(Trans)acetalization Reactions for the Synthesis of Oligomeric Oxymethylene Dialkyl Ethers Catalyzed by Zeolite BEA25

Haltenort, Philipp; Lautenschütz, Ludger; Arnold, Ulrich; Sauer, Jörg

doi:10.1007/s11244-019-01188-9

Cited by 14 publications

(14 citation statements)

References 40 publications

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“…In the case of OMEs, transacetalization reactions have recently been proposed to modify their structures and to adjust fuel properties. 15 The reactions proceed readily in the presence of acidic catalysts as outlined in Scheme 1. Thus, not only chain lengths can be varied but also the end groups and a series of oxymethylene dialkyl ethers (OMDAEs) bearing various alkyl groups become accessible.…”

Section: Introductionmentioning

confidence: 99%

“…methoxyethoxymethane (R 1 = methyl, R 2 = ethyl). 15 Regarding branched OMDAEs, the synthesis of methoxymethyl ethers for the protection of hydroxyl ethers has been described. In 2008, the preparation of (2-ethylhexyloxy)methoxymethane ((2-EH)MM) from 2-ethylhexanol and DMM has been reported.…”

Section: Introductionmentioning

confidence: 99%

“…In previous work, zeolite BEA-25 proved to be a suitable acidic catalyst for such reactions and therefore, it has been chosen for this study. 15 The new compounds (2-ethylhexyloxy)propoxymethane ((2-EH)PM) and (2-ethylhexyloxy)butoxymethane ((2-EH)BM) have been characterized comprehensively and compared to the other derivatives. Furthermore, physico-chemical and fuel properties of the OMDAEs are compared to OMDMEs and alkanes with similar chain length.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of tailored oxymethylene ether (OME) fuels via transacetalization reactions

Drexler

Haltenort

Zevaco

et al. 2021

Sustainable Energy Fuels

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of tailored oxymethylene ether (OME) fuels via transacetalization reactions

Drexler

Haltenort

Zevaco

et al. 2021

Sustainable Energy Fuels

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“…( 4)) [28] or by transacetalization reactions, i.e., intermolecular exchange of FA units (Eq. ( 5)) [29]. Finally, a Flory-Schulz product distribution is adopted [30][31][32].…”

Section: Introductionmentioning

confidence: 99%

Continuous Synthesis of Oxymethylene Ether Fuels from Dimethyl Ether in a Heterogeneously Catalyzed Liquid Phase Process

Drexler

Haltenort

Arnold

et al. 2022

Chemie Ingenieur Technik

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Dedicated to Prof. Dr. Thomas Hirth on the occasion of his 60th birthdayOxymethylene ethers (OME) are an attractive alternative to fossil diesel fuel due to strongly reduced harmful emissions. An anhydrous, liquid phase production process based on dimethyl ether (DME) has been elaborated, which offers high selectivity and economic advantages. A catalyst screening for the reaction of DME with trioxane has been carried out. Highly active catalysts could be identified and further insight into the relationship between catalyst properties and catalytic performance could be gained. Furthermore, production in a continuous process could be realized, disclosing the influence of kinetics on OME formation and enabling a better understanding of the reaction mechanism.

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“…There are several synthetic strategies for the production of POMEs reported in the literature, and most of them incorporate formaldehyde as a reactant. ,,, Here, we report a conversion pathway to generate the computationally identified BB-POME n species through the reaction of a parent MM-POME 3–6 mixture with BuOH. This choice of reactants has the advantage of avoiding the use of formaldehyde in the transacetalization chemistry and the associated carbon loss and drying cost for anhydrous formaldehyde production, which is critical for sustainable and economical production of POMEs .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Butyl-Exchanged Polyoxymethylene Ethers as Renewable Diesel Blendstocks with Improved Fuel Properties

Arellano-Treviño

Bartholet

Bartling

et al. 2021

ACS Sustainable Chem. Eng.

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Methyl-terminated polyoxymethylene ethers (MM-POMEs), having the formula CH 3 O−(CH 2 O) n −CH 3 (n = 3−5), are a high-cetane, low-sooting group of oxygenates that have recently attracted attention as potential diesel blendstocks. Despite these attractive fuel properties, MM-POMEs have shortcomings due to their low energy density and high water solubility. Guided by a computational fuel property assessment for POMEs with longer end-groups, the most promising improvements in the desired compression ignition fuel properties were observed for butyl-terminated POMEs. Here, an acid-catalyzed transacetalization reaction was developed to exchange the methyl end-groups of MM-POMEs (n = 3−6) with butyl end-groups. The reaction utilizes an ion-exchange resin as the acid catalyst at mild reaction conditions of 60 °C and atmospheric pressure. Approximately 100 mL of butyl-exchanged POMEs in the diesel boiling range were produced, enabling laboratory-scale fuel property testing. The butylterminated POME mixture possesses the advantaged fuel properties of the parent MM-POMEs (low-soot, high-cetane) while exhibiting improved energy density (lower heating value (LHV) of 30 MJ/kg) and substantially reduced water solubility (7.3 g/L) compared to the parent MM-POME mixture (LHV of 19 MJ/kg , water solubility of 258 g/L).

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(Trans)acetalization Reactions for the Synthesis of Oligomeric Oxymethylene Dialkyl Ethers Catalyzed by Zeolite BEA25

Cited by 14 publications

References 40 publications

Synthesis of tailored oxymethylene ether (OME) fuels via transacetalization reactions

Synthesis of tailored oxymethylene ether (OME) fuels via transacetalization reactions

Continuous Synthesis of Oxymethylene Ether Fuels from Dimethyl Ether in a Heterogeneously Catalyzed Liquid Phase Process

Synthesis of Butyl-Exchanged Polyoxymethylene Ethers as Renewable Diesel Blendstocks with Improved Fuel Properties

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