Synthesis of polyoxymethylene dimethyl ethers from dimethoxymethane and trioxane catalyzed by ionic liquids encapsulated in caged mesoporous KIT-5 material

ZHANG Chao-feng; ZHANG Jing; ZHANG Hao-yu; HUANG Shuang-ping; LI Rui-feng

Volume 48 Issue 4

Apr. 2020

Turn off MathJax

Article Contents

Article Navigation > Journal of Fuel Chemistry and Technology > 2020 > 48(4): 505-512

ZHANG Chao-feng, ZHANG Jing, ZHANG Hao-yu, HUANG Shuang-ping, LI Rui-feng. Synthesis of polyoxymethylene dimethyl ethers from dimethoxymethane and trioxane catalyzed by ionic liquids encapsulated in caged mesoporous KIT-5 material[J]. Journal of Fuel Chemistry and Technology, 2020, 48(4): 505-512.

Citation:

ZHANG Chao-feng, ZHANG Jing, ZHANG Hao-yu, HUANG Shuang-ping, LI Rui-feng. Synthesis of polyoxymethylene dimethyl ethers from dimethoxymethane and trioxane catalyzed by ionic liquids encapsulated in caged mesoporous KIT-5 material[J]. Journal of Fuel Chemistry and Technology, 2020, 48(4): 505-512.

Citation:

ZHANG Chao-feng, ZHANG Jing, ZHANG Hao-yu, HUANG Shuang-ping, LI Rui-feng. Synthesis of polyoxymethylene dimethyl ethers from dimethoxymethane and trioxane catalyzed by ionic liquids encapsulated in caged mesoporous KIT-5 material[J]. Journal of Fuel Chemistry and Technology, 2020, 48(4): 505-512.

PDF( 705 KB)

Synthesis of polyoxymethylene dimethyl ethers from dimethoxymethane and trioxane catalyzed by ionic liquids encapsulated in caged mesoporous KIT-5 material

1.
College of Biomedical Engineering, Taiyuan University of Technology, Taiyuan 030024, China
2.
College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024, China

Funds:

the Natural Science Foundation of Shanxi Province 201801D121062

the Shanxi Scholarship Council of China 2017-037

the Foundation of Taiyuan University of Technology 2016MS03

More Information

Corresponding author: ZHANG Chao-feng, E-mail: zhangchaofeng@tyut.edu.cn
Received Date: 2019-12-20
Rev Recd Date: 2020-03-02

Available Online: 2021-01-23

Publish Date: 2020-04-10

Abstract

Abstract

Four kinds of supported ionic liquid catalysts were prepared by encapsulation of ionic liquids within the nanocage of KIT-5 and were used in the synthesis of polyoxymethylene dimethyl ether (PODE_n) from dimethoxymethane and trioxane; the effects of conditional parameters on the conversion of trioxane and the selectivity to targeted PODE_3-5 were systematically investigated. The results show that the optimum reaction parameters for the synthesis of polyoxymethylene dimethyl ether were: reaction time of 2 h, 100 ℃, dimethoxymethane to trioxane molar ratio of 1.5, and catalyst content of 3%. Under the optimum conditions, the encapsulated catalysts are efficient in the synthesis of polyoxymethylene dimethyl ether, with a similar catalytic activity to the homogeneous counterparts. Moreover, the encapsulated catalysts can be reused several times without remarkable loss of activity and product selectivity, which makes it a promising catalyst for practical applications.
- polyoxymethylene dimethyl ethers,
- ionic liquids,
- KIT-5,
- catalysts

FullText(HTML)

References(29)

References

[1]	DENG X D, CAO Z B, LI X P, HAN D Y, ZHAO R X, LI Y. The synthesis of polyoxymethylene dimethyl ethers for new diesel blending component[J]. Met Org Nano-Met Chem, 2015, 46(12):1842-1847. doi: 10.1080/15533174.2013.862708
[2]	BARANOWSKI C J, BAHMANPOUR A M, KRÖCHER O. Catalytic synthesis of polyoxymethylene dimethyl ethers (OME):A review[J]. Appl Catal B:Environ, 2017, 217:407-420. doi: 10.1016/j.apcatb.2017.06.007
[3]	BOYD R H. Some physical properties of polyoxymethylene dimethyl ethers[J]. J Polym Sci, 1961, 50(153):133-141. doi: 10.1002/pol.1961.1205015316
[4]	XUE Z Z, SHANG H Y, ZHANG Z L, XIONG C H, LU C B, AN G J. Efficient synthesis of polyoxymethylene dimethyl ethers on Al-SBA-15 catalysts with different Si/Al ratios and pore sizes[J]. Energy Fuels, 2017, 31(1):279-286. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=f52da6856df8778cbcd62dd12eedd60e
[5]	郑妍妍, 唐强, 王铁峰, 王金福.聚甲氧基二甲醚的研究进展及前景[J].化工进展, 2016, 35(8):2412-2419. http://d.old.wanfangdata.com.cn/Periodical/hgjz201608018 ZHENG Yan-yan, TANG Qiang, WANG Tie-feng, WANG Jin-fu. Progress and prospect of polyoxymethylene dimethyl ethers[J]. Chem Ind Eng Prog, 2016, 35(8):2412-2419. http://d.old.wanfangdata.com.cn/Periodical/hgjz201608018
[6]	ZHAO Y P, XU Z, CHEN H, FU Y C, SHEN J Y. Mechanism of chain propagation for the synthesis of polyoxymethylene dimethyl ethers[J]. J Energy Chem, 2013, 22(6):833-836. doi: 10.1016/S2095-4956(14)60261-8
[7]	WANG L P, ZHOU S S, LI P, LI P Z, LI Q S, YU Y M. Measurement and thermodynamic models for ternary liquid-liquid equilibrium systems {water+polyoxymethylene dimethyl ethers+4-methyl-2-pentanol} at different temperatures[J]. J Chem Eng Data, 2018, 63(8):3074-3082. doi: 10.1021/acs.jced.8b00323
[8]	STROEFER E, HASSE H, BLAGOV S. Method for producing polyoxymethylene dimethyl ethers from methanol and formaldehyde: US, 7671240[P]. 2010-03-02.
[9]	LIU F, WANG T F, ZHENG Y Y, WANG J F. Synergistic effect of Brønsted and Lewis acid sites for the synthesis of polyoxymethylene dimethyl ethers over highly efficient SO₄^2-/TiO₂ catalysts[J]. J Catal, 2017, 355:17-25. doi: 10.1016/j.jcat.2017.08.014
[10]	ZHANG J Q, LIU D H. Preparation of a hydrophobic-hydrophilic adjustable catalyst surface for the controlled synthesis of polyoxymethylene dimethyl ethers:A potential replacement of diesel fuel[J]. Int J Energy Res, 2017, 42(3):1237-1246.
[11]	王岩, 石磊, 范家麒, 陈飞, 姚杰, 许光文.环丁砜处理磺酸树脂高效催化聚甲氧基二甲醚合成[J].化工学报, 2019, 70(1):116-127. http://d.old.wanfangdata.com.cn/Periodical/hgxb201901014 WANG Yan, SHI Lei, FAN Jia-qi, CHEN Fei, YAO Jie, XU Guang-wen. High-efficiency catalytic synthesis of polyoxymethoxy dimethylether from sulfolane-treated sulfonic acid resin[J]. CIESC J, 2019, 70(1):116-127. http://d.old.wanfangdata.com.cn/Periodical/hgxb201901014
[12]	周林, 李国斌, 李晓娟, 朱江林, 刘超, 陈立宇.阴离子改性MCM-22分子筛的制备及其在催化合成聚甲氧基二甲醚中的应用[J].石油化工, 2019, 48(6):556-562. doi: 10.3969/j.issn.1000-8144.2019.06.005 ZHOU Lin, LI Guo-bin, LI Xiao-juan, ZHU Jiang-lin, LIU Chao, CHEN Li-yu. Preparation of anionically modified MCM-22 zeolites and application in catalytic synthesis of polyoxymethylene dimethyl ether[J]. Petrochem Technol, 2019, 48(6):556-562. doi: 10.3969/j.issn.1000-8144.2019.06.005
[13]	LI H J, SONG H L, CHEN L W, XIA C G. Designed SO₄^2-/Fe₂O₃-SiO₂ solid acids for polyoxymethylene dimethyl ethers synthesis:the acid sites control and reaction pathways[J]. Appl Catal B:Environ, 2014, 165:466-476.
[14]	陈静, 唐中华, 夏春谷, 张新志, 李臻.聚甲氧基甲缩醛的制备方法: 中国, 101182367A[P]. 2008-05-21. CHEN Jing, TANG Zhong-hua, XIA Chun-gu, ZHANG Xin-zhi, LI Zhen. A methode to synthesize polyoxymethylene dimethyl ethers: CN, 101182367A[P]. 2008-05-21.
[15]	WU Q, WANG M, HAO Y, LI H S, ZHAO Y, JIAO Q Z. Synthesis of polyoxymethylene dimethyl ethers catalyzed by Brønsted acid ionic liquids with alkanesulfonic acid groups[J]. Ind Eng Chem Res, 2014, 53(42):16254-16260. doi: 10.1021/ie502409t
