Category: 183303-74-4

Sun, Chen published the artcileMechanochemical cleavage of lignin models and lignin via oxidation and a subsequent base-catalyzed strategy, HPLC of Formula: 183303-74-4, the publication is Green Chemistry (2020), 22(11), 3489-3494, database is CAplus.

Mechanochem. cleavage of lignin dimer model compounds to phenolic monomers has been developed via a two-step strategy under milling conditions. In the first step of this process, the secondary benzylic alc. of lignin β-O-4 linkages was selectively oxidized to the corresponding ketones over a 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)/NaNO₂ catalytic system under milling conditions. In the subsequent step, mechanochem. selective cleavage of the C_β-O bonds and C_α-C_β bonds of lignin β-O-4 ketones to acids and phenols was promoted by NaOH-catalyzed depolymerization In addition, this two-step strategy was performed to depolymerize organosolv birch lignin, giving aromatic monomers with good selectivity for syringate. This approach provides an efficient method to convert the β-O-4 linkages of lignin to valuable aromatic monomers under mild reaction conditions.

Green Chemistry published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C12H10F2Si, HPLC of Formula: 183303-74-4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Shimizu, Satoko published the artcileEffect of type of aromatic nucleus in lignin on the rate of the β-O-4 bond cleavage during alkaline pulping process, Formula: C16H18O4, the publication is Journal of Wood Science (2015), 61(5), 529-536, database is CAplus.

Several C₆-C₃ and C₆-C₂-type dimeric non-phenolic β-O-4 lignin model compounds, whose aromatic nuclei consisting of the carbon skeleton and β-O-4 linkage are named the A- and B-rings, resp., were treated under alk. pulping conditions to examine whether or not the substitution of methoxyl group on the B-ring or of guaiacyl for syringyl A-ring accelerates the β-O-4 cleavage as a further study of our previous reports. It was suggested that either first or second substitution of methoxyl group on the B-ring accelerates the β-O-4 cleavage in both C₆-C₃ and C₆-C₂ compounds although the former compounds are more sensitive to the substitution than the latter, suggesting that the lack of the γ-hydroxymethyl group makes model compound insensitive to the substitution. It was confirmed that the substitution of guaiacyl for syringyl A-ring accelerates the β-O-4 cleavage in both C₆-C₃ and C₆-C₂ compounds with the degrees similar to each other regardless of the type of the B-ring. It was clarified that the leaving ability of the leaving B-ring phenoxides in the β-O-4 cleavage does not correlate well with the p^Ka values of the conjugate acids of the phenoxides, which is not in accordance with the common property of a nucleophilic substitution reaction.

Journal of Wood Science published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C3H5BN2O2, Formula: C16H18O4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Dabral, Saumya published the artcileMechanochemical Oxidation and Cleavage of Lignin β-O-4 Model Compounds and Lignin, Product Details of C16H18O4, the publication is ACS Sustainable Chemistry & Engineering (2018), 6(3), 3242-3254, database is CAplus.

A mechanochem. oxidation and cleavage reaction in lignin β-O-4 model compounds and lignin catalyzed by HO-TEMPO/KBr/Oxone (TEMPO is 2,2,6,6-tetramethyl-1-piperidinyloxy) has been developed under milling conditions. The studies on nonphenolic lignin β-O-4 model compounds led to selective oxidations of the benzylic hydroxyl groups. Subjecting phenolic lignin model compounds to the oxidative conditions in a ball mill initiated aryl-C_α bond cleavage reactions leading to the formation of the corresponding quinones and phenol derivatives Transferring the mechanochem. protocol to lignin resulted in the simultaneous oxidation and cleavage of bonds with varied selectivity for monomeric products. Finally, a scale-up approach of the oxidative procedure by using vibrating disk mill technol. enabled the mechanochem. protocol to be applied in gram-scale batch reactions under reduced milling time, while affording a similar extent of oxidation

ACS Sustainable Chemistry & Engineering published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C16H18O4, Product Details of C16H18O4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Liang, Jing published the artcileNano WO₃-Catalyzed One-Pot Process for Mild Oxidative Depolymerization of Lignin and its Model Compounds, HPLC of Formula: 183303-74-4, the publication is ChemCatChem (2021), 13(17), 3836-3845, database is CAplus.

Despite challenges related to the robust and irregular structure of lignin, the valorization of this aromatic biopolymer has aroused great interest. However, the current methods exhibit problems such as harsh reaction conditions, complicated operation, and difficult recovery of catalyst. Herein we present a one-pot process for the mild oxidative depolymerization of lignin and lignin model compounds catalyzed by nano WO₃, along with tert-Bu hydrogen peroxide (TBHP) as the oxidant and NaOH as the additive, which exhibits advantages of both homogeneous and heterogeneous catalysis. Under the optimized condition, it yielded 80.4 wt % of liquid oil from organosolv lignin with 7.6 wt % of vanillic acid as the main monomer product, accounting for 91.6 wt % monomeric selectivity. Mechanism studies on the model substrate suggest that the reaction proceeds via an oxidation of C_α-OH to C=O followed by C-O bond cleavage to afford phenol and ketone products which may undergo further oxidation to produce aromatic carboxylic acids. We have developed an operationally simple procedure for mild fragmentation of lignin and lignin model compounds with excellent yields, which provides the potential to expand the existing lignin usage from energy source to value-added commodity chems.

ChemCatChem published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C16H18O4, HPLC of Formula: 183303-74-4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Luo, Huihui published the artcileCobalt Nanoparticles-Catalyzed Widely Applicable Successive C-C Bond Cleavage in Alcohols to Access Esters, Name: 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, the publication is Angewandte Chemie, International Edition (2020), 59(43), 19268-19274, database is CAplus and MEDLINE.

Selective cleavage and functionalization of C-C bonds have important applications in organic synthesis and biomass use. However, functionalization of C-C bonds by controlled cleavage remains difficult and challenging because they are inert. Herein, the authors describe an unprecedented efficient protocol for the breaking of successive C-C bonds in alcs. to form esters with one or multiple carbon atoms less using heterogeneous cobalt nanoparticles as catalyst with dioxygen as the oxidant. A wide range of alcs. including inactive long-chain alkyl aryl alcs. undergo smoothly successive cleavage of adjacent -(C-C)_n– bonds to afford the corresponding esters. The catalyst was used for seven times without any decrease in activity. Characterization and control experiments disclose that cobalt nanoparticles are responsible for the successive cleavage of C-C bonds to achieve excellent catalytic activity, while the presence of Co-N_x has just the opposite effect. Preliminary mechanistic studies reveal that a tandem sequence reaction is involved in this process.

Angewandte Chemie, International Edition published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C16H18O4, Name: 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Luo, Huihui published the artcileNitrogen-Doped Carbon-Modified Cobalt-Nanoparticle-Catalyzed Oxidative Cleavage of Lignin β-O-4 Model Compounds under Mild Conditions, SDS of cas: 183303-74-4, the publication is ACS Sustainable Chemistry & Engineering (2018), 6(11), 14188-14196, database is CAplus.

A noble-metal-free Co-based catalyst, derived from pyrolysis of natural vitamin B₁₂ on activated carbon, is developed for the first time for one-pot oxidative cleavage of lignin linkages to phenols and aromatic esters with mol. oxygen as the oxidant under mild reaction conditions. High yields of phenol were obtained, and no oxidative coupling of phenol was produced based on the present cobalt catalyst. Compared to the previous report, the present catalyst can achieve the oxidative cleavage of β-O-4 ketones even at room temperature using a dioxygen balloon. The heterogeneous catalyst shows robust recyclability and can be conveniently recovered and reused up to eight times without an appreciable loss of catalytic activity. Moreover, this catalyst system can realize the bond cleavage of organosolv lignin. The evidence of depolymerization was given by two-dimensional heteronuclear single quantum coherence NMR and gel permeation chromatog. Characterization of the catalyst by inductively coupled plasma, N₂ adsorption-desorption, Raman spectroscopy, SEM, transmission electron microscopy (TEM), high-resolution TEM, high-angle angular dark-field scanning TEM, energy-dispersive X-ray spectroscopy, XPS, and control experiments provide a fundamental understanding of the catalytic materials and the reaction pathway. Co₃O₄ in situ supported on a N-doped carbon matrix by the way of high-temperature pyrolysis might be a catalytically active species. Two reaction intermediates are detected and confirmed by gas chromatograph-mass spectrometry.

ACS Sustainable Chemistry & Engineering published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C16H18O4, SDS of cas: 183303-74-4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Zhao, Li published the artcileAu-Pd alloy cooperates with covalent triazine frameworks for the catalytic oxidative cleavage of β-O-4 linkages, SDS of cas: 183303-74-4, the publication is Green Chemistry (2019), 21(24), 6707-6716, database is CAplus.

