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Analytica Chimica Acta Apr 2022As an example of extending the functionality of analytical devices manufactured using four-dimensional printing (4DP), in this study we employed acrylonitrile butadiene...
As an example of extending the functionality of analytical devices manufactured using four-dimensional printing (4DP), in this study we employed acrylonitrile butadiene styrene (ABS) thermoplastic filaments, poly(4-vinylpyridine) (P4VP)-incorporated ABS filaments, and multi-material fused deposition modeling three-dimensional printing (3DP) to fabricate a pH measurement device that underwent pH-dependent geometric changes. Upon immersion in a solution having a pH close to the value of pK of P4VP (ca. 5.0), electrostatic repulsion among the protonated units of P4VP resulted in swelling only of the part printed using the P4VP-incorporated ABS filaments, leading to lifting of the whole device along the z-axis (ΔH) in a pH-dependent manner. After optimizing the device's design and fabrication, this 4D-printed pH sensing claw exhibited linearity between the value of ΔH and values of pH in the range from 5.0 to 8.6. We used this 4D-printed pH sensing claw to perform pH analyses of complicated real samples, verifying its analytical reliability for non-electrochemical and non-optical pH measurement and highlighting the capability of 4DP technologies in the direct fabrication of stimuli-responsive sensing devices. We envision that 4DP technologies will prompt the manufacture of smart sensing devices through the printing of stimuli-responsive materials, thereby diversifying the development of 3DP-enabling analytical chemistry.
Topics: Acrylonitrile; Hydrogen-Ion Concentration; Polymers; Printing, Three-Dimensional; Reproducibility of Results
PubMed: 35397904
DOI: 10.1016/j.aca.2022.339733 -
Journal of Food Science Dec 2023This study validated an analytical technique using headspace gas chromatography with flame ionization detection to quantify acrylonitrile monomer with a quantification...
This study validated an analytical technique using headspace gas chromatography with flame ionization detection to quantify acrylonitrile monomer with a quantification limit of 0.10 ± 0.04 µg kg . Subsequently, the acrylonitrile migration from polypropylene granules was evaluated in food simulants water and ethanol (50% v/v) and at two temperatures (20 ± 1°C and 44 ± 2°C) for up to 6 weeks, representing the service time of a bottle. From the experimental data obtained, pseudo-second-order kinetics were adjusted to represent the acrylonitrile migration into the simulants. For water, equilibrium concentrations of 13.58 and 16.58 µg kg at 20 and 44°C, respectively, were obtained, while for 50% ethanol, 15.07 and 16.40 µg kg were obtained for the same temperatures. The experimental results and the values estimated from the migration kinetics indicate that the maximum acrylonitrile concentration will not exceed the tolerable specific limit established in regulations. PRACTICAL APPLICATION: The migration of compounds such as acrylonitrile can be a drawback resulting in an undesirable reduction in the shelf life of liquid foods packaged in bottles made of materials such as polypropylene. In this paper, acrylonitrile migration kinetics and a methodology are proposed to determine whether the tolerable migration limits are ever reached, which can serve as a tool for producers of this type of packaging of food to predict shelf life.
Topics: Food Packaging; Polypropylenes; Acrylonitrile; Ethanol; Water; Food Contamination
PubMed: 37905708
DOI: 10.1111/1750-3841.16819 -
Scientific Reports Apr 2023In this work, five acrylonitrile adducts were screened for antibacterial activity against Gram-positive Bacillus subtilis, Microbial Type Culture Collection and Gene...
