FI94751C - Menetelmä -butyrobetaiinin valmistamiseksi - Google Patents
Menetelmä -butyrobetaiinin valmistamiseksi Download PDFInfo
- Publication number
- FI94751C FI94751C FI893900A FI893900A FI94751C FI 94751 C FI94751 C FI 94751C FI 893900 A FI893900 A FI 893900A FI 893900 A FI893900 A FI 893900A FI 94751 C FI94751 C FI 94751C
- Authority
- FI
- Finland
- Prior art keywords
- kpa
- butyrolactone
- butyrobetaine
- pressure
- temperature
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 17
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 13
- JHPNVNIEXXLNTR-UHFFFAOYSA-O 4-(trimethylammonio)butanoic acid Chemical compound C[N+](C)(C)CCCC(O)=O JHPNVNIEXXLNTR-UHFFFAOYSA-O 0.000 claims abstract 2
- IMKUQCXMPMOQOI-UHFFFAOYSA-N butanoic acid;n,n-dimethylmethanamine Chemical compound C[NH+](C)C.CCCC([O-])=O IMKUQCXMPMOQOI-UHFFFAOYSA-N 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims 3
- IPLKGJHGWCVSOG-UHFFFAOYSA-N 4-chlorobutanoic acid Chemical compound OC(=O)CCCCl IPLKGJHGWCVSOG-UHFFFAOYSA-N 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 229930188620 butyrolactone Natural products 0.000 abstract description 6
- -1 chlorobutyric acid ester Chemical class 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- JHPNVNIEXXLNTR-UHFFFAOYSA-N 4-(trimethylammonio)butanoate Chemical compound C[N+](C)(C)CCCC([O-])=O JHPNVNIEXXLNTR-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- OPXNFHAILOHHFO-UHFFFAOYSA-N ethyl 4-chlorobutanoate Chemical compound CCOC(=O)CCCCl OPXNFHAILOHHFO-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- ZZUYIRISBMWFMV-UHFFFAOYSA-N methyl 4-chlorobutanoate Chemical compound COC(=O)CCCCl ZZUYIRISBMWFMV-UHFFFAOYSA-N 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000000909 electrodialysis Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 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
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229960004203 carnitine Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- QAWFLJGZSZIZHO-UHFFFAOYSA-N methyl 4-bromobutanoate Chemical compound COC(=O)CCCBr QAWFLJGZSZIZHO-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium 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
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000010626 work up procedure Methods 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 |
|---|---|---|---|
| CH351488 | 1988-09-21 | ||
| CH351488 | 1988-09-21 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI893900A0 FI893900A0 (fi) | 1989-08-18 |
| FI893900L FI893900L (fi) | 1990-03-22 |
| FI94751B FI94751B (fi) | 1995-07-14 |
| FI94751C true FI94751C (fi) | 1995-10-25 |
Family
ID=4257629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI893900A FI94751C (fi) | 1988-09-21 | 1989-08-18 | Menetelmä -butyrobetaiinin valmistamiseksi |
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 |
| CA1297497C (en) | 1992-03-17 |
| JPH0291049A (ja) | 1990-03-30 |
| US5087745A (en) | 1992-02-11 |
| DK175100B1 (da) | 2004-06-01 |
| NO173603B (no) | 1993-09-27 |
| CZ278975B6 (en) | 1994-11-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH1017554A (ja) | Ｎ−アルキル−ｎ′−メチルイミダゾリニウム有機酸塩の製造方法 | |
| EP2231587B1 (en) | Process for the preparation of betaines | |
| JPH10218836A (ja) | マロン酸およびアルキルマロン酸の製造方法 | |
| FI94751C (fi) | Menetelmä -butyrobetaiinin valmistamiseksi | |
| US4002666A (en) | Process for the preparation of optically active p-hydroxyphenylglycine | |
| TW503233B (en) | Process for the preparation of hydroxy methylthiobutyric acid esters | |
| US4977264A (en) | Process for the production of 4,5-dichloro-6-ethylpyrimidine | |
| EP2247572A1 (en) | A one-pot process for preparing 3-(2,2,2-trimethylhydrazinium)propionate dihydrate | |
| CN101914052A (zh) | 一种奥拉西坦化合物及其新方法 | |
| CN105820101B (zh) | 一种旋光纯1-(氨基甲酰基)甲基-4-羟基-2-吡咯烷酮的制备方法 | |
| US8445715B2 (en) | Method of synthesizing fenofibrate | |
| CN116655484B (zh) | 一种l-4-氯-2-氨基丁酸酯类盐酸盐的制备方法 | |
| CN108440349B (zh) | 一种手性光学纯对甲苯亚磺酰胺的制备方法 | |
| CN109867679B (zh) | 盐酸吡西卡尼中间体的制备方法 | |
| US2790000A (en) | L-glutamine synthesis | |
| CN111116430B (zh) | 一种牛磺酸钠的制备方法 | |
| CA2336919A1 (en) | A process for the preparation of 4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oic acid | |
| Jack | A NEW SYNTHESIS FOR 1‐AMINOHYDANTOIN AND NITROFURANTOIN | |
| CN108358803B (zh) | 一种氘代甘氨酸、马尿酸-l-薄荷酯（2,2-d2）及其中间体的合成方法 | |
| CN112552172A (zh) | 一种基于低共熔溶剂催化剂合成肉桂酸甲酯的方法 | |
| CA2535655A1 (en) | Process for production of o-substituted hydroxylamines | |
| CA1142957A (en) | PROCESS FOR PREPARING .alpha.-ARYL PROPIONIC ACIDS | |
| SU536168A1 (ru) | Способ получени -алкил- -аланинов или их солей по аминогруппе | |
| HU186528B (en) | Process for producing tetronnoic acid | |
| US2783274A (en) | Method of making serine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| FG | Patent granted |
Owner name: LONZA AG |