CN109988145B - 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
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- CN109988145B CN109988145B CN201910393379.XA CN201910393379A CN109988145B CN 109988145 B CN109988145 B CN 109988145B CN 201910393379 A CN201910393379 A CN 201910393379A CN 109988145 B CN109988145 B CN 109988145B
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- reaction
- vinyl sulfate
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- catalyst
- palladium
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- VEWLDLAARDMXSB-UHFFFAOYSA-N ethenyl sulfate;hydron Chemical compound OS(=O)(=O)OC=C VEWLDLAARDMXSB-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- 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 19
- 239000001301 oxygen Substances 0.000 claims abstract description 19
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- 239000007800 oxidant agent Substances 0.000 claims abstract description 17
- 230000001590 oxidative effect Effects 0.000 claims abstract description 13
- 238000001914 filtration Methods 0.000 claims abstract description 11
- 238000005406 washing Methods 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 66
- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 claims description 25
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 9
- 238000004519 manufacturing process Methods 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
- 238000001035 drying Methods 0.000 claims description 8
- 239000011949 solid catalyst Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 4
- 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 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical group Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- RBBXSUBZFUWCAV-UHFFFAOYSA-N ethenyl hydrogen sulfite Chemical compound OS(=O)OC=C RBBXSUBZFUWCAV-UHFFFAOYSA-N 0.000 abstract description 9
- 239000002351 wastewater Substances 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 4
- 230000002194 synthesizing effect Effects 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 238000004134 energy conservation Methods 0.000 abstract 1
- 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 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 239000003570 air Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 7
- 239000005708 Sodium hypochlorite Substances 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 6
- 208000012839 conversion disease Diseases 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 5
- 229940045803 cuprous chloride Drugs 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910000510 noble metal Inorganic materials 0.000 description 4
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 3
- YYPNNBPPDFTQFX-UHFFFAOYSA-N 2-thiophen-3-ylethanol Chemical compound OCCC=1C=CSC=1 YYPNNBPPDFTQFX-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 2
- 229910000367 silver sulfate Inorganic materials 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- JUDXOKKZTISQDJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 JUDXOKKZTISQDJ-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000002000 Electrolyte additive Substances 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
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 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
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 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
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- 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
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Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
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CN111533728B (zh) * | 2020-07-08 | 2020-10-13 | 东营市海科新源化工有限责任公司 | 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 |
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 |
CN115054937B (zh) * | 2022-06-27 | 2024-09-20 | 立海科技(江西)有限公司 | 一种用于硫酸乙烯酯的高品质升华结晶提纯装置 |
CN116535385A (zh) * | 2022-08-29 | 2023-08-04 | 苏州华一新能源科技股份有限公司 | 一种制备硫酸乙烯酯的方法 |
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 |
CN115806540B (zh) * | 2022-11-18 | 2024-08-30 | 荣成青木高新材料有限公司 | 一种亚硫酸乙烯酯的制备方法 |
CN116283894A (zh) * | 2023-02-23 | 2023-06-23 | 营口昌成新材料科技有限公司 | 一种硫酸乙烯酯的合成方法 |
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 |
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 |
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2019
- 2019-05-13 CN CN201910393379.XA patent/CN109988145B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
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