scholarly journals SINTESIS ASAM 9,10-DIHIDROKSI STEARAT (DHSA) MELALUI HIDROLISA EPOKSIDA DARI OKSIDASI ASAM OLEAT DENGAN ASAM PERFORMAT

REAKTOR ◽  
2016 ◽  
Vol 16 (2) ◽  
pp. 57
Author(s):  
Maisaroh Maisaroh ◽  
Indra Budi Susetyo ◽  
Bayu Rusmandana

SYNTHESIS OF 9,10-DIHYDROXYSTEARIC ACID (DHSA) THROUGH HYDROLYSIS EPOXIDE FROM OXIDATION OLEIC ACID AND PERFORMIC ACID. 9,10-dihydroxy stearic acid (DHSA); C18H36O4 is one of hydroxyl fatty acids with hydroxyl groups (OH) and carboxyl groups (-COOH) cause DHSA have unique properties for many applications including as an emulsifier in the oil phase/gel candles and water in cosmetic formulations. This study investigated the formation of DHSA of from oleic acid and performic acid through epoxidation and hydrolysis reactions. Epoxidation was carried out by reacting the oleic acid with formic acid to form performic acid in situ reaction at a temperature of 60-70oC with stirring in order to minimize byproduct, followed hydrolysis obtained DHSA as powder with melting point 86.5oC, iodine value  0.125 g I2/100 g, acid value 171.53 mg KOH/g, the hydroxyl group observed at the absorption band region of 3345.34 cm-1, LCMS analysis results show peak spetrograms-mass at m/z 317,269, with a value m/z is equivalent to molecular weight DHSA.   Keywords: DHSA; epoxidation; hydrolysis; hydroxyl fatty acids; oleic acid Abstrak Asam 9,10-dihidroksi stearat (DHSA) dengan rumus molekul C18H36O4 merupakan senyawa hidroksil asam lemak dengan gugus hidroksil (-OH) dan karboksil (-COOH) menyebabkan DHSA memiliki sifat unik untuk berbagai aplikasi antara lain sebagai emulsifier antara fasa minyak/lilin gel dan air dalam formulasi kosmetik. Penelitian ini bertujuan untuk menghasilkan DHSA dari asam oleat dan asam performat, melalui tahapan reaksi epoksidasi dan hidrolisa. Epoksidasi asam oleat dengan asam performat yang dibentuk secara in situ dilakukan pada suhu reaksi 60-70oC dengan pengadukan untuk meminimalkan reaksi samping, dilanjutkan dengan hidrolisa epoksida diperoleh DHSA berupa serbuk berwarna putih gading dengan titik leleh 86,5oC, bilangan iod ± 0,125 g I2/100 g, bilangan asam 171,53 mg KOH/g, gugus hidroksil teramati menggunakan FTIR pada bilangan gelombang 3345,34 cm-1, yang diperkuat dengan data kromatogram LC-MS yang memberikan puncak spektrogram-massa pada m/z 317.269, dengan harga m/z yang setara dengan Berat Molekul DHSA. Kata kunci: DHSA; epoksidasi; hidrolisa; hidroksil asam lemak; asam oleat

Author(s):  
Mohd Azril Riduan ◽  
Mohd Jumain Jalil ◽  
Intan Suhada Azmi ◽  
Afifudin Habulat ◽  
Danial Nuruddin Azlan Raofuddin ◽  
...  

Background: Greener epoxidation by using vegetable oil to create an eco-friendly epoxide is being studied because it is a more cost-effective and environmentally friendly commodity that is safer than non-renewable materials. The aim of this research is to come up with low-cost solutions for banana trunk acoustic panels with kinetic modelling of epoxy-based palm oil. Method: In this study, the epoxidation of palm oleic acid was carried out by in situ performic acid to produce epoxidized palm oleic acid. Results: Banana trunk acoustic panel was successfully innovated based on the performance when the epoxy was applied. Lastly, a mathematical model was developed by using the numerical integration of the 4th order Runge-Kutta method, and the results showed that there is a good agreement between the simulation and experimental data, which validates the kinetic model. Conclusion: Overall, the peracid mechanism was effective in producing a high yield of epoxy from palm oleic acid that is useful for the improvement of acoustic panels based on the banana trunk.


Author(s):  
Carrillo W ◽  
Carpio C ◽  
Morales D ◽  
Vilcacundo E ◽  
Álvarez M ◽  
...  

  Objective: The aim of this work was to determine the fatty acids content in corn seeds oil (Zea mays) sample cultivated in Ecuador.Methods: Corn oil was obtained from corn oil seeds using the cold pressing method. Methyl esters fatty acids analysis were carried out using the gas chromatography (GC) method with a mass selective detector and using the database library NIST 14.L to identify the compounds present in the corn seed oil.Results: Methyl esters fatty acids were identified from corn (Z. mays) seeds using the GC mass spectrometer (GC-MS) analytical method. Fatty acids were analyzed as methyl esters on a capillary column DB-WAX 122-7062 with a good separation of palmitic acid, stearic acid, oleic acid, elaidic acid, linoleic acid, arachidic acid, and linolenic acid. The structure of methyl esters fatty acids was determined using the GS-MS method. Corn oil has a high content of linoleic acid (omega 6) with a value of 52.68% of the total content of fatty acids in corn oil and 29.70% of oleic acid (omega 9) of the total content of fatty acids in corn oil. The sample presented a value of 12.57% of palmitic acid.Conclusions: Corn oil shows a good content of fatty acids omega 6 and 9. The higher value was of omega 6 with 52.68% content. Corn oil has a good proportion of polyunsaturated of lipids (53.80%) and 14.86% of saturated lipids.


Author(s):  
Md. Delwar Hossain ◽  
Kamal Uddin Ahmed ◽  
Mst. Farhana Nazneen Chowdhury ◽  
Alak Barman ◽  
Arif Ahmed ◽  
...  

With a view to studying the qualitative features and the variations in fatty acid composition of 6 rapeseed (B. campestris and B. napus) and mustard (B. juncea) varieties, an experiment was conducted. Among these varieties, BARI Sarisha-14 presented the value of 168.4 which was recorded the highest. Both BARI Sarisha-11 and BARI Sarisha-14 was found with the highest iodine value of 39.44; and the highest amount of acid value was recorded from BARI Sarisha-11 (1.867). Gas-liquid chromatographic (GLC) method has been used to determine the composition of essential fatty acid in the seeds of Brassica spp. (L.). From the GLC analysis, it was found that erucic acid, oleic acid, linoleic acid and lenolenic acid were the prime fatty acids in all the varieties. Erucic acid was in the range of 41.11 – 51.28%, oleic acid was the highest both in BARI Sarisha-11 and BARI Sarisha- 13 contained (18.69%), while BARI Sarisha-9 contained the highest amount of the unsaturated linoleic (17.75%)  and linolenic (15.83%) acids. Moreover, palmitic acid, stearic acid and archidic acid were also present in small amount.


Author(s):  
David R. Dalton

Grape leaves are thin and flat. As is common among leaves in general, they are composed of different sets of specialized cells. Today, on average, sunlight reaching their surface is about 4% ultraviolet (UV) (<400 nm), 52% infrared (IR) (>750 nm) and 44% visible (VIS) radiation. Little of the UV and IR are used by plants. As with other leaves that are green, only the red and blue ends of the visible part of the electromagnetic spectrum are absorbed, thus leaving green available by reflection and transmission. On the surface of the leaf (Figure 8.1), the cells of the outermost layer (the epidermis) are designed to protect the inner cells where the workings needed for gathering the sunlight used for photosynthesis and other chemistry necessary to the life of the plant are found. That is, the more delicate cells, beneath the epidermis, are involved in production of carbohydrates as well as the movement of nutrients in and products out of the leaf. The epidermis, exposed to the atmosphere, has cells that are usually thicker and are covered by a waxy layer made up of long- chain carboxylic acids that have hydroxyl groups (–OH) at or near their termini. These so-called omega hydroxy acids can then form esters using the hydroxyl group of one and the carboxylic acid of the next. This yields long-chain polyester polymers called “cutin.” As indicated in the earlier discussion of cells and, in particular, regarding the fatty acids of cell walls, the fatty acids found in the epidermis generally consist of an even number of carbon atoms, and for cutin, the sixteen carbon (palmitic acid) family (Figure 8.2) and the eighteen carbon family (oleic acid bearing a double bond or the saturated analogue stearic acid) are common. While one terminal hydroxyl group is usual (e.g., 16-hydroxypalmitic acid, 18-hydroxyoleic acid, or its saturated analogue 18-hydroxystearic acid) more than one (allowing for cross-linking) is not uncommon (e.g., 10,16-dihydroxypalmitic and 9,10,18-trihydroxystearic acid).


Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1882 ◽  
Author(s):  
Elisabetta Brenna ◽  
Danilo Colombo ◽  
Giuseppe Di Lecce ◽  
Francesco G. Gatti ◽  
Maria Chiara Ghezzi ◽  
...  

A chemo-enzymatic approach for the conversion of oleic acid into azelaic and pelargonic acid is herein described. It represents a sustainable alternative to ozonolysis, currently employed at the industrial scale to perform the reaction. Azelaic acid is produced in high chemical purity in 44% isolation yield after three steps, avoiding column chromatography purifications. In the first step, the lipase-mediated generation of peroleic acid in the presence of 35% H2O2 is employed for the self-epoxidation of the unsaturated acid to the corresponding oxirane derivative. This intermediate is submitted to in situ acid-catalyzed opening, to afford 9,10-dihydroxystearic acid, which readily crystallizes from the reaction medium. The chemical oxidation of the diol derivative, using atmospheric oxygen as a stoichiometric oxidant with catalytic quantities of Fe(NO3)3∙9∙H2O, (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO), and NaCl, affords 9,10-dioxostearic acid which is cleaved by the action of 35% H2O2 in mild conditions, without requiring any catalyst, to give pelargonic and azelaic acid.


1994 ◽  
Vol 122 (3) ◽  
pp. 423-428 ◽  
Author(s):  
M. J. Hinds ◽  
B. Singh

SUMMARYStudies were conducted to evaluate amounts of fatty acids in the oil as possible indicators of crop maturity in the groundnut, cultivar NC2, grown in St Vincent, Eastern Caribbean. Percentage fatty acids in oil of the composite samples of seeds collected between 99 and 141 days after planting for a period of 3 years (1985–87) was determined by gas-liquid chromatography. Results indicated variation in the amounts of individual fatty acids with crop maturity. There were definite trends, however, with respect to oleic and linoleic acids. As seeds matured, percentage oleic acid increased and percentage linoleic acid decreased, and consequently, the oleic:linoleic acid ratio in oil of the composite seeds increased significantly. The percentage oleic acid peaked significantly at a value of 55.8 ± 0.59 at optimum harvest dates. The results clearly suggested therefore that percentage oleic acid in oil could be used as a reliable reaping index for groundnut.


2011 ◽  
Vol 35 (1) ◽  
pp. 121-124 ◽  
Author(s):  
Mohammad Mizanur Rahman ◽  
Sudhangshu Kumar Roy ◽  
Mohammad Shahjahan

The fatty acid composition of the ripe seed oil of Nyctanthes arbor-tristis L. (Bengali: Seuli) were determined by GLC. The major constituent of the oil was found to be stearic acid, 39.06%. The relative percentages of other major fatty acids were found to be lauric acid, (4.46); linoleic acid, (7.89); oleic acid, (7.97). The yield of the seed oil was found to be 7.29% on extraction with pet-ether (b. p. 40°C - 60°C). Acid value of seed oil was found to be 55.44 and suggests that this oil is inedible.DOI: http://dx.doi.org/10.3329/jbas.v35i1.7977Journal of Bangladesh Academy of Sciences, Vol.35, No.1, 121-124, 2011


2011 ◽  
Vol 675-677 ◽  
pp. 495-498
Author(s):  
Yong Feng Li ◽  
Yi Xing Liu ◽  
Yun Lin Fu ◽  
Qing Lin Wu ◽  
Xiang Ming Wang

Bio-based materials such as wood, bamboo, bio-straw material are vulnerable to degradation by microorganisms and susceptible to change in dimension under humidity, which greatly reduced their service life. In this study, a novel thought was inspired from the unique porous structure of bio-based material that durability of wood may be capable of being improved by generating polymer in situ the special structure. Maleic anhydride (Man) and Styrene (St) were used to penetrate into wood for further copolymerization. SEM observation shows that polymer filled in wood porous structure and tightly contacted wood matrix (i.e. biopolymers), indicating strong interaction between them. FTIR analysis indicates that polymer chemically grafted onto wood matrix by reaction of anhydride group and hydroxyl group. As the amount of hydroxyl groups greatly reduced for their reacting with polymer, the dimensional stability of wood immersing in water was improved; and as the reaction of wood with polymer, the biopolymers were wrapped by resultant polymer, preventing the sample from attack of microorganisms, thus decay resistance of treated wood against microorganisms was greatly improved. Both of them contributed to the improvement of wood durability.


2020 ◽  
Vol 17 (4) ◽  
pp. 412-422
Author(s):  
Grzegorz Lewandowski ◽  
Marlena Musik ◽  
Kornelia Malarczyk-Matusiak ◽  
Łukasz Sałaciński ◽  
Eugeniusz Milchert

A comprehensive review of recent existing methods of epoxidation of vegetable oils, unsaturated fatty acids and alkyl esters of unsaturated fatty acids has been presented. The importance of epoxidized vegetable oils and their applications in the production of polyols and polyurethanes was discussed. Interests of researchers have been mainly focused on the development of advantageous technological parameters of vegetable oils epoxidation. The epoxidations with peracetic acid or performic acid generated in situ were mainly performed in the presence of strongly acidic catalysts. The influence of process variables such as temperature, stirring speed, the molar ratio of carboxylic acid and hydrogen peroxide to the amount of ethylenic unsaturation, amount of catalyst and reaction time on the course of epoxidation has been investigated.


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