CN103664560B - 一种制备α-异佛尔酮的方法 - Google Patents
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Abstract
本发明公开一种制备α-异佛尔酮的方法，包括丙酮在碱催化下缩合反应得到α-异佛尔酮，其特点在于，所述缩合反应是在水和二甲苯的混合溶剂体系中进行。本发明将丙酮在水和二甲苯的混合溶剂体系中进行缩合反应，反应达到一定时间后，α-异佛尔酮的选择性达到基本稳定，即使继续反应对α-异佛尔酮、异丙叉丙酮和异丙酮醇的选择性影响也非常小，不需像现有合成方法那样严格控制反应终点，适合工业生产。采用本发明方法丙酮转化率达25～55%，对α-异佛尔酮的选择性65～80%，异丙叉丙酮和异丙酮醇总选择性0.5～10%。
Description
技术领域
本发明涉及一种制备α-异佛尔酮的方法。
背景技术
α-异佛尔酮的用途十分广泛，它是塑料、粘合剂、医药、香料、环氧树脂固化剂、油漆涂料的原料。α-异佛尔酮的合成主要是采用液相缩合法，由丙酮用碱催化缩合得到，现有方法主要有以下几种：
1944年，S.A.Ballard报道采用20%NaOH做催化剂，于150℃反应3小时，丙酮转化率为17%，α-异佛尔酮选择性为39%，1946年，Ballard研究了不同催化剂浓度、反应时间和投料速度等条件对丙酮转化率和α-异佛尔酮选择性的影响，得到最优条件为170℃时丙酮在28%KOH水溶液下反应40min，原料转化率21.0%，α-异佛尔酮选择性达到47.7%。
1947年，Royal Dutch Shell公司的Fife报道了用25%NaOH为催化剂，与90%丙酮水溶液在170℃反应37分钟，丙酮转化率为13.6%，α-异佛尔酮选择性51%。
1955年，法国的S.I.D.A公司在专利中报道了用氢氧化钠的甲醇溶液合成α-异佛尔酮的方法，反应温度控制在180～215℃、连续加入浓度为50%氢氧化钠甲醇溶液，压力25～40bar，反应30分钟，丙酮转化率为39.7%，α-异佛尔酮选择性高达68%。
1968年，加拿大Shawinigan化学公司的Kohan研究了以碱金属氢氧化物为催化剂，不同反应时间、配比、催化剂浓度对反应结果的影响，在45%KOH水溶液催化下，220℃反应20分钟，丙酮转化率为39.6%时，α-异佛尔酮选择性为55.4%，
1989年，黄操胜报道了将丙酮、KOH、水在200～210℃反应1.5～2.0小时后降温，蒸馏，当丙酮转化率为50%时，α-异佛尔酮选择性为36～40%。
1999年，李平报道了将一定量的丙酮、水、催化剂于150～300℃、3.0～3.5MPa反应1.5～2.0小时，蒸出未反应丙酮，当丙酮转化率为30～40%时，α-异佛尔酮的选择性为60～70%，丙酮单程转化率为35%左右。
2000年，毛丽秋（湖南师范大学自然科学学报23（3），2000）采用0.7%KOH、75%丙酮水溶液于200℃、2.5MPa反应5小时，丙酮转化率为57.6%，α-异佛尔酮的选择性为70%。
上述反应的历程为：
。
然而，丙酮缩合为串联反应，随着反应时间会产生双分子缩合产物、三分子缩合产物和多分子缩合产物，α-异佛尔酮为丙酮的三分子缩合产物，采用上述各方法，因反应是在高温高压下进行，产物从反应体系及时分离出来是极为困难的，丙酮极易继续缩合生成多分子缩合产物，使得反应生成的α-异佛尔酮达到选择性峰值时间非常短暂，需及时泄压停止加热以终止反应，以避免大量多分子缩合产物产生，然而快速泄压容易喷料，缓慢泄压又造成时间过长，因此对反应终点的控制要求极严，且不易控制。
发明内容
本发明的目的是解决现有由丙酮缩合制备α-异佛尔酮时反应多步缩合使终点不易控制的缺点，提供一种反应易控制的制备α-异佛尔酮的方法。
本发明实现上述目的所采用的技术方案如下：
一种制备α-异佛尔酮的方法，包括丙酮在碱催化下缩合反应得到α-异佛尔酮，其特点在于，所述缩合反应是在水和二甲苯的混合溶剂体系中进行。
进一步，所述混合溶剂体系中水与二甲苯的质量比为1：（1～9），优选为1：（1.3～4.5）。
进一步，碱的用量为丙酮质量的0.75～2%。
进一步，所述碱为氢氧化钾或氢氧化铯。
进一步，所述缩合反应的温度为200～220℃，压力为20～51bar，反应2小时以上。
进一步，所述丙酮与水的质量比为（4.5～9）：1。
α-异佛尔酮的分离纯化：从反应液中分离出二甲苯相，二甲苯相常压精馏回收丙酮和二甲苯后，再减压精馏得到α-异佛尔酮。
有益效果：本发明将丙酮在水和二甲苯的混合溶剂体系中进行缩合反应，反应达到一定时间后，α-异佛尔酮的选择性达到基本稳定，即使继续反应对α-异佛尔酮、异丙叉丙酮和异丙酮醇的选择性影响也非常小，基本没有多分子聚合产物，反应更容易控制，不需像现有合成方法那样严格控制反应终点，本发明方法适合于工业生产。采用本发明方法丙酮转化率达25～55%，对α-异佛尔酮的选择性65～80%，异丙叉丙酮和异丙酮醇总选择性10%以下。
具体实施方式
以下结合实施例对本发明做进一步详细说明。
实施例1
将450g丙酮、100g去离子水、3.4090g KOH和135g二甲苯依次加入高压反应釜，搅拌条件下加热升温，从室温升到218℃，此时压力48bar，开始计时，反应2.0小时后，温度221℃，压力47.5bar，从反应釜取样口取样，用气相色谱分析，丙酮转化率39.7%，α-异佛尔酮选择性69.61%，异丙叉丙酮和异丙酮醇总选择性为1.49%，基本没有四分子聚合产物。反应液冷却后，分离水和二甲苯相，二甲苯相常压精馏回收丙酮和二甲苯，再减压精馏分离得α-异佛尔酮，减压精馏真空度0.087MPa，理论塔板数20块。
实施例2
将600g丙酮、133g去离子水、4.5460g KOH和180g二甲苯依次加入高压反应釜，搅拌条件下加热升温，从室温升到218℃，此时压力50bar，开始计时，反应2.0h，温度220℃，压力49bar，取样用气相色谱分析，丙酮转化率45.26%，α-异佛尔酮选择性72.05%，异丙叉丙酮和异丙酮醇总选择性1.00%，基本没有四分子聚合产物。
实施例3
将450g丙酮、100g去离子水、3.4090g KOH、135g丙酮依次加入高压反应釜，搅拌条件下加热升温，升温到217℃，压力48bar，开始计时，反应至2.0小时从反应釜取样口取样，用气相色谱分析，丙酮转化率39.70%，α-异佛尔酮选择性69.61%，异丙叉丙酮和异丙酮醇总选择性1.49%，反应至2.5小时，此时，温度221℃，压力47bar，从反应釜取样口取样，取样冷凝液用气相色谱仪分析，丙酮转化率47.31%，α-异佛尔酮选择性66.51%，异丙叉丙酮和异丙酮醇总选择性1.67%，基本没有四分子聚合产物。
实施例4
将450g丙酮、100g去离子水、3.4090g KOH、180g二甲苯依次加入高压反应釜，搅拌条件下加热升温，升温到218℃，压力47bar，开始计时，反应3.0小时，停止加热，取样，用气相色谱仪分析，丙酮转化率45.26%，α-异佛尔酮选择性70.78%，异丙叉丙酮和异丙酮醇总选择性3.03%，基本没有四分子聚合产物。
实施例5
将450g丙酮 100g去离子水 3.4090g KOH、225g二甲苯依次加入高压反应釜，搅拌条件下加热升温，升温到218℃，压力46bar，开始计时，反应至2.0小时取样，样品用气相色谱仪分析，丙酮转化率28.93%，α-异佛尔酮选择性75.87%，异丙叉丙酮和异丙酮醇总选择性3.38%，反应至4.0小时取样，样品用气相色谱仪分析，丙酮转化率49.08%，α-异佛尔酮选择性71.51%，异丙叉丙酮和异丙酮醇总选择性1.61%，反应至6.0小时停止加热，此时釜内温度220℃，压力46bar，取样，样品冷凝液用气相色谱仪分析，丙酮转化率53.90%，α-异佛尔酮选择性68.30%，异丙叉丙酮和异丙酮醇总选择性1.37%，基本没有四分子聚合产物。
实施例6
将450g丙酮 100g去离子水 3.4090g KOH、360g二甲苯依次加入高压反应釜，搅拌条件下加热升温，升温到218℃，压力44.5bar，开始计时，反应3.0小时取样，样品冷凝液用气相色谱仪分析，丙酮转化率25.12%，α-异佛尔酮选择性77.75%，异丙叉丙酮和异丙酮醇总选择性6.62%，反应4.0小时取样，样品冷凝液用气相色谱仪分析，丙酮转化率32.11%，α-异佛尔酮选择性73.05%，异丙叉丙酮和异丙酮醇总选择性6.67%，反应6.0小时停止加热，此时釜内温度220℃，压力44.5bar，取样，样品冷凝液用气相色谱仪分析，丙酮转化率42.18%，α-异佛尔酮选择性72.75%，异丙叉丙酮和异丙酮醇总选择性5.06%，基本没有四分子聚合产物。
实施例7
将450g丙酮、100g去离子水、3.4090g KOH、450g二甲苯加入高压反应釜，搅拌条件下加热升温，升温到218℃，压力44bar，开始计时，反应6.0小时取样，气相色谱分析，丙酮转化率33.10%，α-异佛尔酮选择性76.26%，异丙叉丙酮和异丙酮醇总选择性6.48%，基本没有四分子聚合产物。
实施例8
将450g丙酮 、50g去离子水、3.4090g KOH、450g二甲苯加入高压反应釜，搅拌条件下加热升温，升温到219℃，压力41bar，开始计时，反应6.0小时停止加热并取样，取样液用气相色谱分析，丙酮转化率40.24%，α-异佛尔酮选择性74.09%，异丙叉丙酮和异丙酮醇总选择性0.65%，基本没有四分子聚合产物。
实施例9
将120g丙酮 、13.3g去离子水、1.212g KOH、120g二甲苯加入450ml高压反应釜，搅拌条件下加热升温，升温到220℃，压力33ar，开始计时，反应6.0小时停止加热并取样，取样液用气相色谱分析，丙酮转化率45.3%，α-异佛尔酮选择性71.3%，异丙叉丙酮和异丙酮醇总选择性3.8%，基本没有四分子聚合产物。
实施例10
将40g丙酮 、4.44g去离子水、0.80g KOH、40g二甲苯加入高压反应釜，搅拌条件下加热升温，升温到200℃，压力23bar，开始计时，反应6.0小时停止加热并取样，取样液用气相色谱分析，丙酮转化率28.4%，α-异佛尔酮选择性72.2%，异丙叉丙酮和异丙酮醇总选择性10.00%，基本没有四分子聚合产物。
实施例11
将40g丙酮 、4.44g去离子水、0.45g CsOH、40g二甲苯加入高压反应釜，搅拌条件下加热升温，升温到220℃，压力30bar，开始计时，反应6.0小时停止加热并取样，取样液用气相色谱分析，丙酮转化率44.2%，α-异佛尔酮选择性70.8%，异丙叉丙酮和异丙酮醇总选择性3.4%，基本没有四分子聚合产物。
最后应说明的是：以上所述仅为本发明的优选实施例而已，并不用于限制本发明，尽管参照前述实施例对本发明进行了详细的说明，对于本领域的技术人员来说，其依然可以对前述各实施例所记载的技术方案进行修改，或者对其中部分技术特征进行等同替换。凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。
Claims (5)
1.一种制备α-异佛尔酮的方法，包括丙酮在碱催化下缩合反应得到α-异佛尔酮，其特征在于，所述缩合反应是在水和二甲苯的混合溶剂体系中进行；
所述缩合反应的温度为200～220℃，压力为20～51bar，反应2小时以上。
2.根据权利要求1所述制备α-异佛尔酮的方法，其特征在于，所述混合溶剂体系中水与二甲苯的质量比为1：（1～9）。
3.根据权利要求1所述制备α-异佛尔酮的方法，其特征在于，碱的用量为丙酮质量的0.75～2%。
4.根据权利要求1或3所述制备α-异佛尔酮的方法，其特征在于，所述碱为氢氧化钾或氢氧化铯。
5.根据权利要求1所述制备α-异佛尔酮的方法，其特征在于，所述丙酮与水的质量比为（4.5～9）：1。
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| US3337633A (en) * | 1960-12-31 | 1967-08-22 | Hibernia Chemie G M B H | Production of isophorone |
| JPH08245485A (ja) * | 1995-03-13 | 1996-09-24 | Daicel Chem Ind Ltd | イソホロンの製造方法 |
| JPH09157207A (ja) * | 1995-12-14 | 1997-06-17 | Mitsui Toatsu Chem Inc | イソホロンの製造方法 |
| CN101633610A (zh) * | 2009-08-13 | 2010-01-27 | 浙江大学 | 一种α-异佛尔酮的制备方法 |
| CN102976910A (zh) * | 2011-09-05 | 2013-03-20 | 张锦碧 | 一种丙酮合成异佛尔酮的环保简易制备方法 |
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| US3337633A (en) * | 1960-12-31 | 1967-08-22 | Hibernia Chemie G M B H | Production of isophorone |
| JPH08245485A (ja) * | 1995-03-13 | 1996-09-24 | Daicel Chem Ind Ltd | イソホロンの製造方法 |
| JPH09157207A (ja) * | 1995-12-14 | 1997-06-17 | Mitsui Toatsu Chem Inc | イソホロンの製造方法 |
| CN101633610A (zh) * | 2009-08-13 | 2010-01-27 | 浙江大学 | 一种α-异佛尔酮的制备方法 |
| CN102976910A (zh) * | 2011-09-05 | 2013-03-20 | 张锦碧 | 一种丙酮合成异佛尔酮的环保简易制备方法 |
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