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Journal articles on the topic '5-chloromethyl furfural'

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Author: Grafiati

Published: 10 December 2022

Last updated: 28 January 2023

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1

Bizet, Boris, Christian H. Hornung, Thomas M. Kohl, and John Tsanaktsidis. "Synthesis of Imines and Amines from Furfurals Using Continuous Flow Processing." Australian Journal of Chemistry 70, no. 10 (2017): 1069. http://dx.doi.org/10.1071/ch17036.

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A simple procedure for the condensation of the bio-derived furfurals, 5-(methyl)furfural (MF) and 5-(chloromethyl)furfural (CMF), with primary amines is described herein. The experiments were conducted in both batch and flow conditions, with reaction times as short as 60 s. Moderately high temperatures were demonstrated to be suitable for the condensation reaction of MF in a few minutes whereas milder conditions and longer reaction times were necessary for CMF. Under these conditions the amine did not react with the methyl-chlorine group, leaving a very reactive site after condensation.

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2

Kohl, T. M., B. Bizet, P. Kevan, C. Sellwood, J. Tsanaktsidis, and C. H. Hornung. "Efficient synthesis of 5-(chloromethyl)furfural (CMF) from high fructose corn syrup (HFCS) using continuous flow processing." Reaction Chemistry & Engineering 2, no. 4 (2017): 541–49. http://dx.doi.org/10.1039/c7re00039a.

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3

Zuo, Miao, Zheng Li, Yetao Jiang, Xing Tang, Xianhai Zeng, Yong Sun, and Lu Lin. "Correction: Green catalytic conversion of bio-based sugars to 5-chloromethyl furfural in deep eutectic solvent, catalyzed by metal chlorides." RSC Advances 6, no. 40 (2016): 33492. http://dx.doi.org/10.1039/c6ra90032a.

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4

Mascal, Mark, and Saikat Dutta. "Synthesis of ranitidine (Zantac) from cellulose-derived 5-(chloromethyl)furfural." Green Chemistry 13, no. 11 (2011): 3101. http://dx.doi.org/10.1039/c1gc15537g.

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5

Dutta, Saikat, and Mark Mascal. "Novel Pathways to 2,5-Dimethylfuran via Biomass-Derived 5-(Chloromethyl)furfural." ChemSusChem 7, no. 11 (September 5, 2014): 3028–30. http://dx.doi.org/10.1002/cssc.201402702.

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6

Mascal, Mark, and Edward B Nikitin. "Dramatic Advancements in the Saccharide to 5-(Chloromethyl)furfural Conversion Reaction." ChemSusChem 2, no. 9 (September 21, 2009): 859–61. http://dx.doi.org/10.1002/cssc.200900136.

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7

Bhat, Navya Subray, Nivedha Vinod, Sharath Bandibairanahalli Onkarappa, and Saikat Dutta. "Hydrochloric acid-catalyzed coproduction of furfural and 5-(chloromethyl)furfural assisted by a phase transfer catalyst." Carbohydrate Research 496 (October 2020): 108105. http://dx.doi.org/10.1016/j.carres.2020.108105.

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8

Dutta, Saikat, Linglin Wu, and Mark Mascal. "Production of 5-(chloromethyl)furan-2-carbonyl chloride and furan-2,5-dicarbonyl chloride from biomass-derived 5-(chloromethyl)furfural (CMF)." Green Chemistry 17, no. 7 (2015): 3737–39. http://dx.doi.org/10.1039/c5gc00936g.

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Biomass-derived CMF is oxidized to the acid chloride CMFCC in a single step using inexpensive t-butyl hypochlorite. Likewise, DFF, also a CMF derivative, is oxidized directly to the diacid chloride FDCC. The products are platforms for a variety of chemical derivatives of carbohydrates.

