JP6674974B2 - ハロゲン化アルカンの脱ハロゲン化水素化によるハロゲン化アルケンの調製のための方法 - Google Patents
ハロゲン化アルカンの脱ハロゲン化水素化によるハロゲン化アルケンの調製のための方法 Download PDFInfo
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- JP6674974B2 JP6674974B2 JP2018084183A JP2018084183A JP6674974B2 JP 6674974 B2 JP6674974 B2 JP 6674974B2 JP 2018084183 A JP2018084183 A JP 2018084183A JP 2018084183 A JP2018084183 A JP 2018084183A JP 6674974 B2 JP6674974 B2 JP 6674974B2
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- dehydrochlorination
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- 238000000034 method Methods 0.000 title claims description 112
- 230000008569 process Effects 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 19
- 150000001335 aliphatic alkanes Chemical class 0.000 title description 3
- 150000001336 alkenes Chemical class 0.000 title description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 210
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 67
- 229910052751 metal Inorganic materials 0.000 claims description 66
- 239000002184 metal Substances 0.000 claims description 66
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 62
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 62
- 238000007033 dehydrochlorination reaction Methods 0.000 claims description 36
- 238000005660 chlorination reaction Methods 0.000 claims description 35
- 239000012320 chlorinating reagent Substances 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 21
- 239000011261 inert gas Substances 0.000 claims description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 239000003153 chemical reaction reagent Substances 0.000 claims description 14
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052759 nickel Inorganic materials 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 230000008929 regeneration Effects 0.000 claims description 10
- 238000011069 regeneration method Methods 0.000 claims description 10
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 claims description 3
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- PLTIOZOVDUUXDQ-UHFFFAOYSA-N 3,3-dichloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)CC(Cl)Cl PLTIOZOVDUUXDQ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
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- 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 7
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 description 7
- ZGOMEYREADWKLC-UHFFFAOYSA-N 3-chloro-1,1,1,3-tetrafluoropropane Chemical compound FC(Cl)CC(F)(F)F ZGOMEYREADWKLC-UHFFFAOYSA-N 0.000 description 7
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- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
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- 239000001301 oxygen Substances 0.000 description 5
- 229910052703 rhodium Inorganic materials 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 229910052684 Cerium Inorganic materials 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
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- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 4
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- 229910002804 graphite Inorganic materials 0.000 description 4
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- 238000001354 calcination Methods 0.000 description 3
- 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 3
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- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
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- B01J21/20—Regeneration or reactivation
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- B01J23/90—Regeneration or reactivation
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
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- B01J23/96—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides of the noble metals
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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Description
好ましくは、本発明の方法は、対応するC3〜7ヒドロクロロフルオロアルカンを脱塩化水素化することによるC3〜7(ヒドロ)(クロロ)フルオロアルケンの調製を対象とする。
本発明の方法で使用される触媒は、(a)金属酸化物、(b)金属ハロゲン化物、(c)ゼロ価金属、または(d)炭素系触媒のうちの1つ以上を含む。本発明の一態様において、触媒は、(a)金属酸化物、(b)金属ハロゲン化物、または(c)ゼロ価金属のうちの1つ以上を含む。実施形態において、触媒は、(a)金属酸化物または(b)金属ハロゲン化物のうちの1つ以上を含む。好ましくは、触媒は、金属酸化物を含む。
本発明の方法の重要な特徴は、(i)金属系触媒が、触媒をヒドロクロロフルオロアルカンと接触させる前に塩素化されて、脱塩化水素化を触媒するか、または(ii)触媒をヒドロクロロフルオロアルカンと接触させるステップが、HCl共供給物の存在下で行われることである。あるいは、触媒予備塩素化ステップ(i)及びHCl共供給物(ii)の両方が、本発明の方法で使用され得る。理論に束縛されず、ヒドロクロロフルオロアルカン及び反応条件などの組み合わせに応じて、触媒予備塩素化ステップ(i)及びHCl共供給物の使用(ii)のうちの1つまたは両方が驚くべきことに、一切の所望されない脱フッ化水素反応を上回って、所望される脱塩化水素化の選択性を増加させ、かつ/または使用に際して、触媒の安定性を増加させると考えられる。
CCl3CH2CCl2H(HCC−240fa)+4HF→CF3CH2CClFH(HCFC−244fa)+4HCl
CCl3CH2CCl2H(HCC−240fa)+3HF→CF3CH2CCl2H(HCFC−243fa)+3HCl
・温度=400℃
・244bbの流速=5ml/分
・反応器=グラスウール及びロッド支持部を含むガラス内張りステンレス鋼
・1.2gの焼結されたNiペレット
[項1]
(ヒドロ)(クロロ)フルオロアルケンの調製のための方法であって、反応器の中でヒドロクロロフルオロアルカンを含む試薬流を触媒と接触させて、前記ヒドロクロロフルオロアルカンの少なくとも一部を脱塩化水素化して、前記(ヒドロ)(クロロ)フルオロアルケン及び塩化水素(HCl)を含む生成物流を生成することを含み、前記触媒が、金属酸化物触媒、金属ハロゲン化物触媒、ゼロ価金属触媒、炭素系触媒、及びそれらの混合物から選択され、
(i)前記触媒が、それを前記ヒドロクロロフルオロアルカンを含む前記試薬流と接触させる前に塩素化され、かつ/または
(ii)前記接触ステップが、HCl共供給物の存在下で行われる、方法。
[項2]
ステップ(i)において、前記触媒が、塩化水素(HCl)、塩素(Cl2)、またはそれらの混合物を含む塩素化剤で塩素化される、項1に記載の方法。
[項3]
ステップ(i)が、約200℃〜約600℃の温度で、前記触媒を塩素化剤と接触させることを含む、項1または2に記載の方法。
[項4]
前記触媒が、約1時間〜約48時間の間、0.1分−1〜約3分−1の空間速度を有する前記塩素化剤の流体流により接触される、項3に記載の方法。
[項5]
塩素化剤が、不活性ガスの存在により希釈され、好ましくは、前記不活性ガスが、窒素である、項2〜4のいずれかに記載の方法。
[項6]
前記ステップ(i)が、触媒乾燥ステップと単一手順に組み合わせられる、項1〜5のいずれかに記載の方法。
[項7]
ステップ(ii)において、前記反応器に供給されるHClの量が、ヒドロクロロフルオロアルカンと前記反応器に供給されるHClとを組み合わせた量に基づいて、最大50mol%である、項1〜6のいずれかに記載の方法。
[項8]
前記反応器に供給されるHClの量が、ヒドロクロロフルオロアルカンと前記反応器に供給されるHClとを組み合わせた量に基づいて、少なくとも1mol%である、項1〜7のいずれかに記載の方法。
[項9]
前記生成物流中の前記HClの少なくとも一部が、前記反応器に再循環されて、前記HCl共供給物の少なくとも一部を構成する、項1〜8のいずれかに記載の方法。
[項10]
前記HCl共供給物の少なくとも一部が、前記ヒドロクロロフルオロアルカンを製造する、前の方法ステップに由来する、項1〜9のいずれかに記載の方法。
[項11]
前記(ヒドロ)(クロロ)フルオロアルケンが、C3〜7(ヒドロ)(クロロ)フルオロアルケンであり、前記ヒドロクロロフルオロアルカンが、C3〜7ヒドロクロロフルオロアルカンである、項1〜10のいずれかに記載の方法。
[項12]
前記C3〜7(ヒドロ)(クロロ)フルオロアルケンが、(ヒドロ)(クロロ)フルオロプロペンであり、前記C3〜7ヒドロクロロフルオロアルカンが、ヒドロクロロフルオロプロパンである、項11に記載の方法。
[項13]
前記(ヒドロ)(クロロ)フルオロプロペンが、1−クロロ−3,3,3−トリフルオロプロペン(CF3CH=CHCl、HCFO−1233zd)及び2−クロロ−3,3,3−トリフルオロプロペン(CF3CHCl=CH2、HCFO−1233xf)から選択されるヒドロクロロフルオロプロペンである、項12に記載の方法。
[項14]
前記ヒドロクロロフルオロプロパンが、1,1−ジクロロ−3,3,3−トリフルオロプロパン(CF3CH2CHCl2、HCFC−243fa)である、HCFO−1233zdを調製するための、項13に記載の方法。
[項15]
前記ヒドロクロロフルオロプロパンが、1,2−ジクロロ−3,3,3−トリフルオロプロパン(CF3CHClCH2Cl、HCFC−243db)である、HCFO−1233xfを調製するための、項13に記載の方法。
[項16]
前記(ヒドロ)(クロロ)フルオロプロペンが、1,3,3,3−テトラフルオロプロペン(CF3CH=CHF、HFO−1234ze)及び2,3,3,3−テトラフルオロプロペン(CF3CF=CH2、HFO−1234yf)から選択されるヒドロフルオロプロペンである、項12に記載の方法。
[項17]
前記ヒドロクロロフルオロプロパンが、2−クロロ−1,1,1,2−テトラフルオロプロパン(HCFC−244bb)である、HFO−1234yfを調製するための、項16に記載の方法。
[項18]
前記ヒドロクロロフルオロプロパンが、3−クロロ−1,1,1,3−テトラフルオロプロパン(HCFC−244fa)である、HFO−1234zeを調製するための、項16に記載の方法。
[項19]
前記触媒が、金属酸化物を含み、前記金属が、Li、Na、K、Ca、Mg、Cs、Sc、Al、Y、Ti、Zr、Hf、V、Nb、Ta、Cr、Mo、W、Mn、Re、Fe、Ru、Co、Rh、Ir、Ni、Pd、Pt、Cu、Ag、Au、Zn、La、及びCeから選択される、項1〜18のいずれかに記載の方法。
[項20]
前記金属酸化物が、Cr2O3、ZrO2、Li2O、Na2O、K2O、CaO、MgO、またはCs2Oのうちの1つ以上を含む、項19に記載の方法。
[項21]
前記触媒が、亜鉛/クロミア触媒を含む、項1〜20のいずれかに記載の方法。
[項22]
前記脱塩化水素化が、約0.1〜約40bara、好ましくは約1〜約5baraの圧力で行われる、項1〜21のいずれかに記載の方法。
[項23]
前記脱塩化水素化が、約100℃〜約600℃、好ましくは約180℃〜約420℃の温度で行われる、項1〜22のいずれかに記載の方法。
[項24]
前記触媒と接触するヒドロクロロフルオロアルカンを含む前記試薬流が、約0.1分−1〜約10分−1の空間速度を有する、項1〜23のいずれかに記載の方法。
[項25]
前記方法が、連続的であり、前記触媒が、再生酸化、再生オキシフッ素化、再生還元、または再生塩素化のうちの1つ以上により周期的に再生される、項1〜24のいずれかに記載の方法。
[項26]
前記触媒が、(i)再生酸化または(ii)再生オキシフッ素化、及びその後の(iii)再生塩素化により再生される、項25に記載の方法。
[項27]
前記触媒が、再生オキシ塩素化により再生される、項26に記載の方法。
[項28]
概して本明細書に記載される、あらゆる新規方法。
Claims (16)
- 2,3,3,3−テトラフルオロプロペン(1234yf)の調製のための方法であって、反応器の中で2−クロロ−1,1,1,2−テトラフルオロプロパン(244bb)を含む試薬流を触媒と接触させて、前記244bbの少なくとも一部を脱塩化水素化して、前記1234yf及び塩化水素(HCl)を含む生成物流を生成することを含み、前記触媒が、ニッケルを含むゼロ価金属触媒であり、前記触媒が、それを前記244bを含む前記試薬流と接触させる前に塩素化され、
前記触媒が、再生酸化または再生オキシフッ素化、及びその後の再生塩素化により周期的に再生される方法。 - 前記触媒が、塩化水素(HCl)、塩素(Cl2)、またはそれらの混合物を含む塩素化剤で塩素化される、請求項1に記載の方法。
- 前記触媒が、200℃〜600℃の温度で塩素化される、請求項2に記載の方法。
- 前記触媒が1時間〜48時間の間、0.1分 −1 〜3分 −1 の空間速度を有する前記塩素化剤の流体流と接触される、請求項2又は3に記載の方法。
- 塩素化剤が不活性ガスの存在により希釈される、請求項2〜4のいずれか一項に記載の方法。
- 前記不活性ガスが窒素である、請求項5に記載の方法。
- 前記触媒を塩素化するステップが、触媒乾燥ステップと単一ステップに組み合わせられる、請求項1〜6のいずれか一項に記載の方法。
- 前記接触ステップが、HCl共供給物の存在下で行われる、請求項1〜7のいずれか一項に記載の方法。
- 前記反応器に供給されるHClの量が、244bbと前記反応器に供給されるHClとを組み合わせた量に基づいて、最大50mol%であり、かつ/または前記反応器に供給されるHClの量が、244bbと前記反応器に供給されるHClとを組み合わせた量に基づいて、少なくとも1mol%である、請求項8に記載の方法。
- 前記生成物流中の前記HClの少なくとも一部が、前記反応器に再循環されて、前記HCl共供給物の少なくとも一部を構成し、かつ/または前記HCl共供給物の少なくとも一部が、前記244bbを製造する、前の方法ステップに由来する、請求項8又は9に記載の方法。
- 前記脱塩化水素化が、0.1〜40baraの圧力で行われる、請求項1〜10のいずれかに記載の方法。
- 前記脱塩化水素化が、1〜5baraの圧力で行われる、請求項11に記載の方法。
- 前記脱塩化水素化が、前記脱塩化水素化が100℃〜600℃の温度で行われる、請求項1〜12のいずれかに記載の方法。
- 前記脱塩化水素化が、前記脱塩化水素化が180℃〜420℃の温度で行われる、請求項13に記載の方法。
- 前記触媒と接触する244bbを含む前記試薬流が、0.1分−1〜10分−1の空間速度を有する、請求項1〜14のいずれかに記載の方法。
- 前記触媒が、再生オキシ塩素化により再生される、請求項1〜15のいずれかに記載の方法。
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