33364-77-1

Upstream product

• 50-00-0 formaldehyd 
• 93-51-6 2-Methoxy-4-methylphenol 
• 72791-83-4 2-methoxy-1-methoxymethoxy-4-methylbenzene 

Downstream Products

• 115020-28-5 bis-(5-acetoxy-4-methoxy-2-methyl-phenyl)-methane 
• 1164-05-2 bis-(4,5-dimethoxy-2-methyl-phenyl)-methane 
• 111497-39-3 bis-(5-ethoxy-4-methoxy-2-methyl-phenyl)-methane 
• 5191-69-5 bis(4-methoxy-2-methylphenyl)methane 
• 15534-74-4 4,4'-methylenebis(3-methylphenol) 
• 1421690-15-4 bis(5-cyanato-4-methoxy-2-methylphenyl)methane 
• 111088-83-6 5,5'-diethoxy-4,4'-dimethoxy-2,2'-dimethyl-benzophenone 

Relevant academic research and scientific papers

Synthesis of Lignin-Derived Bisphenols Catalyzed by Lignosulfonic Acid in Water for Polycarbonate Synthesis

Lignosulfonic acid, a byproduct of the paper industry, was demonstrated to be an efficient and green catalyst in water for the stoichiometric condensation of creosol with formaldehyde to synthesize lignin-derived renewable bisphenols. The distribution and structures of the products were confirmed by 1H NMR, 13C NMR, and FTIR spectroscopy and X-ray analysis; furthermore, a possible reaction mechanism was proposed. A polycarbonate was prepared from the bisphenol product and characterized as a model application, and thermogravimetric analysis (TGA) showed that decomposition occurred in a single stage with the maximum rate of degradation at approximately 420°C. Differential scanning calorimetry (DSC) analysis showed that the glass transition temperature and melting peak of the polycarbonate were approximately 122 and 314°C, respectively. The environmentally friendly characteristics of this study are featured by the integrated utilization of a biorenewable feedstock, a green biomacromolecule catalyst, and a green solvent for the preparation of valuable biochemicals and materials.

Renewable polyphenols, thermoplastics, and resins

A series of renewable bisphenols has been synthesized from creosol (2-methoxy-4-methylphenol) through stoichiometric condensation with short chain aldehydes. Creosol can be readily produced from lignin, potentially allowing for the large scale synthesis o

PRODUCTION OF HIGHLY PURE META,META-COUPLED BIS(4-ALKYLPHENOL) DERIVATIVES AND USES THEREOF

In general the present invention concerns a method for production of highly pure m,m'- coupled bis(4-alkylphenol) derivatives from particular lignin-derived 4-alkylphenol derivatives. More specifically this invention relates to a process for the selective

Sustainable bisphenols from renewable softwood lignin feedstock for polycarbonates and cyanate ester resins

The selective reductive catalytic depolymerisation of softwood lignin (e.g. pine, spruce) yields predominantly 4-n-propylguaiacol (4PG; 15-20 wt% on lignin basis), an interesting platform chemical for bio-based chemistry. This contribution specifically shows promising technical, sustainable and environmental advantages of such a bio-phenol for various polymer applications. The bisphenolic polymer precursor, 5,5′-methylenebis(4-n-propylguaiacol) (m,m′-BGF-4P), was therefore first synthesized by acid-catalysed condensation, and its synthesis and isolation are compared with shorter chain analogs, viz. 4-methyl- and 4-ethylguaiacol. A thorough GC-GPC/SEC analysis of the crude condensation mixture was developed to assess the purity of the isolated dimers. Isolation is done by a single-step crystallization, yielding 57 wt% of m,m′-BGF-4P in >99% purity. This pure m,m′-BGF-4P bisphenol displays a notably reduced potency to activate human estrogen receptor alpha (hERα; EC50 at 10-5 M) in comparison with commercial bisphenols, and is therefore useful for future polymer applications. As a proof of concept, polycarbonates and cyanate ester resins were prepared from m,m′-BGF-4P and compared to other bisphenols. The polycarbonate had Mn = 5182 g mol-1, Tg = 99 °C, Tm = 213 °C, Td,5% = 360 °C, and displayed improved processability in common solvents, as opposed to the methylated and ethylated bisguaiacols. A fully cured resin disk exhibited a Tg = 193 °C, Td,5% = 389 °C and a water uptake of only 1.18% after being immersed in 85 °C water for four days. These results underscore the potential of the intrinsic functionality of lignin-derived building blocks to transcend the scope of renewability.

Preparation of lignin/glycerol-based bis(cyclic carbonate) for the synthesis of polyurethanes

A bis(cyclic carbonate) was obtained via glycidylation of lignin-based bisphenol followed by cycloaddition with CO2. Further polyaddition between the bis(cyclic carbonate) and diamines led to the synthesis of polyurethanes. The structure and th

Synthesis of renewable bisphenols from creosol

A series of renewable bisphenols has been synthesized from creosol (2-methoxy-4-methylphenol) through stoichiometric condensation with short-chain aldehydes. Creosol can be readily produced from lignin, potentially allowing for the large scale synthesis o

The O-substitution pattern of the MoCl5-mediated oxidative aryl-aryl coupling reaction

Different protective groups for the phenolic oxygen were investigated in the molybdenum pentachloride-mediated dehydrodimerization reaction. Cyclic acetals and ketals, triisopropylsilyl and alkoxycarbonylmethyl moieties are compatible with the strong acidic reaction conditions.