CN109988145A - 一种硫酸乙烯酯的制备方法 - Google Patents
一种硫酸乙烯酯的制备方法 Download PDFInfo
- Publication number
- CN109988145A CN109988145A CN201910393379.XA CN201910393379A CN109988145A CN 109988145 A CN109988145 A CN 109988145A CN 201910393379 A CN201910393379 A CN 201910393379A CN 109988145 A CN109988145 A CN 109988145A
- Authority
- CN
- China
- Prior art keywords
- sulfuric acid
- vinyl ester
- acid vinyl
- preparation
- palladium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- VEWLDLAARDMXSB-UHFFFAOYSA-N ethenyl sulfate;hydron Chemical compound OS(=O)(=O)OC=C VEWLDLAARDMXSB-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 36
- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 claims abstract description 30
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
- 239000001301 oxygen Substances 0.000 claims abstract description 22
- 238000001914 filtration Methods 0.000 claims abstract description 12
- 239000007800 oxidant agent Substances 0.000 claims abstract description 10
- 230000001590 oxidative effect Effects 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 60
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 19
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 229910052763 palladium Inorganic materials 0.000 claims description 10
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 9
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 8
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical group COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 8
- 239000011949 solid catalyst Substances 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 230000008859 change Effects 0.000 claims description 5
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- -1 cyanophenyl palladium chlorides Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- UTRMBXSNRJHAAJ-UHFFFAOYSA-N diphenylphosphane;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1PC1=CC=CC=C1 UTRMBXSNRJHAAJ-UHFFFAOYSA-N 0.000 claims description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims 2
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 claims 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 claims 1
- 238000005406 washing Methods 0.000 abstract description 7
- 230000001681 protective effect Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 239000002351 wastewater Substances 0.000 abstract description 2
- 238000004134 energy conservation Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000000034 method Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 208000012839 conversion disease Diseases 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000002699 waste material Substances 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 4
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 238000012805 post-processing Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000001119 stannous chloride Substances 0.000 description 4
- 235000011150 stannous chloride Nutrition 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- 239000005708 Sodium hypochlorite Substances 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- YYPNNBPPDFTQFX-UHFFFAOYSA-N 2-thiophen-3-ylethanol Chemical compound OCCC=1C=CSC=1 YYPNNBPPDFTQFX-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- UPZVRQOMDANCRD-UHFFFAOYSA-N [S].C(C)(=O)OC=C Chemical compound [S].C(C)(=O)OC=C UPZVRQOMDANCRD-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- XCASEDBCMLBDON-UHFFFAOYSA-N C(C)(=O)OC=C.S(=O)(=O)(O)O Chemical compound C(C)(=O)OC=C.S(=O)(=O)(O)O XCASEDBCMLBDON-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- FXORZKOZOQWVMQ-UHFFFAOYSA-L dichloropalladium;triphenylphosphane Chemical compound Cl[Pd]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FXORZKOZOQWVMQ-UHFFFAOYSA-L 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- XDNDXYZWMMAEPS-UHFFFAOYSA-N silver sulfuric acid Chemical compound [Ag].OS(O)(=O)=O XDNDXYZWMMAEPS-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- AMGFNXDORNWAAC-UHFFFAOYSA-K sodium trichlororuthenium hypochlorite Chemical compound Cl[O-].[Na+].[Ru](Cl)(Cl)Cl AMGFNXDORNWAAC-UHFFFAOYSA-K 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/10—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms two oxygen atoms and one sulfur atom, e.g. cyclic sulfates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (10)
