CN101528887B - 氟烯烃用的环氧化物和氟化环氧化物稳定剂 - Google Patents
氟烯烃用的环氧化物和氟化环氧化物稳定剂 Download PDFInfo
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- CN101528887B CN101528887B CN200780032617.XA CN200780032617A CN101528887B CN 101528887 B CN101528887 B CN 101528887B CN 200780032617 A CN200780032617 A CN 200780032617A CN 101528887 B CN101528887 B CN 101528887B
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- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- AGRBXKCSGCUXST-UHFFFAOYSA-N tert-butyl 7-amino-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1=C(N)C=C2CN(C(=O)OC(C)(C)C)CCC2=C1 AGRBXKCSGCUXST-UHFFFAOYSA-N 0.000 description 1
- 230000006209 tert-butylation Effects 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
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- VELSFHQDWXAPNK-UHFFFAOYSA-N tetracontacyclo[25.6.5.516,28.44,32.35,11.321,34.28,10.212,15.222,35.229,31.113,20.124,38.02,6.014,19.017,25.018,23.030,37.033,36.547,54.446,53.448,58.126,51.150,52.03,45.07,42.09,61.039,40.041,43.044,63.049,76.055,78.056,62.057,68.059,64.060,67.065,69.066,71.070,73.072,75.074,77]octaheptaconta-1,3(45),4(48),5(61),6,8,10,12,14,16,18,20,22,24(39),25,27(38),28,30,32,34(42),35(40),36,41(43),44(63),46,49(76),50(77),51,53,55(78),56(62),57,59,64,66,68,70(73),71,74-nonatriacontaene Chemical compound c12c3c4c5c6c1c1c7c8c2c2c3c3c9c4c4c5c5c%10c%11c%12c%13c%14c%15c%12c%12c%16c%17c%18c%19c%20c%21c%17c%17c%22c%21c%21c%23c%20c%20c%19c%19c%24c%18c%16c%15c%15c%24c%16c(c7c%15c%14c1c6c5%13)c8c1c2c2c3c3c(c%21c5c%22c(c%11c%12%17)c%10c4c5c93)c%23c2c%20c1c%19%16 VELSFHQDWXAPNK-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical class [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
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- WVPGXJOLGGFBCR-UHFFFAOYSA-N trioctyl phosphate Chemical compound CCCCCCCCOP(=O)(OCCCCCCCC)OCCCCCCCC WVPGXJOLGGFBCR-UHFFFAOYSA-N 0.000 description 1
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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
- 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
- C09K5/045—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 containing only fluorine as halogen
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
- F25B39/00—Evaporators; Condensers
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Abstract
本发明涉及包含至少一种氟烯烃和有效量的稳定剂的组合物,该稳定剂可以是环氧化物、氟化环氧化物或氧杂环丁烷,或其与其它稳定剂的混合物。该稳定化组合物可用在冷却装置,如制冷、空调、冷却器和热泵中,以及用在如发泡剂、溶剂、气溶胶推进剂、灭火剂和灭菌剂的用途中。
Description
发明背景
1.发明领域
本发明涉及包含至少一种氟烯烃和稳定剂的组合物。该稳定化组合物可作为具有较高全球变暖潜势的现有制冷剂的替代品用在冷却系统中。
2.相关技术描述
关于工作流体的新环境规章已推动制冷和空调工业寻找具有低全球变暖潜势(GWP)的新型工作流体。
正在寻找具有低GWP、无毒性、不可燃性、合理成本和优异制冷性能的替代工作流体。
氟烯烃已经被提出单独或在混合物中作为工作流体。但是,已经观察到,氟烯烃暴露在高温下时或在与其它化合物(例如湿气、氧或可能与它们发生缩合反应的其它化合物)接触时会表现出降解。当氟烯烃用作传热设备(例如制冷或空调设备)中的工作流体时或当用在某些其它用途中时,可能发生这种降解。这种降解可通过许多不同机制发生。在一种情况下,该降解可能由该化合物在极端温度下的不稳定性引起。在另一些情况下,该降解可能由在无意泄漏到该系统中的空气存在下的氧化引起。无论这种降解的原因如何,由于氟烯烃的不稳定性,将这些氟烯烃掺入制冷或空调系统可能不切实际。因此,为了利用氟烯烃的许多其它属性,需要降低降解的手段。
发明概述
本公开提供了包含至少一种氟烯烃和有效量的稳定剂的组合物,该稳定剂包含:
a.至少一种选自环氧化物和式A所示的氟化环氧化物的化合物,其中R2至R5各自是H、具有1至6个碳原子的烷基或具有1至6个碳原子的氟烷基,条件是R2至R5中的至少一个是氟烷基;
和
b.至少一种选自硫代磷酸酯、丁基化三苯基硫代磷酸酯(triphenylphosphorothionates)、有机磷酸酯、富勒烯、芳基烷基醚、官能化全氟聚醚、聚氧烷基化芳族化合物、烷基化芳族化合物、氧杂环丁烷、抗坏血酸、硫醇、内酯、硫醚、胺、硝基甲烷、烷基硅烷、二苯甲酮衍生物、芳基硫醚、对苯二甲酸二乙烯酯、对苯二甲酸二苯酯及其混合物的化合物。
还提供了一种组合物,包含:
a.至少一种氟烯烃;和
b.有效量的稳定剂,其包含:
i)至少一种环氧化物、氟化环氧化物或其混合物;
ii)至少一种亚磷酸酯、酚、萜烯、萜类化合物或其混合物;和
iii)至少一种选自草酰双(亚苄基)酰肼(areoxalyl bis(benzylidene)hydrazide);N,N’-双(3,5-二叔丁基-4-羟基氢化肉桂酰肼);2,2’-草酰氨基双-乙基-(3,5-二叔丁基-4-羟基氢化肉桂酸酯(hydorcinnamate));N,N’-(二亚水杨基)-1,2-丙二胺;乙二胺四乙酸及其盐;三唑;苯并三唑、2-巯基苯并噻唑、甲苯三唑(tolutriazole)衍生物、N,N-二亚水杨基-1,2-二氨基丙烷及其混合物的金属钝化剂。
还提供了使包含至少一种氟烯烃的组合物稳定化的方法,所述方法包括添加有效量的稳定剂,所述稳定剂包含至少一种环氧化物或氟化环氧化物和至少一种选自硫代磷酸酯、丁基化三苯基硫代磷酸酯、有机磷酸酯、富勒烯、芳基烷基醚、官能化全氟聚醚、聚氧烷基化芳族化合物、烷基化芳族化合物、氧杂环丁烷、抗坏血酸、硫醇、内酯、硫醚、胺、硝基甲烷、烷基硅烷、二苯甲酮衍生物、芳基硫醚、对苯二甲酸二乙烯酯、对苯二甲酸二苯酯及其混合物的化合物。
还提供了降低包含至少一种氟烯烃的组合物的降解的方法,其中所述降解由制冷、空调或热泵系统中误入空气的存在引起,所述方法包括将有效量的稳定剂添加到包含至少一种氟烯烃的组合物中,所述稳定剂 包含至少一种环氧化物或氟化环氧化物和至少一种选自硫代磷酸酯、丁基化三苯基硫代磷酸酯、有机磷酸酯、富勒烯、芳基烷基醚、官能化全氟聚醚、聚氧烷基化芳族化合物、烷基化芳族化合物、氧杂环丁烷、抗坏血酸、硫醇、内酯、硫醚、胺、硝基甲烷、烷基硅烷、二苯甲酮衍生物、芳基硫醚、对苯二甲酸二乙烯酯、对苯二甲酸二苯酯及其混合物的化合物。
还提供了减少包含至少一种氟烯烃的组合物与氧反应的方法,所述方法包括将有效量的稳定剂添加到包含至少一种氟烯烃的组合物中,所述稳定剂包含至少一种环氧化物或氟化环氧化物和至少一种选自硫代磷酸酯、丁基化三苯基硫代磷酸酯、有机磷酸酯、富勒烯、芳基烷基醚、官能化全氟聚醚、聚氧烷基化芳族化合物、烷基化芳族化合物、氧杂环丁烷、抗坏血酸、硫醇、内酯、硫醚、胺、硝基甲烷、烷基硅烷、二苯甲酮衍生物、芳基硫醚、对苯二甲酸二乙烯酯、对苯二甲酸二苯酯及其混合物的化合物。
发明详述
本发明提供了包含至少一种氟烯烃和有效量的包含至少一种环氧化物或氟化环氧化物的稳定剂的组合物。
这些组合物在工作流体中具有多种用途,仅举几个例子,包括用作发泡剂、起泡剂、灭火剂、传热介质(如用在制冷系统、冰箱、空调系统、热泵、冷却器等中的传热流体和制冷剂)。
发泡剂是使聚合物基质膨胀形成多孔结构的挥发性组合物。
溶剂是从基材上除去污物或将材料沉积到基材上或负载材料的流体。
气溶胶推进剂是施加大于一大气压的压力以将材料从容器中推出的一种或多种组分的挥发性组合物。
灭火剂是熄灭或抑制火焰的挥发性组合物。
灭菌剂是破坏生物活性材料或类似物的挥发性生物杀灭流体或含挥发性生物杀灭流体的共混物。
传热介质(本文中也称作传热流体、传热组合物或传热流体组合物)是用于将热从热源传向散热器的工作流体。
制冷剂是在流体经历从液体到气体并回到液体的相变的周期中充当传热流体的化合物或化合物混合物。
本文所用的术语氟烯烃描述了包含碳原子、氟原子和任选氢原子的化合物。在一个实施方案中,本发明的组合物中所用的氟烯烃包含具有2至12个碳原子的化合物。在另一实施方案中,氟烯烃包含具有3至10个碳原子的化合物,且在再一实施方案中,氟烯烃包含具有3至7个碳原子的化合物。代表性氟烯烃包括但不限于表1、表2和表3中所列的所有化合物。
本发明的一个实施方案提供了具有式E-或Z-R1CH=CHR2(式I)的氟烯烃,其中R1和R2独立地为C1至C6全氟烷基。R1和R2基团的实例包括但不限于CF3、C2F5、CF2CF2CF3、CF(CF3)2、CF2CF2CF2CF3、CF(CF3)CF2CF3、CF2CF(CF3)2、C(CF3)3、CF2CF2CF2CF2CF3、CF2CF2CF(CF3)2、C(CF3)2C2F5、CF2CF2CF2CF2CF2CF3、CF(CF3)CF2CF2C2F5和C(CF3)2CF2C2F5。在一个实施方案中,式I的氟烯烃在分子中具有至少约4个碳原子。在另一实施方案中,式I的氟烯烃在分子中具有至少约5个碳原子。示例性的非限制性式I化合物列在表1中。
表1
代码 | 结构 | 化学名称 |
F11E | CF3CH=CHCF3 | 1,1,1,4,4,4-六氟丁-2-烯 |
F12E | CF3CH=CHC2F5 | 1,1,1,4,4,5,5,5-八氟戊-2-烯 |
F13E | CF3CH=CHCF2C2F5 | 1,1,1,4,4,5,5,6,6,6-十氟己-2-烯 |
F13iE | CF3CH=CHCF(CF3)2 | 1,1,1,4,5,5,5-七氟-4-(三氟甲基)戊-2-烯 |
F22E | C2F5CH=CHC2F5 | 1,1,1,2,2,5,5,6,6,6-十氟己-3-烯 |
F14E | CF3CH=CH(CF2)3CF3 | 1,1,1,4,4,5,5,6,6,7,7,7-十二氟庚-2-烯 |
F14iE | CF3CH=CHCF2CF-(CF3)2 | 1,1,1,4,4,5,6,6,6-九氟-5-(三氟甲基)己-2-烯 |
F14sE | CF3CH=CHCF(CF3)-C2F5 | 1,1,1,4,5,5,6,6,6-九氟-4-(三氟甲基)己-2-烯 |
F14tE | CF3CH=CHC(CF3)3 | 1,1,1,5,5,5-六氟-4,4-双(三氟甲基)戊-2-烯 |
F23E | C2F5CH=CHCF2C2F5 | 1,1,1,2,2,5,5,6,6,7,7,7-十二氟庚-3-烯 |
F23iE | C2F5CH=CHCF(CF3)2 | 1,1,1,2,2,5,6,6,6-九氟-5-(三氟甲基)己-3-烯 |
F15E | CF3CH=CH(CF2)4CF3 | 1,1,1,4,4,5,5,6,6,7,7,8,8,8-十四氟辛-2-烯 |
F15iE | CF3CH=CH-CF2CF2CF(CF3)2 | 1,1,1,4,4,5,5,6,7,7,7-十一氟-6-(三氟甲基)庚-2-烯 |
F15tE | CF3CH=CH-C(CF3)2C2F5 | 1,1,1,5,5,6,6,6-八氟-4,4-双(三氟甲基)己-2-烯 |
F24E | C2F5CH=CH(CF2)3CF3 | 1,1,1,2,2,5,5,6,6,7,7,8,8,8-十四氟辛-3-烯 |
F24iE | C2F5CH=CHCF2CF-(CF3)2 | 1,1,1,2,2,5,5,6,7,7,7-十一氟-6-(三氟甲基)庚-3-烯 |
F24sE | C2F5CH=CHCF(CF3)-C2F5 | 1,1,1,2,2,5,6,6,7,7,7-十一氟-5-(三氟甲基)庚-3-烯 |
F24tE | C2F5CH=CHC(CF3)3 | 1,1,1,2,2,6,6,6-八氟-5,5-双(三氟甲基)己-3-烯 |
F33E | C2F5CF2CH=CH-CF2C2F5 | 1,1,1,2,2,3,3,6,6,7,7,8,8,8-十四氟辛-4-烯 |
F3i3iE | (CF3)2CFCH=CH-CF(CF3)2 | 1,1,1,2,5,6,6,6-八氟-2,5-双(三氟甲基)己-3-烯 |
F33iE | C2F5CF2CH=CH-CF(CF3)2 | 1,1,1,2,5,5,6,6,7,7,7-十一氟-2-(三氟甲基)庚-3-烯 |
F16E | CF3CH=CH(CF2)5CF3 | 1,1,1,4,4,5,5,6,6,7,7,8,8,,9,9,9-十六氟壬-2-烯 |
F16sE | CF3CH=CHCF(CF3)(CF2)2C2F5 | 1,1,1,4,5,5,6,6,7,7,8,8,8-十三氟-4-(三氟甲基)庚 -2-烯 |
F16tE | CF3CH=CHC(CF3)2CF2C2F5 | 1,1,1,6,6,6-八氟-4,4-双(三氟甲基)庚-2-烯 |
F25E | C2F5CH=CH(CF2)4CF3 | 1,1,1,2,2,5,5,6,6,7,7,8,8,9,9,9-十六氟壬-3-烯 |
F25iE | C2F5CH=CH-CF2CF2CF(CF3)2 | 1,1,1,2,2,5,5,6,6,7,8,8,8-十三氟-7-(三氟甲基)辛 -3-烯 |
F25tE | C2F5CH=CH-C(CF3)2C2F5 | 1,1,1,2,2,6,6,7,7,7-十氟-5,5-双(三氟甲基)庚-3-烯 |
F34E | C2F5CF2CH=CH-(CF2)3CF3 | 1,1,1,2,2,3,3,6,6,7,7,8,8,9,9,9-十六氟壬-4-烯 |
F34iE | C2F5CF2CH=CH-CF2CF(CF3)2 | 1,1,1,2,2,3,3,6,6,7,8,8,8-十三氟-7-(三氟甲基)辛 -4-烯 |
F34sE | C2F5CF2CH=CH-CF(CF3)C2F5 | 1,1,1,2,2,3,3,6,7,7,8,8,8-十三氟-6-(三氟甲基)辛 -4-烯 |
F34tE | C2F5CF2CH=CH-C(CF3)3 | 1,1,1,5,5,6,6,7,7,7-十氟-2,2-双(三氟甲基)庚-3-烯 |
F3i4E | (CF3)2CFCH=CH-(CF2)3CF3 | 1,1,1,2,5,5,6,6,7,7,8,8,8-十三氟-2(三氟甲基)辛 -3-烯 |
F3i4iE | (CF3)2CFCH=CH-CF2CF(CF3)2 | 1,1,1,2,5,5,6,7,7,7-十氟-2,6-双(三氟甲基)庚-3-烯 |
F3i4sE | (CF3)2CFCH=CH-CF(CF3)C2F5 | 1,1,1,2,5,6,6,7,7,7-十氟-2,5-双(三氟甲基)庚-3-烯 |
F3i4tE | (CF3)2CFCH=CH-C(CF3)3 | 1,1,1,2,6,6,6-七氟-2,5,5-三(三氟甲基)己-3-烯 |
F26E | C2F5CH=CH(CF2)5CF3 | 1,1,1,2,2,5,5,6,6,7,7,8,8,9,9,10,10,10-十八氟癸 -3-烯 |
F26sE | C2F5CH=CHCF(CF3)(CF2)2C2F5 | 1,1,1,2,2,5,6,6,7,7,8,8,9,9,9-十五氟-5-(三氟甲 基)壬-3-烯 |
F26tE | C2F5CH=CHC(CF3)2CF2C2F5 | 1,1,1,2,2,6,6,7,7,8,8,8-十二氟-5,5-双(三氟甲基) 辛-3-烯 |
F35E | C2F5CF2CH=CH-(CF2)4CF3 | 1,1,1,2,2,3,3,6,6,7,7,8,8,9,9,10,10,10-十八氟癸 -4-烯 |
F35iE | C2F5CF2CH=CH-CF2CF2CF(CF3)2 | 1,1,1,2,2,3,3,6,6,7,7,8,9,9,9-十五氟-8-(三氟甲 基)壬-4-烯 |
F35tE | C2F5CF2CH=CH-C(CF3)2C2F5 | 1,1,1,2,2,3,3,7,7,8,8,8-十二氟-6,6-双(三氟甲基) 辛-4-烯 |
F3i5E | (CF3)2CFCH=CH-(CF2)4CF3 | 1,1,1,2,5,5,6,6,7,7,8,8,9,9,9-十五氟-2-(三氟甲 基)壬-3-烯 |
F3i5iE | (CF3)2CFCH=CH-CF2CF2CF(CF3)2 | 1,1,1,2,5,5,6,6,7,8,8,8-十二氟-2,7-双(三氟甲基) 辛-3-烯 |
F3i5tE | (CF3)2CFCH=CH-C(CF3)2C2F5 | 1,1,1,2,6,6,7,7,7-九氟-2,5,5-三(三氟甲基)庚-3-烯 |
F44E | CF3(CF2)3CH=CH-(CF2)3CF3 | 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-十八氟癸 -5-烯 |
F44iE | CF3(CF2)3CH=CH-CF2CF(CF3)2 | 1,1,1,2,3,3,6,6,7,7,8,8,9,9,9-十五氟-2-(三氟甲 基)壬-4-烯 |
F44sE | CF3(CF2)3CH=CH-CF(CF3)C2F5 | 1,1,1,2,2,3,6,6,7,7,8,8,9,9,9-十五氟-3-(三氟甲 基)壬-4-烯 |
F44tE | CF3(CF2)3CH=CH-C(CF3)3 | 1,1,1,5,5,6,6,7,7,8,8,8-十二氟-2,2,-双(三氟甲 基)辛-3-烯 |
F4i4iE | (CF3)2CFCF2CH=CH-CF2CF(CF3)2 | 1,1,1,2,3,3,6,6,7,8,8,8-十二氟-2,7-双(三氟甲基) 辛-4-烯 |
F4i4sE | (CF3)2CFCF2CH=CH-CF(CF3)C2F5 | 1,1,1,2,3,3,6,7,7,8,8,8-十二氟-2,6-双(三氟甲基) 辛-4-烯 |
F4i4tE | (CF3)2CFCF2CH=CH-C(CF3)3 | 1,1,1,5,5,6,7,7,7-九氟-2,2,6-三(三氟甲基)庚-3-烯 |
F4s4sE | C2F5CF(CF3)CH=CH-CF(CF3)C2F5 | 1,1,1,2,2,3,6,7,7,8,8,8-十二氟-3,6-双(三氟甲基) 辛-4-烯 |
F4s4tE | C2F5CF(CF3)CH=CH-C(CF3)3 | 1,1,1,5,6,6,7,7,7-九氟-2,2,5-三(三氟甲基)庚-3-烯 |
F4t4tE | (CF3)3CCH=CH-C(CF3)3 | 1,1,1,6,6,6-六氟-2,2,5,5-四(三氟甲基)己-3-烯 |
式I的化合物可以通过使式R1I的全氟烷基碘与式R2CH=CH2的全氟烷基三氢烯烃接触以形成式R1CH2CHIR2的三氢碘代全氟链烷来制 备。这种三氢碘代全氟链烷可以随后脱碘化氢以形成R1CH=CHR2。或者,该烯烃R1CH=CHR2可以通过式R1CHICH2R2的三氢碘代全氟链烷的脱碘化氢来制备,后者又通过使式R2I的全氟烷基碘与式R1CH=CH2的全氟烷基三氢烯烃反应形成。
全氟烷基碘与全氟烷基三氢烯烃的所述接触可以通过在能够在反应物和产物自压下在反应温度下运行的合适反应容器中混合反应物来以分批模式进行。合适的反应容器包括由不锈钢,特别是奥氏体型不锈钢,和公知的高镍合金,如 镍-铜合金、 镍基合金和 镍-铬合金制成。
或者,该反应可以以半分批模式进行,其中在反应温度下借助合适的加料装置如泵将全氟烷基三氢烯烃反应物添加到全氟烷基碘反应物中。
全氟烷基碘与全氟烷基三氢烯烃的比率应该为约1∶1至约4∶1,优选约1.5∶1至2.5∶1。如Jeanneaux等人在Journal of Fluorine Chemistry,第4卷,第261-270页(1974)中所报道,小于1.5∶1的比率往往产生大量2∶1加合物。
使所述全氟烷基碘与所述全氟烷基三氢烯烃接触的优选温度优选为约150℃至300℃,优选约170℃至约250℃,最优选约180℃至约230℃。
全氟烷基碘与全氟烷基三氢烯烃的反应的合适接触时间为约0.5小时至18小时,优选约4至约12小时。
通过全氟烷基碘与全氟烷基三氢烯烃的反应制成的三氢碘代全氟链烷可直接用在脱碘化氢步骤中或可以优选在脱碘化氢步骤之前通过蒸馏回收和提纯。
脱碘化氢步骤通过使三氢碘代全氟链烷与碱性物质接触来进行。合适的碱性物质包括碱金属氢氧化物(例如氢氧化钠或氢氧化钾)、碱金属氧化物(例如氧化钠)、碱土金属氢氧化物(例如氢氧化钙)、碱土金属氧化物(例如氧化钙)、碱金属醇盐(例如甲醇钠或乙醇钠)、氨水、氨基化钠、或碱性物质的混合物,如碱石灰。优选的碱性物质是氢氧化钠和氢氧化钾。
三氢碘代全氟链烷与碱性物质的所述接触可以在液相中优选在能够溶解至少一部分这两种反应物的溶剂存在下进行。适用于脱碘化氢步 骤的溶剂包括一种或多种极性有机溶剂,如醇(例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇和叔丁醇)、腈(例如乙腈、丙腈、丁腈、苄腈或己二腈)、二甲亚砜、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺或环丁砜。溶剂的选择可以取决于产物沸点和在提纯过程中从产物中分离痕量溶剂的简易性。通常,乙醇或异丙醇是该反应的良溶剂。
通常,脱碘化氢反应可以通过在合适的反应容器中将反应物之一(碱性物质或三氢碘代全氟链烷)添加到另一反应物中来进行。所述反应器可以由玻璃、陶瓷或金属制成并优选用叶轮或搅拌装置搅动。
适用于脱碘化氢反应的温度为约10℃至约100℃,优选约20℃至约70℃。脱碘化氢反应可以在环境压力或在减压或高压下进行。要指出的是其中式I的化合物在其形成时从反应容器中馏出的脱碘化氢反应。
或者,脱碘化氢反应可以通过使所述碱性物质的水溶液与三氢碘代全氟链烷在一种或多种具有较低极性的有机溶剂中的溶液在相转移催化剂存在下接触来进行,所述有机溶剂如链烷(例如己烷、庚烷或辛烷)、芳烃(例如甲苯)、卤代烃(例如二氯甲烷、氯仿、四氯化碳或全氯乙烯)、或醚(例如二乙醚、甲基叔丁醚、四氢呋喃、2-甲基四氢呋喃、二氧杂环己烷、二甲氧基乙烷、二甘醇二甲醚或四甘醇二甲醚)。合适的相转移催化剂包括季铵卤化物(例如溴化四丁铵、硫酸氢四丁铵、氯化三乙基苄基铵、氯化十二烷基三甲铵和氯化三辛酰基甲铵)、季鏻卤化物(例如溴化三苯基甲基鏻和氯化四苯基鏻)或本领域中被称作冠醚的环状聚醚化合物(例如18-冠-6和15-冠-5)。
或者,脱碘化氢反应可以在不存在溶剂的情况下通过将三氢碘代全氟链烷添加到固体或液体碱性物质中来进行。
根据反应物的溶解度,脱碘化氢反应的合适反应时间为约15分钟至约6小时或更久。通常,脱碘化氢反应迅速并且需要约30分钟至约3小时完成。
可以通过添加水后的相分离、通过蒸馏或通过其组合从脱碘化氢反应混合物中回收式I的化合物。
在本发明的另一实施方案中,氟烯烃包含环氟烯烃(环-[CX=CY(CZW)n-](式II),其中X、Y、Z和W独立地选自H和F,且n为2至5的整数)。在一个实施方案中,式II的氟烯烃在分子中具有至少约3个碳原子。在另一实施方案中,式II的氟烯烃在分子中具有至少 约4个碳原子。在再一实施方案中,式II的氟烯烃在分子中具有至少约5个碳原子。式II的代表性环氟烯烃列在表2中。
表2
环氟烯烃 | 结构 | 化学名称 |
FC-C1316cc | 环-CF2CF2CF=CF- | 1,2,3,3,4,4-六氟环丁烯 |
HFC-C1334cc | 环-CF2CF2CH=CH- | 3,3,4,4-四氟环丁烯 |
HFC-C1436 | 环-CF2CF2CF2CH=CH- | 3,3,4,4,5,5,-六氟环戊烯 |
FC-C1418y | 环-CF2CF=CFCF2CF2- | 1,2,3,3,4,4,5,5-八氟环戊烯 |
FC-C151-10y | 环-CF2CF=CFCF2CF2CF2- | 1,2,3,3,4,4,5,5,6,6-十氟环己烯 |
本发明的组合物可以包含单一的式I或式II的化合物,例如表1或表2中的化合物之一,或可以包含式I或式II的化合物的组合。
在另一实施方案中,氟烯烃可以包含表3中所列的那些化合物。
表3
名称 | 结构 | 化学名称 |
HFC-1225ye | CF3CF=CHF | 1,2,3,3,3-五氟-1-丙烯 |
HFC-1225zc | CF3CH=CF2 | 1,1,3,3,3-五氟-1-丙烯 |
HFC-1225yc | CHF2CF=CF2 | 1,1,2,3,3-五氟-1-丙烯 |
HFC-1234ye | CHF2CF=CHF | 1,2,3,3-四氟-1-丙烯 |
HFC-1234yf | CF3CF=CH2 | 2,3,3,3-四氟-1-丙烯 |
HFC-1234ze | CF3CH=CHF | 1,3,3,3-四氟-1-丙烯 |
HFC-1234yc | CH2FCF=CF2 | 1,1,2,3-四氟-1-丙烯 |
HFC-1234zc | CHF2CH=CF2 | 1,1,3,3-四氟-1-丙烯 |
HFC-1243yf | CHF2CF=CH2 | 2,3,3-三氟-1-丙烯 |
HFC-1243zf | CF3CH=CH2 | 3,3,3-三氟-1-丙烯 |
HFC-1243yc | CH3CF=CF2 | 1,1,2-三氟-1-丙烯 |
HFC-1243zc | CH2FCH=CF2 | 1,1,3-三氟-1-丙烯 |
HFC-1243ye | CH2FCF=CHF | 1,2,3-三氟-1-丙烯 |
HFC-1243ze | CHF2CH=CHF | 1,3,3-三氟-1-丙烯 |
FC-1318my | CF3CF=CFCF3 | 1,1,1,2,3,4,4,4-八氟-2-丁烯 |
FC-1318cy | CF3CF2CF=CF2 | 1,1,2,3,3,4,4,4-八氟-1-丁烯 |
HFC-1327my | CF3CF=CHCF3 | 1,1,1,2,4,4,4-七氟-2-丁烯 |
HFC-1327ye | CHF=CFCF2CF3 | 1,2,3,3,4,4,4-七氟-1-丁烯 |
HFC-1327py | CHF2CF=CFCF3 | 1,1,1,2,3,4,4-七氟-2-丁烯 |
HFC-1327et | (CF3)2C=CHF | 1,3,3,3-四氟-2-(三氟甲基)-1-丙烯 |
HFC-1327cz | CF2=CHCF2CF3 | 1,1,3,3,4,4,4-七氟-1-丁烯 |
HFC-1327cye | CF2=CFCHFCF3 | 1,1,2,3,4,4,4-七氟-1-丁烯 |
HFC-1327cyc | CF2=CFCF2CHF2 | 1,1,2,3,3,4,4-七氟-1-丁烯 |
HFC-1336yf | CF3CF2CF=CH2 | 2,3,3,4,4,4-六氟-1-丁烯 |
HFC-1336ze | CHF=CHCF2CF3 | 1,3,3,4,4,4-六氟-1-丁烯 |
HFC-1336eye | CHF=CFCHFCF3 | 1,2,3,4,4,4-六氟-1-丁烯 |
HFC-1336eyc | CHF=CFCF2CHF2 | 1,2,3,3,4,4-六氟-1-丁烯 |
HFC-1336pyy | CHF2CF=CFCHF2 | 1,1,2,3,4,4-六氟-2-丁烯 |
HFC-1336qy | CH2FCF=CFCF3 | 1,1,1,2,3,4-六氟-2-丁烯 |
HFC-1336pz | CHF2CH=CFCF3 | 1,1,1,2,4,4-六氟-2-丁烯 |
HFC-1336mzy | CF3CH=CFCHF2 | 1,1,1,3,4,4-六氟-2-丁烯 |
HFC-1336qc | CF2=CFCF2CH2F | 1,1,2,3,3,4-六氟-1-丁烯 |
HFC-1336pe | CF2=CFCHFCHF2 | 1,1,2,3,4,4-六氟-1-丁烯 |
HFC-1336ft | CH2=C(CF3)2 | 3,3,3-三氟-2-(三氟甲基)-1-丙烯 |
HFC-1345qz | CH2FCH=CFCF3 | 1,1,1,2,4-五氟-2-丁烯 |
HFC-1345mzy | CF3CH=CFCH2F | 1,1,1,3,4-五氟-2-丁烯 |
HFC-1345fz | CF3CF2CH=CH2 | 3,3,4,4,4-五氟-1-丁烯 |
HFC-1345mzz | CHF2CH=CHCF3 | 1,1,1,4,4-五氟-2-丁烯 |
HFC-1345sy | CH3CF=CFCF3 | 1,1,1,2,3-五氟-2-丁烯 |
HFC-1345fyc | CH2=CFCF2CHF2 | 2,3,3,4,4-五氟-1-丁烯 |
HFC-1345pyz | CHF2CF=CHCHF2 | 1,1,2,4,4-五氟-2-丁烯 |
HFC-1345cyc | CH3CF2CF=CF2 | 1,1,2,3,3-五氟-1-丁烯 |
HFC-1345pyy | CH2FCF=CFCHF2 | 1,1,2,3,4-五氟-2-丁烯 |
HFC-1345eyc | CH2FCF2CF=CF2 | 1,2,3,3,4-五氟-1-丁烯 |
HFC-1345ctm | CF2=C(CF3)(CH3) | 1,1,3,3,3-五氟-2-甲基-1-丙烯 |
HFC-1345ftp | CH2=C(CHF2)(CF3) | 2-(二氟甲基)-3,3,3-三氟-1-丙烯 |
HFC1345fye | CH2=CFCHFCF3 | 2,3,4,4,4-五氟-1-丁烯 |
HFC-1345eyf | CHF=CFCH2CF3 | 1,2,4,4,4-五氟-1-丁烯 |
HFC-1345eze | CHF=CHCHFCF3 | 1,3,4,4,4-五氟-1-丁烯 |
HFC-1345ezc | CHF=CHCF2CHF2 | 1,3,3,4,4-五氟-1-丁烯 |
HFC-1345eye | CHF=CFCHFCHF2 | 1,2,3,4,4-五氟-1-丁烯 |
HFC-1354fzc | CH2=CHCF2CHF2 | 3,3,4,4-四氟-1-丁烯 |
HFC-1354ctp | CF2=C(CHF2)(CH3) | 1,1,3,3-四氟-2-甲基-1-丙烯 |
HFC-1354etm | CHF=C(CF3)(CH3) | 1,3,3,3-四氟-2-甲基-1-丙烯 |
HFC-1354tfp | CH2=C(CHF2)2 | 2-(二氟甲基)-3,3-二氟-1-丙烯 |
HFC-1354my | CF3CF=CHCH3 | 1,1,1,2-四氟-2-丁烯 |
HFC-1354mzy | CH3CF=CHCF3 | 1,1,1,3-四氟-2-丁烯 |
FC-141-10myy | CF3CF=CFCF2CF3 | 1,1,1,2,3,4,4,5,5,5-十氟-2-戊烯 |
FC-141-10cy | CF2=CFCF2CF2CF3 | 1,1,2,3,3,4,4,5,5,5-十氟-1-戊烯 |
HFC-1429mzt | (CF3)2C=CHCF3 | 1,1,1,4,4,4-六氟-2-(三氟甲基)-2-丁烯 |
HFC-1429myz | CF3CF=CHCF2CF3 | 1,1,1,2,4,4,5,5,5-九氟-2-戊烯 |
HFC-1429mzy | CF3CH=CFCF2CF3 | 1,1,1,3,4,4,5,5,5-九氟-2-戊烯 |
HFC-1429eyc | CHF=CFCF2CF2CF3 | 1,2,3,3,4,4,5,5,5-九氟-1-戊烯 |
HFC-1429czc | CF2=CHCF2CF2CF3 | 1,1,3,3,4,4,5,5,5-九氟-1-戊烯 |
HFC-1429cycc | CF2=CFCF2CF2CHF2 | 1,1,2,3,3,4,4,5,5-九氟-1-戊烯 |
HFC-1429pyy | CHF2CF=CFCF2CF3 | 1,1,2,3,4,4,5,5,5-九氟-2-戊烯 |
HFC-1429myyc | CF3CF=CFCF2CHF2 | 1,1,1,2,3,4,4,5,5-九氟-2-戊烯 |
HFC-1429myye | CF3CF=CFCHFCF3 | 1,1,1,2,3,4,5,5,5-九氟-2-戊烯 |
HFC-1429eyym | CHF=CFCF(CF3)2 | 1,2,3,4,4,4-六氟-3-(三氟甲基)-1-丁烯 |
HFC-1429cyzm | CF2=CFCH(CF3)2 | 1,1,2,4,4,4-六氟-3-(三氟甲基)-1-丁烯 |
HFC-1429mzt | CF3CH=C(CF3)2 | 1,1,1,4,4,4-六氟-2-(三氟甲基)-2-丁烯 |
HFC-1429czym | CF2=CHCF(CF3)2 | 1,1,3,4,4,4-六氟-3-(三氟甲基)-1-丁烯 |
HFC-1438fy | CH2=CFCF2CF2CF3 | 2,3,3,4,4,5,5,5-八氟-1-戊烯 |
HFC-1438eycc | CHF=CFCF2CF2CHF2 | 1,2,3,3,4,4,5,5-八氟-1-戊烯 |
HFC-1438ftmc | CH2=C(CF3)CF2CF3 | 3,3,4,4,4-五氟-2-(三氟甲基)-1-丁烯 |
HFC-1438czzm | CF2=CHCH(CF3)2 | 1,1,4,4,4-五氟-3-(三氟甲基)-1-丁烯 |
HFC-1438ezym | CHF=CHCF(CF3)2 | 1,3,4,4,4-五氟-3-(三氟甲基)-1-丁烯 |
HFC-1438ctmf | CF2=C(CF3)CH2CF3 | 1,1,4,4,4-五氟-2-(三氟甲基)-1-丁烯 |
HFC-1447fzy | (CF3)2CFCH=CH2 | 3,4,4,4-四氟-3-(三氟甲基)-1-丁烯 |
HFC-1447fz | CF3CF2CF2CH=CH2 | 3,3,4,4,5,5,5-七氟-1-戊烯 |
HFC-1447fycc | CH2=CFCF2CF2CHF2 | 2,3,3,4,4,5,5-七氟-1-戊烯 |
HFC-1447czcf | CF2=CHCF2CH2CF3 | 1,1,3,3,5,5,5-七氟-1-戊烯 |
HFC-1447mytm | CF3CF=C(CF3)(CH3) | 1,1,1,2,4,4,4-七氟-3-甲基-2-丁烯 |
HFC-1447fyz | CH2=CFCH(CF3)2 | 2,4,4,4-四氟-3-(三氟甲基)-1-丁烯 |
HFC-1447ezz | CHF=CHCH(CF3)2 | 1,4,4,4-四氟-3-(三氟甲基)-1-丁烯 |
HFC-1447qzt | CH2FCH=C(CF3)2 | 1,4,4,4-四氟-2-(三氟甲基)-2-丁烯 |
HFC-1447syt | CH3CF=C(CF3)2 | 2,4,4,4-四氟-2-(三氟甲基)-2-丁烯 |
HFC-1456szt | (CF3)2C=CHCH3 | 3-(三氟甲基)-4,4,4-三氟-2-丁烯 |
HFC-1456szy | CF3CF2CF=CHCH3 | 3,4,4,5,5,5-六氟-2-戊烯 |
HFC-1456mstz | CF3C(CH3)=CHCF3 | 1,1,1,4,4,4-六氟-2-甲基-2-丁烯 |
HFC-1456fzce | CH2=CHCF2CHFCF3 | 3,3,4,5,5,5-六氟-1-戊烯 |
HFC-1456ftmf | CH2=C(CF3)CH2CF3 | 4,4,4-三氟-2-(三氟甲基)-1-丁烯 |
FC-151-12c | CF3(CF2)3CF=CF2 | 1,1,2,3,3,4,4,5,5,6,6,6-十二氟-1-己烯(或全 氟-1-己烯) |
FC-151-12mcy | CF3CF2CF=CFCF2CF3 | 1,1,1,2,2,3,4,5,5,6,6,6-十二氟-3-己烯(或全 氟-3-己烯) |
FC-151-12mmtt | (CF3)2C=C(CF3)2 | 1,1,1,4,4,4-六氟-2,3-双(三氟甲基)-2-丁烯 |
FC-151-12mmzz | (CF3)2CFCF=CFCF3 | 1,1,1,2,3,4,5,5,5-九氟-4-(三氟甲基)-2-戊烯 |
HFC-152-11mmtz | (CF3)2C=CHC2F5 | 1,1,1,4,4,5,5,5-八氟-2-(三氟甲基)-2-戊烯 |
HFC-152-11mmyyz | (CF3)2CFCF=CHCF3 | 1,1,1,3,4,5,5,5-八氟-4-(三氟甲基)-2-戊烯 |
PFBE (或HFC-1549fz) | CF3CF2CF2CF2CH=CH2 | 3,3,4,4,5,5,6,6,6-九氟-1-己烯(或全氟丁基乙 烯) |
HFC-1549fztmm | CH2=CHC(CF3)3 | 4,4,4-三氟-3,3-双(三氟甲基)-1-丁烯 |
HFC-1549mmtts | (CF3)2C=C(CH3)(CF3) | 1,1,1,4,4,4-六氟-3-甲基-2-(三氟甲基)-2-丁烯 |
HFC-1549fycz | CH2=CFCF2CH(CF3)2 | 2,3,3,5,5,5-六氟-4-(三氟甲基)-1-戊烯 |
HFC-1549myts | CF3CF=C(CH3)CF2CF3 | 1,1,1,2,4,4,5,5,5-九氟-3-甲基-2-戊烯 |
HFC-1549mzzz | CF3CH=CHCH(CF3)2 | 1,1,1,5,5,5-六氟-4-(三氟甲基)-2-戊烯 |
HFC-1558szy | CF3CF2CF2CF=CHCH3 | 3,4,4,5,5,6,6,6-八氟-2-己烯 |
HFC-1558fzccc | CH2=CHCF2CF2CF2CHF2 | 3,3,4,4,5,5,6,6-八氟-2-己烯 |
HFC-1558mmtzc | (CF3)2C=CHCF2CH3 | 1,1,1,4,4-五氟-2-(三氟甲基)-2-戊烯 |
HFC-1558ftmf | CH2=C(CF3)CH2C2F5 | 4,4,5,5,5-五氟-2-(三氟甲基)-1-戊烯 |
HFC-1567fts | CF3CF2CF2C(CH3)=CH2 | 3,3,4,4,5,5,5-七氟-2-甲基-1-戊烯 |
HFC-1567szz | CF3CF2CF2CH=CHCH3 | 4,4,5,5,6,6,6-七氟-2-己烯 |
HFC-1567fzfc | CH2=CHCH2CF2C2F5 | 4,4,5,5,6,6,6-七氟-1-己烯 |
HFC-1567sfyy | CF3CF2CF=CFC2H5 | 1,1,1,2,2,3,4-七氟-3-己烯 |
HFC-1567fzfy | CH2=CHCH2CF(CF3)2 | 4,5,5,5-四氟-4-(三氟甲基)-1-戊烯 |
HFC-1567myzzm | CF3CF=CHCH(CF3)(CH3) | 1,1,1,2,5,5,5-七氟-4-甲基-2-戊烯 |
HFC-1567mmtyf | (CF3)2C=CFC2H5 | 1,1,1,3-四氟-2-(三氟甲基)-2-戊烯 |
FC-161-14myy | CF3CF=CFCF2CF2C2F5 | 1,1,1,2,3,4,4,5,5,6,6,7,7,7-十四氟-2-庚烯 |
FC-161-14mcyy | CF3CF2CF=CFCF2C2F5 | 1,1,1,2,2,3,4,5,5,6,6,7,7,7-十四氟-2-庚烯 |
HFC-162-13mzy | CF3CH=CFCF2CF2C2F5 | 1,1,1,3,4,4,5,5,6,6,7,7,7-十三氟-2-庚烯 |
HFC162-13myz | CF3CF=CHCF2CF2C2F5 | 1,1,1,2,4,4,5,5,6,6,7,7,7-十三氟-2-庚烯 |
HFC-162-13mczy | CF3CF2CH=CFCF2C2F5 | 1,1,1,2,2,4,5,5,6,6,7,7,7-十三氟-3-庚烯 |
HFC-162-13mcyz | CF3CF2CF=CHCF2C2F5 | 1,1,1,2,2,3,5,5,6,6,7,7,7-十三氟-3-庚烯 |
PEVE | CF2=CFOCF2CF3 | 全氟乙基三氟乙烯基醚 |
PMVE | CF2=CFOCF3 | 三氟甲基三氟乙烯基醚 |
表2和表3中所列的化合物可购得或可通过本领域已知的或如本文所述的方法制备。
1,1,1,4,4-五氟-2-丁烯可以由1,1,1,2,4,4-六氟丁烷(CHF2CH2CHFCF3)通过在固体KOH上在气相中在室温下脱氟化氢来制备。在引入本文作为参考的US 6,066,768中描述了1,1,1,2,4,4-六氟丁烷的合成。
1,1,1,4,4,4-六氟-2-丁烯可以由1,1,1,4,4,4-六氟-2-碘丁烷(CF3CHICH2CF3)通过使用相转移催化剂在约60℃下与KOH反应来制备。1,1,1,4,4,4-六氟-2-碘丁烷的合成可以通过全氟甲基碘(CF3I)和3,3,3-三氟丙烯(CF3CH=CH2)在约200℃下在自压下反应约8小时来进行。
3,4,4,5,5,5-六氟-2-戊烯可以通过使用固体KOH或在碳催化剂上在200-300℃下1,1,1,2,2,3,3-七氟戊烷(CF3CF2CF2CH2CH3)的脱氟化氢来制备。1,1,1,2,2,3,3-七氟戊烷可以通过3,3,4,4,5,5,5-七氟-1-戊烯(CF3CF2CF2CH=CH2)的氢化制备。
1,1,1,2,3,4-六氟-2-丁烯可以通过使用固体KOH的1,1,1,2,3,3,4-七氟丁烷(CH2FCF2CHFCF3)的脱氟化氢来制备。
1,1,1,2,4,4-六氟-2-丁烯可以通过使用固体KOH的1,1,1,2,2,4,4-七氟丁烷(CHF2CH2CF2CF3)的脱氟化氢来制备。
1,1,1,3,4,4-六氟2-丁烯可以通过使用固体KOH的1,1,1,3,3,4,4-七氟丁烷(CF3CH2CF2CHF2)的脱氟化氢来制备。
1,1,1,2,4-五氟-2-丁烯可以通过使用固体KOH的1,1,1,2,2,3-六氟丁烷(CH2FCH2CF2CF3)的脱氟化氢来制备。
1,1,1,3,4-五氟-2-丁烯可以通过使用固体KOH的1,1,1,3,3,4-六氟丁烷(CF3CH2CF2CH2F)的脱氟化氢来制备。
1,1,1,3-四氟-2-丁烯可以通过使1,1,1,3,3-五氟丁烷(CF3CH2CF2CH3)与KOH水溶液在120℃下反应制备。
1,1,1,4,4,5,5,5-八氟-2-戊烯可以由(CF3CHICH2CF2CF3)通过使用相转移催化剂在约60℃下与KOH反应来制备。4-碘-1,1,1,2,2,5,5,5-八氟戊烷的合成可以通过全氟乙基碘(CF3CF2I)和3,3,3-三氟丙烯在约200℃下在自压下反应约8小时来进行。
1,1,1,2,2,5,5,6,6,6-十氟-3-己烯可以由1,1,1,2,2,5,5,6,6,6-十氟-3-碘己烷(CF3CF2CHICH2CF2CF3)通过使用相转移催化剂在约60℃下与KOH反应来制备。1,1,1,2,2,5,5,6,6,6-十氟-3-碘己烷的合成可以通过全氟乙基碘(CF3CF2I)和3,3,4,4,4-五氟-1-丁烯(CF3CF2CH=CH2)在约200℃下在自压下反应约8小时来进行。
1,1,1,4,5,5,5-七氟-4-(三氟甲基)-2-戊烯可以通过在异丙醇中用KOH将1,1,1,2,5,5,5-七氟-4-碘-2-(三氟甲基)-戊烷(CF3CHICH2CF(CF3)2)脱氟化氢来制备。CF3CHICH2CF(CF3)2由(CF3)2CFI与CF3CH=CH2在高温,例如约200℃下的反应制造。
1,1,1,4,4,5,5,6,6,6-十氟-2-己烯可以通过1,1,1,4,4,4-六氟-2-丁烯(CF3CH=CHCF3)与四氟乙烯(CF2=CF2)和五氟化锑(SbF5)的反应制备。
2,3,3,4,4-五氟-1-丁烯可以通过1,1,2,2,3,3-六氟丁烷在氟化氧化铝上 在升高温度下的脱氟化氢制备。
2,3,3,4,4,5,5,5-八氟-1-戊烯可以通过2,2,3,3,4,4,5,5,5-九氟戊烷在固体KOH上的脱氟化氢制备。
1,2,3,3,4,4,5,5-八氟-1-戊烯可以通过2,2,3,3,4,4,5,5,5-九氟戊烷在氟化氧化铝上在升高温度下的脱氟化氢制备。
式I、式II、表1、表2和表3的许多化合物作为不同的构型异构体或立体异构体存在。在没有指定特定异构体时,本发明拟包括所有单一的构型异构体、单一的立体异构体或其任何组合。例如,F11E意在代表E-异构体、Z-异构体或这两种异构体的任何比例的任何组合或混合物。作为另一实例,HFC-1225ye意在代表E-异构体、Z-异构体或这两种异构体的任何比例的任何组合或混合物。
本发明提供了包含至少一种氟烯烃和有效量的稳定剂的组合物,该稳定剂包含:a.至少一种环氧化物或氟化环氧化物;和b.至少一种选自硫代磷酸酯、丁基化三苯基硫代磷酸酯、有机磷酸酯、富勒烯、芳基烷基醚、官能化全氟聚醚、聚氧烷基化芳族化合物、烷基化芳族化合物、氧杂环丁烷、抗坏血酸、硫醇、内酯、硫醚、胺、硝基甲烷、烷基硅烷、二苯甲酮衍生物、芳基硫醚、对苯二甲酸二乙烯酯、对苯二甲酸二苯酯及其混合物的化合物。
在一个实施方案中,本发明的稳定剂包含至少一种环氧化物。环氧化物包括1,2-环氧丙烷(CAS reg.no.[75-56-9])、1,2-环氧丁烷(CAS reg.no.[106-88-7])、丁基苯基缩水甘油醚、戊基苯基缩水甘油醚、己基苯基缩水甘油醚、庚基苯基缩水甘油醚、辛基苯基缩水甘油醚、壬基苯基缩水甘油醚、癸基苯基缩水甘油醚、缩水甘油基甲基苯基醚、1,4-缩水甘油基苯基二醚、4-甲氧基苯基缩水甘油醚、萘基缩水甘油醚、1,4-二缩水甘油基萘基二醚、丁基苯基缩水甘油醚、正丁基缩水甘油醚、异丁基缩水甘油醚、己二醇二缩水甘油醚、烯丙基缩水甘油醚、聚丙二醇二缩水甘油醚及其混合物。
在另一实施方案中,本发明的稳定剂包含至少一种氟化环氧化物。本发明的氟化环氧化物稳定剂可以由式A描绘,其中R2至R5各自是H、具有1至6个碳原子的烷基或具有1至6个碳原子的氟烷基,条件是R2至R5中的至少一个是氟烷基。
式A
代表性的氟化环氧化物稳定剂包括但不限于三氟甲基环氧乙烷和1,1-双(三氟甲基)环氧乙烷。这类化合物可以通过本领域已知的方法,例如通过Journal of Fluorine Chemistry,第24卷,第93-104页(1984), Journal of Organic Chemistry,第56卷,第3187至3189页(1991)和 Journal of Fluorine Chemistry,第125卷,第99-105页(2004)中所述的方法制备。
本发明的组合物另外包含选自不同种类化合物的化合物。这种附加稳定剂选自硫代磷酸酯、丁基化三苯基硫代磷酸酯、有机磷酸酯、富勒烯、官能化全氟聚醚、聚氧烷基化芳族化合物、烷基化芳族化合物、氧杂环丁烷、抗坏血酸、硫醇、内酯、硫醚、胺、硝基甲烷、烷基硅烷、二苯甲酮衍生物、芳基硫醚、对苯二甲酸二乙烯酯和对苯二甲酸二苯酯及其混合物,是指这段中所列的任何稳定剂的混合物,以及这段中所列的任何稳定剂或稳定剂组合与上述环氧化物或氟化环氧化物稳定剂中的任何稳定剂或组合的混合物。
在一个实施方案中,本发明的稳定剂包含至少一种硫代磷酸酯。本发明的硫代磷酸酯稳定剂是由磷酸通过用二价硫取代一个或多个氧原子而生成的化合物。这些可以是单硫代磷酸酯、二硫代磷酸酯或更高级的。代表性的二硫代磷酸酯可以以商标 63购自Ciba SpecialtyChemicals of Basel,Switzerland(下文称作“Ciba”)。在另一实施方案中,硫代磷酸酯包括二烷基硫代磷酸酯。代表性的二烷基硫代磷酸酯稳定剂可以以商标 353购自Ciba。
在另一实施方案中,本发明的稳定剂包含至少一种如式B所示的丁基化三苯基硫代磷酸酯
式B
各R独立地选自H或叔丁基的丁基化三苯基硫代磷酸酯的一个实例可以以商标 232购自Ciba。
在另一实施方案中,本发明的稳定剂包含至少一种有机磷酸酯。该有机磷酸酯稳定剂包括但不限于胺磷酸酯、磷酸三烷基酯、磷酸三芳基酯、混合烷基-芳基磷酸酯(烷基二芳基、二烷基芳基或烷基化芳基)和环状磷酸酯。代表性的胺磷酸酯可以以商标 349购自Ciba。代表性的磷酸三烷基酯包括:磷酸三甲酯((CH3)3PO4,Cas reg.no.512-56-1);磷酸三乙酯((CH3CH2)3PO4,Cas reg.no.78-40-0);磷酸三丁酯((C4H9)3PO4,CAS reg.no.126-73-8);磷酸三辛酯((C8H17)3PO4,CAS reg.no.1806-54-8);和磷酸三(2-乙基己基)酯((CH3CH(C2H5)(CH2)4)3PO4,CASreg.no.78-42-2)。代表性的磷酸三芳基酯包括:磷酸三苯酯((C6H5O)3PO,CAS reg.no.115-86-6);磷酸三甲苯酯(TCP,(CH3C6H4O)3PO,CAS reg.no.1330-78-5);和磷酸三二甲苯酯(((CH3)2C6H3O)3PO,CAS reg.no.25155-23-1)。代表性的混合烷基-芳基磷酸酯包括:磷酸异丙基苯基苯酯(IPPP,(C6H5O)2((CH3)2CHO)PO,CAS reg.no.68782-95-6)和磷酸双(叔丁基苯基)苯酯(TBPP,(C6H5O)2((CH3)3C)PO,CAS reg.no.65652-41-7)。这类磷化合物可获自许多化学供应商,如Aldrich(Milwaukee,Wisconsin);Alfa Aesar(Ward Hill,MA);或Akzo Nobel(Arnhem,the Netherlands)。代表性的市售烷基化三芳基磷酸酯包括可以以商标Syn-O- 8784购自Akzo Nobel(Arnhem,the Netherlands)的丁基化三苯基磷酸酯;可以以商标 620购自Great Lakes Chemical Corporation(GLCC,WestLafayette,IN)的叔丁基化三苯基磷酸酯;和可以以商标 220和110也购自GLCC的异丙基化三苯基磷酸酯。
在另一实施方案中,本发明的稳定剂包含至少一种富勒烯。富勒烯是作为部分经由五边形彼此连接的六边碳环(苯)键合的封闭碳笼。顶点数(a,碳原子)与六边碳环数(n)(五边环始终为12个)之间的关系通过:a =2(n+10)给出。尽管该公式适用于所有理论结构,但只有具有相对较低应力和形变的那些分子稳定。代表性的富勒烯包括但不限于Buckminsterfullerene(C60或“巴基球”,CAS reg.no.[99685-96-8])和[5,6]富勒烯-C70(C70,CAS reg.no.[115383-22-7])、富勒烯-C76(CAS reg.no.[135113-15-4])、富勒烯-C78(CAS reg.no.[136316-32-0])和富勒烯-C84(CAS reg.no.[135113-16-5])。
在另一实施方案中,本发明的稳定剂包含至少一种芳基烷基醚。本发明的芳基烷基醚稳定剂可以由式C描绘,其中n是1、2或3且R1是具有1至16个碳原子的烷基。
式C
代表性的芳基烷基醚包括但不限于苯甲醚、1,4-二甲氧基苯、1,4-二乙氧基苯和1,3,5-三甲氧基苯。
在另一实施方案中,本发明的稳定剂包含至少一种官能化全氟聚醚。这类官能化全氟聚醚可以是含全氟聚醚-或全氟烷基并且含磷的部分酯化的磷酸芳基酯、膦酸芳基酯及其盐,其如美国专利No.6,184,187和其中的参考文献中所述(i)在磷和氟碳基团之间含有单-或多-环氧烷连接基,或(ii)在磷和氟碳基团之间不含连接基。
在另一实施方案中,该官能化全氟聚醚稳定剂可以是含有全氟烷基或全氟聚醚侧链的上式C所示的化合物。此外,如2005年6月17日提交的美国专利申请No.11/156,348中所述,该官能化全氟聚醚稳定剂可以是包含全氟聚醚链段和一个或多个具有通式-CH2(CqH2q)OH的醇链段的全氟聚醚烷基醇,其中-CqH2q代表二价直链或支链烷基,其中q是0至约10的整数。
在另一实施方案中,如2006年6月27日提交的美国专利申请No.11/167,330中所述,本发明的官能化全氟聚醚稳定剂可以包含具有结构[Rf 1-(CtR(u+v))]mE(O)n(CtR1 (u+v+1))(3-m)的取代芳基磷属元素组合物,其中
Rf 1是具有约400至约15,000的化学式量的氟聚醚链,包含重复单 元,并选自:
(a)J-O-(CF(CF3)CF2O)c(CFXO)dCFZ-;
(b)J1-O-(CF2CF2O)e(CF2O)fCFZ1-;
(c)J2-O-(CF(CF3)CF2O)jCF(CF3)CF2-;
(d)J3-O-(CQ2-CF2CF2-O)k-CQ2-CF2-;
(e)J3-O-(CF(CF3)CF2O)g(CF2CF2O)h(CFXO)i-CFZ-;
(f)J4-O-(CF2CF2O)rCF2-;和
(h)其中两种或多种的组合,
其中
J是选自CF3、C2F5、C3F7、CF2Cl、C2F4Cl、C3F6Cl和其中两种或多种的组合的氟烷基;
c和d的数值使得c∶d的比率为约0.01至约0.5;
X是F、CF3或其组合;
Z是F、Cl或CF3;
J1是选自CF3、C2F5、C3F7、CF2Cl、C2F4Cl和其中两种或多种的组合的氟烷基;
e和f的数值使得e∶f的比率为约0.3至约5;
Z1是F或Cl;
J2是C2F5、C3F7或其组合;
j是平均数以使Rf的化学式量为约400至约15,000;
J3选自CF3、C2F5、C3F7和其中两种或多种的组合;
k是平均数以使Rf的化学式量为约400至约15,000;
各Q独立地为F、Cl或H;
g、h和i的数值使得(g+h)为约1至约50,i∶(g+h)的比率为约0.1至约0.5;
J4是CF3、C2F5或其组合;
r是平均数以使Rf的化学式量为约400至约15,000;且
各R和R1独立地为H、C1-C10烷基、卤素、OR3、OH、SO3M、NR2 2、R3OH、R3SO3M、R3NR2 2、R3NO2、R3CN、C(O)OR3、C(O)OM、C(O)R3或C(O)NR2 2或其中两种或多种的组合;
其中
R2独立地为H、C1-C10烷基、或其中两种或多种的组合;
R3是C1-C10烷基;且
M是氢或金属,优选不是铝;
t等于(6+u);
u是0、2、4、6、8、10、12、14、16的任何组合;
v独立地为2或4;
n是0或1;
E是P、As或Sb;且
m大于约0.5至约3,条件是当E=P、m=3.0且t=6时,R不能完全是H或含有F。
在另一实施方案中,如2005年9月1日提交的美国专利申请No.11/218,259中所述,本发明的官能化全氟聚醚稳定剂可以包含芳基全氟聚醚,其是具有式Rf-(Y)a-(CtR(u+v))-(O-CtR1 (u+v))b-R的单官能芳基全氟聚醚、具有式Rf 1-[(Y)a-(CtR(u+v))-(O-CtR1 (u+v))b-R]2的二官能芳基全氟聚醚或其组合,其中
Rf和Rf 1各自具有约400至约15,000的化学式量;
Rf包含重复单元,该重复单元选自
(a)J-O-(CF(CF3)CF2O)c(CFXO)dCFZ-,
(b)J1-O-(CF2CF2O)e(CF2O)fCFZ1-,
(c)J2-O-(CF(CF3)CF2O)jCF(CF3)-,
(d)J3-O-(CQ2-CF2CF2-O)k-CQ2-,
(e)J3-O-(CF(CF3)CF2O)g(CF2CF2O)h(CFX-O)i-CFZ-,
(f)J4-O-(CF2CF2O)k’CF2-,和
(g)其中两种或多种的组合;且
其中
式CF2CF2O和CF2O的单元沿该链无规分布;
J是CF3、C2F5、C3F7、CF2Cl、C2F4Cl、C3F6Cl或其中两种或多种的组合;
c和d的数值使得c/d的比率为约0.01至约0.5;
X是-F、-CF3或其组合;
Z是-F、-Cl或-CF3;
Z1是-F或-Cl,
J1是CF3、C2F5、C3F7、CF2Cl、C2F4Cl或其中两种或多种的组合;
e和f的数值使得e/f的比率为约0.3至约5;
J2是-C2F5、-C3F7或其组合;
j是平均数以使Rf的化学式量为约400至约15,000;
J3是CF3、C2F5、C3F7或其中两种或多种的组合;
k是平均数以使Rf的化学式量为约400至约15,000;
各Q独立地为-F、-Cl或-H;
g、h和i的数值使得(g+h)为约1至约50,i∶(g+h)的比率为约0.1至约0.5;
J4是CF3、C2F5或其组合;
k’是平均数以使Rf的化学式量为约400至约15,000;
各R独立地为-H、卤素、-OH、-SO3M、NR3 2、-NO2、-R4OH、-R4SO3M、-R4NR3 2、-R4NO2、-R4CN、-C(O)OR4、-C(O)OM、-C(O)R4、-C(O)NR3 2或其中两种或多种的组合;只是当b=0时,R不能是四个氢原子和-OH或-Br或-NH2;或R不能只是H或-NO2或其组合;
各R1独立地为H、-R4、-OR4、卤素、-OH、-SO3M、-NR3 2、-NO2、-CN、-R4OH、-R4SO3M、-R4NR3 2、-R4NO2、-R4CN、-C(O)OR4、-C(O)OM、-C(O)R4、C(O)NR3 2或其中两种或多种的组合,条件是如果b=0,则R和R2的组合不能是四个或更多氢原子和-OH、-Br、-NH2或-NO2;
各R3独立地为H、C1-C10烷基、或其中两种或多种的组合;
R4是C1-C10烷基;
M是氢或金属离子;
a是0或1;
b是0-5;
Y是二价基团-CH2OCH2-、-(CH2)o-O-、-(CF2)n-、-CF2O-、-CF2OCF2-、-C(O)-、-C(S)-或其中两种或多种的组合;
n是约1至约5;
o是约2至约5;
t等于6+u;
u是0、2、4、6、8、10、12、14、16的任何组合;
v独立地为2或4;
Rf1是-(CF2CF2O)e(CF2O)fCF2-、-(C3F6O)p(CF2CF2O)q(CFXO)rCF2-、-(CF2CF2O)(C3F6O)wCF(CF3)-、-CF(CF3)O(C3F6O)w-Rf2-O (C3F6O)wCF(CF3)-、-((CQ2)CF2CF2O)sCF2CF2-或其中两种或多种的组合;
其中
e、f、X和Q如上定义;
p、q和r的数值使得(p+q)为1至50且r/(p+q)为0.1至0.05;
各w独立地为2至45;
Rf2是直链或支链-CmF2m-;
m是1-10;且
s是平均数以使Rf 1的化学式量为400至15,000。
在另一实施方案中,该稳定剂可以包含至少一种聚氧烷基化芳族化合物。该聚氧烷基化芳族化合物是式C所示的化合物,其中R1基团是包含至少一个-CH2CH2O-部分的聚氧烷基化基团。在另一实施方案中,本发明的稳定剂包含至少一种烷基化芳族化合物。代表性的烷基化芳族化合物包括但不限于支链和直链的烷基苯润滑剂,如 75、 150和 500(Shrieve Chemicals出售的直链烷基苯)和HAB 22(Nippon Oil出售的支链烷基苯)。
在另一实施方案中,本发明的稳定剂包含至少一种氧杂环丁烷。本发明的氧杂环丁烷稳定剂可以是带有一个或多个氧杂环丁烷基团的化合物并由式D表示,其中R1-R6相同或不同并且可以选自氢、烷基或取代烷基、芳基或取代芳基。
式D
代表性的氧杂环丁烷稳定剂包括但不限于3-乙基-3-羟甲基-氧杂环丁烷,如OXT-101(Toagosei Co.,Ltd);3-乙基-3-((苯氧基)甲基)-氧杂环丁烷,如OXT-211(Toagosei Co.,Ltd);和3-乙基-3-((2-乙基-己氧基)甲基)-氧杂环丁烷,如OXT-212(Toagosei Co.,Ltd)。
在另一实施方案中,本发明的稳定剂包含抗坏血酸(CAS reg.no.[50-81-7])。
在另一实施方案中,本发明的稳定剂包含至少一种硫醇(thiol)。硫 醇化合物,也称作硫醇(mercaptans)或氢硫化物,是含羟基的醇的硫类似物。代表性的硫醇稳定剂包括但不限于甲硫醇(甲基硫醇)、乙硫醇(乙基硫醇)、辅酶A(CAS reg.no.[85-61-0])、二巯基丁二酸(DMSA,CAS reg.no.[2418-14-6])、葡萄柚硫醇((R)-2-(4-甲基环己-3-烯基)丙-2-硫醇,CASreg.no.[83150-78-1])、半胱氨酸((R)-2-氨基-3-硫烷基-丙酸,CAS reg.no.[52-90-4])和硫辛酰胺(1,2-二硫戊环-3-戊酰胺,CAS reg.no.[940-69-2])。
在另一实施方案中,本发明的稳定剂包含至少一种内酯。内酯是可通过醇基团与相同分子中的羧酸基团反应制成的环酯。本发明的代表性的内酯稳定剂包括但不限于γ-丁内酯(CAS reg.no.[96-48-0])、δ-葡糖酸内酯(CAS reg.no.[90-80-2])、γ-十一内酯(CAS reg.no.[104-67-6])、6,7-二氢-4(5H)-苯并呋喃酮(CAS reg.No.[16806-93-2])和5,7-双(1,1-二甲基乙基)-3-[2,3(或3,4)-二甲基苯基]-2(3H)-苯并呋喃酮(CAS reg.no[201815-03-4]),如 HP-136(Ciba)。
在另一实施方案中,本发明的稳定剂包含至少一种硫醚。本发明的硫醚稳定剂包括但不限于苄基苯基硫醚(CAS reg.no.[831-91-4])、二苯硫醚(CAS reg.no.[139-66-2])、以商标 PS 802(Ciba)购自Ciba和可以以商标 PS 800(Ciba)购自Ciba的二(十二烷基)3,3’-硫代丙酸酯,及其混合物(是指这段中所列的任何硫醚的混合物)。
在另一实施方案中,本发明的稳定剂包含至少一种胺。在一个实施方案中,胺稳定剂包含至少一种选自三乙胺、三丁胺、二异丙胺、三异丙胺、三异丁胺、对苯二胺和二苯基胺的化合物。在另一实施方案中,胺稳定剂包含二烷基胺,包括(N-(1-甲基乙基)-2-丙胺,CAS reg.no.[108-18-9])。在另一实施方案中,胺稳定剂包括受阻胺抗氧化剂。受阻胺抗氧化剂包括衍生自取代哌啶化合物的胺,特别是烷基取代的哌啶基、哌啶子基(piperidinyl)、哌嗪酮或烷氧基哌啶子基化合物的衍生物。代表性的受阻胺抗氧化剂包括2,2,6,6-四甲基-4-哌啶酮;2,2,6,6-四甲基-4-哌啶醇;双-(1,2,2,6,6-五甲基哌啶基)癸二酸酯(CAS reg.no.[41556-26-7]);二-(2,2,6,6-四甲基-4-哌啶基)癸二酸酯,如Ciba以商标 770出售的受阻胺;聚-(N-羟乙基-2,2,6,6-四甲基-4-羟基-哌啶基丁二酸酯(CAS reg.no.[65447-77-0]),如可以以商标 622LD购自Ciba;烷基化对苯二胺,如N-苯基-N’-(1,3-二甲基丁基)-对苯二胺,或N,N’-二仲丁基-对苯二胺;和羟胺,如牛油脂肪胺、或N-甲基双(氢 化牛油烷基)胺。一些其它受阻胺抗氧化剂包括可以以商标 765购自Ciba或以商标 1944和 1770购自Mayzo,Inc.的胺抗氧化剂。胺也包括这段中所列的任何胺的混合物。
在另一实施方案中,本发明的稳定剂包含硝基甲烷(CH3NO2,CASreg.no.[75-52-5])。
在另一实施方案中,本发明的稳定剂包含至少一种烷基硅烷。硅烷是与烃类似的化合物,其中硅原子替代各个碳。烷基硅烷稳定剂包括但不限于双(二甲氨基)甲基硅烷(DMAMS,CAS reg.no.[22705-33-5])、三(三甲基甲硅烷基)硅烷(TTMSS,CAS reg.no.[1873-77-4])、乙烯基三乙氧基硅烷(VTES,CAS reg.no.[78-08-0])和乙烯基三甲氧基硅烷(VTMO,CAS reg.no.[2768-02-7])。
在另一实施方案中,本发明的稳定剂包含至少一种二苯甲酮衍生物。二苯甲酮衍生物稳定剂包含可以被侧基取代的二苯甲酮,所述侧基包括卤化物,如氟、氯、溴或碘,氨基,羟基,烷基,如甲基、乙基或丙基,芳基,如苯基,硝基或这类基团的任何组合。代表性的二苯甲酮衍生物稳定剂包括但不限于:2,5-二氟二苯甲酮;2’,5’-二羟基苯乙酮;2-氨基二苯甲酮;2-氯二苯甲酮;2-氟二苯甲酮;2-羟基二苯甲酮;2-甲基二苯甲酮;2-氨基-4′-氯二苯甲酮;2-氨基-4′-氟二苯甲酮;2-氨基-5-溴-2′-氯二苯甲酮;2-氨基-5-氯二苯甲酮;2-氨基-5-氯-2′-氟二苯甲酮;2-氨基-5-硝基二苯甲酮;2-氨基-5-硝基-2′-氯二苯甲酮;2-氨基-2′,5-二氯二苯甲酮;2-氯-4′-氟二苯甲酮;2-羟基-4-甲氧基二苯甲酮;2-羟基-5-氯二苯甲酮;2-甲氨基-5-氯二苯甲酮;3-甲基二苯甲酮;3-硝基二苯甲酮;3-硝基-4′-氯-4-氟二苯甲酮;4-氯二苯甲酮;4-氟二苯甲酮;4-羟基二苯甲酮;4-甲氧基二苯甲酮;4-甲基二苯甲酮;4-硝基二苯甲酮;4-苯基二苯甲酮;4-氯-3-硝基二苯甲酮;4-羟基-4′-氯二苯甲酮;2,4-二羟基二苯甲酮;2,4-二甲基二苯甲酮;2,5-二甲基二苯甲酮;3,4-二氨基二苯甲酮;3,4-二氯二苯甲酮;3,4-二氟二苯甲酮;3,4-二羟基二苯甲酮;3,4-二甲基二苯甲酮;4,4′-双(二乙胺)二苯甲酮;4,4′-双(二甲基胺)二苯甲酮;4,4′-二氯二苯甲酮;4,4′-二氟二苯甲酮;4,4′-二羟基二苯甲酮;和4,4′-二甲氧基二苯甲酮。
在另一实施方案中,本发明的稳定剂包含至少一种芳基硫醚。该芳基硫醚稳定剂包含至少一种选自苄基苯基硫醚、二苯硫醚和二苄基硫醚 的化合物。
在另一实施方案中,本发明的稳定剂包含至少一种对苯二甲酸酯。该对苯二甲酸酯稳定剂包括对苯二甲酸二乙烯酯(CAS reg.no.[13486-19-0])和对苯二甲酸二苯酯(CAS reg.no.[1539-04-4])。
在一个实施方案中,本发明的组合物进一步包含至少一种选自酚、亚磷酸酯、萜烯、萜类化合物及其混合物的附加稳定剂化合物。
在另一实施方案中,该附加稳定剂可以包含至少一种酚。酚稳定剂包含任何取代或未取代的酚化合物,包括包含一个或多个取代或未取代的环状、直链或支链脂族取代基的酚,如烷基化单酚,包括2,6-二叔丁基-4-甲基苯酚;2,6-二叔丁基-4-乙基苯酚;2,4-二甲基-6-叔丁基苯酚;生育酚;和类似物,氢醌和烷基化氢醌,包括叔丁基氢醌、氢醌的其它衍生物;和类似物,羟基化硫代二苯基醚,包括4,4’-硫代-双(2-甲基-6-叔丁基苯酚);4,4’-硫代双(3-甲基-6-叔丁基苯酚);2,2’-硫代双(4甲基-6-叔丁基苯酚);和类似物,亚烷基-双酚,包括:4,4’-亚甲基双(2,6-二叔丁基苯酚);4,4’-双(2,6-二叔丁基苯酚);2,2’-或4,4-联苯二醇(biphenoldiols)的衍生物;2,2’-亚甲基双(4-乙基-6-叔丁基苯酚);2,2’-亚甲基双(4-甲基-6-叔丁基苯酚);4,4-亚丁基双(3-甲基-6-叔丁基苯酚);4,4-异亚丙基双(2,6-二叔丁基苯酚);2,2’-亚甲基双(4-甲基-6-壬基苯酚);2,2’-异亚丁基双(4,6-二甲基苯酚);2,2’-亚甲基双(4-甲基-6-环己基苯酚)、2,2-或4,4-联苯二醇(biphenyldiols),包括2,2’-亚甲基双(4-乙基-6-叔丁基苯酚);丁基化羟基甲苯(BHT)、包含杂原子的双酚,包括2,6-二-叔-α-二甲氨基-对甲酚、4,4-硫代双(6-叔丁基-间甲酚);和类似物;酰氨基酚;2,6-二叔丁基-4(N,N’-二甲氨基甲基苯酚);硫化物,包括双(3-甲基-4-羟基-5-叔丁基苄基)硫化物;双(3,5-二叔丁基-4-羟基苄基)硫化物;及其混合物(是指这段中所列的任何酚稳定剂的混合物)。
在另一实施方案中,该附加稳定剂可以包含至少一种亚磷酸酯。亚磷酸酯稳定剂可以衍生自取代亚磷酸酯,包括受阻亚磷酸酯。特别地,受阻亚磷酸酯是烷基、芳基或烷基芳基亚磷酸酯化合物的衍生物。受阻亚磷酸酯包括三(二叔丁基苯基)亚磷酸酯、亚磷酸二正辛酯和磷酸异癸基二苯酯。三(二叔丁基苯基)亚磷酸酯以商标 168出售,亚磷酸二正辛酯以商标 OPH出售,且亚磷酸异癸基二苯酯以商标 DDPP出售,均来自Ciba。
在另一实施方案中,该附加稳定剂可以包含至少一种萜烯。萜烯包含以含有多于一个重复异戊二烯(2-甲基-1,3-丁二烯)单元的结构为特征的烃化合物。代表性的萜烯包括但不限于月桂烯(2-甲基-6-亚甲基辛-1,7-二烯)、别罗勒烯、β-罗勒烯、芸香烯、苧烯(特别是d-苧烯)、视黄醛、蒎烯、薄荷醇、香叶醇、法呢醇、植醇、维生素A、萜品烯、δ-3-蒈烯、萜品油烯、水芹烯、葑烯、二戊烯及其混合物(是指这段中所列的任何萜烯稳定剂的混合物)。萜烯稳定剂可购得或可通过本领域已知的方法制备或分离自天然来源。
在另一实施方案中,该附加稳定剂可以包含至少一种萜类化合物。萜类化合物包含以含有多于一个重复异戊二烯单元并且通常含氧的结构为特征的天然产品和相关化合物。代表性的萜类化合物包括类胡萝卜素,如番茄红素(CAS reg.no.[502-65-8])、β胡萝卜素(CAS reg.no.[7235-40-7])和叶黄素,即玉米黄质(CAS reg.no.[144-68-3]);类维生素A,如肝黄质(CAS reg.no.[512-39-0])和异维A酸(CAS reg.no.[4759-48-2]);松香烷(CAS reg.no.[640-43-7]);豚草烷(ambrosane)(CASreg.no.[24749-18-6]);马兜铃烷(CAS reg.no.[29788-49-6]);阿替生烷(atisane)(CAS reg.no.[24379-83-7]);贝叶烷(beyerane)(CAS reg.no.[2359-83-3])、没药烷(CAS reg.no.[29799-19-7]);莰烷(CAS reg.no.[464-1 5-3]);丁香烷(CAS reg.no.[20479-00-9]);柏木烷(CAS reg.no.[13567-54-9]);达玛烷(CAS reg.no.[545-22-2]);锥满烷(drimane)(CASreg.no.[5951-58-6]);雅橄榄烷(eremophilane)(CAS reg.no.[3242-05-5]);桉叶烷(CAS reg.no.[473-11-0]);葑烷(CAS reg.no.[6248-88-0]);γ蜡烷(CAS reg.no.[559-65-9]);大根香叶烷(CAS reg.no.[645-10-3]);赤霉素烷(CAS reg.no.[6902-95-0]);木藜芦毒烷(grayanotoxane)(CAS reg.no.[39907-73-8]);愈创木烷(CAS reg.no.[489-80-5]);雪松烷(CAS reg.no.[20479-45-2]);藿烷(CAS reg.no.[471-62-5]);蛇麻烷(CAS reg.no.[430-19-3]);贝壳杉烷(CAS reg.no.[1573-40-6]);半日花烷(CAS reg.no.[561-90-0]);羊毛甾烷(CAS reg.no.[474-20-4]);羽扇烷(CAS reg.no.[464-99-3]);对 烷(CAS reg.no.[99-82-1]);齐墩果烷(CAS reg.no.[471-67-0]);蛇胞菌烷(ophiobolane)(CAS reg.no.[2009 8-65-1]);苦味烷(picrasane)(CAS reg.no.[35732-97-9]);海松烷(CAS reg.no.[30257-03-5]);蒎烷(CAS reg.no.[473-55-2]);罗汉松烷(CAS reg.no. [471-78-3]);原萜烷(CAS reg.no.[70050-78-1]);玫瑰烷(rosane)(CAS reg.no.[6812-82-4]);紫杉烷(taxane)(CAS reg.no.[1605-68-1]);苧烷(CAS reg.no.[471-12-5]);孢菌烷(trichothecane)(CAS reg.no.[24706-08-9]);和乌素烷(CAS reg.no.[464-93-7])及其混合物(是指这段中所列的任何萜类化合物的混合物)。本发明的萜类化合物可购得或可通过本领域已知的方法制备或可分离自天然来源。
除非上文另行指明,本发明的稳定剂可购自各种化学供应商。
单一稳定剂化合物可联合用在包含至少一种氟烯烃的本组合物中或多种稳定剂化合物可以以任何比例组合以充当稳定剂共混物。该稳定剂共混物可以含有来自相同种类化合物的多种稳定剂化合物或来自不同种类化合物的多种稳定剂化合物。例如,稳定剂混合物可以含有两种或多种硫代磷酸酯、或一种或多种硫代磷酸酯以及一种或多种内酯。
另外,一些稳定剂化合物作为多种构型异构体或立体异构体存在。相同化合物的单一异构体或多种异构体可以以任何比例使用以制备稳定剂共混物。此外,给定化合物的单一或多种异构体可以与任何数目的其它化合物以任何比例混合以充当稳定剂共混物。本发明拟包括所有单一的构型异构体、单一的立体异构体或其任何组合或混合物。
本发明进一步提供了包含至少一种选自HFC-1225ye、HFC-1234yf、HFC-1234ze和HFC-1243zf的氟烯烃和有效量的包含至少一种环氧化物、氟化环氧化物或其混合物的稳定剂的组合物。
特别重要的是包含提供出乎意料的稳定化水平的化合物组合的稳定剂组合物。某些这些组合可以充当协同稳定剂组合物,即在制剂中增强彼此效力的化合物的组合物,且所得稳定化大于由各组分的作用总和所预期的稳定化。这类协同稳定剂组合物可以包含至少一种含磷化合物和选自萜烯和萜类化合物、富勒烯、环氧化物、氟化环氧化物、氧杂环丁烷、对苯二甲酸二乙烯酯和对苯二甲酸二苯酯及其混合物(是指任何前述附加化合物与含磷化合物的混合物)的任何附加化合物。
稳定剂组合物效率的限制因素是随有效使用时间发生的稳定剂损耗和功能性损失。特别重要的是包含稳定剂混合物的协同稳定剂组合物,该稳定剂包括能在有效使用过程中使消耗的稳定剂再生的组分,下文称作再生性稳定剂。与包含多个稳定性官能团的多官能的单一大稳定剂化合物不同,包含小“协同”稳定剂的再生性稳定剂以更高迁移率和更 高稳定化速率(是指借以发生稳定化的反应的更高速率)发挥作用。再生性稳定剂组合物含有可以在使用后自我补充的一种或多种稳定剂,以便随长期使用,保持该组合物的效力。
再生性稳定剂的实例是至少一种环氧化物或氟化环氧化物和至少一种胺。再生性稳定剂组合物中包含的胺可以包含前文所述的任何受阻胺抗氧化剂。特别重要的是衍生自取代哌啶化合物的那些受阻胺,特别是烷基取代的哌啶基、哌啶子基、哌嗪酮或烷氧基哌啶子基化合物及其混合物的衍生物。代表性的受阻胺抗氧化剂是2,2,6,6-四甲基-4-哌啶酮;2,2,6,6-四甲基-4-哌啶醇;双-(1,2,2,6,6-五甲基哌啶基)癸二酸酯(CAS reg.no.[41556-26-7]);二-(2,2,6,6-四甲基-4-哌啶基)癸二酸酯,如Ciba以商标 770出售的受阻胺;聚-(N-羟乙基-2,2,6,6-四甲基-4-羟基-哌啶基丁二酸酯(CAS reg.no.[65447-77-0]),如可以以商标 622LD购自Ciba;烷基化对苯二胺,如N-苯基-N’-(1,3-二甲基丁基)-对苯二胺,或N,N’-二-仲丁基-对苯二胺;和羟胺,如牛油脂肪胺或N-甲基双(氢化牛油烷基)胺。一些其它受阻胺抗氧化剂包括包括可以以商标 765购自Ciba或以商标 1944和 1770购自Mayzo,Inc.的胺抗氧化剂。胺也包括这段中所列的任何胺的混合物。
再生性稳定剂的另一实例是包含与至少一种亚磷酸酯结合的至少一种环氧化物或氟化环氧化物的稳定剂。特别重要的是可衍生自取代亚磷酸酯的亚磷酸酯,特别是烷基、芳基亚磷酸酯化合物的衍生物。可用于再生性稳定剂的代表性的亚磷酸酯包括以商标 168出售的(三(二叔丁基苯基)亚磷酸酯)、以商标 OPH出售(亚磷酸二正辛酯)和以商标 DDPP出售的(亚磷酸异癸基二苯酯)(均来自Ciba)。
在另一实施方案中,上述任何稳定剂组合物可以进一步包含至少一种金属钝化剂,其选自草酰双(亚苄基)酰肼(CAS reg.no.6629-10-3);N,N’-双(3,5-二叔丁基-4-羟基氢化肉桂酰肼)(CAS reg.no.32687-78-8);2,2’-草酰氨基双-乙基-(3,5-二叔丁基-4-羟基氢化肉桂酸酯)(CAS reg.no.70331-94-1);N,N’-(二亚水杨基)-1,2-丙二胺(CAS reg.no.94-91-1);乙二胺四乙酸(CAS reg.no.60-00-4)及其盐;三唑;苯并三唑、2-巯基苯并噻唑、甲苯三唑衍生物、N,N-二亚水杨基-1,2-二氨基丙烷及其混合物。
在另一实施方案中,本公开提供了一种组合物,其包含a.至少一种氟烯烃;和b.有效量的稳定剂,该稳定剂包含i)至少一种环氧化物、 氟化环氧化物或其混合物;ii)至少一种亚磷酸酯、酚、萜烯、萜类化合物或其混合物;和iii)至少一种选自草酰双(亚苄基)酰肼;N,N’-双(3,5-二叔丁基-4-羟基氢化肉桂酰肼);2,2’-草酰氨基双-乙基-(3,5-二叔丁基-4-羟基氢化肉桂酸酯);N,N’-(二亚水杨基)-1,2-丙二胺;乙二胺四乙酸及其盐;三唑;苯并三唑、2-巯基苯并噻唑、甲苯三唑衍生物、N,N-二亚水杨基-1,2-二氨基丙烷及其混合物的金属钝化剂。适合包含在上述组合物中的亚磷酸酯可以是衍生自取代亚磷酸酯的受阻亚磷酸酯。特别地,受阻亚磷酸酯是烷基、芳基或烷基芳基亚磷酸酯化合物的衍生物。代表性的受阻亚磷酸酯是Irgafos 168(三(二叔丁基苯基)亚磷酸酯)、Irgafos OPH(亚磷酸二正辛酯)和Irgafos DDPP(亚磷酸异癸基二苯酯)(均来自Ciba)。适合包含在上述组合物中的酚可以是任何取代或未取代的酚化合物,包括包含一个或多个取代或未取代的环状、直链或支链脂族取代基的酚,如烷基化单酚,包括2,6-二叔丁基-4-甲基苯酚;2,6-二叔丁基-4-乙基苯酚;2,4-二甲基-6-叔丁基苯酚;生育酚;和类似物,氢醌和烷基化氢醌,包括叔丁基氢醌、氢醌的其它衍生物;和类似物,羟基化硫代二苯基醚,包括4,4’-硫代-双(2-甲基-6-叔丁基苯酚);4,4’-硫代双(3-甲基-6-叔丁基苯酚);2,2’-硫代双(4-甲基-6-叔丁基苯酚);和类似物,亚烷基-双酚,包括:4,4’-亚甲基双(2,6-二叔丁基苯酚);4,4’-双(2,6-二叔丁基苯酚);2,2’-或4,4-联苯二醇(biphenoldiols)的衍生物;2,2’-亚甲基双(4-乙基-6-叔丁基苯酚);2,2’-亚甲基双(4-甲基-6-叔丁基苯酚);4,4-亚丁基双(3-甲基-6-叔丁基苯酚);4,4-异亚丙基双(2,6-二叔丁基苯酚);2,2’-亚甲基双(4-甲基-6-壬基苯酚);2,2’-异亚丁基双(4,6-二甲基苯酚);2,2’-亚甲基双(4-甲基-6-环己基苯酚)、2,2-或4,4-联苯二醇(biphenyldiols),包括2,2’-亚甲基双(4-乙基-6-叔丁基苯酚);丁基化羟基甲苯(BHT)、包含杂原子的双酚,包括2,6-二-叔-α-二甲氨基-对甲酚、4,4-硫代双(6-叔丁基-间甲酚);和类似物;酰氨基酚;2,6-二叔丁基-4(N,N’-二甲氨基甲基苯酚);硫化物,包括双(3-甲基-4-羟基-5-叔丁基苄基)硫化物;双(3,5-二叔丁基-4-羟基苄基)硫化物;和类似物。适合包含在上述组合物中的萜烯是以含有一个或多个重复异戊二烯(2-甲基-1,3-丁二烯)单元的结构为特征的烃化合物。萜烯可以是无环或环状的。代表性的萜烯包括但不限于异戊二烯、月桂烯(2-甲基-6-亚甲基辛-1,7-二烯)、别罗勒烯、β-罗勒烯、芸香烯、苧烯(特别是d-苧烯)、视黄醛、蒎烯、薄荷醇、香叶醇、法呢醇、植醇、维生素A、 萜品烯、δ-3-蒈烯、萜品油烯、水芹烯、葑烯、二戊烯及其混合物。萜烯稳定剂可购得或可通过本领域已知的方法制备或分离自天然来源。适合包含在上述组合物中的萜类化合物是以含有多于一个重复异戊二烯单元并且通常含氧的结构为特征的天然产品和相关化合物。代表性的萜类化合物包括类胡萝卜素,如番茄红素(CAS reg.no.[502-65-8])、β胡萝卜素(CAS reg.no.[7235-40-7])和叶黄素,即玉米黄质(CAS reg.no.[144-68-3]);类维生素A,如肝黄质(CAS reg.no.[512-39-0])和异维A酸(CAS reg.no.[4759-48-2]);松香烷(CAS reg.no.[640-43-7]);豚草烷(CASreg.no.[24749-18-6]);马兜铃烷(CAS reg.no.[29788-49-6]);阿替生烷(CAS reg.no.[24379-83-7]);贝叶烷(CAS reg.no.[2359-83-3])、没药烷(CAS reg.no.[29799-19-7]);莰烷(CAS reg.no.[464-15-3]);丁香烷(CASreg.no.[20479-00-9]);柏木烷(CAS reg.no.[13567-54-9]);达玛烷(CASreg.no.[545-22-2]);锥满烷(CAS reg.no.[5951-58-6]);雅橄榄烷(CAS reg.no.[3242-05-5]);桉叶烷(CAS reg.no.[473-11-0]);葑烷(CAS reg.no.[6248-88-0]);γ蜡烷(CAS reg.no.[559-65-9]);大根香叶烷(CAS reg.no.[645-10-3]);赤霉素烷(CAS reg.no.[6902-95-0]);木藜芦毒烷(CAS reg.no.[39907-73-8]);愈创木烷(CAS reg.no.[489-80-5]);雪松烷(CAS reg.no.[20479-45-2]);藿烷(CAS reg.no.[471-62-5]);蛇麻烷(CAS reg.no.[430-19-3]);贝壳杉烷(CAS reg.no.[1573-40-6]);半日花烷(CAS reg.no.[561-90-0]);羊毛甾烷(CAS reg.no.[474-20-4]);羽扇烷(CAS reg.no.[464-99-3]);对 烷(CAS reg.no.[99-82-1]);齐墩果烷(CAS reg.no.[471-67-0]);蛇胞菌烷(CAS reg.no.[20098-65-1]);苦味烷(CAS reg.no.[35732-97-9]);海松烷(CAS reg.no.[30257-03-5]);蒎烷(CAS reg.no.[473-55-2]);罗汉松烷(CAS reg.no.[471-78-3]);原萜烷(CAS reg.no.[70050-78-1]);玫瑰烷(CAS reg.no.[6812-82-4]);紫杉烷(CAS reg.no.[1605-68-1]);苧烷(CAS reg.no.[471-12-5]);孢菌烷(CAS reg.no.[24706-08-9]);和乌素烷(CAS reg.no.[464-93-7])。本发明的萜类化合物可通过本领域已知的方法制备或可分离自天然来源。
本发明的组合物可以进一步包含至少一种选自氟烯烃(如上所述)、氟代烃、烃、二甲基醚、CF3I、二氧化碳(CO2)、氨及其混合物的附加化合物。
在一个实施方案中,附加化合物包含至少一种氟代烃(HFC)化合物。 本发明的氟代烃包含含碳、氢和氟的饱和化合物。特别有用的是具有1-7个碳原子并具有约-90℃至约80℃的标准沸点的氟代烃。氟代烃是可获自许多来源如E.I.du Pont de Nemours & Co.,F1uoroproducts,Wilmington,DE,19898,USA的商品,或可以通过本领域已知的方法制备。代表性的氟代烃化合物包括但不限于氟代甲烷(CH3F,HFC-41)、二氟甲烷(CH2F2,HFC-32)、三氟甲烷(CHF3,HFC-23)、五氟乙烷(CF3CHF2,HFC-125)、1,1,2,2-四氟乙烷(CHF2CHF2,HFC-134)、1,1,1,2-四氟乙烷(CF3CH2F,HFC-134a)、1,1,1-三氟乙烷(CF3CH3,HFC-143a)、1,1-二氟乙烷(CHF2CH3,HFC-152a)、氟代乙烷(CH3CH2F,HFC-161)、1,1,1,2,2,3,3-七氟丙烷(CF3CF2CHF2,HFC-227ca)、1,1,1,2,3,3,3-七氟丙烷(CF3CHFCF3,HFC-227ea)、1,1,2,2,3,3-六氟丙烷(CHF2CF2CHF2,HFC-236ca)、1,1,1,2,2,3-六氟丙烷(CF3CF3CH2F,HFC-236cb)、1,1,1,2,3,3-六氟丙烷(CF3CHFCHF2,HFC-236ea)、1,1,1,3,3,3-六氟丙烷(CF3CH2CF3,HFC-236fa)、1,1,2,2,3-五氟丙烷(CHF2CF2CH2F,HFC-245ca)、1,1,1,2,2-五氟丙烷(CF3CF2CH3,HFC-245cb)、1,1,2,3,3-五氟丙烷(CHF2CHFCHF2,HFC-245ea)、1,1,1,2,3-五氟丙烷(CF3CHFCH2F,HFC-245eb)、1,1,1,3,3-五氟丙烷(CF3CH2CHF2,HFC-245fa)、1,2,2,3-四氟丙烷(CH2FCF2CH2F,HFC-254ca)、1,1,2,2-四氟丙烷(CHF2CF2CH3,HFC-254cb)、1,1,2,3-四氟丙烷(CHF2CHFCH2F,HFC-254ea)、1,1,1,2-四氟丙烷(CF3CHFCH3,HFC-254eb)、1,1,3,3-四氟丙烷(CHF2CH2CHF2,HFC-254fa)、1,1,1,3-四氟丙烷(CF3CH2CH2F,HFC-254fb)、1,1,1-三氟丙烷(CF3CH2CH3,HFC-263fb)、2,2-二氟丙烷(CH3CF2CH3,HFC-272ca)、1,2-二氟丙烷(CH2FCHFCH3,HFC-272ea)、1,3-二氟丙烷(CH2FCH2CH2F,HFC-272fa)、1,1-二氟丙烷(CHF2CH2CH3,HFC-272fb)、2-氟丙烷(CH3CHFCH3,HFC-281ea)、1-氟丙烷(CH2FCH2CH3,HFC-281fa)、1,1,2,2,3,3,4,4-八氟丁烷(CHF2CF2CF2CHF2,HFC-338pcc)、1,1,1,2,2,4,4,4-八氟丁烷(CF3CH2CF2CF3,HFC-338mf)、1,1,1,3,3-五氟丁烷(CF3CH2CHF2,HFC-365mfc)、1,1,1,2,3,4,4,5,5,5-十氟戊烷(CF3CHFCHFCF2CF3,HFC-43-10mee)和1,1,1,2,2,3,4,5,5,6,6,7,7,7-十四氟庚烷(CF3CF2CHFCHFCF2CF2CF3,HFC-63-14mee)。
在另一实施方案中,附加化合物包含至少一种烃。本发明的烃包含只有碳和氢的化合物。特别有用的是具有3-7个碳原子的化合物。烃可 通过许多化学供应商购得。代表性的烃包括但不限于丙烷、正丁烷、异丁烷、环丁烷、正戊烷、2-甲基丁烷、2,2-二甲基丙烷、环戊烷、正己烷、2-甲基戊烷、2,2-二甲基丁烷、2,3-二甲基丁烷、3-甲基戊烷、环己烷、正庚烷和环庚烷。
在另一实施方案中,附加化合物还可以包含含杂原子的烃,如二甲基醚(DME,CH3OCH3)。DME可购得。
在另一实施方案中,附加化合物还可以包含碘代三氟甲烷(CF3I),其可购自各种来源或可以通过本领域已知的方法制备。
在另一实施方案中,附加化合物还可以包含二氧化碳(CO2),其可购自各种来源或可以通过本领域已知的方法制备。
在另一实施方案中,附加化合物还可以包含氨(NH3),其可购自各种来源或可以通过本领域已知的方法制备,
在另一实施方案中,特别重要的是的附加化合物包括下列组合物,其包含:HFC-1225ye和HFC-32;HFC-1225ye和HFC-134a;HFC-1225ye、HFC-134a和HFC-32;HFC-1225ye和HFC-1234yf;HFC-1225ye、HFC-1234yf和HFC-32;和HFC-1225ye、HFC-1234yf和HFC-125。
在另一实施方案中,附加化合物包括包含如2006年3月2日提交的美国专利申请no.11/369,227、2006年3月30日提交的美国专利申请no.11/393,109和2006年7月13日提交的美国专利申请no.11/486,791中公开的氟烯烃的组合物,它们拟包括在本发明的范围内。
本发明的组合物可以进一步包含至少一种润滑剂。本发明的润滑剂包含适合与制冷或空调装置一起使用的那些。这些润滑剂包括传统上用在采用氯氟烃制冷剂的压缩制冷装置中的那些。在1990 ASHRAEHandbook,Refrigeration Systems and Applications,第8章,标题″Lubricants in Refrigeration Systems″,第8.1至8.21页(在此引入作为参考)中论述了这类润滑剂和它们的性质。本发明的润滑剂可以包含在压缩制冷润滑领域中常被称作“矿物油”的那些。矿物油包含链烷烃(即直链和支链碳链饱和烃)、环烷烃(即环状或环结构饱和烃,其可能是链烷烃)和芳烃(即含有一个或多个以交替双键为特征的环的不饱和环烃)。本发明的润滑剂进一步包含在压缩制冷润滑领域中常被称作“合成油”的那些。合成油包含烷基芳基(即直链和支链烷基烷基苯)、合成链烷烃和环烷烃、硅氧烷和聚-α-烯烃。本发明的代表性的传统润滑剂是市售BVM 100 N(BVA Oils出售的链烷矿物油)、可以以商标 3GS和 5GS购自Crompton Co.的环烷矿物油、可以以商标 372LT购自Pennzoil的环烷矿物油、可以以商标 RO-30购自CalumetLubricants的环烷矿物油、可以以商标 75、 150和 500购自Shrieve Chemicals的直链烷基苯和Nippon Oil作为HAB 22出售的支链烷基苯。
本发明的润滑剂进一步包含已经设计成与氟代烃制冷剂一起使用并且在压缩制冷和空调装置操作条件下与本发明的制冷剂混溶的那些。在″Synthetic Lubricants and High-Performance Fluids″,R.L.Shubkin,编辑,Marcel Dekker,1993中论述了这类润滑剂及其性质。这类润滑剂包括但不限于多元醇酯(POEs),例如 100(Castrol,United Kingdom),聚亚烷基二醇(PAGs),例如来自Dow(Dow Chemical,Midland,Michigan)的RL-488A,和聚乙烯醚(PVEs)。
通过考虑给定压缩机的要求和润滑剂所要暴露的环境来选择本发明的润滑剂。
本发明的组合物可以通过混合所需量的各组分的任何方便方法制备。优选方法是称出所需组分量并随后在适当的容器中混合组分。如果需要,可以使用搅拌。
在包含至少一种氟烯烃的组合物中可以使用任何合适的有效量的稳定剂。本文所述的术语“有效量”是指本发明的稳定剂的量,其在添加到包含至少一种氟烯烃的组合物中时产生的组合物不会降解造成与无稳定剂的组合物相比一样大的在冷却装置中使用时的制冷性能降低。稳定剂的这种有效量可以通过在标准试验条件ASHRAE 97-2004下测试来测定。在本发明的某些实施方案中,有效量可以被说成是在与包含至少一种氟烯烃的组合物混合时允许采用所述包含至少一种氟烯烃的组合物的冷却装置在与采用包含1,1,1,2-四氟乙烷(R-134a)或其它标准制冷剂(R12、R22、R502、R507A、R508、R401A、R401B、R402A、R402B、R408、R410A、R404A、R407C、R413A、R417A、R422A、R422B、R422C、R422D、R423、R114、R11、R113、R123、R124、R236fa或R245fa)(取决于过去在类似系统中使用哪种制冷剂)的组合物作为工作流体时相同水平的制冷性能和冷却容量下运行的稳定剂的量。
某些实施方案包括有效量的在本发明中所用的稳定剂,其构成本文 所述的包含至少一种氟烯烃的组合物总重量的约0.001wt%至约10wt%,更优选约0.01wt%至约5wt%,再更优选约0.3wt%至约4wt%,再更优选约0.3wt%至约1wt%。
本发明进一步涉及使包含至少一种氟烯烃的组合物稳定化的方法,所述方法包括添加有效量的稳定剂,其包含:a.至少一种环氧化物或氟化环氧化物;和b.至少一种选自硫代磷酸酯、丁基化三苯基硫代磷酸酯、有机磷酸酯、富勒烯、官能化全氟聚醚、聚氧烷基化芳族化合物、烷基化芳族化合物、氧杂环丁烷、抗坏血酸、硫醇、内酯、硫醚、胺、硝基甲烷、烷基硅烷、二苯甲酮衍生物、芳基硫醚、对苯二甲酸二乙烯酯、对苯二甲酸二苯酯及其混合物的化合物。
本发明进一步涉及制冷方法,包括冷凝包含至少一种氟烯烃和有效量稳定剂的组合物,该稳定剂包含:a.至少一种环氧化物或氟化环氧化物;和b.至少一种选自硫代磷酸酯、丁基化三苯基硫代磷酸酯、有机磷酸酯、富勒烯、官能化全氟聚醚、聚氧烷基化芳族化合物、烷基化芳族化合物、氧杂环丁烷、抗坏血酸、硫醇、内酯、硫醚、胺、硝基甲烷、烷基硅烷、二苯甲酮衍生物、芳基硫醚、对苯二甲酸二乙烯酯、对苯二甲酸二苯酯及其混合物的化合物,此后在要冷却的物体附近蒸发所述组合物。
要冷却的物体可以是要求制冷或空调的任何空间、位置或物品。在静止用途中,该物体可以是结构,即住宅或商业结构内部,或易腐货物,如食品或药品的储存位置。对于移动制冷用途,该物体可以在公路、铁路、海洋或航空运输工具内。某些制冷系统独立于任何移动载体运行,这些被称作“联合运输”系统。这类联合运输系统包括“集装箱(containers)”(联合海洋/陆路运输)以及“交换体(swap bodies)”(联合公路和铁路运输)。
本发明进一步涉及制热方法,包括在要加热的物体附近冷凝包含至少一种氟烯烃和有效量稳定剂的组合物,该稳定剂包含:a.至少一种环氧化物或氟化环氧化物;和b.至少一种选自硫代磷酸酯、丁基化三苯基硫代磷酸酯、有机磷酸酯、富勒烯、官能化全氟聚醚、聚氧烷基化芳族化合物、烷基化芳族化合物、氧杂环丁烷、抗坏血酸、硫醇、内酯、硫醚、胺、硝基甲烷、烷基硅烷、二苯甲酮衍生物、芳基硫醚、对苯二甲酸二乙烯酯、对苯二甲酸二苯酯及其混合物的化合物,和此后蒸发所述组合物。
要加热的物体可以是需要热的任何空间、位置或物品。与要冷却的物体类似,这些可以是住宅或商业结构的内部。另外,对冷却所述的移动装置可以与需要加热的那些类似。某些运输工具要求加热以防止运输的材料在运输容器内凝固。
空气不常泄漏到制冷、空调系统或热泵中。空气中的氧可能造成该系统的某些组分(包括工作流体)的氧化。因此,在另一实施方案中,还公开了降低包含至少一种氟烯烃的组合物的降解的方法,其中所述降解由误入空气的存在引起;例如在制冷、空调或热泵系统中,所述方法包括将有效量的稳定剂添加到包含至少一种氟烯烃的组合物中,所述稳定剂包含至少一种环氧化物或氟化环氧化物和至少一种选自硫代磷酸酯、丁基化三苯基硫代磷酸酯、有机磷酸酯、富勒烯、官能化全氟聚醚、聚氧烷基化芳族化合物、烷基化芳族化合物、氧杂环丁烷、抗坏血酸、硫醇、内酯、硫醚、胺、硝基甲烷、烷基硅烷、二苯甲酮衍生物、芳基硫醚、对苯二甲酸二乙烯酯、对苯二甲酸二苯酯及其混合物的化合物。
在另一实施方案中,还公开了减少包含至少一种氟烯烃的组合物与氧反应的方法,所述方法包括将有效量的稳定剂添加到包含至少一种氟烯烃的组合物中,所述稳定剂包含至少一种环氧化物或氟化环氧化物和至少一种选自硫代磷酸酯、丁基化三苯基硫代磷酸酯、有机磷酸酯、富勒烯、官能化全氟聚醚、聚氧烷基化芳族化合物、烷基化芳族化合物、氧杂环丁烷、抗坏血酸、硫醇、内酯、硫醚、胺、硝基甲烷、烷基硅烷、二苯甲酮衍生物、芳基硫醚、对苯二甲酸二乙烯酯、对苯二甲酸二苯酯及其混合物的化合物。
实施例
制冷系统化学稳定性
在ASHRAE(American Society of Heating,Refrigerating and Air-Conditioning Engineers)标准97-2004中所述的条件下进行化学稳定性试验以测定与不含稳定剂的组合物相比本发明的稳定化组合物的化学稳定性。
在此给出程序:
1.将铜、铝和钢的金属试块置于厚壁玻璃管中。
2.制备含和不含稳定剂的包括润滑剂的工作流体样品,并任选在该管中加入2体积%空气。
3.如所述标准中所述将样品添加到所述玻璃管中。
4.用玻璃喷灯密封所述管。
5.将密封的管在烘箱中在指定温度下加热14天。
6.在14天后,将密封的管从炉中取出并检查金属/液体外观、液体适当体积、玻璃外观、和外来材料如金属细粒的不存在。
7.基于下列标准指认各样品的等级(根据工业实践):
1=试块和液体上的轻微变化;
2=试块或液体上的轻微至中等变化;
3=试块或液体上的中等至显著变化;
4=试块或液体上的严重变化;
5=试块或液体上的极端变化,即黑色液体或焦化并含许多沉积物。
表4列出本发明的稳定剂与未稳定化的组合物相比的评估结果。 PAG 488是可购自The Dow Chemical Company的聚亚烷基二醇润滑剂的商标。 63是可购自Ciba的二硫代磷酸酯的商标。 232是可购自Ciba的丁基化三苯基硫代磷酸酯的商标。 349是可购自Ciba的胺磷酸酯混合物的商标(有机磷酸酯的一个实例)。 350和 353是可购自Ciba的二烷基二硫代磷酸酯的商标。 157FSL是可购自DuPont的官能化全氟聚醚的商标。 150是Shrieve Chemical出售的烷基苯润滑剂的商标。OXT-101是来自Toagosei Company的3-乙基-3-羟甲基氧杂环丁烷。 622LD是可购自Ciba的受阻胺抗氧化剂的商标。HP-136是来自Ciba的5,7-二叔丁基-3-(3-4-二甲基苯基)-3H-苯并呋喃-2-酮(内酯的一个实例)。润滑剂 PAG 488与下表4中列出的工作流体混合以制造50wt%工作流体和50wt%润滑剂的组合物。
表4
评估结果表明在有和没有空气存在的情况下在稳定剂存在下改进的化学稳定性。
Claims (14)
1.包含至少一种氟烯烃和有效量的稳定剂的组合物,该稳定剂包含:
a.至少一种选自选自1,2-环氧丙烷和1,2-环氧丁烷的环氧化物或式A所示的氟化环氧化物的化合物,其中R2至R5各自是H、具有1至6个碳原子的烷基或具有1至6个碳原子的氟烷基,条件是R2至R5中的至少一个是氟烷基;
和
b.二苯甲酮衍生物;
其中所述有效量基于所述组合物的总重量为0.001wt%至10wt%。
2.权利要求1的组合物,其中:
二苯甲酮衍生物选自2,5-二氟二苯甲酮;2’,5’-二羟基苯乙酮;2-氨基二苯甲酮;2-氯二苯甲酮;2-氟二苯甲酮;2-羟基二苯甲酮;2-甲基二苯甲酮;2-氨基-4′-氯二苯甲酮;2-氨基-4′-氟二苯甲酮;2-氨基-5-溴-2′-氯二苯甲酮;2-氨基-5-氯二苯甲酮;2-氨基-5-氯-2′-氟二苯甲酮;2-氨基-5-硝基二苯甲酮;2-氨基-5-硝基-2′-氯二苯甲酮;2-氨基-2′,5-二氯二苯甲酮;2-氯-4′-氟二苯甲酮;2-羟基-4-甲氧基二苯甲酮;2-羟基-5-氯二苯甲酮;2-甲氨基-5-氯二苯甲酮;3-甲基二苯甲酮;3-硝基二苯甲酮;3-硝基-4′-氯-4-氟二苯甲酮;4-氯二苯甲酮;4-氟二苯甲酮;4-羟基二苯甲酮;4-甲氧基二苯甲酮;4-甲基二苯甲酮;4-硝基二苯甲酮;4-苯基二苯甲酮;4-氯-3-硝基二苯甲酮;4-羟基-4′-氯二苯甲酮;2,4-二羟基二苯甲酮;2,4-二甲基二苯甲酮;2,5-二甲基二苯甲酮;3,4-二氨基二苯甲酮;3,4-二氯二苯甲酮;3,4-二氟二苯甲酮;3,4-二羟基二苯甲酮;3,4-二甲基二苯甲酮;4,4′-双(二乙胺)二苯甲酮;4,4′-双(二甲基胺)二苯甲酮;4,4′-二氯二苯甲酮;4,4′-二氟二苯甲酮;4,4′-二羟基二苯甲酮;4,4′-二甲氧基二苯甲酮及其混合物。
3.权利要求1的组合物,其进一步包含至少一种选自氟代烃的制冷剂。
4.权利要求1的组合物,进一步包含选自矿物油、烷基苯、聚α烯烃、硅油、聚氧化烯二醇醚、多元醇酯、聚乙烯醚及其混合物的润滑剂。
5.权利要求1的组合物,其进一步包含至少一种选自酚、亚磷酸酯、萜烯、萜类化合物及其混合物的附加稳定剂化合物。
6.权利要求5的组合物,其中:
a.酚选自2,6-二叔丁基-4-甲基苯酚;2,6-二叔丁基-4-乙基苯酚;2,4-二甲基-6-叔丁基苯酚;生育酚;氢醌;叔丁基氢醌;4,4’-硫代-双(2-甲基-6-叔丁基苯酚);4,4’-硫代双(3-甲基-6-叔丁基苯酚);2,2’-硫代双(4-甲基-6-叔丁基苯酚);4,4’-亚甲基双(2,6-二叔丁基苯酚);4,4’-双(2,6-二叔丁基苯酚);2,2’-亚甲基双(4-乙基-6-叔丁基苯酚);2,2’-亚甲基双(4-甲基-6-叔丁基苯酚);4,4-亚丁基双(3-甲基-6-叔丁基苯酚);4,4-异亚丙基双(2,6-二叔丁基苯酚);2,2’-亚甲基双(4-甲基-6-壬基苯酚);2,2’-异亚丁基双(4,6-二甲基苯酚);2,2’-亚甲基双(4-甲基-6-环己基苯酚)、2,2’-亚甲基双(4-乙基-6-叔丁基苯酚);丁基化羟基甲苯(BHT);2,6-二-叔-α-二甲氨基-对甲酚;4,4-硫代双(6-叔丁基-间甲酚);酰氨基酚;2,6-二叔丁基-4(N,N’-二甲氨基甲基苯酚);双(3-甲基-4-羟基-5-叔丁基苄基)硫化物;双(3,5-二叔丁基-4-羟基苄基)硫化物及其混合物;
b.亚磷酸酯选自三(二叔丁基苯基)亚磷酸酯、亚磷酸二正辛酯、亚磷酸异癸基二苯酯及其混合物;
c.萜烯选自异戊二烯、月桂烯、别罗勒烯、β-罗勒烯、芸香烯、d-苧烯、视黄醛、蒎烯、薄荷醇、香叶醇、法呢醇、植醇、维生素A、萜品烯、δ-3-蒈烯、萜品油烯、水芹烯、葑烯、二戊烯、番茄红素、β胡萝卜素、玉米黄质、肝黄质、异维A酸及其混合物;
d.萜类化合物选自松香烷、豚草烷、马兜铃烷、阿替生烷、贝叶烷、没药烷、莰烷、丁香烷、柏木烷、达玛烷、锥满烷、雅橄榄烷、桉叶烷、葑烷、γ蜡烷、大根香叶烷、赤霉素烷、木藜芦毒烷、愈创木烷、雪松烷、藿烷、蛇麻烷、贝壳杉烷、半日花烷、羊毛甾烷、羽扇烷、对烷、齐墩果烷、蛇胞茵烷、苦味烷、海松烷、蒎烷、罗汉松烷、原萜烷、玫瑰烷、紫杉烷、苧烷、孢菌烷、乌素烷;及其混合物;
e.硫代磷酸酯选自单硫代磷酸酯、二硫代磷酸酯、三硫代磷酸酯、二烷基硫代磷酸酯及其混合物;
f.丁基化三苯基硫代磷酸酯由式B表示,
其中各R独立地选自H或叔丁基;
g.有机磷酸酯选自胺磷酸酯、磷酸三烷基酯、磷酸三芳基酯、混合烷基-芳基磷酸酯、环状磷酸酯及其混合物;
h.富勒烯选自Buckminsterfullerene、[5,6]富勒烯-C70、富勒烯-C76、富勒烯-C78、富勒烯-C84及其混合物;
i.芳基烷基醚由式C表示,其中n是1、2或3且R1是具有1至16个碳原子的烷基,
j.聚氧烷基化芳族化合物是式C所示的化合物,其中R1基团是包含至少一个-CH2CH2O-部分的聚氧烷基化基团;
k.烷基化芳族化合物是直链或支链烷基苯润滑剂;
l.氧杂环丁烷由式D表示
其中R1-R6独立地选自氢、烷基或取代烷基、芳基或取代芳基;
m.硫醇选自甲硫醇、乙硫醇、辅酶A、二巯基丁二酸、(R)-2-(4-甲基环己-3-烯基)丙-2-硫醇、半胱氨酸、硫辛酰胺及其混合物;
n.内酯选自γ-丁内酯、δ-葡糖酸内酯、γ-十一内酯、6,7-二氢-4(5H)-苯并呋喃酮、5,7-双(1,1-二甲基乙基)-3-[2,3(或3,4)-二甲基苯基]-2(3H)-苯并呋喃酮及其混合物;
o.硫醚选自苄基苯基硫醚、二苯硫醚、二(十八烷基)3,3’-硫代二丙酸酯、二(十二烷基)3,3’-硫代丙酸酯及其混合物;
p.胺选自三乙胺;三丁胺;二异丙胺;三异丙胺;三异丁胺;对苯二胺;二苯基胺;二烷基胺;N-(1-甲基乙基)-2-丙胺;烷基取代的哌啶基、哌啶子基、哌嗪酮和烷氧基哌啶子基化合物;2,2,6,6-四甲基-4-哌啶酮;2,2,6,6-四甲基-4-哌啶醇;双-(1,2,2,6,6-五甲基哌啶基)癸二酸酯;二-(2,2,6,6-四甲基-4-哌啶基)癸二酸酯;聚-(N-羟乙基-2,2,6,6-四甲基-4-羟基-哌啶基丁二酸酯;2,2,6,6-四甲基-4-哌啶酮,2,2,6,6-四甲基-4-哌啶醇、双-(1,2,2,6,6-五甲基哌啶基)癸二酸酯、二-(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、聚-(N-羟乙基-2,2,6,6-四甲基-4-羟基-哌啶基丁二酸酯及其混合物;
q.烷基硅烷选自双(二甲氨基)甲基硅烷、三(三甲基甲硅烷基)硅烷、乙烯基三乙氧基硅烷、乙烯基三甲氧基硅烷及其混合物;且
r.芳基硫醚选自苄基苯基硫醚、二苯硫醚和二苄基硫醚。
7.权利要求1的组合物,其中所述环氧化物或氟化环氧化物选自1,2-环氧丙烷、1,2-环氧丁烷、三氟甲基环氧乙烷、1,1-双(三氟甲基)环氧乙烷及其混合物。
8.权利要求1的组合物,其中所述氟烯烃是至少一种选自下列的化合物:
(i)式E-或Z-R1CH=CHR2的氟烯烃,其中R1和R2独立地为C1至C6全氟烷基;
(ii)式环-[CX=CY(CZW)n -]的环氟烯烃,其中X、Y、Z和W独立地为H或F,且n是2至5的整数;和
(iii)选自下列的氟烯烃:
1,2,3,3,3-五氟-1-丙烯(CHF=CFCF3)、1,1,3,3,3-五氟-1-丙烯(CF2=CHCF3)、1,1,2,3,3-五氟-1-丙烯(CF2=CFCHF2)、1,2,3,3-四氟-1-丙烯(CHF=CFCHF2)、2,3,3,3-四氟-1-丙烯(CH2=CFCF3)、1,3,3,3-四氟-1-丙烯CHF=CHCF3)、1,1,2,3-四氟-1-丙烯(CF2=CFCH2F)、1,1,3,3-四氟-1-丙烯(CF2=CHCHF2)、1,2,3,3-四氟-1-丙烯(CHF=CFCHF2)、3,3,3-三氟-1-丙烯(CH2=CHCF3)、2,3,3-三氟-1-丙烯(CHF2CF=CH2);1,1,2-三氟-1-丙烯(CH3CF=CF2);1,2,3-三氟-1-丙烯(CH2FCF=CF2);1,1,3-三氟-1-丙烯(CH2FCH=CF2);1,3,3-三氟-1-丙烯(CHF2CH=CHF);1,1,1,2,3,4,4,4-八氟-2-丁烯(CF3CF=CFCF3);1,1,2,3,3,4,4,4-八氟-1-丁烯(CF3CF2CF=CF2);1,1,1,2,4,4,4-七氟-2-丁烯(CF3CF=CHCF3);1,2,3,3,4,4,4-七氟-1-丁烯(CHF=CFCF2CF3);1,1,1,2,3,4,4-七氟-2-丁烯(CHF2CF=CFCF3);1,3,3,3-四氟-2-(三氟甲基)-1-丙烯((CF3)2C=CHF);1,1,3,3,4,4,4-七氟-1-丁烯(CF2=CHCF2CF3);1,1,2,3,4,4,4-七氟-1-丁烯(CF2=CFCHFCF3);1,1,2,3,3,4,4-七氟-1-丁烯(CF2=CFCF2CHF2);2,3,3,4,4,4-六氟-1-丁烯(CF3CF2CF=CH2);1,3,3,4,4,4-六氟-1-丁烯(CHF=CHCF2CF3);1,2,3,4,4,4-六氟-1-丁烯(CHF=CFCHFCF3);1,2,3,3,4,4-六氟-1-丁烯(CHF=CFCF2CHF2);1,1,2,3,4,4-六氟-2-丁烯(CHF2CF=CFCHF2);1,1,1,2,3,4-六氟-2-丁烯(CH2FCF=CFCF3);1,1,1,2,4,4-六氟-2-丁烯(CHF2CH=CFCF3);1,1,1,3,4,4-六氟-2-丁烯(CF3CH=CFCHF2);1,1,2,3,3,4-六氟-1-丁烯(CF2=CFCF2CH2F);1,1,2,3,4,4-六氟-1-丁烯(CF2=CFCHFCHF2);3,3,3-三氟-2-(三氟甲基)-1-丙烯(CH2=C(CF3)2);1,1,1,2,4-五氟-2-丁烯(CH2FCH=CFCF3);1,1,1,3,4-五氟-2-丁烯(CF3CH=CFCH2F);3,3,4,4,4-五氟-1-丁烯(CF3CF2CH=CH2);1,1,1,4,4-五氟-2-丁烯(CHF2CH=CHCF3);1,1,1,2,3-五氟-2-丁烯(CH3CF=CFCF3);2,3,3,4,4-五氟-1-丁烯(CH2=CFCF2CHF2);1,1,2,4,4-五氟-2-丁烯(CHF2CF=CHCHF2);1,1,2,3,3-五氟-1-丁烯(CH3CF2CF=CF2);1,1,2,3,4-五氟-2-丁烯(CH2FCF=CFCHF2);1,1,3,3,3-五氟-2-甲基-1-丙烯(CF2=C(CF3)(CH3));2-(二氟甲基)-3,3,3-三氟-1-丙烯(CH2=C(CHF2)(CF3));2,3,4,4,4-五氟-1-丁烯(CH2=CFCHFCF3);1,2,4,4,4-五氟-1-丁烯(CHF=CFCH2CF3);1,3,4,4,4-五氟-1-丁烯(CHF=CHCHFCF3);1,3,3,4,4-五氟-1-丁烯(CHF=CHCF2CHF2);1,2,3,4,4-五氟-1-丁烯(CHF=CFCHFCHF2);3,3,4,4-四氟-1-丁烯(CH2=CHCF2CHF2);1,1-二氟-2-(二氟甲基)-1-丙烯(CF2=C(CHF2)(CH3));1,3,3,3-四氟-2-甲基-1-丙烯(CHF=C(CF3)(CH3));3,3-二氟-2-(二氟甲基)-1-丙烯(CH2=C(CHF2)2);1,1,1,2-四氟-2-丁烯(CF3CF=CHCH3);1,1,1,3-四氟-2-丁烯(CH3CF=CHCF3);1,1,1,2,3,4,4,5,5,5-十氟-2-戊烯(CF3CF=CFCF2CF3);1,1,2,3,3,4,4,5,5,5-十氟-1-戊烯(CF2=CFCF2CF2CF3);1,1,1,4,4,4-六氟-2-(三氟甲基)-2-丁烯((CF3)2C=CHCF3);1,1,1,2,4,4,5,5,5-九氟-2-戊烯(CF3CF=CHCF2CF3);1,1,1,3,4,4,5,5,5-九氟-2-戊烯(CF3CH=CFCF2CF3);1,2,3,3,4,4,5,5,5-九氟-1-戊烯(CHF=CFCF2CF2CF3);1,1,3,3,4,4,5,5,5-九氟-1-戊烯(CF2=CHCF2CF2CF3);1,1,2,3,3,4,4,5,5-九氟-1-戊烯(CF2=CFCF2CF2CHF2);1,1,2,3,4,4,5,5,5-九氟-2-戊烯(CHF2CF=CFCF2CF3);1,1,1,2,3,4,4,5,5-九氟-2-戊烯(CF3CF=CFCF2CHF2);1,1,1,2,3,4,5,5,5-九氟-2-戊烯(CF3CF=CFCHFCF3);1,2,3,4,4,4-六氟-3-(三氟甲基)-1-丁烯(CHF=CFCF(CF3)2);1,1,2,4,4,4-六氟-3-(三氟甲基)-1-丁烯(CF2=CFCH(CF3)2);1,1,1,4,4,4-六氟-2-(三氟甲基)-2-丁烯(CF3CH=C(CF3)2);1,1,3,4,4,4-六氟-3-(三氟甲基)-1-丁烯(CF2=CHCF(CF3)2);2,3,3,4,4,5,5,5-八氟-1-戊烯(CH2=CFCF2CF2CF3);1,2,3,3,4,4,5,5-八氟-1-戊烯(CHF=CFCF2CF2CHF2);3,3,4,4,4-五氟-2-(三氟甲基)-1-丁烯(CH2=C(CF3)CF2CF3);1,1,4,4,4-五氟-3-(三氟甲基)-1-丁烯(CF2=CHCH(CF3)2);1,3,4,4,4-五氟-3-(三氟甲基)-1-丁烯(CHF=CHCF(CF3)2);1,1,4,4,4-五氟-2-(三氟甲基)-1-丁烯(CF2=C(CF3)CH2CF3);3,4,4,4-四氟-3-(三氟甲基)-1-丁烯((CF3)2CFCH=CH2);3,3,4,4,5,5,5-七氟-1-戊烯(CF3CF2CF2CH=CH2);2,3,3,4,4,5,5-七氟-1-戊烯(CH2=CFCF2CF2CHF2);1,1,3,3,5,5,5-七氟-1-丁烯(CF2=CHCF2CH2CF3);1,1,1,2,4,4,4-七氟-3-甲基-2-丁烯(CF3CF=C(CF3)(CH3));2,4,4,4-四氟-3-(三氟甲基)-1-丁烯(CH2=CFCH(CF3)2);1,4,4,4-四氟-3-(三氟甲基)-1-丁烯(CHF=CHCH(CF3)2);1,1,1,4-四氟-2-(三氟甲基)-2-丁烯(CH2FCH=C(CF3)2);1,1,1,3-四氟-2-(三氟甲基)-2-丁烯(CH3CF=C(CF3)2);1,1,1-三氟-2-(三氟甲基)-2-丁烯((CF3)2C=CHCH3);3,4,4,5,5,5-六氟-2-戊烯(CF3CF2CF=CHCH3);1,1,1,4,4,4-六氟-2-甲基-2-丁烯(CF3C(CH3)=CHCF3);3,3,4,5,5,5-六氟-1-戊烯(CH2=CHCF2CHFCF3);4,4,4-三氟-2-(三氟甲基)-1-丁烯(CH2=C(CF3)CH2CF3);1,1,2,3,3,4,4,5,5,6,6,6-十二氟-1-己烯(CF3(CF2)3CF=CF2);1,1,1,2,2,3,4,5,5,6,6,6-十二氟-3-己烯(CF3CF2CF=CFCF2CF3);1,1,1,4,4,4-六氟-2,3-双(三氟甲基)-2-丁烯((CF3)2C=C(CF3)2);1,1,1,2,3,4,5,5,5-九氟-4-(三氟甲基)-2-戊烯((CF3)2CFCF=CFCF3);1,1,1,4,4,5,5,5-八氟-2-(三氟甲基)-2-戊烯((CF3)2C=CHC2F5);1,1,1,3,4,5,5,5-八氟-4-(三氟甲基)-2-戊烯((CF3)2CFCF=CHCF3);3,3,4,4,5,5,6,6,6-九氟-1-己烯(CF3CF2CF2CF2CH=CH2);4,4,4-三氟-3,3-双(三氟甲基)-1-丁烯(CH2=CHC(CF3)3);1,1,1,4,4,4-六氟-3-甲基-2-(三氟甲基)-2-丁烯((CF3)2C=C(CH3)(CF3));2,3,3,5,5,5-六氟-4-(三氟甲基)-1-戊烯(CH2=CFCF2CH(CF3)2);1,1,1,2,4,4,5,5,5-九氟-3-甲基-2-戊烯(CF3CF=C(CH3)CF2CF3);1,1,1,5,5,5-六氟-4-(三氟甲基)-2-戊烯(CF3CH=CHCH(CF3)2);3,4,4,5,5,6,6,6-八氟-2-己烯(CF3CF2CF2CF=CHCH3);3,3,4,4,5,5,6,6-八氟1-己烯(CH2=CHCF2CF2CF2CHF2);1,1,1,4,4-五氟-2-(三氟甲基)-2-戊烯((CF3)2C=CHCF2CH3);4,4,5,5,5-五氟-2-(三氟甲基)-1-戊烯(CH2=C(CF3)CH2C2F5);3,3,4,4,5,5,5-七氟-2-甲基-1-戊烯(CF3CF2CF2C(CH3)=CH2);4,4,5,5,6,6,6-七氟-2-己烯(CF3CF2CF2CH=CHCH3);4,4,5,5,6,6,6-七氟-1-己烯(CH2=CHCH2CF2C2F5);1,1,1,2,2,3,4-七氟-3-己烯(CF3CF2CF=CFC2H5);4,5,5,5-四氟-4-(三氟甲基)-1-戊烯(CH2=CHCH2CF(CF3)2);1,1,1,2,5,5,5-七氟-4-甲基-2-戊烯(CF3CF=CHCH(CF3)(CH3));1,1,1,3-四氟-2-(三氟甲基)-2-戊烯((CF3)2C=CFC2H5);1,1,1,2,3,4,4,5,5,6,6,7,7,7-十四氟-2-庚烯(CF3CF=CFCF2CF2C2F5);1,1,1,2,2,3,4,5,5,6,6,7,7,7-十四氟-3-庚烯(CF3CF2CF=CFCF2C2F5);1,1,1,3,4,4,5,5,6,6,7,7,7-十三氟-2-庚烯(CF3CH=CFCF2CF2C2F5);1,1,1,2,4,4,5,5,6,6,7,7,7-十三氟-2-庚烯(CF3CF=CHCF2CF2C2F5);1,1,1,2,2,4,5,5,6,6,7,7,7-十三氟-3-庚烯(CF3CF2CH=CFCF2C2F5);和1,1,1,2,2,3,5,5,6,6,7,7,7-十三氟-3-庚烯(CF3CF2CF=CHCF2C2F5)。
9.权利要求1的组合物,进一步包含至少一种选自草酰双(亚苄基)酰肼;N,N’-双(3,5-二叔丁基-4-羟基氢化肉桂酰肼);2,2’-草酰氨基双-乙基-(3,5-二叔丁基-4-羟基氢化肉桂酸酯);N,N’-(二亚水杨基)-1,2-丙二胺;乙二胺四乙酸及其盐;三唑;苯并三唑、2-巯基苯并噻唑、甲苯三唑衍生物、N,N-二亚水杨基-1,2-二氨基丙烷及其混合物的金属钝化剂。
10.使包含至少一种氟烯烃的组合物稳定化的方法,所述方法包括添加有效量的包含至少一种选自1,2-环氧丙烷和1,2-环氧丁烷的环氧化物或式A所示的氟化环氧化物和二苯甲酮衍生物的稳定剂,
其中R2至R5各自是H、具有1至6个碳原子的烷基或具有1至6个碳原子的氟烷基,条件是R2至R5中的至少一个是氟烷基,和
其中所述有效量基于所述组合物的总重量为0.001wt%至10wt%。
11.制冷方法,包括冷凝权利要求1的组合物和此后在要冷却的物体附近蒸发所述组合物。
12.制热方法,包括在要加热的物体附近冷凝权利要求1的组合物和此后蒸发所述组合物。
13.降低包含至少一种氟烯烃的组合物的降解的方法,其中所述降解由制冷、空调或热泵系统中误入空气的存在引起,所述方法包括将有效量的包含至少一种选自1,2-环氧丙烷和1,2-环氧丁烷的环氧化物或式A所示的氟化环氧化物和二苯甲酮衍生物的稳定剂添加到包含至少一种氟烯烃的组合物中,
其中R2至R5各自是H、具有1至6个碳原子的烷基或具有1至6个碳原子的氟烷基,条件是R2至R5中的至少一个是氟烷基,和
其中所述有效量基于所述组合物的总重量为0.001wt%至10wt%。
14.减少包含至少一种氟烯烃的组合物与氧反应的方法,所述方法包括将有效量的包含至少一种选自1,2-环氧丙烷和1,2-环氧丁烷的环氧化物或式A所示的氟化环氧化物和二苯甲酮衍生物的稳定剂添加到包含至少一种氟烯烃的组合物中,
其中R2至R5各自是H、具有1至6个碳原子的烷基或具有1至6个碳原子的氟烷基,条件是R2至R5中的至少一个是氟烷基,和
其中所述有效量基于所述组合物的总重量为0.001wt%至10wt%。
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2007
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- 2007-08-31 WO PCT/US2007/019140 patent/WO2008027511A1/en active Application Filing
- 2007-08-31 CN CN200780032617.XA patent/CN101528887B/zh active Active
- 2007-08-31 CN CN201410260809.8A patent/CN104017544B/zh active Active
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US11130894B2 (en) | 2021-09-28 |
EP2069454A1 (en) | 2009-06-17 |
US20150337192A1 (en) | 2015-11-26 |
US20200115605A1 (en) | 2020-04-16 |
US20170362483A1 (en) | 2017-12-21 |
US11851602B2 (en) | 2023-12-26 |
US20110259022A1 (en) | 2011-10-27 |
WO2008027511A1 (en) | 2008-03-06 |
CN104017544B (zh) | 2017-04-12 |
CN101528887A (zh) | 2009-09-09 |
HK1137472A1 (zh) | 2010-07-30 |
US20210380859A1 (en) | 2021-12-09 |
CN104017544A (zh) | 2014-09-03 |
US9133381B2 (en) | 2015-09-15 |
US10550302B2 (en) | 2020-02-04 |
US20140020416A1 (en) | 2014-01-23 |
US8535555B2 (en) | 2013-09-17 |
HK1201288A1 (zh) | 2015-08-28 |
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