DE2319360A1 - Verfahren zur herstellung von epsilonaminocapronsaeureamid - Google Patents
Verfahren zur herstellung von epsilonaminocapronsaeureamidInfo
- Publication number
- DE2319360A1 DE2319360A1 DE2319360A DE2319360A DE2319360A1 DE 2319360 A1 DE2319360 A1 DE 2319360A1 DE 2319360 A DE2319360 A DE 2319360A DE 2319360 A DE2319360 A DE 2319360A DE 2319360 A1 DE2319360 A1 DE 2319360A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- aminocaproamide
- liquid ammonia
- pressure
- hydrogen
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001408 amides Chemical class 0.000 title description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
- 239000010941 cobalt Substances 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- ZLHYDRXTDZFRDZ-UHFFFAOYSA-N epsilon-aminocaproamide Chemical compound NCCCCCC(N)=O ZLHYDRXTDZFRDZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- YTIHIRCOUAPRCS-UHFFFAOYSA-N Dl-norleucinamide Chemical compound CCCCC(N)C(N)=O YTIHIRCOUAPRCS-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DTTQUVSBSUGCMS-UHFFFAOYSA-N 6-nitrohexanamide Chemical compound [N+](=O)([O-])CCCCCC(=O)N DTTQUVSBSUGCMS-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- SZNILIWUUKKNPE-UHFFFAOYSA-N 2-nitrocyclohexan-1-one Chemical compound [O-][N+](=O)C1CCCCC1=O SZNILIWUUKKNPE-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- LSTJLLHJASXKIV-UHFFFAOYSA-N amino hexanoate Chemical compound CCCCCC(=O)ON LSTJLLHJASXKIV-UHFFFAOYSA-N 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical compound [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- -1 winding Chemical compound 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyamides (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2319360A DE2319360A1 (de) | 1973-04-17 | 1973-04-17 | Verfahren zur herstellung von epsilonaminocapronsaeureamid |
| NL7404565A NL7404565A (enExample) | 1973-04-17 | 1974-04-03 | |
| IT21239/74A IT1012575B (it) | 1973-04-17 | 1974-04-10 | Processo per la preparazione di epsilon amminocarpronamid |
| BE143212A BE813722A (fr) | 1973-04-17 | 1974-04-12 | Procede de preparation d'epsilon-aminocapronamide |
| DD177909A DD112986A5 (enExample) | 1973-04-17 | 1974-04-15 | |
| JP49042357A JPS505319A (enExample) | 1973-04-17 | 1974-04-17 | |
| FR7413306A FR2226388A1 (en) | 1973-04-17 | 1974-04-17 | Epsilon-aminocaproamide prodn in liq. ammonia - by catalytic hydrogen-ation of epsilon -nitrocaproamide under pressure |
| ES425412A ES425412A1 (es) | 1973-04-17 | 1974-04-17 | Procedimiento para la obtencion de epsilon-aminocaprnamida. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2319360A DE2319360A1 (de) | 1973-04-17 | 1973-04-17 | Verfahren zur herstellung von epsilonaminocapronsaeureamid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2319360A1 true DE2319360A1 (de) | 1974-11-07 |
Family
ID=5878367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2319360A Pending DE2319360A1 (de) | 1973-04-17 | 1973-04-17 | Verfahren zur herstellung von epsilonaminocapronsaeureamid |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS505319A (enExample) |
| BE (1) | BE813722A (enExample) |
| DD (1) | DD112986A5 (enExample) |
| DE (1) | DE2319360A1 (enExample) |
| ES (1) | ES425412A1 (enExample) |
| FR (1) | FR2226388A1 (enExample) |
| IT (1) | IT1012575B (enExample) |
| NL (1) | NL7404565A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5379792U (enExample) * | 1976-12-06 | 1978-07-03 | ||
| FR2497797A1 (fr) * | 1981-01-13 | 1982-07-16 | Synthelabo | Procede de preparation de l'amino-4 butyramide |
| JPS63196761A (ja) * | 1987-02-05 | 1988-08-15 | 和歌山鉄工株式会社 | センタリング兼拡布装置 |
-
1973
- 1973-04-17 DE DE2319360A patent/DE2319360A1/de active Pending
-
1974
- 1974-04-03 NL NL7404565A patent/NL7404565A/xx unknown
- 1974-04-10 IT IT21239/74A patent/IT1012575B/it active
- 1974-04-12 BE BE143212A patent/BE813722A/xx unknown
- 1974-04-15 DD DD177909A patent/DD112986A5/xx unknown
- 1974-04-17 ES ES425412A patent/ES425412A1/es not_active Expired
- 1974-04-17 FR FR7413306A patent/FR2226388A1/fr active Granted
- 1974-04-17 JP JP49042357A patent/JPS505319A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES425412A1 (es) | 1976-06-01 |
| DD112986A5 (enExample) | 1975-05-12 |
| FR2226388B3 (enExample) | 1977-02-18 |
| BE813722A (fr) | 1974-10-14 |
| FR2226388A1 (en) | 1974-11-15 |
| NL7404565A (enExample) | 1974-10-21 |
| IT1012575B (it) | 1977-03-10 |
| JPS505319A (enExample) | 1975-01-21 |
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