SE430330B - Metod att framstella monokalium-l-malat-monohydrat - Google Patents

Metod att framstella monokalium-l-malat-monohydrat

Info

Publication number: SE430330B
Authority: SE; Sweden
Prior art keywords: malate; malic acid; crystals; potassium; solution
Prior art date: 1977-02-18

Application number

SE7801856A

Other languages

English (en)

Swedish (sv)

Other versions

SE7801856L (sv

Inventor

I Chibata

A Sumi

O Ohtsuki

Original Assignee

Tanabe Seiyaku Co

Priority date (The priority date 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 date listed.)

1977-02-18

Filing date

1978-02-17

Publication date

1983-11-07

1978-02-17 Application filed by Tanabe Seiyaku Co filed Critical Tanabe Seiyaku Co

1978-08-19 Publication of SE7801856L publication Critical patent/SE7801856L/xx

1983-11-07 Publication of SE430330B publication Critical patent/SE430330B/sv

Links

238000000034 method Methods 0.000 title claims description 18
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 162
239000013078 crystal Substances 0.000 claims description 92
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 83
229940116298 l- malic acid Drugs 0.000 claims description 76
235000011090 malic acid Nutrition 0.000 claims description 76
239000000243 solution Substances 0.000 claims description 67
239000000203 mixture Substances 0.000 claims description 64
KDZFDRFJUFSZHE-JIZZDEOASA-M potassium (2S)-2,4-dihydroxy-4-oxobutanoate hydrate Chemical compound O.[K+].O[C@@H](CC(O)=O)C([O-])=O KDZFDRFJUFSZHE-JIZZDEOASA-M 0.000 claims description 31
SVICABYXKQIXBM-JIZZDEOASA-L dipotassium;(2s)-2-hydroxybutanedioate Chemical compound [K+].[K+].[O-]C(=O)[C@@H](O)CC([O-])=O SVICABYXKQIXBM-JIZZDEOASA-L 0.000 claims description 27
239000007864 aqueous solution Substances 0.000 claims description 22
238000002425 crystallisation Methods 0.000 claims description 19
230000008025 crystallization Effects 0.000 claims description 19
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 15
229910001414 potassium ion Inorganic materials 0.000 claims description 15
239000007790 solid phase Substances 0.000 claims description 14
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 6
239000000284 extract Substances 0.000 claims 1
229910001868 water Inorganic materials 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
JZRVQGVITBCZDB-DKWTVANSSA-M potassium (3S)-3,4-dihydroxy-4-oxobutanoate Chemical compound C([C@@H](O)CC(=O)O)(=O)[O-].[K+] JZRVQGVITBCZDB-DKWTVANSSA-M 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 21
239000011591 potassium Substances 0.000 description 20
229910052700 potassium Inorganic materials 0.000 description 20
238000001914 filtration Methods 0.000 description 16
239000002244 precipitate Substances 0.000 description 16
238000003756 stirring Methods 0.000 description 16
229910000027 potassium carbonate Inorganic materials 0.000 description 12
235000011181 potassium carbonates Nutrition 0.000 description 12
239000000047 product Substances 0.000 description 11
238000001816 cooling Methods 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000007791 liquid phase Substances 0.000 description 7
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000003125 aqueous solvent Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 4
150000004682 monohydrates Chemical class 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000011736 potassium bicarbonate Substances 0.000 description 4
235000015497 potassium bicarbonate Nutrition 0.000 description 4
229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
JZRVQGVITBCZDB-UHFFFAOYSA-M potassium;3,4-dihydroxy-4-oxobutanoate Chemical compound [K+].[O-]C(=O)C(O)CC(O)=O JZRVQGVITBCZDB-UHFFFAOYSA-M 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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 3
239000001530 fumaric acid Substances 0.000 description 3
239000012535 impurity Substances 0.000 description 3
150000004701 malic acid derivatives Chemical class 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
238000011084 recovery Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
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 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000003957 anion exchange resin Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000001175 calcium sulphate Substances 0.000 description 2
235000011132 calcium sulphate Nutrition 0.000 description 2
239000003729 cation exchange resin Substances 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
229940099690 malic acid Drugs 0.000 description 2
239000001630 malic acid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
159000000001 potassium salts Chemical class 0.000 description 2
KDZFDRFJUFSZHE-UHFFFAOYSA-M potassium;2,4-dihydroxy-4-oxobutanoate;hydrate Chemical compound O.[K+].[O-]C(=O)C(O)CC(O)=O KDZFDRFJUFSZHE-UHFFFAOYSA-M 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
DOJOZCIMYABYPO-DKWTVANSSA-M sodium;(3s)-3,4-dihydroxy-4-oxobutanoate Chemical compound [Na+].OC(=O)[C@@H](O)CC([O-])=O DOJOZCIMYABYPO-DKWTVANSSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241001262617 Japonica Species 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
HOHYOBOXBKCIHM-UHFFFAOYSA-L dipotassium;2-hydroxybutanedioate;hydrate Chemical compound O.[K+].[K+].[O-]C(=O)C(O)CC([O-])=O HOHYOBOXBKCIHM-UHFFFAOYSA-L 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940049920 malate Drugs 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
ASVDLBFHXKXPER-SQGDDOFFSA-M sodium (2S)-2,4-dihydroxy-4-oxobutanoate dihydrate Chemical compound O.O.[Na+].O[C@@H](CC(O)=O)C([O-])=O ASVDLBFHXKXPER-SQGDDOFFSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
230000003068 static effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SE7801856A 1977-02-18 1978-02-17 Metod att framstella monokalium-l-malat-monohydrat SE430330B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP1751177A JPS53103416A (en)	1977-02-18	1977-02-18	Preparation of l-malic acid

Publications (2)

Publication Number	Publication Date
SE7801856L SE7801856L (sv)	1978-08-19
SE430330B true SE430330B (sv)	1983-11-07

Family

ID=11945985

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7801856A SE430330B (sv)	1977-02-18	1978-02-17	Metod att framstella monokalium-l-malat-monohydrat

Country Status (7)

Country	Link
US (1)	US4124636A (de)
JP (1)	JPS53103416A (de)
CH (1)	CH635059A5 (de)
DE (1)	DE2806679A1 (de)
FR (1)	FR2381018A1 (de)
GB (1)	GB1574265A (de)
SE (1)	SE430330B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6018692U (ja) *	1983-07-14	1985-02-08	三洋電機株式会社	モ−タ回路
CN114436812B (zh) *	2021-12-27	2024-07-16	河南瑞贝佳生物科技有限公司	一种苹果酸二钾的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DD45077A (de) *
FR1466109A (fr) *	1965-01-29	1967-01-13	Allied Chem	Malates monohydratés de métaux alcalins et leur procédé de fabrication par cristallisation à partir d'une solution aqueuse
US3435070A (en) *	1965-01-29	1969-03-25	Allied Chem	Alkali metal-d,l-malate monohydrates
JPS523019A (en) *	1975-06-24	1977-01-11	Kawasaki Kasei Chem Ltd	Preparation of alkali metal malate hydrate
US4057577A (en) *	1976-08-05	1977-11-08	Chevron Research Company	Process for preparing di(alkoxy-carboxy) hydrocarbylenes

1977
- 1977-02-18 JP JP1751177A patent/JPS53103416A/ja active Granted
1978
- 1978-02-10 US US05/876,698 patent/US4124636A/en not_active Expired - Lifetime
- 1978-02-16 DE DE19782806679 patent/DE2806679A1/de not_active Withdrawn
- 1978-02-17 GB GB6505/78A patent/GB1574265A/en not_active Expired
- 1978-02-17 FR FR7804617A patent/FR2381018A1/fr active Granted
- 1978-02-17 SE SE7801856A patent/SE430330B/sv not_active IP Right Cessation
- 1978-02-17 CH CH178278A patent/CH635059A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB1574265A (en)	1980-09-03
JPS5532694B2 (de)	1980-08-26
FR2381018A1 (fr)	1978-09-15
US4124636A (en)	1978-11-07
DE2806679A1 (de)	1978-08-31
SE7801856L (sv)	1978-08-19
FR2381018B1 (de)	1983-04-08
CH635059A5 (de)	1983-03-15
JPS53103416A (en)	1978-09-08

Legal Events

Date

Code

Title

Description

1995-01-31

NUG

Patent has lapsed

Ref document number: 7801856-1

Effective date: 19890425

Format of ref document f/p: F

Publication	Publication Date	Title
DK162518B (da)	1991-11-11	Fremgangsmaade til fremstilling af en stabil modifikation af torasemid, samt et farmaceutisk praeparat indeholdende denne
CA2033871A1 (en)	1991-07-11	Formation and resolution of dexibuprofen lysine
KR100532898B1 (ko)	2005-12-05	플루다라빈 포스페이트의 제조를 위한 정제 방법
JPH07506813A (ja)	1995-07-27	ホリニン酸の立体異性体を分離する方法
US4399304A (en)	1983-08-16	L-phenylalanine 1/2 sulfate and its use
EP0582351A1 (de)	1994-02-09	Verfahren zur Kristallisierung von Aspartam
EP3856732B1 (de)	2023-09-13	Verfahren und salze zur herstellung von 2,5-furandicarbonsäure
US4124636A (en)	1978-11-07	Method of preparing monopotassium L-malate and its monohydrate
DK2502626T3 (en)	2015-08-17	Crystalline levofolinsyre and method for preparation thereof
US3557081A (en)	1971-01-19	Alkali metal salts of guanosine
HU205768B (en)	1992-06-29	Process for purifying amphotericin b
SU925251A3 (ru)	1982-04-30	Способ получени кристаллической формы D-конфигурации полуторной натриевой соли 7 @ -/ @ -карбокси- @ -(п-оксифенил) ацетамидо/-7 @ -метокси-3-(1-метилтетразол-5-ил)-тиометил-1-оксадетиа-3-цефем-4-карбоновой кислоты
CA1072578A (en)	1980-02-26	Ethercarboxylate monohydrate useful as a detergency builder
US2331948A (en)	1943-10-19	Method for the purification of lactic acid
US4115439A (en)	1978-09-19	Process for the preparation of optically active α-phenylglycine and intermediates thereof
US2309739A (en)	1943-01-26	Z-aminopykimtoines
US2764612A (en)	1956-09-25	Process for preparing salts of glutamic acid
US2857375A (en)	1958-10-21	Streptomycin and dihydrostreptomycin salts and method of recovering and purifying streptomycin and dihydrostrep tomycin by means thereof
US3147269A (en)	1964-09-01	Process for the separation of nicotinic and isonicotinic acid
US4263454A (en)	1981-04-21	Lithium ribonate, lithium arabonate and the preparation and purification of these salts
CA2572831A1 (en)	2006-01-26	Improved process for the manufacture of mirtazapine
US617985A (en)	1899-01-17	Emil fischer
US3374223A (en)	1968-03-19	Crystalline sodium 5'-guanylate pentahydrate and method of producing the same
SU1386571A1 (ru)	1988-04-07	Способ получени пентафторвисмутатов ( @ ) щелочных металлов
Gibson et al.	1915	LXXXIV.—Resolution of externally compensated p-toluenesulphonylalanine into its optically active components