CN102020575A - Synthesis method of L-carnitine - Google Patents
Synthesis method of L-carnitine Download PDFInfo
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- CN102020575A CN102020575A CN 201010580516 CN201010580516A CN102020575A CN 102020575 A CN102020575 A CN 102020575A CN 201010580516 CN201010580516 CN 201010580516 CN 201010580516 A CN201010580516 A CN 201010580516A CN 102020575 A CN102020575 A CN 102020575A
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- carnitine
- reaction
- trimethylamine
- cyano
- hydroxy
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- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 title claims abstract description 34
- 238000001308 synthesis method Methods 0.000 title abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000006243 chemical reaction Methods 0.000 claims abstract description 51
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 22
- 230000007062 hydrolysis Effects 0.000 claims abstract description 11
- 238000005342 ion exchange Methods 0.000 claims abstract description 8
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 104
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 239000012141 concentrate Substances 0.000 claims description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- 238000010189 synthetic method Methods 0.000 claims description 15
- 238000001953 recrystallisation Methods 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229920001429 chelating resin Polymers 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 12
- 239000012153 distilled water Substances 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- -1 3-cyano-2-hydroxy-propyl group Chemical group 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical group OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002699 waste material Substances 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract description 2
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 8
- 235000021050 feed intake Nutrition 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 2
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 2
- CURCMGVZNYCRNY-UHFFFAOYSA-N trimethylazanium;iodide Chemical compound I.CN(C)C CURCMGVZNYCRNY-UHFFFAOYSA-N 0.000 description 2
- LRWZZZWJMFNZIK-ZJRLKYRESA-N (2s)-2-chloro-3-methyloxirane Chemical compound CC1O[C@H]1Cl LRWZZZWJMFNZIK-ZJRLKYRESA-N 0.000 description 1
- QTNDRVBQVHFPAU-UHFFFAOYSA-N 1-chloro-4-(dimethylamino)butan-2-ol Chemical compound CN(C)CCC(O)CCl QTNDRVBQVHFPAU-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of L-carnitine with a structure shown in a formula (1), which adopts L-(-)-3-cyan-2-hydroxyl propyl trimethylamine halide as a raw material and is prepared by hydrolysis and ion exchange; the hydrolysis is carried out in the following steps: in alkaline solution, hydrogen peroxide is used for hydrolyzing the L-(-)-3-cyan-2-hydroxyl propyl trimethylamine halide, and after full reaction, the hydrolysis reaction liquid is obtained. In the technique disclosed in the invention, the reaction condition is mild, the reaction time is short, the reaction yield is high, three wastes are less, and the implementation value and social and economic benefits are larger.
Description
(1) technical field
The present invention relates to a kind of synthetic method of L-carnitine.
(2) background technology
L-carnitine claims vitamins B again
T, chemistry (3R)-(-) by name-3-hydroxyl-4-(trimethylamine groups) butyric acid has physiologically active widely.International nutrition academic conference in 1985 is classified L-carnitine as under the specified conditions essential nutritive substance.L-carnitine was in health care in recent years, and fields such as fat-reducing are widely used, and at home and abroad supply falls short of demand for its product, has very high practical value.
Before the present invention makes, the more employing of the original synthetic method of the enterprise of domestic production L-carnitine be 1988 Japanese Patent (JP63185947) report be starting raw material with (S)-(+)-epoxy chloropropane, become the quaternary ammonium salt reaction to make 3-chloro-2-hydroxypropyl Trimethylamine 99 halogenide with Trimethylamine 99, be 3-cyano group-2-hydroxypropyl Trimethylamine 99 halogenide through cyaniding again, last hydrolysis and ion-exchange obtain L-carnitine.Its intermediate nitrile compound (L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide) method for hydrolysis adopts the concentrated hydrochloric acid hydrolysis method more, and shortcoming is than higher to equipment requirements.Zeo-karb is often adopted in ion-exchange, and with a large amount of ammoniacal liquor wash-outs, ammonia nitrogen in waste water value height brings very big environmental protection pressure, and therefore, the synthetic method of developing an environmental friendliness and being easy to the L-carnitine of suitability for industrialized production has great importance.
