不饱和醛及双环芳烃的选择性催化加氢研究
摘要
不饱和醛和双环芳烃的选择性加氢是有机合成重要的单元反应,本论文系统研究了羰基、碳碳双键和芳环选择性加氢的反应规律。
以3,4,5-三甲氧基苯甲醛(TMB)为模型底物,系统研究了骨架Ni催化芳香醛C=O键选择性脱羰基和加氢脱氧的反应规律。以骨架Ni为催化剂,在四氢呋喃溶剂中,在190℃、3.0MPa条件下反应4h,当TMB转化率达100%时,得到的是脱羰基产物1,2,3-三甲氧基苯,其选择性可达83.1%,且在反应过程中未检测到苯环加氢的产物；而以Mo改性骨架Ni为催化剂,在环己烷溶剂中,165℃、6.5MPa条件下反应90min,当TMB转化率达100%时,得到的是羰基加氢脱氧产物3,4,5-三甲氧基甲苯(TMT),其选择性达98.6%;XPS分析结果显示零价Ni活性中心对加氢脱羰基反应具有促进作用,Mo的加入可与零价Ni形成强烈的相互作用,从而抑制了脱羰基副反应。
以肉桂醛为模型底物,系统研究了C=O键和C=C键选择性加氢的反应规律。结果表明,在Co-B合金中添加Mo组分对催化C=O键的选择性加氢具有明显的促进作用。在120℃、1.0MPa条件下反应120min,当肉桂醛的转化率为98.8%时,肉桂醇的选择性可达86.3%；而采用K2CO3处理后的Pd/C催化剂,可显著提高对C=C键加氢的选择性。在40℃、0.5MPa条件下反应80min,当肉桂醛的转化率为95.0%时,苯丙醛的选择性达98.6%。
以4,4'-二氨基二苯基甲烷(MDA)和4,4'-二羟基二苯基丙烷(BPA)为模型底物,研究了双环芳烃立体选择性加氢的反应规律。采用胶体法制备的纳米Ru/C催化剂,在160℃、8.0MPa条件下,当MDA的转化率达100%时,产物4,4'-二氨基-二环己基甲烷(H12MDA)的选择性达99.2%,反-反异构体含量低于25%,且催化剂使用寿命长,连续循环30次,仍能维持原料100%转化；而纳米Ru/C催化BPA的选择性加氢,在110℃、6.0MPa条件下,当BPA的转化率达100%时,产物4,4’-二羟基二环己基丙烷(H12BPA)的选择性达98.4%。
The selective hydrogenation of unsaturated aldehydes and diaromatics is an important reaction for organic synthesis. In this thesis, the selective hydrogenation of C=O, C=C bond and benzene ring were systematicly investigated.
The selective hydrogenation of3,4,5-trimethoxybenzaldehyde (TMB) to3,4,5-trimethoxytoluene (TMT) was studied over skeletal nickel catalyst. The hydrogenation of TMB was investigated over skeletal Ni catalyst without any additives, and1,2,3-trimethoxybenzene was obtained via directly cleavaging C-C bond. Under190℃and3.0MPa, the selectivity of1,2,3-trimethoxybenzene was as high as83.1%and no by-products for the hydrogenation of aromatic ring were detected during the whole reaction process. In addition, under the optimized reaction condtions of165℃,6.5MPa, the selectivity of TMT was up to98.6%at100%conversion of TMB over Mo modified skeletal nickel catalyst. It is found that Mo as modified components play a key role in controlling the selectivity for the hydrodeoxygenation of C=O bond. XPS analysis demonstrated that the peak for metallic Ni disappeared after skeletal Ni catalyst was modified by Mo componetent. The possible reason for high selectivity of TMT was attributed to the effective inhibition for the side reaction of decarbonylation.
The selective hydrogenation of α,β-unsaturated aldehydes were investigated and cinnamaldehyde (CAL) was chosen as a model substrate for the study of reaction mechanism. Results showed that Co-Mo-B alloy catalyst exhibited good performance for the hydrogenation of C=O bond. Under the optimal reaction conditions, the selectivity of cinnamic alcohol was up to86.3%when the conversion of CAL was98.8%. On the other hand, K2CO3has played a significant role in improving the selectivity of hydrocinnamicaldehyde (HCAL) over Pd/C catalyst. Under the optimal reaction conditions, the selectivity of HCAL was as high as98.6%with95.0%conversion of CAL.
Supported nano-Ru catalyst was employed for the selective hydrogenation of MDA and BPA to corresponding aliphatic compounds. The selectivity of H12MDA can be as high as99.2%and trans-trans isomer was lower than25%under160℃,8.0MPa with100%conversion of MDA. The conversion of MDA can still reach100%even after recycling for thirty times. Similarly, the selectivity of H12BPA can be up to98.4%at110℃,6.0MPa with100%conversion of BPA.
