Synthesis and physicochemical characterization of polyoxymethylene dimethyl ethers
- Corresponding author: CHEN Jing, chenj@licp.cas.cn.
Citation:
KANG Mei-rong, SONG He-yuan, JIN Fu-xiang, CHEN Jing. Synthesis and physicochemical characterization of polyoxymethylene dimethyl ethers[J]. Journal of Fuel Chemistry and Technology,
;2017, 45(7): 837-845.
UCHIDA T, KURITA Y, KUBO M. The dipole moments and the strucures of polyoxymethylene dimethyl ethers[J]. J Polym Sci, 1956,19(92):365-372. doi: 10.1002/pol.1956.120199215
ARVIDSON M, FAKLEY M E, SPENCER M S. Lithium Halide-Assisted formation of polyoxymethylene dimethyl ethers from dimethoxymethane and formaldehyde[J]. J Mol Catal, 1987,41(3):391-393. doi: 10.1016/0304-5102(87)80118-9
VIGIER F, COUTANCEAU C, LÉGERJ M, DUBOIS J L. Polyoxymethylene dimethyl ether (CH3O(CH2O)nCH3) oxidation on Pt and Pt/Ru supported catalysts[J]. J Power Sources, 2008,175(1):82-90. doi: 10.1016/j.jpowsour.2007.09.053
MASAHIRO W, HIROYUKI U, STEVE B, JEAN-LUC D. Fuel cells using an oxy-carbon fuel soluble in aqueous meduim: EP, 1993159A1[P]. 2008-11-19.
BURGER J, SIEGERT M, STRÖFER E, HASSE H. Poly(oxymethylene) dimethyl ethers as components of tailored diesel fuel:Properties, synthesis and purification concepts[J]. Fuel, 2010,89(11):3315-3319. doi: 10.1016/j.fuel.2010.05.014
ZHAO Q, WANG H, QIN ZHF, WU ZH W, WU J B, FAN W B, WANG J G. Synthesis of polyoxymethylene dimethyl ethers from methanol and trioxymethylene with molecular sieves as catalysts[J]. J Fuel Chem Technol, 2011,39(12):918-923.
WU J B, WU Z W, WANG R Y, SHI R P, QIN Z F, ZHU H Q, DONG M, FAN W B, WANG J G. Recent research progresses in the catalytic synthesis of methyl formate, dimethoxymethane and polyoxymethylene dimethyl ethers from methano[J]. J Fuel Chem Technol, 2015,43(7):816-828.
GAO X C, YANG W M, LIU Z C, GAO H X. Catalytic performance of HZSM-5 molecular sieve for synthesis of polyoxymethylene dimethyl ethers[J]. Chin J Catal, 2012,33(8):1389-1394.
LI H J, SONG H L, ZHAO F, CHEN L W, XIA CH G. Chemical equilibrium controlled synthesis of polyoxymethylene dimethyl ethers over sulfated titania[J]. J Energy Chem, 2015,24(2):239-244. doi: 10.1016/S2095-4956(15)60307-2
REN Y, HUANG Z H, MIAO H Y, DI Y G, JIANG D M, ZENG K, LIU B, WANG X B. Combustion and emissions of a DI diesel engine fuelled with diesel-oxygenate blends[J]. Fuel, 2008,87(12):2691-2697. doi: 10.1016/j.fuel.2008.02.017
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
BURGER J, STRÖFER E, HASSE H. Chemical equilibrium and reaction kinetics of the heterogeneously catalyzed formation of poly(oxymethylene) dimethyl ethers from methylal and trioxane[J]. Ind Eng Chem Res, 2012,51(39):12751-12761. doi: 10.1021/ie301490q
CHEN J, SONG H Y, XIA C G, KANG M R, JIN R H. System and method for continuously producing polyoxymethylene dialkyl ethers: AU, 2012268915[P]. 2014-05-15.
CHEN J, SONG H Y, XIA C G, LI Z. Method for synthesizing polyoxymethylene dimethyl ethers catalyzed by an ionic liquid: US, 0288343[P]. 2011-11-24.
SCOTT A P, RADOM L. Harmonic vibrational frequencies:An evaluation of Hartree-Fock, Moller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors[J]. J Phys Chem, 1996,100(41):16502-16513. doi: 10.1021/jp960976r
PARLAK C. Theoretical and experimental vibrational spectroscopic study of 4-(1-pyrrolidinuyl) piperidine[J]. J Mol Struct, 2010,966(1):1-7.
