CN111269107B - L-lactic acid purification and refining method - Google Patents
L-lactic acid purification and refining method Download PDFInfo
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- CN111269107B CN111269107B CN202010273014.6A CN202010273014A CN111269107B CN 111269107 B CN111269107 B CN 111269107B CN 202010273014 A CN202010273014 A CN 202010273014A CN 111269107 B CN111269107 B CN 111269107B
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- lactic acid
- ion exchange
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- liquid
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- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 title claims abstract description 378
- 238000000034 method Methods 0.000 title claims abstract description 71
- 238000007670 refining Methods 0.000 title claims abstract description 39
- 238000000746 purification Methods 0.000 title abstract description 25
- 238000005342 ion exchange Methods 0.000 claims abstract description 122
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 101
- 239000007788 liquid Substances 0.000 claims abstract description 94
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 92
- 238000000855 fermentation Methods 0.000 claims abstract description 52
- 230000004151 fermentation Effects 0.000 claims abstract description 52
- 239000004310 lactic acid Substances 0.000 claims abstract description 46
- 235000014655 lactic acid Nutrition 0.000 claims abstract description 46
- 239000012528 membrane Substances 0.000 claims abstract description 35
- 238000001728 nano-filtration Methods 0.000 claims abstract description 35
- 150000001768 cations Chemical class 0.000 claims abstract description 25
- 239000002994 raw material Substances 0.000 claims abstract description 20
- 238000001914 filtration Methods 0.000 claims abstract description 16
- 229920000747 poly(lactic acid) Polymers 0.000 claims abstract description 14
- 239000004626 polylactic acid Substances 0.000 claims abstract description 14
- 238000000926 separation method Methods 0.000 claims abstract description 14
- 238000005341 cation exchange Methods 0.000 claims abstract description 13
- 238000005349 anion exchange Methods 0.000 claims abstract description 11
- 238000004042 decolorization Methods 0.000 claims description 26
- 150000001450 anions Chemical class 0.000 claims description 24
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 230000008929 regeneration Effects 0.000 claims description 17
- 238000011069 regeneration method Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- 239000000706 filtrate Substances 0.000 claims description 11
- -1 iron ions Chemical class 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 10
- 229910001424 calcium ion Inorganic materials 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-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
- 229910052742 iron Inorganic materials 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 239000000945 filler Substances 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000000354 decomposition reaction Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 230000014759 maintenance of location Effects 0.000 claims description 6
- 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 4
- 239000003957 anion exchange resin Substances 0.000 claims description 4
- 239000003729 cation exchange resin Substances 0.000 claims description 4
- 239000007790 solid phase Substances 0.000 claims description 4
- 238000000502 dialysis Methods 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 229910052602 gypsum Inorganic materials 0.000 claims description 3
- 239000010440 gypsum Substances 0.000 claims description 3
- 238000000526 short-path distillation Methods 0.000 abstract description 24
- 238000004519 manufacturing process Methods 0.000 abstract description 16
- 241001052560 Thallis Species 0.000 abstract description 8
- 235000013305 food Nutrition 0.000 abstract description 5
- 238000004094 preconcentration Methods 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 72
- 239000000047 product Substances 0.000 description 30
- 239000000049 pigment Substances 0.000 description 18
- 239000012535 impurity Substances 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 230000001276 controlling effect Effects 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000007599 discharging Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000000199 molecular distillation Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- 239000002893 slag Substances 0.000 description 4
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 235000011941 Tilia x europaea Nutrition 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000002585 base Substances 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
- 235000011086 calcium lactate Nutrition 0.000 description 3
- 229960002401 calcium lactate Drugs 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
- 230000000694 effects Effects 0.000 description 3
- 239000008394 flocculating agent Substances 0.000 description 3
- 239000004571 lime Substances 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 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 2
- MKJXYGKVIBWPFZ-CEOVSRFSSA-L calcium;(2s)-2-hydroxypropanoate Chemical compound [Ca+2].C[C@H](O)C([O-])=O.C[C@H](O)C([O-])=O MKJXYGKVIBWPFZ-CEOVSRFSSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000003311 flocculating effect Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 229940116871 l-lactate Drugs 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 150000002482 oligosaccharides Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012492 regenerant Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000001540 sodium lactate Substances 0.000 description 2
- 235000011088 sodium lactate Nutrition 0.000 description 2
- 229940005581 sodium lactate Drugs 0.000 description 2
- NGSFWBMYFKHRBD-DKWTVANSSA-M sodium;(2s)-2-hydroxypropanoate Chemical compound [Na+].C[C@H](O)C([O-])=O NGSFWBMYFKHRBD-DKWTVANSSA-M 0.000 description 2
- 239000002910 solid waste Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 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
- 229930006000 Sucrose Natural products 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229920000704 biodegradable plastic Polymers 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229920006238 degradable plastic Polymers 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- LZCLXQDLBQLTDK-BYPYZUCNSA-N ethyl (2S)-lactate Chemical compound CCOC(=O)[C@H](C)O LZCLXQDLBQLTDK-BYPYZUCNSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229940101629 l- methyl lactate Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000011034 membrane dialysis Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- LPEKGGXMPWTOCB-VKHMYHEASA-N methyl (S)-lactate Chemical compound COC(=O)[C@H](C)O LPEKGGXMPWTOCB-VKHMYHEASA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F11/00—Compounds of calcium, strontium, or barium
- C01F11/46—Sulfates
-
- 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
-
- 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
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- 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
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Geology (AREA)
- Inorganic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (6)
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CN111269107B true CN111269107B (en) | 2021-08-03 |
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Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
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CN111777504B (en) * | 2020-08-11 | 2021-03-19 | 上海汉禾生物新材料科技有限公司 | Method for purifying L-lactic acid extracted from fermentation liquor |
CN112573885A (en) * | 2020-12-12 | 2021-03-30 | 南京霄祥工程技术有限公司 | Self-leveling mortar and preparation method thereof |
CN112551569B (en) * | 2020-12-31 | 2022-03-11 | 天津科技大学 | Method for producing alpha-calcium sulfate hemihydrate crystal whisker by taking fermentation liquor for producing lactic acid by calcium salt method as raw material and synchronously recovering lactic acid monomer |
CN113214076B (en) * | 2021-04-09 | 2023-03-24 | 安徽丰原生物技术股份有限公司 | Method for recovering lactic acid from lactic acid distillation kettle bottom liquid |
CN113527085A (en) * | 2021-07-23 | 2021-10-22 | 厦门世达膜工程有限公司 | Production method for purifying lactic acid from lactic acid fermentation liquor |
CN113773189A (en) * | 2021-08-02 | 2021-12-10 | 合肥信达膜科技有限公司 | Application of membrane process in lactic acid production |
CN114702379B (en) * | 2021-09-08 | 2022-09-20 | 欧尚元(天津)有限公司 | Purification method of red lactic acid |
CN114702381B (en) * | 2021-09-08 | 2022-09-20 | 欧尚元(天津)有限公司 | Method for extracting lactic acid from heavy-phase lactic acid |
CN114276233A (en) * | 2021-11-01 | 2022-04-05 | 欧尚元(天津)有限公司 | Refining and purifying method and purifying device for crude L-lactic acid |
CN114181071A (en) * | 2021-12-28 | 2022-03-15 | 普立思生物科技有限公司 | L-lactic acid fermentation liquor refining and purifying method |
CN114181070A (en) * | 2021-12-28 | 2022-03-15 | 普立思生物科技有限公司 | Method for extracting high-purity L-lactic acid by using molecular distillation heavy phase and nanofiltration membrane concentrated solution |
CN114573448B (en) * | 2022-01-29 | 2023-12-15 | 安徽丰原发酵技术工程研究有限公司 | Method for extracting lactic acid |
CN114409530A (en) * | 2022-02-16 | 2022-04-29 | 欧尚元(天津)有限公司 | Purification method of L-lactic acid |
CN115028815A (en) * | 2022-08-02 | 2022-09-09 | 马鞍山同杰良生物材料有限公司 | Parallel production process method of polylactic acid |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2799754A1 (en) * | 1999-10-18 | 2001-04-20 | Roquette Freres | PROCESS FOR SEPARATING AND PURIFYING LACTIC ACID FROM A FERMENTATION MEDIUM |
CN109206310A (en) * | 2017-07-03 | 2019-01-15 | 中国石化扬子石油化工有限公司 | A method of extracting D-ALPHA-Hydroxypropionic acid from D-ALPHA-Hydroxypropionic acid calcium fermentation liquid |
CN107382713A (en) * | 2017-08-30 | 2017-11-24 | 沈阳金博地生态环保科技有限公司 | A kind of technique of purification of lactic acid |
CN109956859B (en) * | 2017-12-22 | 2021-10-19 | 广州中国科学院先进技术研究所 | Method for separating and purifying lactic acid from lactic acid fermentation liquor |
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