以3,4,5-三甲氧基苯甲醛(TMB)为模型底物,系统研究了骨架Ni催化芳香醛C=O键选择性脱羰基和加氢脱氧的反应规律。以骨架Ni为催化剂,在四氢呋喃溶剂中,在190℃、3.0MPa条件下反应4h,当TMB转化率达100%时,得到的是脱羰基产物1,2,3-三甲氧基苯,其选择性可达83.1%,且在反应过程中未检测到苯环加氢的产物；而以Mo改性骨架Ni为催化剂,在环己烷溶剂中,165℃、6.5MPa条件下反应90min,当TMB转化率达100%时,得到的是羰基加氢脱氧产物3,4,5-三甲氧基甲苯(TMT),其选择性达98.6%;XPS分析结果显示零价Ni活性中心对加氢脱羰基反应具有促进作用,Mo的加入可与零价Ni形成强烈的相互作用,从而抑制了脱羰基副反应。
以肉桂醛为模型底物,系统研究了C=O键和C=C键选择性加氢的反应规律。结果表明,在Co-B合金中添加Mo组分对催化C=O键的选择性加氢具有明显的促进作用。在120℃、1.0MPa条件下反应120min,当肉桂醛的转化率为98.8%时,肉桂醇的选择性可达86.3%；而采用K2CO3处理后的Pd/C催化剂,可显著提高对C=C键加氢的选择性。在40℃、0.5MPa条件下反应80min,当肉桂醛的转化率为95.0%时,苯丙醛的选择性达98.6%。
以4,4'-二氨基二苯基甲烷(MDA)和4,4'-二羟基二苯基丙烷(BPA)为模型底物,研究了双环芳烃立体选择性加氢的反应规律。采用胶体法制备的纳米Ru/C催化剂,在160℃、8.0MPa条件下,当MDA的转化率达100%时,产物4,4'-二氨基-二环己基甲烷(H12MDA)的选择性达99.2%,反-反异构体含量低于25%,且催化剂使用寿命长,连续循环30次,仍能维持原料100%转化；而纳米Ru/C催化BPA的选择性加氢,在110℃、6.0MPa条件下,当BPA的转化率达100%时,产物4,4’-二羟基二环己基丙烷(H12BPA)的选择性达98.4%。
The selective hydrogenation of unsaturated aldehydes and diaromatics is an important reaction for organic synthesis. In this thesis, the selective hydrogenation of C=O, C=C bond and benzene ring were systematicly investigated.
The selective hydrogenation of3,4,5-trimethoxybenzaldehyde (TMB) to3,4,5-trimethoxytoluene (TMT) was studied over skeletal nickel catalyst. The hydrogenation of TMB was investigated over skeletal Ni catalyst without any additives, and1,2,3-trimethoxybenzene was obtained via directly cleavaging C-C bond. Under190℃and3.0MPa, the selectivity of1,2,3-trimethoxybenzene was as high as83.1%and no by-products for the hydrogenation of aromatic ring were detected during the whole reaction process. In addition, under the optimized reaction condtions of165℃,6.5MPa, the selectivity of TMT was up to98.6%at100%conversion of TMB over Mo modified skeletal nickel catalyst. It is found that Mo as modified components play a key role in controlling the selectivity for the hydrodeoxygenation of C=O bond. XPS analysis demonstrated that the peak for metallic Ni disappeared after skeletal Ni catalyst was modified by Mo componetent. The possible reason for high selectivity of TMT was attributed to the effective inhibition for the side reaction of decarbonylation.
The selective hydrogenation of α,β-unsaturated aldehydes were investigated and cinnamaldehyde (CAL) was chosen as a model substrate for the study of reaction mechanism. Results showed that Co-Mo-B alloy catalyst exhibited good performance for the hydrogenation of C=O bond. Under the optimal reaction conditions, the selectivity of cinnamic alcohol was up to86.3%when the conversion of CAL was98.8%. On the other hand, K2CO3has played a significant role in improving the selectivity of hydrocinnamicaldehyde (HCAL) over Pd/C catalyst. Under the optimal reaction conditions, the selectivity of HCAL was as high as98.6%with95.0%conversion of CAL.
Supported nano-Ru catalyst was employed for the selective hydrogenation of MDA and BPA to corresponding aliphatic compounds. The selectivity of H12MDA can be as high as99.2%and trans-trans isomer was lower than25%under160℃,8.0MPa with100%conversion of MDA. The conversion of MDA can still reach100%even after recycling for thirty times. Similarly, the selectivity of H12BPA can be up to98.4%at110℃,6.0MPa with100%conversion of BPA.
引文
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