DE2841585C3 - Verfahren zur Herstellung von 2.2-Dialkyl-pentan-1.5-diaminen - Google Patents
Verfahren zur Herstellung von 2.2-Dialkyl-pentan-1.5-diaminenInfo
- Publication number
- DE2841585C3 DE2841585C3 DE19782841585 DE2841585A DE2841585C3 DE 2841585 C3 DE2841585 C3 DE 2841585C3 DE 19782841585 DE19782841585 DE 19782841585 DE 2841585 A DE2841585 A DE 2841585A DE 2841585 C3 DE2841585 C3 DE 2841585C3
- Authority
- DE
- Germany
- Prior art keywords
- cyano
- dialkyl
- catalyst
- reaction
- diamines
- 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
- 238000002360 preparation method Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 15
- 229910021529 ammonia Inorganic materials 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- CWNRYVQFAMHXLM-UHFFFAOYSA-N 2-formylbutanenitrile Chemical class CCC(C=O)C#N CWNRYVQFAMHXLM-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 238000005276 aerator Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052566 spinel group Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- HKJVKIURQSVEQB-UHFFFAOYSA-N 4,4-dimethyl-5-oxopentanenitrile Chemical compound O=CC(C)(C)CCC#N HKJVKIURQSVEQB-UHFFFAOYSA-N 0.000 description 1
- KBJKNUWIYZFLGT-UHFFFAOYSA-N 4-ethyl-4-formyloctanenitrile Chemical compound CCCCC(CC)(C=O)CCC#N KBJKNUWIYZFLGT-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical class CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- -1 aluminum silicates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- ASKVAEGIVYSGNY-UHFFFAOYSA-L cobalt(ii) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782841585 DE2841585C3 (de) | 1978-09-25 | 1978-09-25 | Verfahren zur Herstellung von 2.2-Dialkyl-pentan-1.5-diaminen |
| EP19790103563 EP0010179B1 (de) | 1978-09-25 | 1979-09-21 | Verfahren zur Herstellung von 2.2-Dialkyl-pentan-1.5-diaminen und die Verbindungen N-(4-Cyano-2.2-diethyl-butyl)-4-cyano-2.2-diethyl-butyliden-imin und N-(4-Cyano-2-n-butyl-2-ethyl-butyl)-4-cyano-2-n-butyl-2-ethyl-butyliden-imin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782841585 DE2841585C3 (de) | 1978-09-25 | 1978-09-25 | Verfahren zur Herstellung von 2.2-Dialkyl-pentan-1.5-diaminen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2841585A1 DE2841585A1 (de) | 1980-03-27 |
| DE2841585B2 DE2841585B2 (de) | 1981-02-05 |
| DE2841585C3 true DE2841585C3 (de) | 1987-07-30 |
Family
ID=6050326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782841585 Expired DE2841585C3 (de) | 1978-09-25 | 1978-09-25 | Verfahren zur Herstellung von 2.2-Dialkyl-pentan-1.5-diaminen |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0010179B1 (US06534493-20030318-C00166.png) |
| DE (1) | DE2841585C3 (US06534493-20030318-C00166.png) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0394967A1 (en) * | 1989-04-25 | 1990-10-31 | Union Carbide Chemicals And Plastics Company, Inc. | Reductive amination of carbonylnitriles and similar compounds |
| EP0394968A1 (en) * | 1989-04-25 | 1990-10-31 | Union Carbide Chemicals And Plastics Company, Inc. | Amination of carbonyls |
| DE59106607D1 (de) * | 1990-03-30 | 1995-11-09 | Basf Ag | Verfahren zur Herstellung von 2,2-disubstituierten Pentan-1,5-diaminen. |
| DE4129350A1 (de) * | 1991-09-04 | 1993-03-11 | Basf Ag | Verfahren zur herstellung von pentan-1,5-diaminen |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE572548C (de) * | 1932-03-20 | 1933-03-18 | Hoffmanni La Roche & Co Akt Ge | Verfahren zur Darstellung von Diaminen |
| DE1543516A1 (de) * | 1966-04-28 | 1969-10-23 | Dynamit Nobel Ag | Verfahren zur Herstellung von Diaminen |
| FR1525149A (fr) * | 1967-03-08 | 1968-05-17 | Melle Usines Sa | Procédé de fabrication d'amines primaires |
| NO781420L (no) * | 1977-04-26 | 1978-10-27 | Anic Spa | Fremgangsmaate for fremstilling av dinitriler og derivater derav |
-
1978
- 1978-09-25 DE DE19782841585 patent/DE2841585C3/de not_active Expired
-
1979
- 1979-09-21 EP EP19790103563 patent/EP0010179B1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0010179B1 (de) | 1982-05-19 |
| DE2841585B2 (de) | 1981-02-05 |
| DE2841585A1 (de) | 1980-03-27 |
| EP0010179A1 (de) | 1980-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| 8263 | Opposition against grant of a patent | ||
| 8281 | Inventor (new situation) |
Free format text: FEICHTINGER, HANS, DIPL.-CHEM. DR. CORNILS, BOY, DIPL.-CHEM. DR., 4220 DINSLAKEN, DE PAYER, WOLFGANG, DIPL.-CHEM. DR., 4230 WESEL, DE |
|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HOECHST AG, 6230 FRANKFURT, DE |
|
| 8339 | Ceased/non-payment of the annual fee |