JP2008526688A - 光化学反応用の末端官能化パーフルオロ(アルキルビニルエーテル)反応器壁の官能化共重合体、炭化水素およびハロ炭化水素中のフッ素含有率の増加方法およびオレフィン製造方法 - Google Patents
光化学反応用の末端官能化パーフルオロ(アルキルビニルエーテル)反応器壁の官能化共重合体、炭化水素およびハロ炭化水素中のフッ素含有率の増加方法およびオレフィン製造方法 Download PDFInfo
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- 229930003316 Vitamin D Natural products 0.000 description 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
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- 150000001768 cations Chemical class 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
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- 239000010941 cobalt Substances 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- 235000019166 vitamin D Nutrition 0.000 description 1
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- 229940046008 vitamin d Drugs 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
- B01J19/127—Sunlight; Visible light
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
- B01J19/123—Ultraviolet light
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
- B01J19/243—Tubular reactors spirally, concentrically or zigzag wound
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Abstract
Description
ハロゲン化炭化水素化合物または炭化水素化合物の塩素含有率を、光の存在下に前記化合物を塩素(Cl2)と反応させることによって増加させる方法が本発明に含まれる。
ハロゲン化炭化水素化合物または炭化水素化合物についての、上記のように光の存在下に前記化合物を塩素(Cl2)と反応させ、次に、製造されたハロゲン化炭化水素をフッ化水素と反応させることによる方法は本発明に含まれる。フッ素化反応は当該技術でよく知られている。それらは両方とも様々なフッ素化触媒を用いて気相か液相かのどちらかで行うことができる。例えば、(非特許文献5)およびそれに引用された参考文献を参照されたい。フッ素化触媒の存在下での気相フッ素化が注目すべきである。好ましいフッ素化触媒には、クロム触媒(例えば、Cr2O3それだけでまたはCr2O3上のハロゲン化マグネシウムもしくはハロゲン化亜鉛などの他の金属と共に);カーボンに担持されたハロゲン化クロム(III);場合によりグラファイト上のクロムとマグネシウムとの混合物(元素状金属、金属酸化物、金属ハロゲン化物、および/または他の金属塩をはじめとする);ならびに場合によりグラファイト、アルミナ、またはフッ化アルミニウムなどのハロゲン化アルミニウム上のクロムとコバルトとの混合物(元素状金属、金属酸化物、金属ハロゲン化物、および/または他の金属塩をはじめとする)が含まれる。
ハロゲン化炭化水素化合物または炭化水素化合物から、前記化合物を上記のように光の存在下に塩素(Cl2)と反応させ、次に光塩素化で製造されたハロゲン化炭化水素を脱ハロゲン化水素処理にかけることによってオレフィンを製造する方法は本発明に含まれる。脱ハロゲン化水素処理反応は当該技術でよく知られている。それらは、様々な触媒を用いて気相か液相かのどちらかで両方とも行うことができる。例えば、(非特許文献6)およびそれに引用された参考文献を参照されたい。触媒の存在下での気相脱ハロゲン化水素処理は注目すべきである。脱ハロゲン化水素処理に好適な触媒には、カーボン、金属(元素状金属、金属酸化物、金属ハロゲン化物、および/または他の金属塩をはじめとする);アルミナ;フッ素化アルミナ;フッ化アルミニウム;クロロフッ素化アルミニウム;アルミニウムに担持された金属;フッ化またはクロロフッ化アルミニウムに担持された金属;フッ化アルミニウムに担持されたフッ化マグネシウム;フッ素化アルミナに担持された金属;カーボンに担持されたアルミナ;カーボンに担持されたフッ化またはクロロフッ化アルミニウム;カーボンに担持されたフッ素化アルミナ;カーボンに担持された金属、ならびに金属、フッ化またはクロロフッ化アルミニウム、およびグラファイトの混合物が含まれる。触媒での(場合によりアルミナ、フッ化アルミニウム、クロロフッ化アルミニウム、フッ素化アルミナ、またはカーボン上の)使用に好適な金属には、クロム、鉄、およびランタンが含まれる。好ましくは、担体上で使用されるとき、触媒の総金属含有率は約0.1〜20重量パーセント、典型的には約0.1〜10重量パーセントであろう。脱ハロゲン化水素処理用の好ましい触媒には、カーボン、アルミナ、およびフッ素化アルミナが含まれる。
光塩素化は、塩素化されるべき物質が通過するフルオロポリマーチュービング材料のコイルの入口端の第1回転の外側から(特に明記しない限り)0.5インチ(1.3cm)の距離に置いた110ボルト/275ワット太陽灯を用いて実施した。以下の実施例に用いたフルオロポリマーチュービングは18インチ(45.7cm)長さのナフィオン(登録商標)チューブ(0.065インチ(0.17cm)OD×0.055インチ(0.14cm)ID)であり、それは3インチ(7.6cm)の直径に巻かれ、好適な供給および出口ポートを含有した。有機供給物質および塩素を、標準流量測定装置を用いてチュービングへ供給した。内側のガス混合物を太陽灯により発生する光に露光させた。実験を周囲温度(約23℃)でおよびほぼ大気圧下に行った。チュービングに入る有機供給物質および光塩素化後の生成物をGC/MSを用いてオンライン分析した。結果はモル%で報告する。CFC−114はCClF2CClF2であり、CFC−114aはCF3CCl2Fであり、CFC−216baはCF3CClFCClF2であり、HCFC−226baはCF3CClFCHF2である。1.0sccm(標準立方センチメートル毎分)は約1.7(10)-8立方メートル毎秒に等しい。
5.0sccmの流量のHFC−134aおよび2.5sccmの流量の塩素ガスからなる供給ガスをナフィオン(登録商標)チュービング中へ導入した。光への1時間露光後に、生成物を分析し、75.7モル%のHFC−134a、19.8モル%のHCFC−124、3.7モル%のCFC−114aおよび0.8モル%の他の未同定化合物を含有することが分かった。CFC−114aおよびHCFC−124の総量対比でCFC−114aのモル収率は15.7%であった。
供給ガスは5.0sccmの流量のHFC−134および2.5sccmの流量の塩素ガスよりなった。光への1時間露光後に、生成物を分析し、71.2モル%のHFC−134、27.4モル%のHCFC−124a、1.1モル%のCFC−114および0.3モル%の他の未同定化合物を含有することが分かった。
供給ガスは5.0sccmの流量のHFC−236eaおよび2.5sccmの流量の塩素ガスよりなった。光への1時間露光後に、生成物を分析し、61.1モル%のHFC−236ea、5.6モル%のHCFC−226ba、32.3モル%のHCFC−226ea、0.7モル%のCFC−216baおよび0.3モル%の他の未同定化合物を含有することが分かった。
供給ガスは5.0sccmの流量のHFC−236eaおよび7.5sccmの流量の塩素ガスよりなった。光への1時間露光後に、生成物を分析し、60.3モル%のHFC−236ea、5.7モル%のHCFC−226ba、33.0モル%のHCFC−226ea、0.7モル%のCFC−216baおよび0.3モル%の他の未同定化合物を含有することが分かった。
HFC−245faを塩素化前に分析し、99.8%の純度を有することが分かった。供給ガスは3.5sccmの流量のHFC−245faおよび3.5sccmの流量の塩素ガスよりなった。光への1時間露光後に、生成物を分析し、67.1モル%のHFC−245fa、31.7モル%のHCFC−235fa、および1.2モル%の他の未同定化合物を含有することが分かった。
Claims (20)
- 反応器と光源からの光が反応器壁の一部を通って導かれるように置かれた光源とを含む光化学反応装置であって、
反応壁の前記部分が末端官能化パーフルオロ(アルキルビニルエーテル)の官能化共重合体を含み、共重合体の官能基が−SO2F、−SO2Cl、−SO3H、−CO2R(式中、RはHまたはC1〜C3アルキルである)、−PO3H2、およびそれらの塩からなる群から選択されることを特徴とする装置。 - 官能化共重合体が少なくとも1つのパーフルオロ化アルキレンモノマーと末端官能化パーフルオロ(アルキルビニルエーテル)との共重合体であることを特徴とする請求項1に記載の光化学反応装置。
- 官能化共重合体がテトラフルオロエチレンと末端官能化パーフルオロ(アルキルビニルエーテル)との共重合体であることを特徴とする請求項2に記載の光化学反応装置。
- 官能化共重合体がテトラフルオロエチレンと
FSO2CF2CF2OCF(CF3)CF2OCF=CF2、
CH3OC(O)CF2CF2CF2OCF(CF3)CF2OCF=CF2、および
CH3OC(O)CF2CF2OCF(CF3)CF2OCF=CF2からなる群から選択されたパーフルオロ(アルキルビニルエーテル)モノマーとの共重合体であるか、またはそれらの酸もしくは塩の形態であることを特徴とする請求項3に記載の光化学反応装置。 - 官能化共重合体がテトラフルオロエチレンとFSO2CF2CF2OCF(CF3)CF2OCF=CF2との共重合体であるか、またはその酸もしくは塩の形態であることを特徴とする請求項4に記載の光化学反応装置。
- 光源からの光が反応器壁を通って導かれて前記反応器中で反応体と相互作用する光化学的方法であって、
反応器壁を通って導かれる光が末端官能化パーフルオロ(アルキルビニルエーテル)の官能化共重合体を通って導かれ、共重合体の官能基が−SO2F、−SO2Cl、−SO3H、−CO2R(式中、RはHまたはC1〜C3アルキルである)、−PO3H2、およびそれらの塩からなる群から選択されることを特徴とする方法。 - 官能化共重合体が少なくとも1つのパーフルオロ化アルキレンモノマーと末端官能化パーフルオロ(アルキルビニルエーテル)との共重合体であることを特徴とする請求項6に記載の光化学的方法。
- 官能化共重合体がテトラフルオロエチレンと末端官能化パーフルオロ(アルキルビニルエーテル)との共重合体であることを特徴とする請求項7に記載の光化学的方法。
- 官能化共重合体がテトラフルオロエチレンと
FSO2CF2CF2OCF(CF3)CF2OCF=CF2、
CH3OC(O)CF2CF2CF2OCF(CF3)CF2OCF=CF2、および
CH3OC(O)CF2CF2OCF(CF3)CF2OCF=CF2からなる群から選択されたパーフルオロ(アルキルビニルエーテル)モノマーとの共重合体であるか、またはそれらの酸もしくは塩の形態であることを特徴とする請求項8に記載の光化学的方法。 - 官能化共重合体がテトラフルオロエチレンとFSO2CF2CF2OCF(CF3)CF2OCF=CF2との共重合体であるか、またはその酸もしくは塩の形態であることを特徴とする請求項9に記載の光化学的方法。
- 炭化水素およびハロ炭化水素から選択された少なくとも1つの化合物の塩素含有率が光の存在下での塩素との反応によって増加していることを特徴とする請求項6に記載の光化学的方法。
- 炭化水素およびハロ炭化水素から選択された少なくとも1つの化合物のフッ素含有率を増加させる方法であって、
(a)前記少なくとも1つの化合物を請求項11に記載の方法に従って光塩素化する工程と、
(b)(a)での光塩素化によって製造されたハロゲン化炭化水素をHFと反応させる工程と
を含むことを特徴とする方法。 - (a)でCF3CH2CHF2がCF3CH2CClF2へ光塩素化され、そして(b)でCF3CH2CClF2がHFと反応してCF3CH2CF3を製造することを特徴とする請求項12に記載の方法。
- (a)でCF3CH2FがCF3CHClFへ光塩素化され、そして(b)でCF3CHClFがHFと反応してCF3CHF2を製造することを特徴とする請求項12に記載の方法。
- (a)でCHF2CHF2がCHF2CClF2へ光塩素化され、そして(b)でCHF2CClF2がHFと反応してCF3CHF2を製造することを特徴とする請求項12に記載の方法。
- (a)少なくとも2個の炭素原子および少なくとも2個の水素原子を含有する炭化水素およびハロ炭化水素から選択された少なくとも1つの化合物を請求項11に記載の方法に従って光塩素化して水素置換基および塩素置換基を隣接炭素原子上に含有するハロゲン化炭化水素を製造する工程と、
(b)(a)での光塩素化によって製造されたハロゲン化炭化水素を脱ハロゲン化水素処理にかける工程と
を含むことを特徴とするオレフィン化合物の製造方法。 - (a)でフッ素を含有する化合物が光塩素化されることを特徴とする請求項16に記載の方法。
- (a)でCH3CHF2が光塩素化されてCH3CClF2を製造し、そして(b)でCH3CClF2が脱ハロゲン化水素処理されてCF2=CH2を製造することを特徴とする請求項17に記載の方法。
- (a)でCHF2CHF2が光塩素化されてCHF2CClF2を製造し、そして(b)でCHF2CClF2が脱ハロゲン化水素処理されてCF2=CF2を製造することを特徴とする請求項17に記載の方法。
- (a)でCF3CHFCHF2が光塩素化されてCF3CHFCClF2を製造し、そして(b)でCF3CHFCClF2が脱ハロゲン化水素処理されてCF3CF=CF2を製造することを特徴とする請求項17に記載の方法。
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PCT/US2005/046265 WO2006069106A1 (en) | 2004-12-22 | 2005-12-19 | Functionalized copolymers of terminally functionalized perfluoro (alkyl vinyl ether) reactor wall for photochemical reactions, process for increasing fluorine content in hydrocarbons and halohydrocarbons and olefin production |
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EP2739595B1 (en) | 2011-08-07 | 2018-12-12 | Blue Cube IP LLC | Process for the production of chlorinated propenes |
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WO2014046977A1 (en) | 2012-09-20 | 2014-03-27 | Dow Global Technologies, Llc | Process for the production of chlorinated propenes |
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