CH377359A - Verfahren zur Herstellung von am Kohlenstoff des Piperazinringes substituierten Piperazinen - Google Patents
Verfahren zur Herstellung von am Kohlenstoff des Piperazinringes substituierten PiperazinenInfo
- Publication number
- CH377359A CH377359A CH6616058A CH6616058A CH377359A CH 377359 A CH377359 A CH 377359A CH 6616058 A CH6616058 A CH 6616058A CH 6616058 A CH6616058 A CH 6616058A CH 377359 A CH377359 A CH 377359A
- Authority
- CH
- Switzerland
- Prior art keywords
- catalyst
- oxy
- mixture
- piperazine
- propyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 36
- 125000004193 piperazinyl group Chemical group 0.000 title claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims description 11
- 229910052799 carbon Inorganic materials 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000003054 catalyst Substances 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 30
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 24
- 150000004985 diamines Chemical class 0.000 claims description 21
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- 150000004885 piperazines Chemical group 0.000 claims description 12
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 6
- 229910000990 Ni alloy Inorganic materials 0.000 claims 1
- 229940012017 ethylenediamine Drugs 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 9
- 229910000564 Raney nickel Inorganic materials 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- IFNWESYYDINUHV-UHFFFAOYSA-N 2,6-dimethylpiperazine Chemical compound CC1CNCC(C)N1 IFNWESYYDINUHV-UHFFFAOYSA-N 0.000 description 3
- VXVCTVOKVWCZOF-UHFFFAOYSA-N 2-ethyl-5-methylpiperazine Chemical compound CCC1CNC(C)CN1 VXVCTVOKVWCZOF-UHFFFAOYSA-N 0.000 description 3
- WWMALGPGDWZHRB-UHFFFAOYSA-N 2-ethyl-6-methylpiperazine Chemical compound CCC1CNCC(C)N1 WWMALGPGDWZHRB-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl radicals Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 2
- OMEMBAXECFIRSG-UHFFFAOYSA-N 2,3,5-trimethylpiperazine Chemical compound CC1CNC(C)C(C)N1 OMEMBAXECFIRSG-UHFFFAOYSA-N 0.000 description 2
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 2
- COWPTMLRSANSMQ-UHFFFAOYSA-N 2,3-dimethylpiperazine Chemical compound CC1NCCNC1C COWPTMLRSANSMQ-UHFFFAOYSA-N 0.000 description 2
- NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 description 2
- DXOHZOPKNFZZAD-UHFFFAOYSA-N 2-ethylpiperazine Chemical compound CCC1CNCCN1 DXOHZOPKNFZZAD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical class CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- PIPWSBOFSUJCCO-UHFFFAOYSA-N 2,2-dimethylpiperazine Chemical compound CC1(C)CNCCN1 PIPWSBOFSUJCCO-UHFFFAOYSA-N 0.000 description 1
- FNJWLOHHZVGUIX-UHFFFAOYSA-N 2-propylpiperazine Chemical compound CCCC1CNCCN1 FNJWLOHHZVGUIX-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- VNNRSPGTAMTISX-UHFFFAOYSA-N chromium nickel Chemical compound [Cr].[Ni] VNNRSPGTAMTISX-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- XWINCPYLXQTPQV-UHFFFAOYSA-N piperazine Chemical class C1CNCCN1.C1CNCCN1 XWINCPYLXQTPQV-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL105389D NL105389C (cs) | 1958-11-14 | ||
| CH6616058A CH377359A (de) | 1958-11-14 | 1958-11-14 | Verfahren zur Herstellung von am Kohlenstoff des Piperazinringes substituierten Piperazinen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6616058A CH377359A (de) | 1958-11-14 | 1958-11-14 | Verfahren zur Herstellung von am Kohlenstoff des Piperazinringes substituierten Piperazinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH377359A true CH377359A (de) | 1964-05-15 |
Family
ID=4526937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6616058A CH377359A (de) | 1958-11-14 | 1958-11-14 | Verfahren zur Herstellung von am Kohlenstoff des Piperazinringes substituierten Piperazinen |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH377359A (cs) |
| NL (1) | NL105389C (cs) |
-
0
- NL NL105389D patent/NL105389C/xx active
-
1958
- 1958-11-14 CH CH6616058A patent/CH377359A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL105389C (cs) |
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