CN107032949A - 一种六氟丁二烯的纯化方法 - Google Patents
一种六氟丁二烯的纯化方法 Download PDFInfo
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- CN107032949A CN107032949A CN201610079360.4A CN201610079360A CN107032949A CN 107032949 A CN107032949 A CN 107032949A CN 201610079360 A CN201610079360 A CN 201610079360A CN 107032949 A CN107032949 A CN 107032949A
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- Prior art keywords
- hexachlorobutadiene
- adsorbent
- metal salt
- ion
- nitrate
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- RWNKSTSCBHKHTB-UHFFFAOYSA-N Hexachloro-1,3-butadiene Chemical compound ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl RWNKSTSCBHKHTB-UHFFFAOYSA-N 0.000 title claims abstract description 144
- 238000000746 purification Methods 0.000 title claims abstract description 20
- 239000003463 adsorbent Substances 0.000 claims abstract description 67
- 238000000034 method Methods 0.000 claims abstract description 43
- 238000001179 sorption measurement Methods 0.000 claims abstract description 20
- 238000005342 ion exchange Methods 0.000 claims abstract description 15
- 230000008569 process Effects 0.000 claims abstract description 15
- 238000001802 infusion Methods 0.000 claims abstract description 12
- 238000000498 ball milling Methods 0.000 claims abstract description 11
- 238000010521 absorption reaction Methods 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims description 44
- 229910052751 metal Inorganic materials 0.000 claims description 44
- 229910002651 NO3 Inorganic materials 0.000 claims description 27
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 27
- 239000007788 liquid Substances 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 22
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 20
- 239000012043 crude product Substances 0.000 claims description 20
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 18
- 239000002808 molecular sieve Substances 0.000 claims description 18
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 18
- 229910021645 metal ion Inorganic materials 0.000 claims description 17
- 239000012266 salt solution Substances 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- -1 alkenyl halide Chemical class 0.000 claims description 12
- 230000008929 regeneration Effects 0.000 claims description 7
- 238000011069 regeneration method Methods 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000012298 atmosphere Substances 0.000 claims description 5
- 238000005245 sintering Methods 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 229910052681 coesite Inorganic materials 0.000 claims description 4
- 229910052906 cristobalite Inorganic materials 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 229910052682 stishovite Inorganic materials 0.000 claims description 4
- 229910052905 tridymite Inorganic materials 0.000 claims description 4
- 230000000274 adsorptive effect Effects 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052593 corundum Inorganic materials 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 claims description 2
- 239000012535 impurity Substances 0.000 abstract description 43
- 239000000047 product Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000007789 gas Substances 0.000 description 14
