低负载量Ru-W-B/NaY催化剂制备及其对对苯二酚加氢性能
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摘要
通过浸渍-化学还原法制备出一系列低负载量的钌基催化剂,在Ru-B二元催化体系中加入少量W,催化性能显著提高。采用XPS、H2-TPD、XRD、SEM、ICP-OES对催化剂物相结构、组成、形貌进行表征,发现采用反加法、添加W、超声波辅助、使用聚乙二醇(PEG)对载体NaY进行涂覆制备的催化剂活性金属粒子分散更均匀,活性位数量更多。以对苯二酚加氢制1,4-环己二醇为探针反应对所制备的催化剂进行活性测试,发现Ru-W-B/NaY-IUP(1500)0.6〔I代表反加法,U代表在制备过程中使用超声波,P代表制备过程中使用了PEG,1500为PEG相对分子质量,0.6为PEG用量(0.6 g)〕加氢性能最为优越,对苯二酚转化率为99.7%,1,4-环己二醇选择性为92.3%,而钌的负载量(以钌在催化剂中所占质量分数计,下同)仅为0.45%。此外,研究了反应液pH对加氢反应的影响,发现反应液pH对反应影响大,当反应液呈碱性时,反应速率得到提高。
A series of low-loading ruthenium-based catalysts were prepared by impregnation-chemical reduction method. The introduction of a small amount of W into the Ru-B binary catalyst system improved the catalytic performance of the catalyst. The structure, composition and surface morphology of the catalysts were characterized by XPS, H2-TPD, XRD, SEM and ICP-OES. It was found that the active metal particles of the catalyst prepared by inverse addition, W addition, ultrasonic assisted technique, and carrier NaY coated by PEG were dispersed more evenly and the number of active sites was more. The activity of the catalyst was tested via hydrogenation of hydroquinone to 1,4-cyclohexanediol. The results showed that Ru-W-B/NaY-IUP(1500)_(0.6)(I means reverse addition, U means ultrasound used in the preparation process,P means PEG used in the preparation process, 1500 means relative molecular mass of PEG, and 0.6 means PEG dosage, 0.6 g) exhibited the best hydrogenation performance. The conversion of hydroquinone was99.7%, the selectivity of 1,4-cyclohexanediol was 92.3%, and the ruthenium loading was only 0.45%(mass fraction of ruthenium in a catalyst, the same below). In addition, the effect of pH value of the reaction solution on the hydrogenation of hydroquinone was studied. The results revealed that the pH value of the reaction solution had a great influence on the reaction. When the reaction solution was alkaline, the reaction rate was greatly accelerated.
A series of low-loading ruthenium-based catalysts were prepared by impregnation-chemical reduction method. The introduction of a small amount of W into the Ru-B binary catalyst system improved the catalytic performance of the catalyst. The structure, composition and surface morphology of the catalysts were characterized by XPS, H2-TPD, XRD, SEM and ICP-OES. It was found that the active metal particles of the catalyst prepared by inverse addition, W addition, ultrasonic assisted technique, and carrier NaY coated by PEG were dispersed more evenly and the number of active sites was more. The activity of the catalyst was tested via hydrogenation of hydroquinone to 1,4-cyclohexanediol. The results showed that Ru-W-B/NaY-IUP(1500)_(0.6)(I means reverse addition, U means ultrasound used in the preparation process,P means PEG used in the preparation process, 1500 means relative molecular mass of PEG, and 0.6 means PEG dosage, 0.6 g) exhibited the best hydrogenation performance. The conversion of hydroquinone was99.7%, the selectivity of 1,4-cyclohexanediol was 92.3%, and the ruthenium loading was only 0.45%(mass fraction of ruthenium in a catalyst, the same below). In addition, the effect of pH value of the reaction solution on the hydrogenation of hydroquinone was studied. The results revealed that the pH value of the reaction solution had a great influence on the reaction. When the reaction solution was alkaline, the reaction rate was greatly accelerated.
引文
[1]Gillespie L J,Liu T H.The reputed dehydrogenation of hydroquinone by palladium black[J].J Am Chem Soc,1931,53(11):3969-3972.
[2]And L F C,Chen Y W.Effect of additive(W,Mo,and Ru)on Ni-Bamorphous alloy catalyst in hydrogenation of p-chloronitrobenzene[J].Ind Eng Chem Res,2006,45(26):8866-8873.
[3]Liu Zili(刘自力),Huang Xuanyan(黄旋燕),Dai Qianwen(代倩雯).Hydrogenation of nitrobenzene to synthesize aniline over Ni-Mo-PEG amorphous[J].Fine Chemicals(精细化工),2014,31(6):722-726.
[4]And S P B,Sawant S B.Kinetics of liquid-phase catalytic hydrogenation of benzophenone to benzhydrol[J].Organic Process Research&Development,2003,7(5):769-773.
[5]Yokoyama A,Komiyama H,Inoue H,et al.The hydrogenation of carbon monoxide by amorphous ribbons[J].Journal of Catalysis,1981,68(2):355-361.
[6]Xie S,Qiao M,Li H,et al.A novel Ru-B/SiO2,amorphous catalyst used in benzene-selective hydrogenation[J].Applied Catalysis A:General,1999,176(1):129-134.
[7]álvarez-Rodríguez J,Rodríguez-Ramos I,Guerrero-Ruiz A,et al.Influence of the nature of support on Ru-supported catalysts for selective hydrogenation of citral[J].Chemical Engineering Journal,2012,204-206(38):169-178.
[8]Wang S,Wei W,Zhao Y,et al.Ru-B amorphous alloy deposited on mesoporous silica nanospheres:An efficient catalyst for D-glucose hydrogenation to D-sorbitol[J].Catalysis Today,2015,258:327-336.
[9]Zhang Z,Suo Y,He J,et al.Selective hydrogenation of orthochloronitrobenzene over biosynthesized ruthenium-platinum bimetallic nanocatalysts[J].Industrial&Engineering Chemistry Research,2016,55(26):7061-7068.
[10]Wang W Y,Yang Y Q,Bao J G,et al.Influence of ultrasonic on the preparation of Ni-Mo-B amorphous catalyst and its performance in phenol hydrodeoxygenation[J].Journal of Fuel Chemistry&Technology,2009,37(6):701-706.
[11]Deng J F,Zhang X,Min E.Amorphous nickel-phosphorus alloy deposited on a support and its hydrogenation activity[J].Applied Catalysis,1988,37:339-343.
[12]Deng J F,Chen H.A novel amorphous Ni-W-P alloy powder and its hydrogenation activity[J].Journal of Materials Science Letters,1993,12(19):1508-1510.
[13]Deng J F,Yang J,Sheng S S,et al.The study of ultrafine Ni-B and Ni-P amorphous alloy powders as catalysts[J].Journal of Catalysis,1994,150(2):434-438.
[14]Zheng L,Dai W L,Bo L,et al.The effect of boron on selective benzene hydrogenation to cyclohexene over ruthenium boride powders[J].Journal of Catalysis,1999,187(1):253-256.
[15]Deng J F,Li H,Wang W.Progress in design of new amorphous alloy catalysts[J].Catalysis Today,1999,51(1):113-125.
[16]Qiao M H,Xie S H,Dai W L,et al.Ultrafine Ni-Co-W-B amorphous alloys and their activities in benzene hydrogenation to cyclohexane[J].Catalysis Letters,2001,71(3/4):187-192.
[17]Zong Baoning(宗保宁).Applications of the amorphous alloy catalyst and magnetically stabilized bed technology in petrochemical processes[J].Chinese Journal of Catalysis(催化学报),2008,29(9):873-877
[18]Zuo Jiaqi(左佳齐),Ning Bin(宁彬).The birth of a new platform Technology[J].Sinopec(中国石化),2006,(2):13-16.
[19]Bai G,Wen X,Zhao Z,et al.Chemoselective hydrogenation of benzoic acid over Ni-Zr-B-PEG(800)nanoscale amorphous alloy in water[J].Industrial&Engineering Chemistry Research,2013,52(6):2266-2272.
