P-tert-butylphenol Research Articles

Structures and performance of a polybenzoxazine with high heat resistance and high-frequency low-dielectric properties

Benzoxazine is a newly developed thermoset resin that has attracted significant academic and industrial interest due to its excellent properties. However, improving its dielectric performance while maintaining high heat resistant is crucial for expanding its application in 5G electronics. In this study, we designed and synthesized a novel benzoxazine monomer, DFDA-PTB, using p-tert-butylphenol (PTB) as the phenol source and furfuryl diamine (DFDA), derived from furfuryl amine, as the amine source. Two additional benzoxazines with similar structures were also synthesized for comparison. The cured product, poly(DFDA-PTB), was then analyzed to explore the relationship between its structure and properties. The results indicate that the introduction of a furan ring structure enhances thermal stability and reduces the dielectric constant. Additionally, the inclusion of tert-butyl groups further lowers the dielectric constant and dielectric loss. Simulation methods were employed to study the mechanisms behind these improvements. Poly(DFDA-PTB) demonstrated superior dielectric properties, with a dielectric constant of 2.51 and a dielectric loss of 0.0018 at 10 GHz. It also exhibited excellent heat resistance, with a char yield of 45.4 % at 800 °C. These properties make poly(DFDA-PTB) a promising candidate for electronic packaging and communication applications.

Influence of humic acid on the p-tert-Butylphenol removal efficiency by Spirodela polyrhiza-Tas13 association

Plant-microbe remediation technique is considered as a promising technology in removal of organic pollutants and its remediation efficiency is largely affected by a variety of surrounding environmental factors. Humic acid (HA) is the complex organic substance ubiquitous in environment, which characterized by its surfactant-like micelle microstructure and various reaction activity. In our study, a plant-microbe association with high p-tert-Butylphenol (PTBP) degradation potential constructed by Spirodela polyrhiza and Sphingobium phenoxybenzoativorans Tas13 has been used, and the influence of HA on the PTBP degradation efficiency of S. polyrhiza-Tas13 association was investigated. The result showed that the presence of HA greatly improved PTBP removal efficiency of S. polyrhiza-Tas13. The reason accounted for this may be due to the presence of HA promoted bacterial cell propagation, altered bacterial cell wall permeability, increased catechol 2,3-dioxygenase (C23O) enzyme activity of strain Tas13, rather than increasing the colonization ability of strain Tas13 on to the root surface. This study will greatly facilitate the application of aquatic plant-microbe association in environmental remediation.

Effect of humic acid on degradation of PTBP by strain Tas13

p-tert-Butylphenol (PTBP) is a kind of alkylphenol endocrine disruptor. PTBP is not only toxic to aquatic organisms and animals because of its high persistence in the environment, but also has acute toxicity, chronic toxicity, endocrine interference and certain toxicity of reproductive development. It is also harmful to human health and has become an important environmental pollutant. Therefore, the pollution of PTBP and its removal have attracted wide attention. Humic acid affects its adsorption and biodegradation efficiency in water environment. In this study, the adsorption analysis of PTBP by humic acid and the mechanism of the effect of humic acid on the degradation of PTBP by Tas13 were investigated. The results showed that humic acid could adsorb PTBP and promote the degradation of PTBP by Tas13.Raman spectroscopy suggests that humic acid may be associated with relaxation of membrane proteins and lipid monolayers to promote subsequent intracellular metabolism. Zeta potential analysis showed that humic acid interacts with bacterial surface functional groups to generate and regulate the transmembrane transport of carboxyl, amino and hydroxyl groups. The addition of humic acid promotes the transport of PTBP from the outside to the inside of bacterial cells, thus effectively degrading it. In addition, by measuring the C23O activity of strain Tas13, humic acid stimulated the active C23O gene, which enhanced the expression of C23O gene mediated by strain Tas13.

