Lucas Degang, Gabriela Auricchio, Vanessa Kristine de Oliveira Schmidt, Isabela Karina Della-Flora, Cristiano José de Andrade
Abstract Biosurfactants are amphiphilic compounds synthesized from plants and microorganisms and are known for their high biodegradability, low toxicity, and eco-friendliness. They have diverse applications in industrial and environmental fields, including oil recovery, bioremediation, and cleaning up hydrocarbons from polluted areas. Surfactin is a potent lipopeptide biosurfactant produced by Bacillus subtilis bacteria. In this study, we produced surfactin by B. subtilis using cassava wastewater as the fermentation medium. This production was monitored by high performance liquid chromatography (HPLC). Approximately 600 mg L−1 of surfactant was produced. The oil displacement test was then performed to evaluate the effectiveness of crude and purified surfactin compared to a synthetic surfactant and a biosurfactant. Three types of surfactants were tested: the synthetic surfactant sodium lauryl sulfate (SDS), the commercial biosurfactant rhamnolipid (Rh), and surfactin in its crude form and purified one – after acid precipitation. The analysis results indicated that surfactin, in both its crude and purified forms, was more effective at dispersing oil than the other surfactants tested, even at lower concentrations. This suggests that biosurfactants have great potential as a more sustainable and effective alternative to petroleum-derived synthetic surfactants. Surfactin can be applied without the need for downstream processes.
{"title":"Oil displacement properties of surfactin: a comparative study","authors":"Lucas Degang, Gabriela Auricchio, Vanessa Kristine de Oliveira Schmidt, Isabela Karina Della-Flora, Cristiano José de Andrade","doi":"10.1515/tsd-2023-2525","DOIUrl":"https://doi.org/10.1515/tsd-2023-2525","url":null,"abstract":"Abstract Biosurfactants are amphiphilic compounds synthesized from plants and microorganisms and are known for their high biodegradability, low toxicity, and eco-friendliness. They have diverse applications in industrial and environmental fields, including oil recovery, bioremediation, and cleaning up hydrocarbons from polluted areas. Surfactin is a potent lipopeptide biosurfactant produced by Bacillus subtilis bacteria. In this study, we produced surfactin by B. subtilis using cassava wastewater as the fermentation medium. This production was monitored by high performance liquid chromatography (HPLC). Approximately 600 mg L−1 of surfactant was produced. The oil displacement test was then performed to evaluate the effectiveness of crude and purified surfactin compared to a synthetic surfactant and a biosurfactant. Three types of surfactants were tested: the synthetic surfactant sodium lauryl sulfate (SDS), the commercial biosurfactant rhamnolipid (Rh), and surfactin in its crude form and purified one – after acid precipitation. The analysis results indicated that surfactin, in both its crude and purified forms, was more effective at dispersing oil than the other surfactants tested, even at lower concentrations. This suggests that biosurfactants have great potential as a more sustainable and effective alternative to petroleum-derived synthetic surfactants. Surfactin can be applied without the need for downstream processes.","PeriodicalId":22258,"journal":{"name":"Tenside Surfactants Detergents","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2023-07-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45134601","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract The influence of replacing water with isopropanol (IP) on the rheological properties of aqueous solutions containing wormlike micelles (WLMs) prepared by mixing cetyltrimethylammonium bromide (CTAB) and sodium salicylate (NaSal) at 25 °C was investigated. Viscosity of CTAB aqueous solutions exhibits two maxima and one minimum with increasing amounts of NaSal, consisting of entangled WLMs. When water is replaced by increasing amount of IP, the viscosity maxima and the minimum changes drastically. The elastic plateau modulus G° of these solutions remains almost the same with increasing IP contents (up to ∼5 wt%), whereas their relaxation time changes drastically. Critical micelle concentration (CMC) of CTAB has increased with further IP addition, indicating an increase in the micellar hydrophilicity. For WLMs at minimum viscosity, increasing addition of IP (>5.0 %) to WLMs at maximum and minimum viscosities, leads to a drastic decrease in the elastic modulus G°, indicating the formation of smaller micellar aggregates. The influence of IP as a co-solvent on the WLMs rheological properties is also compared to that of glycerol and 1,3 butanediol (1,3 BD) for the same NaSal/CTAB viscoelastic system.
{"title":"Influence of isopropanol on the rheological behavior of wormlike micelles","authors":"R. Abdel-Rahem, K. Clinckspoor, H. Hoffmann","doi":"10.1515/tsd-2023-2501","DOIUrl":"https://doi.org/10.1515/tsd-2023-2501","url":null,"abstract":"Abstract The influence of replacing water with isopropanol (IP) on the rheological properties of aqueous solutions containing wormlike micelles (WLMs) prepared by mixing cetyltrimethylammonium bromide (CTAB) and sodium salicylate (NaSal) at 25 °C was investigated. Viscosity of CTAB aqueous solutions exhibits two maxima and one minimum with increasing amounts of NaSal, consisting of entangled WLMs. When water is replaced by increasing amount of IP, the viscosity maxima and the minimum changes drastically. The elastic plateau modulus G° of these solutions remains almost the same with increasing IP contents (up to ∼5 wt%), whereas their relaxation time changes drastically. Critical micelle concentration (CMC) of CTAB has increased with further IP addition, indicating an increase in the micellar hydrophilicity. For WLMs at minimum viscosity, increasing addition of IP (>5.0 %) to WLMs at maximum and minimum viscosities, leads to a drastic decrease in the elastic modulus G°, indicating the formation of smaller micellar aggregates. The influence of IP as a co-solvent on the WLMs rheological properties is also compared to that of glycerol and 1,3 butanediol (1,3 BD) for the same NaSal/CTAB viscoelastic system.","PeriodicalId":22258,"journal":{"name":"Tenside Surfactants Detergents","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2023-07-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48057569","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract In the present work, the anionic biomass surfactant cardanol sulfonate (CDS) was compounded in different molar fractions (α1) with the commonly used amphoteric surfactant lauryl amidopropyl betaine (LAB) and the nonionic surfactant alkyl glycoside (APG), respectively. By measuring the surface tension of the binary compound system, the relationship between the surface chemical properties of the compound system and α1 was investigated, and then the synergistic parameters and thermodynamic parameters of the compound system were calculated. The results showed that both CDS/LAB and CDS/APG systems exhibited non-ideal mixing behavior. The CDS/LAB compound system has the best synergistic effect when the two components were mixed in a 1:1 molar ratio, corresponding to a CMC of 3.06 × 10−4 mol L−1 and a γCMC of 32.60 mN m−1. The formation of mixed micelles was a spontaneous exothermic process driven by enthalpy. The CDS/APG compound system at the molar ratio of n(APG): n(CDS) = 9:1 has a more significant synergistic effect, corresponding to a CMC of 1.13 × 10−4 mol L−1 and a γCMC of 29.10 mN m−1. The application performance of the compound systems was the best at the optimal molar ratio, which confirms the existence of synergistic effect in the compound systems.
{"title":"Study on the synergistic effect of the binary compound system of cardanol sulfonate","authors":"Yue Liu, Wan-Hong Li, Haiyan Gao, Hujun Xu","doi":"10.1515/tsd-2023-2529","DOIUrl":"https://doi.org/10.1515/tsd-2023-2529","url":null,"abstract":"Abstract In the present work, the anionic biomass surfactant cardanol sulfonate (CDS) was compounded in different molar fractions (α1) with the commonly used amphoteric surfactant lauryl amidopropyl betaine (LAB) and the nonionic surfactant alkyl glycoside (APG), respectively. By measuring the surface tension of the binary compound system, the relationship between the surface chemical properties of the compound system and α1 was investigated, and then the synergistic parameters and thermodynamic parameters of the compound system were calculated. The results showed that both CDS/LAB and CDS/APG systems exhibited non-ideal mixing behavior. The CDS/LAB compound system has the best synergistic effect when the two components were mixed in a 1:1 molar ratio, corresponding to a CMC of 3.06 × 10−4 mol L−1 and a γCMC of 32.60 mN m−1. The formation of mixed micelles was a spontaneous exothermic process driven by enthalpy. The CDS/APG compound system at the molar ratio of n(APG): n(CDS) = 9:1 has a more significant synergistic effect, corresponding to a CMC of 1.13 × 10−4 mol L−1 and a γCMC of 29.10 mN m−1. The application performance of the compound systems was the best at the optimal molar ratio, which confirms the existence of synergistic effect in the compound systems.","PeriodicalId":22258,"journal":{"name":"Tenside Surfactants Detergents","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2023-07-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45783583","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
G. Kaur, R. Kaur, Jasmeet Kaur, Harleen Singh, H. Kumar, Pooja Sharma
Abstract The study aims to scrutinize the mixed micellization and interfacial behavior of two 1-alkyl-3-butylimidazolium based surface-active ionic liquids (SAILs) i.e., 1-decyl-3-butylimidazolium bromide [C10bim][Br] and 1-tetradecyl-3-butylimidazolium bromide [C14bim][Br] under the influence of streptomycin sulphate (SS) drug in 5 mM concentration in aqueous media. Imidazolium-based SAILs have unique physicochemical properties and greater surface activity than conventional surfactants, which allows them to increase drug permeability, making them better drug carriers than currently available formulations. To fully utilize [C14bim][Br] and [C10bim][Br] in drug delivery applications, deep insight into the interactions occurring in the mixed micellar [C10bim][Br]/[C14bim][Br] systems in the drug’s presence are necessary to be examined. Thus, the study is conducted using conductivity and surface tension measurement techniques to fully exploit the self-assembly, micellization behavior and interactions occurring in the pure and mixed micellar system of [C10bim][Br]/[C14bim][Br] in water and 5 mM of SS solution in aqueous media. For this, various thermodynamic, surface-active and mixed micellar parameters of micellization have been calculated and analyzed with respect to change in mole fraction, temperature and addition of SS in solution.
{"title":"Analyzing the modulations induced in the mixed micellar behavior of 1-alkyl-3-butylimidazolium based surface-active ionic liquids with an antibiotic drug in aqueous media","authors":"G. Kaur, R. Kaur, Jasmeet Kaur, Harleen Singh, H. Kumar, Pooja Sharma","doi":"10.1515/tsd-2023-2512","DOIUrl":"https://doi.org/10.1515/tsd-2023-2512","url":null,"abstract":"Abstract The study aims to scrutinize the mixed micellization and interfacial behavior of two 1-alkyl-3-butylimidazolium based surface-active ionic liquids (SAILs) i.e., 1-decyl-3-butylimidazolium bromide [C10bim][Br] and 1-tetradecyl-3-butylimidazolium bromide [C14bim][Br] under the influence of streptomycin sulphate (SS) drug in 5 mM concentration in aqueous media. Imidazolium-based SAILs have unique physicochemical properties and greater surface activity than conventional surfactants, which allows them to increase drug permeability, making them better drug carriers than currently available formulations. To fully utilize [C14bim][Br] and [C10bim][Br] in drug delivery applications, deep insight into the interactions occurring in the mixed micellar [C10bim][Br]/[C14bim][Br] systems in the drug’s presence are necessary to be examined. Thus, the study is conducted using conductivity and surface tension measurement techniques to fully exploit the self-assembly, micellization behavior and interactions occurring in the pure and mixed micellar system of [C10bim][Br]/[C14bim][Br] in water and 5 mM of SS solution in aqueous media. For this, various thermodynamic, surface-active and mixed micellar parameters of micellization have been calculated and analyzed with respect to change in mole fraction, temperature and addition of SS in solution.","PeriodicalId":22258,"journal":{"name":"Tenside Surfactants Detergents","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2023-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46956571","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract The impact of different concentrations of sodium carboxymethyl cellulose (NaCMC) on the micellization process in cationic, ester-functionalized, ethyl-substituted imidazolium-based surface-active ionic liquids (SAILs) ([C n Eeim]Br where, n = 12, 14, 16) were investigated using specific conductivity and surface tension measurements at 298 K. The study focused on determining the critical micelle concentration (CMC) of the three pure SAILs and their mixtures with NaCMC to evaluate various thermodynamic and interfacial parameters. The results showed that the CMC values decreased significantly with increasing hydrophobicity of the SAILs, while the CMC increased with a gradual increase in the NaCMC mole fraction in the SAIL–NaCMC mixed systems. It was observed that the excess free energy of micellization ( ∆ G e x m ${{increment}G}_{ex}^{m}$ ) and the minimum free energy of surface at equilibrium ( ∆ G min s ${{increment}G}_{mathrm{min}}^{s}$ ) exhibited an opposite behaviour, indicating that the formed mixed micelles were stable while the formed surface was unstable. The results of this study are useful for evaluating the properties of SAIL–NaCMC mixed systems to improve and better understand their applications in the food, medical and cosmetic industries.
摘要使用298℃下的比电导率和表面张力测量，研究了不同浓度的羧甲基纤维素钠（NaCMC）对阳离子、酯官能化、乙基取代咪唑基表面活性离子液体（SAILs）（[Cn-Eeim]Br，其中n=12，14，16）中胶束化过程的影响 K.本研究的重点是确定三种纯SAIL及其与NaCMC的混合物的临界胶束浓度（CMC），以评估各种热力学和界面参数。结果表明，在SAIL–NaCMC混合体系中，CMC值随着SAIL疏水性的增加而显著降低，而CMC值随着NaCMC摩尔分数的逐渐增加而增加。观察到胶束化的过量自由能（∆G e x m$｛｛increment｝G｝_｛ex｝^｛m｝$）和平衡时表面的最小自由能（⏴G min s$｛增量｝G}_｛mathrm｛min｝｝^｝s｝美元）表现出相反的行为，表明形成的混合胶束是稳定的，而形成的表面是不稳定的。本研究的结果有助于评估SAIL–NaCMC混合体系的性能，以改进和更好地了解其在食品、医疗和化妆品行业的应用。
{"title":"Investigation of aggregation behavior and surface properties of cationic surface-active ionic liquids and sodium carboxymethylcellulose mixed systems","authors":"Safiya Ahsan, Arun Dhanagar, A. Shaheen","doi":"10.1515/tsd-2022-2487","DOIUrl":"https://doi.org/10.1515/tsd-2022-2487","url":null,"abstract":"Abstract The impact of different concentrations of sodium carboxymethyl cellulose (NaCMC) on the micellization process in cationic, ester-functionalized, ethyl-substituted imidazolium-based surface-active ionic liquids (SAILs) ([C n Eeim]Br where, n = 12, 14, 16) were investigated using specific conductivity and surface tension measurements at 298 K. The study focused on determining the critical micelle concentration (CMC) of the three pure SAILs and their mixtures with NaCMC to evaluate various thermodynamic and interfacial parameters. The results showed that the CMC values decreased significantly with increasing hydrophobicity of the SAILs, while the CMC increased with a gradual increase in the NaCMC mole fraction in the SAIL–NaCMC mixed systems. It was observed that the excess free energy of micellization ( ∆ G e x m ${{increment}G}_{ex}^{m}$ ) and the minimum free energy of surface at equilibrium ( ∆ G min s ${{increment}G}_{mathrm{min}}^{s}$ ) exhibited an opposite behaviour, indicating that the formed mixed micelles were stable while the formed surface was unstable. The results of this study are useful for evaluating the properties of SAIL–NaCMC mixed systems to improve and better understand their applications in the food, medical and cosmetic industries.","PeriodicalId":22258,"journal":{"name":"Tenside Surfactants Detergents","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2023-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45825325","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
H. A. Aziz, R. Yusoff, N. G. Cheng, Z. Idris, Nur Aainaa Syahirah Ramli
Abstract A heterogeneous transesterification over a Zn-doped CaO catalyst was developed as a new alternative route to conventional homogeneous catalysis for the production of N-methyldiethanolamine-based esterquats. In this study, the optimum heterogeneous transesterification conditions for the production of N-methyldiethanolamine di-ester, a precursor of esterquats, in high yield were determined. At a temperature of 143 °C, a vacuum of 288 mbar, a molar ratio of 2:1 (methyl ester:N-methyldiethanolamine) and a catalyst dosage of 6 %, a maximum N-methyldiethanolamine di-ester yield of 83 % was obtained. The reused catalyst showed consistent activity in three consecutive runs, demonstrating the robustness of the Zn-doped CaO catalyst in the transesterification process. This route can reduce production costs due to the reusability of the catalyst and the elimination of water consumption in the neutralisation process for catalyst removal.
{"title":"Production of high content of N-methyldiethanolamine di-ester via heterogeneous transesterification","authors":"H. A. Aziz, R. Yusoff, N. G. Cheng, Z. Idris, Nur Aainaa Syahirah Ramli","doi":"10.1515/tsd-2022-2494","DOIUrl":"https://doi.org/10.1515/tsd-2022-2494","url":null,"abstract":"Abstract A heterogeneous transesterification over a Zn-doped CaO catalyst was developed as a new alternative route to conventional homogeneous catalysis for the production of N-methyldiethanolamine-based esterquats. In this study, the optimum heterogeneous transesterification conditions for the production of N-methyldiethanolamine di-ester, a precursor of esterquats, in high yield were determined. At a temperature of 143 °C, a vacuum of 288 mbar, a molar ratio of 2:1 (methyl ester:N-methyldiethanolamine) and a catalyst dosage of 6 %, a maximum N-methyldiethanolamine di-ester yield of 83 % was obtained. The reused catalyst showed consistent activity in three consecutive runs, demonstrating the robustness of the Zn-doped CaO catalyst in the transesterification process. This route can reduce production costs due to the reusability of the catalyst and the elimination of water consumption in the neutralisation process for catalyst removal.","PeriodicalId":22258,"journal":{"name":"Tenside Surfactants Detergents","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2023-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45759070","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract Ionic liquids (IL) have attained immense interest as substitutes for conventionally available surfactants because of their exceptionally favorable physicochemical properties. Most synthesized IL surfactants are not environmentally benign, and even utilizing high concentration, they form unstable micelles. In this regard, we have synthesized biocompatible and halogen free choline based ionic liquids by varying anions (choline oleate and cholinium bis(2-ethylhexyl) sulfosuccinate) and further investigated their micellization behavior in presence of the drug Cetrizine dihydrochloride. Characterizations of these synthesized ionic liquids were performed utilizing 1HNMR spectroscopy. The thermodynamic investigation and determination of various surface-active parameters were based on tensiometry and conductometric titrations. The CMC value of choline oleate ([CHO][Ole]) was found to be lower than that of [Cho][AOT] and thus it has a better surface activity. The thermodynamic parameters (ΔGm0${{Delta}G}_{m}^{0}$, ΔHm0${{Delta}H}_{m}^{0}$, and ΔSm0${{Delta}S}_{m}^{0}$) signifies spontaneous, stable, exothermic and entropy driven nature of micellization process. The various interfacial and surface parameters have been evaluated employing tensiometry. These environmentally friendly ionic liquids have been utilized as substitute for conventional surfactants including their applications in biology and pharmaceutical industries.
{"title":"Thermodynamics and micellization behavior of choline based ionic liquids in presence of drug Cetrizine dihydrochloride","authors":"Pooja Sharma, J. Kaur, R. Kaur, H. Kumar, G. Kaur","doi":"10.1515/tsd-2023-2506","DOIUrl":"https://doi.org/10.1515/tsd-2023-2506","url":null,"abstract":"Abstract Ionic liquids (IL) have attained immense interest as substitutes for conventionally available surfactants because of their exceptionally favorable physicochemical properties. Most synthesized IL surfactants are not environmentally benign, and even utilizing high concentration, they form unstable micelles. In this regard, we have synthesized biocompatible and halogen free choline based ionic liquids by varying anions (choline oleate and cholinium bis(2-ethylhexyl) sulfosuccinate) and further investigated their micellization behavior in presence of the drug Cetrizine dihydrochloride. Characterizations of these synthesized ionic liquids were performed utilizing 1HNMR spectroscopy. The thermodynamic investigation and determination of various surface-active parameters were based on tensiometry and conductometric titrations. The CMC value of choline oleate ([CHO][Ole]) was found to be lower than that of [Cho][AOT] and thus it has a better surface activity. The thermodynamic parameters (ΔGm0${{Delta}G}_{m}^{0}$, ΔHm0${{Delta}H}_{m}^{0}$, and ΔSm0${{Delta}S}_{m}^{0}$) signifies spontaneous, stable, exothermic and entropy driven nature of micellization process. The various interfacial and surface parameters have been evaluated employing tensiometry. These environmentally friendly ionic liquids have been utilized as substitute for conventional surfactants including their applications in biology and pharmaceutical industries.","PeriodicalId":22258,"journal":{"name":"Tenside Surfactants Detergents","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2023-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44400236","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract Methyl ester sulfonate (MES) is considered as an efficient and novel surfactant used as main active ingredient in cleansing products. MES is often produced via sulfonation of methyl ester (ME) with sulfonating agent. In this study, ME was synthesized from used cooking oil (UCO) via transesterification and then sulfonated to produce MES using two different sulfonating agents (chlorosulfonic acid (CSA) and sodium bisulfite (NaHSO3)). The influence of various factors (temperature, sulfonating agent/ME molar ratio and time) on MES yield was investigated. Analysis of optimal MES samples was carried out using different techniques (GC-FID, FTIR and 1H NMR). The maximum MES yield of 88.2 % was achieved with CSA/ME molar ratio of 1.2:1 at 70 °C for 3 h while the highest MES yield of 79.4 % was obtained with NaHSO3/ME molar ratio of 1.2:1 at 90 °C for 3 h. FTIR and 1H NMR analyses revealed the presence of methyl (CH2− asymmetric and CH2− symmetric stretching vibrations), esters (C=O, C–O, and O–CH3), and sulfonate (S=O) groups in MESCSA and MESNaHSO3 samples, thereby affirming the desired product. Surface tension analysis showed that the MESCSA and MESNaHSO3 have low critical micelle concentrations of 0.079 g/L and 0.14 g/L, respectively while the corresponding surface tensions were 51.9 mN/m and 30.94 mN/m for MESCSA and MESNaHSO3 respectively.
{"title":"Comparing the performances of different sulfonating agents in sulfonation of methyl esters synthesized from used cooking oil","authors":"A. Yusuff, Favour B. Bode‐Olajide","doi":"10.1515/tsd-2023-2513","DOIUrl":"https://doi.org/10.1515/tsd-2023-2513","url":null,"abstract":"Abstract Methyl ester sulfonate (MES) is considered as an efficient and novel surfactant used as main active ingredient in cleansing products. MES is often produced via sulfonation of methyl ester (ME) with sulfonating agent. In this study, ME was synthesized from used cooking oil (UCO) via transesterification and then sulfonated to produce MES using two different sulfonating agents (chlorosulfonic acid (CSA) and sodium bisulfite (NaHSO3)). The influence of various factors (temperature, sulfonating agent/ME molar ratio and time) on MES yield was investigated. Analysis of optimal MES samples was carried out using different techniques (GC-FID, FTIR and 1H NMR). The maximum MES yield of 88.2 % was achieved with CSA/ME molar ratio of 1.2:1 at 70 °C for 3 h while the highest MES yield of 79.4 % was obtained with NaHSO3/ME molar ratio of 1.2:1 at 90 °C for 3 h. FTIR and 1H NMR analyses revealed the presence of methyl (CH2− asymmetric and CH2− symmetric stretching vibrations), esters (C=O, C–O, and O–CH3), and sulfonate (S=O) groups in MESCSA and MESNaHSO3 samples, thereby affirming the desired product. Surface tension analysis showed that the MESCSA and MESNaHSO3 have low critical micelle concentrations of 0.079 g/L and 0.14 g/L, respectively while the corresponding surface tensions were 51.9 mN/m and 30.94 mN/m for MESCSA and MESNaHSO3 respectively.","PeriodicalId":22258,"journal":{"name":"Tenside Surfactants Detergents","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2023-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41905109","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
I. Ali, Sarzamin Khan, Samrein Ahmed, Serab Khan, H. Ali, Raiz Ullah Shafiullah, M. Shah, Z. A. Shah
Abstract In order to improve the solubility and bioavailability of poorly water-soluble drugs, the synthesis of cost-effective nonionic surfactants has been the subject of greater scientific interest. The present study focuses on the synthesis of sulfonyl chloride derivatives as nonionic surfactants (surfactant 1 and surfactant 2) and their evaluation for the preparation of a clarithromycin-loaded niosomal drug delivery system. Surfactants 1 and 2 were characterised by EI-MS and 1H NMR spectroscopy. The shape and size of the drug-loaded niosomal vesicles from the synthesised surfactants were examined by atomic force microscopy (AFM) and revealed a round morphology with an average size of (230.8 ± 2.35) nm and (248.1 ± 2.54) nm for the vesicles of surfactant 1 and surfactant 2, respectively. The zeta potential of surfactant 1-based niosomal vesicles was (– 7.70 ± 1.00) mV and that of surfactant 2 was (−14.6 ± 1.08) mV. The lower zeta potential values for surfactant 1 and surfactant 2-based niosomal vesicles showed that these vesicles were neutral and relatively stable. The vesicles of surfactant 1 and 2 have a capacity to entrap the drug of about (62 ± 2.26) % and (69.67 ± 3.23) %, respectively. The vesicles of surfactant 1 released the largest amount of drug, i.e. (70.00 ± 2.45) % at pH 1.2. Biocompatibility in human blood and toxic effects on various cell lines were also studied for surfactants 1 and 2, and they were found to be biocompatible and non-cytotoxic.
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