脉冲电场对醇酸常温酯化反应影响研究
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摘要
本文系统研究了脉冲电场（Pulsed electric field，以下简称PEF)处理对常温醇酸酯化反应影响，对比分析了羧酸碳链长短不同、反应体系有水和无水以及反应过程有无催化剂存在时PEF处理对酯化反应影响的区别，并从不同角度探讨了PEF促进酯化反应的机理。主要研究工作及成果如下：
1.研究了脉冲电场处理对乙醇和乙酸无水体系酯化反应影响。结果表明在各种不同的反应条件下，脉冲电场均能促进乙醇和乙酸酯化反应进行。改变电场强度，发现酯化反应速率随着PEF场强的增加而增大；改变反应温度，现低温下PEF对酯化反应的促进作用更为明显；改变反应物醇酸摩尔比（1～5），发现酯化反应速率随着醇酸摩尔比的增加而增大，但醇酸摩尔比在3～5之间时，酯化反应速率的增长幅度减小。当PEF场强为6.6、13.3和20.0kV/cm时，反应活化能由76.64kJ/mol分别降至71.50、67.50和59.10kJ/mol，场强越强，活化能降低值就越大。
2.研究了脉冲电场处理对乙醇和丙酸无水体系酯化反应影响。结果表明在各种不同的反应条件下，脉冲电场均能促进乙醇和丙酸酯化反应进行。场强小于13.3kV/cm时，酯化反应速率随着PEF场强的增加而增大，其中场强为13.3kV/cm时，酯化反应速率已接近最大值，继续增大场强，酯化反应速率变化不大；同时发现低温下PEF对酯化反应的促进作用更为明显；当PEF场强为6.6、13.3和20.0kV/cm时，活化能由77.05kJ/mol分别降至72.60、62.85和62.49kJ/mol。场强13.3kV/cm时，活化能降低值已接近最大；场强在13.3～20.0kV/cm时，活化能降低值变化很小。
3.研究了脉冲电场协同硫酸氢钠催化乙醇和乙酸酯化反应。研究结果表明脉冲电场和催化剂协同作用促进了酯化反应，且促进效果大于两者单独作用时效果的总和。实验条件下场强为20.0kV/cm时，活化能由48.50kJ/mol降低到47.80kJ/mol。
4.通过对PEF处理过程能量分析，以及处理前后样品的红外光谱和核磁共振分析，对脉冲电场促进无水体系酯化反应机理作了初步探讨。结果表明PEF强化醇酸无水体系酯化反应机理是通过影响反应体系氢键和进一步极化极性基团，加速了四面体活化络合物的形成，降低了酯化反应活化能而达到提高酯化反应速率的目的。
通过对比分析PEF对无水体系酯化反应活化能影响，可知PEF对乙醇和乙酸物系、乙醇和丙酸物系活化能影响不同的原因是：丙酸和乙酸碳链结构不同，导致PEF对两组物系氢键的影响程度不同。PEF对含催化剂体系酯化反应促进效果最大，但对其活化能影响最小，说明PEF提高催化剂体系酯化反应速率的主要原因不是降低了活化能，而是在较低活化能体系中，PEF处理对分子微观结构的影响大大增加了分子间碰撞机率，提高了酯化反应速率。
5.研究了脉冲电场处理对醇酸含水体系中酯化反应影响。结果表明脉冲电场对含水体系中酯化反应的促进效果大于对无水体系，场强越强促进效果越明显；改变含水体系中醇酸摩尔比，发现PEF对乙酸浓度较高的样品促进效果较为显著；实验条件下场强为20.0kV/cm时，含水体系活化能由52.20kJ/mol显著降低到42.00kJ/mol。
6.通过PEF对乙酸水溶液微观结构影响的实质，推导出脉冲电场对醇酸含水体系酯化反应影响机理。主要包括两个方面，一方面是脉冲电场促进了弱电解质乙酸电离出更多的H＋，加快了酯化反应过程中四面体活性中间体的形成，降低了酯化反应活化能，反应速率增大；另一方面是脉冲电场破坏了体系中水化离子、水化分子结构，更多游离的离子、分子暴露在外面，增加了反应物分子间的碰撞机率，因此反应速率增加。对比PEF处理下各体系反应速率和活化能关系。结果表明，脉冲电场处理下活化能较低体系的酯化反应速率提高更多。
The effects of pulsed electric fields on alcohol-acid esterification under roomtemperature were systematically studied in this paper. Three analysis have been done thatanalyzed the effects of PEF on esterification in the watery system compared to the waterlesssystem, analyzed the effects of PEF on esterification with catalyst compared to esterificationwithout catalyst and analyzed the effects of PEF on esterification about short carbon chaincarboxylic acid compared to long carbon chain. The mechanism of esterification via pulsedelectric field application was explored from various angles. The main conclusions obtainedwere introduced as follows:
1. The effects of pulsed electric fields on ethanol-acetic acid system esterification werestudied. The results indicate that PEF could promote the esterification under differentreaction conditions. The reaction rate significantly increased with increasing the PEFintensity. At the same time, it also could be found that the effect of PEF on esterification wasmore significant at lower than at higher temperatures. when the molar ratio of ethanol toacetic acid was lower than5:1, the reaction rate increased with the molar ratio of ethanol toacetic acid. But when the molar ratio was changed from3:1to5:1, the growth of the reactionrate became slower. If the PEF intensity used is0,6.6,13.3, and20.0kV/cm, the meanactivation energy (Ea) for esterification is76.64,71.50,67.50and59.10kJ/mol, respectively.The relationship between the applied PEF strength (E) and the activation energy decrease(ΔEa) can be that the reduced value of the activation energy was increased with the rising ofthe electric field strength.
