JP6980764B2 - 1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)とフッ化水素(HF)との共沸性又は共沸混合物様組成物 - Google Patents
1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)とフッ化水素(HF)との共沸性又は共沸混合物様組成物 Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims description 148
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 title claims description 85
- DYASWFAOCHPTRT-UHFFFAOYSA-N 1,3-dichloro-3,3-difluoroprop-1-ene Chemical group FC(F)(Cl)C=CCl DYASWFAOCHPTRT-UHFFFAOYSA-N 0.000 title claims description 41
- 238000009835 boiling Methods 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 23
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 50
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 17
- 239000007788 liquid Substances 0.000 description 14
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- 239000004088 foaming agent Substances 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 6
- 239000003380 propellant Substances 0.000 description 6
- 239000012808 vapor phase Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012025 fluorinating agent Substances 0.000 description 4
- 239000003507 refrigerant Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 description 2
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- FFTOUVYEKNGDCM-OWOJBTEDSA-N (e)-1,3,3-trifluoroprop-1-ene Chemical compound F\C=C\C(F)F FFTOUVYEKNGDCM-OWOJBTEDSA-N 0.000 description 1
- DYASWFAOCHPTRT-OWOJBTEDSA-N (e)-1,3-dichloro-3,3-difluoroprop-1-ene Chemical compound FC(F)(Cl)\C=C\Cl DYASWFAOCHPTRT-OWOJBTEDSA-N 0.000 description 1
- DYASWFAOCHPTRT-UPHRSURJSA-N (z)-1,3-dichloro-3,3-difluoroprop-1-ene Chemical compound FC(F)(Cl)\C=C/Cl DYASWFAOCHPTRT-UPHRSURJSA-N 0.000 description 1
- LDTMPQQAWUMPKS-UPHRSURJSA-N (z)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C/Cl LDTMPQQAWUMPKS-UPHRSURJSA-N 0.000 description 1
- IAHLQJBJZKIZIQ-UHFFFAOYSA-N 1,1,3,3-tetrachloro-1-fluoropropane Chemical compound FC(Cl)(Cl)CC(Cl)Cl IAHLQJBJZKIZIQ-UHFFFAOYSA-N 0.000 description 1
- GVVUPGXFVJLPDE-UHFFFAOYSA-N 1,3,3,3-tetrachloroprop-1-ene Chemical compound ClC=CC(Cl)(Cl)Cl GVVUPGXFVJLPDE-UHFFFAOYSA-N 0.000 description 1
- LAKXDZKIXFNBES-UHFFFAOYSA-N 1,3,3-trichloro-1,1-difluoropropane Chemical compound FC(F)(Cl)CC(Cl)Cl LAKXDZKIXFNBES-UHFFFAOYSA-N 0.000 description 1
- OPLWDQVQIWKMSG-UHFFFAOYSA-N 1-chloro-1-fluoropropane Chemical compound CCC(F)Cl OPLWDQVQIWKMSG-UHFFFAOYSA-N 0.000 description 1
- PLTIOZOVDUUXDQ-UHFFFAOYSA-N 3,3-dichloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)CC(Cl)Cl PLTIOZOVDUUXDQ-UHFFFAOYSA-N 0.000 description 1
- ZGOMEYREADWKLC-UHFFFAOYSA-N 3-chloro-1,1,1,3-tetrafluoropropane Chemical compound FC(Cl)CC(F)(F)F ZGOMEYREADWKLC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000010763 heavy fuel oil Substances 0.000 description 1
- 229940060367 inert ingredients Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010301 surface-oxidation reaction Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
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- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
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Description
7.2gの1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)を13.4gのHFと組み合わせて、−10℃及び7.1psiaで(目視観測では)不均質な共沸混合物混合物を形成した。底部の相(1232zdを多く含む層)の液体組成物もまた、サンプリング及び分析し、1.2重量%で存在するHFと、98.8重量%で存在する1232zdとを有することを見出した。
1232zdとHFとのみを含有する二成分の組成物をブレンドして、異なる組成物で不均質な共沸混合物混合物を形成した。混合物の蒸気圧を−10℃で測定し、その結果を以下の表1に示し、これは、約−10℃の一定温度でのHF重量パーセントの組成に相関する、1232zdとHFとの蒸気圧測定値を示している。
1232zdとHFとの共沸性組成物も形成し、次いで、蒸気−液−液平衡(VLLE)実験によって検証した。12.0gの1232zdを14.3gのHFと組み合わせて、−10℃で(目視観察では)不均質な混合物を形成した。混合物の蒸気組成物を−10℃の温度及び7.1psiaの圧力でサンプリングし、結果は、共沸性組成物が−10℃で約70+2重量%のHFであることを示し、混合物が−10℃の温度及び7.1psiaの圧力で不均質な共沸混合物であることが観察された。
本明細書は以下の発明の態様を包含する。
[1]
1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)と、フッ化水素(HF)と、から本質的になる、共沸性又は共沸混合物様組成物。
[2]
前記組成物が、前記フッ化水素(HF)と1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)とを組み合わせた重量に基づいて、約1〜約99重量%のフッ化水素(HF)と、約1〜約99重量%の1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)と、から本質的になる、[1]に記載の組成物。
[3]
前記組成物が、前記フッ化水素(HF)と1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)とを組み合わせた重量に基づいて、約2〜約99重量%のフッ化水素(HF)と、約1〜約98重量%の1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)と、から本質的になる、[1]に記載の組成物。
[4]
前記組成物が、前記フッ化水素(HF)と1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)とを組み合わせた重量に基づいて、約2〜約80重量%のフッ化水素(HF)と、約20〜約98重量%の1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)と、から本質的になる、[1]に記載の組成物。
[5]
前記組成物が、約7psia±1psiaの圧力で約−10℃±0.5℃の沸点を有する、[1]に記載の組成物。
[6]
前記フッ化水素(HF)と1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)とを組み合わせた重量に基づいて、約1〜約99重量%のフッ化水素(HF)と、約1〜約99重量%の1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)と、から本質的になる、ブレンドを形成することを含む、共沸性又は共沸混合物様組成物を形成する方法。
[7]
前記形成する工程が、前記フッ化水素(HF)と1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)とを組み合わせた重量に基づいて、約2〜約99重量%のフッ化水素(HF)と、約1〜約98重量%の1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)と、から本質的になる、ブレンドを形成することを含む、[6]に記載の方法。
[8]
前記形成する工程が、前記フッ化水素(HF)と1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)とを組み合わせた重量に基づいて、約2〜約80重量%のフッ化水素(HF)と、約20〜約98重量%の1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)と、から本質的になる、ブレンドを形成することを含む、[6]に記載の方法。
[9]
前記組成物が、約7psia±1psiaの圧力で約−10℃±0.5℃の沸点を有する、[6]に記載の方法。
[10]
1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)と、フッ化水素(HF)と、から本質的になる、共沸性又は共沸混合物様組成物を提供することと、
蒸気相の前記1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)の少なくとも一部を、フッ素化剤と反応させて、少なくとも1つのフッ素化有機化合物を生成することと、を含む、有機化合物をフッ素化するための方法。
Claims (3)
- 1〜99重量%の1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)と、1〜99重量%のフッ化水素(HF)と、から本質的になる、共沸性又は共沸混合物様組成物。
- 前記組成物が、7psia±1psiaの圧力で、−10℃±0.5℃の沸点を有する、請求項1に記載の組成物。
- 前記フッ化水素(HF)と1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)とを組み合わせた重量に基づいて、1〜99重量%のフッ化水素(HF)と、1〜99重量%の1,3−ジクロロ−3,3−ジフルオロプロプ−1−エン(HCFO−1232zd)と、から本質的になる、ブレンドを形成することを含む、共沸性又は共沸混合物様組成物を形成する方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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JP2021186792A JP7263489B2 (ja) | 2016-08-31 | 2021-11-17 | 1,3-ジクロロ-3,3-ジフルオロプロプ-1-エン(HCFO-1232zd)とフッ化水素(HF)との共沸性又は共沸混合物様組成物 |
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Application Number | Priority Date | Filing Date | Title |
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US15/252,544 | 2016-08-31 | ||
US15/252,544 US9950973B2 (en) | 2016-08-31 | 2016-08-31 | Azeotropic or azeotrope-like compositions of 1,3-dichloro-3,3-difluoroprop-1-ene (HCFO-1232zd) and hydrogen fluoride (HF) |
PCT/US2017/046946 WO2018044554A1 (en) | 2016-08-31 | 2017-08-15 | AZEOTROPIC OR AZEOTROPE-LIKE COMPOSITIONS OF 1,3-DICHLORO-3,3-DIFLUOROPROP-1-ENE (HCFO-1232zd) AND HYDROGEN FLUORIDE (HF) |
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JP2022028811A (ja) * | 2016-08-31 | 2022-02-16 | ハネウェル・インターナショナル・インコーポレーテッド | 1,3-ジクロロ-3,3-ジフルオロプロプ-1-エン(HCFO-1232zd)とフッ化水素(HF)との共沸性又は共沸混合物様組成物 |
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CN114249627B (zh) * | 2022-03-02 | 2022-05-20 | 北京宇极科技发展有限公司 | 一种制备e-1-氯-3,3,3-三氟丙烯的方法 |
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Cited By (2)
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JP2022028811A (ja) * | 2016-08-31 | 2022-02-16 | ハネウェル・インターナショナル・インコーポレーテッド | 1,3-ジクロロ-3,3-ジフルオロプロプ-1-エン(HCFO-1232zd)とフッ化水素(HF)との共沸性又は共沸混合物様組成物 |
JP7263489B2 (ja) | 2016-08-31 | 2023-04-24 | ハネウェル・インターナショナル・インコーポレーテッド | 1,3-ジクロロ-3,3-ジフルオロプロプ-1-エン(HCFO-1232zd)とフッ化水素(HF)との共沸性又は共沸混合物様組成物 |
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JP7263489B2 (ja) | 2023-04-24 |
CN109803946A (zh) | 2019-05-24 |
US20180057430A1 (en) | 2018-03-01 |
KR102650822B1 (ko) | 2024-03-26 |
CN109803946B (zh) | 2022-05-27 |
EP3507266A1 (en) | 2019-07-10 |
KR20190051955A (ko) | 2019-05-15 |
MX2019002232A (es) | 2019-06-10 |
JP2022028811A (ja) | 2022-02-16 |
US9950973B2 (en) | 2018-04-24 |
EP3507266A4 (en) | 2020-04-29 |
KR20240042187A (ko) | 2024-04-01 |
KR20230062882A (ko) | 2023-05-09 |
CN114686176A (zh) | 2022-07-01 |
WO2018044554A1 (en) | 2018-03-08 |
JP2019524859A (ja) | 2019-09-05 |
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