CN107254296A - 稳定的2,3,3,3‑四氟丙烯组合物 - Google Patents

稳定的2,3,3,3‑四氟丙烯组合物 Download PDF

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CN107254296A
CN107254296A CN201710600480.9A CN201710600480A CN107254296A CN 107254296 A CN107254296 A CN 107254296A CN 201710600480 A CN201710600480 A CN 201710600480A CN 107254296 A CN107254296 A CN 107254296A
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tetrafluoropropenes
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B.鲍桑德
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Abstract

本发明涉及稳定的2,3,3,3‑四氟丙烯组合物。本发明涉及稳定组合物(CS)，其包含：至少x重量％的2,3,3,3‑四氟丙烯(99.8≤x<100)；至多y重量％的不饱和化合物(Ia)(0<y≤0.2)，所述不饱和化合物(Ia)选自2,3,3,3‑四氟丙烯的位置异构体和3,3,3‑三氟丙烯(HFO‑1243zf)，所述2,3,3,3‑四氟丙烯的位置异构体例如1,3,3,3‑四氟丙烯(异构体Z和E)和1,1,2,3‑四氟丙烯；以及任选的至多500ppm的3,3,3‑三氟丙炔和/或至多200ppm的1,1,1,2,3‑五氟丙烯(HFO‑1225ye)。

Description

稳定的2,3,3,3-四氟丙烯组合物
本申请是申请号为201180033620.X、申请日为2011年06月20日、发明名称为“稳定的2,3,3,3-四氟丙烯组合物”的专利申请的分案申请。
本发明涉及能够用于制冷和空气调节的包含2,3,3,3-四氟丙烯的稳定组合物。
在蒙特利尔商议了由损耗大气臭氧层的物质所引起的问题，在蒙特利尔签署了强制减少氯氟烃(CFC)的制造和使用的议定书。该议定书已经形成这样的修正案的主题，所述修正案要求放弃CFC并且将规章管理扩展至其它产品，包括氢氯氟烃(HCFC)。
制冷和空气调节工业已经在这些制冷剂的替代方面进行了大量投资，因此氢氟烃(HFC)已经上市。
在机动车工业中，许多国家中的市售车辆的空气调节系统已经由包含氯氟烃(CFC-12)的制冷剂变为对臭氧层的危害较小的氢氟烃(1,1,1,2-四氟乙烷：HFC-134a)制冷剂。然而，从由京都议定书所设定的目标的观点来看，HFC-134a(GWP＝1430)被认为具有高的发热本领(heating power)。制冷剂对温室效应的贡献通过标准即GWP(全球增温潜势)量化，GWP通过将二氧化碳作为基准值1而概述了发热本领。
氢氟烯烃(HFO)具有低发热本领，因而符合京都议定书所设定的目标。文献JP 4-110388公开了作为制冷、空气调节和热泵中的传热剂的2,3,3,3-四氟丙烯(HFO-1234yf)。
为了使制冷剂在商业上被接受，其除了具有作为传热剂的良好性能以外，还尤其必须是热稳定的且与润滑剂相容。这是因为，制冷剂与用于大多数制冷系统内所存在的压缩机中的润滑剂相容是高度期望的。对于制冷系统的使用和效率而言，制冷剂和润滑剂的该组合是重要的；特别地，润滑剂必须在整个操作温度范围内均充分可溶于制冷剂中。
根据文献WO 2008/042066，由于当氟烯烃用作制冷剂时，其能够在与湿气、氧气及其它化合物接触时(可能在高温下)发生分解，因此，推荐使用至少一种胺以使氟烯烃稳定。
此外，已经推荐其它稳定剂(例如二苯甲酮衍生物、内酯以及一些含磷化合物)用于使氟烯烃稳定(WO 2008/027596、WO 2008/027516和WO 2008/027515)。
另外，文献EP 2149543描述了1,1,1,2,3-五氟丙烷(在HFO-1234yf制造中的起始材料)的纯化方法，以便获得1,1,1,2,3-五氟丙烯(HFO-1225ye)含量低于500ppm且三氟丙炔含量低于50ppm的产品。
本申请人公司现已开发了这样的2,3,3,3-四氟丙烯组合物，当将该组合物用于制冷系统中时，其使得热稳定性的改善成为可能。
因此，本发明的主题为包含以下物质的稳定组合物(SC)：至少x重量％的2,3,3,3-四氟丙烯(99.8≤x<100)；至多y重量％的不饱和化合物(Ia)(0<y≤0.2)，所述不饱和化合物(Ia)选自2,3,3,3-四氟丙烯的位置异构体和3,3,3-三氟丙烯(HFO-1243zf)，所述2,3,3,3-四氟丙烯的位置异构体例如1,3,3,3-四氟丙烯(Z和E异构体)和1,1,2,3-四氟丙烯；以及任选的至多500ppm的3,3,3-三氟丙炔和/或至多200ppm的1,1,1,2,3-五氟丙烯(HFO-1225ye)。
根据本发明的稳定组合物可额外包含选自如下的化合物(Ib)的至少一种：1,1,1,2-四氟丙烷(HFC-254eb)、1,1,1,2,3-五氟丙烷(HFC-245eb)、1,1,1,2-四氟乙烷(HFC-134a)、1,1,2-三氟乙烷(HFC-143)、1,1,1,2,3,3-六氟丙烷、六氟丙烯、环六氟丙烯和1,1,1,3,3-五氟丙烯(HFO-1225zc)。
本发明组合物中所存在的组合的化合物(Ib)占至多500ppm。
优选地，所述SC组合物包含：至少99.85重量％的2,3,3,3-四氟丙烯；至多y重量％的不饱和化合物(Ia)(0<y≤0.15)，所述不饱和化合物(Ia)选自2,3,3,3-四氟丙烯的位置异构体和3,3,3-三氟丙烯(HFO-1243zf)，所述2,3,3,3-四氟丙烯的位置异构体例如1,3,3,3-四氟丙烯(Z和E异构体)和1,1,2,3-四氟丙烯；以及任选的至多250ppm的3,3,3-三氟丙炔和/或至多50ppm的1,1,1,2,3-五氟丙烯(HFO-1225ye)。
特别优选的SC组合物包含：至少99.9重量％的2,3,3,3-四氟丙烯；至多y重量％的不饱和化合物(Ia)(0<y≤0.1)，所述不饱和化合物(Ia)选自2,3,3,3-四氟丙烯的位置异构体和3,3,3-三氟丙烯(HFO-1243zf)，所述2,3,3,3-四氟丙烯的位置异构体例如1,3,3,3-四氟丙烯(Z和E异构体)和1,1,2,3-四氟丙烯；以及任选的至多200ppm的3,3,3-三氟丙炔和/或至多5ppm的1,1,1,2,3-五氟丙烯(HFO-1225ye)。
根据本发明的优选实施方案，所述SC组合物包含：99.85-99.98重量％的2,3,3,3-四氟丙烯；0.02-0.15重量％的不饱和化合物(Ia)，所述不饱和化合物(Ia)选自2,3,3,3-四氟丙烯的位置异构体和3,3,3-三氟丙烯(HFO-1243zf)，所述2,3,3,3-四氟丙烯的位置异构体例如1,3,3,3-四氟丙烯(Z和E异构体)和1,1,2,3-四氟丙烯；以及任选的至多200ppm的3,3,3-三氟丙炔和/或至多5ppm的1,1,1,2,3-五氟丙烯(HFO-1225ye)和/或至多400ppm的化合物(Ib)。
根据本发明的稳定组合物展现出能够通过2,3,3,3-四氟丙烯的制造方法(任选地在至少一个分离步骤后)直接获得的优点。
本发明的另一主题是这样的2,3,3,3-四氟丙烯，其具有大于或等于99.8重量％且小于100重量％的纯度，而且，其包含至多0.2重量％的不饱和化合物(Ia)、任选的至多500ppm的3,3,3-三氟丙炔和/或至多200ppm的1,1,1,2,3-五氟丙烯和/或至多500ppm的化合物(Ib)。
本发明的另外的主题是这样的2,3,3,3-四氟丙烯，其具有大于或等于99.9重量％且小于100重量％的纯度，而且，其包含至多0.1重量％的不饱和化合物(Ia)、任选的至多200ppm的3,3,3-三氟丙炔和/或至多5ppm的1,1,1,2,3-五氟丙烯和/或至多500ppm的化合物(Ib)。
2,3,3,3-四氟丙烯能够以至少四个反应步骤从六氟丙烯(HFP)获得：(i)在固相的在加氢催化剂的存在下，使HFP加氢以得到1,1,1,2,3,3-六氟丙烷；(ii)在液相中使用碱金属氢氧化物、或者在气相中在脱卤化氢催化剂的存在下，使步骤(i)中获得的1,1,1,2,3,3-六氟丙烷脱氟化氢以得到1,1,1,2,3-五氟丙烯；(iii)在固相中，在加氢催化剂的存在下，使(ii)中获得的HFO-1225ye加氢以得到1,1,1,2,3-五氟丙烷；(iv)在液相中使用碱金属氢氧化物、或者在气相中在脱卤化氢催化剂的存在下，使步骤(iii)中获得的HFC-245eb脱氟化氢以得到2,3,3,3-四氟丙烯。
2,3,3,3-四氟丙烯能够以至少两个反应步骤从六氟丙烯(HFP)获得：(i)在固相中，在加氢催化剂的存在下，使HFP加氢以得到1,1,1,2,3-五氟丙烷；(ii)在液相中使用碱金属氢氧化物、或者在气相中在脱卤化氢催化剂的存在下，使步骤(i)中获得的HFC-245eb脱氟化氢以得到2,3,3,3-四氟丙烯。
本发明的2,3,3,3-四氟丙烯能够根据如前所述的方法从HFP在HFC-245eb的纯化后和/或在2,3,3,3-四氟丙烯的纯化后获得。
因此，在脱氟化氢步骤之前，例如，通过在6巴的绝对压力下和在80℃的塔底温度和50℃的顶部温度下、以约30个理论塔板和约37的回流比进行蒸馏，使HFC-245eb纯化。
在最后的脱氟化氢步骤之后，使HFO-1234yf经历两次蒸馏。在约13巴的绝对压力、约60℃的塔底温度和约40℃的顶部温度下、且以约35个理论塔板和约500的回流比进行第一次蒸馏。在约11巴的绝对压力、约105℃的塔底温度和约44℃的顶部温度下、且以约30个理论塔板和约4的回流比进行第二次蒸馏。
此外，2,3,3,3-四氟丙烯能够通过在氟化催化剂的存在下在液相或气相中的氢氟化而从1,1,1-三氟-2-氯丙烯获得。因此，能够对获得的2,3,3,3-四氟丙烯进行纯化以得到根据本发明的2,3,3,3-四氟丙烯。
根据本发明的组合物能够在固定式空气调节或机动车空气调节、制冷和热泵中用作传热剂。
本发明的另一主题是与润滑剂结合的如前所述的组合物。
作为润滑剂，可特别提及多元醇酯(POE)、聚亚烷基二醇(PAG)、聚亚烷基二醇酯和聚乙烯基醚(PVE)。
所述PAG润滑剂为氧化烯(氧基亚烷基，oxyalkylene)的均聚物或共聚物形式。优选的PAG是由氧化丙烯(氧基亚烷基，oxypropylene)基组成的均聚物，其在40℃下具有10-200厘沲、有利地30-80厘沲的粘度。所述氧化烯均聚物或共聚物的链末端处的羟基能够或多或少地被-O-CnH2n+1基团(其中n＝1-10)取代；优选n＝1的该基团。
可适用的PAG是具有-O-CnH2n+1基团或每个末端具有羟基的那些。
作为POE，可特别提及具有2-15个原子的线型或支化碳链的羧酸与具有新戊基骨架的多元醇的酯，所述多元醇例如为新戊二醇、三羟甲基丙烷、季戊四醇和二季戊四醇；季戊四醇是优选的多元醇。优选具有4-9个原子的碳链的羧酸的酯。
作为4-9个碳原子的羧酸，可特别提及正戊酸、正己酸、正庚酸、正辛酸、2-乙基己酸、2,2-二甲基戊酸、3,5,5-三甲基己酸、己二酸和丁二酸。
一些醇官能团没有被酯化；但是，比例保持为低。
所选择的POE油可包含相对于-CH2-O-(C＝O)-单元为0-5相对摩尔％的CH2-OH单元。
优选的POE润滑剂是在40℃下具有1-1000厘沲(cSt)、优选10-200cSt、且有利地30-80cSt的粘度的那些。
实验部分
根据标准ASHRAE 97-2007“sealed glass tube method to test the chemicalstability of materials for use within refrigerant systems”进行热稳定性试验。
测试条件如下：
流体的重量：2.2g
润滑剂的重量：5g
温度：200℃
持续时间：14天
将钢材段(length of steel)引入到管中。
向42.2ml玻璃管中引入所述钢材段和润滑剂。随后，在真空下抽空该管，然后向其中加入流体F。然后，焊合该管以使其密闭，并将该管置于200℃烘箱14天。
在该测试的最后，进行各项分析：
-回收气相以通过气相色谱法进行分析：通过GC/MS(联用的气相色谱/质谱)鉴别主要杂质。因此，来自流体F的杂质和来自润滑剂的杂质可被组合。
-对所述钢材段进行称重(测量腐蚀速率)并在显微镜下进行观测。
-分析润滑剂的如下方面：颜色(通过光谱色度法，Labomat DR Lange LICO220型MLG131)、含水量(通过Karl Fischer库仑法，Mettler DL37)和酸值(通过使用0.01N氢氧化钾甲醇溶液(methanolic potassium hydroxide)的定量测定)。
用于该测试的润滑剂是市售的PAG油：PAG ND8。
用于这些试验的流体基本上包含HFO-1234yf(至少99.9重量％)，且然后向该流体中分别加入：300ppm的HFO-1243zf；500ppm的E HFO-1234ze；以及300ppm的HFO-1243zf+500ppm的E HFO-1234ze。
所述实施例显示，化合物(Ia)的存在不损害HFO-1234yf组合物或润滑剂的热稳定性，而且，在一些情况下，改善了所述热稳定性。

Claims (11)

1.稳定组合物(SC)，包含：至少x重量％的2,3,3,3-四氟丙烯(99.8≤x<100)；至多y重量％的不饱和化合物(Ia)(0<y≤0.2)，所述不饱和化合物(Ia)选自2,3,3,3-四氟丙烯的位置异构体和3,3,3-三氟丙烯(HFO-1243zf)，所述2,3,3,3-四氟丙烯的位置异构体例如1,3,3,3-四氟丙烯(Z和E异构体)和1,1,2,3-四氟丙烯；以及任选的至多500ppm的3,3,3-三氟丙炔和/或至多200ppm的1,1,1,2,3-五氟丙烯(HFO-1225ye)。
2.权利要求1的组合物，特征在于，其能够额外包含选自如下的化合物(Ib)的至少一种：1,1,1,2-四氟丙烷(HFC-254eb)、1,1,1,2,3-五氟丙烷(HFC-245eb)、1,1,1,2-四氟乙烷(HFC-134a)、1,1,2-三氟乙烷(HFC-143)、1,1,1,2,3,3-六氟丙烷、六氟丙烯、环六氟丙烯和1,1,1,3,3-五氟丙烯(HFO-1225zc)。
3.权利要求2的组合物，特征在于，所述化合物(Ib)占所述组合物的至多500ppm。
4.前述权利要求中任一项的组合物，特征在于，其包含：至少99.85重量％的2,3,3,3-四氟丙烯；至多y重量％的不饱和化合物(Ia)(0<y≤0.15)，所述不饱和化合物(Ia)选自2,3,3,3-四氟丙烯的位置异构体和3,3,3-三氟丙烯(HFO-1243zf)，所述2,3,3,3-四氟丙烯的位置异构体例如1,3,3,3-四氟丙烯(Z和E异构体)和1,1,2,3-四氟丙烯；以及任选的至多250ppm的3,3,3-三氟丙炔和/或至多50ppm的1,1,1,2,3-五氟丙烯(HFO-1225ye)。
5.前述权利要求中任一项的组合物，特征在于，其包含：至少99.9重量％的2,3,3,3-四氟丙烯；至多y重量％的不饱和化合物(Ia)(0<y≤0.1)，所述不饱和化合物(Ia)选自2,3,3,3-四氟丙烯的位置异构体和3,3,3-三氟丙烯(HFO-1243zf)，所述2,3,3,3-四氟丙烯的位置异构体例如1,3,3,3-四氟丙烯(Z和E异构体)和1,1,2,3-四氟丙烯；以及任选的至多200ppm的3,3,3-三氟丙炔和/或至多5ppm的1,1,1,2,3-五氟丙烯(HFO-1225ye)。
6.前述权利要求中任一项的组合物，特征在于，其包含：99.85-99.98重量％的2,3,3,3-四氟丙烯；0.02-0.15重量％的不饱和化合物(Ia)，所述不饱和化合物(Ia)选自2,3,3,3-四氟丙烯的位置异构体和3,3,3-三氟丙烯(HFO-1243zf)，所述2,3,3,3-四氟丙烯的位置异构体例如1,3,3,3-四氟丙烯(Z和E异构体)和1,1,2,3-四氟丙烯；以及任选的至多200ppm的3,3,3-三氟丙炔和/或至多5ppm的1,1,1,2,3-五氟丙烯(HFO-1225ye)和/或至多400ppm的化合物(Ib)。
7.前述权利要求中任一项的组合物，特征在于，其在固定式空气调节或机动车空气调节、制冷和热泵中用作传热剂。
8.前述权利要求中任一项的组合物，特征在于，其与润滑剂一起使用。
9.前述权利要求中任一项的组合物，特征在于，所述润滑剂选自多元醇酯(POE)、聚亚烷基二醇(PAG)、聚亚烷基二醇酯和聚乙烯基醚(PVE)。
10.2,3,3,3-四氟丙烯，其具有大于或等于99.8重量％且小于100重量％的纯度，而且，其包含至多0.2重量％的不饱和化合物(Ia)、任选的至多500ppm的3,3,3-三氟丙炔和/或至多200ppm的1,1,1,2,3-五氟丙烯和/或至多500ppm的化合物(Ib)。
11.权利要求10的2,3,3,3-四氟丙烯，特征在于，大于或等于99.9重量％且小于100重量％的纯度，而且，包含至多0.1重量％的不饱和化合物(Ia)、任选的至多200ppm的3,3,3-三氟丙炔和/或至多5ppm的1,1,1,2,3-五氟丙烯和/或至多500ppm的化合物(Ib)。
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