In this work, five acrylonitrile adducts were screened for antibacterial activity against Gram-positive Bacillus subtilis, Microbial Type Culture Collection and Gene Bank (MTCC 1305) and Gram-negative Escherichia coli (MTCC 443). Synthesis was followed by aza-Michael addition reaction, where the acrylonitrile accepts an electron pair from the respective amines and results in the formation of n-alkyliminobis-propionitrile and n-alkyliminopropionitrile under microwave irradiation. Characterization of the compounds were performed using Fourier Transform Infrared (FTIR), Proton Nuclear Magnetic Resonance (H NMR) and Electrospray Ionisation Mass Spectrometry (ESI-MS). The particle size characterization was done by Dynamic Light Scattering (DLS) technique. The antibacterial study showed higher inhibition rate for both Gram-positive and Gram-negative bacteria. The antibacterial ability was found to be dose dependent. The minimum inhibitory concentration against both bacteria were found to be 1, 3, 0.4, 1, 3 µl/ml for E. coli and 6, 6, 0.9, 0.5, 5 µl/ml for B. subtilis. Time-kill kinetics evaluation showed that the adducts possess bacteriostatic action. Further it was evaluated for high-throughput in vitro assays to determine the compatibility of the adducts for drug delivery. The haemolytic and thrombolytic activity was analysed against normal mouse erythrocytes. The haemolytic activity showed prominent results, and thereby projecting this acrylonitrile adducts as potent antimicrobial and haemolytic agent.
Topics: Animals; Mice; Anti-Bacterial Agents; Acrylonitrile; Fibrinolytic Agents; Escherichia coli; Gram-Negative Bacteria; Anti-Infective Agents; Microbial Sensitivity Tests; Bacillus subtilis
PubMed: 37069316
DOI: 10.1038/s41598-023-33605-1 -
Molecules (Basel, Switzerland) Mar 2022Five focused compound libraries (forty-nine compounds), based on prior studies in our laboratory were synthesized and screened for antibiotic and anti-fungal activity...
Five focused compound libraries (forty-nine compounds), based on prior studies in our laboratory were synthesized and screened for antibiotic and anti-fungal activity against S. aureus, E. coli, K. pneumoniae, P. aeruginosa, A. baumannii, C. albicans and C. neoformans. Low levels of activity, at the initial screening concentration of 32 μg/mL, were noted with analogues of (Z)-2-(3,4-dichlorophenyl)-3-phenylacrylonitriles which made up the first two focused libraries produced. The most promising analogues possessing additional substituents on the terminal aromatic ring of the synthesised acrylonitriles. Modifications of the terminal aromatic moiety were explored through epoxide installation flowed by flow chemistry mediated ring opening aminolysis with discreet sets of amines to the corresponding amino alcohols. Three new focused libraries were developed from substituted anilines, cyclic amines, and phenyl linked heterocyclic amines. The aniline-based compounds were inactive against the bacterial and fungal lines screened. The introduction of a cyclic, such as piperidine, piperazine, or morpholine, showed >50% inhibition when evaluated at 32 μg/mL compound concentration against methicillin-resistant Staphylococcus aureus. Examination of the terminal aromatic substituent via oxirane aminolysis allowed for the synthesis of three new focused libraries of afforded amino alcohols. Aromatic substituted piperidine or piperazine switched library activity from antibacterial to anti-fungal activity with ((Z)-2-(3,4-dichlorophenyl)-3-(4-(2-hydroxy-3-(4-methylpiperazin-1-yl)propoxy)phenyl)acrylonitrile), ((Z)-2-(3,4-dichlorophenyl)-3-(4-(2-hydroxy-3-(4-(4-hydroxyphenyl)piperazin-1-yl)propoxy)-phenyl)acrylonitrile) and ((Z)-3-(4-(3-(4-cyclohexylpiperazin-1-yl)-2-hydroxypropoxy)-phenyl)-2-(3,4-dichlorophenyl)-acrylonitrile) showing >95% inhibition of Cryptococcus neoformans var. grubii H99 growth at 32 μg/mL. While (Z)-3-(4-(3-(cyclohexylamino)-2-hydroxypropoxy)phenyl)-2-(3,4-dichlorophenyl)-acrylonitrile, (S,Z)-2-(3,4-dichlorophenyl)-3-(4-(2-hydroxy-3-(piperidin-1-yl)propoxy)phenyl)acrylonitrile, (R,Z)-2-(3,4-dichlorophenyl)-3-(4-(2-hydroxy-3-(piperidin-1-yl)propoxy)phenyl)acrylonitrile, (Z)-2-(3,4-dichlorophenyl)-3-(4-(2-hydroxy-3-(D-11-piperidin-1-yl)propoxy)phenyl)-acrylonitrile, and (Z)-3-(4-(3-(4-cyclohexylpiperazin-1-yl)-2-hydroxypropoxy)-phenyl)-2-(3,4-dichlorophenyl)-acrylonitrile 32 μg/mL against Staphylococcus aureus.
