TW201546027A - 經由胺茴酸鹽製造苯胺 - Google Patents
經由胺茴酸鹽製造苯胺 Download PDFInfo
- Publication number
- TW201546027A TW201546027A TW104105211A TW104105211A TW201546027A TW 201546027 A TW201546027 A TW 201546027A TW 104105211 A TW104105211 A TW 104105211A TW 104105211 A TW104105211 A TW 104105211A TW 201546027 A TW201546027 A TW 201546027A
- Authority
- TW
- Taiwan
- Prior art keywords
- aniline
- fermentation
- distillation
- produced
- catalyst
- Prior art date
Links
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title claims abstract description 156
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 30
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 title claims description 103
- RWZYAGGXGHYGMB-UHFFFAOYSA-M anthranilate Chemical compound NC1=CC=CC=C1C([O-])=O RWZYAGGXGHYGMB-UHFFFAOYSA-M 0.000 claims abstract description 37
- 238000006114 decarboxylation reaction Methods 0.000 claims abstract description 31
- -1 anthranilate anion Chemical class 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- 238000004821 distillation Methods 0.000 claims abstract description 23
- 150000001768 cations Chemical class 0.000 claims abstract description 17
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims description 66
- 238000000855 fermentation Methods 0.000 claims description 59
- 230000004151 fermentation Effects 0.000 claims description 59
- 230000000813 microbial effect Effects 0.000 claims description 33
- 230000008569 process Effects 0.000 claims description 31
- 150000001412 amines Chemical class 0.000 claims description 29
- 239000010457 zeolite Substances 0.000 claims description 19
- 229910021536 Zeolite Inorganic materials 0.000 claims description 18
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 18
- 150000001450 anions Chemical class 0.000 claims description 14
- 239000002994 raw material Substances 0.000 claims description 13
- 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 claims description 12
- 238000000605 extraction Methods 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 241000894006 Bacteria Species 0.000 claims description 8
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 8
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 8
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 8
- 150000004043 trisaccharides Chemical class 0.000 claims description 8
- 241000588724 Escherichia coli Species 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 150000002016 disaccharides Chemical class 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 240000008042 Zea mays Species 0.000 claims description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 6
- 235000005822 corn Nutrition 0.000 claims description 6
- 239000008103 glucose Substances 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 241000186216 Corynebacterium Species 0.000 claims description 5
- 240000000111 Saccharum officinarum Species 0.000 claims description 5
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 5
- 241000209140 Triticum Species 0.000 claims description 5
- 235000021307 Triticum Nutrition 0.000 claims description 5
- 241000609240 Ambelania acida Species 0.000 claims description 4
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 4
- 241000186226 Corynebacterium glutamicum Species 0.000 claims description 4
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 4
- 241000196324 Embryophyta Species 0.000 claims description 4
- 229930091371 Fructose Natural products 0.000 claims description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 4
- 239000005715 Fructose Substances 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 4
- 229930006000 Sucrose Natural products 0.000 claims description 4
- 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 claims description 4
- 235000021536 Sugar beet Nutrition 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 4
- 239000010905 bagasse Substances 0.000 claims description 4
- 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 claims description 4
- 241000894007 species Species 0.000 claims description 4
- 239000008107 starch Substances 0.000 claims description 4
- 235000019698 starch Nutrition 0.000 claims description 4
- 239000010902 straw Substances 0.000 claims description 4
- 239000005720 sucrose Substances 0.000 claims description 4
- 239000002023 wood Substances 0.000 claims description 4
- 241001485655 Corynebacterium glutamicum ATCC 13032 Species 0.000 claims description 3
- 241000589516 Pseudomonas Species 0.000 claims description 3
- 241000589776 Pseudomonas putida Species 0.000 claims description 3
- 241000320117 Pseudomonas putida KT2440 Species 0.000 claims description 3
- 235000007238 Secale cereale Nutrition 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 229910003023 Mg-Al Inorganic materials 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229960001545 hydrotalcite Drugs 0.000 claims description 2
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 150000002772 monosaccharides Chemical class 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 claims 2
- 241000209056 Secale Species 0.000 claims 1
- 235000013399 edible fruits Nutrition 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000000243 solution Substances 0.000 description 19
- 241001302584 Escherichia coli str. K-12 substr. W3110 Species 0.000 description 17
- 239000000126 substance Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 12
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 10
- 239000002028 Biomass Substances 0.000 description 9
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 8
- 108090000623 proteins and genes Proteins 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229960004799 tryptophan Drugs 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
- 238000010353 genetic engineering Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960004050 aminobenzoic acid Drugs 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000012239 gene modification Methods 0.000 description 4
- 230000005017 genetic modification Effects 0.000 description 4
- 235000013617 genetically modified food Nutrition 0.000 description 4
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 229940069428 antacid Drugs 0.000 description 3
- 239000003159 antacid agent Substances 0.000 description 3
- 230000001458 anti-acid effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 238000012217 deletion Methods 0.000 description 3
- 230000037430 deletion Effects 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002773 nucleotide Substances 0.000 description 3
- 125000003729 nucleotide group Chemical group 0.000 description 3
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 101150100816 trpD gene Proteins 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000005956 Cosmos caudatus Nutrition 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 241000589774 Pseudomonas sp. Species 0.000 description 2
- 244000082988 Secale cereale Species 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical class O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- ZRAOWOQXOMXTQN-UHFFFAOYSA-N azanium;2-aminobenzoate Chemical compound [NH4+].NC1=CC=CC=C1C([O-])=O ZRAOWOQXOMXTQN-UHFFFAOYSA-N 0.000 description 2
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 2
- 229960003495 thiamine Drugs 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- ROQLQGQHEMKBKA-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1.NC1=CC=C(C(O)=O)C=C1 ROQLQGQHEMKBKA-UHFFFAOYSA-N 0.000 description 1
- ODEHMIGXGLNAKK-OESPXIITSA-N 6-kestotriose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 ODEHMIGXGLNAKK-OESPXIITSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 108030003596 Aminobenzoate decarboxylases Proteins 0.000 description 1
- 229910014497 Ca10(PO4)6(OH)2 Inorganic materials 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 241000206602 Eukaryota Species 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- 108091028043 Nucleic acid sequence Proteins 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- 229930003451 Vitamin B1 Natural products 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940064734 aminobenzoate Drugs 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- CYGKLLHTPPFPHH-UHFFFAOYSA-N aniline;hydrate Chemical compound O.NC1=CC=CC=C1 CYGKLLHTPPFPHH-UHFFFAOYSA-N 0.000 description 1
- JDGPQNJYYADFKP-UHFFFAOYSA-N aniline;n-phenylaniline Chemical compound NC1=CC=CC=C1.C=1C=CC=CC=1NC1=CC=CC=C1 JDGPQNJYYADFKP-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000011138 biotechnological process Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- ICSSIKVYVJQJND-UHFFFAOYSA-N calcium nitrate tetrahydrate Chemical compound O.O.O.O.[Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ICSSIKVYVJQJND-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 241000186254 coryneform bacterium Species 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002028 dodecanols Chemical class 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000003209 gene knockout Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 239000012510 hollow fiber Substances 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- SOXAGEOHPCXXIO-DVOMOZLQSA-N menthyl anthranilate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C1=CC=CC=C1N SOXAGEOHPCXXIO-DVOMOZLQSA-N 0.000 description 1
- 229960002248 meradimate Drugs 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 239000007003 mineral medium Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007523 nucleic acids Chemical group 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N para-methoxy benzoic acid Natural products COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004094 preconcentration Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000003077 quantum chemistry computational method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005059 solid analysis Methods 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000011691 vitamin B1 Substances 0.000 description 1
- 235000010374 vitamin B1 Nutrition 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/10—Magnesium; Oxides or hydroxides thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/90—Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
-
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14155937 | 2014-02-20 | ||
| EP14196431 | 2014-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201546027A true TW201546027A (zh) | 2015-12-16 |
Family
ID=52477814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW104105211A TW201546027A (zh) | 2014-02-20 | 2015-02-16 | 經由胺茴酸鹽製造苯胺 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10173969B2 (https=) |
| EP (2) | EP3470525B1 (https=) |
| KR (1) | KR102522515B1 (https=) |
| CN (1) | CN105992824B (https=) |
| BR (1) | BR112016019012B1 (https=) |
| CA (1) | CA2937844C (https=) |
| ES (2) | ES2808560T3 (https=) |
| HU (2) | HUE051416T2 (https=) |
| TW (1) | TW201546027A (https=) |
| WO (1) | WO2015124686A1 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102797879B1 (ko) | 2015-11-20 | 2025-04-22 | 코베스트로 도이칠란트 아게 | 아미노벤조산 또는 아미노벤조산 유도체의 제조 방법 |
| ES2965637T3 (es) * | 2015-12-18 | 2024-04-16 | Covestro Intellectual Property Gmbh & Co Kg | Procedimiento para la producción de ácido orto-aminobenzoico y/o anilina mediante levadura recombinante |
| US10703709B2 (en) | 2016-06-29 | 2020-07-07 | Covestro Deutschland Ag | Method for producing aniline or an aniline conversion product |
| CN109563028B (zh) | 2016-08-17 | 2021-11-19 | 科思创德国股份有限公司 | 在生产联合体中制备异氰酸酯和至少一种其他化学产品的方法 |
| US10968466B2 (en) | 2016-12-20 | 2021-04-06 | Covestro Deutschland Ag | Process for preparing aminobenzoic acid or an aminobenzoic acid conversion product |
| EP3694999B1 (en) * | 2017-10-12 | 2025-01-01 | Covestro Deutschland AG | Methods for increasing the tolerance of microbial cells towards anthranilic acid by limiting the amount of ammonia in the culture medium |
| CN112534057A (zh) | 2018-06-07 | 2021-03-19 | 科思创知识产权两合公司 | 制备氨基苯甲酸或氨基苯甲酸反应产物的方法 |
| BR112021001332B1 (pt) | 2018-07-27 | 2024-02-20 | Covestro Intellectual Property Gmbh & Co. Kg | Processo para preparar anilina ou um produto de conversão de anilina |
| EP4259685A1 (de) | 2020-12-10 | 2023-10-18 | Covestro Deutschland AG | Verfahren zur herstellung eines polyisocyanats, polyisocyanat, dessen verwendung und daraus hergestellte polyadditions¬produkte |
| EP4067409A1 (en) | 2021-04-01 | 2022-10-05 | Ems-Chemie Ag | Renewable cycloaliphatic diamines and polymers thereof |
| CN117396459A (zh) | 2021-06-02 | 2024-01-12 | 科思创德国股份有限公司 | 制备苯胺或苯胺衍生物的方法 |
| CN118541345A (zh) | 2021-12-20 | 2024-08-23 | 科思创德国股份有限公司 | 从水性母液中回收氨基苯甲酸的方法 |
| US20250223255A1 (en) | 2022-04-06 | 2025-07-10 | Covestro Deutschland Ag | Method for producing aniline or an aniline-derived product |
| WO2024003032A1 (de) | 2022-06-30 | 2024-01-04 | Covestro Deutschland Ag | Verfahren zur gewinnung von organischen säuren aus einer wässrigen mutterlauge |
| US11542223B1 (en) * | 2022-07-21 | 2023-01-03 | Covestro Llc | Process for preparing di- and polyamines of the diphenyl methane series |
