JPS6330456A - Production of dl-carnitine - Google Patents
Production of dl-carnitineInfo
- Publication number
- JPS6330456A JPS6330456A JP17540486A JP17540486A JPS6330456A JP S6330456 A JPS6330456 A JP S6330456A JP 17540486 A JP17540486 A JP 17540486A JP 17540486 A JP17540486 A JP 17540486A JP S6330456 A JPS6330456 A JP S6330456A
- Authority
- JP
- Japan
- Prior art keywords
- carnitine
- solvent
- basic substance
- basic
- water
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229960004203 carnitine Drugs 0.000 title 1
- 239000000126 substance Substances 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 9
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 9
- PHIQHXFUZVPYII-LURJTMIESA-N (S)-carnitine Chemical compound C[N+](C)(C)C[C@@H](O)CC([O-])=O PHIQHXFUZVPYII-LURJTMIESA-N 0.000 claims abstract description 8
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 3
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 claims description 7
- 239000003125 aqueous solvent Substances 0.000 claims description 4
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- -1 NaOH Chemical class 0.000 abstract description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 2
- GUYHPGUANSLONG-SNAWJCMRSA-N (E)-4-(trimethylammonio)but-2-enoate Chemical compound C[N+](C)(C)C\C=C\C([O-])=O GUYHPGUANSLONG-SNAWJCMRSA-N 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 230000002503 metabolic effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- QQZIUHOKWDFXEY-UHFFFAOYSA-N tribromo(nitro)methane Chemical group [O-][N+](=O)C(Br)(Br)Br QQZIUHOKWDFXEY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- JXXCENBLGFBQJM-RGMNGODLSA-N (3s)-3-hydroxy-4-(trimethylazaniumyl)butanoate;hydrochloride Chemical compound [Cl-].C[N+](C)(C)C[C@@H](O)CC(O)=O JXXCENBLGFBQJM-RGMNGODLSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- VZAWCLCJGSBATP-UHFFFAOYSA-N 1-cycloundecyl-1,2-diazacycloundecane Chemical compound C1CCCCCCCCCC1N1NCCCCCCCCC1 VZAWCLCJGSBATP-UHFFFAOYSA-N 0.000 description 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 230000004129 fatty acid metabolism Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- OPUAWDUYWRUIIL-UHFFFAOYSA-L methanedisulfonate Chemical compound [O-]S(=O)(=O)CS([O-])(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-L 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】 産業上の利用分野 本発明はＤＬ−カルニチンの製造法に関する。[Detailed description of the invention] Industrial applications The present invention relates to a method for producing DL-carnitine.
ＤＬ−カルニチンは脂肪酸代謝促進剤、輸液用成分とし
ての用途が期待されるし一力ルニチンの製造原料として
有用である。DL-carnitine is expected to be used as a fatty acid metabolism promoter and a component for infusion, and is useful as a raw material for producing lunitine.
従来の技術
ＤＬ−カルニチン又はその前駆体であるニトリルやアミ
ドを光学分割することにより最終的にＬ−カル；チンを
得ることができる（特開昭５５−１３２９９、特公昭４
０−３８９１．特公昭４７−６３２９１＞。この際結果
として副生ずるＤ−カルニチンのラセミ化法については
特開昭５５−１３２９９号に、Ｄ−カルニチンアミド塩
酸塩を、濃塩酸中、１００℃、６０時間という過酷な条
件下で、ＤＬ−カルニチン塩酸塩に変換する方法が示さ
れているのみである。しかしながらこの方法はＤ−カル
ニチンアミドに誘導しなければならないこと、過酷な反
応条件を必要とすること、及び高価な耐酸性の装萱を必
要とすることから、工業的製法としては適さないと考え
られる。Conventional technology L-carnitine can finally be obtained by optically resolving DL-carnitine or its precursors such as nitriles and amides (Japanese Unexamined Patent Publication No. 55-13299, Japanese Patent Publication No. Sho 4)
0-3891. Special Publication No. 47-63291>. Regarding the racemization method of D-carnitine which is produced as a by-product in this process, it is described in JP-A-55-13299 that D-carnitinamide hydrochloride is DL-carnitine hydrochloride in concentrated hydrochloric acid at 100°C for 60 hours. Only a method for converting to carnitine hydrochloride is shown. However, this method is considered unsuitable as an industrial production method because it must be induced into D-carnitinamide, requires harsh reaction conditions, and requires expensive acid-resistant equipment. It will be done.
