CN1169977A - 制造双酚的方法 - Google Patents

制造双酚的方法 Download PDF

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CN1169977A
CN1169977A CN97113272A CN97113272A CN1169977A CN 1169977 A CN1169977 A CN 1169977A CN 97113272 A CN97113272 A CN 97113272A CN 97113272 A CN97113272 A CN 97113272A CN 1169977 A CN1169977 A CN 1169977A
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phenol
bis
tar
isomer
crystallizer
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CN1090168C (zh
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G·M·基辛格
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SHPP Global Technologies BV
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General Electric Co
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Abstract

基于在离子交换树脂的存在下酮和苯酚的缩合作用来制备和回收双酚的一体化方法。

Description

制造双酚的方法
本发明涉及制造双酚的方法。
二羟酚在许多工业应用中获得了显著的成功。二羟酚可用于工业制造包括多芳基化合物、聚酰胺、环氧基树脂、聚醚酰亚胺、聚砜和聚碳酸酯在内的多种聚合体。人们明显注意到二羟酚的工业制造。例如，众所周知苯酚与具体的醛或酮的酸性催化反应能制备4，4’-二羟酚。具体来讲，苯酚与酮反应时，生成二羟酚2，2’-双(4-羟基-苯基)丙烷(也就是已知的双酚-A或BPA)，后者在制造聚碳酸酯、多芳基化合物和共聚多酯碳酸酯、还有环氧基树脂方面具有特别的实用性。为了制造这类聚合体(具体来讲是聚碳酸酯)，双酚-A必须特别纯，例如用颜色测量。另外，既然二羟酚是最终聚合体的基本部分，方法应该在选择性、收率和能耗方面是特别有效的。
本领域有大量指导双酚A制备的参考文献。许多年来，专利技术中描述的以及工业上使用的一个特别有用的催化剂是盐酸(HCl)。在这个先前已知的方法中，以分批/连续方式在玻璃加衬的容器中加入苯酚、丙酮和来自先前合成的再再循环副产品。将混合物连续保持在HCl气体正压下，后者催化BPA及其副产品的生成。丙酮反应至基本上完全耗尽。将所述苯酚/丙酮反应的流出物送至酸排除装置。在该装置中排除HCl、水和一些苯酚、以及只是微量的未反应丙酮。一旦除去HCl，将含有冷凝水、BPA和未反应苯酚和丙酮在内的物流残留物送至苯酚汽提装置，通过蒸馏除去苯酚和丙酮。本发明方法中除去了HCl排除步骤，使得苯酚/丙酮反应的流出物直接送至苯酚汽提装置。然后将蒸馏装置的BPA流出物送至另一装置，通过分步融化结晶法进行纯化。该方法涉及通过在降膜式动态结晶器中分步融化结晶以纯化不纯的BPA。通过在冷却的转鼓上固化BPA，从融化结晶器中回收纯化的BPA薄片。将来自融化结晶器的循环残留物(含有BPA、苯酚、焦油和异构体)送至回收装置，以从焦油和异构体中分离出苯酚和双酚-A。然后将BPA送回融化结晶器的进料处，而将苯酚、焦油和异构体送至焦油/异构体裂化器。焦油/异构体裂化器是组合反应器/蒸馏塔，它使用诸如氢氧化钠或硫酸之类的裂化催化剂以分解异构体和其它杂质。将从焦油/异构体裂化器中回收的苯酚送回反应中，来自该裂化器的残留物或焦油或者出售或用于燃料燃烧。
用先有技术描述的带有再循环杂质的HCl法获得以下结果。
                             表1反应进料                       反应流出物成分        范围               成分         范围H2O       0.2％-0.4％         H2O         0.2％-3.0％丙酮       7.0％-8.0％         丙酮         0.0％-0.2％苯酚      81.0％-88.0％        苯酚        58.0％-65.0％p，p’-BPA 3.0％-8.0％         p，p’-BPA  28.0％-34.0％0，p’-BPA 0.5％-1.0％         0，p’-BPA   1.0％-1.5％二聚体     0.2％-0.3％         二聚体      0.25％-0.35％BPXI       0.2％-0.3％         BPXI        0.25％-0.3％苯并二氢吡喃0.2％-0.4％         苯并二氢吡喃0.35％-0.5％螺              0              螺                0BPXII      0.1％-0.2％         BPXII        0.1％-0.2％未知物    0.04％-0.5％         未知物       0.7％-0.9％HCl          气层              HCl          1.0％-3.0％
尽管上述方法将反应物高度转化为BPA，但需要耐酸设备。盐酸具有高度的腐蚀性，一般的金属反应器和管道必须经常更换。通常使用玻璃加衬的容器和其它进口设备；然而，使用这种设备需要十分小心，因为它容易损坏。而且，酸的损耗大，这需要酸代替物以用于连续有效运行。另外，腐蚀剂要求中和酸，产生基本上作为废物排出的盐。另一缺点是设备需要再生HCl并且除去水。
在专利4,375,567(在此并入作为参考)中描述了使用离子交换树脂(IER)催化剂制造BPA的方法。’567中描述的方法包括，将流出物送至BPA浓缩器、结晶器和固体/液体分离器中完成BPA从其反应副产物和起始反应物中的分离，将BPA再循环至含有离子交换催化剂的异构化区域完成将所述2，4’-二羟基-2，2-二苯基丙烷转化为2，2-双(4-羟基苯基)丙烷，而后者再循环至双酚进料罐中。尽管该方法不需要耐酸设备，但它需要使用多个纯化加工设备。
本发明基于产生高纯度双酚的完全一体化的双酚方法。另外，本发明比目前已知的任何一体化方法都更简单。它使用的能耗少，减少有机物的喷射，降低运行的复杂性，也减少设备的维修。
本发明提供制造双酚的方法，包括：
(a)在离子交换树脂催化剂的存在下将苯酚与酮反应，产生双酚；
(b)在苯酚排除装置中从步骤(a)产生的双酚中分离出未反应苯酚；
(c)在脱水装置中从所述分离的苯酚中提取水和丙酮，以获得干燥的苯酚，并将干燥的苯酚返回至所述的反应器；
(d)在废水纯化装置中从步骤(c)提取的丙酮中分离出提取的水，并将所述的丙酮返回到所述反应器中，将所述水转移至水排出装置中；
(e)通过在降膜式动态结晶器中分步融化结晶，在融化结晶器中从在苯酚排除装置中获得的双酚中分离出苯酚、异构体和焦油；
(f)从所述融化结晶器中将包含双酚、苯酚、焦油和异构体的再循环残留物转移至再循环回收装置中；
(g)从再循环回收装置中回收双酚，并将回收的双酚返回至融化结晶器中；
(h)将残留物苯酚、焦油和异构体从所述再循环回收装置转移至焦油/异构体回收装置；
(i)从焦油/异构体裂化器中回收苯酚，其中将苯酚返回到反应器中并将焦油加以处理；
(j)在双酚回收装置中回收在融化结晶器中纯化的双酚。
附图是表明本发明方法一个实施方案的框图。
为了使本领域的技术人员能够更好地实施本发明，我们对图做出说明。示意图表明，在反应器(5)中，在离子交换树脂(IER)催化剂的存在下，将通常过量的苯酚与酮反应，以生产双酚粗品。这种反应器可以是分批反应器、连续反应器或本领域技术人员使用的、以完成该类型反应的其它反应器。反应器(5)与苯酚排除装置(10)相连，在苯酚排除装置(10)中从双酚中分离出苯酚，留下含有低于1％苯酚的双酚粗品。将来自苯酚排除装置(10)的双酚粗品送入融化结晶器(25)中，而将排除的苯酚和未反应的丙酮/水流送入脱水装置(15)。然后将来自脱水装置(15)的废水(含有少量苯酚、丙酮和副产物)送入废水纯化装置(20)。来自脱水装置(15)底部的苯酚再循环回反应器(5)中。然后将从废水纯化装置(20)回收的苯酚和丙酮再循环回反应器(5)中。将从融化结晶器(25)中纯化的双酚送入双酚回收装置(40)，而将来自融化结晶器(25)的再循环残留物(含有双酚、苯酚、焦油和异构体)送入再循环回收装置(30)。将再循环回收装置(30)回收的双酚返回至融化结晶器(25)，而来自再循环回收装置(30)的剩余的产物(苯酚、焦油和异构体)流到焦油/异构体裂化器(35)中。从焦油/异构体裂化器(35)回收的苯酚返回至反应器(5)，而焦油作为燃烧值燃烧或出售。
反应包括使苯酚和丙酮通过IER催化剂的固定床。该反应可以以两种方法中的一种进行；第一种方法是该反应一直进行到丙酮基本上耗尽为止，或第二种方法也是最好的，是通过使用部分丙酮转化(PAC)法进行该反应。专利5,315,042描述的PAC法(在此并入作为参考)包括在酸性催化剂的存在下，在加快流速条件下或增加通过量使苯酚和丙酮接触，使得BPA的初始产量增加。在丙酮耗尽前，从流出物流中分离出丙酮和BPA，藉此减少BPA的停留时间，以及减少不需要的副产物和颜料。IER反应器的流出物(不含“游离酸”，只含有未反应丙酮、苯酚、双酚-A和其副产物)与诸如3-巯基丙酸、或乙硫醇、甲硫醇或丙硫醇之类的助催化剂一起送入排除体系以除去反应水。残留的丙酮和苯酚。在基本上无水的条件下(低于2％(重量)的水，最好低于0.2％(重量)的含水率)将苯酚和丙酮加热至反应温度以起始反应。让反应物通过离子交换树脂的固定的多孔床，稍微施加压力以维持适当的流动，尽管重力压力也是令人满意的。
在苯酚排除装置(10)中可以通过氮气解附或通过蒸馏除去苯酚。推荐的双酚粗品成分中含有的苯酚不高于10％(重量)。较优选的是苯酚低于大约7％(重量)双酚粗品成分。再较优选的是双酚粗品成分含有低于大约1％的苯酚。
将来自苯酚排除装置的双酚粗品送入融化结晶器(25)中进行纯化。方法涉及通过在例如如专利5,475,152(在此并入作为参考)中描述的降膜式动态结晶器中进行分部融化结晶，纯化双酚粗品。在多阶段分部融化结晶器中，在每一连续的阶段中通过结晶相、部分融化(发汗)和总融化使结晶成分的纯度升级。推荐的实施分部融化结晶的装置是由瑞士Sulzer Brothers，Ltd.的子公司Sulzer Canada，Inc.生产的。以该方式可以获得无外来溶剂或其它物质污染的高纯的双酚。所述的双酚粗品与对对双酚一起可以含有诸如邻对双酚、苯并二氢吡喃、BPXs、二聚体、螺二茚(spirobiindane)和异丙烯基苯酚之类的副反应产物。所述融化结晶操作产生高于大约99.5％纯度的纯化双酚产物，更好是高于大约99.8％纯度，最好是高于大约99.5％纯度。
将来自融化结晶装置(25)的副产物(含有双酚、苯酚、焦油和异构体)送入再循环回收装置(30)。在再循环回收装置(30)中回收的双酚返回至融化结晶器进料处，而苯酚、焦油和异构体流到焦油/异构体裂化器(35)中。
焦油/异构体裂化器(35)是组合反应器/蒸馏塔，它使用诸如氢氧化钠或硫酸之类的腐蚀剂以分解焦油、异构体和其它残留物。残留物在大约270°F蒸馏以除去轻馏分，在372-390°F、大约4mmHg压力下蒸馏以除去中间馏分。焦油/异构体裂化器(35)最好在大约310-510°F、大气压下运行。从焦油/异构体裂化器(35)中回收的苯酚返回到反应器(5)中，来自该裂化器的残留物或焦油或者出售或用于燃料燃烧。
在双酚回收装置(40)中回收来自融化结晶装置(25)的融化的纯化双酚。所述双酚可以通过在冷却转鼓上固化熔体作为薄片回收或作为来自造粒操作的“颗粒”回收。两种方法在化学工业上回收融化产物中都是众所周知的。
将来自本方法苯酚排除装置(10)的未反应苯酚送入干燥器中，从在大约126-202°F取出的所述苯酚中提取水和丙酮。这是来自部分丙酮转化反应的未反应丙酮和水以及一些共沸物部分的苯酚。主要部分的苯酚(除去丙酮和水/苯酚共沸物)再循环回反应器(5)中。
然后将水和未反应丙酮与微量苯酚一起送入废水纯化装置(20)，其中将所述未反应的丙酮和苯酚返回到反应器(5)，而水转移至废水排出设备。推荐的方法使用诸如甲苯或甲基异丁酮之类的溶剂，在逆流式液液提取柱上从反应水中除去丙酮和苯酚。该水在排到废水处理厂除去溶剂之前通过汽提塔加工除去溶剂。从溶剂中馏出苯酚和丙酮，然后进行分离，再返回到反应中。
可以用带有再循环杂质或不带有再循环杂质的本体助催化剂或附体助催化剂进行生产。
                    I
以下描述使用带有再循环杂质的本体助催化剂的生产：
使用的反应器能够利用或者完全丙酮转化技术或者部分丙酮转化技术，重时空速(WHSV)为0.2-5.0。反应器进料流包含74-84％(重量)苯酚、3.0-8.0％(重量)丙酮、硫醇助催化剂，余物包含再循环双酚-A和再循环杂质。反应器流出物的温度一般为175-200°F。用真空蒸馏或惰性气体解附完成苯酚的汽提。一般蒸馏塔底部的温度为275-325°F，其压力低于大气压，为100-175mmHg。将诸如氮气之类的惰性气体逆流通至填料塔的产物进料处，苯酚凝结并从气流流中分离出来，完成解附过程。一般解吸塔的底部和惰性气体的温度为325-385°F。送入结晶器的来自蒸馏/解附的物料成分大约如下：70-85％(重量)p，p’-双酚-A和15-30％(重量)反应副产物。将来自该步骤的残留物送至再循环回收装置，双酚-A在此回收，然后返回至融化结晶器的进料处。来自再循环回收装置的轻馏分和重馏分部分进行再循环，部分清除至催化裂化器中，产生苯酚。回收的苯酚再循环回反应中。终产物的成分应该为大约99.9+％(重量)p，p’-双酚-A和大约0.1％(重量)其它物质。
用上述公开的PAC反应方法获得以下结果。
                               表2
            反应进料成分      范围H2O      0.04％-0.15％丙酮         3％-8％苯酚        74％-84％p，p’-BPA   8％-15％0，p’-BPA 2.7％-3.4％二聚体     0.4％-0.55％BPXI         1％-1.4％苯并二氢吡喃0.7％-1.1螺               0BPXII       0.3％-0.5％未知物      0.0％-0.03％              反应流出物成分         范围H2O        0.95％-1.5％丙酮         0.5％-1.5％苯酚          58％-65％p，p’-BPA    24％-32％0，p’-BPA     3％-4％二聚体       0.5％-0.8％BPXI         1.3％-1.8％苯并二氢吡喃0.85％-1.2％螺                0BPXII        0.3％-0.5％未知物       0.0％-0.03％
用上述公开的带有杂质的完全丙酮转化反应方法获得以下结果。
                            表3反应进料                   反应流出物成分      范围            成分        范围H2O      0.025％-0.35％   H2O        1.3％-1.8％丙酮          3％-8.％     丙酮        0.1％-0.3％苯酚         74％-84％     苯酚         62％-68％p，p’-BPA    8％-15％     p，p’-BPA   21％-27％0，p’-BPA    2％-3％      0，p’-BPA  2.0％-3.2％二聚体        3％-4％      二聚体      3.0％-4.2％BPXI        0.5％-1％      BPXI        0.5％-1.5％苯并二氢吡喃0.5％-1％      苯并二氢吡喃0.5％-1.5％螺          0.1％-0.4％    螺          0.1％-0.7％BPXII      0.25％-0.75％   BPXII       0.3％-0.9％未知物      0.0％-0.1％    未知物      0.0％-0.2％
               II
以下描述使用PAC和使用带有和不带有再循环杂质的附体助催化剂的生产：
IER反应器能够用2-35％(mole)用巯基乙胺中和的磺酸基团，该体系利用部分丙酮转化技术，重时空速(WHSV)为0.2-20.0。反应器进料流包含纯苯酚、3.0-8.0％(重量)丙酮、以及再循环杂质。反应器流出物的温度一般为150-200°F。用真空蒸馏或惰性气体解附可以完成苯酚的汽提。一般蒸馏塔底部的温度为275-325°F，其压力低于大气压，为100-175mmHg。通过将诸如氮气之类的惰性气体逆流通至填料塔的产物进料处，苯酚凝结并从气流流中分离出来，完成解附过程。一般解吸塔底部和惰性气体的温度为325-385°F。送入结晶器的来自蒸馏/解附的物料成分大约如下：80-96％(重量)p，p’-双酚-A和4-20％(重量)反应副产物。将来自该步骤的残留物送至再循环回收装置，双酚-A在此回收，然后返回至融化结晶器的进料处。来自再循环回收装置的轻馏分和重馏分部分进行再循环，部分清除至催化裂化器中产生苯酚。回收的苯酚再循环回反应中。终产物的成分应该为大约99.9+％(重量)p，p’-双酚-A和大约0.1％(重量)的其它物质。
用上述公开的不带杂质的方法获得以下结果。
                    表4反应进料            反应流出物成分     范围       成分        范围H2O        0       H2O       0.5％-1％丙酮     3％-8％    丙酮       0.1％-3％苯酚    92％-97％   苯酚        83％-87％p，p’-BPA  0       p，p’-BPA  11％-30％0，p’-BPA  0       0，p’-BPA 0.3％-0.8％二聚体      0       二聚体    0.03％-0.07％BPXI        0       BPXI       0.1％-0.7％苯并二氢吡喃0       苯并二氢吡喃    0螺          0       螺         0.0％-0.03BPXII       0       BPXII      0.0％-0.6％未知物      0       未知物    0.04％-0.1％
用上述公开的带有再循环杂质的方法获得以下结果。
                             表5反应进料                     反应流出物成分           范围               成分      范围H2O       0.25％-0.35％       H2O      0.75％-1.2％丙酮          3％-8％          丙酮       0.5％-3％苯酚         74％-84％         苯酚        67％-71％p，p’-BPA    8％-15％         p，p’-BPA  17％-30％0，p’-BPA    2％-3％          0，p’-BPA   2％-3％二聚体        3％-4％          二聚体       3％-4％BPX I       0.5％-1％          BPXI       0.9％-11％苯并二氢吡喃0.5％-1％          苯并二氢吡喃0.5％-0.7％螺          0.1％-0.4％        螺        0.08％-0.12％BPX II     0.25％-0.75％       BPXII        1％-1.3％未知物       0.0％-0.1％       未知物     0.9％-1.1％
如表所示，IER反应提供了与HCl反应相当不同的结果。然而，一体化方法的终产物与先有技术方法的终产物相同。用上述公开的方法得到以下终产物的结果。
                            表6先有技术的方法                 发明的方法HCl结晶器的流出物            IER结晶器的流出物成分        平均值           成分        平均值p，p’-BPA 99.9040％         p，p’-BPA 99.9091％0，p’-BPA  0.0610％         0，p’-BPA  0.0350％二聚体      0.0120％         二聚体      0.0081％BPXI        0.0030％         BPXI        0.0061％苯并二氢吡喃0.0040％        苯并二氢吡喃 0.0003％螺          0.0000％        螺           0.0000％BPXII       0.0010％        BPXII        0.0114％未知物      0.0150％        未知物       0.0300％
我们未预期到所述IER反应方法产生如此高纯度的双酚，同时使用的能耗少，并且简化了无HCl方法中使用的有害化学药品的一体化双酚反应方法。消除了氯的射出(每1 00磅双酚6磅33％HCl)。另外，本发明方法中使用的设备的寿命是无限的，而HCl方法中设备的寿命是有限的。表明本发明令人惊讶地提供的双酚生产方法比先前已知的双酚方法更有效、更可靠而且环境更安全。

Claims (17)

1.制造双酚的方法，包括：
(a)在离子交换树脂催化剂的存在下将苯酚与酮反应，产生双酚；
(b)在苯酚排除装置中从步骤(a)产生的双酚中分离出未反应的苯酚；
(c)在脱水装置中从所述分离的苯酚中提取水和丙酮，以获得干燥的苯酚，并将干燥的苯酚返回到所述的反应器中；
(d)在废水纯化装置中从步骤(c)提取的丙酮中分离出提取的水，并将所述的丙酮返回到所述反应器中，将所述水转移至水排出装置中；
(e)通过在降膜式动态结晶器中分步融化结晶，在融化结晶器中从在苯酚排除装置中获得的双酚中分离出苯酚、异构体和焦油；
(f)从所述融化结晶器中将包含双酚、苯酚、焦油和异构体的再循环残留物转移到再循环回收装置中；
(g)从再循环回收装置中回收双酚，并将回收的双酚返回到融化结晶器中；
(h)从所述再循环回收装置中将残留物苯酚、焦油和异构体转移到焦油/异构体回收装置中；
(i)从焦油/异构体裂化器中回收苯酚，其中将苯酚返回到反应器中并将焦油加以处理；
(j)在双酚回收装置中回收在融化结晶器中纯化的双酚。
2.按照权利要求1的方法，其中纯化双酚的纯度高于约99.8％。
3.按照权利要求2的方法，其中纯化双酚的纯度高于约99.9％。
4.按照权利要求1的方法，其中双酚是双酚-A。
5.按照权利要求1的方法，其中过量的苯酚与酮反应。
6.按照权利要求1的方法，其中在步骤(a)中苯酚与酮的反应利用部分丙酮转化法。
7.按照权利要求1的方法，其中反应是连续的过程。
8.按照权利要求1的方法，其中反应在分批反应器中进行。
9.权利要求1的方法，其中步骤(b)中进行蒸馏的温度为大约410°F，压力低于大气压，大约为35mmHg绝对压。
10.权利要求I的方法，其中在大约126-202°F通过液液提取实施步骤(c)。
11.权利要求1的方法，其中在步骤(a)中苯酚与酮的反应温度为大约175-200°F。
12.权利要求1的方法，其中来自融化结晶器的再循环残留物在大约273°F蒸馏以除去轻馏分，在大约372-390°F、大约4mmHg的压力下蒸馏以除去中间馏分。
13.权利要求1的方法，其中将来自步骤(i)的苯酚通过在310-510°F催化裂化进行回收。
14.权利要求1的方法，其中从融化结晶器中纯化的双酚在双酚回收装置中成为薄片。
15.权利要求1的方法，其中从融化结晶器中纯化的双酚在双酚回收装置中变为颗粒。
16.按照权利要求1制造的产物。
17.权利要求1的方法，它主要包括：
(a)在离子交换树脂催化剂的存在下将苯酚与酮反应，产生双酚；
(b)在苯酚排除装置中从步骤(a)产生的双酚中分离出未反应的苯酚；
(c)在母液干燥器装置中从所述分离的苯酚中提取水和丙酮，以获得干燥的苯酚，并将干燥的苯酚返回到所述的反应器中；
(d)在废水纯化装置中从步骤(c)提取的丙酮中分离出提取的水，并将所述的丙酮返回到所述反应器中，将所述水转移至水排出装置中；
(e)通过在降膜式动态结晶器中分步融化结晶，在融化结晶器中从在苯酚排除装置中获得的双酚中分离出苯酚、异构体和焦油；
(f)从所述融化结晶器中将包含双酚、苯酚、焦油和异构体的再循环残留物转移到再循环回收装置中；
(g)从再循环回收装置中回收双酚，并将回收的双酚返回到融化结晶器中；
(h)从所述再循环回收装置中将残留物苯酚、焦油和异构体转移到焦油/异构体回收装置中；
(i)从焦油/异构体裂化器中回收苯酚，其中将苯酚返回到反应器中并将焦油加以处理；
(j)在双酚回收装置中回收在融化结晶器中纯化的双酚。
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