1-amino-2-propanol Research Articles

Isopropanolamine‐modified ammonium polyphosphate for improved flame retardancy of epoxy resin

AbstractIn this work, the flame retardant ISA‐APP, obtained by modification of ammonium polyphosphate (APP) with isopropanolamine (ISA), was employed in epoxy resins (EP) in an attempt to enhance the fire resistance of EP. The findings indicate that, with an incorporation of 20 wt% ISA‐APP in the EP, the limiting oxygen index (LOI) of EP/ISA‐APP attains 33.5%, accompanied by a UL‐94 test V‐0 rating. This performance surpasses the flame retardancy observed in EP/APP composites at equivalent content. The outcomes derived from the cone calorimeter test (CCT) demonstrate that EP/ISA‐APP significantly suppresses the release of heat, generation of smoke, and emission of noxious gas during EP/ISA‐APP combustion. The peak‐heat release rate (pHRR) and total heat release (THR) of EP/ISA‐APP are decreased by 74.4% and 63.6%, respectively, compared to pure EP. Further analysis of the char residues of EP/ISA‐APP shows that the POC structure generated during combustion effectively contributes to a high‐quality char layer formation. This investigation presents a viable approach for enhancing flame retardant and economic benefits of APP and advancing the development of highly effective flame retardants.

Study on the molecular interactions of binary mixtures of allyl alcohol and amino-alcohol solvents through thermodynamic properties and FT-IR spectra and correlation with the Jouyban–Acree model

ABSTRACT Densities (ρ), speeds of sound (u), and viscosities (η) for three binary mixtures of allyl alcohol with 3-amino-propan-1-ol, 2-amino-2-methyl-propan-1-ol (aminomethyl propanol), and 1-amino propan-2-ol (isopropanol amine) were calculated at temperatures ranging from 303.15 to 313.15K and at atmospheric pressure over the entire composition range. Experimental measurements were used to calculate the excess molar volume, excess isentropic compressibility, deviation in viscosity, and excess Gibbs free energy of the activation of viscous flow. Partial molar properties and partialmolar properties at infinite dilution are also calculated. The Prigogine–Flory–Patterson (PFP) theory is applied to identify the predominant molecular interaction. The results of the Jouyban–Acree model are discussed in terms of the mean relative deviation (MRDs) and individual relative deviation (IRD) between the calculated and experimental parameters as an accuracy criterion. FTIR studies have also been added to confirm the experimental findings of the investigated mixtures.

1,3,4-Oxadiazole Derivatives as Plant Activators for Controlling Plant Viral Diseases: Preparation and Assessment of the Effect of Auxiliaries.

Plant viral diseases cause the loss of millions of dollars to agriculture around the world annually. Therefore, the development of highly efficient, ultra-low-dosage agrochemicals is desirable for protecting the health of crops and ensuring food security. Herein, a series of 1,3,4-oxadiazole derivatives bearing an isopropanol amine moiety was prepared, and the inhibitory activity against tobacco mosaic virus (TMV) was assessed. Notably, compound A14 exhibited excellent anti-TMV protective activity with an EC50 value of 137.7 mg L-1, which was superior to that of ribavirin (590.0 mg L-1) and ningnanmycin (248.2 mg L-1). Moreover, the anti-TMV activity of some compounds could be further enhanced (by up to 5-30%) through supplementation with 0.1% auxiliaries. Biochemical assays suggested that compound A14 could suppress the biosynthesis of TMV and induce the plant's defense response. Given these merits, designed compounds had outstanding bioactivities and unusual action mechanisms and were promising candidates for controlling plant viral diseases.

Synthesis of tetrapod CdS by one-pot Solvothermal Method for Photodegradation to rhodamine B

In this paper, tetrapod CdS for photodegradation to rhodamine B (RhB) was reported for the first time. Tetrapod CdS was synthesized by one-pot solvothermal method. The category of sulfur source and mixed solvent, the volume ratio of mixed solvent, reaction temperature and time were observed. The synthesized samples were characterized by SEM, XRD, XPS, TEM, absorption spectrum and C–V measurement. The results showed that, tetrapod CdS with wurtzite structure was synthesized successfully with thioacetamide as sulfur source, ethanediamine (EA) and isopropanolamine (IPA) as mixed solvent. Tetrapod CdS was applied in the photodegradation to RhB, it displayed pseudo-first-order kinetics and obtained the maximum photodegradation efficiency up to 99.5%, which may be originated from low electron-hole recombination. Moreover, the photodegradation efficiency and constant rate showed the dependence on the morphologies of tetrapod CdS. Finally, the photodegradation products were characterized by LC-MS to obtain the photodegradation mechanism.

Facile Preparation of Self-Reducible Cu Nanoparticle Paste for Low Temperature Cu-Cu Bonding

Cu nanoparticle (NP) paste is considered the next-generation die-attach material because of its cost-effectiveness and high conductivity and electro-migration resistance. However, the spontaneous oxidation of Cu NPs severely restrains the incorporation of Cu NP paste into practical applications. Herein, a novel self-reducible Cu NP paste was prepared and demonstrated for low-temperature Cu-Cu bonding. The Cu NP paste was composed of 62 wt.% ultra-small Cu NPs (6.5 nm) and 38 wt.% organic components [isopropanolamine (IPA) stabilizer and ethylene glycol]. The reducing and sintering mechanisms of Cu NP paste were proposed, and the effects of sintering temperature on the mechanical properties and microstructure evolutions of Cu-Cu joints were systematically investigated. Consequently, the reducibility of the IPA stabilizer was beneficial for eliminating the surface oxides and enhancing the sinterability of Cu NPs, and the robust and high-strength Cu-Cu joints (> 20 MPa) were achieved at low temperature of 200°C in Ar atmosphere. Furthermore, the microstructure observations reveal that the robust bonding is attributed to the remarkable metallurgical interconnection between the substrates and sintered Cu NP layer.

Novel insights into the adsorption mechanism of the isopropanol amine collector on magnesite ore: A combined experimental and theoretical computational study

This paper focuses on the adsorption behavior and mechanism of the isopropanol amine collector as a novel collector on magnesite ore to expand the application of hydroxyl amine collectors and improve the efficiency of low-grade magnesite ore resource usage. Novel insights into the adsorption mechanism of the isopropanol amine collector on magnesite ore were proposed through a combined experimental and theoretical computational study. Flotation tests showed that the collector exhibited different flotation behaviors to three minerals (quartz > dolomite > magnesite). Adsorption was achieved due to the electrostatic and hydrogen bond affinities by Fourier Transform infrared spectroscopy (FTIR), and zeta potential measurements, and the exposed O on the surface was involved in the adsorption interaction. Molecular dynamics simulations confirmed the same rules of the flotation behaviors and illustrated that a compact inner layer of N-dodecyl-isopropanolamine (DIPA) formed on the quartz surface. The hydrogen bonds played a significant role in the different flotation behaviors of DIPA to quartz (OS··HOR and OS··HNR), magnesite (only little OS··HOR), and dolomite (OS··HOR). Additionally, the results indicated that the flotation behaviors of DIPA were closely related to the O sites density and charge of the surfaces of three minerals. Furthermore, the results reveal some straightforward mechanisms of introducing isopropanol groups at the molecular scale, which is vital for screening the functional groups and guiding the design of the novel collectors for minerals.

NOVEL PALM OIL BASED POLYOLS WITH AMINE FUNCTIONALITY SYNTHESIS VIA RING OPENING REACTION OF EPOXIDIZED PALM OIL

In polymer chemistry, polyol usually used as starting materials for polyurethane (PU) production in which upon reacted with isocyanate will affect the physical and chemical properties of the obtained PU. Polyols that are mostly derived from petrochemical resources are facing issues such as depletion of petroleum sources as well as the increasing in market price. Ring opening reaction (ROR) of epoxidized palm oil (EPO) had been carried out using isopropanolamine (IPA) to impart polyol with amine functionality. The effect of reaction time on the opening of oxirane ring was investigated. FTIR spectra showed that the oxirane ring opening of EPO can occur at 6 hours reaction time, corresponding to the deacreasing intensity of oxirane COO twin band at 824-830 cm-1. The OH value of the amine- functionalized-polyol was calculated at around 240-253 mg KOH/g. By prolonging the reaction time the OH value has slightly reduced. Mass spectroscopy analysis revealed that the polyol has a molecular weight in the range of oligo-polyols (400 – 500 Da).

