JP2003525923A - 水溶液からの有機酸の回収方法 - Google Patents
水溶液からの有機酸の回収方法Info
- Publication number
- JP2003525923A JP2003525923A JP2001565329A JP2001565329A JP2003525923A JP 2003525923 A JP2003525923 A JP 2003525923A JP 2001565329 A JP2001565329 A JP 2001565329A JP 2001565329 A JP2001565329 A JP 2001565329A JP 2003525923 A JP2003525923 A JP 2003525923A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- mother liquor
- klg
- grams
- organic acid
- 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.)
- Withdrawn
Links
- 150000007524 organic acids Chemical class 0.000 title claims abstract description 160
- 238000000034 method Methods 0.000 title claims abstract description 145
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 44
- VBUYCZFBVCCYFD-NUNKFHFFSA-N 2-dehydro-L-idonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-NUNKFHFFSA-N 0.000 claims abstract description 317
- VBUYCZFBVCCYFD-UHFFFAOYSA-N D-arabino-2-Hexulosonic acid Natural products OCC(O)C(O)C(O)C(=O)C(O)=O VBUYCZFBVCCYFD-UHFFFAOYSA-N 0.000 claims abstract description 316
- 239000002253 acid Substances 0.000 claims abstract description 132
- 239000000203 mixture Substances 0.000 claims abstract description 118
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 91
- 150000001450 anions Chemical class 0.000 claims abstract description 63
- 239000000243 solution Substances 0.000 claims abstract description 52
- 235000010323 ascorbic acid Nutrition 0.000 claims abstract description 45
- 239000011668 ascorbic acid Substances 0.000 claims abstract description 45
- 229960005070 ascorbic acid Drugs 0.000 claims abstract description 45
- 238000000855 fermentation Methods 0.000 claims abstract description 17
- 230000004151 fermentation Effects 0.000 claims abstract description 17
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 12
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims abstract description 10
- 239000008346 aqueous phase Substances 0.000 claims abstract description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims abstract description 8
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims abstract description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000004310 lactic acid Substances 0.000 claims abstract description 7
- 235000014655 lactic acid Nutrition 0.000 claims abstract description 7
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims abstract description 6
- RGHNJXZEOKUKBD-QTBDOELSSA-N L-gulonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-QTBDOELSSA-N 0.000 claims abstract description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229950006191 gluconic acid Drugs 0.000 claims abstract description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 6
- 239000011976 maleic acid Substances 0.000 claims abstract description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 6
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims abstract description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims abstract description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 235000011054 acetic acid Nutrition 0.000 claims abstract description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims abstract description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims abstract description 4
- 235000015165 citric acid Nutrition 0.000 claims abstract description 4
- 235000019253 formic acid Nutrition 0.000 claims abstract description 4
- 239000000174 gluconic acid Substances 0.000 claims abstract description 4
- 235000012208 gluconic acid Nutrition 0.000 claims abstract description 4
- 239000001630 malic acid Substances 0.000 claims abstract description 4
- 235000011090 malic acid Nutrition 0.000 claims abstract description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229940107700 pyruvic acid Drugs 0.000 claims abstract description 4
- 239000011975 tartaric acid Substances 0.000 claims abstract description 4
- 235000002906 tartaric acid Nutrition 0.000 claims abstract description 4