(3) summary of the invention
It is simple to the purpose of this invention is to provide a kind of technology, and production safety is reliable, reaction yield is high, the three wastes are little, easily realize the L-carnitine chemical synthesis process of suitability for industrialized production.
The technical solution used in the present invention is as follows:
A kind of structure is suc as formula the synthetic method of the L-carnitine shown in (I), be to be raw material with the L-(-) shown in the formula (II)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide, make through hydrolysis and ion-exchange, it is characterized in that described hydrolysis adopts following method: in alkaline aqueous solution, with hydrogen peroxide hydrolysis L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide, fully obtain hydrolysis reaction liquid after the reaction.
The present invention recommends described hydrolysis reaction step as follows: in reaction vessel, add L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide, aqueous hydrogen peroxide solution and basic cpd, be warmed up to 50～80 ℃ of reaction 0.5～2h, reaction obtains hydrolysis reaction liquid after finishing; Described L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide: hydrogen peroxide: the ratio of the amount of substance that feeds intake of basic cpd is 1: 4～10: 2～6.
The present invention recommends described ion-exchange to adopt following steps: after hydrolysis reaction finishes, with the hydrolysis reaction liquid cooling but, add S-WAT and do not generate to there being bubble, reaction solution concentrates, and regulating pH is 5～7, cross Amberlite IRA-400 anionite-exchange resin, use the distilled water wash-out, collect the elutriant that contains product, concentrate, recrystallization is drying to obtain L-carnitine.
Reaction formula is as follows:
Further, described L-(-)-halid negatively charged ion X of 3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) is preferably chlorine, bromine or iodine.
Further, the mass concentration of described aqueous hydrogen peroxide solution is 10～50%, and preferred mass concentration is 20～45%.
Further, described basic cpd is preferably salt of wormwood, yellow soda ash, sodium hydroxide or potassium hydroxide, more preferably sodium hydroxide or potassium hydroxide.
Further, in ion exchange reaction, the solvent that described recrystallization uses is selected from following a kind of or any two kinds mixed solution: ethanol, Virahol, acetone.
Comparatively concrete, recommend the synthetic method of L-carnitine of the present invention to carry out according to following steps: according to L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide: hydrogen peroxide: the ratio of the amount of substance of basic cpd is 1: 4～10: 2～6 to add L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide, mass concentration is 10～50% aqueous hydrogen peroxide solution and basic cpd, slowly be warmed up to 50～80 ℃ of reaction 0.5～2h, after reaction finishes, cooling, adding S-WAT does not generate to there being bubble, reaction solution concentrates, regulating pH is 5～7, cross Amberlite IRA-400 anionite-exchange resin, use the distilled water wash-out, collection contains the elutriant of product, concentrate, recrystallization is drying to obtain L-carnitine.
The present invention compared with prior art, its beneficial effect is embodied in:
The present invention obtains L-carnitine with hydrogen peroxide hydrolysis L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide under alkaline system, and hydrogen peroxide decomposition is water and oxygen in the reaction process, and is nontoxic, environmental protection.Technological reaction mild condition of the present invention, the reaction times is short, the reaction yield height, the three wastes are little, have bigger implementary value and economic results in society.
(4) embodiment:
Below with specific embodiment technical scheme of the present invention is described, but protection scope of the present invention is not limited thereto:
Embodiment 1
Feed intake amount of substance than L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) muriate: hydrogen peroxide: basic cpd is 1: 10: 2.
Thermometer is being housed, in reflux condensing tube and the churned mechanically 250mL there-necked flask, add L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) muriate 17.8g (100mmol), slowly add 30% hydrogen peroxide 120g (1000mmol) and sodium hydroxide 8g (200mmol), be warming up to 70 ℃ of reaction 1.5h, after reaction finishes, cooling, adding S-WAT does not generate to there being bubble, reaction solution concentrates, with about acid for adjusting pH=5, cross Amberlite IRA-400 resin anion(R.A) exchange column, use the distilled water wash-out, collect the elutriant that contains product, concentrate, use ethanol-acetone (volume ratio 2: 1) recrystallization to obtain L-carnitine 12.1g again, product yield 75.1%, 196～197 ℃ of mp, [α]
D 20-32 ° (c 10, H
2O).
