DE2542196A1 - Verfahren zur herstellung von carnitin - Google Patents
Verfahren zur herstellung von carnitinInfo
- Publication number
- DE2542196A1 DE2542196A1 DE19752542196 DE2542196A DE2542196A1 DE 2542196 A1 DE2542196 A1 DE 2542196A1 DE 19752542196 DE19752542196 DE 19752542196 DE 2542196 A DE2542196 A DE 2542196A DE 2542196 A1 DE2542196 A1 DE 2542196A1
- Authority
- DE
- Germany
- Prior art keywords
- carnitine
- temperatures
- hydrogenation
- trimethylamine
- ester
- 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 14
- 229960004203 carnitine Drugs 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 18
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- -1 Carnitine ester Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PIZFOAZSELZFAS-UHFFFAOYSA-M (4-ethoxy-2,4-dioxobutyl)-trimethylazanium;chloride Chemical compound [Cl-].CCOC(=O)CC(=O)C[N+](C)(C)C PIZFOAZSELZFAS-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000005703 Trimethylamine hydrochloride Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1297074A CH588443A5 (en, 2012) | 1974-09-25 | 1974-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2542196A1 true DE2542196A1 (de) | 1976-04-08 |
Family
ID=4388106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752542196 Pending DE2542196A1 (de) | 1974-09-25 | 1975-09-22 | Verfahren zur herstellung von carnitin |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4021480A (en, 2012) |
| BE (1) | BE833829A (en, 2012) |
| CA (1) | CA1052816A (en, 2012) |
| CH (1) | CH588443A5 (en, 2012) |
| DE (1) | DE2542196A1 (en, 2012) |
| DK (1) | DK428775A (en, 2012) |
| FR (1) | FR2286127A1 (en, 2012) |
| NL (1) | NL7510998A (en, 2012) |
| SU (1) | SU569281A3 (en, 2012) |
| ZA (1) | ZA755848B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4788322A (en) * | 1987-07-31 | 1988-11-29 | Merck & Co., Inc. | Process for preparing ACHPA |
| JPH0678277B2 (ja) * | 1988-02-19 | 1994-10-05 | 高砂香料工業株式会社 | 光学活性アルコールおよびその誘導体の製造方法 |
| US4827012A (en) * | 1988-02-23 | 1989-05-02 | Basf Corporation | Oxo-ionol carbonates |
| US4992106A (en) * | 1988-02-23 | 1991-02-12 | Basf Corporation | Novel oxo-ionol carbonates useful as tobacco flavorants |
| JPH0641445B2 (ja) * | 1988-12-22 | 1994-06-01 | 高砂香料工業株式会社 | 光学活性カルニチンエステルの製法 |
| IT1254136B (it) * | 1992-01-16 | 1995-09-08 | Sigma Tau Ind Farmaceuti | Esteri di acil carnitine con alcooli alifatici a lunga catena e composizioni farmaceutiche che li contengono, ad attivita' antimicotica. |
| IT1254135B (it) * | 1992-01-16 | 1995-09-08 | Sigma Tau Ind Farmaceuti | Esteri di acil carnitine con alcooli alifatici a lunga catena e composizioni farmaceutiche che li contengono, ad attivita' antibatterica. |
| CN108218732A (zh) * | 2018-03-21 | 2018-06-29 | 杭州海尔希畜牧科技有限公司 | 一种低成本高安全性l-肉碱的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2530627A (en) * | 1946-09-06 | 1950-11-21 | Merck & Co Inc | Production of n-acyl allothreonine esters |
| US2933522A (en) * | 1957-11-20 | 1960-04-19 | Du Pont | Process for the preparation of homoserine and alkyl esters thereof |
| US3038007A (en) * | 1958-05-23 | 1962-06-05 | Reeve Edward Wilkins | Process for the preparation of dl-threonine |
| US3135788A (en) * | 1959-09-28 | 1964-06-02 | Nihon Zoki Seiyaku Kabushikika | Preparation of dl-carnitine hydrochloride from trimethylamine hydrochloride and epihalogenohydrin |
-
1974
- 1974-09-25 CH CH1297074A patent/CH588443A5/xx not_active IP Right Cessation
-
1975
- 1975-09-12 ZA ZA00755848A patent/ZA755848B/xx unknown
- 1975-09-18 NL NL7510998A patent/NL7510998A/xx not_active Application Discontinuation
- 1975-09-22 DE DE19752542196 patent/DE2542196A1/de active Pending
- 1975-09-23 SU SU7502174607A patent/SU569281A3/ru active
- 1975-09-24 DK DK428775A patent/DK428775A/da unknown
- 1975-09-24 CA CA236,266A patent/CA1052816A/en not_active Expired
- 1975-09-25 BE BE160387A patent/BE833829A/xx unknown
- 1975-09-25 US US05/616,848 patent/US4021480A/en not_active Expired - Lifetime
- 1975-09-25 FR FR7529402A patent/FR2286127A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CH588443A5 (en, 2012) | 1977-06-15 |
| CA1052816A (en) | 1979-04-17 |
| DK428775A (da) | 1976-03-26 |
| NL7510998A (nl) | 1976-03-29 |
| ZA755848B (en) | 1976-08-25 |
| SU569281A3 (ru) | 1977-08-15 |
| FR2286127A1 (fr) | 1976-04-23 |
| BE833829A (fr) | 1976-03-25 |
| US4021480A (en) | 1977-05-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |