Lauroyl Chloride Research Articles

Esterification of Rice Straw Cellulose Using Microwave Heating for Plastic Film Preparation

Esterified rice straw cellulose was synthesized by the reaction of cellulose with lauroyl chloride in the presence of toluene medium. Microwave heating was used to accelerate the esterification of cellulose. The optimum condition for esterification was investigated in term of microwave power and reaction time. Solubility of modified cellulose was characterized. The cellulose films were prepared by solvent casting method and mechanical properties of cellulose films were tested. The result shows that the best condition for cellulose esterification was 100 W of microwave power and 15 minute of esterification time. Percentage of weight increase of esterified cellulose at this condition was 143.83 %. Modified cellulose can be dissolved in organic solvent such as toluene, dichloromethane and chloroform. Tensile properties of cellulose films were examined. Tensile strength, Young’s modulus and % elongation at break of rice straw cellulose ester film were 2.33 MPa, 56.63 MPa and 4.21 %, respectively.

Development of a biocompatible creatinine-based niosomal delivery system for enhanced oral bioavailability of clarithromycin

Context: Nonionic surfactant vesicles have gained increasing scientific attention for hydrophobic drugs delivery due to their biocompatibility, stability and low cost.Objective: The aim of the present study was to synthesize and evaluate a novel creatinine-based nonionic surfactant in terms of its ability to generate biocompatible niosomal system for the delivery of Clarithromycin.Materials and Methods: The surfactant was synthesized by reacting creatinine with lauroyl chloride followed by characterization using 1HNMR and MS. The drug-loaded niosomal vesicles of the surfactant were characterized for drug encapsulation efficiency (EE) using LC-MS, vesicle size using dynamic light scattering (DLS) and vesicle shape using atomic force microscopy (AFM). The surfactant was also investigated for blood hemolysis, in vitro cytotoxicity against different cell lines and in vivo acute toxicity in mice. Furthermore, the in vivo bioavailability of Clarithromycin encapsulated in the novel niosomal formulation was investigated using rabbits and quantified through validated LC-MS/MS method.Results and discussion: Findings showed that vesicles were able to entrap up to 67.82 ± 1.27% of the drug, and were rounded in shape with a size around 202.73 ± 5.30 nm and low polydispersity. The surfactant caused negligible blood hemolysis, very low cytotoxicity and was found to be safe up to 2500 mg/kg body weight using mice. The niosomal formulation showed twofold enhanced oral bioavailability of Clarithromycin as compared to commercial formulations of the drug.Conclusion: The study has shown that the creatinine-based niosomes developed in our laboratory were biocompatible, safe and increased the oral bioavailability of the model hydrophobic Clarithromycin using experimental animals.

Poultry Chicken Feather Derived Biodegradable Multifunctional Additives for Lubricating Formulations

The present paper describes the first successful application of poultry waste chicken feathers in the development of green, biodegradable, and eco-friendly lubricant additives. The additive was synthesized through three step chemical functionalization of chicken feathers. The first step involves the reaction between chicken feather powder (CF) and (3-aminopropyl)trimethoxysilane (APTMS) to synthesis CF-APTMS, the second step involves the synthesis of CF-Schiff base by reacting CF-APTMS with 3,5-ditert-butyl-4-hydroxybenzaldehyde, and in the third step, esterification with lauroyl chloride catalyzed by 4-(dimethylamino)pyridine (DMAP) afforded the final product acylated chicken feather Schiff base. The applicability of this CF derived additive as a biodegradable and ecofriendly lubricating oil additive was investigated by testing the antioxidant, lubricity, and anticorrosion properties in polyol which was taken as a reference base fluid. A rotatary bomb oxidation test (RBOT) was used to evaluate the antiox...

Synthesis, Spectroscopic Studies and Antibacterial Activity of New Lauroyl Thiourea Amino Acid Derivatives

Four new thiourea compounds have been successfully synthesized and characterized from combination of lauroyl chloride, ammonium thiocyanate and simple amino acids in acetone. The structure of the respective compounds, namely 3-(3-dodecanoyl-thioureido)propionic acid (R1), 2-(3-dodecanoyl-thioureido)-3-methyl butyric acid (R2), (3-dodecanoyl-thioureido)acetic acid (R3) and 2-(3-dodecanoyl- thioureido)-3-phenyl propionic acid (R4) are confirmed by combination of spectroscopic techniques such as infrared, ultraviolet and nuclear magnetic resonance. The antibacterial activity of these compounds are investigated towards selected bacteria and the results show that compound R4 displays better antibacterial activity compared to R1-R3 and as well as to few reported compounds. Compound R4 shows good antibacterial activity towards two Gram-negative bacteria Escherichia coli and Salmonella typhimurium, with inhibition zone approximately 8 mm wide and minimum inhibitory concentration (MIC) 50 μg/mL, respectively. The good results given by R4 might be attributed by the presence of alkyl and phenyl group that increases the lipophilicity and stability of the compounds.

Synthesis of diacyl amino acid surfactant and evaluation of its potential for surfactant–polymer flooding

Diacyl amino acid surfactant was prepared using lauroyl chloride and l-lysine. The structure of the synthesized surfactant was confirmed by infrared spectroscopy and mass spectroscopy. The ultralow interfacial tension could be achieved when the diacyl amino acid surfactant is mixed with sulfonate in the presence of polymer as well as absence of polymer. Core flood experiments showed that 17.8 % additional oil could be recovered by injection of 0.3 pore volume of surfactant–polymer solution, making the total oil recovery reach 66.1 %.

Structural properties of pepsin-solubilized collagen acylated by lauroyl chloride along with succinic anhydride.

The structural properties of pepsin-solubilized calf skin collagen acylated by lauroyl chloride along with succinic anhydride were investigated in this paper. Compared with native collagen, acylated collagen retained the unique triple helix conformation, as determined by amino acid analysis, circular dichroism and X-ray diffraction. Meanwhile, the thermostability of acylated collagen using thermogravimetric measurements was enhanced as the residual weight increased by 5%. With the temperature increased from 25 to 115 °C, the secondary structure of native and acylated collagens using Fourier transform infrared spectroscopy measurements was destroyed since the intensity of the major amide bands decreased and the positions of the major amide bands shifted to lower wavenumber, respectively. Meanwhile, two-dimensional correlation spectroscopy revealed that the most sensitive bands for acylated and native collagens were amide I and II bands, respectively. Additionally, the corresponding order of the groups between native and acylated collagens was different and the correlation degree for acylated collagen was weaker than that of native collagen, suggesting that temperature played a small influence on the conformation of acylated collagen, which might be concluded that the hydrophobic interaction improved the thermostability of collagen.

Effect of silk protein surfactant on silk degumming and its properties.

The silk protein surfactant (SPS) first used as a silk degumming agent in this study is an amino acid-type anionic surfactant that was synthesized using silk fibroin amino acids and lauroyl chloride. We studied it systematically in comparison with the traditional degumming methods such as sodium carbonate (Na2CO3) and neutral soap (NS). The experimental results showed that the sericin can be completely removed from the silk fibroin fiber after boiling the fibers three times for 30 min and using a bath ratio of 1:80 (g/mL) and a concentration of 0.2% SPS in an aqueous solution. The results of the tensile properties, thermal analysis, and SEM all show that SPS is similar to the NS, far superior to Na2CO3. In short, SPS may be used as an environmentally friendly silk degumming/refining agent in the silk textile industry and in the manufacture of silk floss quilts.

Elaboration of cellulose based nanobiocomposite: Effect of cellulose nanocrystals surface treatment and interface “melting”

The present work deals with the elaboration of nanobiocomposite composed of a cellulose derivative matrix reinforced by cellulose nanocrystals. First, thermoplastic cellulose matrix was obtained by cellulose esterification with lauroyl chloride. Cellulose nanocrystals (NCC), as reinforcement, were obtained by sulfuric acid hydrolysis of cellulose and characterized by AFM. Surface of cellulose nanocrystals (NCC) was then modified by lauroyl chloride in toluene (non swelling solvent), before being used as reinforcing elements in nanobiocomposite. Both cellulose modification and NCC surface modification were proved by different characterizations techniques: FT-IR, contact angle measurements, elemental analysis and thermogravimetric analysis (TGA). Successful surface modification has been shown with rather high degree of substitution (DS). Structural changes of NCC were checked by X-ray Diffraction analyses. Nanocomposites with surface modified and unmodified cellulose nanocrystals as reinforcements were elaborated by casting process. Thermal post-treatment has been performed to “melt” the cellulose derivatives interface. Homogenous nanocomposite films were obtained by film casting process when NCC was grafted, whereas unmodified NCC did not yield the same result. Thermal and mechanical properties were performed with DMA. When NCCs were grafted and thermopressed with the matrix, positive results were obtained proving the efficiency of this new compatibilization process by interface “melting”.

Use of an Acylated Chitosan Schiff Base as an Ecofriendly Multifunctional Biolubricant Additive

Two acylated chitosan Schiff base samples ACSB-1 and -2 were synthesized via a two-step reaction pathway. First the chitosan Schiff base (CSB) was prepared utilizing 3,5-di-tert-butyl-4-hydroxybenzaldehyde. In the second step, esterification with lauroyl chloride catalyzed by 4-(dimethylamino)pyridine (DMAP) in N,N-dimethylacetamide (DMAc) solvent affords the final product acylated chitosan Schiff base (ACSB-1 and -2). The products were identified and characterized by Fourier transform infrared (FT-IR) spectroscopy, CHN analysis, thermogravimetry (TG), X-ray diffraction (XRD), etc. The synthesized compounds were evaluated as multifunctional additives for antioxidant and lubricity properties in N-butyl palmitate/stearate. A rotating pressure vessel oxidation test (ASTM D2272) was used for evaluating antioxidant property. The thermo-oxidative stability of the N-butyl palmitate/stearate oil was increased 1.5 times by using this additive in 3000 ppm concentration of ACSB-2 at 150 °C. Lubricity property was evaluated by using the four ball test (ASTM D4172A) which was performed at 75 °C temperature, frequency of 1200 rpm, and 198 N load for 60 min. The lubricating efficiency of the synthesized sample was estimated by measuring the average wear scar diameter (WSD) of the spherical specimen. The WSD is also found to be decreased significantly by adding these compounds as additives in N-butyl palmitate/stearate. Both samples passed the copper strip corrosion test (ASTM D130) too.

Surface Parameters, Biodegradability, and Antimicrobial Activity of Some Trisodium N-acyl ED3A Surfactants

A new kind of surfactant with chelating properties named N-acyl ethylenediamine triacetate (N-acyl ED3A) of different hydrocarbon chain lengths was synthesized from anhydrous ethylene diamine, fatty acid chlorides (capryloyl, lauroyl, myristoyl, palmitoyl, stearoyl, or oleoyl chloride) and chloroacetic acid. Surface parameters and thermodynamic parameters were investigated. The prepared surfactants were tested for their biodegradability and their antimicrobial activity against different strains of bacteria, yeast, and fungi was investigated.

Preparation of double Pickering emulsions stabilized by chemically tailored nanocelluloses.

Nanocelluloses are bio-based nanoparticles of interest as stabilizers for oil-in-water (o/w) Pickering emulsions. In this work, the surface chemistry of nanocelluloses of different length, nanofibrillated cellulose (NFC, long) and cellulose nanocrystals (CNC, short), was successfully tailored by chemical modification with lauroyl chloride (C12). The resulting nanofibers were less hydrophilic than the original and able to stabilize water-in-oil (w/o) emulsions. The combination of the two types of nanocelluloses (C12-modified and native) led to new surfactant-free oil-in-water-in-oil (o/w/o) double emulsions stabilized by nanocellulose at both interfaces. Characterization was performed with respect to droplet size distribution, droplet stability over time, and stability after centrifugation. Nanocellulose-based Pickering emulsions can be designed with a substantial degree of control, as demonstrated by the stability of the chemically tailored NFC double emulsions. Furthermore, it was demonstrated that increased nanofiber length leads to increased stability.

Evaluation of Cellulose Laurate Esters for Application as Green Biolubricant Additives

Decreasing mineral oil resources, increasing costs, and the need for environmental protection in the use and disposal of lubricants have forced researchers to develop green lubricant formulations. Although many green lubricants consisting of biodegradable base stocks that exhibit excellent properties have been developed, further improvements in their friction and wear performance are required for them to become replacements for mineral-oil-based lubricants. Therefore, in addition to the introduction of biolubricants, the development of new environmentally benign lubricant additives is gaining attention to address the environmental issues. Along these lines, the present investigation involved the synthesis of cellulose laurate by an esterification reaction between microcrystalline cellulose and lauroyl chloride [CH3(CH2)10COOCl] using dimethylacetamide/lithium chloride (DMAc/LiCl) as the solvent and 4-(dimethylamino)pyridine (DMAP) as the catalyst. Different reactions were carried out with varying concentrations of lauroyl chloride. Three samples (Cell Lau-A, -B, and -C) with different degrees of substitution (DS) were then characterized using IR spectroscopy, NMR spectroscopy, TG, SEM, CHN analysis, and XRD to confirm the conversion of the cellulose into cellulose laurate ester. The degrees of substitution (DS) of the synthesized samples were determined using the NMR method. The lubricating efficiencies of the cellulose laurate samples were estimated using a high-frequency reciprocating rig (HFRR) by measuring the wear scar diameters (WSDs) of spherical specimens and the coefficient of friction. The lubricity was found to increase with increasing concentration of cellulose laurate ester in n-butyl palmitate/stearate. Regarding the lubricity of the cellulose laurate esters with different values of DS, the lubricity increased as the DS increased.

표면 개질된 마이크로피브릴화 셀룰로오스를 이용한 폴리아마이드 섬유와의 복합페이퍼 제조 및 특성평가

Microfibrillated cellulose (MFC) was chemically modified with two different silane coupling agents (3-aminopropyltriethoxysilane and 3-mercaptopropyltriethoxysilane) and lauroyl chloride. The surface modification of MFC was confirmed by infrared spectroscopy (FTIR), energy dispersive X-ray spectroscopy (EDX), and contact angle measurements. Composite paper was successfully prepared with surface modified MFC and polyamide (PA) fiber. The surface modification of MFC not only prevented aggregation of MFC but also improved adhesive property between PA fiber and surface modified MFC. It was impossible to prepare papers of only PA fiber because there is no binder to connect PA fibers. That is, surface modified MFC as a binder in PA fiber played a crucial role in making composite paper. Composite paper with silane modified MFC showed higher tensile strength and modulus than composite paper with lauroyl moiety modified MFC. The structure, morphology, and mechanical properties of composite paper were analyzed by scanning electron microscope (SEM) and universal testing machine (UTM).

Surface activity of pepsin‐solubilized collagen acylated by lauroyl chloride along with succinic anhydride

ABSTRACTThe surface activity of pepsin‐solubilized type I collagen acylated by lauroyl chloride and succinic anhydride was investigated in this article. Compared with native collagen, acylated collagen exhibited better surface activity such as oil absorption capacity, emulsion activity and stability, foam expansion, and foam stability but presented lower water absorption capacity. Acylated collagen also had higher emulsion activity and stability than Tween 80, whereas Tween 80 displayed higher foam expansion and stability than acylated collagen. After acylation, the surface tension of collagen decreased with the storage time increased, the hydrophobicity and the wetting power increased with the increase of the concentration. Meanwhile, the emulsion activity and stability of acylated collagen decreased with the increase of NaCl concentration ranging from 20 to 100 mmol/L. Under neutral pH value, acylated collagen reached higher emulsion activity and stability at acylated collagen concentration of 0.4 mg/mL and lower temperature (<35°C). © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 40174.

Synthesis and properties of fatty acid starch esters

Being completely bio-based, fatty acid starch esters (FASEs) are attractive materials that represent an alternative to crude oil-based plastics. In this study, two synthesis methods were compared in terms of their efficiency, toxicity and, especially, product solubility with starch laurate (C12) as model compound. Laurates (DS>2) were obtained through transesterification of fatty acid vinylesters in DMSO or reaction with fatty acid chlorides in pyridine. The latter lead to higher DS-values in a shorter reaction time. But due to the much better solubility of the products compared to lauroyl chloride esterified ones, vinylester-transesterification was preferred to optimize reaction parameters, where reaction time could be shortened to 2h. FASEs C6–C18 were also successfully prepared via transesterification. To determine the DS of the resulting starch laurates, the efficient ATR-IR method was compared with common methods (elementary analysis, 1H NMR). Molar masses (Mw) of the highly soluble starch laurates were analyzed using SEC-MALLS (THF). High recovery rates (>80%) attest to the outstanding solubility of products obtained through transesterification, caused by a slight disintegration during synthesis. Particle size distributions (DLS) demonstrated stable dissolutions in CHCl3 of vinyl laurate esterified – contrary to lauroyl chloride esterified starch. For all highly soluble FASEs (C6–C18), formation of concentrated solutions (10wt%) is feasible.

Preparation of Biodegradable Film from Esterified Corn Husk Cellulose

Cellulose-enrich residue from corn husk was transformed into biodegradable plastic films. After chemical removal of lignin and bleaching the corn husk pulp with hydrogen peroxide, corn husk cellulose powder was received by acid hydrolysis. The esterification of corn husk cellulose was performed using lauroyl chloride as an esterifying agent, toluene and pyridine as solvent and catalyst, respectively. The optimum conditions for esterification were investigated in terms of reaction time and temperature. Chemical structure and solubility of modified cellulose were examined. Cellulose laurate film was obtained by casting method in chloroform solvent. The tensile strength and elongation at break of cellulose laurate film were 5.15 MPa and 6.55%, respectively. The biodegradable of cellulose laurate films in different disposal environments including landfill and wastewater treatment plant for 2 months were investigated. The biodegradation process was followed by measuring the changes in the physical appearance and tensile properties of the films.

Characterization of acylated pepsin-solubilized collagen with better surface activity

A new kind of acylated collagen with water solubility and better surface activity was prepared via reaction of pepsin-solubilized calf skin collagen with lauroyl chloride and succinic anhydride in this paper. The equilibrium surface tension and the isoelectric point were 55.92mN/m and 4.93 respectively, suggesting that acylated collagen had surface activity as well as water solubility. Meanwhile, the results of Fourier transform infrared spectroscopy analyses and electrophoresis patterns demonstrated that the triple helix conformation of collagen was not destroyed, but the subunits of acylated collagen shifted to higher molecular weight than those of native collagen. Scanning electron microscope and differential scanning calorimeter measurements revealed that lyophilized acylated collagen exhibited relatively well-distributed pore structure and its denaturation temperature was about 9.0°C higher than that of native collagen. Additionally, the increase of the diameter of the fibrils was observed by atomic force microscopy. Acylated collagen with water solubility and better surface activity might broaden the application of collagen-based materials to cosmetics, drug delivery and pharmacotherapy.

Synthesis and characterization of flavonoid laurate esters by transesterification

AbstractLaurate esters of catechin and condensed tannins were synthesized by both transesterification and conventional acylation techniques. Transesterification was developed as an alternative route to prepare flavonoid fatty acid esters as a prerequisite to advancing potential applications. Resorcinol, catechin, and two condensed tannins were transesterified with vinyl esters, and the resulting products were compared to those formed with lauroyl chloride. The esterified products, including catechin pentalaurate, were characterized both chemically and thermally. Transesterification produced partially substituted derivatives, with a preference for substitution at the catechol ring. Melt features were identified at or below 50°C, which were dependent upon the level of substitution. In addition, the tannin laurates showed thermal stability to at least 100°C and moderate retention of antioxidant properties. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013

Thermal Hazards Evaluation on the Manufacturing of LPO by DSC for Environment Protection in Material Engineering and its Application

Lauroyl chloride is synthesized by the reaction of phosphorus trichloride and lauroyl acid. It is, in turn, oxidized by a toluene solution of hydrogen peroxide and sodium peroxide to manufacture lauroyl peroxide (LPO). As a retrospective case, a cleaning drum exploded during transfer of the toluene layer including LPO to the filter after separation of the aqueous phase. It is speculated that plant managers did not fully apprehend the hazardous decomposition of LPO, or could not make operators understand it. This study investigated the reaction hazards in the manufacturing process to forestall explosion in the manufacturing of LPO by differential scanning calorimetry (DSC) and TSS model simulations.

Synthesis and Spectral Characterization of Novel 2, 3-Disubstituted Quinazolin-4(3H) one Derivatives

New series of 2,3-disubstituted quinazolin-4(3H)- one were synthesized via the reaction of the readily obtainable 2-thioxo-3-phenyl-quinazolin-4(3H)one 1 with ethyl chloroacetate followed by hydrazinolysis to afford the hydrazide 3 which allowed to react with different electrophilic reagents such as carbon disulphide, phenyl isothiocyanate, β-diketones, anhydrides, acrylonitrile, ethyl cinnamate, dimethyl acetylene dicarboxylate, aldehydes, arylidene malononitrile and lauroyl chloride. Some of the newly synthesized compounds showed promising anti-inflammatory activity.