DE2114614C3 - Verfahren zur Herstellung von tertiäären aliphatischen Aminen - Google Patents
Verfahren zur Herstellung von tertiäären aliphatischen AminenInfo
- Publication number
- DE2114614C3 DE2114614C3 DE2114614A DE2114614A DE2114614C3 DE 2114614 C3 DE2114614 C3 DE 2114614C3 DE 2114614 A DE2114614 A DE 2114614A DE 2114614 A DE2114614 A DE 2114614A DE 2114614 C3 DE2114614 C3 DE 2114614C3
- Authority
- DE
- Germany
- Prior art keywords
- alcohol
- mixture
- reaction
- alcohols
- aliphatic
- 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
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims 3
- 150000003510 tertiary aliphatic amines Chemical class 0.000 title claims 2
- 238000006243 chemical reaction Methods 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 16
- 239000007789 gas Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 4
- -1 aliphatic alcohols Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 6
- 125000001931 aliphatic group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 3
- 238000010533 azeotropic distillation Methods 0.000 claims 2
- 229910017052 cobalt Inorganic materials 0.000 claims 2
- 239000010941 cobalt Substances 0.000 claims 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 2
- 238000006297 dehydration reaction Methods 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims 1
- 239000004435 Oxo alcohol Substances 0.000 claims 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 210000003608 fece Anatomy 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000007037 hydroformylation reaction Methods 0.000 claims 1
- 239000010871 livestock manure Substances 0.000 claims 1
- 229910021645 metal ion Inorganic materials 0.000 claims 1
- 238000005272 metallurgy Methods 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 150000003138 primary alcohols Chemical class 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000005496 tempering Methods 0.000 claims 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 claims 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 4
- 239000004439 Isononyl alcohol Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- YGLJGOMFUHQSBN-UHFFFAOYSA-N 7-methyl-n,n-bis(7-methyloctyl)octan-1-amine Chemical compound CC(C)CCCCCCN(CCCCCCC(C)C)CCCCCCC(C)C YGLJGOMFUHQSBN-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- KHFRJOPGKUBZLL-UHFFFAOYSA-N 7-methyl-n-(7-methyloctyl)octan-1-amine Chemical compound CC(C)CCCCCCNCCCCCCC(C)C KHFRJOPGKUBZLL-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
- B01J8/20—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles with liquid as a fluidising medium
- B01J8/22—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles with liquid as a fluidising medium gas being introduced into the liquid
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2114614A DE2114614C3 (de) | 1971-03-26 | 1971-03-26 | Verfahren zur Herstellung von tertiäären aliphatischen Aminen |
| NL7107569A NL7107569A (enExample) | 1971-03-26 | 1971-06-02 | |
| US00234531A US3803239A (en) | 1971-03-26 | 1972-03-14 | Process for the production of tertiary amines |
| DD161698A DD95572A5 (enExample) | 1971-03-26 | 1972-03-17 | |
| SE03563/72A SE368565B (enExample) | 1971-03-26 | 1972-03-20 | |
| ZA721874A ZA721874B (en) | 1971-03-26 | 1972-03-20 | A process for the production of tertiary amines |
| SU1762986A SU452090A3 (ru) | 1971-03-26 | 1972-03-22 | Способ получени третичных аминов |
| CA138,033A CA995692A (en) | 1971-03-26 | 1972-03-24 | Process for the production of tertiary amines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2114614A DE2114614C3 (de) | 1971-03-26 | 1971-03-26 | Verfahren zur Herstellung von tertiäären aliphatischen Aminen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2114614A1 DE2114614A1 (de) | 1972-10-05 |
| DE2114614B2 DE2114614B2 (de) | 1974-04-25 |
| DE2114614C3 true DE2114614C3 (de) | 1974-11-21 |
Family
ID=5802792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2114614A Expired DE2114614C3 (de) | 1971-03-26 | 1971-03-26 | Verfahren zur Herstellung von tertiäären aliphatischen Aminen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3803239A (enExample) |
| CA (1) | CA995692A (enExample) |
| DD (1) | DD95572A5 (enExample) |
| DE (1) | DE2114614C3 (enExample) |
| NL (1) | NL7107569A (enExample) |
| SE (1) | SE368565B (enExample) |
| SU (1) | SU452090A3 (enExample) |
| ZA (1) | ZA721874B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2625196C2 (de) * | 1976-06-04 | 1988-09-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von tertiären Aminen |
| DE2639648A1 (de) * | 1976-09-03 | 1978-03-16 | Basf Ag | Verfahren zur herstellung von tertiaeren aminen |
| BE530219A (enExample) * | 1976-05-14 | |||
| US4418214A (en) * | 1982-10-18 | 1983-11-29 | Air Products And Chemicals, Inc. | Hydrogen recovery by alcohol scrubbing in alcohol amination |
| DE3627592A1 (de) * | 1986-08-14 | 1988-02-25 | Basf Ag | Verfahren zur herstellung von trialkylaminen |
-
1971
- 1971-03-26 DE DE2114614A patent/DE2114614C3/de not_active Expired
- 1971-06-02 NL NL7107569A patent/NL7107569A/xx unknown
-
1972
- 1972-03-14 US US00234531A patent/US3803239A/en not_active Expired - Lifetime
- 1972-03-17 DD DD161698A patent/DD95572A5/xx unknown
- 1972-03-20 ZA ZA721874A patent/ZA721874B/xx unknown
- 1972-03-20 SE SE03563/72A patent/SE368565B/xx unknown
- 1972-03-22 SU SU1762986A patent/SU452090A3/ru active
- 1972-03-24 CA CA138,033A patent/CA995692A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ZA721874B (en) | 1972-12-27 |
| DD95572A5 (enExample) | 1973-02-12 |
| CA995692A (en) | 1976-08-24 |
| US3803239A (en) | 1974-04-09 |
| DE2114614A1 (de) | 1972-10-05 |
| SU452090A3 (ru) | 1974-11-30 |
| NL7107569A (enExample) | 1972-09-28 |
| SE368565B (enExample) | 1974-07-08 |
| DE2114614B2 (de) | 1974-04-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |