TWI642478B - 包含金屬矽酸鹽材料及金屬離子之用於將糖轉化爲乳酸及２－羥基－３－丁烯酸或其酯類的方法 - Google Patents
包含金屬矽酸鹽材料及金屬離子之用於將糖轉化爲乳酸及２－羥基－３－丁烯酸或其酯類的方法 Download PDFInfo
- Publication number
- TWI642478B TWI642478B TW103128069A TW103128069A TWI642478B TW I642478 B TWI642478 B TW I642478B TW 103128069 A TW103128069 A TW 103128069A TW 103128069 A TW103128069 A TW 103128069A TW I642478 B TWI642478 B TW I642478B
- Authority
- TW
- Taiwan
- Prior art keywords
- metal
- group
- ions
- metal ion
- phthalate
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 67
- 229910021645 metal ion Inorganic materials 0.000 title claims abstract description 63
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 235000000346 sugar Nutrition 0.000 title claims abstract description 24
- VBWPSWWDYVWZKA-UHFFFAOYSA-N 2-hydroxybut-3-enoic acid Chemical compound C=CC(O)C(O)=O VBWPSWWDYVWZKA-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 239000004310 lactic acid Substances 0.000 title claims abstract description 12
- 235000014655 lactic acid Nutrition 0.000 title claims abstract description 12
- 150000002148 esters Chemical class 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 70
- 238000006243 chemical reaction Methods 0.000 title description 30
- 230000008569 process Effects 0.000 title description 24
- 150000008163 sugars Chemical class 0.000 title description 7
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 229910052914 metal silicate Inorganic materials 0.000 claims abstract description 8
- 239000011734 sodium Substances 0.000 claims abstract description 4
- 229910052751 metal Inorganic materials 0.000 claims description 71
- 239000002184 metal Substances 0.000 claims description 71
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 claims description 16
- 229940057867 methyl lactate Drugs 0.000 claims description 16
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical group C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052718 tin Inorganic materials 0.000 claims description 9
- 229930006000 Sucrose Natural products 0.000 claims description 8
- 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 8
- 239000005720 sucrose Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 239000008103 glucose Substances 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 229930091371 Fructose Natural products 0.000 claims description 5
- 239000005715 Fructose Substances 0.000 claims description 5
- 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 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 5
- 239000000956 alloy Substances 0.000 claims description 5
- 229910045601 alloy Inorganic materials 0.000 claims description 5
- 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 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
- 229910001414 potassium ion Inorganic materials 0.000 claims description 4
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- 238000001308 synthesis method Methods 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- 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 2
- YTBSYETUWUMLBZ-QWWZWVQMSA-N D-threose Chemical compound OC[C@@H](O)[C@H](O)C=O YTBSYETUWUMLBZ-QWWZWVQMSA-N 0.000 claims description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 2
- 229940116333 ethyl lactate Drugs 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 claims description 2
- 239000001521 potassium lactate Substances 0.000 claims description 2
