31637-03-3

Upstream product

• 111-66-0 oct-1-ene 
• 201230-82-2 carbon monoxide 
• 107-21-1 ethylene glycol 

Relevant academic research and scientific papers

Synthesis of cyclic acetals by hydroformylation of oct-1-ene in the presence of polyols

Rhodium-catalyzed hydroformylation of oct-1-ene in acid medium in the presence of polyols gives acetals of the initially formed aldehydes. The use of water-soluble trisodium salt of tris(sulfonatophenyl)phosphine as a ligand favors easy separation of the reaction products and enables repeated use of the catalytic system. A minor additive (2 wt.%) of the obtained acetal mixture improves the lubricating properties of diesel fuel by 30% and markedly reduces gum formation during combustion.

Tandem Hydroformylation–Acetalization Using a Water-Soluble Catalytic System: a Promising Procedure for Preparing Valuable Oxygen-Containing Compounds from Olefins and Polyols

Specific features of the tandem hydroformylation–acetalization of a series of unsaturated compounds and polyols in the presence of a water-soluble catalytic system containing a rhodium catalyst precursor, sodium (triphenylphosphino)trisulfonate, and H2SO4 were investigated. The process parameters, including component ratio, temperature, and reaction time, were optimized using model substrates. With the suggested catalytic system, the conversion of unsaturated compounds to target products, acetals, reached 95%, and the catalytic system could be separated from the reaction products and repeatedly used without considerable loss of the activity. The acetal preparation procedure is versatile with respect to the raw materials. Batches of acetal mixtures were prepared by the suggested procedure from 1-octene and polyols, e.g., ethylene glycol, glycerol, and sorbitol.

Cation-exchange resins in the hydroformylation–acetalization tandem reaction

Cation-exchange resins in the acid form (Amberlyst-16, Wofatit KPS 200, Nafion, KU-2) have been tested as the acidic component of a catalyst system for the hydroformylation–acetalization tandem process. It has been shown that the hydroformylation of octene-1 in the presence of ethylene glycol and glycerol using a catalyst system comprising a rhodium complex, a phosphine ligand, and a solid acid leads to the formation of acetals with a yield of up to 99%.

Phosphonium-based aminophosphines as bifunctional ligands for sequential catalysis of one-pot hydroformylation-acetalization of olefins

A series of ionic phosphonium-based aminophosphines L1-L3 were prepared and fully characterized, in each of which the involved bifunctional moieties of the phosphine fragment and Lewis acidic phosphonium were linked together by stable chemical bonds and bridged by one N-atom. The molecular structure of the L2-ligated Rh-complex (Rh-L2) indicated that such bifunctionalities were well retained without incompatibility problems. Investigations on co-catalysis over L1-L3 showed that L3 exhibited the best sequential catalysis for both hydroformylation and acetalization. The phosphine fragment in L3 was responsible for hydroformylation together with the Rh-complex and the phosphonium acted as the Lewis acidic catalyst in charge of acetalization. The L3-Rh(acac)(CO)2 system also exhibited good generality to hydroformylation-acetalization of a wide range of olefins in different alcohols.

Tandem hydroformylation-acetalization with a ruthenium catalyst immobilized in ionic liquids

For the first time, a ruthenium catalyzed hydroformylation-acetalization reaction of olefins is presented. The tandem reaction proceeds well with 1,2- or 1,3-diols, trapping the intermediary formed aldehydes as cyclic acetals. In this manner the hydrogenation of the aldehydes to the corresponding alcohols usually observed with Ru catalysts is prevented. The optimized catalytic system consisting of Ru catalyst, ionic liquids, acetic acid and ammonium salt can be recycled and reused for at least two further runs. Interestingly, styrenes as substrate give preferentially terminal acetals.

Formation of acetals under rhodium-catalyzed hydroformylation conditions in alcohols

Hydroformylation of terminal alkenes in alcohol solvents leads to the selective formation of the corresponding acetals. The Xantphos ligand gave the best results as well as acetal selectivities higher than 99% and linear/branched ratios of up to 52 were obtained. The scope of the reaction was studied. Acetals were found to be unreactive under hydroaminomethylation conditions. Copyright