Search

Castor oil is one important raw material that could serve as a renewable feedstock for industries in the age of exhausting fossil fuels. The chemical composition of oil and the structure of hydroxyl fatty acid are responsible for its unique physicochemical properties. The oil has diverse applications from pharmaceuticals to polyamides, from the manufacturing of ski boots to durable frames, and from lubricants to laxatives. The present review gives an insight into the physicochemical properties of castor oil and its application. The oil is used for the production of a great variety of its derivatives. Out of many derivatives of castor oil, four are produced and utilized at a larger scale. The names of the four derivates are ricinoleic acid, sebacic acid, undecylenic acid, and γ‐decalactone. The review will aim toward an insight into the evolved techniques for the manufacturing of these derivatives of castor oil, the biotechnological route of production, and metabolic engineering approaches. Though the industrial significance of castor oil and its derivatives had been known for ages, methods for their production are continuously changing. [ABSTRACT FROM AUTHOR]

This work describes the development and characterization of mechanical flexible epoxy resins based on epoxidized vegetable oils (EVO) and sebacic acid. Different oil types (linseed oil, hempseed oil, and soybean oil) with varying epoxy equivalent weight (EEW) were used. Formulation and processing parameters were systematically optimized by differential scanning calorimetry and Fourier‐transform infrared spectroscopy. The effect of the EVO type and EEW on thermo‐mechanical and mechanical properties were investigated by dynamic mechanical analysis and tensile tests at different temperatures. The EVO type had a strong effect on the thermo‐mechanical and mechanical properties of the resin. However, for the investigated commercial epoxidized linseed oils, the EEW had no effect on these properties. With epoxidized linseed oil the highest Tg and the best mechanical properties (highest tensile strength and toughness) were achieved. [ABSTRACT FROM AUTHOR]

BACKGROUND: As a bio‐derived platform molecule, levulinic acid can be converted to liquid fuels with similar components as aviation kerosene after undergoing aldol self‐condensation and successive hydrodeoxygenation reactions. In view of its complicated composition, sebacic acid was selected as a model compound for the investigating the hydrodeoxygenation performance of the product of levulinic acid self‐condensation in this work. RESULTS: Firstly, a series of supported metal catalysts were screened and characterized by temperature‐programmed desorption of NH3 and CO2, X‐ray diffraction, transmission electron microscopy, X‐ray photoelectron spectroscopy and CO pulse chemisorption. The results indicated that Ru/TiO2 showed the highest selectivity to total long‐chain alkanes at the complete conversion of sebacic acid. Then, the influence of preparation conditions on the catalytic performance of Ru/TiO2 and the effect of reaction conditions on the hydrodeoxygenation of sebacic acid were studied. On this basis, possible hydrodeoxygenation reaction routes were discussed. CONCLUSION: The excellent catalytic performance of Ru/TiO2 is attributed to a moderate degree of Ru reduction and dispersion, along with its unique acid–base characteristics. © 2022 Society of Chemical Industry (SCI). [ABSTRACT FROM AUTHOR]

A simple and alternate organic synthetic route for sebacic acid, a high value ten‐carbon aliphatic dicarboxylic acid from castor oil is described in this study. Castor oil methyl esters are purified to obtain methyl ester of ricinoleic acid that is used as the starting material for the preparation of sebacic acid. The hydroxyl group of methyl ricinoleate is oxidized to corresponding 12‐oxo derivative followed by isomerization of the cis 9, 10 olefinic bond to trans 10, 11 isomer. The isomerized compound is subjected to dihydroxylation followed by oxidative cleavage and subsequent methylation to obtain dimethyl decanedioate. The dimethyl decanedioate is finally hydrolyzed to obtain sebacic acid. The intermediate compounds and final product are purified and characterized by chromatographic and spectral analysis. The final compound is analyzed by 1H and 13C‐NMR as well as high resolution mass spectrometry and compared with standard compound for the confirmation of the structure. Practical Applications: The design and preparation of sebacic acid by the novel alternate route is described. Castor oil, a renewable source, is utilized as the raw material for the preparation of sebacic acid. Isomerization of the 9, 10 cis bond to 10, 11 trans bond is the key step in the synthesis of sebacic acid. The chemical transformation of castor oil to sebacic acid by newer route is investigated. [ABSTRACT FROM AUTHOR]

Castor oil and its three derivatives including methyl ricinoleate, sodium ricinoleate and ricinoleic acid were used as the raw material for alkali fusion to prepare sebacic acid. The reaction parameters including catalyst, ratio of oleochemicals/NaOH, reaction time and reaction temperature were optimized. It was found that Pb3O4 (1%) showed the best catalytic performance, and 553 K was considered as the most suitable reaction temperature. The oleochemicals/NaOH ratios of 15:14, 15:14, 15:12 and 15:14 were determined as the optimal ratio for alkali fusion of castor oil, methyl ricinoleate, sodium ricinoleate and ricinoleic acid, respectively. In addition, the optimal reaction time of alkali fusion of castor oil was 5 hours, and that of its derivatives was 3 hours. The maximum yield in sebacic acid of 68.8%, 77.7%, 80.1%, 78.6% can be obtained by using castor oil, methyl ricinoleate, sodium ricinoleate and ricinoleic acid as the raw material, respectively. High purity of sebacic acid was confirmed by GC and melting point analysis. ICP‐OES results illustrated that the content of Pb in sebcic acid was less than 1 mg kg−1. Separating glycerol from castor oil was beneficial for alkali fusion, by which, the yield of sebacic acid was increased of approximately 10%, and the reaction time was reduced from 5 to 3 hours. This study provided guiding significance for the future industrial production of sebacic acid. [ABSTRACT FROM AUTHOR]

The potential of sebacic acid as a corrosion inhibitor for hot‐dip galvanized steel in 0.1 M NaCl solution has been investigated. Different concentrations of the organic acid have been tested in order to understand the inhibition mechanism of the compound. The electrochemical test revealed a competitive mechanism between the dissolution of the metal in the acidified solution and the inhibition provided by the dicarboxylic species. The formation of a whitish layer consisting of zinc carboxylates and corrosion products was proved by means of scanning electron microscopy (SEM) investigation combined with Fourier transform infrared (FT‐IR) analysis. A bidentate bridging coordination between the Zn(II) and the carboxylic species is suggested. [ABSTRACT FROM AUTHOR]

In situ forming implants (ISFIs) appear to be a convenient drug delivery system, alternative to conventional preformed implants and microparticles for parenteral drug delivery applications. It has been shown that they offer several advantages including easy and minimally invasive application, potential for local/site‐specific drug delivery that allows reduction of side effects associated with systemic administration of drug. A few ISFI formulations based on poly(α‐hydroxy acids), solidifying by solid phase separation, are currently commercially available. In this work, polyesters based on sebacic acid, isosorbide, and optionally 1,2‐propanediol were synthesized and characterized. Poly(isosorbide sebacate‐co‐1,2‐propylene sebacate) (PISEBPG) was chosen as an essential constituent of new ISFI formulations dedicated to controlled release of doxycycline hyclate (DOXY). Basic characteristics of new ISFI formulations were investigated. In particular, the influence of addition of a relatively hydrophobic cosolvent (triacetin, TA) to a more hydrophilic 1‐methyl‐2‐pyrrolidone (NMP) as well as the presence of calcium carbonate (CAC) on the morphology of resulted depots and DOXY release profile was evaluated. Scanning electron microscopy (SEM) analysis revealed that the presence of TA resulted in more porous morphology of the depots. DOXY has been releasing continuously from depots in vitro within 12 weeks depending on the composition. The release profile of the PISEBPG‐based formulation containing CAC indicates that it could be useful where short‐term (up to 14 d), rapid release of the antibiotic is required, while formulation without CAC, where after 21 days about 50% of the drug loaded may still be available for release, may be better for the long‐term delivery of DOXY. [ABSTRACT FROM AUTHOR]

Abstract: Renewable resources, including vegetable oils, can be used as feedstock for the manufacture of pressure sensitive adhesives (PSA) that can compete with those derived from petrochemical sources, but with the environmental benefit of being sustainable. Completely bio‐based PSA with tunable viscoelastic properties were synthesized from mixtures of epoxidized soybean oil and sebacic acid by a solvent‐free one‐step reaction, in the absence of catalyst. Curing conditions and pot‐life were determined for formulations with stoichiometric acid/epoxy ratio. Curing time ranged from the gel point (tgel) to tgel + 30 min at the selected temperature (170 °C) to study the correlation between the reaction, rheological behavior, and potential adhesive performance. These renewable PSA can be tailored by controlling the curing parameters according to the desired application, since the rheological profile and gel content were greatly dependent on the curing conditions. In particular, the obtained adhesives cured at 170 °C between 65 and 75 min showed the best balance between tack and cohesion. [ABSTRACT FROM AUTHOR]

ABSTRACT Novel fully renewable AA-BB type non-isocyanate polyhydroxyurethanes were synthesized by the classical reaction between a diamine and a dicyclocarbonate. Sebacic acid was first reacted with an excess of glycerol carbonate, in presence of DCC and DMPA, leading to a renewable dicyclocarbonate monomer. Then, this monomer was reacted with several renewable diamines, in presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), as organocatalyst, to afford linear and branched polymers. The obtained materials exhibited Tg values varied from −27 to −8 °C, Tm values varying from 100 to 165 °C, and thermal stabilities above 200 °C. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 758-764 [ABSTRACT FROM AUTHOR]

An efficient synthetic method was developed for the preparation of 1-octacosanol (C28-alcohol) from commercially available lipid-based intermediates namely sebacic acid (decanedioic acid) and stearyl alcohol. The key step in the synthesis is the preparation of tert-butyl dimethyl octacos-10-enyloxy silane from 10- tert-butyl dimethyl silanyloxy decanal and octadecyl triphenylphosphonium bromide salt employing Witting reaction. This product on simultaneous hydrogenation of double bond and deprotection of tert-butyldimethylsilyl protecting group in a single step on treatment with Pd/C and H2 in methanol at ambient temperature resulted octacosanol in 95% yields. The products were characterised by IR, 1H NMR, and GC-MS analysis. [ABSTRACT FROM AUTHOR]

Even-number, medium-chain dicarboxylic acids (DAs), naturally occurring in higher plants, are a promising alternative energy substrate. Unlike the homologous fatty acids, DAs are soluble in water as salts. They are β-oxidized, providing acetyl-CoA and succinyl-CoA, the latter being an intermediate of the tricarboxylic acid cycle. Sebacic acid and dodecanedioic acid, DAs with 10 and 12 carbon atoms respectively, provide 6.6 and 7.2 kcal g−1 each; therefore, their energy density is intermediate between glucose and fatty acids. Dicarboxylic acids have been proved to be safe in both experimental animals and humans, and their use has recently been proposed in diabetes. Studies in animals and humans with type 2 diabetes showed that oral administration of sebacic acid improved glycaemic control, probably by enhancing insulin sensitivity, and reduced hepatic gluconeogenesis and glucose output. Moreover, dodecanedioic acid intake reduced muscle fatigue during exercise in subjects with type 2 diabetes, suggesting an improvement of energy utilization and 'metabolic flexibility'. In this article, we review the natural sources of DAs, their fate in animals and humans and their effect in improving glucose metabolism in type 2 diabetes. [ABSTRACT FROM AUTHOR]

Polyanhydrides are largely used in biomedical and pharmaceutical fields because of their biodegradability and controlled degradation. In this work, oligomers were investigated as film binders for environmental applications. To overcome the main disadvantages of polyanhydrides (low solubility in common solvents and high melting points), oligomers based on sebacic acid were prepared. Characterization was carried out by nuclear magnetic resonance and electrospray ionization to obtain chemical structures of the products. The formation of weak interactions, which confer cohesion between chains, allows film properties to be observed. The impact of the solvent polarity on the specific organization was investigated by a combination of focused methods: capillary viscosimetry, IR spectroscopy, polarized light microscopy, and X-ray diffraction. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012 [ABSTRACT FROM AUTHOR]

Polyesteranhydrides synthesized by the transesterification of ricinoleic acid and sebacic acid followed by anhydride polymerization were examined as potential controlled delivery carrier for tamsulosin. Polymers containing 70% ricinoleic acid are liquid at body temperature and semisolid at room temperature. It was found that upon addition of the liquid polymer to water it solidifies to form a stable semisolid polymer. Tamsulosin hydrochloride (TAM), a highly selective α-adrenoreceptor antagonist that has been used for the treatment of lower urinary tract symptoms suggestive of benign prostatic hyperplasia (LUTS/BPH), was incorporated in the polymers (2-20% w/w) and its release in buffer solution was monitored. TAM was released for over 24 days while the polymer carrier was being degraded. Hydrolysis of formulations was studied by monitoring the weight loss of the samples and the changes in the polymer molecular weight. TAM formulations stability in p(SA-RA) 30:70 under different temperatures was evaluated. The release rate of the drug from polymer was found to be affected by drug content: the higher the content, the faster was the release. Also, hydrolysis of formulation containing tamsulosin was faster due to the hydrophility of the drug. The drug formulation was found to be stable for a period of 6 months. Moreover, after subcutaneously injection into mice, the drug-loaded formulation becomes into gel and remains in the site of the injection. To conclude, Poly(sebacic acid-co-ricinoleic-acid) containing ≥ 70% ricinoleic acid are injectable biodegradable polymers and are suitable candidates for the delivery of TAM for long acting therapy. Copyright © 2010 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]

The preparation of dibasic acid-containing soy phospholipid was made by transesterification reaction with alkyl ester of diabasic acid with both lipase and alkoxide as a catalyst. The extent of incorporation of a dibasic acid varied with the molecular size of the dibasic acid. The extent of incorporation in soy phospholipids was 4–13% in the case of adipic acid and 9–20% in the case of sebacic acid. The surface-active properties of these modified soy phospholipids were examined and were found to be different from those of the original (unmodified) soy phospholipid. The interfacial properties such as critical micelle concentration (CMC), γCMC, surface excess concentration Γmax, and minimum area per molecule (Å), and thermodynamic parameters such as standard free energy of micellization, were found to depend on the hydrophobic part of the dibasic acids. [ABSTRACT FROM AUTHOR]

In this study, materials with low melting temperatures and high toughness are developed for orthopedic applications. A series of an aliphatic copolyester based on sebacic acid (SeA), a green resource, is copolymerized with ethylene glycol, trimesic acid, aminocaproic acid, and adipic acid (AA) to produce poly(ethylene sebacate‐co‐ethylene adipate) (PESA) with various molar ratios through melt polymerization. Thermal characterizations of the PESA copolyesters are tuned with SeA and AA in varying molar ratios, exhibiting a crystalline phase with a lower degree of perfection. The melting point (Tm) and crystallization temperature (Tc) of the copolyesters are observed at 60–70 and 30–40 °C, respectively. Furthermore, a high Young's modulus ranging between 140 and 200 MPa is observed, which could be attributed to the 3D network structure formed by the trimesic acid unit used as a cross‐linking agent. Within the authors' research group, the PESA copolyesters are adopted to reinforce the mechanical properties of a 3D air mesh fabric as a composite application. Also, the highly breathable and low‐weight characteristics of 3D fabric with PESA copolyesters render them suitable for replacing traditional plaster in the future. [ABSTRACT FROM AUTHOR]