12624-24-7

Basic information

• Product Name: Polyacrylamide, anionisch mit einem Restmonomergehalt <0,1 %
• Synonyms: Polyacrylamide, anionisch mit einem Restmonomergehalt
• CAS NO: 12624-24-7
• Molecular Formula: MW:
• Molecular Weight: 0
• Mol File: 12624-24-7.mol
• Article Data: 169

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Polyacrylamide, anionisch mit einem Restmonomergehalt <0,1 %(CAS DataBase Reference)
• NIST Chemistry Reference: Polyacrylamide, anionisch mit einem Restmonomergehalt <0,1 %(12624-24-7)
• EPA Substance Registry System: Polyacrylamide, anionisch mit einem Restmonomergehalt <0,1 %(12624-24-7)

Safety Data

• Hazardous Substances Data: 12624-24-7(Hazardous Substances Data)

Upstream product

• 2651-43-6 3-hydroxypropionamide 
• 15438-67-2 (3-methoxypropyl)amide 
• 107-13-1 acrylonitrile 
• 109-78-4 3-Hydroxypropionitrile 
• 67-64-1 acetone 
• 115-11-7 isobutene 
• 565-00-4 dl-camphene 
• 1147-43-9 2-(2-aminobenzoyl)benzoic acid 
• 7732-18-5 water 
• 814-68-6 acryloyl chloride 
• 814-49-3 diethyl chlorophosphate 
• 107-11-9 1-amino-2-propene 
• 79-10-7 acrylic acid 
• 96-96-8 4-methoxy-2-nitroaniline 

Downstream Products

• 100705-42-8 3-(2-isopropyl-benzimidazol-1-yl)-propionic acid amide 
• 10333-11-6 3,4,5,6,7,8-hexahydro-2-quinolinone 
• 4091-84-3 N-phenethyl-β-alanine amide 
• 16328-30-6 N-(2,2,2-trichloro-1-hydroxy-ethyl)-acrylamide 
• 58089-44-4 3-(N'-Methyl-N'-phenyl-hydrazino)-propionamide 
• 5337-30-4 diethyldithiocarbamic acid 2-carbamoylethyl ester 
• 10333-13-8 1Δ^4a(7a)-hexahydro-2(1H)-pyrindone 
• 24438-88-8 3-(pyrrolidin-1-yl)propanamide 
• 5337-31-5 morpholine-4-carbodithioic acid-(2-carbamoyl-ethyl ester) 
• 296761-14-3 3-[2-(dimethylamino)ethoxy]propionamide 
• 103284-48-6 3-octyl-3-(4-pyrido)piperidine-2,6-dione 
• 57963-11-8 4,5-dimethyl-2-aminopyridine 
• 4269-30-1 3-(1-piperidinyl)-propionamide 
• 5165-28-6 5,5-dimethyl-2-pyrrolidone 

Relevant articles and documents

Synthesis of glycidamide from acrylonitrile using basic hydrotalcite catalyst in the presence of aqueous hydrogen peroxide and unsaturated amide

Glycidamide (GA) can be synthesized from acrylonitrile (AN) by using hydrotalcite as a solid base catalyst and 25% aqueous H2O2 as an oxidant, in the presence of acrylam ide (AA) as a cocatalyst in methanol solvent at 313K for 18 h. The GA yield and H2O2 utilization efficiency reached 74% and 60%, respectively. The hydrotalcite catalyst could be easily separated from the reaction mixture and reused at least once.

Nanoscopic Naked Cu/Pd Powder as Air-Resistant Active Catalyst for Selective Hydration of Acrylonitrile to Acrylamide

Nanoscopic naked Cu/Pd alloy powders, particle size in 1-5 nm, were prepared by a cold alloying process.The formation of nanoscopic bimetallic hydroxide colloids as precursors of the nanoscopic alloy powders was studied by means of TEM, XRD, and a titration method.These bimetallic alloy powders have provided the first example of Cu-based catalysts with high activity, selectivity, and stability against air for the selective hydration of acrylonitrile to acrylamide.

DJ-1 family Maillard deglycases prevent acrylamide formation

The presence of acrylamide in food is a worldwide concern because it is carcinogenic, reprotoxic and neurotoxic. Acrylamide is generated in the Maillard reaction via condensation of reducing sugars and glyoxals arising from their decomposition, with asparagine, the amino acid forming the backbone of the acrylamide molecule. We reported recently the discovery of the Maillard deglycases (DJ-1/Park7 and its prokaryotic homologs) which degrade Maillard adducts formed between glyoxals and lysine or arginine amino groups, and prevent glycation damage in proteins. Here, we show that these deglycases prevent acrylamide formation, likely by degrading asparagine/glyoxal Maillard adducts. We also report the discovery of a deglycase from the hyperthermophilic archaea Pyrococcus furiosus, which prevents acrylamide formation at 100?°C. Thus, Maillard deglycases constitute a unique enzymatic method to prevent acrylamide formation in food without depleting the components (asparagine and sugars) responsible for its formation.

Water soluble diphosphine ligands based on 1,3,5-triaza-7-phosphaadamantane (PTA-PR2): Synthesis, coordination chemistry, and ruthenium catalyzed nitrile hydration

Two chiral chelating 1,3,5-triaza-7-phosphaadamantane (PTA) derivatives were synthesized, in racemic form, by addition of ClPiPr2 or ClP(NiPr)2(CH2)2 to lithiated PTA. PTA-PiPr2 (1) and PTA-P(NiPr)2(CH2)2 (2) were isolated in good yield, 73% and 56% respectively, and fully characterized by multinuclear NMR spectroscopy, mass spectrometry, and X-ray crystallography. PTA-PiPr2 is highly air sensitive, but stable and somewhat soluble in degassed water. PTA-P(NiPr)2(CH2)2 (2) is air-stable, but decomposes in water over the course of hours. Two tungsten tetracarbonyl complexes were prepared by addition of the PTA-PR2 to [W(CO)4(pip)2] and characterized by NMR and IR spectroscopies and X-ray crystallography in the case of [W(CO)4(PTA-PiPr2)]. Based on IR spectroscopy PTA-PiPr2 (1) is more electron donating than PTA-P(NiPr)2(CH2)2 (2) or the previously published PTA-PPh2. Products isolated from the reaction of [(η6-toluene)RuCl2]2 with two equivalents of 1 were found to contain monodentate (κ1), bidentate (κ2), and possibly bridging coordination modes of PTA-PiPr2. These ruthenium complexes were explored as catalysts for aqueous phase nitrile hydration. Of the ruthenium complexes explored [(η6-toluene)RuCl2(κ1-PTA-PiPr2)] (7) was the most active towards nitrile hydration. In the presence of air at 100°C 7 converted various nitriles to the respective amides with 43-99% conversions in 7 h.

Aqueous and biphasic nitrile hydration catalyzed by a recyclable Ru(ii) complex under atmospheric conditions

[RuCl2(PTA)4] (PTA = 1,3,5-triaza-7- phosphaadamantane) was found to be a highly active catalyst for aqueous phase nitrile hydration at 100 °C in air. Near quantitative conversion of aromatic, alkyl, and vinyl nitriles to their corresponding amides was observed. The reaction tolerated ether, hydroxyl, nitro, bromo, formyl, pyridyl, benzyl, alkyl, and olefinic functional groups. Some amides were isolated by simple decantation from the aqueous phase catalyst. Catalyst loading down to 0.001 mol% was examined with turnover numbers as high as 22000 observed. The catalyst was stable for weeks in solution and could be reused more than five times without significant loss of activity.

Hydration of Nitriles to Amides by Thiolate-Bridged Diiron Complexes

A series of nitrile-coordinating complexes [CpFe(μ-SEt)RCN]2[PF6]2 (1, R = alkyl, aryl, vinyl, amine) have been obtained by the reaction of [CpFe(μ-SEt)MeCN]2[PF6]2 (1a) with various nitriles in acetone. Complexes 1 can realize the hydration of a nitrile ligand under ambient conditions. Complexes [CpFe(μ-SEt)2(μ-η1:η1-NH(O)CR)FeCp][PF6] (2) were successfully isolated as intermediates during the hydration process, with 2b and 2e (R = CH2i = CH and Et2N) being characterized by spectrometry and X-ray crystallography. Treatment of 2 with HBF4·Et2O in the presence of nitriles released corresponding amides 3. At the same time, the structural features of the [Fe2S2] scaffold were retained. These results confirmed that the hydration of nitriles was realized by cooperative interaction on diiron centers. (Figure Presented).

Silica-sulfuric acid: Novel, simple, efficient and reusable catalyst for hydration of nitrile to amide

Silica-sulfuric acid efficiently catalyzes conversion of aliphatic, substituted aromatic and hetero aromatic nitriles to their corresponding amides in good to excellent yields under reflux condition. Products obtained were purified by column chromatography method and characterized by 1H NMR, 13C NMR and mass spectral analysis.

Pyrrolopyrimidine vs Imidazole-Phenyl-Thiazole Scaffolds in Nonpeptidic Dimerization Inhibitors of Leishmania infantum Trypanothione Reductase

Disruption of protein-protein interactions of essential oligomeric enzymes by small molecules represents a significant challenge. We recently reported some linear and cyclic peptides derived from an α-helical region present in the homodimeric interface of Leishmania infantum trypanothione reductase (Li-TryR) that showed potent effects on both dimerization and redox activity of this essential enzyme. Here, we describe our first steps toward the design of nonpeptidic small-molecule Li-TryR dimerization disruptors using a proteomimetic approach. The pyrrolopyrimidine and the 5-6-5 imidazole-phenyl-thiazole α-helix-mimetic scaffolds were suitably decorated with substituents that could mimic three key residues (K, Q, and I) of the linear peptide prototype (PKIIQSVGIS-Nle-K-Nle). Extensive optimization of previously described synthetic methodologies was required. A library of 15 compounds bearing different hydrophobic alkyl and aromatic substituents was synthesized. The imidazole-phenyl-thiazole-based analogues outperformed the pyrrolopyrimidine-based derivatives in both inhibiting the enzyme and killing extracellular and intracellular parasites in cell culture. The most active imidazole-phenyl-thiazole compounds 3e and 3f inhibit Li-TryR and prevent growth of the parasites at low micromolar concentrations similar to those required by the peptide prototype. The intrinsic fluorescence of these compounds inside the parasites visually demonstrates their good permeability in comparison with previous peptide-based Li-TryR dimerization disruptors.

Kinetics of acrylamide formation and elimination during heating of an asparagine-sugar model system

The kinetics of acrylamide (AA) was analyzed by heating a simple model system consisting of asparagine and glucose, fructose, or sucrose (0.01 M, pH 6) at temperatures between 140 and 200 °C. The AA concentration appeared to be the net result of simultaneous formation and elimination. A general kinetic model describing the AA yield was identified, and kinetic parameters were obtained by nonlinear regression on the nonisothermally derived data. On the basis of kinetic parameters, the AA formation appeared to proceed faster and to be more temperature sensitive in the asparagine-glucose than in the asparagine-fructose model system. The AA elimination kinetics, on the other hand, was similar. Significantly less AA was formed in the asparagine-sucrose model system as compared to the model systems with glucose or fructose.

Ru(ii)-dmso complexes containing azole-based ligands: Synthesis, linkage isomerism and catalytic behaviour

The reaction of cis,fac-[RuCl2(dmso-S)3(dmso-O)], 1, with different azole (L) ligands leads to new [RuCl2(L)(dmso-S)3] compounds (L = CH3-pz-H, 2; NO2-pz-H, 3; CF3-pz-H, 4 and Br-Hind, 5). Complexes 2-5 have been characterized by analytical, spectroscopic and electrochemical techniques as well as by monocrystal X-ray diffraction analysis. Upon oxidation to Ru(iii) the complexes undergo linkage isomerization of a S-bound dmso ligand and the corresponding kinetic rates as well as the thermodynamic properties have been determined for compound 2 and also for the previously described [RuIICl2(pypz-H)(dmso-S)2] (pypz-H = 2-(3-pyrazolyl)pyridine), 6, from cyclic voltammetries performed at different scan rates. The exposure of compound 2 to visible light in acetonitrile produces the substitution of one dmso ligand by a solvent molecule generating a new compound, 2′. The irradiation of solutions of compounds 2 and 6 in chloroform leads in both cases to the substitution of one dmso by a chlorido ligand in parallel to the oxidation of Ru(ii) to Ru(iii) generating complexes 2′′ and 6′ respectively. The reactivity of compounds 2-6 has been tested with regard to the hydration of nitriles in water as a solvent, displaying in all cases good performance and selectivity for the corresponding amides.

Impact of pH on the kinetics of acrylamide formation/elimination reactions in model systems

The effect of pH on acrylamide formation and elimination kinetics was studied in an equimolar (0.1 M) asparagine-glucose model system in phosphate or citrate buffer, heated at temperatures between 120 and 200°C. To describe the experimental data, a simplified kinetic model was proposed and kinetic parameters were estimated by combined nonlinear regression and numerical integration on the data obtained under nonisothermal conditions. The model was subsequently validated in a more realistic potato-based matrix with varying pH. By increasing acidity, the reaction rate constants at Tref (160°C) for both acrylamide formation and elimination can significantly be reduced, whereas the temperature dependence of both reaction rate constants increases. The introduction of a lyophilized potato matrix (20%) did not affect the acrylamide formation reaction rate constant at reference temperature (160°C) as compared to the asparagine-glucose model system; the elimination rate constant at Tref, on the contrary, was almost doubled.

Acrylamide production using encapsulated nitrile hydratase from Pseudonocardia thermophila in a sol-gel matrix

The cobalt-type nitrile hydratase from Pseudonocardia thermophila JCM 3095 (PtNHase) was successfully encapsulated in tetramethyl orthosilicate sol-gel matrices to produce a PtNHase:sol-gel biomaterial. The PtNHase:sol-gel biomaterial catalyzed the conversion of 600 mM acrylonitrile to acrylamide in 60 min at 35 C with a yields of >90%. Treatment of the biomaterial with proteases confirmed that the catalytic activity is due to the encapsulated enzyme and not surface bound NHase. The biomaterial retained 50% of its activity after being used for a total of 13 consecutive reactions for the conversion of acrylonitrile to acrylamide. The thermostability and long-term storage of the PtNHase:sol-gel are substantially improved compared to the soluble NHase. Additionally, the biomaterial is significantly more stable at high concentrations of methanol (50% and 70%, v/v) as a co-solvent for the hydration of acrylonitrile than native PtNHase. These data indicate that PtNHase:sol-gel biomaterials can be used to develop new synthetic avenues involving nitriles as starting materials given that the conversion of the nitrile moiety to the corresponding amide occurs under mild temperature and pH conditions.

Neutral Regioselective Copper-Catalyzed Hydration of Some Nitriles to Amides

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Magnetically separable and Recyclable Fe3O4-supported Ag Nanocatalysts for reduction of nitro compounds and selective Hydration of Nitriles to Amides in Water

As hybrid nanostructures have become more important in many fields of chemistry, Ag nanoparticles (NPs) are being increasingly immobilized onto Fe3O4 microspheres in situ. Structural characterization reveals that the Ag NPs are uniformly immobilized in the Fe3O 4 microsphere-based supports. Moreover, Ag NPs are more stable in the hybrid structure than in the naked state and show high catalytic activity for the reduction of nitro compounds and hydration of nitriles to amides in water. The Fe3O4 microspheres were recycled several times using an external magnet.

A Heterogeneous Ruthenium dmso Complex Supported onto Silica Particles as a Recyclable Catalyst for the Efficient Hydration of Nitriles in Aqueous Medium

In the present work, we describe an efficient method for the covalent anchoring of a Ru-dmso complex onto two types of supports: mesoporous silica particles (SP) and silica coated magnetic particles (MSNP). First, we have prepared and characterized the molecular complexes containing the bidentate pyridylpyrazole ligands pypz-Me and pypz-CH2COOEt, with the formula [RuIICl2(pypz-R)(dmso)2] (R = Me, 1; CH2COOEt, 2). Complex 2 was anchored onto the silica supports, yielding the heterogeneous systems SP@2 and MSNP@2 which were fully characterized by IR, UV-vis, SEM, TEM, TGA, and XPS techniques. Hydration of representative nitriles has been tested with the molecular complexes and their SP@2 and MSNP@2 heterogeneous counterparts, in aqueous medium under neutral conditions. The heterogeneous catalysts display high yields and excellent selectivity values. Both systems can be reused throughout several cycles for benzonitrile and acrylonitrile substrates, without any significant loss in reactivity. The MSNP@2 material can be easily recovered by a magnet, facilitating its reusability.

Role of curcumin in the conversion of asparagine into acrylamide during heating

This study aimed to investigate the ability of curcumin to convert asparagine into acrylamide during heating at different temperatures. Binary and ternary model systems of asparagine-curcumin and asparagine-curcumin-fructose were used to determine the role of curcumin on acrylamide formation in competitive and uncompetitive reaction conditions. The results indicated that curcumin could potentially contribute to acrylamide formation under long-term heating conditions as long as asparagine was present in the medium. The amount of acrylamide formed in the ternary system was slightly higher than in the binary system during heating (p a carbonyl compound can react directly with ASN leading to acrylamide. The addition of antioxidants to foods may increase the formation of acrylamide upon long-term heating if free sugar concentration is low and ASN concentration is relatively high.

Quantitation of 3-aminopropionamide in potatoes - A minor but potent precursor in acrylamide formation

3-Aminopropionamide (3-APA) has recently been suggested as a transient intermediate in acrylamide (AA) formation during thermal degradation of asparagine initiated by reducing carbohydrates or aldehydes, respectively. 3-APA may also be formed in foods by an enzymatic decarboxylation of asparagine. Using a newly developed method to quantify 3-APA based on liquid chromatography/ tandem mass spectrometry, it could be shown that the biogenic amine was present in several potato cultivars in different amounts. Further experiments indicated that 3-APA is formed during storage of intact potatoes (20 or 35 °C) or after crushing of the cells. The heating of 3-APA under aqueous or low water conditions at temperatures between 100 and 180 °C in model systems always generated more AA than in the same reaction of asparagine, thereby pointing to 3-APA as a very effective precursor of AA. While the highest yields measured were about 28 mol % in the presence of carbohydrates (170 °C; aqueous buffer), in the absence of carbohydrates, 3-APA was even converted by about 63 mol % into AA upon heating at 170 °C under aqueous conditions. Propanoic acid amides bearing an amino or hydroxy group in the α-position, such as 2-hydroxypropionamide and L-alaninamide, were ineffective in AA generation indicating that elimination occurs only from the β-position.

REGIOSELECTIVE HYDRATION OF ACRYLONITRILE TO GIVE ACRYLAMIDE CATALYZED BY (Pd(OH)2(BIPYRIDINE)(H2O))

Satisfactory yields were observed for the selective hydration of acrylonitrile to give acrylamide when using the complex (Pd(OH)2(bipy)(H2O))

INFLUENCE OF ALLOYING ON THE HYDRATION OF ACRYLONITRILE TO ACRYLAMIDE BY COPPER-NICKEL ALLOY CATALYSTS

The liquid phase hydration of acrylonitrile to acrylamide was studied over the Cu-Ni alloy catalysts with various compositions.The maximum synergestic effect was observed over the alloy with the surface component ratio of Cu to Ni of 4.

Reactivity of secondary N-alkyl acrylamides in Morita–Baylis–Hillman reactions

The Morita–Baylis–Hillman (MBH) reaction of secondary N-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a 1:1 water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary N-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.

Pyridine-Enabled C-N Bond Activation for the Rapid Construction of Amides and 4-Pyridylglyoxamides by Cooperative Palladium/Copper Catalysis

A pyridine-enabled C-N bond activation of peptidomimetics employing cooperative palladium/copper catalysis in water is developed. Diverse amides and 4-pyridylglyoxamides are simultaneously synthesized through two steps from commercially available materials in a rapid, environmentally friendly, and high atom-economical manner.