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9

Mascal, Mark. "5-(Chloromethyl)furfural (CMF): A Platform for Transforming Cellulose into Commercial Products." ACS Sustainable Chemistry & Engineering 7, no. 6 (March 5, 2019): 5588–601. http://dx.doi.org/10.1021/acssuschemeng.8b06553.

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10

Salim, Kunnummal Mangott Muhammed, Aranhikkal Shamsiya, and Bahulayan Damodaran. "Green Synthesis of Fluorescent Peptidomimetic Triazoles from Biomass-Derived 5-(Chloromethyl)furfural." ChemistrySelect 3, no. 39 (October 24, 2018): 11141–46. http://dx.doi.org/10.1002/slct.201802310.

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11

Breeden, S. W., J. H. Clark, T. J. Farmer, D. J. Macquarrie, J. S. Meimoun, Y. Nonne, and J. E. S. J. Reid. "Microwave heating for rapid conversion of sugars and polysaccharides to 5-chloromethyl furfural." Green Chem. 15, no. 1 (2013): 72–75. http://dx.doi.org/10.1039/c2gc36290b.

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12

Chang, Fei, Wan-Hsuan Hsu, and Mark Mascal. "Synthesis of anti-inflammatory furan fatty acids from biomass-derived 5-(chloromethyl)furfural." Sustainable Chemistry and Pharmacy 1 (June 2015): 14–18. http://dx.doi.org/10.1016/j.scp.2015.09.002.

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13

Brasholz, Malte, Karin von Känel, Christian H. Hornung, Simon Saubern, and John Tsanaktsidis. "Highly efficient dehydration of carbohydrates to 5-(chloromethyl)furfural (CMF), 5-(hydroxymethyl)furfural (HMF) and levulinic acid by biphasic continuous flow processing." Green Chemistry 13, no. 5 (2011): 1114. http://dx.doi.org/10.1039/c1gc15107j.

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14

Antonyraj, Churchil A., Amal J. Chennattussery, and Ajit Haridas. "5‐(Chloromethyl)furfural production from glucose: A pioneer kinetic model development exploring the mechanism." International Journal of Chemical Kinetics 53, no. 7 (March 16, 2021): 825–33. http://dx.doi.org/10.1002/kin.21485.

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15

Miao, Haoqian, Huitao Ling, Nikolay Shevchenko, and Mark Mascal. "Generation of Organozinc Nucleophiles Based on the Biomass-Derived Platform Molecule 5-(Chloromethyl)furfural." Organometallics 40, no. 23 (November 15, 2021): 3952–57. http://dx.doi.org/10.1021/acs.organomet.1c00528.

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16

Mascal, Mark, and Saikat Dutta. "Synthesis of the natural herbicide δ-aminolevulinic acid from cellulose-derived 5-(chloromethyl)furfural." Green Chem. 13, no. 1 (2011): 40–41. http://dx.doi.org/10.1039/c0gc00548g.

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17

Chang, Fei, Saikat Dutta, James J. Becnel, Alden S. Estep, and Mark Mascal. "Synthesis of the Insecticide Prothrin and Its Analogues from Biomass-Derived 5-(Chloromethyl)furfural." Journal of Agricultural and Food Chemistry 62, no. 2 (January 3, 2014): 476–80. http://dx.doi.org/10.1021/jf4045843.

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18

Dai, Lei, Ye Qiu, Yuan-Yuan Xu, and Song Ye. "Biomass Transformation of Cellulose via N-Heterocyclic Carbene-Catalyzed Umpolung of 5-(Chloromethyl)furfural." Cell Reports Physical Science 1, no. 6 (June 2020): 100071. http://dx.doi.org/10.1016/j.xcrp.2020.100071.

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19

Zhang, Ximing, Necla Mine Eren, Thomas Kreke, Nathan S. Mosier, Abigail S. Engelberth, and Gozdem Kilaz. "Concentrated HCl Catalyzed 5-(Chloromethyl)furfural Production from Corn Stover of Varying Particle Sizes." BioEnergy Research 10, no. 4 (July 25, 2017): 1018–24. http://dx.doi.org/10.1007/s12155-017-9860-5.

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20

Howard, Joshua, Darryn W. Rackemann, Zhanying Zhang, Lalehvash Moghaddam, John P. Bartley, and William O. S. Doherty. "Effect of pretreatment on the formation of 5-chloromethyl furfural derived from sugarcane bagasse." RSC Advances 6, no. 7 (2016): 5240–48. http://dx.doi.org/10.1039/c5ra20203e.

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21

Mascal, Mark, and Saikat Dutta. "ChemInform Abstract: Synthesis of Ranitidine (Zantac) (VIII) from Cellulose-Derived 5-(Chloromethyl)furfural (I)." ChemInform 43, no. 14 (March 8, 2012): no. http://dx.doi.org/10.1002/chin.201214096.

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22

Breeden, S. W., J. H. Clark, T. J. Farmer, D. J. Macquarrie, J. S. Meimoun, Y. Nonne, and J. E. S. J. Reid. "ChemInform Abstract: Microwave Heating for Rapid Conversion of Sugars and Polysaccharides to 5-Chloromethyl Furfural." ChemInform 44, no. 19 (April 18, 2013): no. http://dx.doi.org/10.1002/chin.201319098.

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23

Mascal, Mark, and Edward B. Nikitin. "High-yield conversion of plant biomass into the key value-added feedstocks 5-(hydroxymethyl)furfural, levulinic acid, and levulinic esters via5-(chloromethyl)furfural." Green Chem. 12, no. 3 (2010): 370–73. http://dx.doi.org/10.1039/b918922j.

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24

Chen, Binglin, Yunchao Feng, Renjie Huang, Shibo Yang, Zheng Li, Jonathan Sperry, Shuliang Yang, et al. "Efficient synthesis of the liquid fuel 2,5-dimethylfuran from biomass derived 5-(chloromethyl)furfural at room temperature." Applied Catalysis B: Environmental 318 (December 2022): 121842. http://dx.doi.org/10.1016/j.apcatb.2022.121842.

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25

Zuo, Miao, Zheng Li, Yetao Jiang, Xing Tang, Xianhai Zeng, Yong Sun, and Lu Lin. "Green catalytic conversion of bio-based sugars to 5-chloromethyl furfural in deep eutectic solvent, catalyzed by metal chlorides." RSC Advances 6, no. 32 (2016): 27004–7. http://dx.doi.org/10.1039/c6ra00267f.

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5-Chloromethylfurfural (5-CMF) was effectively prepared from fructose and other carbohydrates in a biphasic reaction system, which was composed of methyl isobutyl ketone (MIBK) and deep eutectic solvent (DES) with catalyst of AlCl₃·6H₂O.

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26

Lane, David R., Mark Mascal, and Pieter Stroeve. "Experimental studies towards optimization of the production of 5-(chloromethyl)furfural (CMF) from glucose in a two-phase reactor." Renewable Energy 85 (January 2016): 994–1001. http://dx.doi.org/10.1016/j.renene.2015.07.032.

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27

Mascal, Mark. "5-(Chloromethyl)furfural is the New HMF: Functionally Equivalent But More Practical in Terms of its Production From Biomass." ChemSusChem 8, no. 20 (September 16, 2015): 3391–95. http://dx.doi.org/10.1002/cssc.201500940.

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28

Budarin, Vitaliy L., James H. Clark, Jonatan Henschen, Thomas J. Farmer, Duncan J. Macquarrie, Mark Mascal, Gundibasappa K. Nagaraja, and Tabitha H. M. Petchey. "Processed Lignin as a Byproduct of the Generation of 5-(Chloromethyl)furfural from Biomass: A Promising New Mesoporous Material." ChemSusChem 8, no. 24 (November 25, 2015): 4172–79. http://dx.doi.org/10.1002/cssc.201501319.

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29

Onkarappa, Sharath Bandibairanahalli, and Saikat Dutta. "Phase Transfer Catalyst Assisted One‐Pot Synthesis of 5‐(Chloromethyl)furfural from Biomass‐Derived Carbohydrates in a Biphasic Batch Reactor." ChemistrySelect 4, no. 25 (July 2019): 7502–6. http://dx.doi.org/10.1002/slct.201901347.

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30

Arnaud, Sacha Pérocheau, Linglin Wu, Maria-Angelica Wong Chang, James W. Comerford, Thomas J. Farmer, Maximilian Schmid, Fei Chang, Zheng Li, and Mark Mascal. "New bio-based monomers: tuneable polyester properties using branched diols from biomass." Faraday Discussions 202 (2017): 61–77. http://dx.doi.org/10.1039/c7fd00057j.

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A family of monomers, including 2,5-hexandiol, 2,7-octandiol, 2,5-furandicarboxylic acid (FDCA), terephthalic acid (TA), and branched-chain adipic and pimelic acid derivatives, all find a common derivation in the biomass-derived platform molecule 5-(chloromethyl)furfural (CMF). The diol monomers, previously little known to polymer chemistry, have been combined with FDCA and TA derivatives to produce a range of novel polyesters. It is shown that the use of secondary diols leads to polymers with higher glass transition temperatures (T_g) than those prepared from their primary diol equivalents. Two methods of polymerisation were investigated, the first employing activation of the aromatic diacids via the corresponding diacid chlorides and the second using a transesterification procedure. Longer chain diols were found to be more reactive than the shorter chain alternatives, generally giving rise to higher molecular weight polymers, an effect shown to be most pronounced when using the transesterification route. Finally, novel diesters with high degrees of branching in their hydrocarbon chains are introduced as potential monomers for possible low surface energy materials applications.

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31

Kundu, Chandan, Saheli Biswas, Mahmud Arman Kibria, and Sankar Bhattacharya. "Thermochemical Conversion of Untreated and Pretreated Biomass for Efficient Production of Levoglucosenone and 5-Chloromethylfurfural in the Presence of an Acid Catalyst." Catalysts 12, no. 2 (February 9, 2022): 206. http://dx.doi.org/10.3390/catal12020206.

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Levoglucosenone (LGO) and 5-chloromethyl furfural (5-CMF) are two bio-based platform chemicals with applications in medicines, green solvents, fuels, and the polymer industry. This study demonstrates the one-step thermochemical conversion of raw and pretreated (delignified) biomass to highly-valuable two platform chemicals in a fluidized bed reactor. Hydrochloric acid gas is utilized to convert biomass thermochemically. The addition of hydrochloric acid gas facilitates the formation of LGO and CMF. Acid gas reacts with biomass to form 5-CMF, which acts as a catalyst to increase the concentration of LGO in the resulting bio-oil. The presence of higher cellulose content in delignified biomass significantly boosts the synthesis of both platform chemicals (LGO and CMF). GC-MS analysis was used to determine the chemical composition of bio-oil produced from thermal and thermochemical conversion of biomass. At 350 °C, the maximum concentration of LGO (27.70 mg/mL of bio-oil) was achieved, whereas at 400 °C, the highest concentration of CMF (19.24 mg/mL of bio-oil) was obtained from hardwood-delignified biomass. The findings suggest that 350 °C is the optimal temperature for producing LGO and 400 °C is optimal for producing CMF from delignified biomass. The secondary cracking process is accelerated by temperatures over 400 °C, resulting in a low concentration of the target platform chemicals. This work reveals the simultaneous generation of LGO and CMF, two high-value commercially relevant biobased compounds.

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32

Gao, Wenhua, Yiqun Li, Zhouyang Xiang, Kefu Chen, Rendang Yang, and Dimitris Argyropoulos. "Correction: Gao, W., et al. Efficient One-Pot Synthesis of 5-Chloromethyl-furfural (CMF) from Carbohydrates in Mild Biphasic Systems. Molecules 2013, 18, 7675-7685." Molecules 19, no. 1 (January 22, 2014): 1370–74. http://dx.doi.org/10.3390/molecules19011370.

