13360-61-7Relevant articles and documents
Effective deoxygenation of fatty acids over Ni(OAc)2 in the absence of H2 and solvent
Li, Wenjing,Gao, Yongjun,Yao, Siyu,Ma, Ding,Yan, Ning
, p. 4198 - 4205 (2015)
Different metal acetate salts were systematically examined for the catalytic deoxygenation of stearic acid in the absence of H2 and solvent for the first time. Ni(OAc)2 exhibited the highest activity with 62% yield achieved at 350°C for 4.5 h with only 1 mol% (0.2 wt%) of the catalyst. Even with 0.25 mol% (0.05 wt%) catalyst, around 28% yield was achieved within 2 h at 350°C with 89% selectivity to C17 hydrocarbons. The activity based on C17 yields per Ni was 14.5 mol mol-1 h-1, considerably higher than that in previous reports. The catalytically active species were identified to be in situ generated Ni nanoparticles (8-10 nm) formed from the decomposition of the metal precursor with stearic acid as a stabilizer. A new reaction pathway of alkane formation from stearic acid via anhydride intermediate decarbonylation under an inert gas atmosphere was proposed. The excellent stability of the catalyst was demonstrated by re-adding a substrate to the system, during which the activity remained constant through four consecutive runs. The novel catalytic system was found to be applicable to a range of fatty acids and triglycerides with varying activities.
Anodic Cyclization of Unsaturated α-Stannyl Ethers. Termination by Bromide derived from Dibromomethane
Yoshida, Jun-ichi,Takada, Kazunori,Ishichi, Yuji,Isoe, Sachihiko
, p. 2361 - 2362 (1994)
Anodic oxidation of unsaturated α-stannyl ethers in Bu4NClO4-CH2Br2 results in effective cyclization and the introduction of bromide into one of the original olefinic carbons; a mechanism involving the coupling between the cyclized carbocation and Br- generated by cathodic reduction of CH2Br2 is suggested.
Alkene synthesis by photocatalytic chemoenzymatically compatible dehydrodecarboxylation of carboxylic acids and biomass
Nguyen, Vu T.,Nguyen, Viet D.,Haug, Graham C.,Dang, Hang T.,Jin, Shengfei,Li, Zhiliang,Flores-Hansen, Carsten,Benavides, Brenda S.,Arman, Hadi D.,Larionov, Oleg V.
, p. 9485 - 9498 (2019/10/11)
Direct conversion of renewable biomass and bioderived chemicals to valuable synthetic intermediates for organic synthesis and materials science applications by means of mild and chemoselective catalytic methods has largely remained elusive. Development of artificial catalytic systems that are compatible with enzymatic reactions provides a synergistic solution to this enduring challenge by leveraging previously unachievable reactivity and selectivity modes. We report herein a dual catalytic dehydrodecarboxylation reaction that is enabled by a crossover of the photoinduced acridine-catalyzed O-H hydrogen atom transfer (HAT) and cobaloxime-catalyzed C-H-HAT processes. The reaction produces a variety of alkenes from readily available carboxylic acids. The reaction can be embedded in a scalable triple-catalytic cooperative chemoenzymatic lipase-acridine-cobaloxime process that allows for direct conversion of plant oils and biomass to long-chain terminal alkenes, precursors to bioderived polymers.
An Engineered Self-Sufficient Biocatalyst Enables Scalable Production of Linear α-Olefins from Carboxylic Acids
Lu, Chen,Shen, Fenglin,Wang, Shuaibo,Wang, Yuyang,Liu, Juan,Bai, Wen-Ju,Wang, Xiqing
, p. 5794 - 5798 (2018/06/01)
Fusing the decarboxylase OleTJE and the reductase domain of P450BM3 creates a self-sufficient protein, OleT-BM3R, which is able to efficiently catalyze oxidative decarboxylation of carboxylic acids into linear α-olefins (LAOs) under mild aqueous conditions using O2 as the oxidant and NADPH as the electron donor. The compatible electron transfer system installed in the fusion protein not only eliminates the need for auxiliary redox partners, but also results in boosted decarboxylation reactivity and broad substrate scope. Coupled with the phosphite dehydrogenase-based NADPH regeneration system, this enzymatic reaction proceeds with improved product titers of up to 2.51 g L-1 and volumetric productivities of up to 209.2 mg L-1 h-1 at low catalyst loadings (~0.02 mol%). With its stability and scalability, this self-sufficient biocatalyst offers a nature-friendly approach to deliver LAOs.