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).
Lewis-Pair-Mediated Selective Dimerization and Polymerization of Lignocellulose-Based β-Angelica Lactone into Biofuel and Acrylic Bioplastic
Hong, Miao,Wang, Xiao-Jun
supporting information, p. 2664 - 2668 (2020/01/24)
This contribution reports an unprecedentedly efficient dimerization and the first successful polymerization of lignocellulose-based β-angelica lactone (β-AL) by utilizing a selective Lewis pair (LP) catalytic system, thereby establishing a versatile bio-refinery platform wherein two products, including a dimer for high-quality gasoline-like biofuel (C8–C9 branched alkanes, yield=87 %) and a heat- and solvent-resistant acrylic bioplastic (Mn up to 26.0 kg mol?1), can be synthesized from one feedstock by one catalytic system. The underlying reason for exquisite selectivity of the LP catalytic system toward dimerization and polymerization was explored mechanistically.
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.
