- Reactions of ethylidene diacetate: Formation of N-vinylamide precursors ethylidene bisacetamide and ethylidene bisformamide
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Ethylidene diacetate (EDA) reacts with formamide or acetamide under stoichiometric base or catalytic Lewis acid conditions to afford the corresponding ethylidene bisamides and N-vinylamides. Sn(OAc)2 afforded an overall 82.6% selectivity to the desired acetamide derivatives. Sn(OAc)2 and Zn(OAc)2 facilitate amide attack at the tertiary carbon of EDA.
- Rabasco, John J.,Waller, Francis J.
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Read Online
- Preparation method of N-vinyl alkylamide
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The invention relates to the technical field of vinyl compound production, in particular to a preparation method of Nvinyl alkyl amide. The preparation method comprises the following steps: A) under the action of a composite basic catalyst, reacting acetaldehyde with alkylamide to obtain Nhydroxyethyl alkylamide, and carrying out esterification reaction on the obtained Nhydroxyethyl alkylamide andacid anhydride to obtain an ester compound; wherein the composite basic catalyst comprises an inorganic base and an amine compound; and B) carrying out medium-temperature cracking on the ester compound, and carrying out vacuum distillation to obtain the Nvinyl alkylamide. Research finds that inorganic base and amine compounds are adopted as catalysts at the same time, so that the dosage of a basic catalyst required by reaction of Nhydroxyethyl alkylamide and anhydride can be remarkably reduced, the temperature required by subsequent cracking reaction is reduced, a reaction system tends to bemilder, and the reaction yield is improved. The yield and the purity of a reaction product can be remarkably improved while the energy consumption is reduced.
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Paragraph 0065-0066; 0071-0072
(2020/12/29)
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- SYNTHESIS OF 1-HYDROXYETHYL FORMAMIDES AND N-VINYL FORMAMIDES
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Processes and systems for producing N-vinyl carboxylic acid amides are provided herein. According to some aspects of the present invention, a process for producing an N-vinyl carboxylic acid amide is described that eliminates interim solids handling steps during formation of the intermediate compounds, thereby increasing efficiency and reducing cost. The processes and system described herein may be used for the synthesis of N-vinylformamide and its intermediates, including 1-hydroxyethylformamide and 1- alkoxyethylformamide, or for the synthesis of N-methyl,N-vinylformamide and its intermediates, including N-methyl,1-hydroxyethylformamide and N- methyl,1alkoxyethylformamide.
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Paragraph 0133; 0134
(2018/03/25)
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- N-vinyl amide and used in the production of hydroxylapatite
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PROBLEM TO BE SOLVED: To provide a method for producing an N-vinylamide which attains extremely high conversion and selectivity in the production of an N-vinylamide by dealcoholation reaction of N-(α-alkoxyalkyl)amide, and a catalyst used in the method.SOLUTION: According to the method, an N-vinylamide is produced by subjecting N-(α-alkoxyalkyl)amide to dealcoholation reaction in the presence of a surface-modified apatite catalyst prepared by surface-modifying an apatite represented by general formula (1) with a phosphoric acid compound. (In the formula, M is at least one member selected from the group consisting of Mg, Ca, Sr, Ba, Pb, Mn and Cd; Z is at least one member selected from the group consisting of P, As and Sb; X is at least one member selected from the group consisting of OH, F, Cl, Br, I and At; and 0≤y1).
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Paragraph 0053
(2016/12/26)
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- PROCESS FOR THE PREPARATION OF N-VINYLCARBOXAMIDES
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Process for the preparation of N-vinylcarboxamides by pyrolysis of a compound of the formula [in-line-formulae]CH3—CH(CN)—N(R)—CO—R1 ??(I),[/in-line-formulae]in which R and R1 are H or C1- to C6-alkyl,in the presence of solids which are doped with alkali metal or alkaline earth metal ions, under reduced pressure at a temperature of from 330 to 750° C. with elimination of hydrogen cyanide, cooling, separation and isolation of the reaction products, a solid arranged in a tubular reactor being treated at a temperature in the range from 0 to 250° C. with a solution of an alkali metal and/or alkaline earth metal base, the solution being discharged, the remaining solvent which adheres to the catalyst thus obtainbale being evaporated and said catalyst then being heated to a temperature of at least 380° C. for activation.
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Page/Page column 3-4
(2011/10/13)
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- PROCESS FOR ALKENYLATING CARBOXAMIDES
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The present invention relates to a process for preparing N-(1-alkenyl)carboxamides of the formula I, which comprises reacting a carboxamide of the formula II with an alkyne of the formula III in the presence of a catalyst selected from among carbonyl complexes, halides and oxides of rhenium, manganese, tungsten, molybdenum, chromium and iron.
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Page/Page column 7
(2009/05/28)
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- METHOD FOR PURIFYING POLAR VINYL COMPOUNDS
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Disclosed is a method for purifying an open-chain N-vinyl compound by means of a crystallization process in a crystallizer in which crystallization is performed from a melt of a mixture containing an open-chain N-vinyl compound at a pressure ranging from 10-3 to 400 bar.
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Page/Page column 11-12
(2008/06/13)
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- Methods of making and using surfactant polymers
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Comblike, surfactant polymers for changing the surface properties of biomaterials are provided. Such surfactant polymers comprise a polymeric backbone of repeating monomeric units having functional groups for coupling with side chains, a plurality of hydrophobic side chains linked to said backbone via the functional groups, and a plurality of hydrophilic side chains linked to said backbone via the functional groups. The hydrophobic side chains comprise an alkyl group comprising from 2 to 18 methylene groups. The alkyl groups are linked to the polymeric backbone through ester linkages, secondary amine linkages, or, preferably, amide linkages. The hydrophilic side chain is selected from the group consisting of: a neutral oligosaccharide, which, preferably, has weight average molecular weight of less than 7000; a charged oligosaccharide, preferably a negatively charged oligosaccharide having a weight average molecular weight of less than 10,000; an oligopeptide of from about 3 to about 30 amino acid residues, said oligopeptide having an amino acid sequence which interacts with protein receptors on the surface of cells; and combinations thereof. Methods of making the surfactant polymers and using the surfactant polymers to alter the surface properties of a biomaterial are also provided.
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Page/Page column 4; sheet 1
(2010/02/10)
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- Synthesis of N-vinyl formamide
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A process to produce N-vinylformamide includes the steps of: reacting hydroxyethyl formamide with a reactant comprising at least one cyclic anhydride group to form an ester, and dissociating the ester via heat in a thin film evaporation to synthesize N-vinylformamide and a compound comprising at least one diacid group, the N-vinylformamide separating from the diacid during the thin film evaporation. The reactant including at least one cyclic anhydride group can, for example, be succinic anhydride, maleic anhydride, phthalic anhydride, (2-docecen-1-yl)succinic anhydride, exo-3,6-epoxy-1,2,3,6 -tetrahydrophthalic anhydride or a polymer including at least one cyclic anhydride group. A process to produce N-vinylformamide comprises the steps of: mixing acetaldehyde, formamide and a source of anhydride in a single reaction vessel, reacting the acetaldehyde, formamide and the source of anhydride in the reaction vessel under pressure, dissociating an ester formed by a reaction between the source of anhydride and hydroxyethyl formamide formed in the reaction vessel to synthesize N-vinylformamide and a compound comprising at least one diacid group.
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- SYNTHESIS OF N-VINYL FORMAMIDE
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A process to produce N-vinylformamide includes the steps o£ reacting hydroxyethyl formamide with a reactant including at least one cyclic anhydride group to form an ester, and dissociating (or cracking) the ester to synthesize N-vinylformamide and a compound including at least one diacid group. The ester can be dissociated using heat. The reactant including at least one cyclic anhydride group can, for example, be succinic anhydride, maleic anhydride, phthalic anhydride, a polymer including at least one cyclic anhydride group, or a solid support to which at least one cyclic anhydride group is covalently tethered. Preferably, the cyclic anhydride is regenerated from the diacid formed in the synthesis of the ester by heating the diacid to dehydrate the diacid. The temperature required to dehydrate diacid groups is preferably higher than the temperature use to dissociate the ester.
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- Continuous distillation of thermolabile monomers
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A process for the continuous distillation of thermolabile monomers under reduced pressure in a column includes feeding the thermolabile monomers in vapor or liquid form to the column, introducing an inert distillation aid which forms a heteroazeotrope with the thermolabile monomers into the vaporizer at the bottom of the column, but separately from the monomer feed, and vaporizing into there or feeding an emulsion of thermolabile monomers and an inert distillation aid into the vaporizer or into the column, condensing the azeotrope at the top of the column and separating it in a phase separator, taking off the thermolabile monomers and returning the distillation aid to the column or, if desired, working it up by distillation and taking off components having a higher boiling point than the thermolabile monomers from the bottom of the column.
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- Purification process of N-vinylformamide
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A purification process of N-vinylformamide, which comprises: providing a crude N-vinylformamide having an acetone-insoluble component content of not more than 400 ppm; and continuously feeding the crude N-vinylformamide into a fractionating tower, to obtain an N-vinylformamide having high purity. Also disclose is a continuous purification process of N-vinylformamide, which comprises the steps of: providing a crude N-vinylformamide; feeding the crude N-vinylformamide into a thin film evaporator to remove un-evaporated fraction from the system, and feeding the evaporated fraction containing N-vinylformamide into a fractionating tower, distilling the purified N-vinylformamide from the tower head, and discharging a bottom liquid containing N-vinylformamide from the tower bottom, and recycling the bottom liquid into the thin film evaporator to remove un-evaporated fraction from the system, and feeding the evaporated fraction into the fractionating tower.
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- Preparation of N-alkenyl carboxamides
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Preparation of N-alkenyl carboxamides of the general formula I STR1 in which the radicals R1 to R4 independently stand for hydrogen or for aliphatic, cycloaliphatic, or aromatic radicals, which optionally carry inert substituents, wherein an amide of the general formula II STR2 in which the radical R1 has the above meaning, and a carbonyl compound of the general formula III STR3 in which the radicals R2 to R4 have the above meanings, are caused to react in the presence of a base, said reaction being either a) carried out in the presence of a carboxylic acid derivative of the general formula IV STR4 in which the radical R5 stands for hydrogen or an alkyl or aryl group and X is a halogen, alkoxy, or carboxylalkyl radical, or b) continued in the presence of a carboxylic acid derivative of the formula IV, and the amide of the formula I is isolated.
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- Process for preparing n-vinyl amides
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N-vinyl amides having the general structural formula: wherein R1 is hydrogen, a C1 to C6 alkyl group or C6 -C9 aryl or substituted aryl group, are formed by cracking carboxylic acid amides having the general structure formula: STR1 wherein R1 is as described above, and R2 is a C1 to C9 alkoxy, carboxy or carboxamide group. Said carboxylic acid amides are cracked by heating, to a temperature of about 150°-350° C., in the presence of a porous, hydrogen-abstracting catalyst.
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