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound 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 claims abstract description 3
- 229960001367 tartaric acid Drugs 0.000 claims abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 132
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 87
- 239000011734 sodium Substances 0.000 claims description 60
- 229910052708 sodium Inorganic materials 0.000 claims description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- 229910052700 potassium Inorganic materials 0.000 claims description 38
- 239000011777 magnesium Substances 0.000 claims description 36
- 229910052749 magnesium Inorganic materials 0.000 claims description 36
- 239000003729 cation exchange resin Substances 0.000 claims description 30
- 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 claims description 29
- 150000003839 salts Chemical group 0.000 claims description 26
- 238000001914 filtration Methods 0.000 claims description 24
- 239000002585 base Substances 0.000 claims description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 238000004448 titration Methods 0.000 claims description 15
- 239000003957 anion exchange resin Substances 0.000 claims description 14
- 239000011575 calcium Substances 0.000 claims description 12
- 238000000354 decomposition reaction Methods 0.000 claims description 11
- 229910052791 calcium Inorganic materials 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 10
- -1 organic acid salt Chemical class 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000004064 recycling Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical group [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims description 5
- 229910001626 barium chloride Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 235000021317 phosphate Nutrition 0.000 claims description 4
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 230000003750 conditioning effect Effects 0.000 claims description 3
- 235000000346 sugar Nutrition 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 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 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 238000010908 decantation Methods 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 150000002823 nitrates Chemical class 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 238000001694 spray drying Methods 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- VBUYCZFBVCCYFD-JJYYJPOSSA-N 2-dehydro-D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-JJYYJPOSSA-N 0.000 claims 3
- 239000000010 aprotic solvent Substances 0.000 claims 2
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- MPCRDALPQLDDFX-UHFFFAOYSA-L Magnesium perchlorate Chemical compound [Mg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O MPCRDALPQLDDFX-UHFFFAOYSA-L 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 229910052788 barium Inorganic materials 0.000 claims 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical group [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 1
- NKQIMNKPSDEDMO-UHFFFAOYSA-L barium bromide Chemical compound [Br-].[Br-].[Ba+2] NKQIMNKPSDEDMO-UHFFFAOYSA-L 0.000 claims 1
- 229910001620 barium bromide Inorganic materials 0.000 claims 1
- OOULUYZFLXDWDQ-UHFFFAOYSA-L barium perchlorate Chemical compound [Ba+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O OOULUYZFLXDWDQ-UHFFFAOYSA-L 0.000 claims 1
- 235000010350 erythorbic acid Nutrition 0.000 claims 1
- 239000004318 erythorbic acid Substances 0.000 claims 1
- 229960004275 glycolic acid Drugs 0.000 claims 1
- 229940026239 isoascorbic acid Drugs 0.000 claims 1
- 159000000008 strontium salts Chemical class 0.000 claims 1
- 238000011084 recovery Methods 0.000 abstract description 117
- 229940093915 gynecological organic acid Drugs 0.000 abstract description 27
- 235000005985 organic acids Nutrition 0.000 abstract description 27
- 239000012452 mother liquor Substances 0.000 description 338
