 1974-03-28 | 1975-03-26 | Procede de preparation de l'hexamethylene-imine par cyclisation de l'hexamethylene-diamine et separation d'ammoniac en presence d'hydrogene et d'un catalyseur d'hydrogenation |
| GB12853/75A GB1492847A (en) | 1974-03-28 | 1975-03-27 | Production of hexamethylenimine |
| JP50037025A JPS6031828B2 (ja) | 1974-03-28 | 1975-03-28 | ヘキサメチレンイミンの製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2414930A DE2414930C2 (de) | 1974-03-28 | 1974-03-28 | Verfahren zur kontinuierlichen Herstellung von Hexamethylenimin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2414930A1 DE2414930A1 (de) | 1975-10-23 |
| DE2414930C2 true DE2414930C2 (de) | 1983-07-07 |
Family
ID=5911400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2414930A Expired DE2414930C2 (de) | 1974-03-28 | 1974-03-28 | Verfahren zur kontinuierlichen Herstellung von Hexamethylenimin |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4229346A (en:Method) |
| JP (1) | JPS6031828B2 (en:Method) |
| BE (1) | BE827199A (en:Method) |
| DE (1) | DE2414930C2 (en:Method) |
| FR (1) | FR2265745B3 (en:Method) |
| GB (1) | GB1492847A (en:Method) |
| IT (1) | IT1034523B (en:Method) |
| NL (1) | NL7503442A (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1026754A (en) * | 1974-07-25 | 1978-02-21 | Yasunobu Takahashi | Preparation of hexamethyleneimine |
| JPS6428122U (en:Method) * | 1987-08-12 | 1989-02-17 | ||
| US4937336A (en) * | 1988-12-05 | 1990-06-26 | E. I. Du Pont De Nemours And Company | Process for the preparation of hexamethylene imine |
| DE19842905A1 (de) | 1998-09-18 | 2000-03-23 | Basf Ag | Verfahren zur gleichzeitigen Herstellung eines cyclischen Lactams und eines cyclischen Amins |
| DE19842900A1 (de) | 1998-09-18 | 2000-03-23 | Basf Ag | Verfahren zur gemeinsamen Herstellung eines cyclischen Lactams und eines cyclischen Amins |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA920606A (en) * | 1971-01-19 | 1973-02-06 | J. Kershaw Bernard | Manufacture of hexamethyleneimine |
| JPS5163184A (en:Method) * | 1974-11-28 | 1976-06-01 | Asahi Chemical Ind |
-
1974
- 1974-03-28 DE DE2414930A patent/DE2414930C2/de not_active Expired
-
1975
- 1975-03-07 US US05/556,469 patent/US4229346A/en not_active Expired - Lifetime
- 1975-03-21 NL NL7503442A patent/NL7503442A/xx not_active Application Discontinuation
- 1975-03-24 IT IT21636/75A patent/IT1034523B/it active
- 1975-03-26 BE BE154782A patent/BE827199A/xx not_active IP Right Cessation
- 1975-03-26 FR FR7509451A patent/FR2265745B3/fr not_active Expired
- 1975-03-27 GB GB12853/75A patent/GB1492847A/en not_active Expired
- 1975-03-28 JP JP50037025A patent/JPS6031828B2/ja not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50130775A (en:Method) | 1975-10-16 |
| DE2414930A1 (de) | 1975-10-23 |
| FR2265745B3 (en:Method) | 1977-12-02 |
| IT1034523B (it) | 1979-10-10 |
| BE827199A (fr) | 1975-09-26 |
| NL7503442A (nl) | 1975-09-30 |
| FR2265745A1 (en:Method) | 1975-10-24 |
| US4229346A (en) | 1980-10-21 |
| JPS6031828B2 (ja) | 1985-07-24 |
| GB1492847A (en) | 1977-11-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07D295/02 |
|
| 8126 | Change of the secondary classification |
Ipc: ENTFAELLT |
|
| 8181 | Inventor (new situation) |
Free format text: TOUSSAINT, HERBERT, DIPL.-CHEM. DR., 6710 FRANKENTHAL, DE ADELSBERGER, KLAUS, DIPL.-CHEM. DR., 6903NECKARGEMUEND, DE HOFFMANN, HERWIG, DIPL.-CHEM. DR., 6710 FRANKENTHAL, DE |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8380 | Miscellaneous part iii |
Free format text: IN SPALTE 4, ZEILE 47 "HEXAMETHYLENDIAMIN" IST ZU AENDERN IN "HEXAMETHYLENIMIN" |
|
| 8339 | Ceased/non-payment of the annual fee |