DIKMEN G, ALVER Ö. NMR, FT-IR, Raman and UV-Vis spectroscopic investigation and DFT study of 6-bromo-3-pyridinyl boronic acid[J]. J Mol Struct, 2015,1099:625-632. doi: 10.1016/j.molstruc.2015.05.063
ANDERSSON M P, UVDAL P. New scale factors for harmonic vibrational frequencies using the B3LYP density functional method with the triple-ξ basis set 6-311+G(d, p)[J]. J Phys Chem A, 2005,109(12):2937-2941. doi: 10.1021/jp045733a
SONG D Y, CHEN J. Densities and viscosities for ionic liquids mixtures containing[eOHmin][BF4], [bmim][BF4] and[bpy][J]. J Chem Thermodyn, 2014,77:137-143. doi: 10.1016/j.jct.2014.05.016
MEHRDAD A, NIKNAM Z. Investigation on the interactions of poly(ethylene oxide) and ionic liquid 1-butyl-3-methyl-imidazolium bromide by viscosity and spectroscopy[J]. J Chem Eng Data, 2016,61(5):1700-1709. doi: 10.1021/acs.jced.5b00428
LINTON W H, GOODMAN H H. Physical properties of high molecular weight acetal resins[J]. J Appl Polym Sci, 1959,1(2):179-184. doi: 10.1002/app.1959.070010208
GUNBAS G, HAFEZI N, SHEPPARD W L, OLMSTEAD M M, STOYANOVA I V, THAM F S, MEYER M P, MASCAL M. Extreme oxatriquinanes and a record C-O bond length[J]. Nat Chem, 2012,4(12):1018-1023. doi: 10.1038/nchem.1502
ALLINGER N L, LⅡ J H, SCHAEFER H F. Molecular mechanics (MM4) studies on unusually long carbon-carbon bond distances in hydrocarbons[J]. J Chem Theory Comput, 2016,12(6):2774-2778. doi: 10.1021/acs.jctc.5b00926
SHAIKH M S, SHARIFF A M, BUSTAM M A, MURSHID G. Physicochemical properties of aqueous solutions of sodium glycinate in the non-precipitation regime from 298.15 to 343.15K[J]. Chin J Chem Eng, 2015,23(3):536-540. doi: 10.1016/j.cjche.2013.11.001
MAZINANI S, SAMSAMI A, JAHANMIRI A. Solubiity (at low partial pressures), density, viscosity, and corrosion rate of carbon dioxide in blend solutions of monoethanolamine (MEA) and sodium glycinate (SG)[J]. J Chem Eng Data, 2011,56(7):3163-3168. doi: 10.1021/je2002418
KUMARI A, SANDEEPA K, KUMAR T P, SATYAVATHI B. Solubility, thermodynamic properties, and derived excess properties of benzoic acid in (acetic acid + water) and (acetic acid + toluene) binary mixtures[J]. J Chem Eng Data, 2016,61(1):67-77. doi: 10.1021/acs.jced.5b00197
PHOON L Y, HASHIM H, MAT R, MUSTAFFA A A. Flash point prediction of tailor-made green diesel blends containing B5 palm oil biodiesel and alcohol[J]. Fuel, 2016,175:287-293. doi: 10.1016/j.fuel.2016.02.027
PRUGH R W. The relationship between flash point and LFL with application to hybrid mixtures[J]. Process Saf Prog, 2008,27(2):156-163. doi: 10.1002/(ISSN)1547-5913
PRAK D J L, COWART J S, TRULOVE P C. Density and viscosity from 293.15 to 373.15K, speed of sound and bulk modulus from 293.15 to 343.15 K, surface tension, and flash point of binary mixtures of bicyclohexyl and 1, 2, 3, 4-tetrahydronaphthalene or trans-decahydronaphthalene at 0.1MPa[J]. J Chem Eng Data, 2016,61(1):650-661. doi: 10.1021/acs.jced.5b00790
FLETCHER P D I, ROBERTS N A, URQUHART C. Solubility behavior, crystallization kinetics and pour point:A comparison of linear alkane and triacyl glyceride solute/solvent mixtures[J]. J Ind Eng Chem, 2016,34:382-389. doi: 10.1016/j.jiec.2015.12.012
GB 19147-2013, Automobile diesel fuels (V)[S].
BRANDENBURG A, WAPPLER E, KITA J, MOOS R. Miniaturized ceramic DSC device with strain gauge-based mass detection-first steps to realize a fully integrated DSC/TGA device[J]. Sens Actuators A, 2016,241:145-151. doi: 10.1016/j.sna.2016.02.011
JIN X, XU X D, ZHANG X S, YIN Y G. Determination of the PCM melting temperature rang using DSC[J]. Thermochim Acta, 2014,595:17-21. doi: 10.1016/j.tca.2014.09.004
Peipei CUI , Xin LI , Yilin CHEN , Zhilin CHENG , Feiyan GAO , Xu GUO , Wenning YAN , Yuchen DENG . Transition metal coordination polymers with flexible dicarboxylate ligand: Synthesis, characterization, and photoluminescence property. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2221-2231. doi: 10.11862/CJIC.20240234
Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Qiang Sun , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Li Wang . Recent progress on surface chemistry Ⅱ: Property and characterization. Chinese Chemical Letters, 2025, 36(1): 110100-. doi: 10.1016/j.cclet.2024.110100
Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
Teng-Yu Huang , Junliang Sun , De-Xian Wang , Qi-Qiang Wang . Recent progress in chiral zeolites: Structure, synthesis, characterization and applications. Chinese Chemical Letters, 2024, 35(12): 109758-. doi: 10.1016/j.cclet.2024.109758
Jianmin Jiao , Jiehao Yu , Xueqi Tian , Xiao-Yu Hu . TPE-embedded functional macrocycles: From structural design to photophysical property and application. Chinese Chemical Letters, 2025, 36(6): 111026-. doi: 10.1016/j.cclet.2025.111026
Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
Yulin Mao , Jingyu Ma , Jiecheng Ji , Yuliang Wang , Wanhua Wu , Cheng Yang . Crown aldoxime ethers: Their synthesis, structure, acid-catalyzed/photo-induced isomerization and adjustable guest binding. Chinese Chemical Letters, 2024, 35(11): 109927-. doi: 10.1016/j.cclet.2024.109927
Zhaodong WANG . In situ synthesis, crystal structure, and magnetic characterization of a trinuclear copper complex based on a multi-substituted imidazo[1,5-a]pyrazine scaffold. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 597-604. doi: 10.11862/CJIC.20240268
Huimin Luan , Qinming Wu , Jianping Wu , Xiangju Meng , Feng-Shou Xiao . Templates for the synthesis of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100252-100252. doi: 10.1016/j.cjsc.2024.100252
Hang Wang , Qi Wang , Chuan-De Wu . Continuous synthesis of ammonia. Chinese Journal of Structural Chemistry, 2025, 44(3): 100437-100437. doi: 10.1016/j.cjsc.2024.100437
Zhaojun Liu , Zerui Mu , Chuanbo Gao . Alloy nanocrystals: Synthesis paradigms and implications. Chinese Journal of Structural Chemistry, 2023, 42(11): 100156-100156. doi: 10.1016/j.cjsc.2023.100156
Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
Hui Jin , Qin Cai , Peiwen Liu , Yan Chen , Derong Wang , Weiping Zhu , Yufang Xu , Xuhong Qian . Multistep continuous flow synthesis of Erlotinib. Chinese Chemical Letters, 2024, 35(4): 108721-. doi: 10.1016/j.cclet.2023.108721
Zhao Li , Huimin Yang , Wenjing Cheng , Lin Tian . Recent progress of in situ/operando characterization techniques for electrocatalytic energy conversion reaction. Chinese Chemical Letters, 2024, 35(9): 109237-. doi: 10.1016/j.cclet.2023.109237
Caihong Mao , Yanfeng He , Xiaohan Wang , Yan Cai , Xiaobo Hu . Synthesis and molecular recognition characteristics of a tetrapodal benzene cage. Chinese Chemical Letters, 2024, 35(8): 109362-. doi: 10.1016/j.cclet.2023.109362
Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
Xiaoyu Chen , Jiahao Hu , Jingyi Lin , Haiyang Huang , Changqing Ye , Hongli Bao . Biisoindolylidene solvatochromic fluorophores: Synthesis and photophysical properties. Chinese Chemical Letters, 2025, 36(2): 109923-. doi: 10.1016/j.cclet.2024.109923
(a): PODE2; (b): PODE3; (c): PODE4; (d): PODE5
(a): PODE2; (b): PODE3; (c): PODE4; (d): PODE5
■: PODE2; ●: PODE3; ▲: PODE4; ▼: PODE5
■: PODE2; ●: PODE3; ▲: PODE4; ▼: PODE5
(a): PODE2; (b): PODE3; (c): PODE4; (d): PODE5