ES2689554T3 - Procedimiento de aislamiento de un ácido carboxílico a partir de una solución acuosa - Google Patents
Procedimiento de aislamiento de un ácido carboxílico a partir de una solución acuosa Download PDFInfo
- Publication number
- ES2689554T3 ES2689554T3 ES12806504.2T ES12806504T ES2689554T3 ES 2689554 T3 ES2689554 T3 ES 2689554T3 ES 12806504 T ES12806504 T ES 12806504T ES 2689554 T3 ES2689554 T3 ES 2689554T3
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- Prior art keywords
- acid
- carboxylic acid
- aqueous
- extraction
- weight
- Prior art date
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims abstract description 187
- 239000007864 aqueous solution Substances 0.000 title description 24
- 238000002955 isolation Methods 0.000 title description 2
- 238000000605 extraction Methods 0.000 claims abstract description 252
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims abstract description 195
- 239000007788 liquid Substances 0.000 claims abstract description 134
- 239000000203 mixture Substances 0.000 claims abstract description 130
- 229910001629 magnesium chloride Inorganic materials 0.000 claims abstract description 97
- 238000000034 method Methods 0.000 claims abstract description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 59
- 239000003960 organic solvent Substances 0.000 claims abstract description 52
- 230000008569 process Effects 0.000 claims abstract description 46
- 238000005979 thermal decomposition reaction Methods 0.000 claims abstract description 24
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000395 magnesium oxide Substances 0.000 claims abstract description 18
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 11
- 238000011084 recovery Methods 0.000 claims abstract description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 142
- 239000004310 lactic acid Substances 0.000 claims description 71
- 235000014655 lactic acid Nutrition 0.000 claims description 71
- 238000000855 fermentation Methods 0.000 claims description 52
- 230000004151 fermentation Effects 0.000 claims description 52
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical group CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 43
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 43
- -1 magnesium carboxylate Chemical class 0.000 claims description 34
- 239000011777 magnesium Substances 0.000 claims description 22
- 229910052749 magnesium Inorganic materials 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 230000020477 pH reduction Effects 0.000 claims description 21
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 claims description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- AFENDNXGAFYKQO-VKHMYHEASA-N (S)-2-hydroxybutyric acid Chemical compound CC[C@H](O)C(O)=O AFENDNXGAFYKQO-VKHMYHEASA-N 0.000 claims description 17
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 16
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 14
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 13
- 150000002576 ketones Chemical class 0.000 claims description 13
- 244000005700 microbiome Species 0.000 claims description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 11
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims description 10
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 claims description 10
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 10
- 239000000347 magnesium hydroxide Substances 0.000 claims description 10
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000001530 fumaric acid Substances 0.000 claims description 8
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 8
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 7
- 229940006015 4-hydroxybutyric acid Drugs 0.000 claims description 7
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 7
- 235000019260 propionic acid Nutrition 0.000 claims description 7
- 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 description 7
- 150000002170 ethers Chemical class 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- 239000001630 malic acid Substances 0.000 claims description 3