[20]Zong B N,Mu Xuhong,Zhang X X,et al.Research,development,and application of amorphous nickel alloy catalysts prepared by meltquenching[J].Chinese Journal of Catalysis,2013,34(5):828-837.
[21]Bhosale R R,Pujari S R,Lande M K,et al.Photocatalytic activity and characterization of sol-gel-derived Ni-doped TiO2-coated active carbon composites[J].Applied Surface Science,2012,261(1):835-841.
[22]Ju Jiangyue(鞠江月),Wang Yaming(王亚明),Jiang Lihong(蒋丽红),et al.Hydrogenation of turpentine catalyzed by NiCoB/TiO2amorphous alloy catalysts[J].Fine Chemicals(精细化工),2017,34(1):66-73.
[23]Qin Huian(秦会安),Huang Zhengxu(黄振旭),Liu Shouchang(刘寿长).Study on the unsupported Ru-Zn-B catalysts for selective hydrogenation of benzene to cyclohexene[J].Journal of Xinyang Normal University:Natural Science Edition(信阳师范学院学报:自然科学版),2007,20(3):350-352.
[24]Ji D,Li H,Li Z,et al.Study on liquid-phase hydrogenation of paranitrotoluene over Ru-based catalysts[J].Canadian Journal of Chemical Engineering,2017,9999:1-8
[25]Chen Songying(陈诵英),Wang Qin(王琴).Preparation principle and technology of solid catalyst[M].Beijing:Chemical Industry Press(化学工业出版社),2012:253-272
[26]Li G,Dong P,Ji D,et al.Effect of support materials on liquid-phase hydrogenation of hydroquinone over ruthenium catalysts[J].Solid State Sciences,2013,23(9):13-16.
[27]Yang Liang(杨良),Wu Yanping(吴炎平),Han Wenxiang(韩文祥),et al.Infrared spectra of nano-sized NaY zeolite[J].Bulletin of the Chinese Ceramic society(硅酸盐通报),2017,(12):4169-4172.
[28]Xu S X,Li F Y.Preparation of nanosized RuB with lower Ru content supported on Al2O3 and its catalytic activity[J].Advanced Materials Research,2012,4:557-562.
[29]Li Hongwei(李红伟),Li Zeyu(李泽宇),Ji Dong(季东),et al.Hydrogenation of p-nitrotoluene to p-methyl-cyclohexylamine over high dispersion Ru-PEGx/NaY catalyst[J].Fine Chemicals(精细化工),2018,35(10):1673-1677.
[30]Dong R L,Li M A,Zhang F,et al.Effect of polyethylene glycol on the dispersion of Al2O3 particles in an aqueous suspension[J].Journal of Jiangsu Polytechnic University,2009,(1):32-37
[31]Bai G,Niu L,Qiu M,et al.Liquid-phase selective hydrogenation of benzophenone over ultrasonic-assisted Ni-La-B amorphous alloy catalyst[J].Catalysis Communications,2011,12(3):212-216.
[32]Liu S,Liu Z,Wang Z,et al.A novel amorphous alloy Ru-La-B/ZrO2,catalyst with high activity and selectivity for benzene selective hydrogenation[J].Applied Catalysis A:General,2006,313(1):49-57.
[33]Bianchi C L,Ragaini V,Cattania M G.An XPS study on ruthenium compounds and catalysts[J].Materials Chemistry&Physics,1991,29(1/2/3/4):297-306.
[34]Kawashima A,Asami K,Hashimoto K.An XPS study of anodic behavior of amorphous nickel-phosphorus alloys containing chromium,molybdenum or tungsten in 1 M HCl[J].Corrosion Science,1985,16(3):807-823.
[35]Sankuia X U,Wang X,Limina L I,et al.Effect of supercritical methanol treatment on the surface property of activated carbon and the activity of Ru/activated carbon catalyst[J].Chinese Journal of Applied Chemistry,2011,28(8):936-941.
[36]Grünert W,Shpiro E S,Feldhaus R,et al.Reduction behavior and metathesis activity of WO3/Al2O3 catalysts:I.An XPS investigation of WO3/Al2O3 catalysts[J].Journal of Catalysis,1989,107(2):444-456.
[37]Sun H,Guo W,Zhou X,et al.Progress in Ru-based amorphous alloy catalysts for selective hydrogenation of benzene to cyclohexene[J].Chinese Journal of Catalysis,2011,32(1/2):1-16.
[38]Bai G,Zhao Z,Niu L,et al.Effect of polymers and alkaline earth metals on the catalytic performance of Ni-B amorphous alloy in benzophenone hydrogenation[J].Catalysis Communications,2012,23(23):34-38.
[39]Bai G,Niu L,Zhao Z,et al.Ni-La-B amorphous alloys supported on SiO2 andγ-Al2O3 for selective hydrogenation of benzophenone[J].Journal of Molecular Catalysis A:Chemical,2012,363/364:411-416.
[40]Li H,Ji D,Li Y,et al.Effect of alkaline earth metals on the liquid-phase hydrogenation of hydroquinone over Ru-based catalysts[J].Solid State Sciences,2015,50:85-90.
[41]Li Guixian(李贵贤),Gao Yuan(高远),Sun Liedong(孙烈东),et al.Preparation of Ru-B/γ-Al2O3 amorphous alloy catalyst and study on its catalytic performance in the hydrogenation of hydroquinone[J].Modern Chemical Industry(现代化工),2017,37(5):115-119.
[42]Li Guixian(李贵贤),Li Qiang(李强),Zeng Xiaoliang(曾晓亮),et al.Preparation of Ru/NaY nanoparticle catalysts by microemulsion method for catalytic hydrogenation of hydroquinone[J].Journal of Molecular Catalysis(分子催化),2017,31(4):316-324.
[43]Ji Dong(季东),Li Yu(李昱),Cao Yanwei(曹彦伟),et al.Catalytic hydrogenation of hydroquinone over Ru/HZSM-5 catalyst[J].Modern Chemical Industry(现代化工),2016,36(5):114-117,119.
[44]Sun Liang(孙亮),Rong Zeming(荣泽明),Zhang Wenjun(张文君),et al.Selective hydrogenation of hydroquinone to 1,4-cyclohexanediol over Ru-Rh/AC catalyst[J].Petrochemical Technology(石油化工),2013,42(2):146-151.
[45]Wang Hongjun(王洪军),Wang Xingquan(汪星全),Zhang Li(张丽),et al.Study on the synthesis of 1,4-cyclohexanediol through catalytic hydrogenation of hydroquinone[J].Journal of Molecular Catalysis(China)(分子催化),2010,24(4):315-321.
[46]Wang Xiaorui(王小瑞),Li Guixian(李贵贤),Dong Peng(董鹏).Hydrogenation of 1,4-benzenediol to 1,4-cyclohexanediol over Ruthenium-based catalysts[J].Contemporary Chemical Industry(当代化工),2015,44(10):2303-2305.
[47]Bai G,Li F,Fan X,et al.Continuous hydrogenation of hydroquinone to 1,4-cyclohexanediol over alkaline earth metal modified nickelbased catalysts[J].Catalysis Communications,2012,17:126-130.
[48]Bai Guoyi(白国义),Ning Huisen(宁慧森),Zhang Chenfang(张晨芳),et al.A method for the synthesis of 1,4-cyclohexanedione:CN101020627 A[P].2007-08-22.
[49]Makowski P,Demir Cakan R,Antonietti M,et al.Selective partial hydrogenation of hydroxy aromatic derivatives with palladium nanoparticles supported on hydrophilic carbon[J].Cheminform,2008,39(8):999-1001.
[50]Yuan G,Keane M A.Catalyst deactivation during the liquid phase hydrodechlorination of 2,4-dichlorophenol over supported Pd:influence of the support[J].Catalysis Today,2003,88(1):27-36.
[51]Liu X,Wang X.Highly dispersive PdCoB catalysts for dechlorination of chlorophenols[J].Journal of Hazardous Materials,2014,274:63-71.
[2]And L F C,Chen Y W.Effect of additive(W,Mo,and Ru)on Ni-Bamorphous alloy catalyst in hydrogenation of p-chloronitrobenzene[J].Ind Eng Chem Res,2006,45(26):8866-8873.
[3]Liu Zili(刘自力),Huang Xuanyan(黄旋燕),Dai Qianwen(代倩雯).Hydrogenation of nitrobenzene to synthesize aniline over Ni-Mo-PEG amorphous[J].Fine Chemicals(精细化工),2014,31(6):722-726.
[4]And S P B,Sawant S B.Kinetics of liquid-phase catalytic hydrogenation of benzophenone to benzhydrol[J].Organic Process Research&Development,2003,7(5):769-773.
[5]Yokoyama A,Komiyama H,Inoue H,et al.The hydrogenation of carbon monoxide by amorphous ribbons[J].Journal of Catalysis,1981,68(2):355-361.
[6]Xie S,Qiao M,Li H,et al.A novel Ru-B/SiO2,amorphous catalyst used in benzene-selective hydrogenation[J].Applied Catalysis A:General,1999,176(1):129-134.
[7]álvarez-Rodríguez J,Rodríguez-Ramos I,Guerrero-Ruiz A,et al.Influence of the nature of support on Ru-supported catalysts for selective hydrogenation of citral[J].Chemical Engineering Journal,2012,204-206(38):169-178.
[8]Wang S,Wei W,Zhao Y,et al.Ru-B amorphous alloy deposited on mesoporous silica nanospheres:An efficient catalyst for D-glucose hydrogenation to D-sorbitol[J].Catalysis Today,2015,258:327-336.
[9]Zhang Z,Suo Y,He J,et al.Selective hydrogenation of orthochloronitrobenzene over biosynthesized ruthenium-platinum bimetallic nanocatalysts[J].Industrial&Engineering Chemistry Research,2016,55(26):7061-7068.
[10]Wang W Y,Yang Y Q,Bao J G,et al.Influence of ultrasonic on the preparation of Ni-Mo-B amorphous catalyst and its performance in phenol hydrodeoxygenation[J].Journal of Fuel Chemistry&Technology,2009,37(6):701-706.
[11]Deng J F,Zhang X,Min E.Amorphous nickel-phosphorus alloy deposited on a support and its hydrogenation activity[J].Applied Catalysis,1988,37:339-343.
[12]Deng J F,Chen H.A novel amorphous Ni-W-P alloy powder and its hydrogenation activity[J].Journal of Materials Science Letters,1993,12(19):1508-1510.
[13]Deng J F,Yang J,Sheng S S,et al.The study of ultrafine Ni-B and Ni-P amorphous alloy powders as catalysts[J].Journal of Catalysis,1994,150(2):434-438.
[14]Zheng L,Dai W L,Bo L,et al.The effect of boron on selective benzene hydrogenation to cyclohexene over ruthenium boride powders[J].Journal of Catalysis,1999,187(1):253-256.
[15]Deng J F,Li H,Wang W.Progress in design of new amorphous alloy catalysts[J].Catalysis Today,1999,51(1):113-125.
[16]Qiao M H,Xie S H,Dai W L,et al.Ultrafine Ni-Co-W-B amorphous alloys and their activities in benzene hydrogenation to cyclohexane[J].Catalysis Letters,2001,71(3/4):187-192.
[17]Zong Baoning(宗保宁).Applications of the amorphous alloy catalyst and magnetically stabilized bed technology in petrochemical processes[J].Chinese Journal of Catalysis(催化学报),2008,29(9):873-877
[18]Zuo Jiaqi(左佳齐),Ning Bin(宁彬).The birth of a new platform Technology[J].Sinopec(中国石化),2006,(2):13-16.
[19]Bai G,Wen X,Zhao Z,et al.Chemoselective hydrogenation of benzoic acid over Ni-Zr-B-PEG(800)nanoscale amorphous alloy in water[J].Industrial&Engineering Chemistry Research,2013,52(6):2266-2272.
[20]Zong B N,Mu Xuhong,Zhang X X,et al.Research,development,and application of amorphous nickel alloy catalysts prepared by meltquenching[J].Chinese Journal of Catalysis,2013,34(5):828-837.
[21]Bhosale R R,Pujari S R,Lande M K,et al.Photocatalytic activity and characterization of sol-gel-derived Ni-doped TiO2-coated active carbon composites[J].Applied Surface Science,2012,261(1):835-841.
[22]Ju Jiangyue(鞠江月),Wang Yaming(王亚明),Jiang Lihong(蒋丽红),et al.Hydrogenation of turpentine catalyzed by NiCoB/TiO2amorphous alloy catalysts[J].Fine Chemicals(精细化工),2017,34(1):66-73.
[23]Qin Huian(秦会安),Huang Zhengxu(黄振旭),Liu Shouchang(刘寿长).Study on the unsupported Ru-Zn-B catalysts for selective hydrogenation of benzene to cyclohexene[J].Journal of Xinyang Normal University:Natural Science Edition(信阳师范学院学报:自然科学版),2007,20(3):350-352.
[24]Ji D,Li H,Li Z,et al.Study on liquid-phase hydrogenation of paranitrotoluene over Ru-based catalysts[J].Canadian Journal of Chemical Engineering,2017,9999:1-8
[25]Chen Songying(陈诵英),Wang Qin(王琴).Preparation principle and technology of solid catalyst[M].Beijing:Chemical Industry Press(化学工业出版社),2012:253-272
[26]Li G,Dong P,Ji D,et al.Effect of support materials on liquid-phase hydrogenation of hydroquinone over ruthenium catalysts[J].Solid State Sciences,2013,23(9):13-16.
[27]Yang Liang(杨良),Wu Yanping(吴炎平),Han Wenxiang(韩文祥),et al.Infrared spectra of nano-sized NaY zeolite[J].Bulletin of the Chinese Ceramic society(硅酸盐通报),2017,(12):4169-4172.
[28]Xu S X,Li F Y.Preparation of nanosized RuB with lower Ru content supported on Al2O3 and its catalytic activity[J].Advanced Materials Research,2012,4:557-562.
[29]Li Hongwei(李红伟),Li Zeyu(李泽宇),Ji Dong(季东),et al.Hydrogenation of p-nitrotoluene to p-methyl-cyclohexylamine over high dispersion Ru-PEGx/NaY catalyst[J].Fine Chemicals(精细化工),2018,35(10):1673-1677.
[30]Dong R L,Li M A,Zhang F,et al.Effect of polyethylene glycol on the dispersion of Al2O3 particles in an aqueous suspension[J].Journal of Jiangsu Polytechnic University,2009,(1):32-37
[31]Bai G,Niu L,Qiu M,et al.Liquid-phase selective hydrogenation of benzophenone over ultrasonic-assisted Ni-La-B amorphous alloy catalyst[J].Catalysis Communications,2011,12(3):212-216.
[32]Liu S,Liu Z,Wang Z,et al.A novel amorphous alloy Ru-La-B/ZrO2,catalyst with high activity and selectivity for benzene selective hydrogenation[J].Applied Catalysis A:General,2006,313(1):49-57.
[33]Bianchi C L,Ragaini V,Cattania M G.An XPS study on ruthenium compounds and catalysts[J].Materials Chemistry&Physics,1991,29(1/2/3/4):297-306.
[34]Kawashima A,Asami K,Hashimoto K.An XPS study of anodic behavior of amorphous nickel-phosphorus alloys containing chromium,molybdenum or tungsten in 1 M HCl[J].Corrosion Science,1985,16(3):807-823.
[35]Sankuia X U,Wang X,Limina L I,et al.Effect of supercritical methanol treatment on the surface property of activated carbon and the activity of Ru/activated carbon catalyst[J].Chinese Journal of Applied Chemistry,2011,28(8):936-941.
