CN104080833B - 用于可聚合乳酸的品质测试以及其生产方法 - Google Patents
用于可聚合乳酸的品质测试以及其生产方法 Download PDFInfo
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- CN104080833B CN104080833B CN201280065824.6A CN201280065824A CN104080833B CN 104080833 B CN104080833 B CN 104080833B CN 201280065824 A CN201280065824 A CN 201280065824A CN 104080833 B CN104080833 B CN 104080833B
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- lactic acid
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- lactide
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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 224
- 239000004310 lactic acid Substances 0.000 title claims abstract description 115
- 235000014655 lactic acid Nutrition 0.000 title claims abstract description 112
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 238000012360 testing method Methods 0.000 title abstract description 19
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims abstract description 41
- 230000006340 racemization Effects 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 92
- 239000012530 fluid Substances 0.000 claims description 23
- 239000007788 liquid Substances 0.000 claims description 20
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 20
- 238000001704 evaporation Methods 0.000 claims description 12
- 238000005342 ion exchange Methods 0.000 claims description 12
- 238000001728 nano-filtration Methods 0.000 claims description 12
- 230000008020 evaporation Effects 0.000 claims description 11
- 238000000855 fermentation Methods 0.000 claims description 11
- 230000004151 fermentation Effects 0.000 claims description 11
- 239000000284 extract Substances 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 230000000149 penetrating effect Effects 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- GMWTXQKKRDUVQG-WOPPDYDQSA-N 4-amino-5-bromo-1-[(2r,3s,4s,5r)-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidin-2-one Chemical compound C[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N=C(N)C(Br)=C1 GMWTXQKKRDUVQG-WOPPDYDQSA-N 0.000 claims description 7
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 238000005469 granulation Methods 0.000 claims description 5
- 238000000108 ultra-filtration Methods 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 4
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 239000012465 retentate Substances 0.000 claims description 4
- 239000002028 Biomass Substances 0.000 claims description 3
- 238000001471 micro-filtration Methods 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 238000006068 polycondensation reaction Methods 0.000 abstract description 16
- 238000006116 polymerization reaction Methods 0.000 abstract description 9
- 238000004458 analytical method Methods 0.000 abstract description 5
- 238000005516 engineering process Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000009833 condensation Methods 0.000 description 13
- 230000005494 condensation Effects 0.000 description 13
- 210000003739 neck Anatomy 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000004626 polylactic acid Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 229940001447 lactate Drugs 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000001720 carbohydrates Chemical class 0.000 description 5
- 235000014633 carbohydrates Nutrition 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 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 4
- 239000004251 Ammonium lactate Substances 0.000 description 4
- 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 4
- 229940059265 ammonium lactate Drugs 0.000 description 4
- 235000019286 ammonium lactate Nutrition 0.000 description 4
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003729 cation exchange resin Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 210000000481 breast Anatomy 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000003179 granulation Effects 0.000 description 3
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241001468155 Lactobacillaceae Species 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 239000004695 Polyether sulfone Substances 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- BVFSYZFXJYAPQJ-UHFFFAOYSA-N butyl(oxo)tin Chemical compound CCCC[Sn]=O BVFSYZFXJYAPQJ-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000002361 compost Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 229920006393 polyether sulfone Polymers 0.000 description 2
- 238000004094 preconcentration Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 238000005204 segregation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- JJTUDXZGHPGLLC-ZXZARUISSA-N (3r,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-ZXZARUISSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- FBYFHODQAUBIOO-UHFFFAOYSA-N 2-(1-carboxyethoxy)propanoic acid Chemical compound OC(=O)C(C)OC(C)C(O)=O FBYFHODQAUBIOO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-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
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- QJGQUHMNIGDVPM-BJUDXGSMSA-N Nitrogen-13 Chemical compound [13N] QJGQUHMNIGDVPM-BJUDXGSMSA-N 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000562516 Thisbe Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- RZOBLYBZQXQGFY-UHFFFAOYSA-N ammonium lactate Chemical compound [NH4+].CC(O)C([O-])=O RZOBLYBZQXQGFY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000003413 degradative effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
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- 230000002349 favourable effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/88—Post-polymerisation treatment
- C08G63/89—Recovery of the polymer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/88—Post-polymerisation treatment
- C08G63/90—Purification; Drying
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/02—Separating microorganisms from their culture media
-
- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/02—Food
- G01N33/04—Dairy products
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/44—Resins; Plastics; Rubber; Leather
- G01N33/442—Resins; Plastics
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- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/20—Oxygen containing
- Y10T436/200833—Carbonyl, ether, aldehyde or ketone containing
- Y10T436/201666—Carboxylic acid
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Polymers & Plastics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Food Science & Technology (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Polyesters Or Polycarbonates (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
Description
离子 | 初始值 | 提取液 | 提余液 | 效率 |
硫酸根 | 75.084mg/L | 650.3mg/L | 34.697mg/L | 98.34% |
乳酸根 | 117.4g/L | 70.2g/L | 1.44g/L | 97.77% |
体积 | - | 1.81 | 2.01 | - |
离子 | 初始值 | 提取液 | 提余液 | 效率 |
硫酸根 | 71.580mg/L | 190mg/L | 46.920mg/L | 99.54% |
乳酸根 | 113.02g/L | 74.26g/L | 0.55g/L | 99.34% |
参数 | 初始值 | 渗透液 |
黄度指数(YI) | 28.55 | 2.4 |
麦芽糖g/L | 1.1 | 0.05 |
硫酸根g/L | 0.26 | 0.05 |
丙氨酸 | 0.22 | 0.10 |
天冬氨酸 | 1.23 | 0.35 |
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PCT/EP2012/004407 WO2013064219A2 (de) | 2011-11-04 | 2012-10-22 | Qualitätstest für polymerisationsfähige milchsäure und verfahren zu deren herstellung |
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CN106153488A (zh) * | 2015-04-13 | 2016-11-23 | 西南科技大学 | 一种高温水热法对聚乳酸薄膜降解性能的快速检测方法 |
US10164230B2 (en) | 2015-05-27 | 2018-12-25 | Samsung Electronics Co., Ltd. | Separator including microbial cellulose, method of producing the separator, and use of the separator |
DE102016119938A1 (de) | 2016-10-19 | 2018-04-19 | Thyssenkrupp Ag | Reinigung und Konzentrierung von Carbonsäuren aus Fermentationsprozessen |
CN109206310A (zh) * | 2017-07-03 | 2019-01-15 | 中国石化扬子石油化工有限公司 | 一种从d-乳酸钙发酵液中提取d-乳酸的方法 |
CN109206312A (zh) * | 2017-07-03 | 2019-01-15 | 中国石化扬子石油化工有限公司 | 一种从d-乳酸铵发酵液中分离纯化d-乳酸的方法 |
CN113640449A (zh) * | 2021-10-13 | 2021-11-12 | 山东省产品质量检验研究院 | 一种生物基降解材料聚乳酸的快速检测方法 |
CN115253994A (zh) * | 2022-08-25 | 2022-11-01 | 陕西德信祥能源科技有限公司 | 一种制备丙交酯的装置及方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1058210A (zh) * | 1990-07-13 | 1992-01-29 | 纳幕尔杜邦公司 | 用于丙交酯生产的高产率循环方法 |
CN1688569A (zh) * | 2002-08-06 | 2005-10-26 | 布鲁塞尔生物技术公司 | 以乳酸或其衍生物的溶液为原料制备聚交酯的方法 |
WO2010074222A1 (ja) * | 2008-12-26 | 2010-07-01 | 東レ株式会社 | 乳酸およびポリ乳酸の製造方法 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5177008A (en) * | 1987-12-22 | 1993-01-05 | Kampen Willem H | Process for manufacturing ethanol and for recovering glycerol, succinic acid, lactic acid, betaine, potassium sulfate, and free flowing distiller's dry grain and solubles or a solid fertilizer therefrom |
US5043458A (en) | 1990-05-03 | 1991-08-27 | E. I. Du Pont De Nemours And Company | One-step continuous process for preparing cyclic esters |
US5023349A (en) | 1990-05-08 | 1991-06-11 | E. I. Du Pont De Nemours And Company | Continuous process for rapid conversion of oligomers to cyclic esters |
US5142023A (en) * | 1992-01-24 | 1992-08-25 | Cargill, Incorporated | Continuous process for manufacture of lactide polymers with controlled optical purity |
US5521278A (en) | 1994-08-18 | 1996-05-28 | Ecological Chemical Products | Integrated process for the manufacture of lactide |
BE1011197A3 (fr) | 1997-06-06 | 1999-06-01 | Brussels Biotech En Abrege Bb | Procede de purification d'acide lactique. |
US6229046B1 (en) | 1997-10-14 | 2001-05-08 | Cargill, Incorported | Lactic acid processing methods arrangements and products |
DE19902897C2 (de) | 1999-01-18 | 2002-08-08 | Bfti Fassaden Technik Berlin I | Verschwindscharnier |
DE19902879A1 (de) * | 1999-01-25 | 2000-08-03 | Wolff Walsrode Ag | Verfahren zur Herstellung von hochreinem Dilactid |
DE10020898B4 (de) * | 2000-04-20 | 2004-02-05 | Inventa-Fischer Gmbh | Verfahren zur Herstellung von Polymilchsäure und Vorrichtung hierzu |
EP1357119B1 (en) * | 2001-01-31 | 2011-05-11 | Toyota Jidosha Kabushiki Kaisha | Process for producing lactide and process for producing polylactic acid starting with fermented lactic acid |
RU2301230C2 (ru) * | 2005-03-23 | 2007-06-20 | Российский химико-технологический университет им. Д.И. Менделеева | Способ получения лактида |
WO2006124633A1 (en) | 2005-05-13 | 2006-11-23 | Cargill, Incorporated | Production of lactic acid |
EP2030679A1 (de) | 2007-09-03 | 2009-03-04 | Uhde Inventa-Fischer GmbH | Polymerisationsreaktor, Polymerisationsvorrichtung, Verfahren zur Herstellung von bioabbaubarem Polyester sowie Verwendungen |
EP2031009A1 (de) * | 2007-09-03 | 2009-03-04 | Uhde Inventa-Fischer GmbH | Reinigungsvorrichtung zur Abtrennung von Dilactid aus Stoffgemischen, Polymerisationsvorrichtung, Verfahren zur Abtrennung von Dilactid aus Stoffgemischen sowie Verwendung |
DE102007045701B3 (de) | 2007-09-24 | 2009-05-14 | Uhde Gmbh | Gewinnung von Milchsäure durch Fermentation und Extraktion mit Aminen |
US8509100B2 (en) | 2008-02-15 | 2013-08-13 | Carrier Iq | User-initiated reporting of mobile communication system errors |
DE102009019248A1 (de) | 2009-04-30 | 2010-11-04 | Uhde Gmbh | Isolierung von organischen Säuren aus Fermenterbrühe mit Hilfe chromatographischer Methoden |
WO2010003534A1 (de) * | 2008-07-11 | 2010-01-14 | Uhde Gmbh | Isolierung von organischen säuren aus fermenterbrühe mit hilfe chromatographischer methoden |
-
2012
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1058210A (zh) * | 1990-07-13 | 1992-01-29 | 纳幕尔杜邦公司 | 用于丙交酯生产的高产率循环方法 |
CN1688569A (zh) * | 2002-08-06 | 2005-10-26 | 布鲁塞尔生物技术公司 | 以乳酸或其衍生物的溶液为原料制备聚交酯的方法 |
WO2010074222A1 (ja) * | 2008-12-26 | 2010-07-01 | 東レ株式会社 | 乳酸およびポリ乳酸の製造方法 |
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US20140323682A1 (en) | 2014-10-30 |
BR112014010481B1 (pt) | 2020-11-03 |
BR112014010481A2 (pt) | 2019-08-27 |
WO2013064219A3 (de) | 2013-07-18 |
EP2773683A2 (de) | 2014-09-10 |
ES2661638T3 (es) | 2018-04-02 |
KR20140108636A (ko) | 2014-09-12 |
EP2853552A1 (de) | 2015-04-01 |
PL2853552T3 (pl) | 2018-06-29 |
WO2013064219A2 (de) | 2013-05-10 |
EP2853552B1 (de) | 2017-12-06 |
KR101919647B1 (ko) | 2018-11-16 |
RU2631503C2 (ru) | 2017-09-25 |
MX355529B (es) | 2018-04-19 |
MX2014005254A (es) | 2015-10-29 |
CN104080833A (zh) | 2014-10-01 |
US9416222B2 (en) | 2016-08-16 |
RU2014118762A (ru) | 2015-12-10 |
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