CN110950736A - 一种金属有机产物水解制备醇类物质的工艺 - Google Patents
一种金属有机产物水解制备醇类物质的工艺 Download PDFInfo
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- CN110950736A CN110950736A CN201911240138.8A CN201911240138A CN110950736A CN 110950736 A CN110950736 A CN 110950736A CN 201911240138 A CN201911240138 A CN 201911240138A CN 110950736 A CN110950736 A CN 110950736A
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- Prior art keywords
- metal organic
- bicarbonate
- solid
- hydrolysis
- water
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- 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.)
- Granted
Links
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 52
- 239000002184 metal Substances 0.000 title claims abstract description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- 230000003301 hydrolyzing effect Effects 0.000 title claims abstract description 13
- 239000000126 substance Substances 0.000 title claims description 16
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 53
- 239000000243 solution Substances 0.000 claims abstract description 48
- 230000007062 hydrolysis Effects 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 38
- 239000002351 wastewater Substances 0.000 claims abstract description 35
- 239000007787 solid Substances 0.000 claims abstract description 32
- 239000007864 aqueous solution Substances 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 17
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 150000001298 alcohols Chemical class 0.000 claims abstract description 10
- 235000019476 oil-water mixture Nutrition 0.000 claims abstract description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000000926 separation method Methods 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 51
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 16
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 13
- 239000011575 calcium Substances 0.000 claims description 12
- 229910052791 calcium Inorganic materials 0.000 claims description 12
- 229910052744 lithium Chemical group 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 10
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical group [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 claims description 10
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 claims description 10
- 239000002370 magnesium bicarbonate Substances 0.000 claims description 10
- 235000014824 magnesium bicarbonate Nutrition 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000001569 carbon dioxide Substances 0.000 claims description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 claims description 6
- 229910000020 calcium bicarbonate Inorganic materials 0.000 claims description 6
- 150000004795 grignard reagents Chemical group 0.000 claims description 6
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 claims description 6
- 235000019198 oils Nutrition 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007818 Grignard reagent Substances 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 238000007086 side reaction Methods 0.000 abstract description 8
- 230000026030 halogenation Effects 0.000 abstract description 5
- 238000005658 halogenation reaction Methods 0.000 abstract description 5
- 125000004122 cyclic group Chemical group 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 description 16
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 13
- 239000001095 magnesium carbonate Substances 0.000 description 13
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 12
- 159000000003 magnesium salts Chemical class 0.000 description 11
- 238000003747 Grignard reaction Methods 0.000 description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 229910001629 magnesium chloride Inorganic materials 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 229940045997 vitamin a Drugs 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 4
- 229910052808 lithium carbonate Inorganic materials 0.000 description 4
- 239000005416 organic matter Substances 0.000 description 4
- 239000010865 sewage Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 3
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- -1 alkyl calcium Chemical compound 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- UYLUJGRCKKSWHS-UHFFFAOYSA-N prop-1-en-1-one Chemical compound CC=C=O UYLUJGRCKKSWHS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000019155 vitamin A Nutrition 0.000 description 2
- 239000011719 vitamin A Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 229910000032 lithium hydrogen carbonate Inorganic materials 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000001650 tertiary alcohol group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
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CN201911240138.8A CN110950736B (zh) | 2019-12-06 | 2019-12-06 | 一种金属有机产物水解制备醇类物质的工艺 |
PCT/CN2020/095633 WO2021109530A1 (zh) | 2019-12-06 | 2020-06-11 | 一种金属有机产物水解制备醇类物质的工艺 |
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CN201911240138.8A CN110950736B (zh) | 2019-12-06 | 2019-12-06 | 一种金属有机产物水解制备醇类物质的工艺 |
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CN110950736A true CN110950736A (zh) | 2020-04-03 |
CN110950736B CN110950736B (zh) | 2021-04-20 |
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WO (1) | WO2021109530A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021109530A1 (zh) * | 2019-12-06 | 2021-06-10 | 上虞新和成生物化工有限公司 | 一种金属有机产物水解制备醇类物质的工艺 |
CN114685338A (zh) * | 2022-04-08 | 2022-07-01 | 上虞新和成生物化工有限公司 | 一种维生素a醋酸酯的制备方法 |
Citations (4)
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---|---|---|---|---|
GB549352A (en) * | 1939-07-22 | 1942-11-18 | Bataafsche Petroleum | A process for the production of monohydric alcohols |
CN105541549A (zh) * | 2015-12-25 | 2016-05-04 | 上虞新和成生物化工有限公司 | 一种维生素a中间体的还原方法 |
CN106699510A (zh) * | 2016-12-28 | 2017-05-24 | 浙江新和成股份有限公司 | 一种格氏缩合反应的后处理方法 |
CN106748943B (zh) * | 2016-12-30 | 2018-03-02 | 厦门金达威维生素有限公司 | 一种维生素a中间体双格氏缩合物的连续水解中和的方法及装置 |
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CN102731269B (zh) * | 2012-07-04 | 2014-04-02 | 浙江中欣化工股份有限公司 | 一种4-甲氧基甲基-2,3,5,6-四氟苯甲醇的合成方法 |
CN106588584B (zh) * | 2015-10-14 | 2019-04-16 | 上虞新和成生物化工有限公司 | 一种醚类溶剂的除水方法 |
CN107513006B (zh) * | 2017-08-30 | 2020-06-12 | 上虞新和成生物化工有限公司 | 一种维生素a中间体c20醇的制备方法 |
CN107739390B (zh) * | 2017-09-29 | 2019-08-20 | 上虞新和成生物化工有限公司 | 一种虾青素中间体的合成方法 |
CN110304990B (zh) * | 2019-05-29 | 2022-10-25 | 南京瑞鼎生物医药有限公司 | 一种生产乙烯基β-紫罗兰醇的绿色工艺 |
CN110950736B (zh) * | 2019-12-06 | 2021-04-20 | 上虞新和成生物化工有限公司 | 一种金属有机产物水解制备醇类物质的工艺 |
-
2019
- 2019-12-06 CN CN201911240138.8A patent/CN110950736B/zh active Active
-
2020
- 2020-06-11 WO PCT/CN2020/095633 patent/WO2021109530A1/zh active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB549352A (en) * | 1939-07-22 | 1942-11-18 | Bataafsche Petroleum | A process for the production of monohydric alcohols |
CN105541549A (zh) * | 2015-12-25 | 2016-05-04 | 上虞新和成生物化工有限公司 | 一种维生素a中间体的还原方法 |
CN106699510A (zh) * | 2016-12-28 | 2017-05-24 | 浙江新和成股份有限公司 | 一种格氏缩合反应的后处理方法 |
CN106748943B (zh) * | 2016-12-30 | 2018-03-02 | 厦门金达威维生素有限公司 | 一种维生素a中间体双格氏缩合物的连续水解中和的方法及装置 |
Non-Patent Citations (1)
Title |
---|
孙智勇: "《制药工艺操作与技术改进》", 30 March 1994 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021109530A1 (zh) * | 2019-12-06 | 2021-06-10 | 上虞新和成生物化工有限公司 | 一种金属有机产物水解制备醇类物质的工艺 |
CN114685338A (zh) * | 2022-04-08 | 2022-07-01 | 上虞新和成生物化工有限公司 | 一种维生素a醋酸酯的制备方法 |
CN114685338B (zh) * | 2022-04-08 | 2023-09-12 | 上虞新和成生物化工有限公司 | 一种维生素a醋酸酯的制备方法 |
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WO2021109530A1 (zh) | 2021-06-10 |
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