DE1618018C3 - Verfahren zur Herstellung von N-Methylbutylamin - Google Patents
Verfahren zur Herstellung von N-MethylbutylaminInfo
- Publication number
- DE1618018C3 DE1618018C3 DE1618018A DE1618018A DE1618018C3 DE 1618018 C3 DE1618018 C3 DE 1618018C3 DE 1618018 A DE1618018 A DE 1618018A DE 1618018 A DE1618018 A DE 1618018A DE 1618018 C3 DE1618018 C3 DE 1618018C3
- Authority
- DE
- Germany
- Prior art keywords
- monomethylamine
- methylbutylamine
- butyraldehyde
- molar ratio
- aqueous
- 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
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 46
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 20
- 150000001299 aldehydes Chemical class 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- MTHFROHDIWGWFD-UHFFFAOYSA-N n-butyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CCCC MTHFROHDIWGWFD-UHFFFAOYSA-N 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000001728 carbonyl compounds Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000004656 dimethylamines Chemical class 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- -1 primary amines Chemical class 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010959 steel Substances 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR55755A FR1492863A (fr) | 1966-03-31 | 1966-03-31 | Perfectionnements aux procédés de fabrication de nu-méthylbutylamine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1618018A1 DE1618018A1 (de) | 1972-03-30 |
| DE1618018B2 DE1618018B2 (de) | 1976-04-22 |
| DE1618018C3 true DE1618018C3 (de) | 1982-06-09 |
Family
ID=8605147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1618018A Expired DE1618018C3 (de) | 1966-03-31 | 1967-03-16 | Verfahren zur Herstellung von N-Methylbutylamin |
Country Status (7)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3976697A (en) * | 1974-10-29 | 1976-08-24 | Texaco Inc. | Preparation of tertiary amines |
| JPS6033423B2 (ja) * | 1980-08-13 | 1985-08-02 | 宇部興産株式会社 | Ｎ−アルキルアルキレンジアミンの製法 |
| JP5911469B2 (ja) | 2010-04-07 | 2016-04-27 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 液相中での非対称第二級ｔｅｒｔ−ブチルアミンの製造方法 |
| US8445726B2 (en) | 2010-04-07 | 2013-05-21 | Basf Se | Process for preparing unsymmetric secondary tert-butylamines in the liquid phase |
| CN102786426A (zh) * | 2012-08-28 | 2012-11-21 | 上海化工研究院 | 一种稳定同位素标记莱克多巴胺的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB615715A (en) * | 1945-02-22 | 1949-01-11 | Sharples Chemicals Inc | Improvements in or relating to amines and process of forming same |
| US2809995A (en) * | 1951-12-31 | 1957-10-15 | Ruhrchemie Ag | Production of amines |
| US2828343A (en) * | 1952-10-18 | 1958-03-25 | Commercial Solvents Corp | Process for the production of secondary amines |
-
1966
- 1966-03-31 FR FR55755A patent/FR1492863A/fr not_active Expired
-
1967
- 1967-02-28 BE BE694749D patent/BE694749A/xx not_active IP Right Cessation
- 1967-03-16 DE DE1618018A patent/DE1618018C3/de not_active Expired
- 1967-03-23 LU LU53270D patent/LU53270A1/xx unknown
- 1967-03-27 US US625977A patent/US3442951A/en not_active Expired - Lifetime
- 1967-03-29 GB GB14329/67A patent/GB1116610A/en not_active Expired
- 1967-03-30 NL NL676704542A patent/NL154721B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1116610A (en) | 1968-06-06 |
| FR1492863A (fr) | 1967-08-25 |
| NL154721B (nl) | 1977-10-17 |
| NL6704542A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-10-02 |
| DE1618018A1 (de) | 1972-03-30 |
| US3442951A (en) | 1969-05-06 |
| DE1618018B2 (de) | 1976-04-22 |
| BE694749A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-07-31 |
| LU53270A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-05-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8380 | Miscellaneous part iii |
Free format text: DER VERTRETER IST NACHZUTRAGEN EGGERT, H., DIPL.-CHEM., DR., PAT.-ANW., 5000 KOELN |