又、Ｄ−カルニチンもしくはそのハロゲン化水素酸塩を
酸性条件下に脱水剤（例えば酢酸−無水酢酸等）で脱水
することによりクロトノペタインに変換する方法が知ら
れており〔例えばＢ １ｏｃｈ ｉｍ １ｃａｅｔ Ｂ
ｉｏｐｈｙｓｉｃａ Ａｃｔａ １３７．９８（１９６
７） ； Ａｒｃｈ Ｂ＋ｏｃｈｅｍＢｉｏｐｈｓ０．
３８ 、 ４０５（１９５２） 〕、一方クりトノ
ベタインを酵素的に水和してＬ−カルニチンに導く方法
も知られている（特開昭５９−１８３６９４゜５９−１
９２０９５．６０−１３７２９５．６０−２２４４８８
）。Furthermore, a method is known in which D-carnitine or its hydrohalide is dehydrated with a dehydrating agent (e.g., acetic acid-acetic anhydride) under acidic conditions to convert it into crotonopetaine [e.g.
iophysica Acta 137.98 (196
7); Arch B+ochemBiophs0.
38, 405 (1952)], on the other hand, a method for enzymatically hydrating critonobetaine to lead to L-carnitine is also known (Japanese Patent Application Laid-Open No. 59-183694゜59-1).
92095.60-137295.60-224488
).
発明が解決しようとする問題点
工業的に実施可能？ａ、Ｄ−カルニチンのラセミ化法が
求められている。Is the problem that the invention seeks to solve industrially possible? There is a need for a racemization method for a, D-carnitine.
問題点を解決するための手段
本発明によればＤＬ−カルニチンはクロトノペタインも
しくはＤ−カルニチン又はこれらの酸付加塩を水系溶媒
中塩基性物質の存在下保持することにより製造すること
ができる。Means for Solving the Problems According to the present invention, DL-carnitine can be produced by maintaining crotonopetaine or D-carnitine or an acid addition salt thereof in an aqueous solvent in the presence of a basic substance.
酸付加塩はハロゲン化水素酸塩（例えば塩酸塩、臭化水
素酸塩）、硫酸塩、硝酸塩、リン酸塩、過塩素酸塩等の
無機酸塩；トリフルオロ酢酸塩、ギ酸塩、マレイン酸塩
、フマール酸塩、コハク酸塩、酒石酸塩、クエン酸塩、
蓚酸塩、メタンスルホン酸塩、エタンスルホン酸塩、プ
ロパンスルホン酸塩、メタンジスルホン酸塩、α、β−
エタンジスルホン酸塩、ベンゼンスルホン酸塩等の有機
酸塩を包含する。Acid addition salts include inorganic acid salts such as hydrohalides (e.g. hydrochlorides, hydrobromides), sulfates, nitrates, phosphates, perchlorates; trifluoroacetates, formates, maleates. salt, fumarate, succinate, tartrate, citrate,
Oxalate, methanesulfonate, ethanesulfonate, propanesulfonate, methanedisulfonate, α, β-
Includes organic acid salts such as ethanedisulfonate and benzenesulfonate.
塩基性物質はＮａ０ＨＳＫＯＨのようなアルカリ金属水
酸化物、Ｎａ２ＣＯ３、Ｋ２ＣＯ，のようなアルカリ金
属炭酸塩、ＮａＨＣＯｓ、ＫＨＣＯ。Basic substances include alkali metal hydroxides such as Na0HSKOH, alkali metal carbonates such as Na2CO3, K2CO, NaHCOs, and KHCO.