Topics: Acrylonitrile; Amino Alcohols; Anti-Bacterial Agents; Antifungal Agents; Escherichia coli; Klebsiella pneumoniae; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Piperazine; Pseudomonas aeruginosa; Staphylococcus aureus; Structure-Activity Relationship
PubMed: 35408448
DOI: 10.3390/molecules27072050 -
The Journal of Organic Chemistry Oct 2022Azido nucleosides couple with phosphoramidites via an initial iminophosphorane, which eliminates acrylonitrile to generate the coupled dimer P(V) product. The vulnerable...
Azido nucleosides couple with phosphoramidites via an initial iminophosphorane, which eliminates acrylonitrile to generate the coupled dimer P(V) product. The vulnerable phosphite triester intermediate is bypassed entirely, making the methodology very suitable to solution-phase synthesis. This new coupling protocol requires no protection of the 5'-OH function and provides a new method of installing internucleosidic phosphorodiamidate bonds with near quantitative yields.
Topics: Acrylonitrile; Nucleosides; Oligonucleotides; Phosphites; Polymers
PubMed: 36161801
DOI: 10.1021/acs.joc.2c01582 -
Chemosphere Nov 2022Micro/nanoplastics (MNPs) are widespread environmental pollutants that cause high health risks. However, high heterogeneity in particle sizes and chemical compositions...
Micro/nanoplastics (MNPs) are widespread environmental pollutants that cause high health risks. However, high heterogeneity in particle sizes and chemical compositions of MNPs make their accurate characterization extremely challenging. Herein, we established a matrix-assisted laser desorption ionization-Fourier transform ion cyclotron resonance mass spectrometry (MALDI-FTICR MS) strategy for the unambiguous characterization of different types of MNPs with high performance, including polystyrene, polyethylene glycol terephthalate, polyamide, polymethyl methacrylate, acrylonitrile butadiene styrene copolymer, and polycarbonate. The MNP sample preparation and detection conditions were systematically optimized by using response surface methodology, and the MS detection signal-to-noise ratios were improved 1.5 times on average. The ultrahigh mass resolution of FTICR MS is crucial to the unambiguous elucidation of MNP structures. We demonstrate that this MS strategy is highly efficient in the characterization of polymer constitutions of environmental MNPs derived from foam, bottles, cable ties, and compact discs, providing a promising tool for MNP detection and safety evaluation.
Topics: Acrylonitrile; Butadienes; Environmental Pollutants; Fourier Analysis; Microplastics; Nylons; Polyethylene Glycols; Polymers; Polymethyl Methacrylate; Polystyrenes; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
PubMed: 35817191
DOI: 10.1016/j.chemosphere.2022.135601 -
Chemico-biological Interactions Jun 2022Acrylonitrile is an organic chemical synthetic monomer that is widely used in food packaging and manufacturing. Animal studies have reported that acrylonitrile is...
Acrylonitrile is an organic chemical synthetic monomer that is widely used in food packaging and manufacturing. Animal studies have reported that acrylonitrile is carcinogenic and toxic, but the effects on the female reproductive function in mammals are unknown. In the present study, we report that acrylonitrile treatment affects ovarian homeostasis in mice, resulting in impaired follicular development. Follicles in acrylonitrile-exposed mice exhibited high levels of inflammation and apoptosis, and acrylonitrile treatment interfered with oocyte development. Transcriptomics analysis showed that acrylonitrile altered the expression of oocyte genes related to apoptosis, oxidative stress, endoplasmic reticulum stress, and autophagy. Further molecular tests revealed that acrylonitrile induced early apoptosis, DNA damage, elevated levels of reactive oxygen species, endoplasmic reticulum abnormalities, and lysosomal aggregation. We also observed disruption of mitochondrial structure and distribution and depolarization of membrane potential. Finally, acrylonitrile treatment in female mice decreased the number and weight of offspring. Altogether, these findings suggest that acrylonitrile impairs the stability of the ovarian internal environment, which in turn affects oocyte development and reduces the number of offspring.
