Catalytic
ring-opening dehydration of tetrahydrofuran (THF), itself
a product of decarbonylation and reduction of biomass-derived furfural,
yields 1,3-butadiene, an important monomer in rubbers and elastomers.
It is demonstrated that dehydra-decyclization of THF with phosphorus-containing
siliceous self-pillared pentasil (SPP) or MFI structure exhibits high
selectivity to butadiene (85–99%) at both low (9%) and high
(89%) conversion of THF. High selectivity to pentadiene and hexadiene
was also obtained from 2-methyl-tetrahydrofuran and 2,5-dimethyl-tetrahydrofuran,
respectively, with phosphorus-containing, all-silica zeolites.
Catalytic hydrogenation of itaconic acid (obtained from glucose fermentation) yields 3-methyl-tetrahydrofuran (3-MTHF), which then undergoes catalytic dehydra-decyclization to isoprene. It is demonstrated that a one-pot cascade reaction converts itaconic acid to 3-MTHF at ∼80% yield with Pd−Re/C catalyst and 1000 psig H 2 . Subsequent gas-phase catalytic ring opening and dehydration of 3-MTHF with phosphorus-containing zeolites including P-BEA, P-MFI, and P-SPP (self-pillared pentasil) exhibits 90% selectivity to dienes (70% isoprene, 20% pentadienes) at 20−25% conversion.
An
important advance in fluid surface control was the amphiphilic
surfactant composed of coupled molecular structures (i.e., hydrophilic
and hydrophobic) to reduce surface tension between two distinct fluid
phases. However, implementation of simple surfactants has been hindered
by the broad range of applications in water containing alkaline earth
metals (i.e., hard water), which disrupt surfactant function and require
extensive use of undesirable and expensive chelating additives. Here
we show that sugar-derived furans can be linked with triglyceride-derived
fatty acid chains via Friedel–Crafts acylation within single
layer (SPP) zeolite catalysts. These alkylfuran surfactants independently
suppress the effects of hard water while simultaneously permitting
broad tunability of size, structure, and function, which can be optimized
for superior capability for forming micelles and solubilizing in water.
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