Category: 70110-65-5

Wang, Yinling published the artcileRedox-neutral photocatalytic strategy for selective C-C bond cleavage of lignin and lignin models via PCET process, Recommanded Product: 2-Phenoxy-1-phenylpropane-1,3-diol, the publication is Science Bulletin (2019), 64(22), 1658-1666, database is CAplus.

A redox-neutral photocatalytic strategy to accomplish this goal in both β-O-4 and β-1 lignin models at room temperature (RT) via proton-coupled electron transfer (PCET) process without any pretreatments of substrate, by adjusting the alkalinity of base to obtain a lignin models/base PCET pair with a bond dissociation free energy close to 102 kcal/mol was developed. Without breaking down C_β-C_γ bond and any C-O bonds, this PCET method is 100% atom economy and produces exclusive C_α-C_β bond cleavage products, such as benzaldehydes (up to 97%) and Ph ethers (up to 96%), in high to excellent yields and selectivities. Preliminary studies indicated that the PCET strategy was also effective for the depolymerization of native lignin at RT, thus providing significantly important foundation to the depolymerization of lignin.

Science Bulletin published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C15H22BBrO3, Recommanded Product: 2-Phenoxy-1-phenylpropane-1,3-diol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Zheng, Yi published the artcileCopper-Catalyzed Cleavage of Aryl C(OH)-C Bonds to Access Aryl Nitriles, Category: alcohols-buliding-blocks, the publication is ChemistrySelect (2021), 6(47), 13546-13550, database is CAplus.

It was found that aryl nitriles could be synthesized by cleavage of aryl C(OH)-C bonds in the presence of oxygen gas, (NH₄)₂CO₃ and Cu(OAc)₂. The present protocol allowed various secondary aryl alcs. to underwent the present transformation to give aryl nitriles in low to high yields. Lignin-related β-O-4 and β-1 linkages could be converted to benzonitriles under the present conditions, which provides an avenue to obtain value nitrile products via fragmentation of lignin.

ChemistrySelect published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C12H23N3S, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kong, Xiangchen published the artcileCritical Roles of the Oxygen-Containing Functional Groups via β-O-4 Lignin Linkage Hydrogenolysis over Copper Catalysts, Safety of 2-Phenoxy-1-phenylpropane-1,3-diol, the publication is ACS Sustainable Chemistry & Engineering (2021), 9(32), 10939-10947, database is CAplus.

The fundamental understanding of the catalytic performance of copper-based catalysts for lignin hydroconversion is delayed compared with the empirical optimization of the catalyst preparation Herein, we investigate the interplay between the lignin-abundant oxygen-containing functional groups and Cu active species via the catalytic β-O-4 lignin linkage hydrogenolysis. Catalyst performance data and elemental spectra characterizing the catalyst demonstrate the dominance of Cu⁰ in the catalysis. Remarkably, C_α-OH and C_α=O in the aliphatic chain play critical roles in this process, without which the linkage cannot be broken. These groups markedly accelerate the linkage cleavage by decreasing both the chemisorption energy between C_β-O and Cu⁰ and the bond dissociation energy of the linkage. On the contrary, the methoxyl groups attached to the aromatic rings hinder the bond cleavage as a result of the steric effect. Such hindrance is significantly affected by the amount and position of the methoxyl groups. The results of this work highlight the importance of the unique structures of lignin in its reductive depolymerization catalyzed by copper-based catalysts, which appear to offer an opportunity for tailoring efficient copper-based catalysts for lignin hydrogenolysis.

ACS Sustainable Chemistry & Engineering published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C15H16O3, Safety of 2-Phenoxy-1-phenylpropane-1,3-diol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Huang, Jinbao published the artcileDensity functional theory studies on pyrolysis mechanism of β-O-4 type lignin dimer model compound, Category: alcohols-buliding-blocks, the publication is Journal of Analytical and Applied Pyrolysis (2014), 98-108, database is CAplus.

Lignin is the main component of biomass with a complex, heterogeneous, three-dimensional polymeric structure of three main monolignols (p-coumaryl, coniferyl, and sinapyl alc.). In order to understand the pyrolysis mechanism of lignin and identify the chem. pathways for the formations of key products during pyrolysis, the pyrolysis processes of β-O-4 type lignin dimer model compound 1 (1-phenyl-2-phenoxy-1,3-propanediol) were theor. investigated by employing d. functional theory (DFT) methods at the B3LYP/6-31G(d,p) level. Based on related exptl. and calculation results of bond dissociation energies of β-O-4 type lignin dimer, three possible pyrolytic pathways (the homolytic cleavage of Cβ-O bond, the homolytic cleavage of Cα-Cβ bond and the concerted reactions) were proposed, the activation energies of each reaction step were calculated, and the temperature effect on pyrolysis processes was analyzed. The calculation results indicate that the homolytic cleavage reaction of Cβ-O bond and concerted reaction pathways could be the major reaction channels, and the homolytic cleavage reaction of Cα-Cβ bond and concerted reaction pathways could be the competitive reaction channels in pyrolysis processes. The concerted reactions would dominate over free-radical homolytic reactions at lower temperatures, while at high temperatures the free-radical reaction (C-O homolysis) would dominate over the concerted reactions.

Journal of Analytical and Applied Pyrolysis published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C15H16O3, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Liu, Huifang published the artcilePhotocatalytic Cleavage of C-C Bond in Lignin Models under Visible Light on Mesoporous Graphitic Carbon Nitride through π-π Stacking Interaction, Related Products of alcohols-buliding-blocks, the publication is ACS Catalysis (2018), 8(6), 4761-4771, database is CAplus.

Photocatalysis is a potentially promising approach to harvest aromatic compounds from lignin. However, the development of an active and selective solid photocatalyst is still challenging for lignin transformation under ambient conditions. We herein report a mild photocatalytic oxidative strategy for C-C bond cleavage of lignin β-O-4 and β-1 linkages using a mesoporous graphitic carbon nitride catalyst. Identifications by solid-state NMR techniques and d. functional theory (DFT) calculations indicate that π-π stacking interactions are most likely present between the flexible carbon nitride surface and lignin model mol. Besides, low charge recombination efficiency and high sp. surface area (206.5 m² g^-1) of the catalyst also contribute to its high catalytic activity. Mechanistic investigations reveal that photogenerated holes, as the main active species, trigger the oxidation and C-C bond cleavage of lignin models. This study sheds light on the interaction between complex lignin structures and the catalyst surface and provides a new strategy of photocatalytic cleavage of lignin models with heterogeneous photocatalysts.

ACS Catalysis published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C15H16O3, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Jia, Le published the artcileCleavage/cross-coupling strategy for converting β-O-4 linkage lignin model compounds into high valued benzyl amines via dual C-O bond cleavage, Safety of 2-Phenoxy-1-phenylpropane-1,3-diol, the publication is Chinese Chemical Letters (2022), 33(3), 1519-1523, database is CAplus.

Lignin is the most recalcitrant of the three components of lignocellulosic biomass. The strength and stability of the linkages have long been a great challenge for the degradation and valorization of lignin biomass to obtain bio-fuels and com. chems. Up to now, the selective cleavage of C-O linkages of lignin to afford chems. contains only C, H and O atoms. Authors’ group has developed a cleavage/cross-coupling strategy for converting 4-O-5 linkage lignin model compounds into high value-added compounds Herein, a palladium-catalyzed cleavage/cross-coupling of the β-O-4 lignin model compounds with amines via dual C-O bond cleavage for the preparation of benzyl amine compounds and phenols is presented.

Chinese Chemical Letters published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C15H16O3, Safety of 2-Phenoxy-1-phenylpropane-1,3-diol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Sturgeon, Matthew R. published the artcileA Mechanistic Investigation of Acid-Catalyzed Cleavage of Aryl-Ether Linkages: Implications for Lignin Depolymerization in Acidic Environments, SDS of cas: 70110-65-5, the publication is ACS Sustainable Chemistry & Engineering (2014), 2(3), 472-485, database is CAplus.

Acid catalysis has long been used to depolymerize plant cell wall polysaccharides, and the mechanisms by which acid affects carbohydrates have been extensively studied. Lignin depolymerization, however, is not as well understood, primarily due to the heterogeneity and reactivity of lignin. We present an exptl. and theor. study of acid-catalyzed cleavage of two non-phenolic and two phenolic dimers that exhibit the β-O-4 ether linkage, the most common intermonomer bond in lignin. This work demonstrates that the rate of acid-catalyzed β-O-4 cleavage in dimers exhibiting a phenolic hydroxyl group is 2 orders of magnitude faster than in non-phenolic dimers. The experiments suggest that the major product distribution is similar for all model compounds, but a stable phenyl-dihydrobenzofuran species is observed in the acidolysis of two of the γ-carbinol containing model compounds The presence of a methoxy substituent, commonly found in native lignin, prevents the formation of this intermediate. Reaction pathways were examined with quantum mech. calculations, which aid in explaining the substantial differences in reactivity. Moreover, we use a radical scavenger to show that the commonly proposed homolytic cleavage pathway of phenolic β-O-4 linkages is unlikely in acidolysis conditions. Overall, this study explains the disparity between rates of β-O-4 cleavage seen in model compound experiments and acid pretreatment of biomass, and implies that depolymerization of lignin during acid-catalyzed pretreatment or fractionation will proceed via a heterolytic, unzipping mechanism wherein β-O-4 linkages are cleaved from the phenolic ends of branched, polymer chains inward toward the core of the polymer.

ACS Sustainable Chemistry & Engineering published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C9H20Cl2Si, SDS of cas: 70110-65-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Umezawa, Toshiaki published the artcileAromatic ring cleavage of various β-O-4 lignin model dimers by Phanerochaete chrysosporium, Quality Control of 70110-65-5, the publication is Wood Research (1986), 8-17, database is CAplus.

In the degradation of β-O-4 lignin model dimers with different aromatic substituents on β-etherated aromatic ring by intact cells of P. chrysosporium, esters of arylglycerol, cyclic carbonates, formate and Me oxalate, were formed as aromatic ring cleavage products of the models. Substituents of aromatic nuclei considerably influenced the formation of aromatic ring cleavage products and O-C₄ cleavage product, arylglycerol.

Wood Research published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C9H7F3O3, Quality Control of 70110-65-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Wang, Yinling published the artcileCeCl₃-promoted simultaneous photocatalytic cleavage and amination of Cα-Cβ bond in lignin model compounds and native lignin, Safety of 2-Phenoxy-1-phenylpropane-1,3-diol, the publication is CCS Chemistry (2020), 2(3), 107-117, database is CAplus.

It remains challenging to achieve valuable platform chems. from lignin because of its complicated polymeric structure and inherent inert chem. activities. So far, only a few examples have been reported for the selective cleavage of C-C bonds in lignin due to their intrinsic inertness and ubiquity. Here, we present a simple and com. available cerium(III) chloride (CeCl₃)-promoted photocatalytic depolymerization strategy to realize the simultaneous cleavage and amination of Cα-Cβ bond in a variety of lignin model compounds at room temperature This procedure does not require any pretreatments and breakdown of C-O bonds or loss of γ-CH₂OH group to generate aldehydes (up to 97%) and N-containing products (up to 95%) in good to excellent yields. Addnl., this CeCl₃-based photocatalyst system could maintain excellent catalytic performance even after 10 sequential cycles with new starting materials. Moreover, this approach realizes the precise control over the reaction via switching the external light stimuli on/off. Further, this method is effective for the depolymerization of real lignin, thus affording the corresponding cleavage and amination products of Cα-Cβ bonds.

CCS Chemistry published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C18H12FN, Safety of 2-Phenoxy-1-phenylpropane-1,3-diol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Li, Xuan published the artcileBBr₃-Assisted Preparation of Aromatic Alkyl Bromides from Lignin and Lignin Model Compounds, Recommanded Product: 2-Phenoxy-1-phenylpropane-1,3-diol, the publication is Journal of Organic Chemistry (2018), 83(18), 11019-11027, database is CAplus and MEDLINE.

For the first time, BBr₃-assisted nucleophilic substitution was applied to a variety of β-O-4 and α-O-4 model compounds for the highly effective cleavage of different C-O bonds, including C-O_α-OH, C_β-O/C_α-O and C_Me-O bonds (<0.5 h and >99% conversion for most cases). Without any pretreatment, the substitution proceeds at room temperature in the absence of any catalyst, or additive, selectively affording phenols and important organic synthesis reagents, aromatic alkyl bromides, in high to excellent yields (up to 98%). Preliminary studies also highlight the prospect of this method for the effective cleavage of different types of C-O bonds in real lignin. A total 14 wt % yield of aromatic alkyl bromide, 4-(1,2-dibromo-3-hydroxypropyl)benzene-1,2-diol (10), has been obtained from an extracted lignin through this method.

Journal of Organic Chemistry published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C15H16O3, Recommanded Product: 2-Phenoxy-1-phenylpropane-1,3-diol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts