JP2013515158A - 2,3,3,3−テトラフルオロプロペン、1,1,2,3−テトラクロロプロペン、2−クロロ−3,3,3−トリフルオロプロペン、または2−クロロ−1,1,1,2−テトラフルオロプロパンを含む組成物 - Google Patents
2,3,3,3−テトラフルオロプロペン、1,1,2,3−テトラクロロプロペン、2−クロロ−3,3,3−トリフルオロプロペン、または2−クロロ−1,1,1,2−テトラフルオロプロパンを含む組成物 Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims abstract description 134
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title claims abstract description 55
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- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 title abstract description 3
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 title description 2
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- 230000035484 reaction time Effects 0.000 description 1
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- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
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- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
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- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
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- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 230000001629 suppression Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
HFO−1234yf(2,3,3,3−テトラフルオロプロペン)は、他の用途の中でも、冷媒、熱伝達流体、エアロゾル噴射剤、フォーム発泡剤(foam expansion agent)としての用途について提案されてきた。それはまた、有利には、HFO−1234yfが、Physical Chemistry Chemical Physics,2007,volume 9,pages 1−13において、V.C.Papadimitriouらにより報告されたとおりの低地球温暖化係数(GWP)を有することもわかった。したがって、HFO−1234yfは、より高いGWP飽和HFC冷媒を置き換えるための良い候補である。
HCO−1230xaは、触媒の存在下でフッ化水素(HF)との反応によりフッ素化されて、HCFO−1233xfを生成し得る。この反応は、図1に示される。
一部の実施形態において、HCFO−1233xfは、フッ素化によってHCFC−HCFC−244bb、および/またはHFO−1234yfを作製するために使用され得る。
一部の実施形態において、HCFC−244bbの脱水素塩素化は、HFO−1234yfを調製するために用いられる。
HFO−1234yfを含む本明細書で開示される組成物は、低地球温暖化係数の熱伝達組成物、エアロゾル噴射剤、フォーム発泡剤(expansion agent)((発泡剤(foaming agent)または発泡剤(blowing agent))としても知られる)、溶剤、洗浄剤、キャリア流体、置換乾燥剤、バフ研磨剤、重合媒体、ポリオレフィンおよびポリウレタン用発泡剤、ガス状誘電体、消火剤、および液体またはガス状形態の火災抑制剤として有用である。開示される組成物は、熱を熱源からヒートシンクに運ぶために使用される作業流体として作用し得る。このような熱伝達組成物は、流体が、相変化を受ける;すなわち、液体から気体へ、そして戻るまたは逆もまた同様のサイクルにおける冷媒としても有用であり得る。
以下の一般手順は、フッ素化反応の生成物の分析に用いられる方法の説明である。反応器全流出物の一部を、質量選択検出器を備えたガスクロマトグラフ(GC/MS)を用いる有機生成物の分析のためにオンラインで試料採取した。ガスクロマトグラフィーは、不活性炭素担体上にWilmington,DelawareのE.I.du Pont de Nemours and Company(以後「DuPont」)により商標Krytox(登録商標)下で販売されるペルフッ素化ポリエーテルが入っている、20フィート(6.1m)長×1/8インチ(0.32cm)直径のチューブを用いた。ヘリウム流量は、30mL/分(5.0×10−7m3/秒)であった。ガスクロマトグラフ条件は、3分間の初期保持時間について60℃、続いて、6℃/分の速度で200℃にプログラム化する温度であった。
HCFO−1233xfのHCFC−244bbへのフッ素化
20グラムの粘性SbF5が入っているPTFE製小バイアルの内容物を、乾燥した400mLのHastelloy(登録商標)のシェーカーチューブ中に注ぎ入れた。このチューブを閉じ、リーク試験のために窒素で加圧した。次いで、シェーカーチューブをドライアイスで−40℃未満に冷却し、ゆっくり放出し、次いで、空にした。75グラム(3.75モル)の無水HF、続いて、165グラム(1.26モル)のHCFO−1233xfを、シェーカーチューブ中に凝縮させた。シェーカーチューブをバリケード内に置き、振とうを開始した。
HCFO−1233xfのHCFC−244bbへのフッ素化
20グラムの粘性SbF5が入っているPTFE製小バイアルの内容物を、乾燥した400mLのHastelloy(登録商標)のシェーカーチューブ中に注ぎ入れた。このチューブを閉じ、リーク試験のために窒素で加圧した。次いで、シェーカーチューブをドライアイスで−40℃未満に冷却し、ゆっくり放出し、次いで、空にした。53グラム(2.65モル)の無水HF、続いて、227グラム(1.74モル)のHCFO−1233xfをシェーカーチューブ中に移し、冷却シェーカーチューブ中に凝縮させた。シェーカーチューブをバリケード内に置き、振とうを開始した。
実施例3は、触媒の不存在下でのHCFC−244bb(2−クロロ−1,1,1,2−テトラフルオロプロパン)のHFO−1234yf(2,3,3,3−テトラフルオロプロペン)への転化を実証する。
実施例4は、触媒の不存在下でのHCFC−244bb(2−クロロ−1,1,1,2−テトラフルオロプロパン)のHFO−1234yf(2,3,3,3−テトラフルオロプロパン)への転化を実証する。
実施例5は、活性炭触媒の存在下でのHCFC−244bb(2−クロロ−1,1,1,2−テトラフルオロプロパン)の脱水素塩素化を実証する。
Claims (20)
- HFO−1234yfと、HCO−1250xf、HCC−260da、HCC−260db、HCC−240aa、HCO−1230xa、HCFO−1233xf、HCFO−1233zd、HCFC−244bb、HCFC−244db、HFO−1234ze、HFC−245cb、HFO−1243zf、HCFO−1223za、HCFO−1224zb、HFO−1225zc、HCFC−241db、HCFC−242dc、HCFO−1232xf、HCFO−1231xf、およびHCFO−1233yfからなる群から選択される少なくとも1種の追加の化合物とを含む組成物。
- HCFO−1232xfを含む、請求項1に記載の組成物。
- HCFC−243db、HCFO−1233xf、HCFO−1231xf、HCFC−242dcおよびHCFC−241dbからなる群から選択される少なくとも1種の化合物をさらに含む、請求項2に記載の組成物。
- HCFC−243dbおよびHFC−245faからなる群から選択される少なくとも1種の化合物をさらに含む、請求項1に記載の組成物。
- 組成物の全質量に基づいて、約1質量パーセント未満の前記追加の化合物を含有する、請求項1に記載の組成物。
- 約1ppm〜約1000ppmのHFC−245cbをさらに含む、請求項1〜5のいずれか一項に記載の組成物。
- HCO−1230xaと、プロピレン、HCO−1260zf、HCC−260da、HCC−260db、HCO−1250xf、HCC−250aa、およびHCC−240aaからなる群から選択される少なくとも1種の追加の化合物とを含む組成物。
- HCC−240aaを含む、請求項7に記載の組成物。
- HCC−250aaおよびHCC−260daからなる群から選択される少なくとも1種の化合物をさらに含む、請求項8に記載の化合物。
- HCFO−1233xfと、プロピレン、HCO−1260zf、HCC−260da、HCC−260db、HCO−1250xf、HCC−250aa、HCC−240aa、HCO−1230xa、HFO−1243zf、HCFO−1223za、HCFO−1224zb、HFO−1225zc、HCFO−1233yf、HCFO−1232xf、HCFC−1231xf、HCFC−241db、およびHCFC−242dcからなる群から選択される少なくとも1種の追加の化合物とを含む組成物。
- HCFO−1232xfを含む、請求項10に記載の組成物。
- HCFO−1231xfをさらに含む、請求項11に記載の組成物。
- HCFC−244bbと、プロピレン、HCO−1250xf、HCC−260da、HCC−260db、HCC−240aa、HCO−1230xa、HCFO−1233xf、HFO−1243zf、HCFO−1223za、HCFO−1224zb、HFO−1225zc、HCFC−241db、HCFC−242dc、HCFO−1232xf、HCFO−1231xf、およびHCFC−1233yfからなる群から選択される少なくとも1種の追加の化合物とを含む組成物。
- HCFC−243dbおよびHFC−245faからなる群から選択される少なくとも1種の化合物をさらに含む、請求項13に記載の組成物。
- HFをさらに含む、請求項1〜14のいずれか一項に記載の組成物。
- 酸を含まない、請求項1〜14のいずれか一項に記載の組成物。
- 冷却しようとする物体の近くで請求項1〜5および7〜14のいずれかに記載の組成物を蒸発させる工程、およびその後、該組成物を凝縮させる工程を含む、冷却を発生させる方法。
- 加熱しようとする物体の近くで請求項1〜5および7〜14のいずれかに記載の組成物を凝縮させる工程、およびその後、該組成物を蒸発させる工程を含む、熱を発生させる方法。
- (a)発泡性組成物に、請求項1〜5および7〜14のいずれかに記載の組成物を加える工程;ならびに(b)発泡体を成形するのに有効な条件下で発泡性組成物を加工する工程
を含む、発泡体を成形する方法。 - エアゾール容器中活性成分を含む製剤に、噴射剤として機能する請求項1〜5および7〜14のいずれかに記載の組成物を加える工程を含む、エアゾール製品を製造する方法。
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