62080-95-9

Upstream product

• 90-05-1 2-methoxy-phenol 
• 13078-21-2 ethyl 2-(2-methoxyphenoxy)acetate 
• 94687-10-2 ethyl-3-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propanoate 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 10535-17-8 erythro-1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 10535-17-8 1-(3,4-dimethoxyphenyl)-2-(methoxyphenoxy)propane-1,3-diol 
• 7572-96-5 1-(3,4-Dimethoxyphenyl)-2-carbethoxy-2-(2-methoxyphenoxy)ethanol 
• 1835-02-5 2-Bromo-1-(3,4-dimethoxyphenyl)ethanone 
• 22675-96-3 2-methoxyphenoxy-3',4'-dimethoxyacetophenone 
• 10548-77-3 1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one 
• 32565-77-8 3-acetoxy-2-(2-methoxyphenoxy)-1-(3,4-dimethoxyphenyl)-1-propanone 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 

Downstream Products

• 1835-04-7 ethyl 3,4-dimethoxyphenyl ketone 
• 90-05-1 2-methoxy-phenol 

Relevant academic research and scientific papers

METHOD OF SELECTIVELY OXIDIZING LIGNIN

A method of selectively reacting lignin or a lignin-derived reactant to yield an aromatic product. The method includes the step of reacting lignin or a lignin-derived reactant with a molybdenum-containing catalyst, in a solvent, and optionally in the presence of an oxidant, for a time and a temperature wherein at least a portion of the lignin or lignin-derived reactant is selectively converted into an aromatic product, preferably coniferaldehyde and/or sinapaldehyde.

Selective oxidation of lignin model compounds

Lignin, the planet’s most abundant renewable source of aromatic compounds, is difficult to degrade efficiently to well-defined aromatics. We developed a microwave-assisted catalytic Swern oxidation system using an easily prepared catalyst, MoO2Cl2(DMSO)2, and DMSO as the solvent and oxidant. It demonstrated high efficiency in transforming lignin model compounds containing the units and functional groups found in native lignins. The aromatic ring substituents strongly influenced the selectivity of β-ether phenolic dimer cleavage to generate sinapaldehyde and coniferaldehyde, monomers not usually produced by oxidative methods. Time-course studies on two key intermediates provided insight into the reaction pathway. Owing to the broad scope of this oxidation system and the insight gleaned with regard to its mechanism, this strategy could be adapted and applied in a general sense to the production of useful aromatic chemicals from phenolics and lignin.

SELECTIVE C-O BOND CLEAVAGE OF OXIDIZED LIGNIN AND LIGNIN-TYPE MATERIALS INTO SIMPLE AROMATIC COMPOUNDS

A method to cleave C-C and C-0 bonds in β-Ο-4 linkages in lignin or lignin sub-units is described. The method includes oxidizing at least a portion of secondary benzylic alcohol groups in β-Ο-4 linkages in the lignin or lignin sub-unit to corresponding ketones and then leaving C-0 or C-C bonds in the oxidized lignin or lignin sub-unit by reacting it with an organic carboxylic acid, a salt of an organic carboxylic acids, and/or an ester of an organic carboxylic acids. The method may utilize a metal or metal-containing reagent or proceed without the metal or metal-containing reagent.

Hydrogenolysis of a γ-Acetylated Lignin Model Compound with a Ruthenium-Xantphos Catalyst

Catalytic hydrogenolysis of a γ-acetylated dimer lignin model compound is effected using a Ru-xantphos catalyst. Mechanistic investigations show mono-aryl degradation products are generated from the β-O-4 substrate as well as a terminal alkene ketone dimer (bis-aryl) that further dimerizes to a tetra-aryl product. Preliminary results using an acetylated kraft lignin as a substrate are also discussed. Graphical Abstract: [Figure not available: see fulltext.]

SELECTIVE AEROBIC ALCOHOL OXIDATION METHOD FOR CONVERSION OF LIGNIN INTO SIMPLE AROMATIC COMPOUNDS

Described is a method to oxidize lignin or lignin sub-units. The method includes oxidation of secondary benzylic alcohol in the lignin or lignin sub-unit to a corresponding ketone in the presence of unprotected primarily aliphatic alcohol in the lignin or lignin sub-unit. The optimal catalyst system consists of HNO3 in combination with another Br?nsted acid, in the absence of a metal-containing catalyst, thereby yielding a selectively oxidized lignin or lignin sub-unit. The method may be carried out in the presence or absence of additional reagents including TEMPO and TEMPO derivatives.

Chemoselective metal-free aerobic alcohol oxidation in lignin

An efficient organocatalytic method for chemoselective aerobic oxidation of secondary benzylic alcohols within lignin model compounds has been identified. Extension to selective oxidation in natural lignins has also been demonstrated. The optimal catalyst system consists of 4-acetamido-TEMPO (5 mol %; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) in combination with HNO3 and HCl (10 mol % each). Preliminary studies highlight the prospect of combining this method with a subsequent oxidation step to achieve C-C bond cleavage.

Chemical conversion of β-O-4 lignin linkage models through Cu-catalyzed aerobic amide bond formation

Methods for conversion of the lignin β-O-4 models into amide derivatives and phenols have been developed, which is achieved via chemo-selective oxidation of the secondary benzylic alcohol and subsequent Cu-catalyzed aerobic amide bond formation.