- 235000011085 potassium lactate Nutrition 0.000 claims description 2
- 229960001304 potassium lactate Drugs 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 229910001422 barium ion Inorganic materials 0.000 claims 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- DQUIAMCJEJUUJC-UHFFFAOYSA-N dibismuth;dioxido(oxo)silane Chemical compound [Bi+3].[Bi+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O DQUIAMCJEJUUJC-UHFFFAOYSA-N 0.000 claims 1
- 229910001416 lithium ion Inorganic materials 0.000 claims 1
- 229910001415 sodium ion Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052700 potassium Inorganic materials 0.000 abstract description 3
- 239000011591 potassium Substances 0.000 abstract description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052744 lithium Inorganic materials 0.000 abstract description 2
- 229910052708 sodium Inorganic materials 0.000 abstract description 2
- 229910052788 barium Inorganic materials 0.000 abstract 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052712 strontium Inorganic materials 0.000 abstract 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 40
- 238000003786 synthesis reaction Methods 0.000 description 24
- 239000010457 zeolite Substances 0.000 description 21
- 229910021536 Zeolite Inorganic materials 0.000 description 19
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 14
- 239000007787 solid Substances 0.000 description 12
- 238000005470 impregnation Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000001354 calcination Methods 0.000 description 6
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 5
- 229910001413 alkali metal ion Inorganic materials 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002028 Biomass Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- -1 lactic acid derivative methyl lactate Chemical class 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 3
- 150000004645 aluminates Chemical class 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000011150 stannous chloride Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 3
- NYPNCQTUZYWFGG-UHFFFAOYSA-N 2,2-dimethoxyethanol Chemical compound COC(CO)OC NYPNCQTUZYWFGG-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000003893 lactate salts Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- JBKTVPSFVUFSAO-UHFFFAOYSA-N methyl 2-hydroxybut-3-enoate Chemical compound COC(=O)C(O)C=C JBKTVPSFVUFSAO-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000011833 salt mixture Substances 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 1
- VYQMXBMNWDFBHM-UHFFFAOYSA-K 2-hydroxypropane-1,2,3-tricarboxylate tetramethylazanium Chemical compound C[N+](C)(C)C.C[N+](C)(C)C.C[N+](C)(C)C.OC(CC([O-])=O)(CC([O-])=O)C([O-])=O VYQMXBMNWDFBHM-UHFFFAOYSA-K 0.000 description 1
- 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 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910020997 Sn-Y Inorganic materials 0.000 description 1
- 229910008859 Sn—Y Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000008238 biochemical pathway Effects 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- MKUWVMRNQOOSAT-UHFFFAOYSA-N but-3-en-2-ol Chemical compound CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- HMCVHEYVNMVFDP-UHFFFAOYSA-N ethyl 2-hydroxybut-3-enoate Chemical compound CCOC(=O)C(O)C=C HMCVHEYVNMVFDP-UHFFFAOYSA-N 0.000 description 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 238000005216 hydrothermal crystallization Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000005300 metallic glass Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012229 microporous material Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical group O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- KHMOASUYFVRATF-UHFFFAOYSA-J tin(4+);tetrachloride;pentahydrate Chemical compound O.O.O.O.O.Cl[Sn](Cl)(Cl)Cl KHMOASUYFVRATF-UHFFFAOYSA-J 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7049—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
- B01J29/7057—Zeolite Beta
-
- 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
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/085—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
- B01J29/088—Y-type faujasite
-
- 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
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7049—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/04—Mixing
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
- B01J37/10—Heat treatment in the presence of water, e.g. steam
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- 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
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/16—After treatment, characterised by the effect to be obtained to increase the Si/Al ratio; Dealumination
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ??13181069.9 | 2013-08-20 | ||
| EP13181069 | 2013-08-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201517983A TW201517983A (zh) | 2015-05-16 |
| TWI642478B true TWI642478B (zh) | 2018-12-01 |
Family
ID=48986058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW103128069A TWI642478B (zh) | 2013-08-20 | 2014-08-15 | 包含金屬矽酸鹽材料及金屬離子之用於將糖轉化爲乳酸及２－羥基－３－丁烯酸或其酯類的方法 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US9573123B2 (OSRAM) |
| EP (2) | EP3036040B1 (OSRAM) |
| JP (1) | JP6431913B2 (OSRAM) |
| KR (1) | KR101919030B1 (OSRAM) |
| CN (2) | CN105473227B (OSRAM) |
| BR (1) | BR112016003585B1 (OSRAM) |
| DK (1) | DK3036040T3 (OSRAM) |
| ES (1) | ES2657987T3 (OSRAM) |
| HU (1) | HUE036409T2 (OSRAM) |
| LT (1) | LT3036040T (OSRAM) |
| MX (1) | MX352954B (OSRAM) |
| NO (1) | NO3036040T3 (OSRAM) |
| PL (1) | PL3036040T3 (OSRAM) |
| SG (1) | SG11201600206SA (OSRAM) |
| SI (1) | SI3036040T1 (OSRAM) |
| TW (1) | TWI642478B (OSRAM) |
| WO (1) | WO2015024875A1 (OSRAM) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2968906C (en) | 2014-11-28 | 2023-09-12 | Haldor Topsoe A/S | Process for preparing esters of lactic acid, and 2-hydroxy-3-butenoic acid or alfa-hydroxy methionine analogues from sugars |
| CN107848822B (zh) | 2015-02-12 | 2021-03-02 | 巴斯夫欧洲公司 | 用于制备具有bea骨架结构的脱铝沸石材料的方法 |
| MX377376B (es) | 2015-04-30 | 2025-03-10 | Haldor Topsoe As | Un proceso para la preparacion de analogos alfa-hidroxilados de metionina a partir de azucares y derivados de los mismos. |
| US10315979B2 (en) * | 2015-06-18 | 2019-06-11 | Haldor Topsøe A/S | Preparation of 2,5,6-trihydroxy-3-hexenoic acid and 2,5-dihydroxy-3-pentenoic acid and esters thereof from C6 and C5 sugars |
| EP3106452A1 (en) | 2015-06-18 | 2016-12-21 | Haldor Topsøe A/S | Preparation of 2,5,6-trihydroxy-3-hexenoic acid and 2,5-dihydroxy-3-pentenoic acid and esters thereof from c6 and c5 sugars |
| US10252251B2 (en) * | 2015-08-28 | 2019-04-09 | Board Of Regents Of The Nevada System Of Higher Education, On Behalf Of The University Of Nevada, Reno | Production of organic materials using solid catalysts |
| ES2899827T3 (es) * | 2015-12-08 | 2022-03-14 | Basf Se | Material zeolítico que contiene estaño y que tiene una estructura de marco BEA |
| SE1600025A1 (en) * | 2016-01-28 | 2017-06-27 | Perstorp Ab | Radiation curing composition |
| KR20200119264A (ko) | 2018-02-09 | 2020-10-19 | 할도르 토프쉐 에이/에스 | 알파-하이드록시 화합물의 제조 과정 및 그것의 사용 |
| CN109289909B (zh) * | 2018-10-16 | 2021-03-19 | 郑州大学 | 一种催化复杂糖转化制备乳酸酯的催化剂 |
| CN111253249B (zh) * | 2018-11-30 | 2022-10-21 | 中国石油化工股份有限公司 | 一种制备乳酸酯的方法 |
| CN111116344B (zh) * | 2019-12-22 | 2021-08-31 | 上海交通大学 | 一种光催化转化单糖生物质制备乳酸的方法 |
| CN116199712A (zh) * | 2023-02-03 | 2023-06-02 | 嘉兴学院 | 一种金属-膦杂化材料及其制备方法与应用方法 |
| CN119524909A (zh) * | 2023-08-31 | 2025-02-28 | 中国石油化工股份有限公司 | 一种改性锡硅分子筛、制备方法及其应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110212187A1 (en) * | 2008-09-17 | 2011-09-01 | Taminco | Antimicrobial composition |
| EP2606968A2 (en) * | 2011-12-23 | 2013-06-26 | Rigas Tehniska universitate | Process for the preparation of lactic acid from glycerol |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4933161A (en) * | 1987-02-04 | 1990-06-12 | Exxon Research And Engineering Company | Tin substitution into zeolite frameworks |
| US5968473A (en) | 1998-12-18 | 1999-10-19 | Uop Llc | Stannosilicate molecular sieves |
| CN1175089C (zh) * | 2001-04-28 | 2004-11-10 | 中国石油化工股份有限公司 | 一种含分子筛的重整催化剂 |
| DE102004020259A1 (de) * | 2004-04-26 | 2005-11-10 | Hte Ag The High Throughput Experimentation Company | Oxidationskatalysator für die simultane Entfernung von Kohlenmonoxid und Kohlenwasserstoffen aus sauerstoffreichen Abgasen und Verfahren zu seiner Herstellung |
| PL2184270T3 (pl) | 2008-11-11 | 2013-07-31 | Haldor Topsoe As | Katalizowane zeolitem wytwarzanie związków alfa-hydroksykwasów karboksylowych i ich estrów |
| WO2011125882A1 (ja) * | 2010-03-31 | 2011-10-13 | 株式会社日本触媒 | 炭水化物含有原料から乳酸類を製造する方法 |
| US8987505B2 (en) | 2010-03-31 | 2015-03-24 | Nippon Shokubai Co., Ltd | Method for producing lactic acids from carbohydrate-containing raw material |
| CN103058869B (zh) * | 2013-02-01 | 2015-04-08 | 郑州大学 | 一种催化糖转化制备乳酸及乳酸酯的方法 |
-
2014
- 2014-08-15 LT LTEP14752847.5T patent/LT3036040T/lt unknown
- 2014-08-15 PL PL14752847T patent/PL3036040T3/pl unknown
- 2014-08-15 TW TW103128069A patent/TWI642478B/zh active
- 2014-08-15 BR BR112016003585-2A patent/BR112016003585B1/pt active IP Right Grant
- 2014-08-15 US US14/910,319 patent/US9573123B2/en active Active
- 2014-08-15 HU HUE14752847A patent/HUE036409T2/hu unknown
- 2014-08-15 MX MX2016001863A patent/MX352954B/es active IP Right Grant
- 2014-08-15 ES ES14752847.5T patent/ES2657987T3/es active Active
- 2014-08-15 DK DK14752847.5T patent/DK3036040T3/en active
- 2014-08-15 CN CN201480045946.8A patent/CN105473227B/zh active Active
- 2014-08-15 EP EP14752847.5A patent/EP3036040B1/en active Active
- 2014-08-15 NO NO14752847A patent/NO3036040T3/no unknown
- 2014-08-15 WO PCT/EP2014/067475 patent/WO2015024875A1/en not_active Ceased
- 2014-08-15 EP EP17193723.8A patent/EP3284535A1/en not_active Withdrawn
- 2014-08-15 JP JP2016535434A patent/JP6431913B2/ja active Active
- 2014-08-15 CN CN201810238215.5A patent/CN108465483A/zh active Pending
- 2014-08-15 KR KR1020167001535A patent/KR101919030B1/ko active Active
- 2014-08-15 SI SI201430568T patent/SI3036040T1/en unknown
- 2014-08-15 SG SG11201600206SA patent/SG11201600206SA/en unknown
-
2017
- 2017-02-17 US US15/435,758 patent/US9975113B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110212187A1 (en) * | 2008-09-17 | 2011-09-01 | Taminco | Antimicrobial composition |
| EP2606968A2 (en) * | 2011-12-23 | 2013-06-26 | Rigas Tehniska universitate | Process for the preparation of lactic acid from glycerol |
Also Published As
| Publication number | Publication date |
|---|---|
| MX352954B (es) | 2017-12-15 |
| LT3036040T (lt) | 2018-02-12 |
| US9975113B2 (en) | 2018-05-22 |
| PL3036040T3 (pl) | 2018-04-30 |
| SG11201600206SA (en) | 2016-02-26 |
| DK3036040T3 (en) | 2018-01-08 |
| US20160175822A1 (en) | 2016-06-23 |
| CN105473227A (zh) | 2016-04-06 |
| EP3284535A1 (en) | 2018-02-21 |
| BR112016003585B1 (pt) | 2020-12-01 |
| WO2015024875A1 (en) | 2015-02-26 |
| CN105473227B (zh) | 2018-04-27 |
| US20170173570A1 (en) | 2017-06-22 |
| TW201517983A (zh) | 2015-05-16 |
| JP6431913B2 (ja) | 2018-11-28 |
| NO3036040T3 (OSRAM) | 2018-04-07 |
| JP2016536324A (ja) | 2016-11-24 |
| EP3036040B1 (en) | 2017-11-08 |
| HUE036409T2 (hu) | 2018-07-30 |
| SI3036040T1 (en) | 2018-02-28 |
| CN108465483A (zh) | 2018-08-31 |
| KR101919030B1 (ko) | 2018-11-15 |
| BR112016003585A2 (pt) | 2018-05-02 |
| KR20160045675A (ko) | 2016-04-27 |
| EP3036040A1 (en) | 2016-06-29 |
| US9573123B2 (en) | 2017-02-21 |
| ES2657987T3 (es) | 2018-03-07 |
| MX2016001863A (es) | 2016-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI642478B (zh) | 包含金屬矽酸鹽材料及金屬離子之用於將糖轉化爲乳酸及２－羥基－３－丁烯酸或其酯類的方法 | |
| Jiang et al. | Direct catalytic conversion of carbohydrates to methyl levulinate: Synergy of solid Brønsted acid and Lewis acid | |
| Candu et al. | Efficient glucose dehydration to HMF onto Nb-BEA catalysts | |
| KR101848794B1 (ko) | 당의 이성화 방법 | |
| Iglesias et al. | Sn–Al-USY for the valorization of glucose to methyl lactate: switching from hydrolytic to retro-aldol activity by alkaline ion exchange | |
| KR20030043979A (ko) | 결정성 ｍｗｗ형 티타노실리케이트, 그 제조 방법 및 에폭사이드의 제조를 위한 그의 용도 | |
| ES2748690T3 (es) | Procedimiento para preparar ésteres de ácido láctico y ácido 2-hidroxi-3-butenoico a partir de azúcares | |
| Yang et al. | Conversion of glucose to methyl levulinate over Sn-Al-β zeolite: role of Sn and mesoporosity | |
| CN114105158A (zh) | 一种锡钛硅分子筛及其制备方法和应用 | |
| KR20170018308A (ko) | C1-3 옥시게네이트 화합물의 c4- 옥시게네이트 화합물로의 결정성 미소공성 물질 중재된 변환 | |
| TWI895612B (zh) | 一種生物質轉化製備對二甲苯的方法 | |
| CN109289909B (zh) | 一种催化复杂糖转化制备乳酸酯的催化剂 | |
| JP5788905B2 (ja) | 糖の異性化 | |
| CN112897547B (zh) | 一种快速合成无铝Sn-Beta分子筛的方法 | |
| WO2014174416A2 (en) | Dehydration of sugars on zeolites obtainable from an organotemplate-free synthetic process | |
| WO2003074463A1 (es) | Un procedimiento para la conversión de aldehidos usando un tamiz molecular y uso del tamiz molecular como catalizador en el procedimiento | |
| Tosi | Zeolite Catalysts for the Selective Conversion of Sugars into Polymer Monomers | |
| EP3106452A1 (en) | Preparation of 2,5,6-trihydroxy-3-hexenoic acid and 2,5-dihydroxy-3-pentenoic acid and esters thereof from c6 and c5 sugars | |
| CN119528726A (zh) | 一种羟醛缩合反应方法、催化材料和制备 | |
| CN119524909A (zh) | 一种改性锡硅分子筛、制备方法及其应用 | |
| JP2009136830A (ja) | Ｈ型メタロシリケート触媒の製造方法 | |
| CN120229736A (zh) | 一种基于局部结构重建方法制备Ti-Beta沸石的无氟无铝工艺 | |
| Conrad | Synthesis and Activity of Heterogeneous Lewis Acidic SnIV Catalysts | |
| Fan et al. | Rapid synthesis of beta zeolites | |
| JP2002193930A (ja) | ピロール類の製造方法 |