空气间接催化氧化含硫化合物反应的研究
摘要
本文研究了二苯并噻吩(DBT)和二甲基亚砜(DMSO)两种含硫化合物的氧化反应。DBT及其衍生物是油品中常见的含硫化合物,通过将其氧化为极性较大的砜可以采取萃取的方式从油品中脱出,达到深度脱硫的目的,而分离得到的砜经过处理后是常用的化工中间体。本文分别采用油溶性氧化剂过氧化氢异丙苯和空气为氧化剂对DBT或DMSO进行氧化,将其分别氧化为二苯并噻吩砜和二甲基砜。
采用过氧化氢异丙苯(CHP)作为油溶性的氧化剂,在固定床反应器中进行DBT的氧化反应。对氧化反应的产物进行了核磁、质谱和红外光谱表征,证明DBT可以被CHP在固定床反应器中氧化为二苯并噻吩砜。采用M003／SiO2作为催化剂时,DBT的转化率可达82%。采用碱土金属氧化物MgO、CaO、SrO、BaO,用分步浸渍的方法对M003／SiO2催化剂进行改性,提高了催化剂的活性。结果表明,碱土金属氧化物CaO,BaO改性的催化剂催化的DBT氧化反应中,DBT的转化率有不同程度的提高,CaO的效果最好,DBT的转化率达到94%。
利用有机化合物的自氧化反应可生成相应的过氧化物的特点,分别在正辛烷、十氢萘和甲苯为溶剂的DBT溶液中通入空气,加入偶氮二异丁腈(AIBN)或过氧化苯甲酰(BPO)等容易生成自由基的物质加快有机化合物的自氧化速度,以Ti-MCM-41为催化剂,将DBT氧化为相应的砜。在十氢萘或正辛烷溶液中DBT的转化率达到100%；在甲苯溶液中DBT的转化率达到83%。这是由于不同的有机分子自氧化生成过氧化物的速度不同造成的。
本文还研究了空气氧化DMSO的反应。在异丙苯溶液中,70℃时,AIBN分解产生自由基,引发异丙苯在空气中的自氧化反应,生成过氧化氢异丙苯；生成的过氧化氢异丙苯在偏钒酸铵的催化作用下,将二甲亚砜氧化生成二甲砜。反应条件为：在20 mL异丙苯中加入3mL DMSO时,反应温度70℃,180 min,催化剂用量0.3 g,AIBN用量0.4 g,DMSO滴加,DMSO转化率可达94%。
The oxidation reaction of dibenzothiophene (DBT) and dimethyl sulfoxide(DMSO) were investigated in the paper. DBT and its derivatives are the common sulfur containing compounds in fuel, which are the most unreactive sulfur compounds during HDS and the major factor limiting deep desulfurization of HDS method. Through oxidation reaction, DBT is oxidized to the corresponding sulfone which has higher polarity than itself, so it can easily be removed by extraction from fuel and deep desulfurization was realized. Oil soluble oxidant cumene hydroperoxide (CHP) and air were used as oxidants for DBT, DMSO respectively. The oxidation products were DBT sulfone and dimethyl sulfone.
Catalytic oxidation of dibenzothiophene (DBT) in decalin was performed in a fixed bed glass reactor using an oil-soluble oxidant, cumene hydroperoxide (CHP), over MoO3/SiO2 catalyst. The conversion of DBT reached 82%. To improve the reactivity MoO3/SiO2 catalyst, alkaline earth metals, such as CaO, BaO, SrO and MgO were introduced to modify MoO3/SiO2 by a two step impregnation method. The results showed that the activity of CaO and BaO modified MoO3/SiO2 catalyst have higher activity than MoO3/SiO2 in the oxidation of DBT with CHP and the MoO3/Ca-SiO2 catalysts has best activity. The DBT conversion reached 94% at 60℃.
Based on the fact that hydrocarbon compounds can be autoxidized to corresponding hydroperoxide slowly by oxygen in air, the oxidations of DBT in decalin or n-octane toluene were respectively performed by the air/Ti-MCM-41 system in the presence of AIBN or BPO. The conversion of DBT can reach 100% when using decalin or n-octane as solvent; while the conversion of DBT can reach only 83% when using toluene as solvent at the same condition. This difference was result from the different auto oxidation speed of organic molecule.
Cumene was oxidized to corresponding hydroperoxide at 70℃in the presence of free radicals decomposed from AIBN. DMSO can be oxidized to dimethyl sulfone by the obtained hydroperoxide on ammonium metavanadate catalyst. The reaction condition were as follows: 3 mL DMSO was added to 20 mL cumene,70℃,180 min, dosage of catalyst 0.3 g, dosage of AIBN is 0.4 g, feeding mode of DMSO is dropping. The conversion of DMSO is 94%.
采用过氧化氢异丙苯(CHP)作为油溶性的氧化剂,在固定床反应器中进行DBT的氧化反应。对氧化反应的产物进行了核磁、质谱和红外光谱表征,证明DBT可以被CHP在固定床反应器中氧化为二苯并噻吩砜。采用M003／SiO2作为催化剂时,DBT的转化率可达82%。采用碱土金属氧化物MgO、CaO、SrO、BaO,用分步浸渍的方法对M003／SiO2催化剂进行改性,提高了催化剂的活性。结果表明,碱土金属氧化物CaO,BaO改性的催化剂催化的DBT氧化反应中,DBT的转化率有不同程度的提高,CaO的效果最好,DBT的转化率达到94%。
利用有机化合物的自氧化反应可生成相应的过氧化物的特点,分别在正辛烷、十氢萘和甲苯为溶剂的DBT溶液中通入空气,加入偶氮二异丁腈(AIBN)或过氧化苯甲酰(BPO)等容易生成自由基的物质加快有机化合物的自氧化速度,以Ti-MCM-41为催化剂,将DBT氧化为相应的砜。在十氢萘或正辛烷溶液中DBT的转化率达到100%；在甲苯溶液中DBT的转化率达到83%。这是由于不同的有机分子自氧化生成过氧化物的速度不同造成的。
本文还研究了空气氧化DMSO的反应。在异丙苯溶液中,70℃时,AIBN分解产生自由基,引发异丙苯在空气中的自氧化反应,生成过氧化氢异丙苯；生成的过氧化氢异丙苯在偏钒酸铵的催化作用下,将二甲亚砜氧化生成二甲砜。反应条件为：在20 mL异丙苯中加入3mL DMSO时,反应温度70℃,180 min,催化剂用量0.3 g,AIBN用量0.4 g,DMSO滴加,DMSO转化率可达94%。
The oxidation reaction of dibenzothiophene (DBT) and dimethyl sulfoxide(DMSO) were investigated in the paper. DBT and its derivatives are the common sulfur containing compounds in fuel, which are the most unreactive sulfur compounds during HDS and the major factor limiting deep desulfurization of HDS method. Through oxidation reaction, DBT is oxidized to the corresponding sulfone which has higher polarity than itself, so it can easily be removed by extraction from fuel and deep desulfurization was realized. Oil soluble oxidant cumene hydroperoxide (CHP) and air were used as oxidants for DBT, DMSO respectively. The oxidation products were DBT sulfone and dimethyl sulfone.
Catalytic oxidation of dibenzothiophene (DBT) in decalin was performed in a fixed bed glass reactor using an oil-soluble oxidant, cumene hydroperoxide (CHP), over MoO3/SiO2 catalyst. The conversion of DBT reached 82%. To improve the reactivity MoO3/SiO2 catalyst, alkaline earth metals, such as CaO, BaO, SrO and MgO were introduced to modify MoO3/SiO2 by a two step impregnation method. The results showed that the activity of CaO and BaO modified MoO3/SiO2 catalyst have higher activity than MoO3/SiO2 in the oxidation of DBT with CHP and the MoO3/Ca-SiO2 catalysts has best activity. The DBT conversion reached 94% at 60℃.
Based on the fact that hydrocarbon compounds can be autoxidized to corresponding hydroperoxide slowly by oxygen in air, the oxidations of DBT in decalin or n-octane toluene were respectively performed by the air/Ti-MCM-41 system in the presence of AIBN or BPO. The conversion of DBT can reach 100% when using decalin or n-octane as solvent; while the conversion of DBT can reach only 83% when using toluene as solvent at the same condition. This difference was result from the different auto oxidation speed of organic molecule.
Cumene was oxidized to corresponding hydroperoxide at 70℃in the presence of free radicals decomposed from AIBN. DMSO can be oxidized to dimethyl sulfone by the obtained hydroperoxide on ammonium metavanadate catalyst. The reaction condition were as follows: 3 mL DMSO was added to 20 mL cumene,70℃,180 min, dosage of catalyst 0.3 g, dosage of AIBN is 0.4 g, feeding mode of DMSO is dropping. The conversion of DMSO is 94%.
引文
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