Efficient catalytic hydrogenation of alkyl levulinates to γ-valerolactone

2019 ◽  
Vol 21 (19) ◽  
pp. 5195-5200 ◽  
Author(s):  
Rosa Padilla ◽  
Mike S. B. Jørgensen ◽  
Márcio W. Paixão ◽  
Martin Nielsen
Keyword(s):  
Catalytic Hydrogenation ◽  
High Efficacy ◽  
Reaction Conditions ◽  
Alkyl Levulinates

Catalytic hydrogenation of alkyl levulinates to γ-valerolactone is achieved under mild reaction conditions employing pincer PNP-M complexes. High efficacy is demonstrated with TON's exceeding 9000. Furthermore, the feasibility of recycling is shown.

scholarly journals Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

2017 ◽  
Vol 13 ◽  
pp. 579-588 ◽  
Author(s):  
Jan Szabo ◽  
Julian Greiner ◽  
Gerhard Maas
Keyword(s):  
Crystal Structure ◽  
Carboxylic Acid ◽  
Nitrogen Atom ◽  
Catalytic Hydrogenation ◽  
Acid Chlorides ◽  
Reaction Conditions ◽  
Derivatives Of ◽  
Guanidinium Salts ◽  
Triazolium Salts

Depending on the reaction conditions, N,N’,N’’-tris(benzylamino)guanidinium salts can react with carboxylic acid chlorides to form either symmetrical N,N’,N’’-tris(N-acyl-N-benzylamido)guanidines 6 or mesoionic 4-amino-1,2,4-triazolium-3-hydrazinides 7. The latter were converted into 1,2,4-triazolium salts by protonation or methylation at the hydrazinide nitrogen atom. Neutral 1,2,4-triazoles 10 were obtained by catalytic hydrogenation of an N-benzyl derivative. Crystal structure analyses of a 4-benzylamino-1,2,4-triazolium-3-hydrazinide and of two derived 1,2,4-triazolium salts are presented.

Conversion of levulinic acid and alkyl levulinates into biofuels and high-value chemicals

2017 ◽  
Vol 19 (23) ◽  
pp. 5527-5547 ◽  
Author(s):  
Long Yan ◽  
Qian Yao ◽  
Yao Fu
Keyword(s):  
Catalytic Hydrogenation ◽  
Levulinic Acid ◽  
Comprehensive Review ◽  
Alkyl Levulinates

This article presents a comprehensive review of the catalytic hydrogenation of levulinic acid and alkyl levulinates into their derived biofuels and high-value chemicals, and includes the synthesis of levulinic acid and alkyl levulinates from biomass derivates.

Catalytic Hydrogenation with Amorphous and Crystalline Pd8 0Si2 0

1981 ◽  
Vol 8 ◽  
Author(s):  
Bill C. Giessen ◽  
Sabri S. Mahmoud ◽  
David A. Forsyth ◽  
Markus Hediger
Keyword(s):  
Double Bond ◽  
Catalytic Hydrogenation ◽  
Metallic Glasses ◽  
Hydrogen Deuterium Exchange ◽  
Reaction Conditions ◽  
Crystalline Phases ◽  
Hydrogenation Catalysts ◽  
Double Bond Migration ◽  
Hydrogenation Reactions ◽  
Hydrogen Deuterium

ABSTRACTSeveral metallic glasses in the form of ribbons were screened for activity as hydrogenation catalysts. Pd80Si20 and (Ni50Fe50)80B20 showed activity in reducing cyclohexene. Pd 80 Si20 was further examined for differences between the glassy and crystalline phases in the selectivity shown during hydrogenation reactions of n-hexenes, phenylethyne, α-pinene, and cyclododecene. No significant differences were found for catalytic selectivity in regard to cis-trans isomerization, double bond migration, and stereochemistry of addition under the reaction conditions used. Minor differences were observed in hydrogen-deuterium exchange.

scholarly journals Catalytic hydrogenation in the process of 2-((1-benzylpiperidin-4-yl) methyl)-5,6-dimethoxy-2,3-dihydroinden-1-one hydrochloride synthesis I. Catalyst screening and finding the optimal reaction conditions

2012 ◽  
Vol 14 (3) ◽  
pp. 38-47 ◽  
Author(s):  
Zrinka Mastelic Samardzic ◽  
Stanka Zrncevic
Keyword(s):  
Catalytic Hydrogenation ◽  
Hydrogen Pressure ◽  
Main Product ◽  
Catalyst Activity ◽  
Solvent Polarity ◽  
Catalyst Loading ◽  
Hydrogenation Rate ◽  
Reaction Conditions ◽  
Catalyst Screening ◽  
Optimal Reaction

1 Catalytic hydrogenation of 2-((1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydroinden- 1-one hydrochloride () to 2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydroinden- 1-one hydrochloride (2) was investigated in the batch-slurry reactor. The 5% Pt/C catalyst was chosen to search the optimal reaction conditions because of its higher catalytic activity compared to other catalysts used in the work. To investigate the catalyst activity, selectivity and stability, the effect of agitation speed, catalyst loading, solvent, temperature, hydrogen pressure and catalyst reuse were studied. The initial rate of hydrogenation increases with the increase of catalyst loading, with the temperature and solvent polarity, if alcohols were used as solvents. The hydrogenation rate decreases with higher hydrogen pressure and that was explained by competitive adsorption of both reactants. The results also indicate that 5% Pt/C is a promising catalyst for 1 hydrogenation because at relatively mild reaction conditions selectivity towards main product was high (98%) and catalyst maintains its activity during successive runs.