Embodiment 2
Feed intake amount of substance than L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) muriate: hydrogen peroxide: basic cpd is 1: 10: 4.
Thermometer is being housed, in reflux condensing tube and the churned mechanically 250mL there-necked flask, add L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) muriate 17.8g (100mmol), slowly add 30% hydrogen peroxide 120g (1000mmol) and sodium hydroxide 16g (400mmol), be warming up to 70 ℃ of reaction 1.5h, after reaction finishes, cooling, adding S-WAT does not generate to there being bubble, reaction solution concentrates, with about acid for adjusting pH=5, cross Amberlite IRA-400 resin anion(R.A) exchange column, use the distilled water wash-out, collect the elutriant that contains product, concentrate, use ethanol-acetone (volume ratio 2: 1) recrystallization to obtain L-carnitine 12.8g again, product yield 79.5%, 196～197 ℃ of mp, [α]
D 20-31.7 ° (c 10, H
2O).
Embodiment 3
Feed intake amount of substance than L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) muriate: hydrogen peroxide: basic cpd is 1: 10: 6.
Thermometer is being housed, in reflux condensing tube and the churned mechanically 250mL there-necked flask, add L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) muriate 17.8g (100mmol), slowly add 40% hydrogen peroxide 90g (1000mmol) and potassium hydroxide 33.6g (600mmol), be warming up to 65 ℃ of reaction 1.0h, after reaction finishes, cooling, adding S-WAT does not generate to there being bubble, reaction solution concentrates, with about acid for adjusting pH=7, cross Amberlite IRA-400 resin anion(R.A) exchange column, use the distilled water wash-out, collect the elutriant that contains product, concentrate, use Virahol-acetone (volume ratio 2: 1) recrystallization to obtain L-carnitine 13.9g again, product yield 86.3%, 196～198 ℃ of mp, [α]
D 20-31.5 ° (c 10, H
2O).
Embodiment 4
Feed intake amount of substance than L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) muriate: hydrogen peroxide: basic cpd is 1: 8: 4.
Thermometer is being housed, in reflux condensing tube and the churned mechanically 250mL there-necked flask, add L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) muriate 17.8g (100mmol), slowly add 40% hydrogen peroxide 72g (800mmol) and potassium hydroxide 22.4g (400mmol), be warming up to 65 ℃ of reaction 2.0h, after reaction finishes, cooling, adding S-WAT does not generate to there being bubble, reaction solution concentrates, with about acid for adjusting pH=7, cross Amberlite IRA-400 resin anion(R.A) exchange column, use the distilled water wash-out, collect the elutriant that contains product, concentrate, use Virahol-acetone (volume ratio 2: 1) recrystallization to obtain L-carnitine 11.9g again, product yield 73.9%, 197～198 ℃ of mp, [α]
D 20-31.2 ° (c 10, H
2O).
Embodiment 5
Feed intake amount of substance than L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) muriate: hydrogen peroxide: basic cpd is 1: 8: 6.
Thermometer is being housed, in reflux condensing tube and the churned mechanically 250mL there-necked flask, add L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) muriate 17.8g (100mmol), slowly add 45% hydrogen peroxide 64g (800mmol) and sodium hydroxide 24g (600mmol), be warming up to 65 ℃ of reaction 1.5h, after reaction finishes, cooling, adding S-WAT does not generate to there being bubble, reaction solution concentrates, with about acid for adjusting pH=5, cross Amberlite IRA-400 resin anion(R.A) exchange column, use the distilled water wash-out, collect the elutriant that contains product, concentrate, use Virahol-acetone (volume ratio 2: 1) recrystallization to obtain L-carnitine 12.4g again, product yield 77%, 197～198 ℃ of mp, [α]
D 20-31.0 ° (c 10, H
2O).
