19752-95-5

Upstream product

• 110-83-8 cyclohexene 
• 931-17-9 1,2-Cyclohexanediol 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 91-16-7 1,2-dimethoxybenzene 
• 93-51-6 2-Methoxy-4-methylphenol 
• 1695-04-1 2-methoxyphenyl phenyl ether 
• 1655-70-5 di(2-methoxyphenyl) ether 
• 591-50-4 iodobenzene 
• 90-05-1 2-methoxy-phenol 
• 529-28-2 4-iodoanisol 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 
• 51533-22-3 trans-1-methoxy-2-phenylselenocyclohexane 
• 74-88-4 methyl iodide 

Downstream Products

• 78238-97-8 (3,4-dimethoxyphenyl)phenylmethane 

Relevant academic research and scientific papers

Catalytic Hydrogenolysis of Substituted Diaryl Ethers by Using Ruthenium Nanoparticles on an Acidic Supported Ionic Liquid Phase (Ru@SILP-SO3H)

Catalytic hydrogenolysis of diaryl ethers is achieved by using ruthenium nanoparticles immobilized on an acidic supported ionic liquid phase (Ru@SILP-SO 3 H) as a multifunctional catalyst. The catalyst components are assembled through a molecular approach ensuring synergistic action of the metal and acid functions. The resulting catalyst is highly active for the hydrogenolysis of various diaryl ethers. For symmetric substrates such as diphenyl ether, hydrogenolysis is followed by full hydrodeoxygenation producing the corresponding cycloalkanes as the main products. For unsymmetric substrates, the cleavage of the C-O bond is regioselective and occurs adjacent to the unsubstituted phenyl ring. As hydrogenation of benzene is faster than hydrodeoxygenation over the Ru@SILP-SO 3 H catalyst, controlled mixtures of cyclohexane and substituted phenols are accessible with good selectivity. Application of Ru@SILP-SO 3 H catalyst in continuous-flow hydrogenolysis of 2-methoxy-4-methylphenoxybenzene is demonstrated with use of commercial equipment.

Model Systems for Cytochrome P450 Dependant Mono-oxygenases. Part 7. Alkene Epoxidation by Iodosylbenzene Catalyzed by Ionic Iron(III) Tetrarylporphyrins Supported on Ion-exchange Resins

Ionic iron(III) tetraarylporphyrins are readily adsorbed onto cross-linked polystyrene ion-exchange resins.These supported metalloporphyrins can act as heterogenous catalysts for the oxidation of organic compounds by iodosylbenzene in methanolic solution.Their catalytic activity for the epoxidation and allylic oxidation of cyclohexene and the epoxidation of (Z)-cyclooctene has been studied.With cyclohexene, epoxidation is favoured by increased cross-linking of the resin support, and allylic oxidation is shown to arise largely from an autoxidation which can be minimised by carrying out the reaction under nitrogen. (Z)-cyclooctene gives only epoxidation which is also favoured by increased cross-linking and is unaffected by changes in the surface area of the support.The influence of the support cross-linking on catalyst performance is discussed.Supproted anionic iron(III) porphyrins are poor catalysts unless they are sterically hindered with ortho-groups on the aromatic substituents.The fate of the oxidant in the heterogeneous oxidations is examined and comparison with the analogous homogeneous reactions suggests that some of the oxidant is consumed in oxidising the polymer support.A brief study of the oxidation of cyclohexene by iodosylbenzene catalyzed by a cation exchange resin in its acidic form, in the absence of metalloprophyrin, is reported.

The Effect of Sulfonate Groups in the Structure of Porous Aromatic Frameworks on the Activity of Platinum Catalysts Towards Hydrodeoxygenation of Biofuel Components

Abstract: Platinum catalysts based on porous aromatic frameworks (PAF-30 and PAF-30–SO3H) have been synthesized. Properties of the obtained catalysts have been assessed via hydrogenation of guaiacol, veratrole, and pyrocatechol at 250°С and hydrogen pressure 3.0 MPa in isopropanol medium. It has been shown that the presence of acidic sites in the catalyst significantly increases the yield of deoxygenation products. The effect of the substrate structure on the rate of its hydrodeoxygenation and the mechanism of the occurring processes have been studied. [Figure not available: see fulltext.]

Catalytic role of metals supported on SBA-16 in hydrodeoxygenation of chemical compounds derived from biomass processing

Hydrodeoxygenation (HDO) carried out at high temperatures and high hydrogen pressures is one of the alternative methods of upgrading pyrolytic oils from biomass, leading to high quality biofuels. To save energy, it is important to carry out catalytic proc

Reductive fractionation of woody biomass into lignin monomers and cellulose by tandem metal triflate and Pd/C catalysis

A catalytic process for the upgrading of woody biomass into mono-aromatics, hemi-cellulose sugars and a solid cellulose-rich carbohydrate residue is presented. Lignin fragments are extracted from the lignocellulosic matrix by cleavage of ester and ether linkages between lignin and carbohydrates by the catalytic action of homogeneous Lewis acid metal triflates in methanol. The released lignin fragments are converted into lignin monomers by the combined catalytic action of Pd/C and metal triflates in hydrogen. The mechanism of ether bond cleavage is investigated by lignin dimer models (benzyl phenyl ether, guaiacylglycerol-β-guaiacyl ether, 2-phenylethyl phenyl ether and 2-phenoxy-1-phenylethanol). Metal triflates are involved in cleaving not only ester and ether linkages between lignin and the carbohydrates but also β-O-4 ether linkages within the aromatic lignin structure. Metal triflates are more active for β-O-4 ether bond cleavage than Pd/C. On the other hand, Pd/C is required for cleaving α-O-4, 4-O-5 and β-β linkages. Insight into the synergy between Pd/C and metal triflates allowed optimizing the reductive fractionation process. Under optimized conditions, 55 wt% mono-aromatics-mainly alkylmethoxyphenols-can be obtained from the lignin fraction (23.8 wt%) of birch wood in a reaction system comprising birch wood, methanol and small amounts of Pd/C and Al(III)-triflate as catalysts. The promise of scale-up of this process is demonstrated.

Exploring the reaction pathways of Pd(II)-catalyzed cyclohexene oxidation with molecular oxygen: Vinylic and allylic oxidation, disproportionation and oxidative dehydrogenation

Palladium(ii) salts are able catalysts to promote different oxidative transformations of cyclohexene in the presence of molecular oxygen: vinylic and allylic oxidation and disproportionation. In this paper, we assessed the main aspects that govern these reactions, by using palladium salts (i.e. PdCl2, Pd(OAc)2, Pd(acac)2 and Pd(CF3COO)2) in protic solvents (i.e. CH3COOH and CH3OH). When carried out in CH3COOH solutions at 333 K, the Pd(ii)-catalyzed oxidation reactions preferentially convert cyclohexene to 2-cyclohexenil-1-acetate. Benzene was the secondary product. It was found that the efficiency of the palladium reoxidant followed the trend: Fe(NO3)3 > LiNO3 > CuCl2 > FeCl3. Pd(OAc)2 was the most active catalyst. Replacing Cu(OAc)2 by Fe(NO3)3 notably enhances the conversion of cyclohexene and the selectivity of 2-cyclohexenyl-1-acetate, reducing significantly the reaction time from 22 to 3 h. Conversely, when performed in CH3OH solutions, the reaction had its selectivity drastically changed; benzene and cyclohexane were the most selectively formed products (i.e. through disproportionation reaction). In this case, the reaction occurred at room temperature and in the absence of a reoxidant. Hence, Pd(CF3OO)2 is the most active and selective catalyst. The addition of the Fe(NO3)3 reoxidant and increasing the reaction temperature to 328 K resulted in the formation of 1,2-dimethoxycyclohexane and benzene as major products (i.e. allylic oxidation and oxidative dehydrogenation products, respectively). Catalytic cycles for these transformations were proposed based on experimental data and palladium chemistry.

Influences of Various Supports, γ-Al2O3, CeO2, and SBA-15 on HDO Performance of NiMo Catalyst

Hydrodeoxygenation (HDO) of guaiacol (GUA), has been carried out over γ-Al2O3, CeO2, SBA-15 supported NiMo catalysts in an autoclave at 250°C and a hydrogen pressure of 5 MPa. In comparison with NiMo/γ-Al2O3, both NiMo/CeO2 and NiMo/SBA-15 catalysts showed their higher activities. NiMo/SBA-15 has been found to be the most potential one for HDO of GUA with GUA conversion and HDO degree of 90 and 67.5 %, respectively. The main product was cyclohexane with its yield of 56 mol%. The outstanding activity of this catalyst results from a high dispersion of its active sites on SBA-15 as catalyst support. For CeO2 supported catalyst, some interactions of Ce-Mo can be occurred, leading to an enhancement of its HDO performance. Graphical Abstract: [Figure not available: see fulltext.]

Selective production of cyclohexanol and methanol from guaiacol over Ru catalyst combined with MgO

Selective demethoxylation from aqueous guaiacol proceeded over Ru catalysts at relatively lower temperatures (≤433 K). Addition of MgO to the reaction media suppressed the unselective C-O dissociation. Cyclohexanol and methanol were obtained in high yield (>80%). A reaction route is proposed where partially hydrogenated guaiacol is decomposed into methanol and phenol, which is further hydrogenated to cyclohexanol. the Partner Organisations 2014.

New oxidative transformations of alkenes and alkynes under the action of diacetoxyiodobenzene

Treatment of alkenes and alkynes with diacetoxyiodobenzene activated by mineral and organic acids predominantly results in oxidative rearrangement. 1,4-Diphenylbutadiene in MeOH gives 3,4-dimethoxy-1,4-diphenylbut-1-ene.