JPWO2021150801A5 - - Google Patents
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- JPWO2021150801A5 JPWO2021150801A5 JP2022543620A JP2022543620A JPWO2021150801A5 JP WO2021150801 A5 JPWO2021150801 A5 JP WO2021150801A5 JP 2022543620 A JP2022543620 A JP 2022543620A JP 2022543620 A JP2022543620 A JP 2022543620A JP WO2021150801 A5 JPWO2021150801 A5 JP WO2021150801A5
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- ene
- trifluoromethyl
- dichloro
- catalyst
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- 238000000034 method Methods 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 35
- 239000003054 catalyst Substances 0.000 claims description 15
- HAGBGMHQVQLMSY-UHFFFAOYSA-N ClC(C(F)(F)F)(CC(C(F)(F)F)Cl)C(F)(F)F Chemical compound ClC(C(F)(F)F)(CC(C(F)(F)F)Cl)C(F)(F)F HAGBGMHQVQLMSY-UHFFFAOYSA-N 0.000 claims description 14
- 238000003682 fluorination reaction Methods 0.000 claims description 13
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 11
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 239000003377 acid catalyst Substances 0.000 claims description 10
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical group [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 claims 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 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000012025 fluorinating agent Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 7
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 239000011651 chromium Substances 0.000 claims description 5
- HTXFNORGOSHHJJ-UHFFFAOYSA-N pent-2-ene Chemical compound CC[C]=CC HTXFNORGOSHHJJ-UHFFFAOYSA-N 0.000 claims description 5
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 5
- YVOASHYXFVSAQN-UHFFFAOYSA-N 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(Cl)(Cl)C(F)(F)F YVOASHYXFVSAQN-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- 239000010439 graphite Substances 0.000 claims description 4
- 229910002804 graphite Inorganic materials 0.000 claims description 4
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 claims description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 3
- -1 aluminum chlorofluoride Chemical compound 0.000 claims description 3
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical group F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims description 3
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 3
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 claims description 2
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 claims description 2
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 claims description 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- HBBBDGWCSBWWKP-UHFFFAOYSA-J tetrachloroantimony Chemical compound Cl[Sb](Cl)(Cl)Cl HBBBDGWCSBWWKP-UHFFFAOYSA-J 0.000 claims description 2
- IDYFACFOJYNFAX-UHFFFAOYSA-J tetrafluoroantimony Chemical compound F[Sb](F)(F)F IDYFACFOJYNFAX-UHFFFAOYSA-J 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 7