ALKYLATION OF PHENOL USING TERT-BUTANOL OVER MODIFIED CLAY CATALYSTS

Fe-bentonite is used as a catalyst for the alkylation of phenol using tert-butanol. Bentonite was modified by loading with the known concentrations of Fe/Zn/Zr. Series of catalysts such as Fe-bentonite, Zn-bentonite and Zr-bentonite were prepared by ion-exchange method and were used for the synthesis of p-tert-butylphenol (PTBP) by alkylation of phenol with tert-butylalcohol (TBA) in a batch process. Fe-bentonite was found to be an excellent catalyst with 100% TBA conversion and 81% selectivity for PTBP at 80°C. All the catalysts have been analyzed by different characterization methods, FTIR, XRD, TEM, SEM, and BET. The effect of various parameters like catalyst screening, reaction time, temperature, and the molar ratio of the reagents have been tested to obtain the best conversion and selectivity for the desired product.

Synthesis and study of new nonionic polyether water clarifier for oily wastewater

AbstractIn order to solve the problem of oily wastewater treatment in Shengli Oilfield, tert‐butyl phenol (TP) series nonionic polyether water clarifiers were synthesized by polymerization with p‐tert‐butyl phenol (PTBP) as the initiator. The water clarifiers were characterized by Fourier‐transform infrared spectroscopy (FT‐IR) and the interfacial tension test was carried out. The TP series of water clarifiers effect were evaluated by the oil content and suspension content in the clean water experiments. In addition, the effects of dosage and temperature on the water effect were discussed through the control variable method. The experimental results showed that the oil removal rate of TP6 can reach 95% and the suspension removal rate can reach 92% when the dosage of water clarifier was 40 mg/L, the cleaning water temperature was 55°C, and the cleaning water time was 30 min. The oily wastewater colour after cleaning was clear and transparent with the TP series of water clarifiers, and the effect was better than with commercial water clarifiers.

Removal pathway quantification and co-metabolic mechanism evaluation of alkylphenols from synthetic wastewater by phenolic root exudates in the rhizosphere of Phragmites australis

Phenolic root exudates (PREs) released from wetland plants are potentially effective for accelerating the biodegradation of alkylphenols, yet the inherent behavior is still unclear. In this study, two representative root exudates (REs), namely p-coumaric acid (PREs) and oxalic acid (non-PREs) were exogenously added as specific and non-specific co-metabolic substrates, respectively, to elucidate the quantification of each removal pathway and degradation mechanism of co-metabolism for alkylphenols (i.e. p-tert-butylphenol (PTBP)) from synthetic wastewater. The results showed that soil adsorption (31–37%), microbial degradation (27–37%), and plant uptake (16–41%) are the main removal pathways of PTBP by PREs in the Phragmites australis rhizosphere. Both REs enriched anaerobic functional community (anaerobic ammonium oxidation bacteria and denitrifying bacteria) and promoted the usage of PTBP as carbon source and/or electron donor. The activity of non-specific enzyme (polyphenol oxidase) was enhanced by RE which owning a significant positive correlation with bacterial abundance, whereas only PREs strengthened the activity of specific enzyme (monophenol oxidase) catalyzing the phenolic ring hydroxylation of PTBP followed by a dehydrogenation route. Moreover, exogenous PREs significantly improved the growth of degrading-related bacteria (Sphingomonas and Gemmatimonas), especially in unplanted soils with high activity of dioxygenase catalyzing the cleavage pathway of PTBP, instead of plant presence.

Rough sets and social ski-driver optimization for drug toxicity analysis

Background and objectives: Toxicity testing is an important step for developing new drugs, and animals are widely used in this step by exposing them to the toxicants. Zebrafishes are widely used for measuring and detecting the toxicity. However, measuring and testing toxicity manually is not feasible due to the large number of embryos. This work presents an automated model to investigate the toxicity of two toxicants (3, 4-Dichloroaniline (34DCA) and p-Tert-Butylphenol (PTBP)).Methods: The proposed model consists of two steps. In the first step, a set of features is extracted from microscopic images of zebrafish embryos using the Segmentation-Based Fractal Texture Analysis (SFTA) technique. Secondly, a novel rough set-based model using Social ski-driver (SSD) is used to find a global minimal subset of features that preserves important information of the original features. In the third step, the AdaBoost classifier is used to classify an unknown sample to alive or coagulant after exposing the embryo to a toxic compound.Results: For detecting the toxicity, the proposed model is compared with (i) three deterministic rough set reduction algorithms and (ii) the PSO-based algorithm. The classification performance rate of our model was ranged from 97.1% to 99.5% and it outperformed the other algorithms.Conclusions: The results of our experiments proved that the proposed drug toxicity model is efficient for rough set-based feature selection and it obtains a high classification performance.