- 235000010633 broth Nutrition 0.000 description 189
- 238000002425 crystallisation Methods 0.000 description 153
- 230000008025 crystallization Effects 0.000 description 153
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
- 239000000047 product Substances 0.000 description 85
- 239000000706 filtrate Substances 0.000 description 72
- 229910052698 phosphorus Inorganic materials 0.000 description 70
- 238000001035 drying Methods 0.000 description 69
- 238000003828 vacuum filtration Methods 0.000 description 69
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 45
- 229910052799 carbon Inorganic materials 0.000 description 45
- 229910052500 inorganic mineral Inorganic materials 0.000 description 43
- 235000010755 mineral Nutrition 0.000 description 43
- 239000011707 mineral Substances 0.000 description 43
- 238000005341 cation exchange Methods 0.000 description 35
- 230000020477 pH reduction Effects 0.000 description 35
- 230000005588 protonation Effects 0.000 description 35
- 238000005406 washing Methods 0.000 description 33
- 239000000460 chlorine Substances 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- 230000015556 catabolic process Effects 0.000 description 23
- 238000006731 degradation reaction Methods 0.000 description 23
- 238000001471 micro-filtration Methods 0.000 description 23
- 229910052801 chlorine Inorganic materials 0.000 description 22
- 150000001768 cations Chemical class 0.000 description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
- 238000005349 anion exchange Methods 0.000 description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- 239000011574 phosphorus Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 13
- 229910052717 sulfur Inorganic materials 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 10
- 239000012535 impurity Substances 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- 150000007942 carboxylates Chemical class 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000004364 calculation method Methods 0.000 description 6
- 238000005342 ion exchange Methods 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 150000001767 cationic compounds Chemical class 0.000 description 5
- 238000010494 dissociation reaction Methods 0.000 description 5
- 230000005593 dissociations Effects 0.000 description 5
- 229910001411 inorganic cation Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 241000894007 species Species 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000013626 chemical specie Substances 0.000 description 3
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- 150000002500 ions Chemical class 0.000 description 3
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- 150000002894 organic compounds Chemical class 0.000 description 3
- XWSGEVNYFYKXCP-UHFFFAOYSA-N 2-[carboxymethyl(methyl)amino]acetic acid Chemical compound OC(=O)CN(C)CC(O)=O XWSGEVNYFYKXCP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 2
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001449 anionic compounds Chemical class 0.000 description 2
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- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 229910001412 inorganic anion Inorganic materials 0.000 description 2
- 150000003893 lactate salts Chemical class 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 150000002791 naphthoquinones Chemical class 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- 101710192523 30S ribosomal protein S9 Proteins 0.000 description 1
- XSDMYDIROCZZIK-UHFFFAOYSA-N 6-[[4-(5-carboxypentylcarbamoyl)benzoyl]amino]hexanoic acid Chemical compound OC(=O)CCCCCNC(=O)C1=CC=C(C(=O)NCCCCCC(O)=O)C=C1 XSDMYDIROCZZIK-UHFFFAOYSA-N 0.000 description 1
- 235000008496 Drimys aromatica Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- DGABKXLVXPYZII-UHFFFAOYSA-N Hyodeoxycholic acid Natural products C1C(O)C2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 DGABKXLVXPYZII-UHFFFAOYSA-N 0.000 description 1
- 108020004511 Recombinant DNA Proteins 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 240000008202 Schinus molle Species 0.000 description 1
- 235000005151 Schinus molle Nutrition 0.000 description 1
- 235000013880 Schinus terebinthifolius var. raddianus Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000010564 aerobic fermentation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- DGABKXLVXPYZII-SIBKNCMHSA-N hyodeoxycholic acid Chemical compound C([C@H]1[C@@H](O)C2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 DGABKXLVXPYZII-SIBKNCMHSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910001504 inorganic chloride Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HGJLYMGBCAKBLK-UHFFFAOYSA-N sodium;trifluoromethanesulfonic acid Chemical compound [Na].OS(=O)(=O)C(F)(F)F HGJLYMGBCAKBLK-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/803—Physical recovery methods, e.g. chromatography, grinding
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/874—Pseudomonas
- Y10S435/876—Pseudomonas fluorescens
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces
- Y10S435/896—Streptomyces fradiae
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/519,936 | 2000-03-07 | ||
| US09/519,936 US6670505B1 (en) | 2000-03-07 | 2000-03-07 | Process for the recovery of organic acids from aqueous solutions |
| PCT/US2001/007140 WO2001066508A2 (en) | 2000-03-07 | 2001-03-06 | Process for the recovery of organic acids from aqueous solutions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003525923A true JP2003525923A (ja) | 2003-09-02 |
| JP2003525923A5 JP2003525923A5 (enExample) | 2008-04-24 |
Family
ID=24070463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001565329A Withdrawn JP2003525923A (ja) | 2000-03-07 | 2001-03-06 | 水溶液からの有機酸の回収方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6670505B1 (enExample) |
| EP (1) | EP1261574B1 (enExample) |
| JP (1) | JP2003525923A (enExample) |
| CN (1) | CN100413839C (enExample) |
| AT (1) | ATE344225T1 (enExample) |
| BR (1) | BR0109005A (enExample) |
| DE (1) | DE60124229T2 (enExample) |
| WO (1) | WO2001066508A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005030973A1 (ja) * | 2003-09-30 | 2007-11-15 | 味の素株式会社 | 発酵液からのコハク酸の精製方法 |
| JP2022514350A (ja) * | 2018-12-19 | 2022-02-10 | ビーエーエスエフ ソシエタス・ヨーロピア | バイオマス及び少なくとも１種のオリゴ糖を含む溶液からバイオマスを分離する方法 |
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| DE10007702A1 (de) | 2000-02-19 | 2001-08-23 | Sueddeutsche Kalkstickstoff | Verfahren zur Herstellung von N-(Phosphonomethyl)glycin |
| AU6293001A (en) | 2000-05-22 | 2001-12-11 | Monsanto Technology Llc | Reaction systems for making n-(phosphonomethyl)glycine compounds |
| US20060149084A1 (en) * | 2002-12-19 | 2006-07-06 | Thomas Domschke | Method for extracting 2-ketone-l-gulonic acid from a polar, preferably aqueous solvent |
| DE10308045B3 (de) * | 2003-02-26 | 2004-06-17 | Lurgi Ag | Verfahren und Vorrichtung zur kontinuierlichen Gewinnung freier Weinsäure aus Kaliumhydrogentartrat enthaltenden Rohstoffen |
| JP4469568B2 (ja) | 2003-07-09 | 2010-05-26 | 三菱化学株式会社 | 有機酸の製造方法 |
| BRPI0413403A (pt) | 2003-08-28 | 2006-10-17 | Mitsubishi Chem Corp | método para produzir ácido succìnico |
| WO2005026349A1 (ja) | 2003-09-17 | 2005-03-24 | Mitsubishi Chemical Corporation | 非アミノ有機酸の製造方法 |
| CN1989238B (zh) | 2004-05-20 | 2010-05-26 | 味之素株式会社 | 生产琥珀酸的细菌和生产琥珀酸的方法 |
| CN100389075C (zh) * | 2004-08-10 | 2008-05-21 | 株式会社神钢环境舒立净 | 排水处理方法和排水处理装置 |
| AU2005292735A1 (en) * | 2004-10-01 | 2006-04-13 | Ge Healthcare As | Method for producing pyruvic acid |
| BRPI0617491B1 (pt) | 2005-10-18 | 2021-04-27 | Ajinomoto Co., Inc | Processo para produção de ácido succínico |
| BRPI0707674A2 (pt) | 2006-02-24 | 2011-05-10 | Mitsubishi Chem Corp | bactÉria capaz de produzir Ácido orgÂnico e processo para produÇço do mesmo |
| CN101906032A (zh) * | 2010-07-14 | 2010-12-08 | 华东理工大学 | 回收和循环使用l-(+)-酒石酸的方法 |
| US9376364B2 (en) * | 2011-08-16 | 2016-06-28 | Purac Biochem B.V. | Acid/salt separation |
