Physical and chemical properties of acrylamide polymers and copolymers. Review

Myagchenkov, V. A.; Kurenkov, V. F.

doi:10.1002/actp.1991.010421001

Cited by 13 publications

(18 citation statements)

References 34 publications

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“…Pd(OTs) 2 (dppp) with no additional dppp and p-TsOH gave a low yield (40%) of the unsaturated amides but the high selectivity toward 3 was maintained (94%) ( Table 1, entry 11). Interestingly, the addition of 0.12 mmol of p-TsOH to the previous experiment involving Pd(OTs) 2 (dppp) as a catalyst increased the yield (>90%) of products significantly and the selectivity toward 3 was also kept high (95%). These Materials, Nanoscience and Catalysis 2 (dppb) was also synthesized and used in the carbonylative addition reaction under syngas (CO/H 2 ) in CH 2 Cl 2 as a solvent but in the absence of any additional amount of dppb.…”

Section: Effect Of the Type Of Palladium Complexmentioning

confidence: 89%

“…Interestingly, the addition of 0.12 mmol of p-TsOH to the previous experiment involving Pd(OTs) 2 (dppp) as a catalyst increased the yield (>90%) of products significantly and the selectivity toward 3 was also kept high (95%). These Materials, Nanoscience and Catalysis 2 (dppb) was also synthesized and used in the carbonylative addition reaction under syngas (CO/H 2 ) in CH 2 Cl 2 as a solvent but in the absence of any additional amount of dppb. The yield of the unsaturated amides and the selectivity toward 4 were much lower (41% and 58% respectively) with the formation of palladium black at the end of the reaction due to the decomposition of the palladium complex (Table 1, entry 12).…”

Section: Effect Of the Type Of Palladium Complexmentioning

confidence: 89%

“…Pd(OAc) 2 (0.02 mmol), 1,3-bis(diphenylphosphino)propane (dppp; 0.04 mmol) or dppb (0.08 mmol), p-TsOH (0.12 mmol if used), alkynes (2.0 mmol), aniline derivative (2.0 mmol), and 10 ml of solvent were added into a 45 ml Parr autoclave fitted with a glass liner containing a stirring bar. The autoclave was vented three times with CO and then pressurized at room temperature with 100 psi CO only (or pressurized with 300 psi CO and 300 psi H 2 in the other system).…”

Section: General Procedures For the Carbonylative Coupling Of Terminalmentioning

confidence: 99%

“…The reaction of Pd(OAc) 2 , dppb and H 2 led probably to the palladium dihydride intermediate [(P-P)PdH 2 ] (I) with dppb bidentate to the palladium center (step I). It was mentioned previously that the addition of acetylene to [(Cy 3 P) 2 Pd(H)(HNPh)] yielded the hydrido alkynyl complex, [(Cy 3 P)Pd(H)(CCH)] and aniline, 30 which indicates that the coordination of aniline was unlikely to take place in the reaction under the conditions of system A or B. It is most probable that the coordination of the alkyne (R-CCH) to the palladium center of complex I takes place first to give two possible intermediates, II and III.…”

Section: Proposed Mechanismmentioning

confidence: 99%

“…1 In the last decade, the production of various carbonyl compounds catalyzed by various transition-metal complexes has represented an important and new route in fine chemistry. 2,3 Previously, the synthesis of N-aryl acrylamides was achieved by the reaction of aromatic amines with 2-substituted acryloyl chlorides or substituted acrylic acid. 4 The 2-substituted acrylamides are important intermediates for the synthesis of polymers.…”

mentioning

confidence: 99%

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Catalytic and regioselective synthesis of gem‐ or trans‐α,β‐unsaturated amides by carbonylation of alkyl alkynes with aniline derivatives by palladium(II) and phosphine

Ali¹,

Tijani²

2003

Applied Organom Chemis

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The reaction of carbonylative addition of alkyl alkynes to aniline derivatives has been successfully achieved by a catalytic system formed of Pd(OAc) 2 and a suitable bidentate phosphine ligand. The reaction led mainly to gem-α,β-unsaturated amides (3) with Pd(OAc) 2 /1,3-bis(diphenylphosphino)propane/p-toluenesulfonic acid/CO as the catalytic system. However, the reaction catalyzed by Pd(OAc) 2 /1,4-bis(diphenylphosphino)butane/H 2 /CO in CH 2 Cl 2 as a solvent affords trans-α,β-unsaturated amides (4) as the major product. Copyright  2003 John Wiley & Sons, Ltd.KEYWORDS: carbonylative addition; alkynes; aniline; palladium; dppb; syngas; unsaturated amides INTRODUCTIONThe synthesis of saturated and unsaturated amides is an important area of organic chemistry at the industrial and academic levels. 1 In the last decade, the production of various carbonyl compounds catalyzed by various transition-metal complexes has represented an important and new route in fine chemistry. 2,3 Previously, the synthesis of N-aryl acrylamides was achieved by the reaction of aromatic amines with 2-substituted acryloyl chlorides or substituted acrylic acid. 4 The 2-substituted acrylamides are important intermediates for the synthesis of polymers.5 The direct synthesis of 2-substituted acrylamides from alkynes and amines has previously been reported using various transition-metal complexes. 6 -11 Active soluble palladium complexes are among the most widely used in selective carbonylation chemistry. For example, branched and linear α,β-unsaturated acids and their derivatives are produced by the palladiumcatalyzed carbonylation of alkynes. 12 The regioselectivity depends strongly on the catalytic system and the reaction conditions.12 Branched α,β-unsaturated acids or esters are 23 Only a few reports on palladium complexes as catalysts that can selectively lead to linear unsaturated acid derivatives as the major products have been reported.24,25 Recently, we have described a new and efficient method for the selective production of gem-or trans-α,β-unsaturated amides, esters and thiols. 26 -28 In this paper we report the results of the carbonylative addition of aniline derivatives to various alkyl alkynes producing various new and substituted gem-and trans-α,β-unsaturated amides. The reaction conditions and the catalyst system have a great effect in the inversion of the regioselectivity of the reaction. EXPERIMENTAL GeneralAniline derivatives, alkynes, palladium complexes, phosphine ligands, and carboxylic acids are commercially available materials and were used without any further purification. Materials, Nanoscience and CatalysisDry and freshly distilled solvents have been used in all experiments.1 H NMR and 13 C NMR spectra were recorded on a 500 MHz Joel l500 NMR machine. IR spectra were recorded on a Perkin Elmer 16F PC FT-TR spectrometer and are reported in wavenumbers (cm −1 ). Gas chromatography (GC) analyses were realized on HP 6890 plus chromatography. General procedure for the carbonylative coupling of terminal alkyl alky...

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Section: Effect Of the Type Of Palladium Complexmentioning

confidence: 89%

Section: Effect Of the Type Of Palladium Complexmentioning

confidence: 89%

Section: General Procedures For the Carbonylative Coupling Of Terminalmentioning

confidence: 99%

Section: Proposed Mechanismmentioning

confidence: 99%

mentioning

confidence: 99%

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Catalytic and regioselective synthesis of gem‐ or trans‐α,β‐unsaturated amides by carbonylation of alkyl alkynes with aniline derivatives by palladium(II) and phosphine

Ali¹,

Tijani²

2003

Applied Organom Chemis

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Grafting of polyelectrolytes onto polyacrylamide by reactive processing

Hrymak

Zhu

1999

J. Appl. Polym. Sci.

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Low-molecular-weight high-charge-density cationic poly diallydimethyl ammonium chloride (polyDADMAC) was grafted onto nonionic polyacrylamide (PAM) using organic peroxide initiators in the molten state carried out in a batch mixer. The graft copolymer can be used as a high performance flocculant. Glycerol was selected as a plasticizer. The grafting reaction was characterized in terms of composition, temperature, degree of grafting, and grafting efficiency. It was found that free radicals on polymer chains were induced by the decomposition of the initiator. Grafting was produced by free radical recombination termination. The degree of grafting increases with an increase of the polyDADMAC/PAM feed ratio. However, the grafting efficiency was lower than 10 wt % in this highly viscous polymer melt system.

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Electron spin resonance study and reactive extrusion of polyacrylamide and polydiallyldimethylammonium chloride

Subramanian

Huang

Zhu

et al. 2000

J. Appl. Polym. Sci.

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In this article we report results from an experimental investigation on reactive extrusion of water‐soluble polymers. A polymer system containing homopolymers of diallyldimethylammonium chloride (PolyDADMAC) and acrylamide (PAM) was chosen for this study. Reactive extrusion was performed in a counter‐rotating, tangential twin screw extruder using glycerol as a plasticizer and 2,5‐dimethyl‐2,5‐di‐(t‐butylperoxy) hexene‐3 (Lupersol 130) as an initiator. The effects of three processing parameters (polyDADMAC/PAM weight ratio, extrusion temperature, and residence time) on grafting efficiency and degree of grafting of polyDADMAC on PAM were examined. We found the grafting efficiency of polyDADMAC onto PAM decreased with increasing extrusion temperature, polyDADMAC/PAM weight ratio, and residence time. The degree of grafting of polyDADMAC increased with increasing polyDADMAC/PAM weight ratio, but decreased with increasing extrusion temperature and residence time. The insoluble gel fraction in the extruded copolymer increased with increasing extrusion temperature and residence time, but decreased with increasing polyDADMAC/PAM weight ratio. The chemistry and free radical mechanism of PAM‐peroxide and polyDADMAC‐peroxide systems were studied for three different peroxides using an electron spin resonance technique. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 77: 1154–1164, 2000

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Physical and chemical properties of acrylamide polymers and copolymers. Review

Cited by 13 publications

References 34 publications

Catalytic and regioselective synthesis of gem‐ or trans‐α,β‐unsaturated amides by carbonylation of alkyl alkynes with aniline derivatives by palladium(II) and phosphine

Catalytic and regioselective synthesis of gem‐ or trans‐α,β‐unsaturated amides by carbonylation of alkyl alkynes with aniline derivatives by palladium(II) and phosphine

Grafting of polyelectrolytes onto polyacrylamide by reactive processing

Electron spin resonance study and reactive extrusion of polyacrylamide and polydiallyldimethylammonium chloride

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