- 235000011090 malic acid Nutrition 0.000 claims description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
- 239000001384 succinic acid Substances 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229940040102 levulinic acid Drugs 0.000 claims description 2
- 229940005605 valeric acid Drugs 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 abstract description 3
- 229960002337 magnesium chloride Drugs 0.000 description 83
- 239000000243 solution Substances 0.000 description 82
- 239000002253 acid Substances 0.000 description 64
- 239000012071 phase Substances 0.000 description 63
- 239000002904 solvent Substances 0.000 description 57
- 239000000047 product Substances 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000012527 feed solution Substances 0.000 description 22
- 235000010633 broth Nutrition 0.000 description 20
- 238000009826 distribution Methods 0.000 description 19
- 239000012535 impurity Substances 0.000 description 17
- 229940091250 magnesium supplement Drugs 0.000 description 17
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 239000002028 Biomass Substances 0.000 description 13
- 239000012467 final product Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 150000007524 organic acids Chemical class 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000003918 potentiometric titration Methods 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 239000012266 salt solution Substances 0.000 description 6
- 239000002699 waste material Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 230000010355 oscillation Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000012223 aqueous fraction Substances 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000006193 liquid solution Substances 0.000 description 2
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 2
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 2
- OVGXLJDWSLQDRT-UHFFFAOYSA-L magnesium lactate Chemical compound [Mg+2].CC(O)C([O-])=O.CC(O)C([O-])=O OVGXLJDWSLQDRT-UHFFFAOYSA-L 0.000 description 2
- 239000000626 magnesium lactate Substances 0.000 description 2
- 229960004658 magnesium lactate Drugs 0.000 description 2
- 235000015229 magnesium lactate Nutrition 0.000 description 2
- 229960002510 mandelic acid Drugs 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ZCUYEVGOLYJYMT-UHFFFAOYSA-N 2-ethyl-2-hydroxy-5-methylhexanoic acid Chemical compound CCC(O)(C(O)=O)CCC(C)C ZCUYEVGOLYJYMT-UHFFFAOYSA-N 0.000 description 1
- BVKWAKVSGKSKIX-UHFFFAOYSA-N 3-methylbutyl 2-hydroxybutanoate Chemical compound OC(C(=O)OCCC(C)C)CC BVKWAKVSGKSKIX-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 229910013804 M2HPO4 Inorganic materials 0.000 description 1
- 229910013868 M2SO4 Inorganic materials 0.000 description 1
- 229910013915 M3PO4 Inorganic materials 0.000 description 1
- 229910017736 MH2PO4 Inorganic materials 0.000 description 1
- 229910017738 MHSO4 Inorganic materials 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 229910000473 manganese(VI) oxide Inorganic materials 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/44—Polycarboxylic acids
-
- 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
-
- 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
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/10—Succinic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/15—Fumaric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/08—Lactic acid
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/56—Lactic acid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0426—Counter-current multistage extraction towers in a vertical or sloping position
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Extraction Or Liquid Replacement (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US201161579730P | 2011-12-23 | 2011-12-23 | |
| US201161579730P | 2011-12-23 | ||
| EP11195691 | 2011-12-23 | ||
| EP11195691 | 2011-12-23 | ||
| PCT/EP2012/076741 WO2013093047A1 (en) | 2011-12-23 | 2012-12-21 | Method for isolating a carboxylic acid from an aqueous solution |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2689554T3 true ES2689554T3 (es) | 2018-11-14 |
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| ES12806501.8T Active ES2669319T3 (es) | 2011-12-23 | 2012-12-21 | Extracción de ácido láctico |
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| ES12806501.8T Active ES2669319T3 (es) | 2011-12-23 | 2012-12-21 | Extracción de ácido láctico |
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| VN39373A1 (en) * | 2011-12-23 | 2014-09-25 | Purac Biochem Bv | Method for isolating a carboxylic acid from an aqueous solution |
| AU2013217968B2 (en) * | 2012-02-08 | 2015-12-17 | Purac Biochem B.V. | Carboxylate acidification |
| WO2014125027A1 (en) * | 2013-02-14 | 2014-08-21 | Purac Biochem Bv | Method for manufacturing succinic acid esters |
| EP2821368A1 (en) * | 2013-07-03 | 2015-01-07 | PURAC Biochem BV | Method for processing magnesium chloride solutions |
| EP3770118A1 (en) | 2014-04-01 | 2021-01-27 | Purac Biochem bv | Thermal decomposition of magnesium chloride |
| CN106574278B (zh) | 2014-07-28 | 2021-05-04 | 普拉克生化公司 | 通过分开的糖化和发酵步骤从木质纤维素材料制备乳酸和/或乳酸盐 |
| PL3174988T3 (pl) | 2014-07-28 | 2023-01-02 | Purac Biochem Bv | Sposób wytwarzania kwasu mlekowego |
| CN105503578B (zh) * | 2014-09-26 | 2018-03-02 | 常茂生物化学工程股份有限公司 | 一种用萃取剂从发酵液中提取丁二酸的方法 |
| EP3056490A1 (en) | 2015-02-13 | 2016-08-17 | PURAC Biochem BV | Method for manufacturing lactide |
| US10577339B2 (en) | 2015-03-17 | 2020-03-03 | Purac Biochem Bv | Method for manufacturing furan-2,5-dicarboxylic acid (FDCA) from a salt solution |
| JP6361980B2 (ja) * | 2015-05-26 | 2018-07-25 | 住友金属鉱山株式会社 | 有機溶液中のシュウ酸の分析方法 |
| JP6667646B2 (ja) * | 2016-01-19 | 2020-03-18 | ピュラック バイオケム ビー． ブイ． | 塩化マグネシウム溶液の改良処理方法及びカルボン酸の製造方法 |
| JP6884802B2 (ja) * | 2016-05-30 | 2021-06-09 | ピュラック バイオケム ビー． ブイ． | 固体発酵生成物からバイオマスを分離する方法 |
| CN106220493B (zh) * | 2016-07-22 | 2018-09-25 | 南京正大天晴制药有限公司 | 一种l-苹果酸的精制方法 |
| CN107353197A (zh) * | 2017-06-09 | 2017-11-17 | 安徽丰原发酵技术工程研究有限公司 | 一种提取3‑羟基丙酸的方法 |
| CN107344911A (zh) * | 2017-06-09 | 2017-11-14 | 安徽丰原发酵技术工程研究有限公司 | 一种提取柠檬酸/柠檬酸盐的方法 |
| CN107176907A (zh) * | 2017-06-09 | 2017-09-19 | 安徽丰原发酵技术工程研究有限公司 | 一种提取苹果酸/苹果酸盐的方法 |
| CN107353196A (zh) * | 2017-06-09 | 2017-11-17 | 安徽丰原发酵技术工程研究有限公司 | 一种提取丁二酸/丁二酸盐的方法 |
| CN110845326A (zh) * | 2017-06-09 | 2020-02-28 | 安徽丰原发酵技术工程研究有限公司 | 一种通过脱水萃取制备乳酸和丙交酯的方法 |
| EP3701035A4 (en) | 2017-10-26 | 2021-05-26 | Noroo IC Co., Ltd. | PREPARATION AND SEPARATION OF 3-HYDROXYPROPIONIC ACID |
| IL282900B2 (en) | 2018-11-26 | 2025-02-01 | Triplew Ltd | Magnesium lactate purification from fermentation solutions containing large amounts of impurities |
| CN110028402B (zh) * | 2019-05-30 | 2022-01-25 | 上海泰坦科技股份有限公司 | 一种提取3-羟基丙酸的方法 |
| WO2021056094A1 (en) | 2019-09-24 | 2021-04-01 | Genetec Inc. | Intermediary device for daisy chain and tree configuration in hybrid data/power connection |
| CN112745215B (zh) * | 2019-10-31 | 2022-11-11 | 中国石油化工股份有限公司 | 一种从乳酸盐的含水原料中转化乳酸和提取乳酸相耦合的方法 |
| AU2021207300B2 (en) * | 2020-01-15 | 2024-01-04 | Purac Biochem B.V. | Method for purifying magnesium chloride solutions |
| CN115427354B (zh) | 2020-04-20 | 2025-03-11 | 普拉克生化公司 | 制备高纯度氧化镁的方法 |
| US11770155B2 (en) | 2020-05-19 | 2023-09-26 | Genetec Inc. | Power distribution and data routing in a network of devices interconnected by hybrid data/power links |
| US12227474B2 (en) | 2023-05-12 | 2025-02-18 | Biofine Technology, Llc | Methods of producing and recovering levulinic acid |
| WO2025083005A1 (en) | 2023-10-17 | 2025-04-24 | Purac Biochem B.V. | Process for manufacturing high-purity magnesium oxide from magnesium chloride |
| CN119176749B (zh) * | 2024-11-22 | 2025-07-18 | 上海金发科技发展有限公司 | 一种生物基丁二酸组合物及其制备方法、由其制备的聚酯 |
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| VN39373A1 (en) * | 2011-12-23 | 2014-09-25 | Purac Biochem Bv | Method for isolating a carboxylic acid from an aqueous solution |
| EP2666763B1 (en) | 2012-05-24 | 2014-12-31 | Purac Biochem B.V. | Carboxylic acid recovery from magnesium carboxylate mixture |
| CN102690189A (zh) * | 2012-06-12 | 2012-09-26 | 南京工业大学 | 一种从丁二酸发酵液或丁二酸结晶母液中萃取分离丁二酸的方法 |
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2012
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2014
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