| MY179474A (en) * | 2011-08-16 | 2020-11-07 | Purac Biochem Bv | Recovery of carboxylic acid from their magnesium salts by precipitation using hydrochloric acid, useful for fermentation broth work-up |
| US9061986B2 (en) * | 2011-08-16 | 2015-06-23 | Purac Biochem B.V. | Acid/salt separation |
| EP2744747B1 (en) | 2011-08-16 | 2020-11-18 | Purac Biochem B.V. | Recovery of carboxylic acid from their magnesium salts by precipitation using hydrochloric acid, useful for fermentation broth work-up |
| US9480574B2 (en) | 2013-03-14 | 2016-11-01 | Benvenue Medical, Inc. | Spinal fusion implants and devices and methods for deploying such implants |
| CN103450007B (zh) * | 2013-09-02 | 2015-06-17 | 西安通鑫半导体辅料有限公司 | 一种从硅片脱胶工序产生的废乳酸中回收乳酸的方法 |
| US9422398B2 (en) | 2014-05-30 | 2016-08-23 | Industrial Technology Research Institute | Copolymer, and method for preparing a monomer used to form the copolymer |
| US10314605B2 (en) | 2014-07-08 | 2019-06-11 | Benvenue Medical, Inc. | Apparatus and methods for disrupting intervertebral disc tissue |
| CN104447529B (zh) * | 2014-11-25 | 2017-05-24 | 利尔化学股份有限公司 | 3,6‑二氯吡啶甲酸的提取纯化方法 |
| CN104672078B (zh) * | 2015-02-02 | 2017-05-24 | 江苏索普（集团）有限公司 | 一种羰基合成醋酸副产物提纯制丙酸的工艺 |
| US10022243B2 (en) | 2015-02-06 | 2018-07-17 | Benvenue Medical, Inc. | Graft material injector system and method |
| US10758286B2 (en) | 2017-03-22 | 2020-09-01 | Benvenue Medical, Inc. | Minimal impact access system to disc space |
| WO2019148083A1 (en) | 2018-01-29 | 2019-08-01 | Benvenue Medical, Inc. | Minimally invasive interbody fusion |
| WO2019178575A1 (en) | 2018-03-16 | 2019-09-19 | Benvenue Medical, Inc. | Articulated instrumentation and methods of using the same |
| CN108314164B (zh) * | 2018-03-27 | 2020-06-19 | 浙江大学 | 回收废水中钡的方法 |
| CN108947066A (zh) * | 2018-07-13 | 2018-12-07 | 宁波永顺精细化工有限公司 | 羧酸钡废水中羧酸及钡盐的回收方法 |
| KR102520535B1 (ko) * | 2018-12-24 | 2023-04-11 | 안형일 | 미네랄을 포함하는 사료 첨가 조성물 |
| CN111943836A (zh) * | 2019-05-16 | 2020-11-17 | 帝斯曼知识产权资产管理有限公司 | 回收2-酮-l-古洛糖酸的改进方法 |
| CN111978202B (zh) * | 2020-08-12 | 2022-08-05 | 浙江理工大学上虞工业技术研究院有限公司 | 可碱洗分散染料水解产物的回收方法 |
| CN112552164B (zh) * | 2020-12-08 | 2022-12-09 | 日照金禾博源生化有限公司 | 一种从不合格柠檬酸钠母液中提取苹果酸的工艺方法 |
| US20240391861A1 (en) * | 2021-10-29 | 2024-11-28 | Alliance For Sustainable Energy, Llc | Process for the recovery of monopotassium glucarate and glucaric acid |
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| US2318500A (en) * | 1935-10-21 | 1943-05-04 | Parke Davis & Co | Preparation of ascorbic acid and 1-gulosone |
| US2421612A (en) | 1945-05-04 | 1947-06-03 | Byron E Gray | Preparation of 2-keto gulonic acid and its salts |
| US2421611A (en) * | 1945-05-04 | 1947-06-03 | Byron E Gray | Preparation of 2-keto gulonic acid and its salts |
| US2462251A (en) | 1945-05-16 | 1949-02-22 | Merck & Co Inc | Process for preparing ascorbic acids |
| US2918492A (en) * | 1956-08-24 | 1959-12-22 | Miles Lab | Method of preparing methyl 2-ketogluconate |
| US3043749A (en) * | 1960-07-28 | 1962-07-10 | Pfizer & Co C | Preparation of 2-keto-l-gulonic acid |
| US3234105A (en) * | 1962-09-20 | 1966-02-08 | Takeda Chemical Industries Ltd | Method for producing 2-keto-lgulonic acid |
| US3381027A (en) * | 1964-04-22 | 1968-04-30 | Hoffmann La Roche | Preparation and recovery of methyl 2-ketogluconate |
| US4113771A (en) | 1971-04-07 | 1978-09-12 | Ethyl Corporation | Process for the purification of citric acid |
| US4202828A (en) | 1978-01-10 | 1980-05-13 | Kawasaki Kasei Chemicals Limited | Process for separation of naphthoquinone and phthalic acid |
| FR2421864A1 (fr) | 1978-04-05 | 1979-11-02 | Hoechst France | Procede de fabrication de l'acide hydroxy-4, dimethoxy-3,5 benzoique a partir de l'acide trimethoxy-3,4,5 benzoique |
| US4334074A (en) | 1981-02-02 | 1982-06-08 | The Dow Chemical Company | Method of recovering 3,6-dichloropicolinic acid from basic aqueous solutions of salts thereof |
| DE3345411A1 (de) | 1983-12-15 | 1985-06-27 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur reindarstellung von carbonsaeuren |
