JP6134470B2 - クロロ−3,3,3−トリフルオロプロペンによる安定した処方系 - Google Patents
クロロ−3,3,3−トリフルオロプロペンによる安定した処方系 Download PDFInfo
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- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
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- C09K23/017—Mixtures of compounds
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/008—Lubricant compositions compatible with refrigerants
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
- C10M2203/065—Well-defined aromatic compounds used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
- C10M2209/043—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/09—Characteristics associated with water
- C10N2020/097—Refrigerants
- C10N2020/101—Containing Hydrofluorocarbons
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- Combustion & Propulsion (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Description
本発明において、HCFO−1233zd(トランス−および/またはシス−アイソマー)およびHCFO−1233xfは、多くのHCFCおよびCFCと同程度に安定、またはそれよりも大幅に安定していて、より環境に優しく、意外なことに、安定剤を添加する必要なく、貯蔵および使用中安定しているということを知見した。
前述した手順に従って、潤滑油および金属の存在下でのトランス−HCFO−1233zdの相溶性および安定性を、高温で、ステンレス鋼オートクレーブにおいて試験した。3つの別のオートクレーブで試験した潤滑剤は、AB−150、MO−150およびPOE−22であった。第4のオートクレーブでは、トランス−HCFO−1233zdを、参照試料として用いるべく、潤滑剤、水分または金属チップなしで試験した。元のHCFO−1233zdは、主にHFO−1234zeおよびHFC−245faである不純物を1〜2%含んでおり、前述したとおり、GCスキャンから差し引いた。
HCFO−1233zdをHCFC−141bに変えた以外は、実施例1の手順に従って、潤滑油および金属の存在下でのHCFC−141bの相溶性および安定性を、高温で、ステンレス鋼オートクレーブにおいて試験した。HCFC−141bは、約0.02%のアルファ−メチルスチレンを安定剤として含有していた。参照試料から取られたHCFC−141bは、99.9%を超えるかなり純粋なもののままであった。HCFC−141bは、潤滑油、金属および水分の存在下では、かなり分解の兆候を示し、数多くの分解生成物、例えば、1,1−ジクロロエチレンが見られ、特に、1−クロロ−1−フルオロエチレン(HCFO−1131a)のレベルが、参照試料については15ppm未満であったのが、油を含む試料については、1500ppmを超える、さらには3300ppmを超える大幅な増大が見られた。これらの結果を表1に示す。潤滑剤を含有するステンレス鋼オートクレーブは、他の金属と接触した領域において、大幅な変色(暗色化)または腐食を示した。この腐食は、単に擦ったり洗ったりするだけでは取り除けなかった。この種の腐食は実施例1では観察されなかった。比較例2は、HCFC−141bを安定化させて分解を阻止するときでも、HCFO−1233zdが、HCFC−141bと少なくとも同じ程度安定であることを示している。
以下の修正を行い、実施例1および比較例3と同様にして、潤滑油の存在下で、トランス−HCFO−1233zdおよびHCFC−141bの相溶性および安定性を試験した。実施例3および4では、2つのオートクレーブを、実施例1で行ったのと同じようにして、それぞれMO−150およびPOE−22と共にHCFO−1233zdにより準備した。比較例5および6では、2つのオートクレーブを、比較例2で行ったのと同じようにして、それぞれMO−150およびPOE−22と共にHCFC−141bにより準備した。オートクレーブを140℃に、48時間でなく96時間、維持した。各オートクレーブの蒸気空間をサンプリングして、安定性試験前後の両方で、GC/MSにより試験した。結果を表2に示す。
トランス−およびシス−アイソマーを約7:3の比率で含有するHCFO−1233zdの試料を、透明なガラスバイアルに、未制御の周囲条件で、10年間にわたり貯蔵した。貯蔵期間後、試料を目視により観察し、GC分析により試験した。試料は依然として透明で変化のないように見え、GC分析によれば、試料組成に大きな変化は示されなかった。本実施例によれば、HCFO−1233zdは、長期の貯蔵条件において安定であることが分かる。
R11の試料を、30ガロンの鋼ドラムに1981年から貯蔵した。貯蔵期間後、試料は黄変し、強い異臭を放った。この例によれば、HCFO−1233zdは、貯蔵および使用において、特に、活性金属、潤滑剤および水分の存在下で、R−11より安定であることが分かる。
B−サイドポリオール処方物におけるHCFO−1233zdおよびHFO−1234zeの化学的および熱的安定性を、以下のようにして、ステンレス鋼オートクレーブ内で試験した。
1)CF3−CH=CHF→CF3−C≡CH+HF
2)HF+SiMe3(OsiMe2)nOSiMe3→SiFMe3+nSiF2Me2+H2O
Claims (1)
- 鋼、ステンレス鋼、アルミニウム、鉄、銅からなる群から選択される金属、及び水の存在下での冷媒組成物の使用であって、
前記組成物は:
1−クロロ−3,3,3−トリフルオロプロペンと;
鉱油、アルキルベンゼン油、及びポリオールエステル油からなる群から選択される潤滑剤とを
含む組成物であり、
前記組成物は、140℃で48時間、鋼、ステンレス鋼、アルミニウム、鉄、銅およびこれらの混合物からなる群から選択される金属及び水に曝した後、99%超の前記1−クロロ−3,3,3−トリフルオロプロペンを維持する該組成物である、該使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US3451308P | 2008-03-07 | 2008-03-07 | |
US61/034,513 | 2008-03-07 | ||
PCT/US2009/036267 WO2009114397A2 (en) | 2008-03-07 | 2009-03-06 | Stable formulated systems with chloro-3,3,3-trifluoropropene |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
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JP2014043110A Division JP2014148675A (ja) | 2008-03-07 | 2014-03-05 | クロロ−3,3,3−トリフルオロプロペンによる安定した処方系 |
JP2017024179A Division JP6503388B2 (ja) | 2008-03-07 | 2017-02-13 | クロロ−3,3,3−トリフルオロプロペンによる安定した処方系 |
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JP2010531926A JP2010531926A (ja) | 2010-09-30 |
JP6134470B2 true JP6134470B2 (ja) | 2017-05-24 |
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JP2010515297A Active JP6134470B2 (ja) | 2008-03-07 | 2009-03-06 | クロロ−3,3,3−トリフルオロプロペンによる安定した処方系 |
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US (4) | US20110001080A1 (ja) |
EP (1) | EP2250144A4 (ja) |
JP (1) | JP6134470B2 (ja) |
CN (1) | CN101808966A (ja) |
WO (1) | WO2009114397A2 (ja) |
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US10072192B2 (en) | 2018-09-11 |
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WO2009114397A2 (en) | 2009-09-17 |
EP2250144A2 (en) | 2010-11-17 |
US20140103248A1 (en) | 2014-04-17 |
EP2250144A4 (en) | 2014-06-04 |
WO2009114397A3 (en) | 2010-01-14 |
US20110001080A1 (en) | 2011-01-06 |
JP2010531926A (ja) | 2010-09-30 |
CN101808966A (zh) | 2010-08-18 |
US9254468B2 (en) | 2016-02-09 |
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