JP5701205B2 - 2,3−ジクロロ−1,1,1−トリフルオロプロパン、2−クロロ−1,1,1−トリフルオロプロペン、2−クロロ−1,1,1,2−テトラフルオロプロパンまたは2,3,3,3−テトラフルオロプロペンを含む組成物 - Google Patents
2,3−ジクロロ−1,1,1−トリフルオロプロパン、2−クロロ−1,1,1−トリフルオロプロペン、2−クロロ−1,1,1,2−テトラフルオロプロパンまたは2,3,3,3−テトラフルオロプロペンを含む組成物 Download PDFInfo
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Description
ある実施形態において、HFO−1243zfを用いて、フルオロ塩素化により、HCFC−243db、HCFO−1233xf、HCFC−244dbおよび/またはHFO−1234yfを作製してよい。HFO−1243zfは、E.I.DuPont de Nemours and Company(Wilmington,DE,USA)より市販されている。
ある実施形態において、HCFC−243dbを用いて、HCFC−HCFO−1233xf、HCFC−244dbおよび/またはHFO−1234yfをフッ素化により作製することができる。これらの反応を図1に示す。フッ素化反応は、液相または気相で行うことができる。本発明の液相実施形態について、HCFC−243dbとHFの反応は、バッチ、半バッチ、半連続または連続モードで操作される液相リアクタで実施してよい。バッチモードにおいては、出発HCFC−243dbおよびHFは、オートクレーブまたはその他好適な反応容器で混合して、所望の温度まで加熱される。
ある実施形態において、HCFO−1233xfを用いて、HCFC−HCFC−244bbおよび/またはHFO−1234yfをフッ素化により作製してもよい。これらの反応を図1に示す。
ある実施形態において、HCFC−244bbの脱塩化水素化を用いて、HFO−1234yfを作製する。
以下の基本手順は、フッ素化反応の生成物を分析するのに用いる方法の例示である。リアクタからの全流出物の一部を、質量選択検出器を備えたガスクロマトグラフ(GC/MS)を用いて、有機生成物分析のためにオンラインでサンプリングした。ガスクロマトグラフィーでは、不活性カーボン担持のWilmington,DelawareのE.I.du Pont de Nemours and Company(以降「DuPont」)よりKrytox(登録商標)という商標名で販売されている過フッ素化ポリエーテルを含む長さ20フィート(6.1m)×直径1/8インチ(0.32cm)の管を利用した。ヘリウムフローは、30mL/分(5.0×10−7m3/秒)であった。ガスクロマトグラフィー条件は、3分の初期保持期間について60℃の後、6℃/分の速度で200℃までプログラミングされた温度であった。
784.30グラムCr(NO3)3[9(H2O)](1.96モル)および11.64グラムCo(NO3)2[6(H2O)](0.040モル)の溶液を2000mLの脱イオン水中で調製した。溶液を、pHが約8.5に達するまで、950mLの7.4M水性アンモニアで滴下して処理した。スラリーを室温で一晩攪拌してから、110〜120℃で乾燥するまで蒸発させた。乾燥した触媒を、使用前、400℃で24時間空気中でか焼した。
243dbはCF3CHClCH2Cl、
244dbはCF3CHClCH2F、
245cbはCF3CF2CH3、
245faはCF3CH2CHF2 、
1234yfはCF3CF=CH2、
1233xfはCF3CCl=CH2、
1243zfはCH2=CHCF3、
233abはCF3CCl2CH2Cl、
1233zdはE−および/またはZ−CHCl=CHCF3、
226baはCF3CClFCHF2、
1234zeはE−および/またはZ−CHF=CHCF3、
227caはCF3CF2CHF2、
1223xdはE−および/またはZ−CF3CCl=CHCl、
244bbはCF3CFClCH3、
1141はCHF=CH2。
HFO−1243zfのクロロフッ素化
上記したとおりに調製した98%クロム/2%コバルト触媒(21.4グラム、15mL、−12〜+20メッシュ(1.68〜0.84mm))を、流動床サンドバスで加熱した直径5/8”(1.58cm)のInconel(登録商標)(Special Metals Corp.(New Hartford,New York))ニッケル合金リアクタ管に入れた。触媒を、次のとおり、HFによる処理で予備フッ素化した。触媒を45℃〜175℃まで、約1.5時間にわたって、窒素フロー(50cc/分)で加熱した。HFをリアクタに、50cc/分の流量で、1.3時間にわたって、175℃の温度で入れた。リアクタ窒素フローを20cc/分まで減じ、HFフローを80cc/分まで増やし、このフローを0.3時間維持した。リアクタ温度を、400℃まで1時間にわたって徐々に上げた。この期間後、HFおよび窒素フローを停止し、リアクタを所望の操作温度とした。HF蒸気、HFO−1243zfおよびCl2のリアクタへのフローを開始した。リアクタ流出物の一部をオンラインGC/MSにより分析した。
HCFC−243dbのフッ素化
上記したとおりに調製した98%クロム/2%コバルト触媒(21.4グラム、15mL、−12〜+20メッシュ(1.68〜0.84mm))を、流動床サンドバスで加熱した直径5/8”(1.58cm)のInconel(登録商標)ニッケル合金リアクタ管に入れた。触媒を、次のとおり、HFによる処理で予備フッ素化した。触媒を45℃〜175℃まで、約1.5時間にわたって、窒素フロー(50cc/分)で加熱した。HFをリアクタに、50cc/分の流量で、1.3時間にわたって、175℃の温度で入れた。リアクタ窒素フローを20cc/分まで減じ、HFフローを80cc/分まで増やし、このフローを0.3時間維持した。リアクタ温度を、400℃まで1時間にわたって徐々に上げた。この期間後、HFおよび窒素フローを停止し、リアクタを所望の操作温度とした。HF蒸気、HCFC−243db(CF3CHClCH2Cl)のリアクタへのフローを開始した。リアクタ流出物の一部をオンラインGC/MSにより分析した。
TaF5を存在させたHFC−243dbとHFの反応
210mLのHastelloy(登録商標)C管に、10.0グラム(0.0599モル)のHCFC−243dbおよび25.4グラム(0.040モル)の五フッ化タンタルを入れた。次に、管に、40.0グラム(2.0モル)のフッ化水素を入れた。管を150℃まで温め、149℃〜150℃に8時間、振とうしながら保持した。管を、室温まで冷やし、100mLの水で処理した。管の中身を出し、小有機相を集め、中和した。試料は、91.1%の未変換HCFC−243dbであり、変換生成物のGC−MS分析は次のとおりであった。
HCFO−1233xfからHCFC−244bbへのフッ素化
20グラムの粘性SbF5の入った小PTFEバイアルの中身を、乾燥400mLのHastelloy(登録商標)振とう管に注いだ。漏れ試験のために、管を閉じ、窒素で加圧した。振とう管を−40℃未満までドライアイスで冷やし、徐々に放出してから排気した。75グラム(3.75−モル)の無水HF、次に、165グラム(1.26−モル)のHCFO−1233xfを振とう管へ凝縮した。振とう管をバリケードに入れ、振とうを開始した。
HCFC−244bbへのHCFO−1233xfのフッ素化
20グラムの粘性SbF5の入った小PTFEバイアルの中身を、乾燥400−mLのHastelloy(登録商標)振とう管に入れた。管を閉じ、漏れ試験のために窒素で加圧した。振とう管を、−40℃未満まで、ドライアイスで冷やし、徐々に放出してから排気した。53グラム(2.65−モル)の無水HFを振とう管に移してから、227グラム(1.74モル)のHCFO−1233xfを冷却した振とう管へ凝縮した。振とう管をバリケードに入れ、振とうを開始した。
実施例15は、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)への触媒なしでの変換を示すものである。
実施例16は、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)への触媒なしでの変換を示すものである。
実施例17は、HCFC−244bb(2−クロロ−1,1,1,2−テトラフルオロプロパン)の活性カーボン触媒を存在させた脱塩化水素化を示すものである。
本発明は以下の実施の態様を含むものである。
1.HFO−1234yfと、HFO−1234ze、HFO−1243zf、HCFC−243db、HCFC−244db、HFC−245cb、HFC−245fa、HCFO−1233xf、HCFO−1233zd、HCFC−253fb、HCFC−234ab、HCFC−243fa、エチレン、HFC−23、CFC−13、HFC−143a、HFC−152a、HFC−236fa、HCO−1130、HCO−1130a、HFO−1336、HCFC−133a、HCFC−254fb、HCFC−1131、HFO−1141、HCFO−1242zf、HCFO−1223xd、HCFC−233ab、HCFC−226baおよびHFC−227caからなる群から選択される少なくとも1つの追加の化合物とを含む組成物。
2.約1重量パーセント未満の前記少なくとも1つの追加の化合物を含有する請求項1に記載の組成物。
3.HCFC−243dbと、エチレン、HFC−23、CFC−13、HFC−143a、HFC−152a、HFO−1234yf、HFO−1243zf、HFC−236fa、HCO−1130、HCO−1130a、HFO−1234ze、HFO−1336、HCFC−244bb、HCFC−244db、HFC−245fa、HFC−245cb、HCFC−133a、HCFC−254fb、HCFC−1131、HCFO−1233xf、HCFO−1233zd、HCFO−1242zf、HCFC−253fb、HCFO−1223xd、HCFC−233ab、HCFC−226baおよびHFC−227caからなる群から選択される少なくとも1つの追加の化合物とを含む組成物。
4.HCFO−1233xfと、HCFO−1233zd、HCFO−1232xd、HCFO−1223xd、HCFC−253fb、HCFC−233ab、HFO−1234yf、HFO−1234ze、エチレン、HFC−23、CFC−13、HFC−143a、HFC−152a、HFO−1243zf、HFC−236fa、HCO−1130、HCO−1130a、HFO−1336、HCFC−244bb、HCFC−244db、HFC−245fa、HFC−245cb、HCFC−133a、HCFC−254fb、HCFC−1131、HCFO−1242zf、HCFO−1223xd、HCFC−233ab、HCFC−226baおよびHFC−227caからなる群から選択される少なくとも1つの追加の化合物とを含む組成物。
5.HCFC−244bbと、HCFO−1233zd、HCFO−1232xd、HCFO−1223xd、HCFC−253fb、HCFC−233ab、HFO−1234yf、HFO−1234ze、エチレン、HFC−23、CFC−13、HFC−143a、HFC−152a、HFO−1243zf、HFC−236fa、HCO−1130、HCO−1130a、HFO−1336、HCFC−244db、HFC−245fa、HFC−245cb、HFC−245eb、HCFC−133a、HCFC−254fb、HCFC−1131、HCFO−1242zf、HCFO−1223xd、HCFC−233ab、HCFC−226baおよびHFC−227caからなる群から選択される少なくとも1つの追加の化合物とを含む組成物。
Claims (8)
- HFO−1234yfと、
ゼロ重量パーセントを超え1重量パーセント未満の、HFO−1243zfおよびHFC−245cbと、
を含む、熱伝達組成物、冷媒、エアロゾル噴霧剤、または発泡剤に用いられる組成物。 - HFO−1234ze、HCFC−243db、HCFC−244db、HFC−245fa、HCFO−1233xf、HCFO−1233zd、HCFC−253fb、HCFC−234ab、HCFC−243fa、エチレン、HFC−23、CFC−13、HFC−143a、HFC−152a、HFC−236fa、HCO−1130、HCO−1130a、HFO−1336、HCFC−133a、HCFC−254fb、HCFC−1131、HFO−1141、HCFO−1242zf、HCFO−1223xd、HCFC−233ab、HCFC−226baおよびHFC−227caからなる群から選択される少なくとも1つの追加の化合物をさらに含み、
HFO−1243zfおよびHFC−245cbと前記追加の化合物の合計量が1重量パーセント未満である、
請求項1に記載の組成物。 - 冷媒としての請求項1または2に記載の組成物の使用。
- 空調、冷凍庫、冷蔵庫、ヒートポンプ、水冷器、満液式蒸発冷却器、直接膨張冷却器、遠心分離冷却器、ウォークインクーラー、可動式冷蔵庫、可動式空調ユニットおよびこれらの組み合わせにおける冷媒としての請求項1または2に記載の組成物の使用。
- エアロゾル噴霧剤としての請求項1または2に記載の組成物の使用。
- 発泡剤としての請求項1または2に記載の組成物の使用。
- 熱を熱源からヒートシンクへ伝える組成物を含む請求項1または2に記載の組成物を用いる方法。
- 液体から気体まで相転移し、戻る組成物を含むサイクルにおいて冷媒として請求項1または2に記載の組成物を用いる方法。
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