DE3420391C1 - Verfahren zur Herstellung von D,L-Carnitinamidchlorid - Google Patents
Verfahren zur Herstellung von D,L-CarnitinamidchloridInfo
- Publication number
- DE3420391C1 DE3420391C1 DE3420391A DE3420391A DE3420391C1 DE 3420391 C1 DE3420391 C1 DE 3420391C1 DE 3420391 A DE3420391 A DE 3420391A DE 3420391 A DE3420391 A DE 3420391A DE 3420391 C1 DE3420391 C1 DE 3420391C1
- Authority
- DE
- Germany
- Prior art keywords
- chloride
- reaction
- carnitine
- temperature
- preparation
- 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 abstract description 13
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 7
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 18
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- 239000007864 aqueous solution Substances 0.000 abstract description 7
- 150000002825 nitriles Chemical class 0.000 abstract description 7
- 239000000243 solution Substances 0.000 abstract description 7
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 abstract description 5
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- MVOVUKIZAZCBRK-FYZOBXCZSA-N (R)-carnitinamide chloride Chemical compound [Cl-].C[N+](C)(C)C[C@H](O)CC(N)=O MVOVUKIZAZCBRK-FYZOBXCZSA-N 0.000 abstract description 2
- 238000002955 isolation Methods 0.000 abstract 1
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 5
- -1 carnitine nitrile Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229960004203 carnitine Drugs 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- KWIXGIMKELMNGH-UHFFFAOYSA-O carnitinamide Chemical compound C[N+](C)(C)CC(O)CC(N)=O KWIXGIMKELMNGH-UHFFFAOYSA-O 0.000 description 1
- 229960000678 carnitine chloride Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
- Manufacture And Refinement Of Metals (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3420391A DE3420391C1 (de) | 1984-06-01 | 1984-06-01 | Verfahren zur Herstellung von D,L-Carnitinamidchlorid |
| EP85105309A EP0166901B1 (de) | 1984-06-01 | 1985-05-02 | Verfahren zur Herstellung von D,L-Carnitinamidchlorid |
| AT85105309T ATE44728T1 (de) | 1984-06-01 | 1985-05-02 | Verfahren zur herstellung von d,lcarnitinamidchlorid. |
| ES543529A ES8607202A1 (es) | 1984-06-01 | 1985-05-27 | Mejoras en los procedimientos para la produccion de aldehi- dos |
| JP60115554A JPS611649A (ja) | 1984-06-01 | 1985-05-30 | Ｄ，ｌ‐カルニチンアミド‐クロリドの製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3420391A DE3420391C1 (de) | 1984-06-01 | 1984-06-01 | Verfahren zur Herstellung von D,L-Carnitinamidchlorid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3420391C1 true DE3420391C1 (de) | 1985-08-14 |
Family
ID=6237339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3420391A Expired DE3420391C1 (de) | 1984-06-01 | 1984-06-01 | Verfahren zur Herstellung von D,L-Carnitinamidchlorid |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0166901B1 (enExample) |
| JP (1) | JPS611649A (enExample) |
| AT (1) | ATE44728T1 (enExample) |
| DE (1) | DE3420391C1 (enExample) |
| ES (1) | ES8607202A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007037082A1 (ja) * | 2005-09-28 | 2007-04-05 | Mitsubishi Gas Chemical Company, Inc. | カルニチンアミドの製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0056615A2 (de) * | 1981-01-21 | 1982-07-28 | Lonza Ag | Verfahren zur Herstellung von Carnitinamid |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4070394A (en) * | 1976-01-23 | 1978-01-24 | Ethyl Corporation | Carnitine nitrile halide preparation |
-
1984
- 1984-06-01 DE DE3420391A patent/DE3420391C1/de not_active Expired
-
1985
- 1985-05-02 EP EP85105309A patent/EP0166901B1/de not_active Expired
- 1985-05-02 AT AT85105309T patent/ATE44728T1/de not_active IP Right Cessation
- 1985-05-27 ES ES543529A patent/ES8607202A1/es not_active Expired
- 1985-05-30 JP JP60115554A patent/JPS611649A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0056615A2 (de) * | 1981-01-21 | 1982-07-28 | Lonza Ag | Verfahren zur Herstellung von Carnitinamid |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS611649A (ja) | 1986-01-07 |
| ES8607202A1 (es) | 1986-06-01 |
| EP0166901A3 (en) | 1986-10-15 |
| EP0166901B1 (de) | 1989-07-19 |
| EP0166901A2 (de) | 1986-01-08 |
| ATE44728T1 (de) | 1989-08-15 |
| JPH0468304B2 (enExample) | 1992-11-02 |
| ES543529A0 (es) | 1986-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of patent without earlier publication of application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: DEGUSSA-HUELS AG, 60311 FRANKFURT, DE |
|
| 8339 | Ceased/non-payment of the annual fee |