のようなアルカリ金属重炭酸塩、Ｃａ（ＯＨ）２、Ｂａ
（ＯＨ）ｚのようなアルカリ土類金属水酸化物、ジアザ
ビシクロウンデカン（ＢＢＵ） 、ジアザビシクロオク
タンのような３級アミン、テトラブチルアンモニウムヒ
ドロキシド、トリメチルベンジルアンモニウムヒドロキ
シドのような第４級アンモニウムヒドロキシド、塩基性
イオン交換樹脂〔例えばダイヤイオンＰＡンリーズ（Ｐ
Ａ−４０８，４１２，４１６等）、アンバーライトＩＲ
Ａシリーズ（ＩＲＡ−４０２，４１０，４０１等）等の
イオン交換樹脂〕等を包含する。塩基性物質の反応液中
での濃度は１−７０％、特に３５−６０％（Ｗ／Ｖ）が
好ましい。水系溶媒は水、含水のメタノール、エタノー
ル、イソプロパツール等の炭素数１〜４の低級アルカノ
ール等を包含するが、特に水が好ましい。Alkali metal bicarbonates such as Ca(OH)2, Ba
Alkaline earth metal hydroxides such as (OH)z, tertiary amines such as diazabicycloundecane (BBU), diazabicyclooctane, quaternary hydroxides such as tetrabutylammonium hydroxide, trimethylbenzylammonium hydroxide class ammonium hydroxide, basic ion exchange resin [e.g. Diaion PA Anries (P
A-408, 412, 416 etc.), Amberlight IR
ion exchange resins such as A series (IRA-402, 410, 401, etc.)]. The concentration of the basic substance in the reaction solution is preferably 1-70%, particularly 35-60% (W/V). The aqueous solvent includes water, lower alkanols having 1 to 4 carbon atoms such as water-containing methanol, ethanol, and isopropanol, and water is particularly preferred.
反応は０℃〜溶媒の沸点以下の温度、水を溶媒として用
いた場合は好ましくは５０〜８０℃で行い、通常１〜１
０時間で終了する。The reaction is carried out at a temperature of 0°C to the boiling point of the solvent, preferably 50 to 80°C when water is used as a solvent, and usually 1 to 1
It ends in 0 hours.
反応液からＤＬ−カルニチンの単離は既知の一般精製手
段が適用でき、例えば不溶物を濾過等により除去した後
、弱酸性イオン交換樹脂（例えばダイヤイオンＷＫ−１
１）に通塔して過剰の塩基性物質を吸着除去し、ついで
強酸性イオン交換樹脂（例えばダイヤイオンＰＫ−２１
６）に通塔してＤＬ−カルニチンを吸着させ、アンモニ
ア水で溶出した液を濃縮することによって行われる。Known general purification means can be applied to isolate DL-carnitine from the reaction solution. For example, after removing insoluble matter by filtration, etc., use a weakly acidic ion exchange resin (for example, Diaion WK-1).
1) to adsorb and remove excess basic substances, and then use a strongly acidic ion exchange resin (for example, Diaion PK-21) to adsorb and remove excess basic substances.
6) to adsorb DL-carnitine, and concentrate the solution eluted with aqueous ammonia.
実施例 次に実施例によって本発明を具体的に説明する。Example Next, the present invention will be specifically explained with reference to Examples.
実施例１
クロトノペタイン７、９６ ｇを、５０％（ｗ／ｖ）Ｎ
ａＯＨ水溶液３０ Ｑｍｌに溶解し、７０℃で１５時間
反応させた。反応液を、弱酸性イオン交換樹脂（Ｈ”型
、ダイヤイオンＷＫ−１１）に通液し、−流出液を、強
酸性イオン交換樹脂（Ｈ＋型、ダイヤイオンＰＫ−２１
６）に通液した。３Ｎ−ＮＨ３水溶液２．８００ｍ１で
溶出してきた液を、減圧下に濃縮し、３Ｎ−ＨＣｊ！水
溶液１． ｏｏｏｍｔを加えた後、減圧濃縮し、アセト
ン４．０００ｆｆｌｌを加えて結晶化してＤＬ−カルニ
チン塩酸塩９．３４ ｇを得た。Example 1 Crotonopetaine 7.96 g was added to 50% (w/v) N
It was dissolved in 30 Qml of aOH aqueous solution and reacted at 70°C for 15 hours. The reaction solution was passed through a weakly acidic ion exchange resin (H” type, Diaion WK-11), and the effluent was passed through a strong acidic ion exchange resin (H+ type, Diaion PK-21).
6). The liquid eluted with 2.800 ml of 3N-NH3 aqueous solution was concentrated under reduced pressure, and 3N-HCj! Aqueous solution 1. After adding ooomt, the mixture was concentrated under reduced pressure and crystallized by adding 4.000 ffll of acetone to obtain 9.34 g of DL-carnitine hydrochloride.
