591-11-7Relevant articles and documents
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Ogibin et al.
, (1976)
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Synthesis of renewable diesel with 2-methylfuran and angelica lactone derived from carbohydrates
Wang, Wei,Li, Ning,Li, Shanshan,Li, Guangyi,Chen, Fang,Sheng, Xueru,Wang, Aiqin,Wang, Xiaodong,Cong, Yu,Zhang, Tao
, p. 1218 - 1223 (2016)
Diesel and jet fuel range branched alkanes were first synthesized by the combination of hydroxyalkylation/alkylation (HAA) of 2-methylfuran with angelica lactone and subsequent hydrodeoxygenation. Compared with the previous ethyl levulinate route, the angelica lactone route exhibited evident advantages at higher HAA reactivity.
Synthesis of diastereo- and enantiomerically pure anti-3-methyl-1,4- pentanediol via lipase catalysed acylation
Lindstroem, Mona,Hedenstroem, Erik,Bouilly, Sandrine,Velonia, Kelly,Smonou, Ioulia
, p. 1355 - 1360 (2005)
Racemic trans-4,5-dimethylhydrofuran-2(3H)-one was synthesised from 5-methyl-furan-2(3H)-one, (α-angelica lactone). The key reaction in the synthesis was the 1,4-conjugate addition of an organocuprate to 5-methylfuran-2(5H)-one (β-angelica lactone). Different types of organocuprates were tested with the highest anti:syn ratio of 99.4:0.6 being obtained by the use of a Gilman organocuprate reagent. The enantioselective acylation of racemic 3-methyl-pentan-1,4-diol, catalysed by a variety of lipases in organic media, was investigated. The highest enantioselectivity (E >400) was obtained when Novozyme 435 was used as the catalyst at a water activity of aw ~ 0. Thus, both enantiomers, (3S,4R)- and (3R,4S)-3-methyl- pentan-1,4-diol, were obtained in very high diastereomeric (>99% de) and enantiomeric purities (>99.8% and >97.4% ee, respectively).
Scalable synthesis and polymerisation of a β-angelica lactone derived monomer
De Vries, Johannes G.,Dell'Acqua, Andrea,Kirchhecker, Sarah,Stadler, Bernhard M.,Tin, Sergey
supporting information, p. 5267 - 5273 (2020/09/17)
Bio-based levulinic acid is easily ring-closed to α-angelica lactone (α-AL). α-AL can be isomerized to the conjugated β-AL under the influence of base, but since this is an equilibrium mixture it is very hard to devise a scalable process that would give pure β-AL. This problem was circumvented by distilling the equilibrium mixture to obtain a 90?:?10 mixture of β-and α-AL in 88% yield. This mixture was used for Diels-Alder reactions on 3 terpenes and on cyclopentadiene in up to 100 g scale. The latter DA adduct was subjected to a ROMP reaction catalysed by the Grubbs II catalyst. The resulting polymer has some similarities to poly-norbornene but is more polar. The polymer can be processed into films with very good transparency.
Conversion of levulinic acid to ethyl levulinate using tin modified silicotungstic acid supported on Ta2O5
Ganji, Parameswaram,Roy, Sounak
, (2019/11/05)
Tin modified silicotungstic acid (STA) deposited on Ta2O5 was explored as suitable catalyst for the conversion of levulinic acid to ethyl levulinate. The microwave synthesized catalysts of varying amounts of STA were characterised by N2 adsorption, powder XRD, FT-IR, FE-SEM, XPS, pyridine-FT-IR, TGA-DTA and NH3-TPD. Among the synthesized catalysts, 50% Sn2STA/Ta2O5 catalyst exhibited excellent catalytic activity for the esterification of levulinic acid providing 78% of ethyl levulinate yield and stable recyclability up to three cycles. The rate of esterification was 6.6 × 10?3 mol/g/min, which is significantly higher compared to reported values in the open literature. Mechanistic investigations revealed that the high catalytic activity was influenced by the presence of appropriate Br?nsted acid sites, surface area and porosity.