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Polyamide
Published in Antonio Paesano, Handbook of Sustainable Polymers for Additive Manufacturing, 2022
The molecular formula and weight of CO are C57H104O9 and 933.45 g/mol, respectively (PubChem n.d.), and its composition includes the following fatty acids: 90% ricinoleic, 4% linoleic, 3% oleic, 1% stearic, and < 1% linolenic. CO’s importance for the chemical industry resides in its high content of ricinoleic acid (RA), namely in the presence of the hydroxyl group in RA and the double bond of the ester linkage that together enable to perform a variety of chemical reactions, modifications, and transformations involved in formulating numerous products, such as coatings, inks, lubricants, and paints (Patel et al. 2016). CO features density of 0.959 g/cm3, viscosity of 6–8 poises at 25°C, and boiling point of 313°C at 760 mm Hg (PubChem, n.d.; Kazeem et al. 2014). CO is extracted from seeds by mechanical pressing, solvent extraction, or a combination of both methods (Dasari and Goud 2013). CO can be chemically transformed through a number of methods not only into PA but also polyethers, polyesters, PUs, and interpenetrating polymer networks (Mubofu 2016). Depending on the processing route followed, CO generates two monomers: 11-aminoundecanoic acid to formulate PA 11, or sebacic acid to formulate PA 6,10 and PA 10,10.
Core Eudicots: Dicotyledons IV
Published in Donald H. Les, Aquatic Dicotyledons of North America, 2017
Euphorbiaceae are important economically as the source of natural rubber (Hevea brasiliensis) and ingredients used in the manufacture of tung oils (Vernicii fordii). Although the family (especially Euphorbia) contains a number of poisonous species, there are also several edible plants such as Manihot esculenta (cassava or manioc), which are rich in carbohydrates (starch). This plant is also the source of tapioca. Many species are grown as ornamentals, primarily in the genera Acalypha, Codiaeum, Croton, Euphorbia (which includes Poinsettia), Jatropha, and Ricinis. The latter genus is also notorious as the source of a highly toxic lectin known as ricin, which is produced by the seed endosperm of Ricinus communis. The pressed seeds of this species also yield castor oil, which is the primary source of ricinoleic acid.
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Published in Brajendra K. Sharma, Girma Biresaw, Environmentally Friendly and Biobased Lubricants, 2016
Kenneth M. Doll, Bryan R. Moser, Zengshe Liu, Rex E. Murray
The principal fatty acid in castor oil is ricinoleic acid (Figure 5.4), which is both hydroxylated and unsaturated. As a consequence of its unique multifunctional composition, castor oil is used extensively as an industrial oil. In addition to sebacic acid mentioned previously, ricinoleic acid is used to produce a variety of products including estolides via polycondensation; polyols by transesterification with diols or other polyhydroxylated compounds; 10-hydroxydecanoic acid by low-temperature alkali cleavage; and 10-undecenoic (undecylenic) acid from pyrolysis [68,77,78]. Undecylenic acid is used as a platform chemical for the production of numerous monomers [79]. For example, polyamide 11 is obtained from 11-aminoundecanoic acid, which is prepared via an 11-bromo intermediate [68,77,78]. Dienoic monomers suitable for free radical or acyclic diene metathesis polymerization have also been prepared from undecylenic acid. These include allyl, vinyl, acrylic, and methacrylic ethers and esters, all of which have applications in the coatings industry [80]. Dienes suitable for acyclic diene metathesis polymerization include 10-undecenyl undecylenate and undecylenic acid moieties esterified to phosphorus-containing heteroaromatic cores as comonomers for flame-resistant polyesters [81,82]. Finally, a variety of renewable monomers can be prepared via thiol-ene click chemistry in which thiolated compounds are added to undecylenic acid via a free radical mechanism to yield anti-Markovnikov products [83]. Such monomers are useful for production of ultraviolet (UV)–curable resins and coatings. Specific examples of monomers from undecylenic acid include those derived by addition of butanedithiol, thioacetic acid, thioglycerol, 4-hydroxybutanethiol, and methyl 2-mercaptoacetate, among others [83–85]. Methyl 9-decenoate (Figure 5.5 and next subsection), prepared by cross metathesis of methyl oleate with ethene (ethenolysis), represents the 10-carbon analogue of methyl 10-undecenoate [86].
Investigation of palm-castor oil blends as base stocks of bio-lubricants for industrial applications
Published in Energy Sources, Part A: Recovery, Utilization, and Environmental Effects, 2022
T. K. K. S. Pathmasiri, G. I. P. Perera, R. Gallage
Table 2 shows the initial chemical analysis of the selected two oils, palm and castor. Palm oil is composed of about 40% saturated fatty acids, 50% monounsaturated fatty acids and 10% polyunsaturated fatty acids while palmitic, oleic and linoleic is being the main contributor for each category. Castor oil is composed of about 4% saturated fats, 88% mono-unsaturated fats and 8% polyunsaturated. Ricinoleic acid is the key mono-unsaturated fat element in castor oil. Figure 1 shows the key fatty acids molecular structures of palm and castor oils. Table 3 shows the physio-chemical properties of palm oil, castor oil, palm-castor oil blends and three selected commercially available oils, H68, SAE30 and SAE40.
Synthesis of biodiesel via pre-blending of feedstocks: an optimization by the polynomial curve fitting method
Published in Biofuels, 2021
Tarique Panhwar, Sarfaraz Ahmed Mahesar, Aftab Ahmed Kandhro, Aijaz Laghari, Syed Tufail Hussain Sherazi, A. E. Atabani
Knowledge of fatty acid composition of feedstock is essential as it has a direct influence on fuel-related parameters [37]. As shown in Table 2, ricinoleic acid (88.5%) is the dominant fatty acid in castor oil, followed by oleic (4.3%), linoleic (3.3%), stearic (0.9%), eicosenoic (1.5%) and palmitic (0.8%) acids. These results are in agreement with earlier studies [34,36] which report that ricinoleic acid has the highest percentage (82.88% and 87%, respectively). A high content of ricinoleic acid indicates good-quality oil but the presence of the hydroxyl group leads to high viscosity, specific gravity and solubility in alcohol [43]. GC-MS analysis of cottonseed oil showed that the dominant fatty acid was linoleic acid (47.73%), followed by palmitic (26.48%), oleic (20.91%), stearic (2.7%), myristic (0.65%) and palmitoleic (0.37%) acids. These findings are in agreement with earlier studies which indicated that linoleic acid constitutes 55% [30] and 54% [34,44] of cottonseed oil, while palmitic, oleic, stearic, myristic and palmitoleic acids constitute 24.4, 17.2, 2.2, 0.8 and 0.4% [30] and 22, 19, 3, 1 and 1% [34,44], respectively.
Biocatalytic production of ricinoleic acid from castor oil: augmentation by ionic liquid
Published in Chemical Engineering Communications, 2020
Abir Lal Bose, Debajyoti Goswami
Table 1 describes impacts of organic solvents as additives on lipase catalyzed castor oil hydrolysis. In castor oil, ricinoleic acid constitutes of nearly 90% of total fatty acid profile; i.e., most of the castor oil molecules contain ricinoleic acid in all three positions of its triglyceride structure. Naturally, extent of hydrolysis provides with a rough estimate of ricinoleic acid recovery. As choice of organic solvent was the initial step, extent of hydrolysis was considered instead of ricinoleic acid recovery. In absence of organic solvent, the extent of hydrolysis was 17.57% in 2 h under certain process conditions. Organic solvents like tert–amyl alcohol and n–hexanol drastically deactivated lipase activity, resulting in only 14.62% and 5.85% hydrolysis in 2 h, respectively, under same reaction conditions. But, hexane, isooctane, diethyl ether, tert-butanol, and toluene enhanced hydrolysis; of which toluene was the best, leading to 30.18% hydrolysis in 2 h. So, toluene was selected as the organic solvent to carry out further experiments. Generally organic solvent has the tendency to denature lipase. Higher the exposure to the solvent, higher is lipase denaturation; lower will be extent of reaction (hydrolysis). Simultaneously, the solvent solubilizes substrate (oil) for hydrolysis and reduces viscosity of oil phase such that mixing between oil and aqueous phase (containing lipase) is facilitated. As a consequence, extent of hydrolysis rises. So, the effect of organic solvent depends on type of lipase, type of substrate (oil) and time of exposure. In the present work involving porcine pancreas lipase, toluene possibly helped to reduce viscosity of oil phase (containing castor oil) to maximum extent and thus facilitated reaction, but lipase denaturation was low as time of exposure was low (2 h).