Topics: Acrylonitrile; Animals; Apoptosis; Female; Inflammation; Mammals; Mice; Mitochondria; Oocytes
PubMed: 35429547
DOI: 10.1016/j.cbi.2022.109934 -
International Journal of Occupational... Dec 2022. This study aimed to assess carcinogenic and health risks of respiratory exposure to acrylonitrile, 1,3-butadiene and styrene (ABS) in the petrochemical industry. ....
Carcinogenic and health risk assessment of respiratory exposure to acrylonitrile, 1,3-butadiene and styrene in the petrochemical industry using the US Environmental Protection Agency method.
. This study aimed to assess carcinogenic and health risks of respiratory exposure to acrylonitrile, 1,3-butadiene and styrene (ABS) in the petrochemical industry. . This cross-sectional study was conducted in a petrochemical plant producing ABS copolymers. Respiratory exposure to each of acrylonitrile, 1,3-butadiene and styrene was measured using methods No. 1604, No. 1024 and No. 1501 of the National Institute of Occupational Safety and Health (NIOSH), respectively. The US Environmental Protection Agency (USEPA) method was used to assess carcinogenic and health risks. The average occupational exposure to ABS was 560.82 µg m for 1,3-butadiene, 122.8 µg m for acrylonitrile and 1.92 µg m for styrene. The average lifetime cancer risk in the present study was 2.71 × 10 for 1,3-butadiene, 2.1 × 10 for acrylonitrile and 6.6 × 10 for styrene. Also, the mean non-cancer risk (hazard quotient) among all participants for each of 1,3-butadiene, acrylonitrile and styrene was 4.04 ± 6.93, 10.82 ± 14.76 and 0.19 ± 0.11, respectively. The values of carcinogenic and health risks in the majority of the subjects were within the unacceptable risk levels due to exposure to ABS vapors. Hence, corrective actions are required to protect the workers from non-cancer and cancer risks.
Topics: United States; Humans; Acrylonitrile; Styrene; Carcinogens; United States Environmental Protection Agency; Cross-Sectional Studies; Butadienes; Risk Assessment
PubMed: 35363589
DOI: 10.1080/10803548.2022.2059171 -
Dalton Transactions (Cambridge, England... May 2023Nitriles, particularly acrylonitrile and acetonitrile, are versatile chemicals that are used in various fields, such as polymer synthesis and pharmaceutical production.... (Review)
Review
Nitriles, particularly acrylonitrile and acetonitrile, are versatile chemicals that are used in various fields, such as polymer synthesis and pharmaceutical production. For a long time, acrylonitrile has been produced propylene ammoxidation with acetonitrile as a byproduct. The depletion of crude reservoirs and the production of unconventional hydrocarbon resources (, shale gas) renders light alkanes (including propane, ethane, and methane) to be potential feedstocks in the syntheses of acrylonitrile and acetonitrile. In this review, the processes of transforming light hydrocarbons to nitriles are surveyed, the developments in nitrile synthesis from alkanes are discussed, and the existing challenges and plausible solutions are addressed.
PubMed: 36883519
DOI: 10.1039/d2dt03795e -
The Journal of Chemical Physics Jul 2023The ion-molecule reaction is one of the most important pathways for the formation of new interstellar chemical species. Herein, infrared spectra of cationic binary...
The ion-molecule reaction is one of the most important pathways for the formation of new interstellar chemical species. Herein, infrared spectra of cationic binary clusters of acrylonitrile (AN) with methanethiol (CH3SH) and dimethyl sulfide (CH3SCH3) are measured and compared to those previous studies of AN and methanol (CH3OH) or dimethyl ether (CH3OCH3). The results suggest that the ion-molecular reactions of AN with CH3SH and CH3SCH3 only yield products with S…HN H-bonded or S∴N hemibond structures, rather than the cyclic products as observed in AN-CH3OH and AN-CH3OCH3 studied previously. The Michael addition-cyclization reaction between acrylonitrile and sulfur-containing molecules does not occur due to the weaker acidity of CH bonds in sulfur-containing molecules, which results from their weaker hyperconjugation effect compared to oxygen-containing molecules. The reduced propensity for the proton transfer from the CH bonds hinders the formation of the Michael addition-cyclization product that follows.
Topics: Acrylonitrile; Gases; Protons; Sulfur
PubMed: 37417750
DOI: 10.1063/5.0154135