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111909129A (zh) * | 2020-09-03 | 2020-11-10 | 常熟市常吉化工有限公司 | 一种双氧水直接氧化制备环状硫酸酯的方法 |
CN111925352A (zh) * | 2020-07-09 | 2020-11-13 | 常州孚新睿科新材料有限公司 | 一种硫酸乙烯酯的合成方法 |
CN113683592A (zh) * | 2021-08-27 | 2021-11-23 | 江苏瀚康新材料有限公司 | 一种含硫酸乙烯酯的碳酸甲乙酯溶液的制备方法 |
WO2022007259A1 (zh) * | 2020-07-08 | 2022-01-13 | 山东海科新源材料科技股份有限公司 | 硫酸乙烯酯的制备方法 |
CN113979990A (zh) * | 2021-11-23 | 2022-01-28 | 山东鹏润新材料有限公司 | 一种亚硫酸酯的制备方法 |
CN114181191A (zh) * | 2021-12-22 | 2022-03-15 | 湖南阿斯达新材料有限公司 | 一种环状硫酸酯的合成方法 |
CN114907310A (zh) * | 2022-05-19 | 2022-08-16 | 湖南阿斯达新材料有限公司 | 环状硫酸酯的制备方法 |
CN115054937A (zh) * | 2022-06-27 | 2022-09-16 | 欧兴敏 | 一种用于硫酸乙烯酯的高品质升华结晶提纯装置 |
CN115322170A (zh) * | 2022-08-29 | 2022-11-11 | 苏州华一新能源科技股份有限公司 | 一种硫酸乙烯酯的制备方法 |
CN115611852A (zh) * | 2022-11-01 | 2023-01-17 | 山东师范大学 | 一种原位催化氧化合成硫酸乙烯酯的方法 |
CN115806540A (zh) * | 2022-11-18 | 2023-03-17 | 山东兴文工业技术研究院有限公司 | 一种亚硫酸乙烯酯的制备方法 |
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CN105481826A (zh) * | 2016-01-11 | 2016-04-13 | 烟台海川化学制品有限公司 | 一种硫酸亚乙酯的制备方法 |
CN106187989A (zh) * | 2016-07-26 | 2016-12-07 | 张家港瀚康化工有限公司 | 硫酸乙烯酯的制备方法 |
CN108822073A (zh) * | 2018-06-19 | 2018-11-16 | 辽宁科隆精细化工股份有限公司 | 一种硫酸乙烯酯的制备方法及其应用 |
CN109369609A (zh) * | 2018-11-02 | 2019-02-22 | 珠海市赛纬电子材料股份有限公司 | 一种硫酸乙烯酯的制备方法 |
CN109485633A (zh) * | 2018-12-06 | 2019-03-19 | 东营石大胜华新能源有限公司 | 一种硫酸乙烯酯的制备方法 |
CN109516971A (zh) * | 2018-11-26 | 2019-03-26 | 山东永浩新材料科技有限公司 | 一种电池级硫酸乙烯酯的合成方法 |
-
2019
- 2019-05-13 CN CN201910393379.XA patent/CN109988145B/zh active Active
Patent Citations (6)
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CN105481826A (zh) * | 2016-01-11 | 2016-04-13 | 烟台海川化学制品有限公司 | 一种硫酸亚乙酯的制备方法 |
CN106187989A (zh) * | 2016-07-26 | 2016-12-07 | 张家港瀚康化工有限公司 | 硫酸乙烯酯的制备方法 |
CN108822073A (zh) * | 2018-06-19 | 2018-11-16 | 辽宁科隆精细化工股份有限公司 | 一种硫酸乙烯酯的制备方法及其应用 |
CN109369609A (zh) * | 2018-11-02 | 2019-02-22 | 珠海市赛纬电子材料股份有限公司 | 一种硫酸乙烯酯的制备方法 |
CN109516971A (zh) * | 2018-11-26 | 2019-03-26 | 山东永浩新材料科技有限公司 | 一种电池级硫酸乙烯酯的合成方法 |
CN109485633A (zh) * | 2018-12-06 | 2019-03-19 | 东营石大胜华新能源有限公司 | 一种硫酸乙烯酯的制备方法 |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022007259A1 (zh) * | 2020-07-08 | 2022-01-13 | 山东海科新源材料科技股份有限公司 | 硫酸乙烯酯的制备方法 |
CN111925352A (zh) * | 2020-07-09 | 2020-11-13 | 常州孚新睿科新材料有限公司 | 一种硫酸乙烯酯的合成方法 |
CN111909129A (zh) * | 2020-09-03 | 2020-11-10 | 常熟市常吉化工有限公司 | 一种双氧水直接氧化制备环状硫酸酯的方法 |
CN113683592A (zh) * | 2021-08-27 | 2021-11-23 | 江苏瀚康新材料有限公司 | 一种含硫酸乙烯酯的碳酸甲乙酯溶液的制备方法 |
CN113979990A (zh) * | 2021-11-23 | 2022-01-28 | 山东鹏润新材料有限公司 | 一种亚硫酸酯的制备方法 |
CN114181191B (zh) * | 2021-12-22 | 2024-04-05 | 湖南阿斯达新材料有限公司 | 一种环状硫酸酯的合成方法 |
CN114181191A (zh) * | 2021-12-22 | 2022-03-15 | 湖南阿斯达新材料有限公司 | 一种环状硫酸酯的合成方法 |
CN114907310A (zh) * | 2022-05-19 | 2022-08-16 | 湖南阿斯达新材料有限公司 | 环状硫酸酯的制备方法 |
CN114907310B (zh) * | 2022-05-19 | 2024-04-05 | 湖南阿斯达新材料有限公司 | 环状硫酸酯的制备方法 |
CN115054937A (zh) * | 2022-06-27 | 2022-09-16 | 欧兴敏 | 一种用于硫酸乙烯酯的高品质升华结晶提纯装置 |
CN115322170A (zh) * | 2022-08-29 | 2022-11-11 | 苏州华一新能源科技股份有限公司 | 一种硫酸乙烯酯的制备方法 |
CN115322170B (zh) * | 2022-08-29 | 2023-06-02 | 苏州华一新能源科技股份有限公司 | 一种硫酸乙烯酯的制备方法 |
CN115611852A (zh) * | 2022-11-01 | 2023-01-17 | 山东师范大学 | 一种原位催化氧化合成硫酸乙烯酯的方法 |
CN115611852B (zh) * | 2022-11-01 | 2023-11-10 | 山东师范大学 | 一种原位催化氧化合成硫酸乙烯酯的方法 |
CN115806540A (zh) * | 2022-11-18 | 2023-03-17 | 山东兴文工业技术研究院有限公司 | 一种亚硫酸乙烯酯的制备方法 |
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