CA1297497C - Process for the production of gamma-butyrobetaine - Google Patents
Process for the production of gamma-butyrobetaineInfo
- Publication number
- CA1297497C CA1297497C CA000610959A CA610959A CA1297497C CA 1297497 C CA1297497 C CA 1297497C CA 000610959 A CA000610959 A CA 000610959A CA 610959 A CA610959 A CA 610959A CA 1297497 C CA1297497 C CA 1297497C
- Authority
- CA
- Canada
- Prior art keywords
- gamma
- butyrobetaine
- chlorobutyric acid
- butyrolactone
- bars
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- JHPNVNIEXXLNTR-UHFFFAOYSA-O 4-(trimethylammonio)butanoic acid Chemical compound C[N+](C)(C)CCCC(O)=O JHPNVNIEXXLNTR-UHFFFAOYSA-O 0.000 title claims abstract 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims abstract description 26
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 10
- -1 chlorobutyric acid ester Chemical class 0.000 claims abstract description 7
- IMKUQCXMPMOQOI-UHFFFAOYSA-N butanoic acid;n,n-dimethylmethanamine Chemical compound C[NH+](C)C.CCCC([O-])=O IMKUQCXMPMOQOI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- IPLKGJHGWCVSOG-UHFFFAOYSA-N 4-chlorobutanoic acid Chemical compound OC(=O)CCCCl IPLKGJHGWCVSOG-UHFFFAOYSA-N 0.000 claims description 11
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 4
- 229930188620 butyrolactone Natural products 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- JHPNVNIEXXLNTR-UHFFFAOYSA-N 4-(trimethylammonio)butanoate Chemical compound C[N+](C)(C)CCCC([O-])=O JHPNVNIEXXLNTR-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 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 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229960004203 carnitine Drugs 0.000 description 2
- 238000000909 electrodialysis Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 241000448280 Elates Species 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 239000012531 culture fluid Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- BHQQXAOBIZQEGI-UHFFFAOYSA-N methyl 2-chlorobutanoate Chemical compound CCC(Cl)C(=O)OC BHQQXAOBIZQEGI-UHFFFAOYSA-N 0.000 description 1
- 238000013048 microbiological method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Picture Signal Circuits (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compounds Of Unknown Constitution (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Transforming Electric Information Into Light Information (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3514/88 | 1988-09-21 | ||
| CH351488 | 1988-09-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1297497C true CA1297497C (en) | 1992-03-17 |
Family
ID=4257629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000610959A Expired - Lifetime CA1297497C (en) | 1988-09-21 | 1989-09-11 | Process for the production of gamma-butyrobetaine |
Country Status (17)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1261231B (it) * | 1993-04-08 | 1996-05-09 | Sigma Tau Ind Farmaceuti | Procedimento migliorato per la preparazione di l-(-)-carnitina a partire da un prodotto di scarto avente opposta configurazione. |
| IT1261230B (it) * | 1993-04-08 | 1996-05-09 | Sigma Tau Ind Farmaceuti | Procedimento migliorato per la preparazione di l-(-)-carnitina a partire da suoi precursori aventi opposta configurazione. |
| DE19634640A1 (de) * | 1996-08-27 | 1998-03-05 | Basf Ag | Verfahren zur Reinigung von Lösungen, die Betain enthalten, durch Elektrodialyse und mittels eines Kationenaustauschermoduls |
| DK1370663T3 (da) * | 2001-01-31 | 2007-07-02 | Lonza Ag | Mikrobiologisk metode til fremstilling af L-carnitin |
| PL2069290T3 (pl) * | 2006-09-04 | 2014-04-30 | Akciju Sabiedriba Olainfarm | Sposób wytwarzania 3-(2,2,2-trimetylohydrazyno)propionianu w postaci dihydratu |
| LV14345B (lv) * | 2009-10-22 | 2011-07-20 | Grindeks, A/S | 4-[Etil(dimetil)amonija]butanoāts un tā izmantošana kardiovaskulāro slimību ārstēšanai |
| RU2720985C1 (ru) * | 2019-07-04 | 2020-05-15 | Федеральное государственное унитарное предприятие "Научно-исследовательский институт гигиены, профпатологии и экологии человека" Федерального медико-биологического агентства | Способ получения гамма-бутиробетаина и его гидрохлорида |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2313573A (en) * | 1938-01-17 | 1943-03-09 | Gen Aniline & Film Corp | Capillary active compounds and process of preparing them |
| US2367878A (en) * | 1939-05-04 | 1945-01-23 | Hoffmann La Roche | Betaine esters |
| NL6511804A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1964-11-30 | 1966-05-31 | ||
| FR1559839A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-01-30 | 1969-03-14 | ||
| ES370147A1 (es) * | 1968-08-29 | 1971-04-01 | Gulf Research Development Co | Un procedimiento para fabricar ciclopropilamina. |
| US3711549A (en) * | 1970-05-19 | 1973-01-16 | Gulf Research Development Co | Process for manufacturing cyclopropylamine |
| US3796632A (en) * | 1971-12-10 | 1974-03-12 | Toray Industries | Process for racemizing alpha-amino-epsilon-caprolactam |
| BE795170A (fr) * | 1972-02-09 | 1973-08-08 | Procter & Gamble | Procede pour l'obtention de derives tensioactifs de betaine |
| JPS5136732A (ja) * | 1974-09-25 | 1976-03-27 | Katsutoshi Okamoto | Konkuriitodasetsuyotenjomenkariwakunotoritsuke torihazushisochi |
| JPS538684A (en) * | 1976-07-12 | 1978-01-26 | Nippon Foil Mfg | Heat adhesive alminium foil |
| DE2751134C2 (de) * | 1977-11-16 | 1986-04-17 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von γ-Chlorcarbonsäureestern |
| IT1142201B (it) * | 1980-06-24 | 1986-10-08 | Sigma Tau Ind Farmaceuti | Procedimento per la produzione enzimatica di l-carnitina |
| DE3214953A1 (de) * | 1982-04-22 | 1983-10-27 | Hoechst Ag, 6230 Frankfurt | Mikrobielle polysaccharide, verfahren zu ihrer herstellung, dafuer geeignete mikroorganismen und verwendung der polysaccharide |
| JPS59192095A (ja) * | 1983-04-13 | 1984-10-31 | Ajinomoto Co Inc | Ｌ−カルニチンの製造法 |
| JPS6165850A (ja) * | 1984-09-08 | 1986-04-04 | Junichi Iwamura | ベタイン類誘導体及びその製造方法並びにコリンエステラ−ゼ基質 |
| CH664374A5 (de) * | 1985-02-27 | 1988-02-29 | Lonza Ag | Verfahren zur herstellung von l-carnitin auf mikrobiologischem weg. |
| IT1190280B (it) * | 1986-04-24 | 1988-02-16 | Sigma Tau Ind Farmaceuti | Procedimento per la preparazione di gamma-butirrobetaina |
-
1989
- 1989-07-05 JP JP1173896A patent/JPH0291049A/ja active Granted
- 1989-08-18 FI FI893900A patent/FI94751C/fi active IP Right Grant
- 1989-09-11 CA CA000610959A patent/CA1297497C/en not_active Expired - Lifetime
- 1989-09-11 IL IL91607A patent/IL91607A0/xx not_active IP Right Cessation
- 1989-09-15 MX MX017568A patent/MX170034B/es unknown
- 1989-09-18 DD DD89332759A patent/DD284220A5/de not_active IP Right Cessation
- 1989-09-19 ES ES89117307T patent/ES2053899T3/es not_active Expired - Lifetime
- 1989-09-19 AT AT89117307T patent/ATE86605T1/de not_active IP Right Cessation
- 1989-09-19 RU SU894614913A patent/RU1836333C/ru active
- 1989-09-19 EP EP89117307A patent/EP0360222B1/de not_active Expired - Lifetime
- 1989-09-19 DE DE8989117307T patent/DE58903714D1/de not_active Expired - Lifetime
- 1989-09-20 SK SK5384-89A patent/SK538489A3/sk unknown
- 1989-09-20 CZ CS895384A patent/CZ278975B6/cs not_active IP Right Cessation
- 1989-09-20 PT PT91757A patent/PT91757B/pt not_active IP Right Cessation
- 1989-09-20 DK DK198904638A patent/DK175100B1/da not_active IP Right Cessation
- 1989-09-20 NO NO893740A patent/NO173603C/no not_active IP Right Cessation
-
1991
- 1991-03-12 US US07/667,367 patent/US5087745A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE58903714D1 (de) | 1993-04-15 |
| JPH0466859B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-10-26 |
| CZ538489A3 (en) | 1994-04-13 |
| DK463889A (da) | 1990-03-22 |
| EP0360222A1 (de) | 1990-03-28 |
| DK463889D0 (da) | 1989-09-20 |
| EP0360222B1 (de) | 1993-03-10 |
| MX170034B (es) | 1993-08-04 |
| ATE86605T1 (de) | 1993-03-15 |
| IL91607A0 (en) | 1990-04-29 |
| SK280453B6 (sk) | 2000-02-14 |
| DD284220A5 (de) | 1990-11-07 |
| FI893900A0 (fi) | 1989-08-18 |
| NO893740D0 (no) | 1989-09-20 |
| NO173603C (no) | 1994-01-05 |
| NO893740L (no) | 1990-03-22 |
| RU1836333C (ru) | 1993-08-23 |
| PT91757B (pt) | 1995-05-31 |
| FI94751B (fi) | 1995-07-14 |
| PT91757A (pt) | 1990-03-30 |
| FI893900L (fi) | 1990-03-22 |
| ES2053899T3 (es) | 1994-08-01 |
| SK538489A3 (en) | 2000-02-14 |
| JPH0291049A (ja) | 1990-03-30 |
| US5087745A (en) | 1992-02-11 |
| DK175100B1 (da) | 2004-06-01 |
| NO173603B (no) | 1993-09-27 |
| FI94751C (fi) | 1995-10-25 |
| CZ278975B6 (en) | 1994-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |