典型多环芳烃的加氢反应研究进展
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摘要
提高供氢溶剂的供氢能力是煤直接液化技术开发的重点之一,而多环芳烃加氢之后获得的氢化芳烃是煤直接液化的有效供氢溶剂组分。调控加氢深度是提高供氢性能的有效措施。文章介绍了多环芳烃萘、蒽和菲的加氢路径,并介绍了工艺条件和催化剂种类对其加氢产物选择性的影响。芳烃的环数越多,其加氢程度越难;使用CoMo类、NiCl过渡金属类等催化剂和调控加氢条件均有利于生成加氢中间产物,但目前二、三环氢化芳烃的工艺条件开发尚不成熟。此外芳烃加氢反应基本为一级反应,且首环加氢速率最快;加氢平衡常数随温度的升高而降低。将热力学、动力学和分子模拟结合,可实现生产高效氢化芳烃的目的。
Improving donor-hydrogen capacity of recycle solvent has been one important aspect of the direct coal liquefaction( DCL) process,and hydrogenated polycyclic aromatics are the main effective compositions of recycle solvent.In hence,selective hydrogenation of polycyclic aromatic hydrocarbons is the effective measure to promote the donor-hydrogen capacity. This paper detailed the hydrogenation routes of polycyclic aromatics. And the effect of catalysts and reaction conditions on hydrogenated products was also summarized. The more ring in aromatics,the more difficult it is to hydrogenate. It is beneficial to produce the hydrogenation intermediate with Co Mo,NiCl catalysts and optimizing the process conditions. However,the process of hydrogenated polycyclic aromatics is still being developed. Besides, the hydrogenation process is the first-order reaction and the hydrogenate rate of the first ring is the fastest. The hydrogenation equilibrium constantly decreases with the rise of temperature. By combining thermodynamics, kinetics and molecular simulation,it is feasible to generate highly efficient hydrogenated aromatic hydrocarbons.
Improving donor-hydrogen capacity of recycle solvent has been one important aspect of the direct coal liquefaction( DCL) process,and hydrogenated polycyclic aromatics are the main effective compositions of recycle solvent.In hence,selective hydrogenation of polycyclic aromatic hydrocarbons is the effective measure to promote the donor-hydrogen capacity. This paper detailed the hydrogenation routes of polycyclic aromatics. And the effect of catalysts and reaction conditions on hydrogenated products was also summarized. The more ring in aromatics,the more difficult it is to hydrogenate. It is beneficial to produce the hydrogenation intermediate with Co Mo,NiCl catalysts and optimizing the process conditions. However,the process of hydrogenated polycyclic aromatics is still being developed. Besides, the hydrogenation process is the first-order reaction and the hydrogenate rate of the first ring is the fastest. The hydrogenation equilibrium constantly decreases with the rise of temperature. By combining thermodynamics, kinetics and molecular simulation,it is feasible to generate highly efficient hydrogenated aromatic hydrocarbons.
引文
[1]李克健,舒歌平,史士东.煤炭液化技术[M].北京:煤炭工业出版社,2003.
[2]任相坤,房鼎业,金嘉璐,等.煤直接液化技术开发新进展[J].化工进展,2010(2):198-204.
[3]黄风林,郭亚冰,范峥,等.催化裂化(FCC)油浆作煤直接液化溶剂的研究进展[J].化工进展,2014(4):866-872.
[4] Nuzzi M,Marcandalli B. Hydrogenation of phenanthrene in the presence of Ni catalyst. Thermal dehydrogenation of hydrophenanthrenes and role of individual species in hydrogen transfers for coal liquefaction[J]. Fuel Processing Technology,2003,80(1):35-45.
[5] Styliani C. Korre M N M T. Hydrogenation of polynuclear aromatic hydrocarbons. 2. quantitative structure/reactivity correlations[J]. Chemical Engineering Science, 1994, 49(24):4191-4210.
[6]刘成运.多环芳烃的选择性催化加氢研究[D].大连:大连理工大学,2013.
[7]郑修新,赵甲,孙国方,等.萘加氢催化剂的研究进展[J].化工进展,2015(5):1295-1299.
[8]蔺华林,张德祥,彭俊,等.神华煤直接液化循环油的分析表征[J].燃料化学学报,2007(1):104-108.
[9]宋盘龙,卞俊杰,孟祥春,等.改性MCM-41沸石负载的Pd-Pt催化剂上萘的加氢活性及耐硫性研究[J].石油学报(石油加工),2004(6):40-45.
[10] Styliani C. Korre M T K A. Polynuclear Aromatic Hydrocarbons Hydrogenation. 1. Experimental Reaction Pathways and Kinetics[J]. Industrial&Engineering Chemistry Research,1995,34(1):101-117.
[11] Schoichi K,Masakatsu N,Hiroyuki S,et al. Hydrocracking of coal using molten salts as catalysts[J]. Energy Developments in Japan,1981,4(2):183-200.
[12]何国锋,关北峰,王燕芳,等.低温热解焦油中油馏分加氢脱氮和芳烃加氢宏观动力学的研究[J].煤炭转化,1998(1):54-58.
[13] Beltramone A R,Resasco D E,Alvarez W E,et al. Simultaneous Hydrogenation of Multiring Aromatic Compounds over Ni Mo Catalyst[J]. Industrial&Engineering Chemistry Research,2008,47(19):7161-7166.
[14]朱红英,张晔,邱泽刚,等.反应条件对萘饱和加氢的影响[J].精细化工,2009(5):512-516.
[15]张小菲.萘_甲基萘在Ni2P/Si O2及Pd-Pt/SiO2-Al2O3催化剂上的加氢研究[D].大连:大连理工大学,2011.
[16] Xiao Chen Y M L W. Nickel-Aluminum Intermetallic Compounds as Highly Selective and Stable Catalysts for the Hydrogenation of Naphthalene to Tetralin[J]. Chem Cat Chem. 2015, 6(7):978-983.
[17] Qian W,Yoda Y,Hirai Y,et al. Hydrodesulfurization of dibenzothiophene and hydrogenation of phenanthrene on aluminasupported Pt and Pd catalysts[J]. Applied Catalysis A:General,1999,184(1):81-88.
[18] Durland J R A H. Hydrogenation of phenanthrene[J]. Journal of the American Chemical Society,1937(59):135-136.
[19]李会峰,刘锋,刘泽龙,等.菲在不同加氢催化剂上的转化[J].石油学报(石油加工),2011(1):20-25.
[20] Cameron J M L,Cook J W,Graham W. Catalytic hydrogenation of pyrene[J]. Journal of Chemical Society,1945:286-288.
[21] Jr. Garlock E A,Mosettig E. Studies in the Anthracene Series.I. Methyl Ketones and Carbinolamines Derived from 1,2,3,4-Tetrahydroanthracene[J]. Journal of the american chemical society,1945,67(12):2255-2259.
[22] Alonso F,Yus M. Catalytic Hydrogenation of Organic Compounds using the Ni Cl2-Li-Naphthalene(cat.)Combination[J].Advanced synthesis&catalysis,2001,2(343):188-191.
[23]杨惠斌,王雅纯,江洪波,等. Ni Mo/Al2O3催化剂上菲加氢反应体系动力学[J].化学反应工程与工艺,2014(6):550-556.
[24]周凌,赵静,张德祥.三环芳烃菲在浆态床内的催化加氢转化及动力学研究[J].石油化工,2015(6):705-711.
[25]张小菲,邵正锋,毛国强,等.萘在贵金属Pd、Pt及PdPt催化剂上的加氢活性及耐硫性能[J].物理化学学报,2010(10):2691-2698.
[26] Dufesne P B P H B. New development in hydrocracking:Low pressure high-conversion hydrocracking[J]. Catalysis Today,1987(1):367-384.
[27] Bouchy M P S D P. Hydrogenation and hydrocracking of a model light cycle oil feed. 2. Properties of a sulfides nickelmolybdenum hydrocracking catalyst[J]. Industrial and Engineering Chemistry Research,1993(32):1592-1602.
[28] Barry H. Cooper B B L D. Aromatic saturation of distillates:an overview[J]. Applied Catalysis A:General, 1996(137):203-223.
[29]侯朝鹏,李永丹,夏国富,等.蒽和菲加氢反应热力学分析[J].石油化工,2013(7):761-766.
[30]杨惠斌.菲加氢反应体系的研究[D].上海:华东理工大学,2015.
[31] Dutta R P,Schobert H H. Hydrogenation/dehydrogenation of polycyclic aromatic hydrocarbons using ammonium tetrathiomolybdate as catalyst precursor[J]. Catalysis Today,1996,31(1-2):65-77.
[32]杨惠斌,常小瑞,江洪波,等.菲加氢反应体系的热力学计算和分析[J].化学反应工程与工艺,2012(6):499-505.
[33]王春璐,周涵,王子军,等.稠环芳烃直接加氢的分子模拟研究[J].计算机与应用化学, 2012(10):1221-1224.
[34]王春璐,周涵,王子军,等.菲分子不同碳原子位置加氢初始反应的量子化学[J].石油学报(石油加工),2012(4):642-645.
[35]江夏,宗士猛,李秀生,等.烃分子供氢能力的分子模拟[J].石油学报(石油加工),2012(2):254-259.
[2]任相坤,房鼎业,金嘉璐,等.煤直接液化技术开发新进展[J].化工进展,2010(2):198-204.
[3]黄风林,郭亚冰,范峥,等.催化裂化(FCC)油浆作煤直接液化溶剂的研究进展[J].化工进展,2014(4):866-872.
[4] Nuzzi M,Marcandalli B. Hydrogenation of phenanthrene in the presence of Ni catalyst. Thermal dehydrogenation of hydrophenanthrenes and role of individual species in hydrogen transfers for coal liquefaction[J]. Fuel Processing Technology,2003,80(1):35-45.
[5] Styliani C. Korre M N M T. Hydrogenation of polynuclear aromatic hydrocarbons. 2. quantitative structure/reactivity correlations[J]. Chemical Engineering Science, 1994, 49(24):4191-4210.
[6]刘成运.多环芳烃的选择性催化加氢研究[D].大连:大连理工大学,2013.
[7]郑修新,赵甲,孙国方,等.萘加氢催化剂的研究进展[J].化工进展,2015(5):1295-1299.
[8]蔺华林,张德祥,彭俊,等.神华煤直接液化循环油的分析表征[J].燃料化学学报,2007(1):104-108.
[9]宋盘龙,卞俊杰,孟祥春,等.改性MCM-41沸石负载的Pd-Pt催化剂上萘的加氢活性及耐硫性研究[J].石油学报(石油加工),2004(6):40-45.
[10] Styliani C. Korre M T K A. Polynuclear Aromatic Hydrocarbons Hydrogenation. 1. Experimental Reaction Pathways and Kinetics[J]. Industrial&Engineering Chemistry Research,1995,34(1):101-117.
[11] Schoichi K,Masakatsu N,Hiroyuki S,et al. Hydrocracking of coal using molten salts as catalysts[J]. Energy Developments in Japan,1981,4(2):183-200.
[12]何国锋,关北峰,王燕芳,等.低温热解焦油中油馏分加氢脱氮和芳烃加氢宏观动力学的研究[J].煤炭转化,1998(1):54-58.
[13] Beltramone A R,Resasco D E,Alvarez W E,et al. Simultaneous Hydrogenation of Multiring Aromatic Compounds over Ni Mo Catalyst[J]. Industrial&Engineering Chemistry Research,2008,47(19):7161-7166.
[14]朱红英,张晔,邱泽刚,等.反应条件对萘饱和加氢的影响[J].精细化工,2009(5):512-516.
