JPS6141332B2 - - Google Patents
Info
- Publication number
- JPS6141332B2 JPS6141332B2 JP7000778A JP7000778A JPS6141332B2 JP S6141332 B2 JPS6141332 B2 JP S6141332B2 JP 7000778 A JP7000778 A JP 7000778A JP 7000778 A JP7000778 A JP 7000778A JP S6141332 B2 JPS6141332 B2 JP S6141332B2
- Authority
- JP
- Japan
- Prior art keywords
- malic acid
- crystals
- solution
- crystal
- monopotassium salt
- 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
Links
- 239000013078 crystal Substances 0.000 claims description 96
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 51
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 31
- 235000011090 malic acid Nutrition 0.000 claims description 26
- 229940116298 l- malic acid Drugs 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 238000001556 precipitation Methods 0.000 claims description 21
- 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 19
- 229910001414 potassium ion Inorganic materials 0.000 claims description 14
- 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 claims description 13
- 238000000926 separation method Methods 0.000 claims description 11
- 239000003125 aqueous solvent Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 4
- 150000004682 monohydrates Chemical class 0.000 claims description 4
- 239000000243 solution Substances 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 238000002425 crystallisation Methods 0.000 description 16
- 230000008025 crystallization Effects 0.000 description 15
- 239000000126 substance Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- -1 DL-malic acid alkali metal salt Chemical class 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 229960003975 potassium Drugs 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229940099690 malic acid Drugs 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- JZRVQGVITBCZDB-UHFFFAOYSA-M potassium;3,4-dihydroxy-4-oxobutanoate Chemical class [K+].[O-]C(=O)C(O)CC(O)=O JZRVQGVITBCZDB-UHFFFAOYSA-M 0.000 description 2
- 208000019025 Hypokalemia Diseases 0.000 description 1
- 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 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 208000024896 potassium deficiency disease Diseases 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229940070017 potassium supplement Drugs 0.000 description 1
- 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 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940083542 sodium Drugs 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000004448 titration Methods 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
- 238000012546 transfer Methods 0.000 description 1
- 238000004457 water analysis Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7000778A JPS54163520A (en) | 1978-06-09 | 1978-06-09 | Production of crystal of monopotassium l-malate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7000778A JPS54163520A (en) | 1978-06-09 | 1978-06-09 | Production of crystal of monopotassium l-malate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54163520A JPS54163520A (en) | 1979-12-26 |
| JPS6141332B2 true JPS6141332B2 (fr) | 1986-09-13 |
Family
ID=13419107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7000778A Granted JPS54163520A (en) | 1978-06-09 | 1978-06-09 | Production of crystal of monopotassium l-malate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54163520A (fr) |
-
1978
- 1978-06-09 JP JP7000778A patent/JPS54163520A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54163520A (en) | 1979-12-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8153842B2 (en) | Method for producing 3-(2,2,2-trimethyl-hydrazinium) propionate dihydrate | |
| SU668608A3 (ru) | Способ получени -кристаллической формы натриевой соли 7-( -2-формилокси-2-фенилацетамидо)-3-(1-метил-1н-тетразолил-5-тиометил)-3-цефем-4-карбоновой кислоты | |
| JPS6141332B2 (fr) | ||
| JPS6155901B2 (fr) | ||
| US3381031A (en) | Resolution of racemic amino acids | |
| US3848063A (en) | Process for the manufacture of high-purity lithium hexafluoroarsenate | |
| US4076745A (en) | Process for calcium salts α-ketocarboxylic acids | |
| US4014929A (en) | Ether carboxylate monohydrate | |
| KR100343232B1 (ko) | 결정성 파미드론산 이나트륨염 수화물과 그의 제조방법 | |
| SU657750A3 (ru) | Способ получени кристаллической модификации натриевой соли 7 цианацетиламино-3-ацетоксиметил3-цефем-4-карбоновой кислоты | |
| JP2004315332A (ja) | 無機ヨウ素化合物の製造方法 | |
| US4124636A (en) | Method of preparing monopotassium L-malate and its monohydrate | |
| CA1144558A (fr) | Methode d'obtention de divalproate acide de sodium | |
| JPS5944302B2 (ja) | スレオニンとアロスレオニンとの相互分離方法 | |
| US3471506A (en) | Process for preparing 5-chloro-2,3-pyridine diol | |
| CN113968841B (zh) | 一种盐酸法舒地尔半水合物的制备方法 | |
| US2764612A (en) | Process for preparing salts of glutamic acid | |
| US2711423A (en) | Neutral calcium 4-aminosalicylate hemihydrate and preparation of the same | |
| KR20040016837A (ko) | 3 ―（3 ―아미디노페닐）―5 ―〔（｛〔1 ―（1―이미노에틸）―4 ―피페리딜}아미노）메틸〕벤조산디히드로클로라이드 및 그의 제조 방법 | |
| JPH08134088A (ja) | Ｎ−ホスホノメチルグリシンの単離方法 | |
| JP3316917B2 (ja) | 新規フェニルアラニン塩結晶とその製造法 | |
| US2668852A (en) | Neutral calcium 4-aminosalicylate hemihydrate and preparation of the same | |
| JP4817737B2 (ja) | Ｌ−アスパラギン酸カルシウム結晶の製造方法 | |
| JPS6372691A (ja) | 経口投与用セフアロスポリン水和物結晶 | |
| JP2001002689A (ja) | 結晶質ｌ−アスコルビン酸−２−リン酸エステルナトリウム塩およびその製造方法 |