The Application and Systhesis of Arachidic acid

Arachidic acid is present in certain oils and fats at a content of approximately 1% or lower. Besides being isolated through hydrolysis of peanut oil, it can also be separated from fatty acid mixtures generated by paraffin wax oxidation. Arachidic acid is used in the manufacturing of cosmetics, printing inks, lubricants, surfactants, and other products.

The Applation on LB membranes

The condom with anti-viral properties is made by Langmuir-Blodgett coating onto latex rubber of 1 mole part CeO fullerene and 4 mole parts arachidic acid. Onto the subphase and inside the adjustable perimeter floating on the surface of the subphase were placed a few drops (150 μl) of a concentrated solution of I mole part CgQ 25 fullerene and 4 parts arachidic acid in benzene. One hour was allowed to pass, to ensure complete evaporation of the benzene. The perimeter was adjusted until the fullerene plus arachidic acid formed a close-packed and ordered arrangement, this being established by compressing the perimeter such as to maintain a surface pressure of 30 milliNewtons/m. This arrangement is believed to be of vertically aligned fatty acid molecules in a 30 close-packed ordered arrangement on the subphase (water) surface, with the fullerene molecules on tog. This arrangement is transferred "as is" to a solid substrate dipped into the Langmuir-Blodgett trough.^[1]

The Applation on printing ink

In organic printing ink systems, silver ion reactive seeds are highly active and prone to oxidation. This accelerates the aggregation and sedimentation of these unstable metallic silver species, consequently reducing the stable printing capability of the ink. This is detrimental to advancing the industrial manufacturing process of flexible electronic devices. The invention by Wang Yan et al. provides a method for the arachidic acid-specific self-assembly modification of silver ions within printing inks. The addition of arachidic acid does not adversely affect the stable silver ions in the ink. Instead, it exerts a specific protective effect solely on these unstable silver ions through surface self-assembly modification, thereby reducing their flocculation tendency and ensuring the printing quality of flexible electronic devices.^[2]

The Applation on surfactant

Wang Ying et al. disclosed an eco-friendly reactive nonionic surfactant, primarily comprising the following components in parts by weight:Glycerol: 50-60 parts;Lewis base: 10-12 parts;Arachidic acid: 22-26 parts;Stabilizer: 2-4 parts;Methyl eicosapentaenoate: 10-20 parts.By optimizing the surfactant formulation, the invention exhibits excellent dispersibility, emulsification capacity, and stability while being environmentally benign. All raw materials possess superior biodegradability, abundant availability, and low cost. This approach reduces formulation expenses while enhancing emulsion performance, yielding significant economic and social benefits.^[3]

The Applation as a composition of emulsions

Edible aerated oil-in-water emulsions like whipped cream are well known food products comprising a continuous water phase and oil droplets suspended in the aqueous phase. Bunge Loders Croklaan B.V. discloses a emulsions contain water, stearic acid (C18:0) and arachidic acid (C20:0); palmitic acid (C16:0) and lauric acid (C12:0).^[4]

The Applation as oil stabilizer

Oils that have inherently poor low temperature stability and have crystallized during transport or storage must undergo extra treatment such as mixing, heating, and/or dilution to melt the oil for use. These processing steps cause unwanted costs and additional working time for the user. Vegetable oils can also undergo further processing such as clarification or de-waxing in order to lower the oil's 30 crystallization point to keep the oil liquid at a broader temperature range. Clarification or dewaxing, however, alter the composition of the oil by removing some substances and waxy compounds. Additional treatments include the addition of clarifying agents, addition of processing aids, extraction with large volumes of solvent, and/or exposure to high temperatures. Even though the final product will have an improved low temperature stability, the oil and its important natural products could have been 35 changed, reduced, or lost. SIRAK, Sofia found oil contain a certain amount of palmitic acid (C16:0) and/or stearic acid (C18:0) and/or eicosanoic acid (C20:0) storage stabilizer.^[5]

The Synthetic method of Arachidic acid^[6]