scholarly journals Alkyl Levulinates from Furfuryl Alcohol Using CT151 Purolite as Heterogenous Catalyst: Optimization, Purification, and Recycling

2021 ◽  
Vol 2 (3) ◽  
pp. 493-505
Author(s):  
Mattia Annatelli ◽  
Giacomo Trapasso ◽  
Lucrezia Lena ◽  
Fabio Aricò
Keyword(s):  
Reaction Time ◽  
Furfuryl Alcohol ◽  
Catalyst Activity ◽  
Scale Up ◽  
Acid Catalyst ◽  
Reaction Conditions ◽  
Short Reaction Time ◽  
Ethyl Levulinate ◽  
Heterogenous Catalyst ◽  
Alkyl Levulinates

Commercially available Purolite CT151 demonstrated to be an efficient acid catalyst for the synthesis of alkyl levulinates via alcoholysis of furfuryl alcohol (FA) at mild temperatures (80–120 °C) and short reaction time (5 h). Reaction conditions were first optimized for the synthesis of ethyl levulinate and then tested for the preparation of methyl-, propyl-, isopropyl-, butyl, sec-butyl- and allyl levulinate. Preliminary scale-up tests were carried out for most of the alkyl levulinates (starting from 5.0 g of FA) and the resulting products were isolated as pure by distillation in good yields (up to 63%). Furthermore, recycling experiments, conducted for the preparation of ethyl levulinate, showed that both the Purolite CT151 and the exceeding ethanol can be recovered and reused for four consecutive runs without any noticeable loss in the catalyst activity.

Catalytic Hydrogenation of Pyrylium Salts: A Convenient Route to Alkyl-Substituted Tetrahydropyrans

1986 ◽  
Vol 41 (4) ◽  
pp. 502-504 ◽  
Author(s):  
Gheorghe Mihai ◽  
Teodor-Silviu Balaban
Keyword(s):  
Catalytic Hydrogenation ◽  
Palladium Catalyst ◽  
Reaction Conditions ◽  
Pyrylium Salts ◽  
Convenient Route ◽  
High Yields

2,4.6-Trialkylpyrylium perchlorates afford in high yields by hydrogenation on palladium catalyst at room tem perature the corresponding all-dis-2,4.6-trialkyltetrahydropyrans, whereas other reaction conditions lead to mixtures of tetrahydropyrans and hydrogenolyzed products

Kinetic analysis of the catalytic hydrogenation of alkyl levulinates to γ-valerolactone

2017 ◽  
Vol 158 ◽  
pp. 545-551 ◽  
Author(s):  
Leila Negahdar ◽  
Mohammad G. Al-Shaal ◽  
Fabian J. Holzhäuser ◽  
Regina Palkovits
Keyword(s):  
Kinetic Analysis ◽  
Catalytic Hydrogenation ◽  
Alkyl Levulinates

scholarly journals Cinnamaldehyde hydrogenation using Au–Pd catalysts prepared by sol immobilisation

2018 ◽  
Vol 8 (6) ◽  
pp. 1677-1685 ◽  
Author(s):  
Stefano Cattaneo ◽  
Simon J. Freakley ◽  
David J. Morgan ◽  
Meenakshisundaram Sankar ◽  
Nikolaos Dimitratos ◽  
...  
Keyword(s):  
Catalytic Hydrogenation ◽  
Pd Nanoparticles ◽  
Catalytic Performance ◽  
Reaction Conditions ◽  
Pd Catalysts ◽  
Cinnamaldehyde Hydrogenation

We report the catalytic performance of Au–Pd nanoparticles prepared via a sol immobilisation technique for the catalytic hydrogenation of cinnamaldehyde under mild reaction conditions.

Synthesis, X-ray Crystal Structure and Antiestrogenic Activity of 17-Methyl-16,17-secoestra-1,3,5(10)-triene Derivatives

2005 ◽  
Vol 70 (1) ◽  
pp. 63-71 ◽  
Author(s):  
Marija N. Sakač ◽  
Dušan A. Miljković ◽  
Katarina M. Penov Gaši ◽  
Mirjana Popsavin ◽  
Olivera R. Klisurić ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Structural Analysis ◽  
Sodium Borohydride ◽  
Catalytic Hydrogenation ◽  
Chiral Center ◽  
Reaction Conditions ◽  
X Ray ◽  
Antiestrogenic Activity ◽  
Biological Tests

Starting from 3-(benzyloxy)-16-(hydroxyimino)-estra-1,3,5(10)-trien-17-one (1) several 17-methyl-16,17-secoestratriene derivatives were synthesized. In the first step of synthesis, hydroxyimino ketone 1 was transformed into 3-(benzyloxy)-16-(hydroxyimino)-17α-methylestra-1,3,5(10)-trien-17β-ol (2), the Beckmann fragmentation of which gave 3-(benzyloxy)-17-methyl-17-oxo-16,17-secoestra-1,3,5(10)-triene-16-nitrile (3a). Reduction of 3a with sodium borohydride yielded (17S)-3-(benzyloxy)-17-hydroxy-17-methyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile (4a), whose configuration at the newly formed chiral center was established by X-ray structural analysis. Catalytic hydrogenation of compound 3a under different reaction conditions yielded 3-hydroxy-17-methyl-17-oxo-16,17-secoestra-1,3,5(10)-triene-16-nitrile (3b) and 16-amino-17-methyl-16,17-secoestra-1,3,5(10)-triene-3,17-diol (6b). Biological tests in vivo of compounds 3b and 6b showed their moderate antiestrogenic activity.

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