JP7132378B2 - 触媒およびこの触媒を用いるフッ素化炭化水素の製造プロセス - Google Patents
触媒およびこの触媒を用いるフッ素化炭化水素の製造プロセス Download PDFInfo
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- JP7132378B2 JP7132378B2 JP2021024682A JP2021024682A JP7132378B2 JP 7132378 B2 JP7132378 B2 JP 7132378B2 JP 2021024682 A JP2021024682 A JP 2021024682A JP 2021024682 A JP2021024682 A JP 2021024682A JP 7132378 B2 JP7132378 B2 JP 7132378B2
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- 238000000034 method Methods 0.000 title claims description 55
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- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 18
- 238000002459 porosimetry Methods 0.000 claims description 17
- 229910052725 zinc Inorganic materials 0.000 claims description 16
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- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000001179 sorption measurement Methods 0.000 claims description 13
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 12
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- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical group FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 claims description 4
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- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims description 3
- 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 2
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- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 4
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
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- 229910052736 halogen Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
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- 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 2
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- 150000008282 halocarbons Chemical class 0.000 description 2
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- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000010943 off-gassing Methods 0.000 description 2
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- 229910052697 platinum Inorganic materials 0.000 description 2
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- 238000002310 reflectometry Methods 0.000 description 2
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- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 description 1
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 description 1
- DMUPYMORYHFFCT-UHFFFAOYSA-N 1,2,3,3,3-pentafluoroprop-1-ene Chemical compound FC=C(F)C(F)(F)F DMUPYMORYHFFCT-UHFFFAOYSA-N 0.000 description 1
- RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 1
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- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 1
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- -1 halogen hydrides Chemical class 0.000 description 1
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- UCUXYVNKFJJXDE-UHFFFAOYSA-N nitrate;hydrate Chemical compound O.[O-][N+]([O-])=O UCUXYVNKFJJXDE-UHFFFAOYSA-N 0.000 description 1
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
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- B01J37/08—Heat treatment
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- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/21—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms with simultaneous increase of the number of halogen atoms
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Description
a)金属塩溶液および水酸化物溶液を調製する工程と、
b)7.5を超えるpHで溶液を混合して、金属水酸化物(複数可)を沈殿させる工程と、
c)沈殿した金属水酸化物を乾燥させる工程と、
d)金属水酸化物(複数可)を焼成して金属酸化物(複数可)を形成する工程と、を含む。
500mLの脱イオン水ヒールを、オーバーフロー、オーバーヘッド撹拌機、pHプローブ、および熱電対を装着した1.7Lのジャケット付きガラス容器に添加し、15°Cに冷却した。撹拌機を500rpmで作動させ、実施例5に保存し、250rpmで回転させた。
活性=50-(S2-RT)
式中、S2は、ストレス温度2で10%の134aの収率を得るための予測反応温度であり、RTは、287.5℃である。
安定性=50-(S3-RT)
式中、S3は、ストレス温度3で10%の134aの収率を得るための予測反応温度であり、RTは、287.5℃である。
表3を参照して以下に記載されるように適合される、実施例1~8の方法に実質的に従って触媒を調製した。
図1および2、ならびに表4は、投与の開始から2、6、および15分後、ならびに投与が完了した後の測定粒径分布を示す。開始から2分後には、非常に小さな粒子がほとんどであるが、いくつかの大きな粒子も存在する。これらの大きな粒子は、投与開始から6分後には存在しなくなり、その時点までに小さな粒子の総数は最大となる。その後、分布は大きなサイズへの段階的なシフトを示す。
図3および4、ならびに表5は、投与の開始から2、6、および15分後、ならびに投与が完了した後の測定粒径分布を示す。開始から2分後には、大きな粒子の存在がほとんどである。しかし6分で、大きな粒子の数は低減し、小さな粒子の数は有意に増加した。粒子システムは、投与の最後の15分間ではほとんど変化を示さない。
図5および6、ならびに表6は、投与の開始から2、6、および15分後、ならびに投与が完了した後の測定粒径分布を示す。開始から2分後には、小さな粒子の存在がほとんどであり、それは6分に達すると数が増加する。その後、それらの小さな粒子の総数は徐々に減少し、大きな粒子の数は増加する。
図7および8、ならびに表7は、投与の開始から2、6、および15分後、ならびに投与が完了した後の測定粒径分布を示す。分布は、投与のプロセスにわたって、より小さい粒子の数が徐々に増加することを示す。投与の最後の15分間では、より大きな粒子の数が減少する。
比較例の触媒を以下の方法に従って作製した。20 500mLの脱イオン水ヒールを、オーバーフロー、オーバーヘッド撹拌機、pHプローブ、および熱電対を装着した1.7Lのジャケット付きガラス容器に添加し、15°Cに冷却した。撹拌機を500rpmで作動させた。
500mLの脱イオン水ヒールを、オーバーフロー、オーバーヘッド撹拌機、pHプローブ、および熱電対を装着した1.7Lのジャケット付きガラス容器に添加し、15°Cに冷却した。撹拌機を500rpmで作動させ、実施例5に保存し、250rpmで回転させた。
500mLの脱イオン水ヒールを、オーバーフロー、オーバーヘッド撹拌機、pHプローブ、および熱電対を装着した1.7Lのジャケット付きガラス容器に添加し、15°Cに冷却した。撹拌機を411rpmで作動させた。Cr(NO3)2(OH)(水溶液)の溶液(500g)を600mLビーカーに量り取り、In(NO3)3.3H2O (13.3g)および17%のNH4OH溶液(318g)を別のビーカーに量り取った。次いで、触媒を、目標pH8.5で、実施例24と同じ手順によって調製し、スラリーを脱イオン水(3×600mL)で洗浄した。
500mLの脱イオン水ヒールを、オーバーフロー、オーバーヘッド撹拌機、pHプローブ、および熱電対を装着した1.7Lのジャケット付きガラス容器に添加し、15°Cに冷却した。撹拌機を406rpmで作動させた。Cr(NO3)2(OH)(水溶液)の溶液(500g)を600mLビーカーに量り取り、ZrOCl2.8H2O(13.6g)のメタノール(50mL)溶液および17%のNH4OH溶液(350g)を別のビーカーに量り取った。次いで、触媒を、目標pH8.5で、実施例24と同じ手順によって調製し、スラリーを脱イオン水(3×600mL)で洗浄した。
実施例24~26の触媒の性能を、HFとの接触による1233xfのフッ素化からの1234yfおよび245cbの生成について試験した。結果を市販のクロミア触媒(比較例27)および市販のZnドープクロミア触媒(比較例28)の結果と比較した。
実施例24および25の触媒の性能を、245cbの脱フッ化水素化からの1234yfの生成について試験した。結果を市販のクロミア触媒(比較例29)および市販の亜鉛促進クロミア触媒(比較例30)の結果と比較した。
実施例24~26の触媒の性能を、245ebの脱フッ化水素化からの1234yfおよび245cbの生成について試験した。結果を市販のクロミア触媒(比較例31)および市販の亜鉛促進クロミア触媒(比較例32)の結果と比較した。
Claims (20)
- C 3 ヒドロハロカーボン種のフッ素化及び/又は脱ハロゲン化水素化のためのプロセスであって、前記C 3 ヒドロハロカーボン種と触媒とを接触させることを含み、前記触媒が、少なくとも80重量%のクロミアおよび少なくとも1種の追加の金属またはその化合物を含み、前記触媒が0.3cm3/gを超える全細孔容積を有し、平均細孔直径が90Å以上であり、前記全細孔容積がN2吸着圧入法によって測定され、前記平均細孔直径がN2BET吸着圧入法によって測定され、前記少なくとも1種の追加の金属がZr、Nb、Mo、Ni、In、Zn、およびそれらの混合物から選択されるプロセス。
- 前記触媒の前記細孔容積が0.4cm3/g以上、または0.5cm3/g以上である、請求項1に記載のプロセス。
- N2BET吸着圧入法によって測定される場合、前記触媒の前記平均細孔直径が100Å以上である、請求項1または2に記載のプロセス。
- N 2 BET吸着圧入法によって測定される場合、前記触媒の前記平均細孔直径が110Å以上または120Å以上である、請求項3に記載のプロセス。
- N2BJH吸着圧入法によって測定される場合、前記触媒の前記平均細孔直径が130Å以上である、請求項1~4のいずれか一項に記載のプロセス。
- N 2 BJH吸着圧入法によって測定される場合、前記触媒の前記平均細孔直径が140Å以上、150Å以上、または170Å以上である、請求項5に記載のプロセス。
- N2BJH脱着圧入法によって測定される場合、前記触媒の前記平均細孔直径が90Å以上である、請求項1~6のいずれか一項に記載のプロセス。
- N 2 BJH脱着圧入法によって測定される場合、前記触媒の前記平均細孔直径が100Å以上、110Å以上、または120Å以上である、請求項7に記載のプロセス。
- 前記触媒が、複数の触媒粒子を含む1つまたは複数のペレットの形態で提供される、請求項1~8のいずれか一項に記載のプロセス。
- 前記触媒ペレットがグラファイトを、0.5重量%~10重量%の量で含む、請求項9に記載のプロセス。
- 前記触媒ペレットがグラファイトを、1重量%~5重量%の量で含む、請求項10に記載のプロセス。
- 前記触媒ペレットが1mm~100mmの最長寸法を有する、請求項9~11のいずれか一項に記載のプロセス。
- 前記触媒中の前記金属が遷移金属である、請求項1~12のいずれか一項に記載のプロセス。
- 前記触媒が亜鉛を含む、請求項13に記載のプロセス。
- 前記触媒が未使用物である、請求項1~14のいずれか一項に記載のプロセス。
- ヒドロ(ハロ)フルオロプロパンと前記触媒とを接触させて、フルオロプロペンを生成することを含む、請求項1~15のいずれか一項に記載のプロセス。
- 前記フルオロプロペンが、テトラフルオロプロペン(1234)である、請求項16に記載のプロセス。
- 前記ヒドロ(ハロ)フルオロプロパンが、1,1,1,2,3-ペンタフルオロプロパン、1,1,1,2,2-ペンタフルオロプロパン、および/または1,1,1,3,3-ペンタフルオロプロパンから選択される化合物を含む、請求項17に記載のプロセス。
- 前記テトラフルオロプロペンが、1,3,3,3-テトラフルオロプロペンおよび/または2,3,3,3-テトラフルオロプロペンを含む、請求項17または請求項18に記載のプロセス。
- 前記方法が気相中で行われる、請求項16~19のいずれか一項に記載のプロセス。
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KR20190047718A (ko) | 2019-05-08 |
EP3509741B2 (en) | 2024-01-24 |
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US20190217276A1 (en) | 2019-07-18 |
US11406965B2 (en) | 2022-08-09 |
WO2018046928A1 (en) | 2018-03-15 |
JP6876124B2 (ja) | 2021-05-26 |
CN109843429B (zh) | 2023-04-07 |
JP2021087952A (ja) | 2021-06-10 |
KR102311685B1 (ko) | 2021-10-14 |
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CN109843429A (zh) | 2019-06-04 |
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