4,083,699 and 4,006,089 are directed respectively to fuel compositions and additive products useful therein and to lubricant compositions comprising a Mannich base reaction product of a high molecular weight alkyl substituted hydroxy aromatic compound, a polyoxyethylene polyamine and an aldehyde useful as detergency agents in various fuels and lubricants. Introduction of unsaturation adjacent to the carbonyl drastically improves the reactivity of the Zn-ProPhenol catalyzed Mannich reactions between N-carbamoyl imines and a-branched ketones. The mechanism of the Mannich reaction starts with the formation of an iminium ion from the amine and the formaldehyde. Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. the Altmetric Attention Score and how the score is calculated. It is emphasized that the relative boiling point of the amine from which the Mannich base is prepared must have a lower boiling point than the reactive amine, thiol or dithiophosphoric acid compounds used in displacement reaction. formaldehyde and dimethylaminium chloride. Thermo-reactive polymers with a poly-(p-phenylenoxide) structure produced from bis-phenols and formaldehyde. For example, other corrosion inhibitors, extreme pressure agents, antiwear agents, defoamants, detergents, dispersants, and the like can be used. Cyclic imine derivatives that react with phenols, including tyrosine residues of peptides, have been developed. -butylcardanol) polymerization of pyrrole. The Mannich reaction involves several acid-catalysed equilibria. The product was stripped of solvent and used without further purification. can be conveniently eliminated to acrylophenone (1-phenylprop-2-en-1-one), an The Mannich reaction is an organic reaction which consists of an amino alkylation of an acidic proton placed next to a carbonyl functional group by formaldehyde and a primary or secondary amine or ammonia. Briefly, the modified Mannich reaction products of this invention can be produced by reacting oxidized polymer, the amine, and formaldehyde yielding reagent in the presence of an oil soluble phenol at a temperature of about 250°-350° F. and recovering the resulting reaction product. Suitable exemplary thiols include alkanethiols like methanethiol, ethanethiol, and any higher alkanethiol; arylthiols like benzenethiol, 2-naphthalenethiol; cycloalkanethiols like cyclohexanethiol, cyclohexanemethanethiol; alkarylthiols like benzenemethanethiol; aralkylthiols like toluenethiol, and the like having from 1 to about 30 carbon atoms (C1 -C30). Your Mendeley pairing has expired. Despite only a small change in the substrate acidity, the bimetallic catalyst can preferentially recognize and activate unsaturated ketones over their fully saturated counterparts, providing a chemo-, diastereo … A11 the Mannich bases were examined by H nuclear magnetic resonance, infra-red spectroscopy and by T. L. C. Use the link below to share a full-text version of this article with your friends and colleagues. It is also possible to use activated phenyl groups and electron-rich heterocycles such as furan, pyrrole, and thiophene. This salt exists in equilibrium with the free amine and proton. Oleaginous materials are highly susceptible to chemical action on aging, exposure to sunlight, and in their normal use. The ability to carry out this transformation in water makes it even more attractive and no wonder that this fact has gained significant attention of chemical society. shown below. In all cases the sum of the residuals was smaller when the kinetic expression derived assuming participation of the aminal was employed. Please check your email for instructions on resetting your password. 3) In the following example of Mannich reaction, the * The α-CH acidic compounds include carbonyl compounds, nitriles, aliphatic nitro compounds, alkynes, α-alkyl-pyridines or imines, activated Direct multicomponent reaction for CC bond formation performed in water. Nos. The phenols that are contemplated have the following generalized formula: ##STR2## where R2 and R3 are the same or different and may be hydrogen or an alkyl group containing 1 to about 18 carbon atoms, and preferably are tertiary alkyl groups. is used as a source of formaldehyde and dimethyl amine for Mannich reactions. Like the aldol condensation, the success of the Mannich reaction depends on being able to generate both nucleophilic and electrophilic carbons in the reaction mixture at the same time. Tertiary amines lack an N–H proton to form the intermediate enamine. Generally speaking, the preformed Mannich base and the HY component or reactive amine, thior or dithiophosphoric acid are usually reacted in molar ratios of HY component to Mannich base of 1 to 1 to about 2 to 1. Quail, U Pugazhenthi, S.A. Arpin, S.J. the iminium ion at positively charged carbon adjacent to nitrogen to give Note: Phenolic Mannich bases other than Ethyl 703 have been used. In the search for high yielding, sustainable and green transformations leading to desired products with high level of structural complexity and desired functionality, the multicomponent reactions appear as very promising alternative.


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