CN103313961A - (z)-i-氯-3,3,3-三氟丙烯与氟化氢的类共沸组合物 - Google Patents

(z)-i-氯-3,3,3-三氟丙烯与氟化氢的类共沸组合物 Download PDF

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CN103313961A
CN103313961A CN2011800581682A CN201180058168A CN103313961A CN 103313961 A CN103313961 A CN 103313961A CN 2011800581682 A CN2011800581682 A CN 2011800581682A CN 201180058168 A CN201180058168 A CN 201180058168A CN 103313961 A CN103313961 A CN 103313961A
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R·赫尔斯
H·T·范
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Honeywell International Inc
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Abstract

本发明公开了(Z)-1-氯-3，3，3-三氟丙烯(1233zd(Z))与氟化氢的共沸和类共沸混合物。该组合物在1233zd(Z)制备中用作中间体。后者化合物可用作无毒、零臭氧消耗的氟代烃，其用作溶剂、发泡剂、制冷剂、清洁剂、气溶胶推进剂、传热介质、电介质、灭火组合物和动力循环工作流体。

Description

(Z)-I-氯-3,3,3-三氟丙烯与氟化氢的类共沸组合物
相关申请的交叉引用
本申请要求2010年12月3日提交的共同拥有的、共同未决的美国临时专利申请序列号61/419322的国内优先权，其公开内容在此通过引用并入本文。
发明领域
本发明涉及(Z)-1-氯-3，3，3-三氟丙烯(顺-1233zd或1233zd(Z))与氟化氢(HF)的共沸和类共沸组合物。
发明背景
近年来已存在一些忧虑，担忧某些长寿命氟碳化合物可能导致(虽然以较小方式)全球变暖。因此，全世界努力使用具有短大气寿命并因此不久留于大气中的氟取代烃。在这方面，具有低全球变暖潜势的(Z)-1-氯-3，3，3-三氟丙烯(1233zd(Z))被认为是用于溶剂中和作为发泡剂的某些氟碳化合物例如141b的替代物。
1223zd(Z)的制备已成为受关注的主题以提供用于发泡剂、制冷剂、清洁剂、气溶胶推进剂、传热介质、电介质、灭火组合物和动力循环工作流体的环境有利的产品。本领域已知通过使氟化氢与各种氢氯烃反应制备氟代烃如1233zd(Z)。
因为已知许多CFCs为臭氧消耗性化合物，这些化合物的使用已被缩减，这有利于商业上更可接受的化学物质。在某些情况下，已发现替代CFC化合物既有效又更加环境友好。
作为一个实例，已发现1-氯-3，3，3-三氟丙烯(1233zd)具有广泛用途，例如除其它用途外用作传热剂、用作发泡剂、和用作溶剂。参见例如，美国专利号7,833,433，名称为“使用含有三氟一氯丙烯的传热组合物的传热方法”、美国专利公开号2008-0207788，名称为“含有氟取代卤素的发泡剂、可发泡组合物、泡沫和制品、和制备它的方法”、和美国专利号6,362,383，名称为“氯代烃的氢氟化”，它们公开了这类用途的实例。
化合物1233zd可通过多种不同方法制备。参见，例如，美国专利号7,829,747，名称为“3-氯-1，1，1，3-四氟丙烷脱氟化氢至1-氯-3，3，3-三氟丙烯的方法”、美国专利号5,710,352，名称为“制备1，1，1，3，3-五氟丙烷和1-氯-3，3，3-三氟丙烯的气相方法”、美国专利号6,111,150，名称为“制备1，1，1，3，3-五氟丙烷的方法”、和美国专利号6,844,475，名称为“1-氯-3，3，3-三氟丙烯(HCFC-1233zd)的低温制备”，它们描述了几种制备1233zd的方法。
以上所引用的全部文献在此通过引用整体并入本文。
发明概述
现已发现在基本上纯的1233zd(Z)的制备中，重要的中间体为1233zd(Z)与氟化氢(HF)的共沸物或类共沸混合物。该二元中间体，一旦形成，可此后通过萃取或蒸馏技术分离成其组成部分。在标准大气压下，化合物1233zd(Z)具有约18℃的沸点而HF具有约20℃的沸点。发现这些共沸物或类共沸组合物不仅可在1233zd(Z)的制备中用作中间体，而且它们另外可用作用于自金属移除表面氧化的溶剂和组合物。
另外，形成1233zd(Z)与HF的共沸或类共沸组合物可用于分离1233zd(Z)与杂质的混合物。当需要分离1233zd(Z)与杂质的混合物时，加入HF以形成1233zd(Z)与HF的共沸混合物，然后自该共沸混合物移除杂质，例如通过蒸馏、洗涤(scrubbing)或其它已知方式。
本发明的一个实施方案提供了基本上由(Z)-1-氯-3，3，3-三氟丙烯(1233zd(Z))和氟化氢(HF)组成的共沸组合物。
本发明的另一个实施方案提供了基本上由约1至约95wt％的氟化氢和约5至约99wt％的1233zd(Z)组成的共沸或类共沸组合物，该组合物在约3psia至约73psia的压力下具有约0℃至约60℃的沸点。在某些实施方案中，该组合物由氟化氢和(Z)-1-氯-3，3，3-三氟丙烯(1233zd(Z))组成。在某些实施方案中，氟化氢以约5至约90wt％的量存在。在某些实施方案中，氟化氢以约20至约35wt％的量存在。本发明的某些实施方案在约3psia至约73psia的压力下具有约0℃至约61℃的沸点。
本发明的另一个实施方案提供了形成共沸或类共沸组合物的方法，其基本上由混合约1至约95wt％的氟化氢和约5至约99wt％的(Z)-1-氯-3，3，3-三氟丙烯(1233zd(Z))的步骤组成，该组合物在约3psia至约73psia的压力下具有约0℃至约60℃的沸点。在某些实施方案中，所述组合物由氟化氢和(Z)-1-氯-3，3，3-三氟-丙烯(1233zd(Z))组成。在某些实施方案中，氟化氢以约5至约90wt％的量存在。在某些实施方案中，氟化氢以约20至约35wt％的量存在。在某些实施方案中，氟化氢以约26±3wt％的量存在。在本发明的某些实施方案中，所述组合物在约3psia至约73psia的压力下具有约0℃至约61℃的沸点。在某些实施方案中，所述组合物在约14.7psia的压力下具有约25℃的沸点。
在某些实施方案中，1233zd(Z)可通过提取HF而自1233zd(Z)与HF的类共沸混合物分离。在某些实施方案中，使用水或其它含水溶液完成HF的提取。在某些实施方案中，使用硫酸完成HF的提取。在某些实施方案中，通过蒸馏，例如通过提取蒸馏、或变压蒸馏完成HF的提取。
本发明的(Z)-1-氯-3，3，3-三氟丙烯(1233zd(Z))与氟化氢的共沸和类共沸混合物可在1233zd(Z)的制备中用作中间体。经纯化的这种物质可用作无毒、零臭氧消耗的氯氟烃，其可用作溶剂、发泡剂、制冷剂、清洁剂、气溶胶推进剂、传热介质、电介质、灭火组合物和动力循环工作流体。
附图简要说明
图1显示了0℃、25℃、和60℃下测量的实施例1中形成的混合物的蒸汽压图。
发明详述
可如美国专利号7,829,747中所述形成1233zd(Z)与HF的二元共沸物，其中使244fa脱氟化氢以生成1233zd(Z)、HF和其它组分例如(E)-1-氯-3，3，3-三氟丙烯、氯化氢、1，3，3，3-四氟丙烯、1，1，1，3，3-五氟丙烷。通过移除其它化合物留下1233zd(Z)与HF的二元共沸物。
1233zd(Z)与HF形成共沸和类共沸混合物。流体的热力学状态通过其压力、温度、液体组成和蒸气组成限定。对于真正的共沸组合物，液体组成和气相组成在给定的温度和压力范围下基本上相等。在实际应用中这意味着在相变期间各组分无法分离。为了本发明的目的，类共沸组合物意指就其恒沸特征和沸腾或蒸发时不分馏的趋向而言，表现得像真正的共沸物的组合物。在沸腾或蒸发期间，如果的确有变化，液体组成仅轻微改变。这与非类共沸组合物形成对比，在非类共沸组合物中蒸发或冷凝期间液体组成和蒸气组成显著地变化。
确定候选混合物是否属于本发明含义之内的类共沸的一种方式是在预期能将该混合物分离成其各单独组分的条件下蒸馏它的样品。如果混合物为非共沸或非类共沸，则该混合物将分馏，即分离成它的各个组分，最低沸点的组分最先蒸馏出来，依此类推。如果混合物为类共沸，则将获得某些有限量的第一馏分，其含有全部的混合物组分并恒沸或表现得像单一物质。
类共沸组合物的另一个特征为存在一系列包含不同比例的相同组分的类共沸组合物。全部这类组合物均被本文所用的术语类共沸所覆盖。作为实例，公知地在不同的压力下给定共沸物的组成会至少稍微变化，如该组合物的沸点那样。因此两组分的共沸物代表一类独特的关系，但取决于温度和/或压力组成可变。如本领域所公知地，共沸物的沸点会随压力变化。
如本文所用，共沸物为液体混合物，其展示出相对于周边混合物组成的沸点而言最大或最小的沸点。共沸物或类共沸组合物为两种或更多种不同组分的混合物，当在给定压力下为液体时其将在基本上恒定的温度下沸腾，该温度可高于或低于所述组分的沸腾温度，并且将提供与沸腾中的液体组成基本上相同的蒸气组成。
为了本发明的目的，共沸组合物定义为包括类共沸组合物，其意指表现得像共沸物的组合物，即具有恒沸特征或者沸腾或蒸发时不分馏的趋向。因此，沸腾或蒸发期间形成的蒸气组成与初始液体组成相同或基本上相同。因此，在沸腾或蒸发期间，液体组成，如果的确改变，仅极小程度或可忽略程度地改变。这与非类共沸组合物形成对比，在非共沸类组合物中在沸腾或蒸发期间液体组成显著程度地变化。
因此，共沸物或类共沸组合物的本质特征为在给定压力下，液体组合物的沸点固定并且沸腾组合物上方的蒸气组成基本上为沸腾的液体组合物的组成，即基本上不发生液体组合物各组分的分馏。当共沸物或类共沸液态组合物在不同压力下经历沸腾时，共沸组合物中各组分的沸点和重量百分比可变化。因此，共沸物或类共沸组合物可借助其组分之间存在的关系，或借助所述组分的组成范围，或者借助特征为在给定压力下具有固定沸点的组合物的各个组分的精确重量百分比来定义。
本发明提供了一种组合物，其包含有效量的HF和1233zd(Z)以形成共沸物或类共沸组合物。有效量意指当与其它组分混合时导致形成共沸物或类共沸混合物的各组分的量。本发明组合物优选为基本上仅由HF与1233zd(Z)的组合组成的二元共沸物。
在优选实施方案中，本发明组合物含有约1至约95wt％的HF，优选约5wt％至约90wt％的HF和最优选约20wt％至约35wt％的HF。在优选实施方案中，本发明组合物含有约5至约99wt％的1233zd(Z)，优选约10wt％至约95wt％和最优选约65wt％至约80wt％。本发明组合物在约3psia至约73psia的压力下具有约0℃至约60℃的沸点。已发现具有约26±3wt％的HF和约74±3wt％的1233zd(Z)的共沸或类共沸组合物在约25℃和14.7psia下沸腾。以下非限制性实施例用于阐述本发明。
实施例1
将60g的1233zd(Z)溶于40g的HF中以形成非均相共沸混合物。该实验在25℃和14.6psia下进行。
实施例2
混合只含1233zd(Z)和HF的二元组合物以形成不同组成的非均相共沸混合物。在约0℃、25℃和60℃下测量混合物的蒸汽压并得到以下结果。
表1显示了在约0℃、25℃、和61℃的恒定温度下，1233zd(Z)和HF的蒸汽压测量值随HF重量百分比组成的变化。数据显示1233zd(Z)和HF形成非均相混合物。
表1 0℃、25℃和60℃下1233zd(Z)和HF的压力vs.组成测量值
Figure BPA00001751756100051
这些数据也显示了该混合物为共沸物，因为1233zd(Z)和HF混合物在所有所示混合比例下的蒸汽压比单独的1233zd(Z)和HF(即如第一行当HF为0wt％和1233zd(Z)为100wt％时，以及最后一行其中1233zd(Z)为0wt％和HF为100wt％所示)更高。表1数据也以图形式显示于图1中。
实施例3
1233zd(Z)/HF混合物的共沸组成还通过气-液-液平衡(VLLE)实验来证实。在此，于26℃下将66.6g的1233zd(Z)溶于33.4g的HF中以形成非均相混合物(肉眼观察)。取样蒸气组合物、上部液体(富HF)、和底部液体(有机)。结果显示共沸组成在26℃下为约26±3wt％的HF。
如本文所用，单数形式“一个(a)”、“一种(an)”和“该(the)”包括复数，除非上下文另有明确说明。此外，当量、浓度、或其他值或参数以范围、优选范围、或较高优选值和较低优选值的列表给定时，应理解具体公开了由任意较高范围限度或优选值和任意较低范围限度或优选值的任何配对形成的所有范围，无论是否单独公开了这些范围。当本文陈述数值范围时，除非另有说明，该范围意欲包括其端点、和处于该范围之内的全部整数和分数。当定义范围时，不意于将本发明的范围限制于所陈述的具体值。
虽然本发明已通过参考优选实施方案来具体显示和描述，本领域技术人员容易理解的是可作出多种变化和修正而不背离本发明的范围。意欲将权利要求书解释为覆盖了所公开的实施方案、以上已公开的那些替代方案和其全部等同方案。

Claims (11)

1.共沸或类共沸组合物，其基本上由约1至约95wt％的氟化氢与约5至约99wt％的(Z)-1-氯-3，3，3-三氟丙烯(1233zd(Z))组成，该组合物在约3psia至约73psia的压力下具有约0℃至约60℃的沸点。
2.权利要求1的组合物，在约3psia至约73psia的压力下具有约0℃至约61℃的沸点。
3.权利要求1的组合物，其中氟化氢以约5至约90wt％的量存在。
4.权利要求1的组合物，其中氟化氢以约20至约35wt％的量存在。
5.权利要求1的组合物，具有约26±3wt％的HF和约74±3wt％的1233zd(Z)，在约14.7psia的压力下具有约25℃的沸点。
6.形成共沸或类共沸组合物的方法，其基本上由混合约1至约95wt％的氟化氢和约5至约99wt％的(Z)-1-氯-3，3，3-三氟丙烯(1233zd(Z))的步骤组成，该组合物在约3psia至约73psia的压力下具有约0℃至约60℃的沸点。
7.权利要求6的方法，其中氟化氢以约5至约90wt％的量存在。
8.权利要求6的方法，其中氟化氢以约20至约35wt％的量存在。
9.权利要求6的方法，其中氟化氢以约26±3wt％的量存在。
10.权利要求6的方法，其中所述组合物在约3psia至约73psia的压力下具有约0℃至约60℃的沸点。
11.权利要求6的方法，其中所述组合物在约14.7psia的压力下具有约25℃的沸点。
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