2. The effects of pulsed electric fields on ethanol-propionic acid system esterificationwere studied. The results indicate that PEF could promote the esterification under differentreaction conditions. when the PEF intensity was lower than13.3kV/cm, the reaction rateincreased with increasing the PEF intensity, and the reaction rate was an optimal value as thePEF intensity was13.3kV/cm. When PEF intensity continue to increase, the reaction ratealmost did not increased with increasing the PEF intensity. At the same time, it also could befound that the effect of PEF on esterification was more significant at lower than at highertemperatures. If the PEF intensity used is0,6.6,13.3, and20.0kV/cm, the mean activationenergy (Ea) for esterification is77.05,72.60,62.85and62.49kJ/mol, respectively. Thereduced value of the activation energy was not linear with the increase of the electric fieldstrength, and the reduced value was an optimal value as the PEF intensity was13.3kV/cm.when the PEF intensity was lower than13.3kV/cm, The relationship between the applied PEF strength (E) and the activation energy decrease (ΔEa) can be that the reduced value of theactivation energywas increased with the rising of the electric field strength. when the PEFintensity was higher than13.3kV/cm, The relationship between the applied PEF strength (E)and the activation energy decrease (ΔEa) should be expressed in a nearly horizontal straightline.
3. The effects of pulsed electric fields-sodium bisulfate catalyst on ethanol-acetic acidsystem esterification were studied. The results indicated that the esterification was promotedby PEF-sodium bisulfate catalyst, and the synergy effect was greater than the sum of thesingle effect. If the PEF intensity used was20.0kV/cm, the mean activation energy (Ea) foresterification was decreased from48.50kJ/mol to47.80kJ/mol.
4. The mechanism of PEF treatment on esterification in waterless system was exploredusing the energy analysis, FTIR and1HNMR technology. The results indicated that Themechanism of PEF on esterification in waterless system was breaking hydrogen bonds andpolarizing polar group. It lead to the fast formation of reactive intermediates and theactivation energy decreasing, and the reaction rate increased.
The effects of PEF on the activation energy in three waterless systems were compared.The effect of PEF on esterification of ethanol-propionic acid was different from PEF onethanol-acetic acid. The reason was that the different carbon chain structure between the twoled to the different effect of PEF on the hydrogen bonds in the two systems. The effect of PEFon esterification with catalyst was strongest, but the effect of PEF on the activation energywas smallest. It showed that the mainly reason of the reaction rate increasing via PEF wasnot decrease of activity energy. It should be that in the system with lower activation energy,the effect of PEF on molecule structure led to the more collision probabilities. So, the reactionrate increased.
5. The effects of pulsed electric fields on ethanol-acetic acid watery systemesterification were studied. The results indicated that the effects of PEF on the water systemwas greater than on the waterless system, and the effects of PEF on the water systemincreased with increasing PEF intensity. When the molar ratio of ethanol to acetic acid inwatery system was changed, the reaction rate increased with the higher acetic acidconcentration. If the PEF intensity used was20.0kV/cm, the mean activation energy (Ea) foresterification was decreased from52.20kJ/mol to42.00kJ/mol.
6. The mechanism of PEF treatment on esterification in watery system was exploredusing the essence of acetic acid watery system via PEF application. There were mainly tworeasons: First, PEF treatment improve ionization levels of acetic acid to forms more H＋. The presence of H＋lead to the fast formation of reactive intermediates and the activation energydecreasing, and the reaction rate increased. Second, PEF treatment destroyed hydrated ions ormolecules to form more bare ion or molecule. Reaction molecules could meet very often, sothe reaction rate increased. The relationship between reaction rate and activation energy invarious system was compared via PEF application. The result showed that tthe reaction rateincreased more in the higher activation energy system under PEF treatment.
1.研究了脉冲电场处理对乙醇和乙酸无水体系酯化反应影响。结果表明在各种不同的反应条件下，脉冲电场均能促进乙醇和乙酸酯化反应进行。改变电场强度，发现酯化反应速率随着PEF场强的增加而增大；改变反应温度，现低温下PEF对酯化反应的促进作用更为明显；改变反应物醇酸摩尔比（1～5），发现酯化反应速率随着醇酸摩尔比的增加而增大，但醇酸摩尔比在3～5之间时，酯化反应速率的增长幅度减小。当PEF场强为6.6、13.3和20.0kV/cm时，反应活化能由76.64kJ/mol分别降至71.50、67.50和59.10kJ/mol，场强越强，活化能降低值就越大。
2.研究了脉冲电场处理对乙醇和丙酸无水体系酯化反应影响。结果表明在各种不同的反应条件下，脉冲电场均能促进乙醇和丙酸酯化反应进行。场强小于13.3kV/cm时，酯化反应速率随着PEF场强的增加而增大，其中场强为13.3kV/cm时，酯化反应速率已接近最大值，继续增大场强，酯化反应速率变化不大；同时发现低温下PEF对酯化反应的促进作用更为明显；当PEF场强为6.6、13.3和20.0kV/cm时，活化能由77.05kJ/mol分别降至72.60、62.85和62.49kJ/mol。场强13.3kV/cm时，活化能降低值已接近最大；场强在13.3～20.0kV/cm时，活化能降低值变化很小。
3.研究了脉冲电场协同硫酸氢钠催化乙醇和乙酸酯化反应。研究结果表明脉冲电场和催化剂协同作用促进了酯化反应，且促进效果大于两者单独作用时效果的总和。实验条件下场强为20.0kV/cm时，活化能由48.50kJ/mol降低到47.80kJ/mol。
4.通过对PEF处理过程能量分析，以及处理前后样品的红外光谱和核磁共振分析，对脉冲电场促进无水体系酯化反应机理作了初步探讨。结果表明PEF强化醇酸无水体系酯化反应机理是通过影响反应体系氢键和进一步极化极性基团，加速了四面体活化络合物的形成，降低了酯化反应活化能而达到提高酯化反应速率的目的。
通过对比分析PEF对无水体系酯化反应活化能影响，可知PEF对乙醇和乙酸物系、乙醇和丙酸物系活化能影响不同的原因是：丙酸和乙酸碳链结构不同，导致PEF对两组物系氢键的影响程度不同。PEF对含催化剂体系酯化反应促进效果最大，但对其活化能影响最小，说明PEF提高催化剂体系酯化反应速率的主要原因不是降低了活化能，而是在较低活化能体系中，PEF处理对分子微观结构的影响大大增加了分子间碰撞机率，提高了酯化反应速率。
5.研究了脉冲电场处理对醇酸含水体系中酯化反应影响。结果表明脉冲电场对含水体系中酯化反应的促进效果大于对无水体系，场强越强促进效果越明显；改变含水体系中醇酸摩尔比，发现PEF对乙酸浓度较高的样品促进效果较为显著；实验条件下场强为20.0kV/cm时，含水体系活化能由52.20kJ/mol显著降低到42.00kJ/mol。
6.通过PEF对乙酸水溶液微观结构影响的实质，推导出脉冲电场对醇酸含水体系酯化反应影响机理。主要包括两个方面，一方面是脉冲电场促进了弱电解质乙酸电离出更多的H＋，加快了酯化反应过程中四面体活性中间体的形成，降低了酯化反应活化能，反应速率增大；另一方面是脉冲电场破坏了体系中水化离子、水化分子结构，更多游离的离子、分子暴露在外面，增加了反应物分子间的碰撞机率，因此反应速率增加。对比PEF处理下各体系反应速率和活化能关系。结果表明，脉冲电场处理下活化能较低体系的酯化反应速率提高更多。
The effects of pulsed electric fields on alcohol-acid esterification under roomtemperature were systematically studied in this paper. Three analysis have been done thatanalyzed the effects of PEF on esterification in the watery system compared to the waterlesssystem, analyzed the effects of PEF on esterification with catalyst compared to esterificationwithout catalyst and analyzed the effects of PEF on esterification about short carbon chaincarboxylic acid compared to long carbon chain. The mechanism of esterification via pulsedelectric field application was explored from various angles. The main conclusions obtainedwere introduced as follows:
1. The effects of pulsed electric fields on ethanol-acetic acid system esterification werestudied. The results indicate that PEF could promote the esterification under differentreaction conditions. The reaction rate significantly increased with increasing the PEFintensity. At the same time, it also could be found that the effect of PEF on esterification wasmore significant at lower than at higher temperatures. when the molar ratio of ethanol toacetic acid was lower than5:1, the reaction rate increased with the molar ratio of ethanol toacetic acid. But when the molar ratio was changed from3:1to5:1, the growth of the reactionrate became slower. If the PEF intensity used is0,6.6,13.3, and20.0kV/cm, the meanactivation energy (Ea) for esterification is76.64,71.50,67.50and59.10kJ/mol, respectively.The relationship between the applied PEF strength (E) and the activation energy decrease(ΔEa) can be that the reduced value of the activation energy was increased with the rising ofthe electric field strength.
2. The effects of pulsed electric fields on ethanol-propionic acid system esterificationwere studied. The results indicate that PEF could promote the esterification under differentreaction conditions. when the PEF intensity was lower than13.3kV/cm, the reaction rateincreased with increasing the PEF intensity, and the reaction rate was an optimal value as thePEF intensity was13.3kV/cm. When PEF intensity continue to increase, the reaction ratealmost did not increased with increasing the PEF intensity. At the same time, it also could befound that the effect of PEF on esterification was more significant at lower than at highertemperatures. If the PEF intensity used is0,6.6,13.3, and20.0kV/cm, the mean activationenergy (Ea) for esterification is77.05,72.60,62.85and62.49kJ/mol, respectively. Thereduced value of the activation energy was not linear with the increase of the electric fieldstrength, and the reduced value was an optimal value as the PEF intensity was13.3kV/cm.when the PEF intensity was lower than13.3kV/cm, The relationship between the applied PEF strength (E) and the activation energy decrease (ΔEa) can be that the reduced value of theactivation energywas increased with the rising of the electric field strength. when the PEFintensity was higher than13.3kV/cm, The relationship between the applied PEF strength (E)and the activation energy decrease (ΔEa) should be expressed in a nearly horizontal straightline.
3. The effects of pulsed electric fields-sodium bisulfate catalyst on ethanol-acetic acidsystem esterification were studied. The results indicated that the esterification was promotedby PEF-sodium bisulfate catalyst, and the synergy effect was greater than the sum of thesingle effect. If the PEF intensity used was20.0kV/cm, the mean activation energy (Ea) foresterification was decreased from48.50kJ/mol to47.80kJ/mol.
4. The mechanism of PEF treatment on esterification in waterless system was exploredusing the energy analysis, FTIR and1HNMR technology. The results indicated that Themechanism of PEF on esterification in waterless system was breaking hydrogen bonds andpolarizing polar group. It lead to the fast formation of reactive intermediates and theactivation energy decreasing, and the reaction rate increased.
The effects of PEF on the activation energy in three waterless systems were compared.The effect of PEF on esterification of ethanol-propionic acid was different from PEF onethanol-acetic acid. The reason was that the different carbon chain structure between the twoled to the different effect of PEF on the hydrogen bonds in the two systems. The effect of PEFon esterification with catalyst was strongest, but the effect of PEF on the activation energywas smallest. It showed that the mainly reason of the reaction rate increasing via PEF wasnot decrease of activity energy. It should be that in the system with lower activation energy,the effect of PEF on molecule structure led to the more collision probabilities. So, the reactionrate increased.
5. The effects of pulsed electric fields on ethanol-acetic acid watery systemesterification were studied. The results indicated that the effects of PEF on the water systemwas greater than on the waterless system, and the effects of PEF on the water systemincreased with increasing PEF intensity. When the molar ratio of ethanol to acetic acid inwatery system was changed, the reaction rate increased with the higher acetic acidconcentration. If the PEF intensity used was20.0kV/cm, the mean activation energy (Ea) foresterification was decreased from52.20kJ/mol to42.00kJ/mol.
6. The mechanism of PEF treatment on esterification in watery system was exploredusing the essence of acetic acid watery system via PEF application. There were mainly tworeasons: First, PEF treatment improve ionization levels of acetic acid to forms more H＋. The presence of H＋lead to the fast formation of reactive intermediates and the activation energydecreasing, and the reaction rate increased. Second, PEF treatment destroyed hydrated ions ormolecules to form more bare ion or molecule. Reaction molecules could meet very often, sothe reaction rate increased. The relationship between reaction rate and activation energy invarious system was compared via PEF application. The result showed that tthe reaction rateincreased more in the higher activation energy system under PEF treatment.
引文
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