[15]张小菲.萘_甲基萘在Ni2P/Si O2及Pd-Pt/SiO2-Al2O3催化剂上的加氢研究[D].大连:大连理工大学,2011.
[16] Xiao Chen Y M L W. Nickel-Aluminum Intermetallic Compounds as Highly Selective and Stable Catalysts for the Hydrogenation of Naphthalene to Tetralin[J]. Chem Cat Chem. 2015, 6(7):978-983.
[17] Qian W,Yoda Y,Hirai Y,et al. Hydrodesulfurization of dibenzothiophene and hydrogenation of phenanthrene on aluminasupported Pt and Pd catalysts[J]. Applied Catalysis A:General,1999,184(1):81-88.
[18] Durland J R A H. Hydrogenation of phenanthrene[J]. Journal of the American Chemical Society,1937(59):135-136.
[19]李会峰,刘锋,刘泽龙,等.菲在不同加氢催化剂上的转化[J].石油学报(石油加工),2011(1):20-25.
[20] Cameron J M L,Cook J W,Graham W. Catalytic hydrogenation of pyrene[J]. Journal of Chemical Society,1945:286-288.
[21] Jr. Garlock E A,Mosettig E. Studies in the Anthracene Series.I. Methyl Ketones and Carbinolamines Derived from 1,2,3,4-Tetrahydroanthracene[J]. Journal of the american chemical society,1945,67(12):2255-2259.
[22] Alonso F,Yus M. Catalytic Hydrogenation of Organic Compounds using the Ni Cl2-Li-Naphthalene(cat.)Combination[J].Advanced synthesis&catalysis,2001,2(343):188-191.
[23]杨惠斌,王雅纯,江洪波,等. Ni Mo/Al2O3催化剂上菲加氢反应体系动力学[J].化学反应工程与工艺,2014(6):550-556.
[24]周凌,赵静,张德祥.三环芳烃菲在浆态床内的催化加氢转化及动力学研究[J].石油化工,2015(6):705-711.
[25]张小菲,邵正锋,毛国强,等.萘在贵金属Pd、Pt及PdPt催化剂上的加氢活性及耐硫性能[J].物理化学学报,2010(10):2691-2698.
[26] Dufesne P B P H B. New development in hydrocracking:Low pressure high-conversion hydrocracking[J]. Catalysis Today,1987(1):367-384.
[27] Bouchy M P S D P. Hydrogenation and hydrocracking of a model light cycle oil feed. 2. Properties of a sulfides nickelmolybdenum hydrocracking catalyst[J]. Industrial and Engineering Chemistry Research,1993(32):1592-1602.
[28] Barry H. Cooper B B L D. Aromatic saturation of distillates:an overview[J]. Applied Catalysis A:General, 1996(137):203-223.
[29]侯朝鹏,李永丹,夏国富,等.蒽和菲加氢反应热力学分析[J].石油化工,2013(7):761-766.
[30]杨惠斌.菲加氢反应体系的研究[D].上海:华东理工大学,2015.
[31] Dutta R P,Schobert H H. Hydrogenation/dehydrogenation of polycyclic aromatic hydrocarbons using ammonium tetrathiomolybdate as catalyst precursor[J]. Catalysis Today,1996,31(1-2):65-77.
[32]杨惠斌,常小瑞,江洪波,等.菲加氢反应体系的热力学计算和分析[J].化学反应工程与工艺,2012(6):499-505.
[33]王春璐,周涵,王子军,等.稠环芳烃直接加氢的分子模拟研究[J].计算机与应用化学, 2012(10):1221-1224.
[34]王春璐,周涵,王子军,等.菲分子不同碳原子位置加氢初始反应的量子化学[J].石油学报(石油加工),2012(4):642-645.
[35]江夏,宗士猛,李秀生,等.烃分子供氢能力的分子模拟[J].石油学报(石油加工),2012(2):254-259.
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