Punicic acid (omeg a-5) obtained from pomegranate seeds by using supercritical fluid extraction and its production method
Supercritical fluid extraction with carbon dioxide addresses the degradation issues of punicic acid in conventional methods, achieving high yield and quality while reducing environmental impact.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- TGM BY TEKNOGIDA MUHENDISLIK & BIYOTEKNOLOJI YATIRIMLAR SANAYI LTD SIRKETI
- Filing Date
- 2026-01-22
- Publication Date
- 2026-07-30
AI Technical Summary
Conventional extraction methods for punicic acid from pomegranate seeds cause structural degradation and oxidation due to high temperatures and exposure to oxygen, leading to low yields and environmental hazards, while existing solvents are costly and harmful.
Supercritical fluid extraction using carbon dioxide as a solvent under high pressure and low temperature conditions preserves the molecular structure of punicic acid, achieving nearly 99% yield with minimal environmental impact.
The method maintains the quality and nutritional value of punicic acid, reduces processing time, and recycles pomace into valuable products like animal feed or biogas, providing economic and environmental benefits.
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Abstract
Description
[0001] PUNICIC ACID (OMEGA-5) OBTAINED FROM POMEGRANATE SEEDS BY USING SUPERCRITICAL FLUID EXTRACTION AND ITS PRODUCTION METHOD TECHNICAL FIELD
[0002] The invention relates to punicic acid (omega-5), obtained at high concentrations from pomegranate seeds by using supercritical fluid extraction, and to the method of producing the same. In this method, carbon dioxide is used as the sole solvent under high pressure and low temperature conditions.
[0003] PRIOR ART
[0004] Pomegranate seed (Punica granatum) and its components have attracted considerable attention in recent years as a natural source believed to have beneficial effects on cardiovascular health. The antioxidants, flavonoids, and polyphenols present in pomegranate may play an important role in the prevention and treatment of cardiovascular diseases. The presence of strong antioxidant compounds in pomegranate seeds may reduce oxidative stress and inflammation by neutralizing free radicals. A reduction in oxidative stress may help prevent myocardial ischemia / reperfusion injury.
[0005] Pomegranate seed may help reduce LDL (bad cholesterol) levels, increase nitric oxide production that promotes vasodilation, decrease inflammatory markers, and improve cardiac muscle function. Thus, it enhances blood flow and supports heart health.
[0006] Pomegranate seeds contain a very high amount of the omega-5 fatty acid known as punicic acid (PA). Omega-5 fatty acid has been shown to be very safe in terms of toxicity and to yield positive outcomes in many serious conditions such as obesity, cardiovascular diseases, Alzheimer’s disease, osteoarthritis, and diabetes. Punicic acid (PA) must be obtained through extraction processes.
[0007] Punicic acid is exposed to high temperatures and oxygen during steam distillation, leading to oxidation; its structure is degraded in solvent extraction due to exposure to chemical solvents; and in cold pressing, the surface temperature increases due to friction, causing exposure to oxygen and subsequent oxidation. For these reasons, there is a need to use alternative extraction methods to obtain punicic acid.Furthermore, considering the hazardous nature, high cost, and negative environmental impacts of most organic and inorganic liquid solvents currently in use, the adoption of new techniques and solvents is of great importance. For this purpose, supercritical fluid extraction technology has been developed. In supercritical fluid extraction processes, the non-toxic nature of the extraction agent, its chemical inertness toward food components, the absence of solvent residues in the extract, its environmental friendliness, low cost, and the reduction of extraction time have made this method highly significant.
[0008] Supercritical extraction processes involve high-pressure and high-precision systems, in which control and monitoring mechanisms are critical. In addition, optimization of the supercritical extraction process and the proper selection of the solvent are of great importance. Compared to conventional extraction methods, supercritical extraction technology is more efficient and environmentally friendly. This technology provides higher efficiency, quality, and nutritional value in the processing of oilseeds and their residues. Therefore, it is widely used in fields such as the food industry, cosmetics sector, and biofuel production. Moreover, purification studies of plant-based, oil-soluble seed components possessing “health benefits” and therapeutic or supportive therapeutic properties using supercritical extraction technology are of great importance. In other words, there is a need for studies focusing on obtaining multiple high value-added raw materials from a single seed through the use of advanced technologies.
[0009] BRIEF DESCRIPTION OF THE INVENTION
[0010] The invention relates to punicic acid (omega-5 fatty acid) obtained at high concentrations from pomegranate seeds by using supercritical fluid extraction, and to the method for producing the same. In this method, carbon dioxide is used as the sole solvent under high pressure and low temperature conditions. Through the present invention, omega-5 fatty acids purified by supercritical extraction technology are obtained, and depending on the composition of the remaining pomace, plant-based protein (from oil seeds), gluten-free flour, or dietary fiber may also be produced.
[0011] In the supercritical carbon dioxide method used in the present invention, the process is carried out under low temperature and oxygen-free conditions; therefore, omega-5 is extracted in its most natural form without any damage to its molecular structure.When the temperature of a pure substance exceeds its critical temperature and its pressure exceeds its critical pressure, the fluid in this region is defined as a “supercritical fluid.” In this region, supercritical fluids exhibit very strong solvating power, combining properties of both liquids and gases. Due to general availability, commercial viability, and ease of application, carbon dioxide (CO2), ethanol, propane, n-pentane, acetone, and water are commonly preferred as supercritical fluids.
[0012] Under supercritical conditions (Tc>32°C and Pc>72 bar) CO2 enters the supercritical phase. CO2behaves similarly to gases due to its low viscosity and high diffusivity, and similarly to liquids due to its high density and strong solvating power. These properties of CO2can be easily controlled by adjusting pressure and temperature parameters. Owing to its low viscosity and high diffusivity, SCO2can penetrate materials more effectively compared to liquid solvents. High diffusivity enhances mass transfer, and together with the low surface tension of the fluid, allows easy penetration into the structures to be extracted. Furthermore, as the mass transfer rate increases, the overall processing time is significantly reduced.
[0013] The supercritical fluid extraction method used in the present invention provides the following advantages:
[0014] - It enables the extraction of omega-5 fatty acids with high efficiency. Compared to conventional extraction methods, a higher oil yield is obtained, providing significant economic benefits to manufacturers.
[0015] - As the process is carried out under low temperature and high pressure conditions, the quality of the omega-5 fatty acid is preserved. Accordingly, the omega-5 fatty acid obtained by this method is characterized by a low acid value, low peroxide value, high active compound content, and high nutritional value. - Since carbon dioxide is used as the solvent, the method is environmentally friendly. Consequently, it reduces environmental pollution and contributes to environmental sustainability.
[0016] - It facilitates the management of waste generated during the processing of oilseeds and their pomace. The pomace remaining after extraction, due to its high fiber content, may be used as an animal feed additive, may be utilized as plant-based protein for human consumption, or may be evaluated in biogas production. This enables the recycling of waste materials and reduces waste management costs.- The processed oilseeds and their pomace can provide economic and national benefits.
[0017] In terms of yield, omega-5 fatty acids remain within the pomace in extraction processes carried out using conventional methods due to low efficiency. In the present invention, nearly 99% yield of omega-5 fatty acid is obtained from pomegranate seeds by means of supercritical carbon dioxide extraction.
[0018] LIST OF FIGURES
[0019] Figure 1. General View of the System
[0020] Correspondences of the Numbers Shown in the Figures
[0021] 1. Extractor
[0022] 2. Separator
[0023] 3. Extract
[0024] 4. Liquid CO2
[0025] 5. Cooler
[0026] 6. High-pressure pump
[0027] 7. Heater
[0028] DETAILED DESCRIPTION OF THE INVENTION
[0029] In the present invention, carbon dioxide is used as the solvent during the purification of punicic acid (omega-5 fatty acid) from pomegranate seeds by means of supercritical fluid extraction. The carbon dioxide used is maintained under pressure during a static holding (static soaking) period, during which it acquires supercritical properties at a temperature of at least 31.1 °C and a pressure of at least 73.8 bar for a minimum duration of 30 minutes.