収率８５％。Yield 85%.
実施例２
クロトノペタイン３．９８ ｇを、強塩基性イオン交換
樹脂ダイヤイオンＦＡ−２１９（ＯＨ−型）１００ｇを
含む水２０ Ｑｍｌに溶解し、６０℃で２０時間反応さ
せた。反応液を濾過した液に、３ Ｎ−ＨＣｊ！ １０
０１１１１を加え、減圧下に濃縮し、アセトン２．００
０ｍ１を加えて結晶化し、ＤＬ−カルニチン塩酸塩３．
０７ ｇを得た。収率７０％。Example 2 3.98 g of crotonopetaine was dissolved in 20 Qml of water containing 100 g of strongly basic ion exchange resin Diaion FA-219 (OH-type), and reacted at 60°C for 20 hours. The reaction solution was filtered, and 3N-HCj! 10
Add 01111, concentrate under reduced pressure, and add 2.00% of acetone.
Add 0 ml of DL-carnitine hydrochloride to crystallize 3.
07 g was obtained. Yield 70%.
実施例３
Ｄ−カルニチン塩酸塩〔α’Ｊ ｏ ＋２４．０°（ｃ
＝３、Ｈ２Ｏ） ） １．００ ｇを、１０％（Ｗ／Ｖ
）ＮａＯＨ水溶液１５ｍｌに溶解し、１２０℃で９時間
反応後、ＮａＯＨ４，Ｏｇを加え、７０℃で１０時間反
応させた。以下実施例１と同様な操作によりＤＬ−カル
ニチン塩酸塩０．９０ ｇを得た。Example 3 D-carnitine hydrochloride [α'J o +24.0° (c
=3, H2O) ) 1.00 g, 10% (W/V
) It was dissolved in 15 ml of NaOH aqueous solution and reacted at 120°C for 9 hours, then NaOH4,Og was added and reacted at 70°C for 10 hours. Thereafter, 0.90 g of DL-carnitine hydrochloride was obtained by the same operation as in Example 1.
収率９０％。〔α〕Ｉ、０°（Ｃ＝３、Ｈ２Ｏ）。Yield 90%. [α]I, 0° (C=3, H2O).
発明の効果
り一力ルニチン等の製造原料として有用なりＬ−カルニ
チンをＤ−カルニチンもしくはクロトノペタインより工
業的に有利に実施し得る方法が提供される。As a result of the invention, a method is provided in which L-carnitine is useful as a raw material for producing lunitine and the like, and is industrially more advantageous than D-carnitine or crotonopetaine.
Claims (3)
れらの酸付加塩を水系溶媒中塩基性物質の存在下保持す
ることを特徴とするＤＬ−カルニチンの製造法。(1) A method for producing DL-carnitine, which comprises maintaining crotonopetaine or D-carnitine or an acid addition salt thereof in an aqueous solvent in the presence of a basic substance.
類金属水酸化物、アルカリ金属の炭酸塩もしくは重炭酸
塩、３級アミン、第４級アンモニウムヒドロキシド又は
塩基性イオン交換樹脂である特許請求の範囲第１項記載
の製造法。(2) Patent where the basic substance is an alkali metal hydroxide, alkaline earth metal hydroxide, alkali metal carbonate or bicarbonate, tertiary amine, quaternary ammonium hydroxide, or basic ion exchange resin The manufacturing method according to claim 1.
許請求の範囲第１項もしくは２項記載の製造法。(3) The production method according to claim 1 or 2, wherein the aqueous solvent is water or a water-containing lower alkanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17540486A JPS6330456A (en) | 1986-07-25 | 1986-07-25 | Production of dl-carnitine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17540486A JPS6330456A (en) | 1986-07-25 | 1986-07-25 | Production of dl-carnitine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6330456A true JPS6330456A (en) | 1988-02-09 |
Family
ID=15995500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17540486A Pending JPS6330456A (en) | 1986-07-25 | 1986-07-25 | Production of dl-carnitine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6330456A (en) |
-
1986
- 1986-07-25 JP JP17540486A patent/JPS6330456A/en active Pending
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