Citation: HUANG Runjun, ZHOU Jiatian, XIE wei, CHEN donglian, WEI dongping, YUAN Aiqun, LIANG Hui. Synthesis of Benzaldehyde Glycol Acetal Catalyzed by Aluminum Dihydrogen Tripolyphosphate Supported on Modified Activated Carbon[J]. Chinese Journal of Applied Chemistry, ;2016, 33(6): 649-654. doi: 10.11944/j.issn.1000-0518.2016.06.150378 shu

Synthesis of Benzaldehyde Glycol Acetal Catalyzed by Aluminum Dihydrogen Tripolyphosphate Supported on Modified Activated Carbon

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a Guilin University of Technology at Nanning, Nanning 530001, China;
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b College of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Nanning 530006, China;
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c Guangxi Vocational & Technical Institute of Industry, Nanning 530004, China

Corresponding author: YUAN Aiqun,
Received Date: 27 October 2015
Available Online: 17 December 2015
Fund Project:

Benzaldehyde glycol acetal was synthesized by aluminum dihydrogen tripolyphosphate supported on nitric acid modified activated carbon. The effect of the molar ratio of alcohol to aldehyde, catalyst amount and reaction time on the yield were studied by single-factor experiments. Orthogonal design was used to obtain the optimized conditions for the synthesis of benzaldehyde glycol acetal. The results show that the three main influencing factors are in the order as follows:the molar ratio of alcohol to aldehyde >the reaction time >the quantity of water carrying agent >the quantity of catalyst. The optimal technical conditions are:temperature 110℃, benzaldehyde 0.2 mol, the molar ratio of alcohol to aldehyde is 2.5, reaction time 75 min, the quantity of catalyst 4%, water-carrying agent of cyclohexane 25 mL. Under these conditions, the yield of benzaldehyde glycol acetal is above 86.5%. The catalyst can be recycled for multiple uses and the acetal yield is 86.0% after five cycles.
- aluminum dihydrogen tripolyphosphate,
- benzaldehyde glycol acetal,
- activated carbon,
- catalysis
1. [1]
  [1] Братс И Н.Химия Душистых Веществ[M].LIU Shuwen Trans.Beijing:Light Industry Press,1984:250(in Chinese).勃拉图斯N H.香料化学[M].刘树文译.北京:轻工业出版社,1984:250.
2. [2]
  [2] LI Shuwen,FAN Rulin Trans.Practical Handbook of Organic Chemistry[M].Shanghai:Shanghai Science and Technology Press,1981:319(in Chinese).李述文,范如霖编译.实用有机化学手册[M].上海:上海科技出版社,1981:319.
3. [3]
  [3] Han X X,Yan W,Chen K K,et al.Heteropolyacid-based Ionic Liquids as Effective Catalysts for the Synthesis of Benzaldehyde Glycol Acetal[J].Appl Catal A:Gen,2014,485(4):149-156.
4. [4]
  [4] Tang J,Song J Y,Wang G,et al.Novel,Green,Simple and Uncatalyzed Route for High Yield Preparation of Benzaldehyde Glycol Acetal[J].Chem Res Chinese Univ,2011,27(5):799-802.
5. [5]
  [5] Jing H W,Wang X M,Liu Y,et al.Preparation of Magnetic Nanocomposites of Solid Acid Catalysts and Their Applicability in Esterification[J].Chinese J Catal,2015,36(2):244-251.
6. [6]
  [6] YANG Shuijin,DENG Manchen,XIE Ping.Synthesis of Benzaldehyde Glycol Acetal Catalyzed with p-Toluene Sulfonic Acid[J].Adv Fine Petrochem,2010,11(4):39-41(in Chinese).杨水金,邓满臣,谢萍.对甲苯磺酸催化合成苯甲醛乙二醇缩醛[J].精细石油化工进展,2010,11(4):39-41.
7. [7]
  [7] MAO Zhihong,WANG Jie,LI Guixian,et al.Synthesis of Benzaldehyde Cylic Ethylic Acetal by the H₅PMo₁₀V₂O₄₀ Immobilized on Silylated Palygorskite[J].J Mol Catal,2011,25(5):393-398(in Chinese).毛志红,王洁,李贵贤,等.硅烷化凹凸棒石负载H₅PMo₁₀V₂O₄₀催化合成苯甲醛乙二醇缩醛[J].分子催化,2011,25(5):393-398.
8. [8]
  [8] CHEN Xiaoyan,YANG Hao,XIE Hao,et al.Synthesis of Benzaldehyde Glycol Acetal Catalyzed by Expandable Graphite Modified Under Microwave Irradiation[J].Fine Chem,2011,28(9):880-882(in Chinese).陈小燕,杨浩,谢昊,等.微波辐射改性可膨胀石墨催化合成苯甲醛乙二醇缩醛[J].精细化工,2011,28(9):880-882.
9. [9]
  [9] ZHAO Lun,TANG Dong.The Synthesis of Benzaldehyde Glycol Acetal by Phosphotungstic Acid Supported on Active Carbon[J].J Changchun Normal Univ(Nat Sci),2013,30(3):66-69(in Chinese).赵仑,唐栋.活性炭负载磷钨酸催化合成苯甲醛乙二醇缩醛[J].长春师范学院学报(自然科学版),2013,30(3):66-69.
10. [10]
  [10] WU Shengfu,HUANG Runjun,CHEN Donglian,et al.Characteristics of Intercalation Reaction Between Aluminum Dihydrogen Tripolyphosphate and Organic Amine[J].Chinese J Appl Chem,2014,31(7):847-851(in Chinese).吴胜富,黄润均,陈东莲,等.三聚磷酸二氢铝与有机胺的插层反应特征[J].应用化学,2014,31(7):847-851.
11. [11]
  [11] YUAN Aiqun.Synthesis and Characterization of Aluminum Tripolyphosphate Hydrate[J].Guangxi Sci,2000,7(4):266-269(in Chinese).袁爱群.三聚磷酸二氢铝二水物的合成和表征[J].广西科学,2000,7(4):266-269.
12. [12]
  [12] WANG Jing.Preparation and Catalytic Performance of Loaded Aluminum Dihydrogen Tripolyphosphate Catalyst[D].Nanning:Guangxi University for Nationalities,2013(in Chinese).王璟.附载型三聚磷酸二氢铝催化剂的制备及其催化性能的研究[D].南宁:广西民族大学,2013.
13. [13]
  [13] ZHOU Jiatian.Catalytic Synthesis of Benzaldehyde Glycol Acetal by Aluminum Dihydrogen Tripolyphosphate[D].Nanning:Guangxi University for Nationalities,2015(in Chinese).周家添.负载型三聚磷酸二氢铝催化合成苯甲醛乙二醇缩醛[D].南宁:广西民族大学,2015.
14. [14]
  [14] LIANG Hui.Preparation and Catalytic Performance of Aluminum Dihydrogen Triphosphate Heterogeneous Catalyst[D].Nanning:Guangxi University for Nationalities,2015(in Chinese).梁慧.三聚磷酸二氢铝非均相催化剂的制备和催化性能[D].南宁:广西民族大学,2015.
15. [15]
  [15] WANG Weikun,XU Ting,XU Yulin.Catalytic Synthesis of Benzaldehyde Glycol Acetal with H₃PW₁₂O₄₀/TiO₂-SiO₂[J].Chem Intermed,2014,10(4):50-54(in Chinese).王巍焜,许停,徐玉林,等.H₃PW₁₂O₄₀/TiO₂-SiO₂催化合成苯甲醛乙二醇缩醛[J].化工中间体,2014,10(4):50-54.
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