[0030] Dynamic flow, referred to as “sweeping,” is carried out for a minimum period of 6.5 hours, depending on the amount and particle size of the ground oilseed. During dynamic flow, carbon dioxide is continuously passed through the product to dissolve the oil, and the oil-laden supercritical carbon dioxide is transferred to the separators (2). In the separators (2), due to the lower pressure, carbon dioxide transitions to the gaseous phase and releases the oil product into the separator (2). The carbon dioxidethat has entered the gas phase is subsequently condensed and returned to the liquid carbon dioxide tank. As this system is regenerative, carbon dioxide consumption is minimal. Therefore, since generally low temperatures are employed during supercritical CO2extraction, adverse effects commonly encountered in high-temperature extraction methods — such as increased peroxide values, elevated free fatty acid content, material loss, and / or the occurrence of undesirable thermal reactions do not arise.
[0031] Production Method of the Invention:
[0032] - After the pomegranate seeds are crushed and ground to a particle size of 0.5 mm, they are loaded into the supercritical fluid system using baskets.
[0033] - Filters with a pore size of 100 microns, which prevent the passage of pomace while allowing oil to pass through, are positioned above and below the baskets. - These baskets are placed into the extractors (1).
[0034] - The temperature set values (target temperatures) of the extractors (1) and separators (2) are entered. The temperature set range for the extractors (1 ) and separators (2) is 45-60 °C. At this stage, it is not necessary to wait for the system to reach the set temperature, as the temperature will increase with rising pressure and the system will reach equilibrium.
[0035] - The extractors (1) are pressurized with carbon dioxide to at least 73.8 bar. - The carbon dioxide heated in the heater (7) reaches the supercritical point and enters the extractor (1).
[0036] - Since carbon dioxide is an apolar substance, it acts as an excellent oil solvent at the supercritical point. Depending on the bioactive components contained in the raw material, up to 7% food-grade ethanol may optionally be used as a cosolvent to enhance solubility.
[0037] - Following the completion of the static holding and dynamic flow steps (after at least 7 hours), the fatty acid product is collected from the separator (2).
[0038] - If food-grade ethanol is used (optional), ethanol is recovered together with high- purity punicic acid from the separator and is subsequently removed by molecular distillation.
[0039] - Prior to filling, quality control tests are performed on the produced oil. These tests include determination of free fatty acid percentage, oil composition analysis, peroxide value analysis, total phenolic content determination, total antioxidant capacity determination, and acid value determination.The Rancimat test is used to determine the shelf life of the punicic acid-rich oil.
[0040] As a result of these tests, the quality parameters are determined. The punisic acid (omega-5 fatty acid) content in the pomegranate seed oil composition obtained by supercritical fluid extraction has been determined to be in the range of 80%-87%.
Claims
CLAIMS1. A fatty acid obtained from pomegranate seeds by using supercritical fluid extraction, characterized by; comprises punicic acid (omega-5 fatty acid) in an amount ranging from 80% to 87%.
2. A method for producing punicic acid (omega-5 fatty acid) from pomegranate seeds by using supercritical fluid extraction, characterized by;- loading into baskets after crushing the pomegranate and grinding to 0.5 mm- placement of 100 pm filters above and below the baskets,- placing the baskets into extractors (1 ),- setting the temperature set values of the extractors (1) and separators (2),- pressurizing the extractors (1) with carbon dioxide to at least 73.8 bar, - entering the extractor (1 ) reached the supercritical point of carbon dioxide heating in the heater (7)- collecting the oil product from the separator (2) after completion of static holding and dynamic flow steps,- obtained of high-purity punicic acid from the separator (2).