To design highly efficient catalysts for the cleavage of the C-O/C-C bond is the key task in the depolymerization of lignin. Bimetallic alloy catalysts Au-Pd-CTFs were developed to be effective in the oxidative cleavage of β-O-4 lignin model compounds with O₂. Au-Pd nanoparticles with an Au/Pd molar ratio between 1 : 1 and 1 : 1.5 showed the highest cleavage efficiency. The kinetics of the reaction process revealed that a synergistic effect between Au and Pd played a crucial role in the oxidation of C_α-OH into C_α-O, which was the rate-determining step for the whole oxidative cleavage process. Further insight revealed that the cooperative effect between Au-Pd nanoparticles and the support covalent triazine frameworks (CTFs) facilitated the cleavage of the formed β-O-4 ketone compound to the corresponding aromatics In addition, Au-Pd-CTF catalysts also showed efficiency in the oxidative transformation of the organosolv lignin. This catalytic system will provide guidance in the oxidative cleavage of β-O-4 linkages in lignin.

Green Chemistry published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C28H18O4, SDS of cas: 183303-74-4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Weickmann, Daniel published the artcileThe Ru-Catalyzed Alkylative Dearyloxylation of L-type 2-Aryloxyethanols, Safety of 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, the publication is ChemCatChem (2013), 5(8), 2170-2173, database is CAplus.

The authors report the ruthenium-catalyzed cleavage of the β-C-O linkage in different lignin model compounds; this also allow for direct sequential alkylation of the resulting acetophenone derivatives using alcs. as alkylation agents. Thus, reacting PhCH(OH)CH₂OPh with (Ph₃P)₃RuCl₂ gave PhCOMe and PhOH in excellent yields. Adding PhCH₂OH led to PhCOCH₂CH₂Ph in 71% yield.

ChemCatChem published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C8H15NO, Safety of 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Tan, Hua published the artcileFacile preparation of N-doped graphitic carbon encapsulated nickel catalysts for transfer hydrogenolysis of lignin β-O-4 model compounds to aromatics, SDS of cas: 183303-74-4, the publication is Sustainable Energy & Fuels (2022), 6(11), 2745-2754, database is CAplus.

Herein, N-doped carbon embedded Ni catalysts were prepared by a co-impregnation method followed by pyrolysis in a N₂ atmosphere for transfer hydrogenolysis of lignin β-O-4 alc. and ketone model compounds using isopropanol as the hydrogen source. It was found that pyrolysis at 800°C resulted in the formation of graphitic N-doped carbon shell encapsulated Ni nanoparticles (Ni@NC-800). The obtained Ni@NC-800 exhibited higher activity and selectivity to aromatics in the conversion of 2-phenoxy-1-phenylthanol and 2-phenoxyacetophenone, compared with Ni@NC-600 and Ni/NC-800. Moreover, the selectivity to aromatics could be further improved over Ni@NC-800-H, which is Ni@NC-800 after strong acid leaching. However, the presence of C_α-OH in lignin β-O-4 model compounds was essential for their product distributions. The control and characterization experiments suggested that the catalytic reaction occurred on the surface of N-doped carbon shells, because the encapsulated Ni NPs could donate electrons to the outer shells, leading to surface electron enrichment, thus making inert shells the new active sites in Ni@NC-800-H. In addition, Ni@NC-800-H was efficient for the conversion of various lignin β-O-4 alc. and ketone model compounds with methoxyl groups with high yields of the aromatic products and also possessed high stability during consecutive reaction runs, which is because Ni nanoparticles are phys. isolated from the reactive environment.

Sustainable Energy & Fuels published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C12H14IN, SDS of cas: 183303-74-4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Zhang, Chaofeng published the artcilePromoting Lignin Depolymerization and Restraining the Condensation via an Oxidation-Hydrogenation Strategy, HPLC of Formula: 183303-74-4, the publication is ACS Catalysis (2017), 7(5), 3419-3429, database is CAplus.

For lignin valorization, simultaneously achieving the efficient cleavage of ether bonds and restraining the condensation of the formed fragments represents a challenge thus far. Herein, we report a two-step oxidation-hydrogenation strategy to achieve this goal. In the oxidation step, the O₂/NaNO₂/DDQ/NHPI system selectively oxidizes C_αH-OH to C_α=O within the β-O-4 structure. In the subsequent hydrogenation step, the α-O-4 and the preoxidized β-O-4 structures are further hydrogenated over a NiMo sulfide catalyst, leading to the cleavage of C_β-OPh and C_α-OPh bonds. Besides the transformation of lignin model compounds, the yield of phenolic monomers from birch wood is up to 32% by using this two-step strategy. The preoxidation of C_αH-OH to C_α=O not only weakens the C_β-OPh ether bond but also avoids the condensation reactions caused by the presence of C_α⁺ from dehydroxylation of C_αH-OH. Furthermore, the NiMo sulfide prefers to catalyze the hydrogenative cleavage of the C_β-OPh bond connecting with a C_α=O rather than catalyze the hydrogenation of C_α=O back to the original C_αH-OH, which further ensures and utilizes the advantages of preoxidation

ACS Catalysis published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C10H9NO, HPLC of Formula: 183303-74-4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem