DE2327510C3 - Verfahren zur Herstellung von Dimethylalkylaminen aus Aldehyd-Ammoniak-Verbindungen - Google Patents
Verfahren zur Herstellung von Dimethylalkylaminen aus Aldehyd-Ammoniak-VerbindungenInfo
- Publication number
- DE2327510C3 DE2327510C3 DE19732327510 DE2327510A DE2327510C3 DE 2327510 C3 DE2327510 C3 DE 2327510C3 DE 19732327510 DE19732327510 DE 19732327510 DE 2327510 A DE2327510 A DE 2327510A DE 2327510 C3 DE2327510 C3 DE 2327510C3
- Authority
- DE
- Germany
- Prior art keywords
- ammonia
- parts
- aldehyde
- reaction
- dimethylalkylamines
- 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 14
- 238000002360 preparation method Methods 0.000 title claims 2
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical class CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 title description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 28
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 20
- 229910021529 ammonia Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000007859 condensation product Substances 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 230000000737 periodic effect Effects 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 150000002739 metals Chemical class 0.000 claims 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 6
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 6
- 239000008098 formaldehyde solution Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011651 chromium Substances 0.000 description 5
- 239000012876 carrier material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UFNMLWJTTODWFG-UHFFFAOYSA-N 2-methyl-n-(2-methylprop-1-enyl)propan-1-amine Chemical compound CC(C)CNC=C(C)C UFNMLWJTTODWFG-UHFFFAOYSA-N 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- GDHRQDYGUDOEIZ-UHFFFAOYSA-N n,n,2-trimethylpropan-1-amine Chemical compound CC(C)CN(C)C GDHRQDYGUDOEIZ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- OQADVBLQZQTGLL-UHFFFAOYSA-N 2-ethyl-n,n-dimethylhexan-1-amine Chemical compound CCCCC(CC)CN(C)C OQADVBLQZQTGLL-UHFFFAOYSA-N 0.000 description 1
- AVJRDBHYLUZPBA-UHFFFAOYSA-N 2-ethyl-n-methylhexan-1-amine Chemical compound CCCCC(CC)CNC AVJRDBHYLUZPBA-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- 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 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
- JRPPVSMCCSLJPL-UHFFFAOYSA-N 7-methyloctanal Chemical compound CC(C)CCCCCC=O JRPPVSMCCSLJPL-UHFFFAOYSA-N 0.000 description 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 238000005576 amination reaction Methods 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- POCSLRHOYIGGRA-UHFFFAOYSA-N azane 2-ethylhexanal Chemical compound N.CCCCC(CC)C=O POCSLRHOYIGGRA-UHFFFAOYSA-N 0.000 description 1
- VARPBRSILQXMIW-UHFFFAOYSA-N azane 7-methyloctanal Chemical compound N.C(CCCCCC(C)C)=O VARPBRSILQXMIW-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910000424 chromium(II) oxide Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QKYWADPCTHTJHQ-UHFFFAOYSA-N n,2-dimethylpropan-1-amine Chemical compound CNCC(C)C QKYWADPCTHTJHQ-UHFFFAOYSA-N 0.000 description 1
- GNMQOUGYKPVJRR-UHFFFAOYSA-N nickel(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Ni+3].[Ni+3] GNMQOUGYKPVJRR-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- XVOFZWCCFLVFRR-UHFFFAOYSA-N oxochromium Chemical compound [Cr]=O XVOFZWCCFLVFRR-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732327510 DE2327510C3 (de) | 1973-05-30 | 1973-05-30 | Verfahren zur Herstellung von Dimethylalkylaminen aus Aldehyd-Ammoniak-Verbindungen |
| FR7417706A FR2231663B1 (enExample) | 1973-05-30 | 1974-05-21 | |
| GB2314774A GB1455729A (en) | 1973-05-30 | 1974-05-23 | Process for the production of tertiary amines |
| IT5128074A IT1016104B (it) | 1973-05-30 | 1974-05-29 | Procedimento per la preparazione di ammine terziarie a partire da composti di aldeidi e ammoniaca |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732327510 DE2327510C3 (de) | 1973-05-30 | 1973-05-30 | Verfahren zur Herstellung von Dimethylalkylaminen aus Aldehyd-Ammoniak-Verbindungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2327510A1 DE2327510A1 (de) | 1975-01-02 |
| DE2327510B2 DE2327510B2 (de) | 1980-08-14 |
| DE2327510C3 true DE2327510C3 (de) | 1981-09-24 |
Family
ID=5882555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732327510 Expired DE2327510C3 (de) | 1973-05-30 | 1973-05-30 | Verfahren zur Herstellung von Dimethylalkylaminen aus Aldehyd-Ammoniak-Verbindungen |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE2327510C3 (enExample) |
| FR (1) | FR2231663B1 (enExample) |
| GB (1) | GB1455729A (enExample) |
| IT (1) | IT1016104B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2463120A1 (fr) * | 1979-08-14 | 1981-02-20 | Ugine Kuhlmann | Procede de preparation de la dimethylethylamine |
| DE3060282D1 (en) * | 1979-08-14 | 1982-05-19 | Ugine Kuhlmann | Process for the preparation of dimethylethyl amine |
| SE461095B (sv) * | 1983-09-09 | 1990-01-08 | Berol Kemi Ab | Amineringsfoerfarande med anvaendning av en ruteniumdopad nickel och/eller kovoltkatalysator |
| EP0142868B1 (en) * | 1983-11-22 | 1988-06-01 | Nippon Oil And Fats Company, Limited | Process for producing tertiary amines |
| US5091585A (en) * | 1990-12-21 | 1992-02-25 | Texaco Chemical Company | Continuous preparatin of tertiary aliphatic methyl amines |
-
1973
- 1973-05-30 DE DE19732327510 patent/DE2327510C3/de not_active Expired
-
1974
- 1974-05-21 FR FR7417706A patent/FR2231663B1/fr not_active Expired
- 1974-05-23 GB GB2314774A patent/GB1455729A/en not_active Expired
- 1974-05-29 IT IT5128074A patent/IT1016104B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1455729A (en) | 1976-11-17 |
| FR2231663A1 (enExample) | 1974-12-27 |
| DE2327510B2 (de) | 1980-08-14 |
| DE2327510A1 (de) | 1975-01-02 |
| FR2231663B1 (enExample) | 1977-09-30 |
| IT1016104B (it) | 1977-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |