CN106748734A - A kind of method that organic acid is extracted from zymotic fluid - Google Patents
A kind of method that organic acid is extracted from zymotic fluid Download PDFInfo
- Publication number
- CN106748734A CN106748734A CN201510831612.XA CN201510831612A CN106748734A CN 106748734 A CN106748734 A CN 106748734A CN 201510831612 A CN201510831612 A CN 201510831612A CN 106748734 A CN106748734 A CN 106748734A
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- CN
- China
- Prior art keywords
- organic acid
- acid
- zymotic fluid
- ethylhexyls
- esters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000007524 organic acids Chemical class 0.000 title claims abstract description 88
- 238000000034 method Methods 0.000 title claims abstract description 40
- 239000012530 fluid Substances 0.000 title claims abstract description 34
- -1 ester compounds Chemical class 0.000 claims abstract description 72
- 238000000855 fermentation Methods 0.000 claims abstract description 40
- 230000004151 fermentation Effects 0.000 claims abstract description 40
- 239000000284 extract Substances 0.000 claims abstract description 38
- 238000000605 extraction Methods 0.000 claims abstract description 36
- 150000002148 esters Chemical class 0.000 claims abstract description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 125000005210 alkyl ammonium group Chemical group 0.000 claims abstract description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 8
- 239000001530 fumaric acid Substances 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 5
- 125000005270 trialkylamine group Chemical group 0.000 claims description 5
- 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 4
- 229920000305 Nylon 6,10 Polymers 0.000 claims description 4
- 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 abstract description 16
- 239000008103 glucose Substances 0.000 abstract description 16
- 239000000203 mixture Substances 0.000 abstract description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000004310 lactic acid Substances 0.000 description 17
- 235000014655 lactic acid Nutrition 0.000 description 17
- 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 15
- 238000011084 recovery Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 238000005119 centrifugation Methods 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- 244000005700 microbiome Species 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- HNBDQABBWNOTRU-UHFFFAOYSA-N thalline Chemical compound C1=CC=[Tl]C=C1 HNBDQABBWNOTRU-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- 108010011939 Pyruvate Decarboxylase Proteins 0.000 description 4
- 241000235347 Schizosaccharomyces pombe Species 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 238000010979 pH adjustment Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 2
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 108091008053 gene clusters Proteins 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229960005137 succinic acid Drugs 0.000 description 2
- 230000009261 transgenic effect Effects 0.000 description 2
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 1
- MTRYLAXNDGUFAK-UHFFFAOYSA-N 9-ethoxy-9-oxononanoic acid Chemical compound CCOC(=O)CCCCCCCC(O)=O MTRYLAXNDGUFAK-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 239000004251 Ammonium lactate Substances 0.000 description 1
- 241000722955 Anaerobiospirillum Species 0.000 description 1
- 241000186216 Corynebacterium Species 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 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
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 241000186660 Lactobacillus Species 0.000 description 1
- 241000192132 Leuconostoc Species 0.000 description 1
- 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 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 241000192001 Pediococcus Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 108010010974 Proteolipids Proteins 0.000 description 1
- 102000016202 Proteolipids Human genes 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- 241000194017 Streptococcus Species 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
- 238000002835 absorbance Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 239000003513 alkali Substances 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
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940059265 ammonium lactate Drugs 0.000 description 1
- 235000019286 ammonium lactate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 description 1
- 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 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 1
- LKKOGZVQGQUVHF-UHFFFAOYSA-N diethyl heptanedioate Chemical compound CCOC(=O)CCCCCC(=O)OCC LKKOGZVQGQUVHF-UHFFFAOYSA-N 0.000 description 1
- QMCVOSQFZZCSLN-QXMHVHEDSA-N dihexyl (z)-but-2-enedioate Chemical compound CCCCCCOC(=O)\C=C/C(=O)OCCCCCC QMCVOSQFZZCSLN-QXMHVHEDSA-N 0.000 description 1
- MJOKHGMXPJXFTG-UHFFFAOYSA-N dihexyl nonanedioate Chemical compound CCCCCCOC(=O)CCCCCCCC(=O)OCCCCCC MJOKHGMXPJXFTG-UHFFFAOYSA-N 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- XWVQUJDBOICHGH-UHFFFAOYSA-N dioctyl nonanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCC(=O)OCCCCCCCC XWVQUJDBOICHGH-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- XHEDLZYGAQSNTR-UHFFFAOYSA-N ethene;hexanedioic acid Chemical compound C=C.C=C.OC(=O)CCCCC(O)=O XHEDLZYGAQSNTR-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229940039696 lactobacillus Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical group 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- NFOGNXWLRIIVQL-UHFFFAOYSA-N n,n-dibutylundecan-1-amine Chemical compound CCCCCCCCCCCN(CCCC)CCCC NFOGNXWLRIIVQL-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- RECVMTHOQWMYFX-UHFFFAOYSA-N oxygen(1+) dihydride Chemical group [OH2+] RECVMTHOQWMYFX-UHFFFAOYSA-N 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical class CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The method of organic acid is extracted from zymotic fluid the present invention relates to a kind of, including by fermentation production of organic acid, obtains the 1st operation containing the thick liquid of organic acid that pH is 1~5；With with the Extraction medium containing ester compounds from, containing the organic acid is extracted in the thick liquid of organic acid, obtaining the 2nd operation of the extract solution containing the organic acid obtained by the 1st operation；The ester compounds are the diester compound of carbon number 10~30；The diester compound is the dialkyl ester of aliphatic dicarboxylic acid.By the combination of ester compounds and alkyl ammonium compounds, optionally, organic acid is efficiently obtained.That is, organic acid is selectively obtained with easy operation with can hardly extracting the composition (especially glucose) in zymotic fluid.
Description
Technical field
The present invention relates to organic acid field, specially a kind of efficiently method of the organic acid of extraction and application fermenting and producing from zymotic fluid.
Background technology
Current organic acid, such as lactic acid, butanedioic acid are used for the various uses such as medicine, agricultural chemicals, cosmetics.As the manufacture method of organic acid, fermentation method is used since ancient times.Generally, due to the organic acid of organic acid production bacterium production causes fermentation inhibitory, alkali is added to adjust to pH near neutrals while being fermented in zymotic fluid mostly.In this case, reclaimed organic acid as the salt of pH regulators.For example, lactic acid can be extracted as ammonium lactate using inorganic acid and alkylamine.But, because such pH adjusts trivial operations, in addition it is also necessary to the operation of organic acid is returned to from acylate, thus is more expensive to manufacture.Therefore, it is proposed to using by it is being fermented in acid condition, impart acid proof bacterium, such as acid resistance microorganism is fermented as the transformant of host.In this case, organic acid can be reclaimed with the form of acid.As the recovery method, it is known that the method for example extracted with the mixture of water-insoluble organic acid with non-water-soluble amine, the method extracted with oxygen-containing saturated heterocyclic formula compound, the method extracted with the solvent of azeotrope with water.In the 1st kind of method, it is set to mutually synthermal, it is necessary to use water-insoluble organic acid with anti-extraction to extract.The scope of the mixed proportion that must limit the organic acid and amine is additionally, since, and the scope must be changed according to manufactured organic acid, therefore it is unactual.In 2nd kind of method, tetrahydrofuran etc. is can be used as oxygen-containing saturated heterocyclic formula compound, but such hydrophilic solvent can also extract the hydroaropic substance beyond contained organic acid in zymotic fluid.In the 3rd kind of method, as the solvent of azeotrope with water, for example, the lower alcohols such as methyl alcohol, ethanol can be used, but these extraction alcohol must be largely removed in purification procedures, and also there is a problem of esterification.
The content of the invention
For the shortcoming of above-mentioned prior art, the present invention provides a kind of man-hour that pH adjustment need not be expended in fermentation procedure, in the absence of above-mentioned various problems, the manufacture method of the organic acid that can efficiently reclaim organic acid as purpose thing.
The present invention solves above-mentioned technical problem and uses following technical scheme：It is a kind of that the method for organic acid is extracted from zymotic fluid, including by fermentation production of organic acid, obtain the 1st operation containing the thick liquid of organic acid that pH is 1~5；With with the Extraction medium containing ester compounds from, containing the organic acid is extracted in the thick liquid of organic acid, obtaining the 2nd operation of the extract solution containing the organic acid obtained by the 1st operation.
Preferably, diester compound of the ester compounds for carbon number 10~30.
Preferably, dialkyl ester of the diester compound for aliphatic dicarboxylic acid.
Preferably, the diester compound is the diester compound selected from double (2- ethylhexyls) esters of fumaric acid, double (2- ethylhexyls) esters of decanedioic acid, double (2- ethylhexyls) esters of itaconic acid, double (2- ethylhexyls) esters of azelaic acid and double (2- ethylhexyls) esters of maleic acid.
Preferably, the Extraction medium also contains alkyl ammonium compounds.
Preferably, trialkylamine of the alkyl ammonium compounds for carbon number 15~39.
Preferably, the trialkylamine is selected from three hexyl amines, trioctylphosphine amine, three decyl amines.
Preferably, the volume ratio of the alkyl ammonium compounds/ester compounds in the Extraction medium is 0.6/1~9/1.
Preferably, also including extracting the organic acid from the extract solution using water, the 3rd operation of the extract solution containing the organic acid is obtained.
Preferably, the 3rd operation is carried out at 60~90 DEG C.
The present invention has the following advantages that compared with prior art：If using manufacture method of the invention, pH adjustment need not be carried out in fermentation procedure.Additionally, by the combination of ester compounds and alkyl ammonium compounds, optionally, being efficiently obtained organic acid.That is, organic acid is selectively obtained with easy operation with can hardly extracting the composition (especially glucose) in zymotic fluid.
Specific embodiment
In order that technological means, creation characteristic, reached purpose and effect that the present invention is realized are easy to understand, with reference to specific embodiment, the present invention is expanded on further.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, it is not intended to limit the present invention.
In the present invention, as long as organic compound of the organic acid with carboxyl, such as can enumerate lactic acid, 3- hydracrylic acids, pyruvic acid, malonic acid, butanedioic acid, malic acid, fumaric acid, maleic acid, glutaric acid and adipic acid etc..Wherein, from from the aspect of with extensive use, preferred lactic acid.These organic acids can be any one of D configurations, L-configuration, DL configurations, in addition it is also possible to be formed as oligomer, i.e. the polymer of the degree of polymerization 2~15 or so.
The fermentation of the 1st operation can be the homofermentation for only producing the organic acid, or the heterofermentation that ethanol etc. is also produced beyond the organic acid if producing organic acid using microorganism, then.Microorganism can be any one of wild type and transgenic.As wild-type microorganisms, for example, can enumerate the lactic acid fermenting bacterias such as streptococcus, Pediococcus, Leuconostoc and lactobacillus；The succinate fermentative bacterium such as Anaerobiospirillum and Corynebacterium.
As transgenic microorganism, transgenosis production of lactic acid yeast can be enumerated, for example using schizosaccharomyces pombe as host, it is integrated into lactate dehydrogenase gene, and make the gene cluster excalation of the encoding pyruvate decarboxylases of the host or the transformant of inactivation, the acid resistance such as yeast using saccharomyces microorganism is used as host, the transformant of the gene of encoding lactate dehydrogenase has been imported in the acid resistance microorganism, and the gene of encoding lactate dehydrogenase has been imported, and make the gene delection of encoding pyruvate decarboxylases 1 or saccharomyces cerevisiae for having inactivated etc..Wherein, from can by pH adjust near neutral, can with high productivity production lactic acid from the aspect of, it is preferred that using schizosaccharomyces pombe as host, being integrated into lactate dehydrogenase gene, and make the gene cluster excalation of the encoding pyruvate decarboxylases of the host or the transformant of inactivation.To fermenting, used zymotic fluid is not particularly limited, as long as basic inorganic salt class and the carbon source such as Na, K of production containing suitable purpose organic acid.Additionally, the compositions such as nitrogen source and amino acid can also be contained as needed.Zymotic fluid can be any one of natural, synthesis or semi-synthetic zymotic fluid.As carbon source, for example, can enumerate the sugar such as glucose, fructose, sucrose, maltose.As nitrogen source, for example, can enumerate ammonium salt, peptone, casamino acid, yeast extract of the inorganic acids such as ammonia, ammonium chloride, ammonium acetate or organic acid etc..As inorganic salts, for example, can enumerate magnesium phosphate, magnesium sulfate, sodium chloride, potassium dihydrogen phosphate etc..In addition, fermentation promotive factor such as proteolipid etc. can be blended.
As sugar, glucose is preferably used.Concentration of glucose in the zymotic fluid (100 mass %) at fermentation initial stage is preferably more than 1 mass %, more preferably 1~25 mass %, further preferred 2~16 mass %.Because fermentation causes concentration of glucose to decline, preferably it is added as needed on glucose to continue fermentation.The concentration of glucose in fermentation latter stage can be in below 1 mass %.Additionally, in the case where organic acid is separated while making fermentation liquid circulation be continuously fermented, preferably maintaining above-mentioned concentration of glucose.It is set to more than 2 mass % by by concentration of glucose, the productivity of organic acid can be improved.Additionally, being set to below 16 mass % by by the glucose in zymotic fluid, the production efficiency of organic acid is can further improve.
Additionally, in order to improve productivity, preferably carrying out high density fermentation.In high density fermentation, the initial cell concentration of the transformant in zymotic fluid is represented with drying thalline weight scaled value and is preferably set to 0.1~50g/L, is more preferably set to 0.2~40g/L.High productivity can be in a short time realized by improving initial cell concentration.Additionally, be possible to produce if initial cell concentration is too high thalline aggegation and purification efficiency reduction the problems such as.In addition, the cell concentration that embodiment described later etc. shows is the value converted by the absorbance (OD660) of the light of the wavelength 660nm determined by Japan Spectroscopy Corporation Visible Ultraviolet Light-splitting device V550.OD=1 in 660nm, the 0.8g/L of 0.2g/L, wet weight equivalent to yeast drying weight.
Fermentation can for example be carried out using known fermentation process by circulating fermentation, stirring fermentation etc..Preferably 23~37 DEG C of fermentation temperature.Additionally, fermentation time can be determined suitably.Fermentation can be batch fermentation, or continuously ferment.For example, thalline can be separated from zymotic fluid after being fermented with batch fermentation, obtain the zymotic fluid containing organic acid.Additionally, in continuous fermentation method, such as the method operated below repetition continuously to be fermented can be enumerated；The operation is：Partial fermentation liquid is taken out from the fermentation tank in fermentation, while organic acid is separated from the zymotic fluid for taking out, glucose and new zymotic fluid will be added in remaining zymotic fluid after having separated organic acid and is returned to fermentation tank.By being continuously fermented, the productivity of organic acid is can further improve.
The pH containing the thick liquid of organic acid containing organic acid for being produced is 1~5, preferably 1.5~4, particularly preferred 1.5~3.5.In the manufacture method of organic acid of the invention, it is preferred to use even if organic acid causes pH step-downs to the accumulation of zymotic fluid, can not also carry out pH adjustment and produce the fermentation method of organic acid.I.e., it is preferred to use even if after the pH step-downs of zymotic fluid, it is also possible to manufacture the fermentation method of organic acid by continuing directly to continuously fermenting for fermentation.In the fermentation method, in order to improve the productivity of organic acid, even if preferably also continuing to fermentation after the pH of zymotic fluid is for less than 3.5.Especially, due to above-mentioned schizosaccharomyces pombe transformant acid-proof, the pH containing the zymotic fluid of organic acid that is produced can not be adjusted and continue fermentation.
In 2nd operation, purpose organic acid is extracted containing organic acid thick liquid containing organic acid from obtained by the 1st operation with the Extraction medium containing ester compounds, obtain extract solution (1).This contains the thick liquid of organic acid and can be directly used for extracting, but is separated thalline by the thalline separating treatment such as centrifugation or filtering preferably before extraction.As the example of the condition of centrifugation, in can enumerating 1000~5000G, 10~15 minutes.Additionally, as the condition of filtering, can enumerate and use the filter membrane of nominal 0.1~2 μm of mesh size.As the typical case's composition containing the thick liquid of organic acid, for example, contain 50~120g/L of organic acid, 0.5~20g/L of sugar, 1~20g/L of ethanol.As ester compounds, the aliphatic ester of carbon number 4~40 and at least one of aromatic ester are preferably selected from.If carbon number ester compounds within the above range, then due to possessing appropriate polarity and boiling point, therefore easily efficiently extracted, and be removed in easy operation behind.As the boiling point under the normal pressure of the ester compounds, preferably more than 250 DEG C.The upper limit of the boiling point is not particularly limited, and is typically less than 400 DEG C.But, boiling point under in the absence of normal pressure and in the case of only existing decomposition point, decomposition point is preferably more than 250 DEG C.
As the ester compounds in the present invention, in above-mentioned aliphatic ester and aromatic ester, preferred aliphat ester.That is, the residue of any one aliphatic compound of carboxylic acid residues and alcohol residue preferably in ester compounds.
Ester group quantity of the ester compounds in 1 molecule, is divided into monoester compound and petchem.Used as the ester compounds in the present invention, preferably ester group quantity is 2~4 petchem, more preferably diester compound.The aliphatic diester compound of particularly preferred carbon number 10~30.
As diester compound, the diester compound with 1 dicarboxylic acid residue and 2 monohydric alcohol residues can be enumerated, with 2 monocarboxylic acid residues and 1 diester compound of residue of dihydric alcohol etc..Can be any one in these diester compounds, the aliphatic diester compound more preferably with dicarboxylic acid residue and monohydric alcohol residue as the ester compounds in the present invention.Diester compound particularly preferably with saturation or unsaturated aliphatic dicarboxylic acid residue and alkanol residue.
Preferred ester compounds in the present invention are the aliphatic diester compound of carbon number 10~30, wherein more preferably having the aliphatic diester compound of saturation or unsaturated aliphatic dicarboxylic acid residue and alkanol residue (that is, alkyl).Additionally, the carbon number (including number of the carbon atom of carbonyl) of saturated aliphatic dicarboxylic acids residue is preferably 5~15, more preferably 6~12.The carbon number (including number of the carbon atom of carbonyl) of unsaturated aliphatic dicarboxylic acid residue is preferably 4~8, more preferably 4~6.The carbon number preferably 2~12, more preferably 6~10 of alkanol residue (that is, alkyl).
Specifically, diethylene adipate can for example be enumerated, diisononyl adipate, the different hendecane ester of adipic acid two, double (2- ethylhexyls) esters of adipic acid, pimelic acid diethylester, pimelic acid didecyl, di-n-octyl sebacate, double (2- ethylhexyls) esters of decanedioic acid, dibutyl sebacate, ethylazelaate, dioctyl azelate, double (2- ethylhexyls) esters of azelaic acid, dihexyl azelate, double (2- ethylhexyls) esters of dodecanedioic acid, dibutyl fumarate, dinonyl furmarate, double (2- ethylhexyls) esters of fumaric acid, dihexyl maleate, double (2- ethylhexyls) esters of maleic acid, itaconic acid dipropyl and double (2- ethylhexyls) esters of itaconic acid.
Wherein, the ester compounds of double (2- ethylhexyls) esters of fumaric acid, double (2- ethylhexyls) esters of decanedioic acid, double (2- ethylhexyls) esters of itaconic acid, double (2- ethylhexyls) esters of azelaic acid and double (2- ethylhexyls) esters of maleic acid are most preferably selected from.
Said extracted medium further preferably alkyl ammonium compounds.As alkyl ammonium compounds, preferably dialkyl amine compound or trialkylamine compound.As dialkyl amine compound, preferably with 2 compounds of the alkyl of carbon number 3~15.As trialkylamine compound, preferably with 3 compounds of the alkyl of carbon number 3~15.Multiple alkyl in 1 molecule of dialkyl amine compound or trialkylamine compound can be with difference.
If abovementioned alkyl amines, then the intermiscibility with above-mentioned ester compounds is good, can improve extraction efficiency of the ester compounds to purpose thing organic acid.Additionally, in the case where further the extraction by water described later is carried out, during also the organic acid is extracted water by without prejudice to.
As the boiling point under the normal pressure of the alkylamine, preferably more than 250 DEG C.The upper limit of the boiling point is not particularly limited, and is typically less than 400 DEG C.But, boiling point under in the absence of normal pressure and in the case of only existing decomposition point, decomposition point is preferably more than 250 DEG C.
More preferably use the trialkylamine of carbon number 15~39.Dibutyl undecyl amine, three amylamines, diamyl undecyl amine, three hexyl amines, trioctylphosphine amine, three nonyl amine, three (undecyl) amine, three decyl amines and tridodecylamine can for example be enumerated.Wherein it is most preferably selected from the alkyl ammonium compounds of three hexyl amines, trioctylphosphine amine, three decyl amines and tridodecylamine.
And with the case of ester compounds and alkyl ammonium compounds, their ratio is with the volume basis of alkyl ammonium compounds/ester compounds, preferably 0.6/1~9/1, more preferably 1/1~3/1.If extraction efficiency within the range, can be improved.
Extraction is carried out as follows：The thick liquid of organic acid and Extraction medium will be contained to be mixed at a temperature of preferably 0~40 DEG C, more preferably 0~30 DEG C, contacted.Volume ratio containing the thick liquid/Extraction medium of organic acid is 0.5/1~2/1, is preferably set to 0.8/1~1.2/1.Depending on extraction time is according to mixing, contacting efficiency, but generally can be 1 minute~10 minutes.
Extraction can be carried out by batch operation, it is also possible to be carried out by continuous operation.From extraction efficiency it is high, easily by the Energy suppression required for operation from the aspect of low-level, preferably operate continuously.As batch operation, oscillating operation, stirring operation etc. can be enumerated.As continuous operation, the towers such as plate column or packed column can be used to carry out cocurrent extraction or adverse current extraction.From improve extraction efficiency, easily by equipment miniaturization from the aspect of, preferably using packed column carries out adverse current extraction.
Depending on distribution coefficient in the extraction carried out by the Extraction medium is according to the organic acid and Extraction medium as object, but preferably more than 0.2, more preferably more than 0.3.Additionally, recovery rate preferably more than 20%, more preferably more than 25%.
As Extraction medium, and with the case of ester compounds and alkyl ammonium compounds, the distribution coefficient preferably more than 1.0, more preferably more than 1.4 in the extraction carried out by the Extraction medium.Additionally, recovery rate preferably more than 50%, more preferably more than 60%.
On the other hand, the recovery rate preferably less than 20% of the organic matter (such as ethanol) produced in the carbon source (such as glucose), fermentation contained by fermentation medium, more preferably less than 15%, further preferred less than 10%, particularly preferred less than 5%.
Extract solution (1) can be stayed etc. by steaming of depressurizing and remove Extraction medium, obtain organic acid.It is preferred that extracting the organic acid from extract solution (1) using water in the 3rd operation, the extract solution (2) containing organic acid is obtained.From from the aspect of the purity for easily improving the organic acid for finally giving, preferably salt is not contained in water.That is, can be as water ion exchange water, distilled water, pure water etc. any one.The extraction carried out by water is carried out preferably at 60~90 DEG C at more preferably 70~90 DEG C.It is 0.5/1~2/1 in the volume ratio of extract solution (1)/water, is extracted under conditions of preferably 0.8/1~1.2/1.Depending on extraction time is according to mixing, contacting efficiency, but generally can be 3 hours~6 hours.
As Extraction medium, and with the case of ester compounds and alkyl ammonium compounds, the distribution coefficient preferably more than 1.0, more preferably more than 1.4 in the extraction carried out by water.Additionally, recovery rate preferably more than 50%, more preferably more than 60%.
It is preferred that the 3rd operation is carried out continuously with the 2nd operation and is carried out but it is also possible to be batch-type.Water can be removed with vacuum distillation etc. by the extract solution (2) obtained by the 3rd operation, obtain organic acid.At this point it is possible to be purified using known method such as activated carbon treatment etc. to extract solution (2).
Embodiment is illustrated below, the present invention is described in detail.But, the invention is not limited in these embodiments.
Preparation containing the thick liquid of lactic acid：Using the transgenosis production of lactic acid yeast ASP2782 of prior art making (using schizosaccharomyces pombe as host, it is integrated into lactate dehydrogenase gene, and makes the transformant that the gene pdc-2 of the encoding pyruvate decarboxylases of the host lacks) carry out lactic fermentation.The transformant is inoculated with D12 fluid nutrient mediums (glucose 12%), its fermentation 20 hours is made under conditions of 32 DEG C of temperature, hunting speed 100rpm, can obtain the zymotic fluid (pH2.3) of lactic acid concn 85.7g/L.Centrifugation (12000G, 5 minutes) is implemented to the zymotic fluid, is obtained as the supernatant containing the thick liquid of lactic acid.
Embodiment 1~6
Extract solution (1)：To obtain containing the thick liquid of lactic acid and ester compounds with volume ratio 1：1 is mixed.The mixed liquor that will be obtained is vibrated 1 minute after being kept for 15 minutes at 25 DEG C, and organic phase and water phase are separated with centrifugation (3000G, 5 minutes).Water phase is removed, extract solution (1) is obtained.Efficient liquid phase chromatographic analysis (HPLC) legal system is passed through to the lactic acid concn in the extract solution (1)；Post：TOSOH Co., Ltd's system, is measured, and obtains recovery rate and extracts distribution coefficient.Additionally, in embodiment 1, the glucose and the recovery rate of ethanol obtained again by HPLC methods are respectively 2.3% and 14.8%.
Extract solution (2)：Addition and the ion exchange water of extract solution (1) same volume, after being stirred 5 hours at 80 DEG C, organic phase and water phase are separated with centrifugation in extract solution (1).Organic phase is removed, extract solution (2) is obtained.Lactic acid concn in the extract solution (2) is determined by HPLC methods, recovery rate is obtained and is extracted distribution coefficient.
Embodiment 7~12
Extract solution (1)：To obtain being mixed with volume ratio 5: 2: 3 containing the thick liquid of lactic acid, ester compounds and tri-n-octyl amine.The mixed liquor that will be obtained is vibrated 1 minute after being kept for 15 minutes at 25 DEG C, and organic phase and water phase are separated with centrifugation (3000G, 5 minutes).Water phase is removed, extract solution (1) is obtained.Lactic acid concn in the extract solution (1) is determined by HPLC methods, recovery rate is obtained and is extracted distribution coefficient.Additionally, in embodiment 7, the glucose and the recovery rate of ethanol obtained again by HPLC methods are respectively 3% and 5%.
Extract solution (2)：Addition and the ion exchange water of extract solution (1) same volume, after being stirred 5 hours at 80 DEG C, organic phase and water phase are separated with centrifugation in extract solution (1).Organic phase is removed, extract solution (2) is obtained.Lactic acid concn in the extract solution (2) is determined by HPLC methods, recovery rate is obtained and is extracted distribution coefficient.
General principle of the invention and principal character and advantages of the present invention has been shown and described above; it should be understood by those skilled in the art that; the present invention is not limited to the above embodiments; merely illustrating the principles of the invention described in above-described embodiment and specification; without departing from the spirit and scope of the present invention; various changes and modifications of the present invention are possible; these changes and improvements all fall within the protetion scope of the claimed invention, and the claimed scope of the invention is by appending claims and its equivalent thereof.
Claims (10)
1. it is a kind of from zymotic fluid extract organic acid method, it is characterised in that：Including by fermentation production of organic acid, obtaining the 1st operation containing the thick liquid of organic acid that pH is 1~5；With with the Extraction medium containing ester compounds from, containing the organic acid is extracted in the thick liquid of organic acid, obtaining the 2nd operation of the extract solution containing the organic acid obtained by the 1st operation.
2. according to claim 1 it is a kind of from zymotic fluid extract organic acid method, it is characterised in that：The ester compounds are the diester compound of carbon number 10~30.
3. according to claim 1 it is a kind of from zymotic fluid extract organic acid method, it is characterised in that：The diester compound is the dialkyl ester of aliphatic dicarboxylic acid.
4. according to claim 1 it is a kind of from zymotic fluid extract organic acid method, it is characterised in that：The diester compound is the diester compound selected from double (2- ethylhexyls) esters of fumaric acid, double (2- ethylhexyls) esters of decanedioic acid, double (2- ethylhexyls) esters of itaconic acid, double (2- ethylhexyls) esters of azelaic acid and double (2- ethylhexyls) esters of maleic acid.
5. according to claim 1 it is a kind of from zymotic fluid extract organic acid method, it is characterised in that：The Extraction medium also contains alkyl ammonium compounds.
6. according to claim 1 it is a kind of from zymotic fluid extract organic acid method, it is characterised in that：The alkyl ammonium compounds are the trialkylamine of carbon number 15~39.
7. according to claim 1 it is a kind of from zymotic fluid extract organic acid method, it is characterised in that：The trialkylamine is selected from three hexyl amines, trioctylphosphine amine, three decyl amines.
8. the method as any one of claim 5~7, it is characterised in that：The volume ratio of the alkyl ammonium compounds/ester compounds in the Extraction medium is 0.6/1~9/1.
9. the method as any one of claim 1~8, it is characterised in that：Also include extracting the organic acid from the extract solution using water, obtain the 3rd operation of the extract solution containing the organic acid.
10. method as claimed in claim 9, it is characterised in that：3rd operation is carried out at 60~90 DEG C.
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