DE2219475A1 - Verfahren zur herstellung von primaeren aminen - Google Patents
Verfahren zur herstellung von primaeren aminenInfo
- Publication number
- DE2219475A1 DE2219475A1 DE19722219475 DE2219475A DE2219475A1 DE 2219475 A1 DE2219475 A1 DE 2219475A1 DE 19722219475 DE19722219475 DE 19722219475 DE 2219475 A DE2219475 A DE 2219475A DE 2219475 A1 DE2219475 A1 DE 2219475A1
- Authority
- DE
- Germany
- Prior art keywords
- volume
- parts
- ammonia
- reaction
- primary
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 14
- 150000003141 primary amines Chemical class 0.000 title description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 229910021529 ammonia Inorganic materials 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 17
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- 150000001299 aldehydes Chemical class 0.000 claims description 9
- 150000002576 ketones Chemical class 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 150000002739 metals Chemical class 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- -1 aliphatic amines Chemical class 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
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 3
- 229910000684 Cobalt-chrome Inorganic materials 0.000 claims description 2
- 229910018487 Ni—Cr Inorganic materials 0.000 claims description 2
- VNNRSPGTAMTISX-UHFFFAOYSA-N chromium nickel Chemical compound [Cr].[Ni] VNNRSPGTAMTISX-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 11
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 6
- WTPYRCJDOZVZON-UHFFFAOYSA-N 3,5,5-Trimethylhexanal Chemical compound O=CCC(C)CC(C)(C)C WTPYRCJDOZVZON-UHFFFAOYSA-N 0.000 description 6
- DZDVMKLYUKZMKK-UHFFFAOYSA-N 7-methyloctan-1-amine Chemical compound CC(C)CCCCCCN DZDVMKLYUKZMKK-UHFFFAOYSA-N 0.000 description 6
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004439 Isononyl alcohol Substances 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- XGQJZNCFDLXSIJ-UHFFFAOYSA-N pentadecanal Chemical compound CCCCCCCCCCCCCCC=O XGQJZNCFDLXSIJ-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000376 reactant Substances 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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 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
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
- VYZAMTAEIAYCRO-YPZZEJLDSA-N chromium-50 Chemical group [50Cr] VYZAMTAEIAYCRO-YPZZEJLDSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722219475 DE2219475A1 (de) | 1972-04-21 | 1972-04-21 | Verfahren zur herstellung von primaeren aminen |
| FR7313560A FR2180808B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-04-21 | 1973-04-13 | |
| GB1828173A GB1421278A (en) | 1972-04-21 | 1973-04-16 | Process for the production of primary amines |
| IT4948273A IT980240B (it) | 1972-04-21 | 1973-04-16 | Procedimento per la preparazione di ammine primarie |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722219475 DE2219475A1 (de) | 1972-04-21 | 1972-04-21 | Verfahren zur herstellung von primaeren aminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2219475A1 true DE2219475A1 (de) | 1973-11-08 |
Family
ID=5842762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722219475 Ceased DE2219475A1 (de) | 1972-04-21 | 1972-04-21 | Verfahren zur herstellung von primaeren aminen |
Country Status (4)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6525222B2 (en) | 1999-12-06 | 2003-02-25 | Basf Aktiengesellschaft | Process for preparing amines |
| US6563004B2 (en) | 1999-12-06 | 2003-05-13 | Basf Aktiengesellschaft | Process for preparing monoisopropylamine |
| DE102012016433A1 (de) * | 2012-08-17 | 2014-05-15 | Oxea Gmbh | Kontinuierliches Verfahren zur Herstellung primärer aliphatischer Amine aus Aldehyden |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR628641A (fr) * | 1926-02-09 | 1927-10-26 | Ig Farbenindustrie Ag | Procédé pour la production d'amines primaires aliphatiques et cycliques |
-
1972
- 1972-04-21 DE DE19722219475 patent/DE2219475A1/de not_active Ceased
-
1973
- 1973-04-13 FR FR7313560A patent/FR2180808B1/fr not_active Expired
- 1973-04-16 GB GB1828173A patent/GB1421278A/en not_active Expired
- 1973-04-16 IT IT4948273A patent/IT980240B/it active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6525222B2 (en) | 1999-12-06 | 2003-02-25 | Basf Aktiengesellschaft | Process for preparing amines |
| US6563004B2 (en) | 1999-12-06 | 2003-05-13 | Basf Aktiengesellschaft | Process for preparing monoisopropylamine |
| DE102012016433A1 (de) * | 2012-08-17 | 2014-05-15 | Oxea Gmbh | Kontinuierliches Verfahren zur Herstellung primärer aliphatischer Amine aus Aldehyden |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1421278A (en) | 1976-01-14 |
| IT980240B (it) | 1974-09-30 |
| FR2180808A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-11-30 |
| FR2180808B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8131 | Rejection |