100-72-1Relevant articles and documents
Modeling aqueous-phase hydrodeoxygenation of sorbitol over Pt/SiO 2-Al2O3
Moreno, Brian M.,Li, Ning,Lee, Jechan,Huber, George W.,Klein, Michael T.
, p. 23769 - 23784 (2013)
In this paper, we investigated the effects of temperature, hydrogen partial pressure, and sorbitol concentration on the aqueous-phase hydrodeoxygenation (APHDO) of sorbitol over a bifunctional 4 wt% Pt/SiO2-Al 2O3 catalyst in a trickle bed reactor. APHDO involves four fundamental reactions: (1) hydrogenation; (2) dehydration; (3) C-C bond cleavage by dehydrogenation and decarbonylation; and (4) C-C bond cleavage by dehydrogenation and retro-aldol condensation. The main deoxygenation routes are decarbonylation and alcohol dehydration. Retro-aldol condensation plays a critical role in reducing the carbon number of the products. The key products in this system are C1-C6 n-alkanes, primary and secondary alcohols, and carbon dioxide. As shown in this paper, the reaction conditions can dramatically change the product selectivity for APHDO of biomass-derived feedstocks (e.g., sorbitol). A sorbitol hydrodeoxygenation reaction network was generated that predicts all of the 43 experimentally measured species. The reaction network consists of 4804 reactions and produces a total of 1178 distinct chemical species. The associated material balance equations were solved numerically to model the experimentally observed species as a function of temperature, concentration, and pressure. The model concentrations fit well the experimentally measured values, demonstrating that the model was accurately able to model the reaction families and capture the salient features of the experimental observations. The trend observed in this paper can be used for the optimization of reactors and new catalysts to selectively make targeted products by hydrodeoxygenation of biomass-derived feedstocks.
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Eliel,E.L. et al.
, p. 2441 - 2447 (1965)
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Caprolactam from renewable resources: Catalytic conversion of 5-hydroxymethylfurfural into caprolactone
Buntara, Teddy,Noel, Sebastien,Phua, Pim Huat,Melian-Cabrera, Ignacio,De Vries, Johannes G.,Heeres, Hero J.
, p. 7083 - 7087 (2011)
Renewable nylon: 5-Hydroxymethylfurfural (HMF), which can be obtained from renewable resources such as D-fructose, was converted into caprolactone with very good overall selectivity in only three steps. The new route involves two hydrogenation steps to obtain 1,6-hexanediol, which was oxidatively cyclized to caprolactone, and then converted into caprolactam. Copyright
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Pattison
, p. 3455 (1957)
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Hydroformylation and hydroalkylcarbonylation of 3,4-dihydro[2H]pyran catalysed by Co2(CO)8 under syngas conditions
Arias, Jose L.,Sharma, Pankaj,Cabrera, Armando,Beristain, Fernando,Sampere, Rafael,Arizmendi, Cesar
, p. 787 - 792 (2013)
In the cobalt-catalysed hydroformylation of 3,4-dihydro[2H]pyran, the influence of different reaction parameters such as time, pressure, triphenylphosphine addition, catalyst and substrate concentration has been investigated. 2-formyl-tetrahydropyran, tetrahydropyran and a hydroalkylcarbonylation product were the main reaction products. The selectivity towards 2-formyl-tetrahydropyran formation is favoured at constant catalyst and substrate concentration. The coordination of the pyran's oxygen to the cobalt atom seems to be an important intermediate for the formation of 2-formyl-tetrahydropyran. Different substrate or catalyst concentrations promote the formation of other reduced products. The addition of triphenylphosphine to the catalyst leads to a less active species, which decreases the yield and promotes the hydroalkylcarbonylation reaction.
Rhenium-catalyzed deoxydehydration of renewable triols derived from sugars
Wozniak, Bartosz,Li, Yuehui,Tin, Sergey,De Vries, Johannes G.
, p. 4433 - 4437 (2018)
An efficient method for the catalytic deoxydehydration of renewable triols, including those obtained from 5-HMF, is described. The corresponding unsaturated alcohols were obtained in good yields using simple rhenium(vii)oxide under neat conditions and ambient atmosphere at 165 °C.
PROCESS FOR PRODUCING 1,6-HEXANEDIOL
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Page/Page column 0082; 0083, (2016/06/28)
Disclosed herein are processes for producing 1,6-hexanediol. In one embodiment, the process comprises a step of contacting 3,4-dihydro-2H-pyran-2-carbaldehyde, a solvent, and hydrogen in the presence of a catalyst at a reaction temperature between about 0° C. and about 120° C. at a pressure and for a reaction time sufficient to form a product mixture comprising 1,6-hexanediol. In one embodiment, the catalyst comprises a metal M1, a metal M2 or an oxide of M2, and a support, wherein M1 is Rh, Ir, Ni, Pd, or Pt, and M2 is Mo, W, or Re; or M1 is Cu and M2 is Ni, Mn, or W.