| WO2025132393A1 (de) | 2023-12-19 | 2025-06-26 | Covestro Deutschland Ag | Herstellung von aminobenzoesäure |
| WO2025132390A1 (de) | 2023-12-19 | 2025-06-26 | Covestro Deutschland Ag | Verfahren umfassend die herstellung von aminobenzoesäure |
| WO2025132391A1 (de) | 2023-12-19 | 2025-06-26 | Covestro Deutschland Ag | Herstellung von aminobenzoesäure |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0594A (ja) * | 1991-04-19 | 1993-01-08 | Ajinomoto Co Inc | 発酵法によるアントラニル酸の製造法 |
| DE102005055189A1 (de) * | 2005-11-19 | 2007-05-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von 4,4'-Diphenylmethandiisocyanat |
| DE102006007619A1 (de) * | 2006-02-18 | 2007-08-23 | Bayer Materialscience Ag | Verfahren zur Herstellung von Anilin |
| RU2327683C2 (ru) * | 2006-05-04 | 2008-06-27 | Открытое акционерное общество "Химпром" | Способ рекуперации анилина |
| KR20180014240A (ko) * | 2009-10-23 | 2018-02-07 | 게노마티카 인코포레이티드 | 아닐린의 제조를 위한 미생물 |
| US20130302860A1 (en) * | 2010-12-28 | 2013-11-14 | Sumitomo Rubber Industries, Ltd. | Coryneform Bacterium Transformant and Process for Producing Aniline Using The Same |
| CN102154191B (zh) * | 2011-01-13 | 2012-09-26 | 北京赛诺百奥生物技术有限公司 | 产2s-甲基丙二酰辅酶a的假单胞工程菌 |
| WO2013103894A1 (en) * | 2012-01-05 | 2013-07-11 | Paromatics, Llc | Biological syntheisis of p-aminobenzoic acid, p-aminophenol, n-(4-hydroxyphenyl)ethanamide and derivatives thereof |
| JP2013230993A (ja) * | 2012-04-27 | 2013-11-14 | Teijin Ltd | アニリンの製造方法 |
-
2015
- 2015-02-16 TW TW104105211A patent/TW201546027A/zh unknown
- 2015-02-19 ES ES18203096T patent/ES2808560T3/es active Active
- 2015-02-19 CN CN201580008952.0A patent/CN105992824B/zh active Active
- 2015-02-19 CA CA2937844A patent/CA2937844C/en active Active
- 2015-02-19 BR BR112016019012-2A patent/BR112016019012B1/pt active IP Right Grant
- 2015-02-19 KR KR1020167022407A patent/KR102522515B1/ko active Active
- 2015-02-19 HU HUE18203096A patent/HUE051416T2/hu unknown
- 2015-02-19 EP EP18203096.5A patent/EP3470525B1/en active Active
- 2015-02-19 HU HUE15705035A patent/HUE041613T2/hu unknown
- 2015-02-19 WO PCT/EP2015/053524 patent/WO2015124686A1/en not_active Ceased
- 2015-02-19 US US15/120,163 patent/US10173969B2/en active Active
- 2015-02-19 ES ES15705035T patent/ES2713008T3/es active Active
- 2015-02-19 EP EP15705035.2A patent/EP3108001B1/en not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| HUE051416T2 (hu) | 2021-03-01 |
| KR20160124768A (ko) | 2016-10-28 |
| EP3108001A1 (en) | 2016-12-28 |
| EP3470525A1 (en) | 2019-04-17 |
| BR112016019012A2 (https=) | 2017-08-15 |
| BR112016019012B1 (pt) | 2023-11-28 |
| US20170066713A1 (en) | 2017-03-09 |
| CA2937844A1 (en) | 2015-08-27 |
| CN105992824A (zh) | 2016-10-05 |
| WO2015124686A1 (en) | 2015-08-27 |
| US10173969B2 (en) | 2019-01-08 |
| EP3108001B1 (en) | 2018-12-12 |
| CN105992824B (zh) | 2021-05-11 |
| HUE041613T2 (hu) | 2019-05-28 |
| EP3470525B1 (en) | 2020-05-13 |
| ES2713008T3 (es) | 2019-05-17 |
| CA2937844C (en) | 2022-05-03 |
| ES2808560T3 (es) | 2021-03-01 |
| KR102522515B1 (ko) | 2023-04-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW201546027A (zh) | 經由胺茴酸鹽製造苯胺 | |
| EP3108015B1 (en) | Recombinant strain producing o-aminobenzoate and fermentative production of aniline from renewable resources via 2-aminobenzoic acid | |
| EP2852676B1 (en) | A fermentation and simulated moving bed process | |
| CA2727549C (en) | Production of butanediol by anaerobic microbial fermentation | |
| EP2817411B1 (en) | Biotechnological method for producing butanol and butyric acid | |
| TW201243055A (en) | A fermentation process for controlling butanediol production | |
| US20100204526A1 (en) | Process for solvent production utilizing liquid phase adsorption | |
| Saha et al. | Production of bio-fuel (bio-ethanol) from biomass (pteris) by fermentation process with yeast | |
| CN109423452A (zh) | 一种利用工业废气中二氧化碳的发酵方法 | |
| Tran et al. | The production of xylitol by enzymatic hydrolysis of agricultural wastes | |
| CN105255854B (zh) | 可固定碳氧化物且可进行发酵反应的微生物及其制备方法与应用 | |
| BR112016011487A2 (pt) | Método de produção de 2,3-butanodiol | |
| Gloria et al. | Physiology of Ethanol Production by Yeasts | |
| BR112016019081B1 (pt) | Célula hospedeira microbiana recombinante e método para a produção de anilina | |
| CN104560841A (zh) | 一种重组大肠杆菌利用甘油生产3-羟基丁酮的方法 |