Accelerated biodegradation of p-tert-butylphenol in the Phragmites australis rhizosphere by phenolic root exudates

Phenolic root exudates (PREs) released from plants are potentially effective for the degradation of aromatic compounds, yet the inherent process and mechanism remain insufficiently elucidated. In this study, we selected four representative PREs of P. australis, namely p-hydroxybenzoic acid (PHA), p-coumaric acid (PCA), caffeic acid (CA), and ferulic acid (FA), to investigate the accelerated biodegradation of p-tert-butylphenol (PTBP) by PREs in the rhizosphere and their mechanisms. The results showed that PTBP was initially adsorbed to root surface, and subsequently degraded by rhizosphere microbes of P. australis. The presence of PHA, PCA, and FA was beneficial for the enrichment of PTBP-degrading bacteria and the decomposition of PTBP, particularly PCA. Although CA was also favorable to microbial accumulation, it had no effect on PTBP degradation. This is possibly because PHA, PCA, and FA with monohydroxy structure similar like PTBP may promote the microbes for releasing hydroxylase to catalyze the phenolic ring hydroxylation followed by a cleavage pathway, whereas CA with ortho-dihydroxy structure cannot act on this reaction. Collectively, our data suggest PREs can accelerate biodegradation of specific aromatic compounds (e.g. PTBP) via co-metabolism in the rhizosphere of plants, according to their functional structures.

Direct Synthesis of Monodisperse Hollow Molecularly Imprinted Polymers Based on Unfunctionalized SiO2 for the Recognition of Bisphenol A

A novel and effective approach was developed to synthesize monodisperse hollow molecularly imprinted polymers (MHMIPs) with unfunctionalized SiO2 spheres in a mixture of toluene and CH3CN. The factors that affected the synthesis of MHMIPs were systematically investigated. It was determined that a suitable ratio of toluene to CH3CN and the use of a functional monomer that can generate double H-bonding interactions were the critical factors to obtain MHMIPs with high uniformity and monodispersion. The obtained MHMIPs exhibited a fast adsorption rate and high adsorption capacity (270 μmol/g) for bisphenol A. As the shell thickness increased from 90 nm to 130 nm, the binding capacity of the imprinted shells decreased gradually. The relative selectivity coefficients of MHMIPs for tetra-bromobisphenol A (TBBPA), phenol and p-tert-butylphenol (PTBP) were calculated as 1.53, 1.83 and 1.90, respectively. These findings indicate that MHMIPs have good adsorption performances and suggest applications in the selective removal or sensitive analysis of bisphenol A.

Magnetic iron oxide/graphene oxide nanocomposites: Formation and interaction mechanism for efficient removal of methylene blue and p-tert-butylphenol from aqueous solution

The formation and interaction mechanism of magnetic iron oxide/graphene oxide (MGO) nanocomposites for efficient removal of methylene blue (MB) and p-tert-butylphenol (PTBP) were investigated by characterization and batch experiments. The structural analysis of MGO showed that iron oxide (Fe3O4 and γ-Fe2O3) nanoparticles were anchored onto GO nanosheets by Fe-O-C bonds, and tended to distribute on the defects, plicated regions, and edges of GO nanosheets. Based on the adsorption experiments, GO nanosheets in MGO nanocomposites enhanced adsorption capacity for MB and PTBP via π-π interaction with recovered sp2-hybridized structure. And electrostatic interaction (attraction or repulsion) with oxygen-containing functional group possessed diverse effect for the adsorption of MB and PTBP. Meanwhile, iron oxide nanoparticles in MGO nanocomposites ensured an effective separation without occupying adsorption sites. Results of the regeneration indicated that MGO nanocomposites could retain high removal efficiency after five recycling. Furthermore, the relationship between structure and interaction mechanism were clarified. Our results demonstrate that MGO nanocomposites have a stable structure and favorable adsorption characteristics for MB and PTBP, and can be applied as a promising adsorbent to achieve the efficient removal of aromatic pollutants and separation from aqueous solution.

Erratum to: Electrodeposition of 4,4′-di-tert-butylbiphenyl peroxide from the anodic oxidation of p-tert-butylphenol in an alkaline acetonitrile solution

The electrogeneration of pure 4,4′-di-tert-butylbiphenyl peroxide as an electrodeposit could be achieved on a platinum electrode through the anodic oxidation of p-tert butylphenol in the presence of Lutidine, in addition to several soluble oligomers. The electrochemical and theoretical studies have shown that the favored coupling reaction corresponds to the O–O bond, albeit it is generally being considered unstable. Without the strong base, a mixture of trimer, tetramer and pentamer was deposited. The peroxide product presents a different electroactivity to that of the phenolic compound, with the appearance of a redox process involving cathodic and anodic symmetrical peaks at −0.10/0.15 V versus SCE, which indicates the preference of the polymer to adhere onto the electrode surface. The thermal degradation has also been analyzed. Quantum-chemical calculations reveal the reason for the oxygen–oxygen coupling.

Electrodeposition of 4,4′-di-tert-butylbiphenyl peroxide from the anodic oxidation of p-tert-butylphenol in an alkaline acetonitrile solution

The electrogeneration of pure 4,4′-di-tert-butylbiphenyl peroxide as an electrodeposit could be achieved on a platinum electrode through the anodic oxidation of p-tert butylphenol in the presence of Lutidine, in addition to several soluble oligomers. The electrochemical and theoretical studies have shown that the favored coupling reaction corresponds to the O–O bond, albeit it is generally being considered unstable. Without the strong base, a mixture of trimer, tetramer and pentamer was deposited. The peroxide product presents a different electroactivity to that of the phenolic compound, with the appearance of a redox process involving cathodic and anodic symmetrical peaks at −0.10/0.15 V versus SCE, which indicates the preference of the polymer to adhere onto the electrode surface. The thermal degradation has also been analyzed. Quantum-chemical calculations reveal the reason for the oxygen–oxygen coupling.

Zinc extraction from sulfate–chloride solutions with mixtures of a trialkyl amine and organic acids

In this work, for the first time, zinc extraction from sulfate–chloride solutions containing iron using mixtures of a С7–С9 fraction trialkyl amine (TAA) with a p-alkyl phenol (HP) and monocarboxylic acids (HAs) was studied. P-tertbutyl phenol was used as the alkyl phenol, while caprylic acid and the С11–С19 higher fractions of iso-acids (HIAs) were used as the monocarboxylic acids. The main process parameters that provided for high zinc recovery (~98.5–99%) and its separation from iron (βZn/Fe=15–25) were determined.Two extraction flowsheets for zinc recovery from sulfate–chloride solutions as zinc chloride followed by its conversion to zinc sulfate are proposed. The first one includes zinc extraction with the TAA and alkyl phenol mixture, washing of the extract from impurities and zinc stripping with water. The subsequent zinc concentration and its conversion to the sulfate solution are carried out by extraction with di(2-ethylhexyl)phosphoric acid (D2EHPA). The second flowsheet includes zinc extraction with the TAA and HIA mixture, washing of the extract with water to remove impurities, chloride ion stripping with an alkaline solution, and zinc stripping with a sulfuric acid solution, resulting in the extractant regeneration.The data obtained for synthetic solutions were confirmed for leach liquors of a sulfide concentrate from the Zimneye deposit (Russia). Zinc extraction was carried out from solutions containing (g/L) 10–12 Zn, 2–4 Cu, 12–15 Fe(III), 40–50 Fe(II), 0.7–0.8 Pb, 80–85 Cl, and 20–80 H2SO4. The composition of the zinc sulfate obtained by both technologies was of the best quality in accordance with the State Standard of Russia.

Contact Dermatitis From a Temporary Tattoo in a Boy With Contact Allergy to P-Tert Butyl Phenol Formaldehyde Resin

Contact Dermatitis From a Temporary Tattoo in a Boy With Contact Allergy to P-Tert Butyl Phenol Formaldehyde Resin

Synthesis and characterization of polycarbonates containing terminal and chain interior siloxane

Silicone polycarbonates having polydimethyl siloxane (PDMS) and heptamethyl trisiloxane (HMTS) were synthesized by the interfacial polymerization. Instead of common chain terminator p-tert-butyl phenol (PTBP), eugenol capped HMTS, and PDMS were used. PDMS was also attached into the chain interior of the polymer in different molar ratios. PDMS and HMTS were capped with eugenol through the hydrosilylation reaction using Karstedt’s catalyst. Both monohydroxy and dihydroxy terminated eugenosiloxanes were synthesized in order to use as chain terminator and interior subunit of polymer, respectively. Structural characterization and the study of the properties, such as thermal behavior, thermooxidative stability, surface morphology, wettability of the synthesized polymers were investigated. Flexibility and wettability of the synthesized polymers increases with increasing of silicone content. Polymers showed satisfactory thermo oxidative stability and transparency as good as bisphenol-A-polycarbonate.

ジクロロメタンを用いないポリカーボネート中のビスフェノールＡ分析法の検討

An improved method for determination of bisphenol A (BPA), phenol (PH), p-tert-butylphenol (PTBP) and diphenylcarbonate (DPC) in polycarbonate products was developed without using the hazardous solvent dichloromethane. Polycarbonate samples were ground to powder or cut into small pieces, and 0.5 g was soaked in 5 mL of acetonitrile for 24 hours at 40 degrees C. The test solution was then filtered and subjected to HPLC analysis. The proposed method was evaluated by comparison of the results with those of the standard method for 14 polycarbonate products. Extraction ratios (average values obtained by the present method/average values obtained by the standard method) of BPA, PH, PTBP and DPC were 0.89-1.19, 0.89-1.14, 0.94-1.30 and 1.08-1.11, respectively. While 120 mL/sample of organic solvent is required in the standard method, only 5 mL/sample of acetonitrile was used in our new method.

Stereoselective hydrogenation of p- tert-butylphenol over supported rhodium catalyst

p- tert-Butylcyclohexanol is used as an intermediate for manufacturing esters with lower carboxylic acids, which are important in perfumery, soap and detergents manufacturing. Stereoselective hydrogenation of p- tert-butylphenol (PTBP) to cis and trans- p- tert-butylcyclohexanol (PTBCH) has been carried out by using supported metal catalysts such as rhodium supported on carbon (2% Rh/C), Raney nickel, nickel supported on silica (20% Ni/SiO 2), and palladium supported on carbon (5% Pd/C). Among the variety of catalysts used 2% Rh/C exhibited 100% conversion of PTBP and 100% selectivity of the cis-isomer of PTBCH when methanesulphonic acid was used as the co-catalyst. The reaction was 100% selective towards the product. The effects of various parameters on the rates of reaction were studied systematically and a kinetic model was built. The reaction was found to be kinetically controlled. The formation of cis-isomer was explained theoretically.

Simultaneous p-tert-butylphenol-formaldehyde resin and p-tert-butylcatechol contact allergies in man and sensitizing capacities of p-tert-butylphenol and p-tert-butylcatechol in guinea pigs.

In patients who are hypersensitive to p-tert-butylphenol-formaldehyde resin (PTBP-F-R), it is necessary, for diagnostic, therapeutic, and preventive reasons, to know the identity of the primary sensitizing substances, their sensitizing capacities, and their crossreaction patterns. The aims of this study were to investigate the presence of a simultaneous p-tert-butylcatechol (PTBC) contact allergy in individuals who were hypersensitive to PTBP-F-R, to investigate the sensitizing capacity of PTBC and p-tert-butylphenol (PTBP) in guinea pigs, and to study any crossreaction patterns. In 294 dermatitis patients tested with PTBP-F-R and PTBC, there was a statistically significant over-representation of simultaneous test reactions. Use of the guinea pig maximization test demonstrated that PTBC is a strong sensitizer giving crossreactions to PTBP. PTBP, however, failed to induce sensitization.