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33

Park, Dongwoon, Soohyeon Lee, Jinsung Kim, Ga Yeong Ryu, and Young‐Woong Suh. "5‐(Chloromethyl)Furfural as a Potential Source for Continuous Hydrogenation of 5‐(Hydroxymethyl)Furfural to 2,5‐Bis(Hydroxymethyl)Furan." ChemPlusChem, August 23, 2022. http://dx.doi.org/10.1002/cplu.202200271.

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34

Park, Dongwoon, Soohyeon Lee, Jinsung Kim, Ga Yeong Ryu, and Young‐Woong Suh. "5‐(Chloromethyl)Furfural as a Potential Source for Continuous Hydrogenation of 5‐(Hydroxymethyl)Furfural to 2,5‐Bis(Hydroxymethyl)Furan." ChemPlusChem, August 24, 2022. http://dx.doi.org/10.1002/cplu.202200272.

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35

Miao, Haoqian, Nikolay Shevchenko, Andrew L. Otsuki, and Mark Mascal. "Diversification of the Renewable Furanic Platform via 5‐(Chloromethyl)furfural‐Based Carbon Nucleophiles." ChemSusChem, October 5, 2020. http://dx.doi.org/10.1002/cssc.202001718.

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36

Ling, Huitao, Haoqian Miao, Zhiling Cao, and Mark Mascal. "Electrochemical Incorporation of Electrophiles into the Biomass‐derived Platform Molecule 5‐(Chloromethyl)furfural (CMF)." ChemSusChem, December 16, 2022. http://dx.doi.org/10.1002/cssc.202201787.

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37

Chen, Binglin, Zheng Li, Yunchao Feng, Weiwei Hao, Yong Sun, Xing Tang, Xianhai Zeng, and Lu Lin. "Green Process for 5‐(Chloromethyl)furfural Production from Biomass in Three‐Constituent Deep Eutectic Solvent." ChemSusChem, January 5, 2021. http://dx.doi.org/10.1002/cssc.202002631.

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38

Chen, Binglin, Yunchao Feng, Renjie Huang, Shibo Yang, Zheng Li, Jonathan Sperry, Shuliang Yang, et al. "Efficient Synthesis of the Liquid Fuel 2,5-Dimethylfuran from Biomass Derived 5-(Chloromethyl)Furfural at Room Temperature." SSRN Electronic Journal, 2022. http://dx.doi.org/10.2139/ssrn.4141616.

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39

Chen, Binglin, Yunchao Feng, Sen Ma, Weizhen Xie, Guihua Yan, Zheng Li, Jonathan Sperry, et al. "One-pot synthesis of 2,5-bis(hydroxymethyl)furan from biomass derived 5-(chloromethyl)furfural in high yield." Journal of Energy Chemistry, October 2022. http://dx.doi.org/10.1016/j.jechem.2022.10.005.

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40

Rojahn, Patrick, Krishna D. P. Nigam, and Frank Schael. "Experimental study and kinetic modeling of continuous flow conversion of fructose to 5-(chloromethyl)furfural using micro- and millistructured coiled flow inverter." Chemical Engineering Journal, July 2022, 138243. http://dx.doi.org/10.1016/j.cej.2022.138243.

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41

Lakmini, Loku Mannage N., Athukoralalage Don K. Deshan, Hong Duc Pham, William Doherty, Darryn Rackemann, Deepak P. Dubal, and Lalehvash Moghaddam. "High carbon utilization: 5-(Chloromethyl)furfural (CMF) production from rice by-products and transformation of CMF residues into Li-ion energy storage systems." Journal of Cleaner Production, September 2022, 134082. http://dx.doi.org/10.1016/j.jclepro.2022.134082.

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