[36]Grünert W,Shpiro E S,Feldhaus R,et al.Reduction behavior and metathesis activity of WO3/Al2O3 catalysts:I.An XPS investigation of WO3/Al2O3 catalysts[J].Journal of Catalysis,1989,107(2):444-456.
[37]Sun H,Guo W,Zhou X,et al.Progress in Ru-based amorphous alloy catalysts for selective hydrogenation of benzene to cyclohexene[J].Chinese Journal of Catalysis,2011,32(1/2):1-16.
[38]Bai G,Zhao Z,Niu L,et al.Effect of polymers and alkaline earth metals on the catalytic performance of Ni-B amorphous alloy in benzophenone hydrogenation[J].Catalysis Communications,2012,23(23):34-38.
[39]Bai G,Niu L,Zhao Z,et al.Ni-La-B amorphous alloys supported on SiO2 andγ-Al2O3 for selective hydrogenation of benzophenone[J].Journal of Molecular Catalysis A:Chemical,2012,363/364:411-416.
[40]Li H,Ji D,Li Y,et al.Effect of alkaline earth metals on the liquid-phase hydrogenation of hydroquinone over Ru-based catalysts[J].Solid State Sciences,2015,50:85-90.
[41]Li Guixian(李贵贤),Gao Yuan(高远),Sun Liedong(孙烈东),et al.Preparation of Ru-B/γ-Al2O3 amorphous alloy catalyst and study on its catalytic performance in the hydrogenation of hydroquinone[J].Modern Chemical Industry(现代化工),2017,37(5):115-119.
[42]Li Guixian(李贵贤),Li Qiang(李强),Zeng Xiaoliang(曾晓亮),et al.Preparation of Ru/NaY nanoparticle catalysts by microemulsion method for catalytic hydrogenation of hydroquinone[J].Journal of Molecular Catalysis(分子催化),2017,31(4):316-324.
[43]Ji Dong(季东),Li Yu(李昱),Cao Yanwei(曹彦伟),et al.Catalytic hydrogenation of hydroquinone over Ru/HZSM-5 catalyst[J].Modern Chemical Industry(现代化工),2016,36(5):114-117,119.
[44]Sun Liang(孙亮),Rong Zeming(荣泽明),Zhang Wenjun(张文君),et al.Selective hydrogenation of hydroquinone to 1,4-cyclohexanediol over Ru-Rh/AC catalyst[J].Petrochemical Technology(石油化工),2013,42(2):146-151.
[45]Wang Hongjun(王洪军),Wang Xingquan(汪星全),Zhang Li(张丽),et al.Study on the synthesis of 1,4-cyclohexanediol through catalytic hydrogenation of hydroquinone[J].Journal of Molecular Catalysis(China)(分子催化),2010,24(4):315-321.
[46]Wang Xiaorui(王小瑞),Li Guixian(李贵贤),Dong Peng(董鹏).Hydrogenation of 1,4-benzenediol to 1,4-cyclohexanediol over Ruthenium-based catalysts[J].Contemporary Chemical Industry(当代化工),2015,44(10):2303-2305.
[47]Bai G,Li F,Fan X,et al.Continuous hydrogenation of hydroquinone to 1,4-cyclohexanediol over alkaline earth metal modified nickelbased catalysts[J].Catalysis Communications,2012,17:126-130.
[48]Bai Guoyi(白国义),Ning Huisen(宁慧森),Zhang Chenfang(张晨芳),et al.A method for the synthesis of 1,4-cyclohexanedione:CN101020627 A[P].2007-08-22.
[49]Makowski P,Demir Cakan R,Antonietti M,et al.Selective partial hydrogenation of hydroxy aromatic derivatives with palladium nanoparticles supported on hydrophilic carbon[J].Cheminform,2008,39(8):999-1001.
[50]Yuan G,Keane M A.Catalyst deactivation during the liquid phase hydrodechlorination of 2,4-dichlorophenol over supported Pd:influence of the support[J].Catalysis Today,2003,88(1):27-36.
[51]Liu X,Wang X.Highly dispersive PdCoB catalysts for dechlorination of chlorophenols[J].Journal of Hazardous Materials,2014,274:63-71.