- OPUDNJOIACEIEI-OWOJBTEDSA-N (e)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene Chemical compound FC(F)(F)\C=C\C(F)(C(F)(F)F)C(F)(F)F OPUDNJOIACEIEI-OWOJBTEDSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- OPUDNJOIACEIEI-UPHRSURJSA-N (z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene Chemical compound FC(F)(F)\C=C/C(F)(C(F)(F)F)C(F)(F)F OPUDNJOIACEIEI-UPHRSURJSA-N 0.000 description 3
- 229910018287 SbF 5 Inorganic materials 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- CJMMVSNAJGAHDL-OWOJBTEDSA-N ClC(/C=C/C(F)(F)F)(C(F)(F)F)C(F)(F)F Chemical compound ClC(/C=C/C(F)(F)F)(C(F)(F)F)C(F)(F)F CJMMVSNAJGAHDL-OWOJBTEDSA-N 0.000 description 2
- ULVHNQXCWPYCIG-UHFFFAOYSA-N FC(C(=CC(C(F)(F)F)F)C(F)(F)F)(F)F Chemical compound FC(C(=CC(C(F)(F)F)F)C(F)(F)F)(F)F ULVHNQXCWPYCIG-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- ONECNMGGHBBFDP-UHFFFAOYSA-N 1,5,5,5-tetrafluoro-4-methylpent-2-ene Chemical compound FCC=CC(C)C(F)(F)F ONECNMGGHBBFDP-UHFFFAOYSA-N 0.000 description 1
- HCXRQZKOTOHZKP-UHFFFAOYSA-N FC(F)(F)C=C=C(C(F)(F)F)C(F)(F)F Chemical compound FC(F)(F)C=C=C(C(F)(F)F)C(F)(F)F HCXRQZKOTOHZKP-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Description
本発明をその詳細な説明と併せて説明してきたが、前述の説明は、添付の特許請求の範囲により定義される本発明の範囲を例示することを意図するものであり、限定するものではないことを理解すべきである。他の態様、利点、及び変更は、以下の特許請求の範囲内である。本発明の任意の特定の態様及び／又は実施形態に関して本明細書に記載される特徴のいずれも、本明細書に記載される本発明の任意の他の態様及び／又は実施形態の他の特徴のいずれかのうちの１つ以上と組み合わせることができ、組み合わせの適合性を確実にするために適宜変更することができることが、本発明に関連する当業者により理解されるべきである。そのような組み合わせは、本開示により企図される本発明の一部であるとみなされる。
以下、本明細書に記載の主な発明について列記する。
（１） 酸触媒の存在下でヘキサフルオロプロパ－１－エンを１，３，３，３－テトラフルオロプロパ－１－エンと反応させることを含む、（Ｅ）－１，１，１，４，５，５，５－ヘプタフルオロ－４－（トリフルオロメチル）ペンタ－２－エンを調製するプロセス。
（２） 前記酸触媒が、ルイス酸触媒である、（１）に記載のプロセス。
（３） 前記酸触媒が、強ルイス酸触媒である、（１）に記載のプロセス。
（４） 前記酸触媒が、ＳｂＦ5、クロロフッ化アルミニウム（ＡＣＦ）、及び塩化アルミニウムから選択される、（１）に記載のプロセス。
（５） 前記酸触媒が、ＳｂＦ5である、（１）に記載のプロセス。
（６） 前記反応が、約－３０℃～約１００℃の温度で実施される、（１）に記載のプロセス。
（７） 前記反応が、約２５℃～約７５℃の温度で実施される、（１）に記載のプロセス。
（８） 前記反応が、約４０℃～約６０℃の温度で実施される、（１）に記載のプロセス。
（９） 前記反応が、約１ａｔｍ～約２５ａｔｍの圧力で実施される、（１）に記載のプロセス。
（１０） 前記反応が、液相反応として実施される、（１）に記載のプロセス。
（１１） 前記プロセスが、追加の溶媒成分の非存在下で実施される、（１）に記載のプロセス。
（１２） 前記プロセスが、１，３，３，３－テトラフルオロプロパ－１－エンと反応させる前に、前記ヘキサフルオロプロパ－１－エンと前記酸触媒とを予混合して第１の混合物を形成することを含む、（１）に記載のプロセス。
（１３） 前記ヘキサフルオロプロパ－１－エンと前記酸触媒との混合が、液相中で実施される、（１２）に記載のプロセス。
（１４） 前記第１の混合物が、液体である、（１２）に記載のプロセス。
（１５） 前記予混合が、約１ａｔｍ～約２５ａｔｍの圧力で実施される、（１２）に記載のプロセス。
（１６） 前記１，３，３，３－テトラフルオロプロパ－１－エンを前記第１の混合物に添加し、それによって（Ｅ）－１，１，１，４，５，５，５－ヘプタフルオロ－４－（トリフルオロメチル）ペンタ－２－エンを形成することを更に含む、（１２）に記載のプロセス。
（１７） 触媒の存在下で２，４－ジクロロ－１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタンをフッ素化することを含む、（Ｅ）－１，１，１，４，５，５，５－ヘプタフルオロ－４－（トリフルオロメチル）ペンタ－２－エンを調製するプロセス。
（１８） 前記フッ素化が、フッ素化剤の存在下で前記２，４－ジクロロ－１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタンを反応させることを含む、（１７）に記載のプロセス。
（１９） １当量の前記２，４－ジクロロ－１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタンに基づいて、約６～約２５モル当量のフッ素化剤を使用する、（１８）に記載のプロセス。
（２０） 前記フッ素化剤が、フッ化水素、三フッ化アンチモン、四フッ化アンチモン、五フッ化アンチモン、三塩化アンチモン／フッ化水素、四塩化アンチモン／フッ化水素、又はこれらの任意の混合物から選択される、（１８）に記載のプロセス。
（２１） 前記フッ素化が、液相フッ素化として実施される、（２０）に記載のプロセス。
（２２） 前記フッ素化が、約５０℃～約１５０℃の温度で実施される、（２１）に記載のプロセス。
（２３） 前記フッ素化が、約０ｐｓｉｇ～約６００ｐｓｉｇの圧力で実施される、（２１）に記載のプロセス。
（２４） 前記フッ素化剤が、フッ化水素である、（１８）に記載のプロセス。
（２５） 前記触媒が、クロム触媒である、（１８）に記載の方法。
（２６） 前記触媒が、オキシフッ化クロム、活性炭上のオキシフッ化クロム、グラファイト上のオキシフッ化クロム、フッ化物グラファイト上のオキシフッ化クロム、フッ化物アルミナ上のオキシフッ化クロム、酸化クロム、高表面積の酸化クロム、フッ素化アルミナ、及びフッ化物アルミナ上のクロム／ニッケルから選択される、（１８）に記載のプロセス。
（２７） 前記フッ素化が、気相フッ素化として実施される、（２６）に記載のプロセス。
（２８） 前記フッ素化が、約２００℃～約４００℃の温度で実施される、（２７）に記載のプロセス。
（２９） 前記フッ素化が、約０ｐｓｉｇ～約２００ｐｓｉｇの圧力で実施される、（２７）に記載のプロセス。
（３０） 前記触媒が、前記フッ素化の前に活性化される、（１８）に記載のプロセス。
（３１） 前記活性化が、第１の期間にわたって前記触媒を約３５０℃～約４００℃の温度に加熱することを含む、（３０）に記載のプロセス。
（３２） 前記第１の期間にわたる加熱が、窒素ガスの存在下で実施される、（３１）に記載のプロセス。
（３３） 前記活性化が、第２の期間にわたってフッ化水素の存在下で、前記触媒を約３５０℃～約４００℃の温度に加熱することを更に含む、（３１）に記載のプロセス。
（３４） 前記第２の期間にわたる加熱が、窒素、空気、又はこれらの混合物の存在下で実施される、（３３）に記載のプロセス。
（３５） 前記２，４－ジクロロ－１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタンが、鉄触媒及びトリアルキルホスフェートの存在下で２，２－ジクロロ－１，１，１，３，３，３－ヘキサフルオロプロパンを３，３，３－トリフルオロプロパ－１－エンと反応させることを含むプロセスに従って調製される、（１８）に記載のプロセス。
（３６） 前記鉄触媒が、鉄金属である、（３５）に記載のプロセス。
（３７） 前記トリアルキルホスフェートが、トリ（Ｃ1~6アルキル）ホスフェートである、（３５）に記載のプロセス。
（３８） 前記トリ（Ｃ1~6アルキル）ホスフェートが、リン酸トリブチルである、（３５）に記載のプロセス。
（３９） 前記反応が、約５０℃～約２５０℃の温度で実施される、（３５）に記載のプロセス。
（４０） 組成物であって、
（ｉ）（Ｅ）－１，１，１，４，５，５，５－ヘプタフルオロ－４－（トリフルオロメチル）ペンタ－２－エンと、
（ｉｉ）以下から選択される１つ以上の化合物：
（Ｚ）－１，１，１，４，５，５，５－ヘプタフルオロ－４－（トリフルオロメチル）ペンタ－２－エン、
ヘキサフルオロプロパ－１－エン、及び
１，３，３，３－テトラフルオロプロパ－１－エン
と、を含む、組成物。
（４１） 前記組成物が、約２～約３モルパーセントの（Ｚ）－１，１，１，４，５，５，５－ヘプタフルオロ－４－（トリフルオロメチル）ペンタ－２－エンを含む、（４０）に記載の組成物。
（４２） 前記組成物が、ＳｂＦ5を更に含む、（４０）に記載の組成物。
（４３） 組成物であって、
（ｉ）（Ｅ）－１，１，１，４，５，５，５－ヘプタフルオロ－４－（トリフルオロメチル）ペンタ－２－エンと、
（ｉｉ）以下から選択される１つ以上の化合物：
（Ｚ）－１，１，１，４，５，５，５－ヘプタフルオロ－４－（トリフルオロメチル）ペンタ－２－エン、
ヘキサフルオロプロパ－１－エン、及び
１，３，３，３－テトラフルオロプロパ－１－エン
と、を含み、
（１）に記載のプロセスに従って調製される、組成物。
（４４） 組成物であって、
（ｉ）（Ｅ）－１，１，１，４，５，５，５－ヘプタフルオロ－４－（トリフルオロメチル）ペンタ－２－エンと、
（ｉｉ）以下から選択される１つ以上の化合物：
１，１，１，４，５，５，５－ヘプタフルオロ－２－（トリフルオロメチル）ペンタ－２－エン、
（Ｅ）－４－クロロ－１，１，１，５，５，５－ヘキサフルオロ－４－（トリフルオロメチル）ペンタ－２－エン、及び
１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタ－２，３－ジエン
と、を含む、組成物。
（４５） 前記組成物が、２，４－ジクロロ－１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタンを更に含む、（４４）に記載の組成物。
（４６） 前記組成物が、フッ化水素、オキシフッ化クロム、又はこれらの組み合わせを更に含む、（４４）に記載の組成物。
（４７） 組成物であって、
（ｉ）（Ｅ）－１，１，１，４，５，５，５－ヘプタフルオロ－４－（トリフルオロメチル）ペンタ－２－エンと、
（ｉｉ）以下から選択される１つ以上の化合物：
１，１，１，４，５，５，５－ヘプタフルオロ－２－（トリフルオロメチル）ペンタ－２－エン、
（Ｅ）－４－クロロ－１，１，１，５，５，５－ヘキサフルオロ－４－（トリフルオロメチル）ペンタ－２－エン、
１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタ－２，３－ジエン、及び
２，４－ジクロロ－１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタン
と、を含み、
（１７）に記載のプロセスに従って調製される、組成物。
（４８） 組成物であって、
（ｉ）２，４－ジクロロ－１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタンと、
（ｉｉ）２，２－ジクロロ－１，１，１，３，３，３－ヘキサフルオロプロパン及び３，３，３－トリフルオロプロパ－１－エンから選択される１つ以上の化合物と、
を含む、組成物。
（４９） 前記組成物が、鉄金属、塩化鉄、リン酸トリブチル、又はこれらの任意の組み合わせを更に含む、（４８）に記載の組成物。
（５０） 組成物であって、
（ｉ）２，４－ジクロロ－１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタンと、
（ｉｉ）２，２－ジクロロ－１，１，１，３，３，３－ヘキサフルオロプロパン及び３，３，３－トリフルオロプロパ－１－エンから選択される１つ以上の化合物と、
を含み、
（３５）に記載のプロセスに従って調製される、組成物。
While the invention has been described in conjunction with a detailed description thereof, the foregoing description is intended to be illustrative of the scope of the invention as defined by the appended claims, and not to limit the scope of the invention. You should understand that. Other aspects, advantages, and modifications are within the scope of the following claims. Any of the features described herein with respect to any particular aspect and/or embodiment of the invention may be any other feature of any other aspect and/or embodiment of the invention described herein. It should be understood by those skilled in the art to which the present invention pertains that it can be combined with any one or more of the following, and can be modified accordingly to ensure compatibility of the combination. Such combinations are considered to be part of the invention contemplated by this disclosure.
The main inventions described in this specification will be listed below.
(1) (E)-1,1,1,4 comprising reacting hexafluoroprop-1-ene with 1,3,3,3-tetrafluoroprop-1-ene in the presence of an acid catalyst. , 5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene.
(2) The process according to (1), wherein the acid catalyst is a Lewis acid catalyst.
(3) The process according to (1), wherein the acid catalyst is a strong Lewis acid catalyst.
(4) The process according to (1), wherein the acid catalyst is selected from SbF 5 , aluminum chlorofluoride (ACF), and aluminum chloride.
(5) The process according to (1), wherein the acid catalyst is SbF 5 .
(6) The process of (1), wherein the reaction is conducted at a temperature of about -30°C to about 100°C.
(7) The process of (1), wherein the reaction is conducted at a temperature of about 25°C to about 75°C.
(8) The process of (1), wherein the reaction is conducted at a temperature of about 40°C to about 60°C.
(9) The process of (1), wherein the reaction is conducted at a pressure of about 1 atm to about 25 atm.
(10) The process according to (1), wherein the reaction is performed as a liquid phase reaction.
(11) The process according to (1), wherein the process is carried out in the absence of additional solvent components.
(12) The process includes premixing the hexafluoroprop-1-ene and the acid catalyst to form a first mixture before reacting with 1,3,3,3-tetrafluoroprop-1-ene. The process of (1), comprising forming.
(13) The process according to (12), wherein the mixing of the hexafluoroprop-1-ene and the acid catalyst is performed in a liquid phase.
(14) The process according to (12), wherein the first mixture is a liquid.
(15) The process of (12), wherein the premixing is performed at a pressure of about 1 atm to about 25 atm.
(16) adding the 1,3,3,3-tetrafluoroprop-1-ene to the first mixture, thereby producing (E)-1,1,1,4,5,5,5-hepta The process of (12) further comprising forming fluoro-4-(trifluoromethyl)pent-2-ene.
(17) (E)-1, comprising fluorinating 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane in the presence of a catalyst. , 1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene.
(18) The fluorination comprises reacting the 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane in the presence of a fluorinating agent. The process according to (17), comprising:
(19) About 6 to about 25 molar equivalents of fluorination based on 1 equivalent of the 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane. The process according to (18), using an agent.
(20) The fluorinating agent is hydrogen fluoride, antimony trifluoride, antimony tetrafluoride, antimony pentafluoride, antimony trichloride/hydrogen fluoride, antimony tetrachloride/hydrogen fluoride, or any mixture thereof. The process according to (18), selected from:
(21) The process according to (20), wherein the fluorination is performed as liquid phase fluorination.
(22) The process of (21), wherein the fluorination is performed at a temperature of about 50°C to about 150°C.
(23) The process of (21), wherein the fluorination is performed at a pressure of about 0 psig to about 600 psig.
(24) The process according to (18), wherein the fluorinating agent is hydrogen fluoride.
(25) The method according to (18), wherein the catalyst is a chromium catalyst.
(26) The catalyst is chromium oxyfluoride, chromium oxyfluoride on activated carbon, chromium oxyfluoride on graphite, chromium oxyfluoride on fluoride graphite, chromium oxyfluoride on fluoride alumina, chromium oxide, high surface area oxidation. The process according to (18), selected from chromium, fluorinated alumina, and chromium/nickel on fluoride alumina.
(27) The process according to (26), wherein the fluorination is performed as a gas phase fluorination.
(28) The process of (27), wherein the fluorination is performed at a temperature of about 200°C to about 400°C.
(29) The process of (27), wherein the fluorination is performed at a pressure of about 0 psig to about 200 psig.
(30) The process of (18), wherein the catalyst is activated prior to the fluorination.
31. The process of claim 30, wherein the activation includes heating the catalyst to a temperature of about 350° C. to about 400° C. for a first period of time.
(32) The process according to (31), wherein the heating for the first period is performed in the presence of nitrogen gas.
33. The process of claim 31, wherein the activation further comprises heating the catalyst to a temperature of about 350° C. to about 400° C. in the presence of hydrogen fluoride for a second period of time.
(34) The process according to (33), wherein the heating for the second period is performed in the presence of nitrogen, air, or a mixture thereof.
(35) The 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane is converted into 2,2-dichloro-2,2-dichloro-2-(trifluoromethyl)pentane in the presence of an iron catalyst and trialkyl phosphate. - The process according to (18), prepared according to a process comprising reacting 1,1,1,3,3,3-hexafluoropropane with 3,3,3-trifluoroprop-1-ene.
(36) The process according to (35), wherein the iron catalyst is iron metal.
(37) The process according to (35), wherein the trialkyl phosphate is tri(C 1-6 alkyl) phosphate.
(38) The process according to (35), wherein the tri(C 1-6 alkyl)phosphate is tributyl phosphate.
(39) The process of (35), wherein the reaction is carried out at a temperature of about 50°C to about 250°C.
(40) A composition,
(i) (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene;
(ii) one or more compounds selected from:
(Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene,
A composition comprising: hexafluoroprop-1-ene; and 1,3,3,3-tetrafluoroprop-1-ene.
(41) The composition comprises about 2 to about 3 mole percent (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene. The composition according to (40), comprising:
(42) The composition according to (40), further comprising SbF 5 .
(43) A composition,
(i) (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene;
(ii) one or more compounds selected from:
(Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene,
Hexafluoroprop-1-ene, and 1,3,3,3-tetrafluoroprop-1-ene,
A composition prepared according to the process described in (1).
(44) A composition,
(i) (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene;
(ii) one or more compounds selected from:
1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)pent-2-ene,
(E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)pent-2-ene, and 1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)pent-2-ene Fluoro-2-(trifluoromethyl)penta-2,3-diene.
(45) The composition according to (44), wherein the composition further contains 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane.
(46) The composition according to (44), wherein the composition further comprises hydrogen fluoride, chromium oxyfluoride, or a combination thereof.
(47) A composition,
(i) (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene;
(ii) one or more compounds selected from:
1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)pent-2-ene,
(E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)pent-2-ene,
1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)penta-2,3-diene, and 2,4-dichloro-1,1,1,5,5,5-hexa Fluoro-2-(trifluoromethyl)pentane,
A composition prepared according to the process described in (17).
(48) A composition,
(i) 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane;
(ii) one or more compounds selected from 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane and 3,3,3-trifluoroprop-1-ene;
A composition comprising.
(49) The composition according to (48), wherein the composition further comprises iron metal, iron chloride, tributyl phosphate, or any combination thereof.
(50) A composition,
(i) 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane;
(ii) one or more compounds selected from 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane and 3,3,3-trifluoroprop-1-ene;
including;
A composition prepared according to the process described in (35).
Claims (14)
１当量の前記２，４－ジクロロ－１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタンに基づいて、約６～約２５モル当量のフッ素化剤を使用する、請求項５に記載のプロセス。 the fluorination comprises reacting the 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane in the presence of a fluorinating agent;
From about 6 to about 25 molar equivalents of fluorinating agent are used, based on 1 equivalent of said 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane. 6. The process of claim 5.
（ｉ）２，４－ジクロロ－１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタンと、
（ｉｉ）２，２－ジクロロ－１，１，１，３，３，３－ヘキサフルオロプロパン及び３，３，３－トリフルオロプロパ－１－エンから選択される１つ以上の化合物と、
を含む、組成物。 A composition,
(i) 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane,
(ii) one or more compounds selected from 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane and 3,3,3-trifluoroprop-1-ene;
A composition comprising.
（ｉ）２，４－ジクロロ－１，１，１，５，５，５－ヘキサフルオロ－２－（トリフルオロメチル）ペンタンと、
（ｉｉ）２，２－ジクロロ－１，１，１，３，３，３－ヘキサフルオロプロパン及び３，３，３－トリフルオロプロパ－１－エンから選択される１つ以上の化合物と、
を含み、
請求項１１に記載のプロセスに従って調製される、組成物。 A composition,
(i) 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane,
(ii) one or more compounds selected from 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane and 3,3,3-trifluoroprop-1-ene;
including;
A composition prepared according to the process of claim 11.
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| US202062964674P | 2020-01-23 | 2020-01-23 | |
| US62/964,674 | 2020-01-23 | ||
| PCT/US2021/014486 WO2021150801A1 (en) | 2020-01-23 | 2021-01-22 | Synthesis of (e)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene |
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| CN116874345A (en) * | 2023-09-06 | 2023-10-13 | 北京宇极科技发展有限公司 | Method for the gas phase continuous production of E-1, 4, 5-heptafluoro-4- (trifluoromethyl) pent-2-ene |
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| US3258500A (en) | 1959-08-17 | 1966-06-28 | Du Pont | Process for fluorinating halohydro-carbons |
| US4828818A (en) | 1987-03-13 | 1989-05-09 | Allied-Signal Inc. | Chromium aerogel method of producing same and fluorinating process utilizing same |
| US5036036A (en) | 1989-06-13 | 1991-07-30 | E. I. Du Pont De Nemours And Company | Chromium oxide catalyst composition |
| FR2669022B1 (en) | 1990-11-13 | 1992-12-31 | Atochem | PROCESS FOR THE MANUFACTURE OF TETRAFLUORO-1,1,1,2-ETHANE. |
| US6156943A (en) * | 1997-11-21 | 2000-12-05 | E. I. Du Pont De Nemours And Company | Halogenated hydrocarbons containing fluorine and processes for their manufacture |
| KR20080050632A (en) * | 2005-11-10 | 2008-06-09 | 그레이트 레이크스 케미칼 코퍼레이션 | Fire extinguishing and fire suppression compositions comprising unsaturate flouorocarbon |
| RU2006139128A (en) | 2006-11-07 | 2008-05-20 | Е.И.Дюпон де Немур энд Компани (US) | METHOD FOR PRODUCING FLORATED OLEFINS |
| US8148548B2 (en) * | 2007-07-13 | 2012-04-03 | Konarka Technologies, Inc. | Heterocyclic fused selenophene monomers |
| US8461401B2 (en) * | 2010-03-26 | 2013-06-11 | Honeywell International Inc. | Method for making hexafluoro-2-butene |
| RU2010147004A (en) * | 2010-11-17 | 2012-05-27 | Е.И.Дюпон де Немур энд Компани (US) | CATALYTIC SYNTHESIS OF INTERNAL FLUORBUTENES AND INTERNAL FLUOROPENTENES |
| JP6641364B2 (en) * | 2014-10-30 | 2020-02-05 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | Use of (2E) -1,1,1,4,5,5,5-heptafluoro-4- (trifluoromethyl) penta-2-ene in a power cycle |
| CN109476567B (en) | 2016-07-27 | 2022-08-09 | 科慕埃弗西有限公司 | Process for producing halogenated olefins |
| EP3634931A4 (en) * | 2017-06-07 | 2020-12-23 | 3M Innovative Properties Company | Fluids for immersion cooling |
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