Branching by Reactive End Groups. Synthesis and Thermal Branching of 4-Hydroxybenzocyclobutene/p-tert-Butylphenol Coterminated Bisphenol A Polycarbonates

Long chain branched bisphenol A polycarbonates (BA PC's) were prepared by use of a combination of thermally reactive 4-hydroxybenzocyclobutene (BCB-OH) and the nonreactive p-tert-butylphenol (PTBP) chain terminators. These two monophenols react under interfacial conditions at similar rates to provide a statistical distribution of coterminated PC's having molecular weights controlled by the total amount of coterminators. Heating these materials to 300 °C causes branching and/or cross-linking depending on the value of XBCB, thereby separating the polycondensation and branching processes and allowing greater degrees of branching than possible by random branching during polycondensation. At XBCB < 0.55 the BCB-OH/PTBP BA PC's branch without cross-linking. The poly-BCB products formed upon the thermal branching of these PC's are the same as those observed in cross-linked BCB terminated BA PC's. The nongel value of XBCB is that expected for a thermally reacted BCB functionality of 2.6, which is the same as that estimated for cross-linked BCB PC's. Based on the statistical distribution of the chain ends and the functionality of the poly-BCB products, BCB-OH/PTBP BA PC's having XBCB values of 0.50 have a minimum of 0.45 number fraction branched chains. The Mw and polydispersity of branched BCB-OH/PTBP BA PC's depend on their initial molecular weight and increase with XBCB. The Mw's for each composition converge to large values (∼100 000 Da) near the gel point, after which the Mw's of the soluble fractions decrease. The Tg's of these polymers scale inversely with Mn rather than Mw. Film toughness also trends with Mn. Films of branched BCB-OH/PTBP BA PC's having Mn > ∼2Me are relatively tough and flexible, while those having lower Mn's, regardless of Mw, are relatively brittle. The melt viscosities of branched BCB-OH/PTBP PC's are very high at low shear rates, as expected from their high Mw's, but decrease dramatically with increasing shear rates to values approaching those of conventional linear and randomly branched PC's. Such high zero-shear viscosity, which is indicative of high melt strength, and large shear sensitivity suggests that these new materials could display significant improvements in melt processing by techniques such as blow molding, thermoforming, injection molding, and extrusion.

ｐ‐ｔｅｒｔ‐Ｂｕｔｙｌｐｈｅｎｏｌ（ＰＴＢＰ）使用職場におけるＰＴＢＰ曝露評価

Two cases of occupational vitiligo were observed in a resin factory where p-tert-butylphenol (PTBP) has been used as a starting material or an intermediate of synthetic resin. In this resin factory (A shop) and another resin factory (B shop), occupational exposure to PTBP was assessed in workers charging this chemical into the reaction vessel by means of a gas-chromatographic measurement of the environmental PTBP concentration and their urinary PTBP excretion. Assessment in A shop was made after the working condition was partly improved. Geometrical mean values of 8 h-time-weighted-average (8 h-TWA) of PTBP in air near the charger's breathing zone (personal air) were 0.215 mg/m3 in A shop and 2.12 mg/m3 in B shop. Continuous measurements of PTBP concentration in some stationary air of the shops showed that the maximum environmental PTBP values occurred during charging. Urinary PTBP concentration was increased to the maximum values 2 to 4 h after charging of this chemical and then rapidly decreased. Biological half-lives of urinary PTBP were estimated as 4.4 h in A shop and 4.8 h in B shop. The urinary PTBP concentration was correlated to 8 h-TWA of PTBP in the personal air. In particular, PTBP in urine collected at the end of the shift showed an excellent correlation to PTBP in the personal air (r = 0.84, n = 9, A shop; r = 0.88, n = 11, B shop). These results indicate that biological monitoring using urinary PTBP concentration is a suitable means of assessing exposure to this alkylphenol and the urine collected at the end of shift is the best sample for monitoring. In addition, the present environmental and urinary PTBP values were compared with those described in the literature and the relation of the occupational vitiligo with PTBP exposure is discussed.