Fig.1. The Synthetic Route of Arachidic acid

Step 1: Preparation of dimethyl 2-octadecylmalonate

A solution of dimethyl malonate (119 g) and dimethyl formamide (300 mL) was stirred at about 25 °C for 5-10 minutes. Potassium carbonate (207 g) and DMF (100 mL) was added to the reaction mass and stirred for 1 hour. To the above reaction 10 mass, 1-bromooctadecane (100 g) was slowly added, followed by dimethyl formamide (100 mL). The reaction mass was heated to 80-90 °C and stirred at the same temperature for 2 hours and 30 minutes. The reaction mass was cooled slowly to 25-30 °C and quenched with water (1 L). The reaction mass was stirred for 1 hour at the same temperature and the precipitated compound was filtered. The product 15 was washed with water (500 mL) and sucked dried. The wet compound was taken in methanol (300 mL) and the reaction mass was heated to reflux for about 1 hour. The reaction mass was cooled slowly to 25-30 °C and stirred for 1 more hour. The reaction mass was again cooled slowly to 5-15 °C and stirred for 30 minutes at that temperature. The precipitated compound was filtered and washed with chilled 20 methanol (100 mL). The compound was dried under vacuum for 21 hours to provide the title compound.

Step 2: Preparation of methyl arachidate

To a mixture of dimethyl 2-octadecylmononate(Ia)(112 g) and dimethyl sulfoxide(1120 mL), sodium chloride(68.1 g) and water(10.49 g/mL) was added. The reaction mass was heated to 140-150°C for about 15 hours. The reaction mass was cooled to 25-35°C and water(560 mL) was added to the reaction mass. The reaction mass was stirred at the same temperature for about 4 hours and filtered. The wet compound was added to a mixture of methanol(560 mL) and heptane(56 mL). The reaction mass was heated to reflux for 30 minutes and then cooled to 30-35°C and 5 stirred for 90 minutes.The reaction mass was further cooled to 5-15°C and stirred for 2 hours. The precipitated compound was filtered, washed with methanol(112 mL) and dried overnight under vacuum to provide the title compound.

Step 3: Preparation of arachidic acid

To a solution of methyl arachidate(IIa)(80 g) and tetrahydrofuran(400 mL), water(160 mL was added. A solution of sodium hydroxide, prepared by slowly adding sodium hydroxide(16.17 g) in water(160 mL), was added to the above solution 15 maintaining the temperature of the reaction mass at 20-40°C. Water(80 mL) was further added to the reaction mass and heated to 60-70°C. The reaction mass was stirred for 2 hours at the same temperature and cooled to 45-55°C. Water(80 mL) was added to the reaction mass and the temperature of the reaction mass was cooled to 25-35°C.The pH of the reaction mass was adjusted to 6.5-7.5 by slowly adding 20 diluted hydrochloric acid(IN) and stirred the reaction mass for 2 hours and 30 minutes. The precipitated compound was filtered. The wet compound was added to a mixture of tetrahydrofuran(80 mL) and acetone(400 mL). The reaction mass was heated to 50-60°C and stirred for 40 minutes. The reaction mass was cooled to 25- 35°C and stirred for 40 minutes. The reaction mass was further cooled to 5-10°C 25 and the precipitated compound was filtered, washed with acetone(80 mL) and dried at 40-50°C under vacuum for 9 hours to afford the desired compound.

References

[1]British Technology Group Ltd., Medical membranes with anti-viral properties, [P]WO9521637

[2]Wang Yan, Method for the specific self-assembly modification of silver ions in printing ink by arachidic acid, [P] CN118440535

[3]Wang, Ying, Ecological response nonionic surfactant with biodegradability from glycerol and arachidic acid, [P] CN109092207

[4]Bunge Loders Croklaan B.V, Aerated fat emulsion, [P] WO2021148540

[5]SIRAK, Sofia, Vegetable oils with improved low temperature storage stability, [P]WO20190154775

[6]Hindupur, Rama Mohan, Process for preparation of arachidic acid, [P] WO2021205351