Experimental Evaluation of a Surfactant/Compound Organic Alkalis Flooding System for Enhanced Oil Recovery

Monoisopropanolamine (MIA) and monoethanolamine (MEA), which are two kinds of organic alkalis, present favorable potential for enhanced oil recovery. When MIA and MEA are respectively applied, the minimum oil/water interfacial tension (IFT) can be reduced to about 1 mN/m, the crude oil can be emulsified, and the originally oil–wet sand surface can be altered to weak water-wet status. To display the synergistic effect of surfactant and organic alkalis, a surfactant/compound organic alkalis (MIE/MEA) flooding system (SMM), which consists of 0.10 wt % SDBS, 0.15 wt % MIA, and 0.10 wt % MEA, is screened. This system can reduce the minimum oil/water IFT to an ultralow value which contributes to the emulsion stability. Results of sandpack flooding tests indicate that although the incremental oil recovery can be continuously enhanced with the increase of the SMM slug size, there is an optimal injection size (0.8 PV in this study) when the expense is taken into consideration. As for the effect of the injection ty...

Imidazolyl-substituted silatranes derived from triethanolamine and tris(isopropanol)amine: syntheses and structural characterization

The syntheses of seven new silatranes, N-[3-(3,7,10-trimethylsilatranyl)propyl]imidazole (7), N-(3-silatranylpropyl)-4-methylimidazole (8), N-[3-(3,7,10-trimethylsilatranyl)propyl]-4-methylimidazole (9), N-(3-silatranylpropyl)-2-methylimidazole (10), N-[3-(3,7,10-trimethylsilatranyl)propyl]-2-methylimidazole (11), N-(3-silatranylpropyl)-2-imidazoline (12), and N-[3-(3,7,10-trimethylsilatranyl)propyl]-2-imidazoline (13), are reported. These silatranes were prepared by transesterification of triethoxysilanes, N-(3-triethoxysilylpropyl)imidazole (3), N-(3-triethoxysilylpropyl)-4-methylimidazole (4), N-(3-triethoxysilylpropyl)-2-methylimidazole (5) and N-(3-triethoxysilylpropyl)-2-imidazoline (6) with triethanolamine (1), and tris(isopropanol)amine (2). The structures of five silatranes (7, 8, 9, 10, and 12) were confirmed by X-ray crystallography. The compounds were investigated by elemental analysis, IR, 1H, 13C NMR spectroscopy, thermogravimetric analysis, and mass spectrometry.

Densities, Refractive Indices, Viscosities, and Spectroscopic Study of 1-Amino-2-propanol + 1-Butanol and + 2-Butanol Solutions at (288.15 to 333.15) K

Densities, refractive indices, and viscosities of 1-amino-2-propanol (monoisopropanolamine (MIPA)) + 1-butanol and 1-amino-2-propanol + 2-butanol solutions are reported over the entire range of mole fractions and the temperature range from (288.15 to 333.15) K. The Redlich–Kister relation was used for correlation of measured results of excess molar volumes, viscosities, and refractive indices as a function of temperature and composition. Partial molar volumes at infinite dilution were determined from apparent molar volumes. Negative values for excess molar volumes, refractive indices, and viscosity deviations are observed over the entire composition range. The viscosities of 1-amino-2-propanol with 1-butanol and 1-amino-2-propanol with 2-butanol are well represented by an Arrhenius equation. Activation energies for viscous flows are determined by linearization of the Arrhenius equation, providing a clear explanation of the influence on hydrogen bonding. In order to confirm molecular interactions between compounds obtained by analysis of infinite dilution of solute, a FT-IR spectroscopy study was performed at T = 298.15 K. Interactional and structural effects were investigated through calculations of excess Gibbs free energy of activation of viscous flow.

