JPH0134213B2 - - Google Patents
Info
- Publication number
- JPH0134213B2 JPH0134213B2 JP56040219A JP4021981A JPH0134213B2 JP H0134213 B2 JPH0134213 B2 JP H0134213B2 JP 56040219 A JP56040219 A JP 56040219A JP 4021981 A JP4021981 A JP 4021981A JP H0134213 B2 JPH0134213 B2 JP H0134213B2
- Authority
- JP
- Japan
- Prior art keywords
- malic acid
- crystals
- monoammonium
- salt
- optically active
- 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 40
- 230000003287 optical effect Effects 0.000 claims description 17
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 16
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 15
- RMIOHTPMSWCRSO-UHFFFAOYSA-N azane;2-hydroxybutanedioic acid Chemical compound N.OC(=O)C(O)CC(O)=O RMIOHTPMSWCRSO-UHFFFAOYSA-N 0.000 claims description 15
- RMIOHTPMSWCRSO-DKWTVANSSA-N azane;(2s)-2-hydroxybutanedioic acid Chemical compound [NH4+].[O-]C(=O)[C@@H](O)CC(O)=O RMIOHTPMSWCRSO-DKWTVANSSA-N 0.000 claims description 12
- 229940099690 malic acid Drugs 0.000 claims description 11
- 239000001630 malic acid Substances 0.000 claims description 11
- 235000011090 malic acid Nutrition 0.000 claims description 11
- BJEPYKJPYRNKOW-UWTATZPHSA-N (R)-malic acid Chemical compound OC(=O)[C@H](O)CC(O)=O BJEPYKJPYRNKOW-UWTATZPHSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- RMIOHTPMSWCRSO-HSHFZTNMSA-N azane (2R)-2-hydroxybutanedioic acid Chemical compound N.OC(=O)[C@H](O)CC(O)=O RMIOHTPMSWCRSO-HSHFZTNMSA-N 0.000 claims description 7
- 239000012452 mother liquor Substances 0.000 claims description 7
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 3
- 229940116298 l- malic acid Drugs 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 108010036781 Fumarate Hydratase Proteins 0.000 description 2
- 102100036160 Fumarate hydratase, mitochondrial Human genes 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 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 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000010170 biological method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization 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 |
|---|---|---|---|
| JP4021981A JPS57156433A (en) | 1981-03-19 | 1981-03-19 | Preparation of optical active malic acid or its salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4021981A JPS57156433A (en) | 1981-03-19 | 1981-03-19 | Preparation of optical active malic acid or its salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57156433A JPS57156433A (en) | 1982-09-27 |
| JPH0134213B2 true JPH0134213B2 (zh) | 1989-07-18 |
Family
ID=12574651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4021981A Granted JPS57156433A (en) | 1981-03-19 | 1981-03-19 | Preparation of optical active malic acid or its salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57156433A (zh) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4927841A (zh) * | 1972-07-08 | 1974-03-12 |
-
1981
- 1981-03-19 JP JP4021981A patent/JPS57156433A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4927841A (zh) * | 1972-07-08 | 1974-03-12 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57156433A (en) | 1982-09-27 |
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