[16]	YANG Z Y, HU Y F, MA W T, QI J G, ZHANG X M. Synthesis of polyoxymethylene dimethyl ethers catalyzed by the pyrrolidinonium based ionic liquids[J]. Chem Eng Technol, 2017, 40(10):1784-1791. doi: 10.1002/ceat.201600633
[17]	LI H, BHADURY P S, SONG B A, YANG S. Immobilized functional ionic liquids:Efficient, green, and reusable catalysts[J]. RSC Adv, 2012, 2(33):12525-12551. doi: 10.1039/c2ra21310a
[18]	张朝峰, 张海新, 陈树伟, 李瑞丰.吡啶甲磺酸盐离子液体的固载化及其在聚甲醛二甲醚合成中的催化作用[J].燃料化学学报, 2014, 42(5):609-615. http://www.ccspublishing.org.cn/article/id/100033133 ZHANG Chao-feng, ZHANG Hai-xin, CHEN Shu-wei, LI Rui-feng. Immobilization of N-(3-Sulfopropyl)pyridinium methanesulfonate ionic liquid and its catalytic performance in the synthesis of polyoxymethylene dimethyl ethers[J]. J Fuel Chem Technol, 2014, 42(5):609-615. http://www.ccspublishing.org.cn/article/id/100033133
[19]	张朝峰, 李静, 陈树伟, 张海新, 朱志红, 王建忠, 李瑞丰.一种分子筛负载离子液体催化剂及其催化合成聚甲醛二甲醚的方法: 中国, 103381372B[P]. 2015-08-19. ZHANG Chao-feng, LI jing, CHEN Shu-wei, ZHANG Hai-xin, ZHU Zhi-hong, WANG Jian-zhong, LI Rui-feng. Method for preparing polyoxymethylene dimethyl ethers by using molecular sieve load of ionic liquids as catalyst: CN, 103381372B[P]. 2015-08-19.
[20]	张朝峰, 邢俊德, 刘康军, 朱志红, 王建忠, 李瑞丰.一种磁性纳米咪唑离子液体催化剂及其催化合成聚甲醛二甲醚的方法: 中国, 103381373B[P]. 2016-01-20. ZHANG Chao-feng, XING Jun-de, LIU Kang-jun, ZHU Zhi-hong, WANG Jian-zhong, LI Rui-feng. Method for preparing polyoxymethylene dimethyl ethers by using magnetic nanometer imidazole ionic liquids as catalyst: CN, 103381373B[P]. 2016-01-20.
[21]	DEKA J R, LIN Y H, KAO H M. Ordered cubic mesoporous silica KIT-5 functionalized with carboxylic acid groups for dye removal[J]. RSC Adv, 2014, 4(90):49061-49069. doi: 10.1039/C4RA08819K
[22]	RAMANATHAN A, MAHESWARI R, SUBRAMANIAM B. Facile styrene epoxidation with H₂O₂ over novel niobium containing cage type mesoporous silicate, Nb-KIT-5[J]. Top Catal, 2015, 58(4/6):314-324. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=4b362c19a722f4e8f81e0007a30efa26
[23]	CHERMAHINI A N, HAFIZI H, ANDISHEH N, SARAJI M, SHAHVAR A. The catalytic effect of Al-KIT-5 and KIT-5-SO₃H on the conversion of fructose to 5-hydroxymethylfurfural[J]. Res Chem Intermed, 2017, 43(11):5507-5521.
[24]	KLEITZ F, LIU D, ANILKUMAR G M, PARK I-S, SOLOVYOV L A, SHMAKOV A N, RYOO R. Large cage face-centered-cubic Fm3m mesoporous silica:Synthesis and structure[J]. J Phys Chem B, 2003, 107(51):14296-14300. doi: 10.1021/jp036136b
[25]	李玉阁, 曹祖宾, 李秀萍, 韩冬云, 赵荣祥, 邓小丹, 李丹东.有效碳数-内标法计算聚甲氧基二甲醚的含量[J].应用化工, 2013, 42(9):1729-1733. http://d.old.wanfangdata.com.cn/Periodical/sxhg201309051 LI Yu-ge, CAO Zu-bin, LI Xiu-ping, HAN Dong-yun, ZHAO Rong-xiang, DENG Xiao-dan, LI Dan-dong. Calculate the content of polyoxymethylene dimethyl ethers with the effective carbon numbers-internal standard method[J]. Appl Chem Ind, 2013, 42(9):1729-1733. http://d.old.wanfangdata.com.cn/Periodical/sxhg201309051
[26]	WU C Y, HSU Y T, YANG C M. Structural modulation of cage-like mesoporous KIT-5 silica by post-synthesis treatments with ammonia and/or sulfuric acid[J]. Microporous Mesoporous Mater, 2009, 117:249-256. doi: 10.1016/j.micromeso.2008.06.027
[27]	KALBASI R J, MOSADDEGH N. Synthesis and characterization of Pd-poly (N-vinyl-2-pyrrolidone)/KIT-5 nanocomposite as a polymer-inorganic hybrid catalyst for the Suzuki-Miyaura cross-coupling reaction[J]. J Solid State Chem, 2011, 184(11):3095-3103. doi: 10.1016/j.jssc.2011.09.020
[28]	MIRSAFAEI R, HERAVI M M, AHMADI S, MOSLEMIN M H, HOSSEINNEJAD T. In situ prepared copper nanoparticles on modified KIT-5 as an efficient recyclable catalyst and its applications in click reactions in water[J]. J Mol Catal A:Chem, 2015, 402:100-108. doi: 10.1016/j.molcata.2015.03.006
[29]	WU Y J, LI Z, XIA C G. Silica-gel-supported dual acidic ionic liquids as efficient catalysts for the synthesis of polyoxymethylene dimethyl ethers[J]. Ind Eng Chem Res, 2016, 55(7):1859-1865. doi: 10.1021/acs.iecr.5b04177