CN113461517B - Organic liquid and method for extracting lactic acid based on molecular recognition - Google Patents
Organic liquid and method for extracting lactic acid based on molecular recognition Download PDFInfo
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- CN113461517B CN113461517B CN202110750798.1A CN202110750798A CN113461517B CN 113461517 B CN113461517 B CN 113461517B CN 202110750798 A CN202110750798 A CN 202110750798A CN 113461517 B CN113461517 B CN 113461517B
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title claims abstract description 198
- 239000004310 lactic acid Substances 0.000 title claims abstract description 99
- 235000014655 lactic acid Nutrition 0.000 title claims abstract description 99
- 239000007788 liquid Substances 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 27
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 33
- 239000012074 organic phase Substances 0.000 claims abstract description 30
- 238000000855 fermentation Methods 0.000 claims abstract description 25
- 230000004151 fermentation Effects 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 238000005406 washing Methods 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 11
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 abstract description 9
- 239000012071 phase Substances 0.000 abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- 229920006395 saturated elastomer Polymers 0.000 abstract description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000012535 impurity Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 description 3
- 239000001527 calcium lactate Substances 0.000 description 3
- 229960002401 calcium lactate Drugs 0.000 description 3
- 235000011086 calcium lactate Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-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
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- PVXPPJIGRGXGCY-TZLCEDOOSA-N 6-O-alpha-D-glucopyranosyl-D-fructofuranose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)C(O)(CO)O1 PVXPPJIGRGXGCY-TZLCEDOOSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 1
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 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
- 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
- 239000004471 Glycine Substances 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
- AYRXSINWFIIFAE-SCLMCMATSA-N Isomaltose Natural products OC[C@H]1O[C@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)[C@@H](O)[C@@H](O)[C@@H]1O AYRXSINWFIIFAE-SCLMCMATSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 241000186660 Lactobacillus Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- LUEWUZLMQUOBSB-UHFFFAOYSA-N UNPD55895 Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(OC3C(OC(O)C(O)C3O)CO)C(O)C2O)CO)C(O)C1O LUEWUZLMQUOBSB-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 229940061720 alpha hydroxy acid Drugs 0.000 description 1
- 150000001280 alpha hydroxy acids Chemical class 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 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
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229960005069 calcium Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- -1 chloride ion Chemical compound 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- DLRVVLDZNNYCBX-RTPHMHGBSA-N isomaltose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)C(O)O1 DLRVVLDZNNYCBX-RTPHMHGBSA-N 0.000 description 1
- 229940089442 lacticare Drugs 0.000 description 1
- 229940039696 lactobacillus Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- UYQJCPNSAVWAFU-UHFFFAOYSA-N malto-tetraose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(CO)O1 UYQJCPNSAVWAFU-UHFFFAOYSA-N 0.000 description 1
- LUEWUZLMQUOBSB-OUBHKODOSA-N maltotetraose Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O[C@@H]3[C@@H](O[C@@H](O)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-OUBHKODOSA-N 0.000 description 1
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 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 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 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
- 239000004474 valine Substances 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 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
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses an organic liquid and a method for extracting lactic acid based on molecular recognition, wherein the organic liquid is selected from a structural general formula (I)General structural formula (II)And general structural formula (III)One or more of the formulae (I) - (III), R 1 、R 2 、R 3 、R 4 、R 5 And R is 6 Are each independently selected from a hydrogen atom, a linear or branched saturated or unsaturated alkane having 1 to 20 carbon atoms, and X is selected from a hydrogen atom, a carbonyl group, a hydroxyl group and an acetyl group. The organic liquid and the method for extracting the lactic acid based on molecular recognition, which are disclosed by the invention, effectively identify the lactic acid in the lactic acid fermentation liquid through the inter-ion action, the hydrogen bond action, the pi-pi action, the dipole action, the spatial configuration and the steric hindrance, form a hydrophobic organic phase with the lactic acid, transfer the lactic acid from the water phase to the hydrophobic organic phase, realize the purposes of identification and separation, and realize simple and rapid separation.
Description
Technical Field
The invention relates to the technical field of lactic acid extraction processes, in particular to an organic liquid and a method for extracting lactic acid based on molecular recognition.
Background
Lactic acid is an important organic acid, widely exists in human bodies, animals and plants, and has wide application in the fields of food, feed, chemical industry, medicine and the like. The production method of lactic acid includes fermentation method, chemical synthesis method and enzyme method. At present, the production of the lactic acid with high optical purity mainly uses microbial fermentation, and fermentation strains are lactobacillus, rhizopus oryzae and the like. The extraction and separation methods of lactic acid fermentation broth are various, such as an ion exchange method, a solvent extraction method, a distillation method, an esterification method, a crystallization method and the like, but the existing technology generally has the problems of low extraction rate, low purity of finished products, poor storage stability, long extraction process time, difficult operation and the like.
The lactic acid fermentation broth contains saccharides such as trehalose, sucrose, glucose, fructose, isomaltose, maltose, cellobiose, isomaltulose, maltose, maltotriose, and maltotetraose, and also contains various organic carboxylic acids such as pyruvic acid, formic acid, acetic acid, propionic acid, malic acid, fumaric acid, succinic acid, aconitic acid, itaconic acid, oxalic acid, and citric acid, and also contains inorganic ions such as cations such as potassium, sodium, calcium, and magnesium, anions such as chloride ion, and sulfate ion, and also contains various amino acids such as alanine, valine, serine, glutamine, glycine, and the like, and also contains proteins and pigments. Lactic acid is used as a target product, and the compounds or the compound classes are all impurities of the lactic acid, and are main substances separated and removed. Among these, the most similar impurities are organic carboxylic acid impurities, and between them are impurities such as amino acids, sugars and pigments. From the above, it can be seen that the organic carboxylic acid is most difficult to remove due to its structural similarity with lactic acid and its similar properties.
At present, the method for extracting lactic acid from lactic acid fermentation broth has corresponding defects, particularly, the most similar organic acid impurities are separated from lactic acid, and a separation and purification system based on molecular recognition is not established.
Disclosure of Invention
The invention aims to provide an organic liquid and a method for extracting lactic acid based on molecular recognition, which are used for solving the problems that the method for separating and purifying lactic acid from lactic acid fermentation liquor has corresponding defects and can not directly and effectively recognize and separate lactic acid from a plurality of impurities.
In order to achieve the above object, the present invention provides an organic liquid and a method for extracting lactic acid based on molecular recognition.
A method for extracting lactic acid from an organic liquid comprising the steps of:
1) Adding organic liquid into lactic acid fermentation broth, extracting for multiple times, stirring at 30-40deg.C for more than 5min, standing for layering, and mixing to obtain hydrophobic organic phase;
2) Adding pure water into the hydrophobic organic phase for washing for multiple times to obtain a lactic acid aqueous solution;
3) Continuously adding organic liquid into the lactic acid aqueous solution, countercurrent washing for a plurality of times, standing and layering until the concentration of lactic acid in the lactic acid aqueous solution is lower than 0.5g/L, and obtaining a secondary hydrophobic organic phase;
4) Adding pure water into the secondary hydrophobic organic phase, countercurrent washing for multiple times, standing and layering to obtain a secondary lactic acid aqueous solution;
5) Concentrating the secondary lactic acid aqueous solution to obtain a lactic acid product.
Further, in step 1), the volume ratio of lactic acid fermentation broth to organic liquid is 1:2.
Further, the volume ratio of the hydrophobic organic phase to the pure water in step 2) is 1:1.
Further, in step 4), the volume ratio of the secondary hydrophobic organic phase to the pure water is 1:2.
Therefore, the organic liquid and the method for extracting the lactic acid based on molecular recognition have the following beneficial effects:
1. lactic acid has two functional groups of hydroxyl and carboxyl, is alpha-hydroxy acid with chirality, molecules in organic liquid contain one, two or more hydroxyl, carbonyl, amino or amide groups, effectively identify lactic acid through the actions of ion, hydrogen bond, pi-pi action, dipole action and steric hindrance, form a hydrophobic organic phase with the lactic acid, and transfer the lactic acid from an aqueous phase to the hydrophobic organic phase, so as to realize the dual purposes of identification and separation;
2. washing lactic acid in a hydrophobic organic phase into a water phase by pure water, then obtaining a lactic acid product, and returning the organic liquid after washing the lactic acid to the separation of the lactic acid fermentation liquor separated before, so that the lactic acid fermentation liquor is a closed circulation system, and the organic liquid can be reused, thereby avoiding the waste of the lactic acid fermentation liquor;
3. the binding force of the added organic liquid and the lactic acid is higher than the binding force of the added organic liquid and the impurities, so that the organic liquid has a directional recognition effect on lactic acid molecules;
4. effectively reduces the separation steps, directly separates the lactic acid for purification, and sequentially removes other impurities without the steps, thereby reducing the cost.
The technical scheme of the invention is further described in detail through examples.
Detailed Description
The present invention will be further described below, and it should be noted that the present embodiment provides a detailed implementation manner and a specific operation procedure on the premise of the present technical solution, but the present invention is not limited to the present embodiment.
An organic liquid for extracting lactic acid based on molecular recognition has a chemical structural formula as follows, but is not limited to the following structure:
；
wherein R is 1 、R 2 、R 3 、R 4 、R 5 And R is 6 Are each independently selected from hydrogen atoms, and linear or branched saturated or unsaturated alkanes having 1 to 20 carbon atoms.
A method for extracting lactic acid from an organic liquid comprising the steps of:
the lactic acid fermentation liquid is mainly prepared by fermenting calcium lactate, adding concentrated sulfuric acid into the calcium lactate to obtain free calcium lactate acidolysis liquid, wherein the lactic acid acidolysis liquid contains 18% of lactic acid, and the lactic acid acidolysis liquid is applied to the following extraction steps;
1) Adding the lactic acid fermentation liquor into alpha-carbonyl pyrrole organic liquid for extraction for multiple times until the lactic acid content in the lactic acid fermentation liquor is below a target set value, wherein the volume ratio of the lactic acid fermentation liquor to the alpha-carbonyl pyrrole is 1:2, fully stirring for 5min at 35 ℃ for each extraction, standing and layering under the same temperature condition, and merging to obtain a hydrophobic organic phase, wherein 76% of lactic acid is transferred from the lactic acid fermentation liquor into the hydrophobic organic phase, and the transfer rate of other organic acid impurities into the hydrophobic organic phase is lower than 1%;
2) Adding pure water into the hydrophobic organic phase for washing for multiple times, wherein the volume ratio of the hydrophobic organic phase to the pure water is 1:1, so as to obtain a lactic acid aqueous solution with the mass concentration of 6.7%, washing lactic acid in the hydrophobic organic phase into a water phase by using the pure water, and using the washed hydrophobic organic phase as an organic liquid in the process of separating lactic acid fermentation liquor in the step 1, thereby avoiding waste;
3) Continuously adding alpha-carbonyl pyrrole into the lactic acid aqueous solution, carrying out countercurrent washing for 8 times, standing and layering until the concentration of lactic acid in the lactic acid aqueous solution is lower than 0.5g/L, and obtaining a secondary hydrophobic organic phase, wherein the transfer rate of lactic acid from a water phase to the secondary hydrophobic organic phase is 99.7%;
4) Adding pure water into the secondary hydrophobic organic phase, wherein the volume ratio of the secondary hydrophobic organic phase to the pure water is 1:2, and carrying out countercurrent washing for 12 times and standing for layering to obtain a secondary lactic acid aqueous solution with the mass concentration of 17.58%;
5) Concentrating the secondary lactic acid aqueous solution to obtain lactic acid product, wherein the lactic acid yield is 97.8%, and the lactic acid concentration reaches 98.8%.
After the hydrophobic organic phase is obtained, the organic liquid can be added into the original lactic acid fermentation liquor again for extraction until the content of lactic acid in the lactic acid fermentation liquor reaches a target set value, then the hydrophobic organic phases obtained by multiple times of extraction are combined for the next step, and the aqueous solution of lactic acid obtained by the method can be dissolved in the organic liquid for multiple times and then washed by pure water until the purity of the lactic acid reaches the required purity, wherein the yield of the separated lactic acid is far higher than that of the traditional process technology, and the chemical purity of the obtained lactic acid product reaches more than 99 percent.
Therefore, the organic liquid and the method for extracting the lactic acid based on molecular recognition adopt the structure, the organic liquid recognizes lactic acid molecules in the fermentation broth through the actions of ions, hydrogen bonding, pi-pi action, dipole action, space configuration and steric hindrance, the organic liquid contains one or more hydrophobic molecules, one or more hydroxyl, carbonyl, amino or amide groups in the molecules interact with alpha-hydroxyl and carboxyl in the lactic acid molecules, so that the lactic acid in the fermentation broth is effectively recognized, a new hydrophobic phase is formed with the lactic acid, the lactic acid is transferred from an aqueous phase to the organic hydrophobic phase, the purposes of recognition and separation are realized, and the separation and purification are simple.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention and not for limiting it, and although the present invention has been described in detail with reference to the preferred embodiments, it will be understood by those skilled in the art that: the technical scheme of the invention can be modified or replaced by the same, and the modified technical scheme cannot deviate from the spirit and scope of the technical scheme of the invention.
Claims (3)
1. A method for extracting lactic acid based on molecular recognition, which is characterized by comprising the following steps:
1) Adding alpha-carbonyl pyrrole organic liquid into lactic acid fermentation liquor for multiple extraction, fully stirring for more than 5min at 30-40 ℃ for each extraction, standing for layering, and merging to obtain a hydrophobic organic phase; in the step 1), the volume ratio of the lactic acid fermentation liquid to the alpha-carbonyl pyrrole organic liquid is 1:2;
2) Adding pure water into the hydrophobic organic phase for washing for multiple times to obtain a lactic acid aqueous solution;
3) Continuously adding alpha-carbonyl pyrrole organic liquid into the lactic acid aqueous solution, countercurrent washing for a plurality of times, standing and layering until the lactic acid concentration in the lactic acid aqueous solution is lower than 0.5g/L, so as to obtain a secondary hydrophobic organic phase;
4) Adding pure water into the secondary hydrophobic organic phase, countercurrent washing for multiple times, standing and layering to obtain a secondary lactic acid aqueous solution;
5) Concentrating the secondary lactic acid aqueous solution to obtain a lactic acid product.
2. The method for extracting lactic acid based on molecular recognition according to claim 1, wherein: the volume ratio of the hydrophobic organic phase to the pure water in step 2) is 1:1.
3. The method for extracting lactic acid based on molecular recognition according to claim 1, wherein: the volume ratio of the secondary hydrophobic organic phase to the pure water in step 4) was 1:2.
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