5457-70-5Relevant academic research and scientific papers
Recyclable DMAP-Functionalized polymeric nanoreactors for highly efficient acylation of alcohols in aqueous systems
Qiu, Jiaqi,Meng, Fuliang,Wang, Maolin,Huang, Jinjin,Wang, Chengzhan,Li, Xiao,Yang, Guang,Hua, Zan,Chen, Tao
, (2021/03/30)
Fabrication of highly efficient and recyclable nanoreactors via macromolecular self-assembly represents a promising strategy for green organic transformation. In this study, small-molecule catalysts 4-(N,N-dimethylamino)pyridine (DMAP) functionalized nanoreactors were constructed by self-assembly of amphiphilic block copolymers with DMAP moieties in the hydrophobic block, leading to heterogeneous catalysts with excellent dispersity in water. The key preparation route included reversible addition-fragmentation chain transfer (RAFT) polymerization of 2-(N-methyl-N-(4-pyridyl)amino)ethyl methacrylate (MAPMA) and methyl methacrylate (MMA) using poly (oligomeric (ethylene glycol) methyl ether methacrylate) (POEGMA) as a hydrophilic macromoleculer RAFT reagent. The characterization by dynamic light scattering (DLS) and transmission electron microscopy (TEM) shows that the nanoreactors possess a core-shell nanostructure with the diameter of around 110 nm. The resulting polymeric nanoreactors showed excellent catalytic activity for acylation of alcohols in water. High conversion of a variety of alcohol (>99%) and excellent product selectivity were achieved. The high catalytic efficiency of the nanoreactors may be attributed to the enhancement of the interaction between the reactant and the catalyst in the confined hydrophobic space, which simulates how enzymes usually work. Moreover, the catalyst could be easily recovered by thermos-responsive separation and reused with high activity for more than 5 cycles. This study presents an efficient approach to achieve green catalytic reactions which are normally incompatible to aqueous conditions, potentially applicable to other catalytic systems such as metal-mediated organic transformations.
Catalytic Aerobic Oxidation of Arylhydrazides with Iron Phthalocyanine
Hashimoto, Takuma,Hirose, Daisuke,Taniguchi, Tsuyoshi
supporting information, p. 3346 - 3352 (2015/11/03)
A convenient method for the synthesis of 2-arylazocarboxylates from 2-arylhydrazinecarboxylates by aerobic oxidation with iron phthalocyanine is described. The reaction is applicable to oxidative activation of 1-acyl-2-phenylhydrazines. Some preliminary experiments suggest Michaelis-Menten kinetics and participation of radical species in the reaction mechanism.
The phosphate-carboxylate mixed-anhydride method: A mild, efficient process for ester and amide bond construction
McNulty, James,Vemula, Ramesh,Krishnamoorthy, Venkatesan,Robertson, Al
experimental part, p. 5415 - 5421 (2012/09/08)
A highly efficient carboxylate-phosphate anhydride pathway is described for the direct, economical synthesis of esters and amides from carboxylic acids and alcohols or amines. The reaction proceeds with retention of configuration with both chiral secondary alcohols and α-amino acid derivatives allowing access to useful chiral auxiliaries, ligands, and organocatalysts. Ester and amide products can be isolated directly in high yield due to the water soluble nature of the side products.
Direct formation of esters and amides from carboxylic acids using diethyl chlorophosphate in pyridine
McNulty, James,Krishnamoorthy, Venkatesan,Robertson, Al
scheme or table, p. 6344 - 6347 (2009/04/07)
An efficient method involving pyridine activation of the carboxylate-phosphate anhydride pathway is described resulting in a direct synthesis of esters from carboxylic acids and alcohols, as well as in the formation of useful amide and peptide derivatives. The reaction proceeds with retention of configuration with both chiral secondary alcohols and α-amino acid derivatives. Ester and amide products can be isolated directly in high yield due to the water soluble nature of the side products.
Efficient liquid phase acylation of alcohols over basic ETS-10 molecular sieves
Waghmode, Suresh B.,Thakur, Vinay V.,Sudalai, Arumugam,Sivasanker, Subramanian
, p. 3145 - 3147 (2007/10/03)
Acylation of alcohols with acetic acid can be carried out efficiently in the liquid phase over microporous titanosilicate ETS-10-type catalysts. The reaction was studied over ETS-10 exchanged with, Li, Na, K, Rb, Cs, Ba and H ions. Activity for acylation of primary alcohols depends on the exchanged alkali ion and increases in the order LiNaKBa～H～Rb～Cs-ETS-10. These molecular sieves are also suitable for the acylation of secondary alcohols and esterification with long chain carboxylic acids.
Process for perfuming textiles
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, (2008/06/13)
We describe a process for perfuming fabrics washed in the presence of a lipase-containing detergent and, optionally, subsequently treated with a fabric softener, said process being characterized in that said detergent and/or said fabric softener contains a compound of formula STR1 wherein a. R represents a radical derived from an fragrant alcohol of formula ROH and Y represents a C7 to C24 linear or branched, saturated or unsaturated alkyl radical, or a --(CH2)n COOR group wherein R is defined as above and n is an integer from 0 to 6; or p1 b. Y represents a C7 to C24 linear or branched, saturated or unsaturated alkyl radical and R represents a group of formula STR2 wherein, either R1 represents hydrogen and R2 represents an alkylidene radical derived from a fragrant aldehyde of formula STR3 or R2 represents an alkylidene radical and R1 an alkyl radical, R1 and R2 being then derived from an fragrant ketone of formula STR4 and, optionally, being part of a ring such as indicated by the dotted line which contains 5 to 18 carbon atoms and can be substituted. The process has the advantage of providing an effect of slow diffusion ("slow release") of said fragrant alcohol, aldehyde or ketone, thus prolonging the odor effect of the latter on fabrics.