Embodiment 6
Feed intake amount of substance than L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) muriate: hydrogen peroxide: basic cpd is 1: 8: 6.
Thermometer is being housed, in reflux condensing tube and the churned mechanically 250mL there-necked flask, add L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) muriate 17.8g (100mmol), slowly add 45% hydrogen peroxide 64g (800mmol) and sodium hydroxide 24g (600mmol), be warming up to 50 ℃ of reaction 2h, after reaction finishes, cooling, adding S-WAT does not generate to there being bubble, reaction solution concentrates, with about acid for adjusting pH=5, cross Amberlite IRA-400 resin anion(R.A) exchange column, use the distilled water wash-out, collect the elutriant that contains product, concentrate, use Virahol-acetone (volume ratio 2: 1) recrystallization to obtain L-carnitine 12.2g again, product yield 75.7%, 196～197 ℃ of mp, [α]
D 20-31.4 ° (c 10, H
2O).
Embodiment 7
Feed intake amount of substance than L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) bromide: hydrogen peroxide: basic cpd is 1: 4: 2.
Thermometer is being housed, in reflux condensing tube and the churned mechanically 250mL there-necked flask, add L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) bromide 22.3g (100mmol), slowly add 30% hydrogen peroxide 48.0g (400mmol) and sodium hydroxide 8g (200mmol), be warming up to 80 ℃ of reaction 2h, after reaction finishes, cooling, adding S-WAT does not generate to there being bubble, reaction solution concentrates, with about acid for adjusting pH=7, cross Amberlite IRA-400 resin anion(R.A) exchange column, use the distilled water wash-out, collect the elutriant that contains product, concentrate, use Virahol-acetone (volume ratio 2: 1) recrystallization to obtain L-carnitine 11.5g again, product yield 71.4%, 196～198 ℃ of mp, [α]
D 20-31.1 ° (c 10, H
2O).
Embodiment 8
Feed intake amount of substance than L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) iodide: hydrogen peroxide: basic cpd is 1: 4: 3.5.
Thermometer is being housed, in reflux condensing tube and the churned mechanically 250mL there-necked flask, add L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) iodide 26.9g (100mmol), slowly add 45% hydrogen peroxide 32g (400mmol) and sodium hydroxide 14g (350mmol), be warming up to 80 ℃ of reaction 1.5h, after reaction finishes, after reaction finishes, cooling, adding S-WAT does not generate to there being bubble, reaction solution concentrates, with about acid for adjusting pH=7, cross Amberlite IRA-400 resin anion(R.A) exchange column, use the distilled water wash-out, collection contains the elutriant of product, concentrate, use Virahol-acetone (volume ratio 2: 1) recrystallization to obtain L-carnitine 11.7g, product yield 72.6% again, 197～198 ℃ of mp, [α]
D 20-31.8 ° (c 10, H
2O).
Claims (8)
1. a structure is suc as formula the synthetic method of the L-carnitine shown in (I), be to be raw material with the L-(-) shown in the formula (II)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide, make through hydrolysis and ion-exchange, it is characterized in that described hydrolysis adopts following method: in alkaline aqueous solution, with hydrogen peroxide hydrolysis L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide, fully obtain hydrolysis reaction liquid after the reaction;
2. the synthetic method of L-carnitine as claimed in claim 1, it is characterized in that described hydrolysis reaction step is as follows: in reaction vessel, add L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide, aqueous hydrogen peroxide solution and basic cpd, be warmed up to 50～80 ℃ of reaction 0.5～2h, reaction obtains hydrolysis reaction liquid after finishing; Described L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide: hydrogen peroxide: the ratio of the amount of substance that feeds intake of basic cpd is 1: 4～10: 2～6.
3. the synthetic method of L-carnitine as claimed in claim 1, it is characterized in that described ion-exchange employing following steps: after hydrolysis reaction finishes, with the hydrolysis reaction liquid cooling but, add S-WAT and generate to there being bubble, reaction solution concentrates, regulating pH is 5～7, crosses Amberlite IRA-400 anionite-exchange resin, uses the distilled water wash-out, collection contains the elutriant of product, concentrate, recrystallization is drying to obtain L-carnitine.
4. as the synthetic method of the described L-carnitine of one of claim 1～3, it is characterized in that described L-(-)-halid negatively charged ion X of 3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) is chlorine, bromine or iodine.
5. the synthetic method of L-carnitine as claimed in claim 2 is characterized in that described basic cpd is salt of wormwood, yellow soda ash, sodium hydroxide or potassium hydroxide.
6. the synthetic method of L-carnitine as claimed in claim 2, the mass concentration that it is characterized in that described aqueous hydrogen peroxide solution is 10～50%.
7. the synthetic method of L-carnitine as claimed in claim 3 is characterized in that the solvent that described recrystallization uses is following a kind of or any two kinds mixed solution: ethanol, Virahol, acetone.
8. the synthetic method of L-carnitine as claimed in claim 1, it is characterized in that described synthetic method carries out according to following steps: according to L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide: hydrogen peroxide: the ratio of the amount of substance of basic cpd is 1: 4～10: 2～6 to add L-(-)-3-cyano-2-hydroxy-propyl group TMA (TriMethylAmine) halogenide, mass concentration is 10～50% aqueous hydrogen peroxide solution and basic cpd, slowly be warmed up to 50～80 ℃ of reaction 0.5～2h, after reaction finishes, cooling, adding S-WAT does not generate to there being bubble, reaction solution concentrates, regulating pH is 5～7, cross Amberlite IRA-400 anionite-exchange resin, use the distilled water wash-out, collection contains the elutriant of product, concentrate, recrystallization is drying to obtain L-carnitine.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351722A (en) * | 2011-08-10 | 2012-02-15 | 江西新先锋医药有限公司 | L-carnitine compound and composite thereof |
| CN105481709A (en) * | 2015-08-19 | 2016-04-13 | 广西壮族自治区化工研究院 | Method for purifying and desalting crude product of L-carnitine |
| CN111233686A (en) * | 2019-12-24 | 2020-06-05 | 常州寅盛药业有限公司 | Method for recrystallizing levocarnitine |
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| WO1999062864A1 (en) * | 1998-05-29 | 1999-12-09 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Chemical process for the stereoselective synthesis of r-(-)-carnitine |
| JP2008133198A (en) * | 2006-11-27 | 2008-06-12 | Mitsubishi Rayon Co Ltd | Method for producing l-carnitine |
| CN101823974A (en) * | 2010-05-20 | 2010-09-08 | 北京科技大学 | Preparation method by adopting (R)-(-)-glycerinchlorohydrin as chirality starting material to synthetize L-carnitine |
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2010
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| WO1999062864A1 (en) * | 1998-05-29 | 1999-12-09 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Chemical process for the stereoselective synthesis of r-(-)-carnitine |
| JP2008133198A (en) * | 2006-11-27 | 2008-06-12 | Mitsubishi Rayon Co Ltd | Method for producing l-carnitine |
| CN101823974A (en) * | 2010-05-20 | 2010-09-08 | 北京科技大学 | Preparation method by adopting (R)-(-)-glycerinchlorohydrin as chirality starting material to synthetize L-carnitine |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351722A (en) * | 2011-08-10 | 2012-02-15 | 江西新先锋医药有限公司 | L-carnitine compound and composite thereof |
| CN102351722B (en) * | 2011-08-10 | 2012-08-29 | 江西新先锋医药有限公司 | L-carnitine compound and composite thereof |
| CN105481709A (en) * | 2015-08-19 | 2016-04-13 | 广西壮族自治区化工研究院 | Method for purifying and desalting crude product of L-carnitine |
| CN111233686A (en) * | 2019-12-24 | 2020-06-05 | 常州寅盛药业有限公司 | Method for recrystallizing levocarnitine |
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