CO2 Mass Transfer and Solubility in Aqueous Primary and Secondary Amine

Abstract Three amines were tested as solvents for CO 2 capture: monoisopropanolamine (MIPA) and 3 amino 1 propanol (MPA), which are primary amines, and diethanolamine (DEA), which is a secondary amine. The three amines were tested at 7 molal in water, which corresponds to 30 wt % monoethanolamine (MEA). The CO 2 absorption rate and solubility in the solvents was measured using a bench scale wetted wall column (WWC) at 20–100 °C and over the range of CO 2 loading expected for coal flue gas. The experimental data are analyzed to suggest performance in a real process. The performance of the three new amines are compared against literature results for 7 m MEA and other solvents with amines of related structures, such as 10 m Diglycolamine (DGA) ® and 4.8 m 2-amino-2-methyl-1-propanol (AMP). The mass transfer performance and the CO 2 carrying ability of the amine are related to the structural hindrance and the pKa. The CO 2 absorption rate of 7 m MIPA and 7 m DEA are competitive with 7 m MEA. For 7 m MPA, the measured liquid film mass transfer coefficient is about 20% lower than 7 m MEA. The CO 2 solubility data are used to generate a semi-empirical model for each of the new solvents. The results for CO 2 solubility at 40 °C suggest that MIPA and MPA have similar CO 2 capacity to MEA, whereas DEA has double the CO 2 capacity of the three primary amines. Based on the comparison of data collected in this work and literature results, it is generalized for unhindered amines that the overall CO 2 mass transfer performance of the solvent is inversely related to the pKa of the amine. Also, the CO 2 capacity of the amine increases with the relative hindrance of the nitrogen group in the amine molecule.

Review of technological methods and experimental determination of thermodynamic and transport properties of reagents for carbon dioxide removal from flue gases

In this work a review of the currently available methods for carbon dioxide removal from flue gasses is given. Some of them are commercially available, while others are still under development. Special attention is given to detailed description of the methods based on hemi sorption by aqueous solutions of alkanol amines, which found wide commercial use in industry. Selection of appropriate absorbent, process equipment, methods, working parameters, combustion process etc. are some of key points that will be reviewed within this work in order to present advantages and limitations of carbon dioxide removal methods. In the experimental section density, viscosity and refractive index of insufficiently investigated carbon dioxide removal agents, such as monoisopropanolamine (MIPA), diisopropanolamine (DIPA), triisopropanolamine (TIPA) and currently widely used dietanolamine (DEA) are provided. The data obtained are crucial for the equipment design and process optimization.

CO2 Adsorption by Y-Type Zeolite Impregnated with Amines in Indoor Air

The capture and concentration of CO2 by cyclic adsorption–desorption processes in indoor air environments are studied. A synthesized Y-type zeolite was impregnated with amines used to capture CO2 to maintain good indoor air quality (IAQ). Three kinds of amines, including monoethanol amine (MEA), isopropanol amine (IPA), and tetraethylenepent amine (TEPA), were selected to study the performance of CO2 adsorption capacity at a fixed-bed in an 80-L air chamber. These Y8 loaded with amines were examined with a Scanning Electron Microscope (SEM), X-ray Diffraction (XRD), Infrared Spectroscope (IR) and Thermogravimetric Analyzer (TGA) to determine their textural properties before and after amines-impregnation. The CO2 adsorption capacities of modified Y8 was substantially higher than that of the original Y8 adsorbent, and the highest capacity was up to 158 mg/g-adsorbent-hr. This study shows that the order of adsorption capacity for the three types of amines was TEPA > MEA > IPA. The first-order kinetic model was best fitted to adsorb CO2. The rate constant (k) of the first-order adsorption model can be further used for the design and application of a CO2 control system in IAQ. The results of this study show that amines functionalized Y8 have excellent adsorption potential for removing indoor CO2.

Densities, Viscosities, and Refractive Indices of Aqueous Alkanolamine Solutions as Potential Carbon Dioxide Removal Reagents

To determine the possibility of improvement of the process of CO2 removal by absorption with alkanolamines, densities, viscosities, and refractive indices of four aqueous alkanolamine solutions (water + monoisopropanolamine (MIPA), diisopropanolamine (DIPA), triisopropanolamine (TIPA), or diethanolamine (DEA)) were measured in the temperature range (298.15 to 343.15) K and at atmospheric pressure. Due to the corrosive effect of increased concentration of alkanolamine solutions, the mass fractions of alkanolamines were selected as w = 0.05, 0.1, 0.15, 0.20, and 0.25. The measured data were regressed with polynomial equations. Obtained results provide necessary data for industrial equipment design and process optimization regarding greenhouse gases (GHG), but also it is a foundation for further investigation of the potential replacement of usually used monoethanolamine with other mixtures of alkanolamine solutions presented within this work.

Effect of the Intermolecular Hydrogen Bond between Carbazole and N,N-Dimethylformamide/Isopropanolamine on the Solubility of Carbazole

The influence of hydrogen bonding on the solubility of carbazole and anthracene in N,N-dimethylformamide (DMF) and isopropanolamine (IPA) is investigated accordingly by 1H nuclear magnetic resonance (NMR) analysis. The chemical shift for the free and hydrogen-bonding proton of the anthracene and carbazole solution in DMF, IPA, and the mixture of the two was collected by a 600 MHz 1H NMR spectrometer. It is proposed that DMF, IPA, and a mixture of the two would be able to efficiently refine carbazole from crude anthracene oil. This phenomenon is shown to be the result of the intermolecular hydrogen bond of N–H···O and N–H···N formed between carbazole and the DMF/IPA mixture solvent, which greatly enhanced the solubility of carbazole in DMF and IPA. The arising steric hindrance effects derived from the intermolecular hydrogen bonding between DMF and IPA result in the significant solubility decline of anthracene and carbazole in the DMF and IPA mixture.

Volumetric Properties, Viscosities, and Refractive Indices for Aqueous 1-Amino-2-Propanol (Monoisopropanolamine (MIPA)) Solutions from (298.15 to 343.15) K

Densities and viscosities at six temperatures in the range (298.15 to 343.15) K and refractive indices at nine temperatures in the range (293.15 to 333.15) K are reported for aqueous solutions of 1-amino-2-propanol (monoisopropanolamine (MIPA) or 1-AP). Excess molar volumes, viscosity deviations, and refractive index deviations were calculated from the measurement results and correlated as a function of composition using the Redlich-Kister relation and polynomial equations. Partial molar volumes at infinite dilution were determined from the apparent molar volumes. Negative values for excess molar volumes and molar refraction changes are observed over the whole composition range, whereas viscosity data exhibit both negative and positive deviations. Cross-associated hydrogen bonds forming between 1-AP and water contribute to the deviations in the properties with respect to mole fractions and temperatures.

Investigating the Properties of Aqueous Monoisopropanolamine Using Density Data from 283.15K to 353.15K

The published isothermal density data of aqueous monoisopropanolamine (MIPA) for different temperatures are converted into molar volumes as a function of composition. Tikhonov regularization is applied to obtain the derivatives of molar volume with respect to composition. These derivatives are used to compute the two partial molar volumes of the aqueous solution covering the entire composition range and for all the temperatures reported. A second application of Tikhonov regularization is then used to obtain the partial molar coefficients of the thermal expansion of the solution under constant pressure. This is followed by an examination of the second derivative of the partial molar volumes with respect to temperature over the entire composition range. The signs of these derivatives, for different compositions and temperatures, allow the change in the molecular interaction between MIPA and water in aqueous solution to be discussed.

Amine loaded zeolites for carbon dioxide capture: Amine loading and adsorption studies

Novel functionalised adsorbents have been synthesized by immobilization of various amines on synthetic zeolite 13X. Various primary and secondary amines namely monoethanolamine (MEA), ethylenediamine (ED) and isopropanol amine (IPA) have been immobilized on zeolite 13X. Quantitative estimations of the amine loadings were undertaken using different analytical techniques namely titrimetric, total organic carbon and gas chromatography analysis. Fairly good correlation was obtained for amine loadings estimated using the three techniques. Effect of various parameters like effect of solvent, shaking time, synthesis temperature, and wetting of pellets prior to amine loadings was also studied. The results revealed that maximum loading was achieved for methanol-mediated synthesis conducted using previously wetted pellets at room temperature and with 15 min of shaking time. Preliminary attempts have also been made to determine the CO 2 adsorption capacities of these newly developed materials. The adsorption capacities obtained were 16.01 mg/g for unmodified zeolite 13X and 19.98, and 22.78 mg/g for zeolite modified with monoethanol amine, and isopropanol amine.