| US4771001A (en) | 1986-03-27 | 1988-09-13 | Neurex Corp. | Production of lactic acid by continuous fermentation using an inexpensive raw material and a simplified method of lactic acid purification |
| US5168055A (en) | 1986-06-11 | 1992-12-01 | Rathin Datta | Fermentation and purification process for succinic acid |
| US5202476A (en) * | 1988-04-29 | 1993-04-13 | Takeda Chemical Industries, Ltd. | Purification of 2-keto-L-gulonic acid |
| FR2636343B1 (enExample) | 1988-09-13 | 1994-11-25 | Rhone Poulenc Sante | |
| FR2648136B1 (fr) | 1989-06-12 | 1994-06-17 | Rhone Poulenc Sante | Procede de preparation de l'acide ascorbique |
| CH678057A5 (de) | 1989-06-26 | 1991-07-31 | Enco Eng Ag | Verfahren zur herstellung von natrium- oder kalium-l-ascorbat. |
| US5202475A (en) | 1990-09-27 | 1993-04-13 | Eastman Kodak Company | Process for preparation of cyclohexanedicarboxylic acid |
| EP0483831B1 (en) | 1990-11-02 | 1995-09-06 | Mitsubishi Chemical Corporation | Process for separating an organic acid or acids from an organic acid-containing solution |
| US5210296A (en) | 1990-11-19 | 1993-05-11 | E. I. Du Pont De Nemours And Company | Recovery of lactate esters and lactic acid from fermentation broth |
| US5159110A (en) | 1991-05-16 | 1992-10-27 | W. R. Grace & Co.-Conn. | Process for recovering n-methyliminodiacetic acid from sodium sulfate |
| IT1254254B (it) | 1992-03-11 | 1995-09-14 | Erregierre Ind Chim | Procedimento per la preparazione di acido iodesossicolico ad elevata purezza per impiego farmaceutico |
| US5352825A (en) | 1993-07-06 | 1994-10-04 | Hoarmann & Reimer Corp. | Recovery of organic acid salts from impure process streams by addition of bases |
| CA2126365C (en) | 1993-07-06 | 1999-08-24 | Steven W. Felman | Recovery of citric acid from impure process streams by addition of strong acids and salts thereof |
| US5426219A (en) | 1993-07-26 | 1995-06-20 | A.E. Staley Manufacturing Co. | Process for recovering organic acids |
| US5410076A (en) | 1993-11-12 | 1995-04-25 | Lever Brothers Company, Division Of Conopco, Inc. | Process for the preparation of bis(amidocarboxylic acid) |
| KR960023076A (ko) | 1994-12-09 | 1996-07-18 | 미우라 아끼라 | L-아스파르트산의 제조 방법 |
| US5522995A (en) | 1995-02-28 | 1996-06-04 | Cockrem; Michael C. M. | Process for recovering organic acids from aqueous salt solutions |
| JP3976832B2 (ja) | 1996-04-30 | 2007-09-19 | ディーエスエム アイピー アセッツ ビー．ブイ． | ２−ケト−ｌ−グロン酸の単離方法 |
-
2000
- 2000-03-07 US US09/519,936 patent/US6670505B1/en not_active Expired - Fee Related
-
2001
- 2001-03-06 DE DE60124229T patent/DE60124229T2/de not_active Expired - Fee Related
- 2001-03-06 WO PCT/US2001/007140 patent/WO2001066508A2/en not_active Ceased
- 2001-03-06 CN CNB018090400A patent/CN100413839C/zh not_active Expired - Fee Related
- 2001-03-06 JP JP2001565329A patent/JP2003525923A/ja not_active Withdrawn
- 2001-03-06 EP EP01918380A patent/EP1261574B1/en not_active Expired - Lifetime
- 2001-03-06 AT AT01918380T patent/ATE344225T1/de not_active IP Right Cessation
- 2001-03-06 BR BR0109005-4A patent/BR0109005A/pt not_active IP Right Cessation
- 2001-08-03 US US09/921,946 patent/US20020026077A1/en not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005030973A1 (ja) * | 2003-09-30 | 2007-11-15 | 味の素株式会社 | 発酵液からのコハク酸の精製方法 |
| JP2022514350A (ja) * | 2018-12-19 | 2022-02-10 | ビーエーエスエフ ソシエタス・ヨーロピア | バイオマス及び少なくとも１種のオリゴ糖を含む溶液からバイオマスを分離する方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR0109005A (pt) | 2003-06-03 |
| DE60124229T2 (de) | 2007-02-15 |
| WO2001066508A3 (en) | 2002-05-02 |
| US6670505B1 (en) | 2003-12-30 |
| EP1261574A2 (en) | 2002-12-04 |
| WO2001066508A2 (en) | 2001-09-13 |
| EP1261574B1 (en) | 2006-11-02 |
| CN100413839C (zh) | 2008-08-27 |
| ATE344225T1 (de) | 2006-11-15 |
| DE60124229D1 (de) | 2006-12-14 |
| CN1427813A (zh) | 2003-07-02 |
| US20020026077A1 (en) | 2002-02-28 |
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