- 239000002994 raw material Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LGPPATCNSOSOQH-UHFFFAOYSA-N 1,1,2,3,4,4-hexafluorobuta-1,3-diene Chemical compound FC(F)=C(F)C(F)=C(F)F LGPPATCNSOSOQH-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000007790 solid phase Substances 0.000 description 5
- 230000004913 activation Effects 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000007493 shaping process Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 2
- AYCANDRGVPTASA-UHFFFAOYSA-N 1-bromo-1,2,2-trifluoroethene Chemical group FC(F)=C(F)Br AYCANDRGVPTASA-UHFFFAOYSA-N 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- JLGADZLAECENGR-UHFFFAOYSA-N 1,1-dibromo-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Br)Br JLGADZLAECENGR-UHFFFAOYSA-N 0.000 description 1
- IGPWAITWXGQPMD-UHFFFAOYSA-N 1-fluorobuta-1,3-diene Chemical compound FC=CC=C IGPWAITWXGQPMD-UHFFFAOYSA-N 0.000 description 1
- BQHQZFUAEAVJRE-UHFFFAOYSA-N 2-fluorobuta-1,3-diene Chemical compound FC(=C)C=C BQHQZFUAEAVJRE-UHFFFAOYSA-N 0.000 description 1
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 1
- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- HUIOAUQSDRXHEQ-UHFFFAOYSA-M FC(F)=C(F)[Zn]Br Chemical compound FC(F)=C(F)[Zn]Br HUIOAUQSDRXHEQ-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- XGCTUKUCGUNZDN-UHFFFAOYSA-N [B].O=O Chemical compound [B].O=O XGCTUKUCGUNZDN-UHFFFAOYSA-N 0.000 description 1
- PRPAGESBURMWTI-UHFFFAOYSA-N [C].[F] Chemical compound [C].[F] PRPAGESBURMWTI-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Inorganic materials [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Description
杂质/原料 | 含量/ppmv |
三氟乙烯 | 600 |
三氟氯乙烯 | 1200 |
三氟溴乙烯 | 4400 |
七氟丁烯 | 4500 |
其它有机杂质 | 1500 |
H2O | 500 |
CO | 50 |
CO2 | 50 |
HF | 0.1 |
O2 | 300 |
N2 | 2000 |
六氟丁二烯 | 98.5% |
含量 | 实施例1 | 实施例2 | 实施例3 | 实施例4 | 实施例5 | 实施例6 | 实施例7 |
H2O/ppmv | 2.5 | 2 | 2 | 1.5 | 2 | 2.5 | 2 |
CO/ppmv | 3.5 | 1.6 | 0.2 | 0 | 0 | 0 | 0 |
CO2/ppmv | 1.5 | 1.9 | 0.7 | 0 | 0 | 0 | 0 |
HF/ppmv | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
O2/ppmv | 14.4 | 10.7 | 0.5 | 0.4 | 0.4 | 0.5 | 0.3 |
N2/ppmv | 23.1 | 15.4 | 1.7 | 0.9 | 1.1 | 1.3 | 1.1 |
Claims (10)
Priority Applications (1)
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CN201610079360.4A CN107032949B (zh) | 2016-02-04 | 2016-02-04 | 一种六氟丁二烯的纯化方法 |
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CN201610079360.4A CN107032949B (zh) | 2016-02-04 | 2016-02-04 | 一种六氟丁二烯的纯化方法 |
Publications (2)
Publication Number | Publication Date |
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CN107032949A true CN107032949A (zh) | 2017-08-11 |
CN107032949B CN107032949B (zh) | 2020-09-22 |
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Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108129256A (zh) * | 2017-12-29 | 2018-06-08 | 山东华安新材料有限公司 | 从2-氯-1,1,1,2-四氟丙烷中分离卤代烯烃杂质的方法 |
CN108623432A (zh) * | 2018-06-19 | 2018-10-09 | 宇极(廊坊)新材料有限公司 | 一种采用吸附-低温精馏法制备高纯六氟-1,3-丁二烯的工艺 |
CN109180424A (zh) * | 2017-12-29 | 2019-01-11 | 中国船舶重工集团公司第七八研究所 | 一种六氟丁二烯的纯化方法及纯化装置 |
CN110483234A (zh) * | 2019-08-29 | 2019-11-22 | 浙江博瑞电子科技有限公司 | 一种电子级八氟环戊烯的提纯方法 |
CN110526834A (zh) * | 2019-09-20 | 2019-12-03 | 北京宇极科技发展有限公司 | 一种制备高纯度全氟异丁腈的方法 |
CN111170888A (zh) * | 2020-01-02 | 2020-05-19 | 黎明化工研究设计院有限责任公司 | 一种提纯七氟异丁腈的方法 |
JP2020125356A (ja) * | 2020-05-12 | 2020-08-20 | ダイキン工業株式会社 | ヘキサフルオロブタジエンの製造方法 |
CN112266318A (zh) * | 2020-11-20 | 2021-01-26 | 苏州金宏气体股份有限公司 | 一种六氟-1,3-丁二烯分级提纯的方法 |
CN113105303A (zh) * | 2021-03-27 | 2021-07-13 | 上海化工研究院有限公司 | 一种六氟丁二烯的精制方法 |
CN113227024A (zh) * | 2018-12-28 | 2021-08-06 | 大金工业株式会社 | 六氟丁二烯的精制方法 |
US11097997B2 (en) | 2017-10-23 | 2021-08-24 | Daikin Industries, Ltd. | Method for producing hexafluorobutadiene |
CN113461569A (zh) * | 2021-08-02 | 2021-10-01 | 江苏扬农化工集团有限公司 | 一种6-氨基己腈的提纯方法及其采用的吸附剂的制备方法 |
CN113984949A (zh) * | 2021-11-05 | 2022-01-28 | 苏州金宏气体股份有限公司 | 一种六氟-1,3-丁二烯气体的酸度分析方法 |
CN114621050A (zh) * | 2020-12-10 | 2022-06-14 | 浙江蓝天环保高科技股份有限公司 | 一种脱除六氟丁二烯中含氟烯烃的方法 |
CN114713209A (zh) * | 2021-01-06 | 2022-07-08 | 浙江蓝天环保高科技股份有限公司 | 一种氟化物改性吸附剂及六氟-1,3-丁二烯粗品的纯化方法 |
CN115340438A (zh) * | 2021-05-14 | 2022-11-15 | 浙江蓝天环保高科技股份有限公司 | 一种高纯六氟丁二烯的提纯方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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RU2371229C2 (ru) * | 2007-08-02 | 2009-10-27 | Общество с ограниченной ответственностью "Пермская химическая компания" | Способ очистки гексафторбутадиена |
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2016
- 2016-02-04 CN CN201610079360.4A patent/CN107032949B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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RU2371229C2 (ru) * | 2007-08-02 | 2009-10-27 | Общество с ограниченной ответственностью "Пермская химическая компания" | Способ очистки гексафторбутадиена |
Cited By (24)
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---|---|---|---|---|
US11097997B2 (en) | 2017-10-23 | 2021-08-24 | Daikin Industries, Ltd. | Method for producing hexafluorobutadiene |
CN108129256A (zh) * | 2017-12-29 | 2018-06-08 | 山东华安新材料有限公司 | 从2-氯-1,1,1,2-四氟丙烷中分离卤代烯烃杂质的方法 |
CN109180424B (zh) * | 2017-12-29 | 2021-02-19 | 中船重工(邯郸)派瑞特种气体有限公司 | 一种六氟丁二烯的纯化方法及纯化装置 |
CN109180424A (zh) * | 2017-12-29 | 2019-01-11 | 中国船舶重工集团公司第七八研究所 | 一种六氟丁二烯的纯化方法及纯化装置 |
CN108623432A (zh) * | 2018-06-19 | 2018-10-09 | 宇极(廊坊)新材料有限公司 | 一种采用吸附-低温精馏法制备高纯六氟-1,3-丁二烯的工艺 |
CN113227024A (zh) * | 2018-12-28 | 2021-08-06 | 大金工业株式会社 | 六氟丁二烯的精制方法 |
CN110483234A (zh) * | 2019-08-29 | 2019-11-22 | 浙江博瑞电子科技有限公司 | 一种电子级八氟环戊烯的提纯方法 |
CN110483234B (zh) * | 2019-08-29 | 2021-12-07 | 浙江博瑞电子科技有限公司 | 一种电子级八氟环戊烯的提纯方法 |
CN110526834A (zh) * | 2019-09-20 | 2019-12-03 | 北京宇极科技发展有限公司 | 一种制备高纯度全氟异丁腈的方法 |
CN110526834B (zh) * | 2019-09-20 | 2022-05-20 | 泉州宇极新材料科技有限公司 | 一种制备高纯度全氟异丁腈的方法 |
CN111170888A (zh) * | 2020-01-02 | 2020-05-19 | 黎明化工研究设计院有限责任公司 | 一种提纯七氟异丁腈的方法 |
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JP7011197B2 (ja) | 2020-05-12 | 2022-01-26 | ダイキン工業株式会社 | ヘキサフルオロブタジエンの製造方法 |
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CN114621050A (zh) * | 2020-12-10 | 2022-06-14 | 浙江蓝天环保高科技股份有限公司 | 一种脱除六氟丁二烯中含氟烯烃的方法 |
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CN113105303A (zh) * | 2021-03-27 | 2021-07-13 | 上海化工研究院有限公司 | 一种六氟丁二烯的精制方法 |
CN115340438A (zh) * | 2021-05-14 | 2022-11-15 | 浙江蓝天环保高科技股份有限公司 | 一种高纯六氟丁二烯的提纯方法 |
CN113461569A (zh) * | 2021-08-02 | 2021-10-01 | 江苏扬农化工集团有限公司 | 一种6-氨基己腈的提纯方法及其采用的吸附剂的制备方法 |
CN113461569B (zh) * | 2021-08-02 | 2023-10-17 | 江苏扬农化工集团有限公司 | 一种6-氨基己腈的提纯方法及其采用的吸附剂的制备方法 |
CN113984949A (zh) * | 2021-11-05 | 2022-01-28 | 苏州金宏气体股份有限公司 | 一种六氟-1,3-丁二烯气体的酸度分析方法 |
CN113984949B (zh) * | 2021-11-05 | 2024-03-22 | 金宏气体股份有限公司 | 一种六氟-1,3-丁二烯气体的酸度分析方法 |
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