Pharmacokinetics and bioavailability of diisopropanolamine (DIPA) in rats following intravenous or dermal application

This study was conducted to determine the relative dermal bioavailability (absorption), distribution, metabolism, and excretion (ADME) of diisopropanolamine (DIPA), an alcohol amine used in a number of industrial and personal care products. Groups of 4 female Fischer 344 rats received either a single bolus i.v. dose of 19.0 mg/kg 14C-DIPA in water or a dermal application of 19.5 mg/kg 14C-DIPA in acetone to an area of 1 cm 2 on the back and covered with a bandage. Time-course blood and excreta were collected and radioactivity determined. Urine was analyzed for DIPA and monoisopropanolamine (MIPA). Following i.v. administration, DIPA was rapidly cleared from the plasma and excreted into urine in a biexponential manner ( t 1/2 α , 0.4 h; t 1/2 β , 2.9 h). The levels of radioactivity in plasma dropped below the limit of detection 12 h post-dosing. A total of 97 ± 4% of the dose was actively excreted in urine by kidney, most (∼71%) within 6 h of dosing, virtually all as parent compound; renal clearance exceeded the glomerular filtration rate. Following dermal application, ∼20% of the dose was absorbed in 48 h with the steady-state penetration rate of ∼0.2%/h. Most (14.4%) of the applied radioactivity was excreted in urine at a relatively constant rate due to the presence of large amount of the 14C-DIPA at the application site. Fecal elimination was <0.2% of the dose. The absorbed DIPA did not accumulate in tissues; only ∼0.1% of the administered dose was found in liver and kidney. The absolute systemic dermal bioavailability (dose corrected AUC dermal/AUC i.v.) of 14C-DIPA was 12%. The ADME of DIPA contrasts that of its diethanol analogue, diethanolamine, which displays a broad spectrum of toxicity in rats and mice. Toxicologically significant concentrations of DIPA are unlikely to be achieved in the systemic circulation and/or tissues as a result of repeated dermal application of products containing DIPA due to slow absorption from the skin, rapid unchanged elimination in urine, and majority of the products contain ⩽1% DIPA.

Persistence and Biodegradation of Monoethanolamine and 2-Propanolamine at an Abandoned Industrial Site

Soil and groundwater samples were collected at the site of a former chemical processing plant in areas impacted by accidental releases of MEA (monoethanolamine) and IPA (2-propanolamine or isopropanolamine). Although their use had ceased ca. 10 years before sample collection, soils collected at contamination sites had MEA concentrations ranging from ca. 400 to 3000 mg/kg and IPA concentrations from ca. 30 to 120 mg/kg. Even though alkanolamines are miscible in water, transport to groundwater was slow, apparently because they are present in soil as bound cations. Only one groundwater sample (near the most highly contaminated soil)from wells directly adjacentto and down-gradient from the contaminated soils had detectable MEA, and none had detectable IPA. However, ammonia was found in the soil samples collected in the MEA-contaminated areas (ca. 500-1400 mg/kg) and the groundwater (80-120 mg/L), as would be consistent with bacterial degradation of MEA to ammonia, followed by transport of ammonia into the groundwater. Counts for bacteria capable of using MEA or IPA as a sole carbon source were ca. 5 x 106 and 1 x 106 (respectively) per gram in uncontaminated site soil, but no such organisms were found in highly contaminated soils. Similarly, bacterial degradation of MEA in slurries of highly contaminated soils was slow, with ca. 8-20 days required for half of the initial concentrations of MEA to be degraded at 20 degrees C and 30-60 days at 10 degrees C. In contrast, bacterial degradation studies using uncontaminated site soils spiked with ca. 1300 mg/L either MEA or IPA showed very rapid degradation of both compounds,with more than 99% degradation occurring in less than 3 days with quantitative conversion to ammonia, followed by slower conversion to nitrite and nitrate. The results obtained in the site soils, the groundwater samples, and from the biodegradation studies demonstrate that MEA and IPA can persist for decades on soil at high (hundreds of mg/kg) concentrations without significant migration into groundwater, despite the fact that they are miscible in water. Since MEA and IPA exist primarily as cations at the pH of site soils, their persistence apparently results from strong binding to soil, as well as inhibition of natural bioremediation in highly contaminated field soils.