EP4036197A1 - Method for refining of soapstock by acidulation and solvent extraction - Google Patents
Method for refining of soapstock by acidulation and solvent extraction Download PDFInfo
- Publication number
- EP4036197A1 EP4036197A1 EP22153446.4A EP22153446A EP4036197A1 EP 4036197 A1 EP4036197 A1 EP 4036197A1 EP 22153446 A EP22153446 A EP 22153446A EP 4036197 A1 EP4036197 A1 EP 4036197A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- mixture
- obtaining
- oil
- soapstock
- biodiesel
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
- C11B13/02—Recovery of fats, fatty oils or fatty acids from waste materials from soap stock
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/025—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by saponification and release of fatty acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
- C11C1/10—Refining by distillation
- C11C1/103—Refining by distillation after or with the addition of chemicals
Definitions
- the invention relates to the vegetable oil refining and energy sector, in particular to the production of a raw material for the industrial manufacturing of advanced biodiesel from the residue of vegetable oil refining process, called a soapstock (SS), which is obtained after washing the crude oil with aqueous alkaline solution.
- a soapstock SS
- Fossil fuels in the form of LPG, petrol, diesel, and jet fuels continue to dominate the transportation sector, exerting catastrophic effect on the environment and facilitate the climate change.
- the replacement of fossil fuels in the transport sector is particularly relevant.
- a waste material containing free fatty acids (FFA) and mono-, di- and triglycerides (MDTG) acid oil (AO) leads to a high interest in the production of all commodities containing fatty acid moiety, including biodiesel.
- As the production of biofuels from food materials (conventional biofuels) is planned to be limited to 7%, ensuring the prognosticate increase in the total share of biofuels becomes a rather difficult challenge. Significance of low-quality feedstock, including AO, increases [2].
- AO is obtained by acidulation of soapstock (SS) by adding an acid and lowering the pH of the mixture to around 2-3 so as to fully convert the soap into FFA [4].
- SS is generated at almost 6% of the volume of the crude oil production amounts, and is classified as both a waste and a low quality by-product which costs significantly less than vegetable oil, therefore it can be considered as a raw material for synthesis of advanced biodiesel.
- SS contains a high amount of water, which is emulsified with lipid components, such as acylglycerols, FFA, salts (soap), and other components (phosphoacylglycerols, tocopherols, sterols, and pigments) from crude oil.
- lipid components such as acylglycerols, FFA, salts (soap), and other components (phosphoacylglycerols, tocopherols, sterols, and pigments
- lipid components such as acylglycerols, FFA, salts (soap), and other components (phosphoacylglycerols, tocopherols, sterols, and pigments) from crude oil.
- phosphoacylglycerols such as acylglycerols, FFA, salts (soap)
- phosphoacylglycerols, tocopherols, sterols, and pigments from crude oil.
- the disadvantage of this method is the low yield of the required products. More often, however, acidulation and extraction are carried out as two separate processes.
- the method makes it possible to dry the substrate before the extraction, which significantly increase the extraction yield [10].
- fat well-dissolving solvent as hexane [10] is used, but for isolation of fatty components also isopropyl alcohol, toluene, fusel oil, and a mixture of common salt and non-ionic surfactants [11] were used.
- the extraction temperature is around 60 °C [10] and the extraction time is 2 to 12 h. Ultrasound environment increases the extraction yield from dry substrate [10].
- Pure extracts can be prepared by consecutive extraction method using few organic solvents [12], but it substantially lowers the yield of products and is not acceptable for industrial purpose. Soxhlet extraction with hexane taking more than 6 h is often successfully performed [13,14] and can be considered as a standard extraction method. Its main disadvantage is longevity of the process and energy consumption [15].
- EP 1809755 B1 applies to a compact and more environmentally friendly fatty acid esterification production process to make alkyl and mainly methyl and ethyl esters starting directly from SS waste.
- the benefit of this process is the use of enzymes as esterification catalysts able to convert the FFA into esters in the presence of water, salts, soaps, and many other impurities. As the process should be carried out from a contaminated environment, the enzymatic process is expensive and inefficient.
- SS is an emulsion of complex organic and inorganic substances in water, a mixture of monoglycerides (MG), diglycerides (DG), triglycerides (TG) and free fatty acids (FFA).
- Feedstock for biodiesel called acid oil (AO) must first be obtained from SS.
- MDTG and FFA are the raw material for obtaining advanced biodiesel and AO can be used for its synthesis.
- a new and efficient method for obtaining AO from SS with good yield and high quality is proposed. The proposed method is based on acidulation and extraction of SS in ultrasound environment in a fast and energy consuming process.
- the objective of the invention is to change the acidification of soapstock (SS) and extraction of acid oil (AO) in such a way that it takes place within a maximum of 2-3 h, excluding the dehydration and drying of the intermediate and ensuring a high yield and quality of AO.
- the goal is achieved by the invented method, which comprises following steps:
- Another aspect of the invention is an acid oil, obtained by the method according to the invention and use of this acid oil in advanced biodiesel synthesis.
- Figure 1 shows production of advanced biodiesel, comparing the invention and industrial methods, which shows both the formation of SS in the oil refining process and its use in the production of advanced biodiesel.
- the production of AO by the invented acidification-extraction method provides a significantly higher yield of AO from SS than the previously known methods and is feasible in a shorter time with lower energy consumption.
- the invention is applicable to the industrial production of advanced biodiesel from SS, which is generally considered as waste and cannot be used for food production.
- SS is transformed from waste into a feedstock for the production of the advanced biodiesel.
- the use of SS will expand the feedstock base for advanced biodiesel production and promote the production of fuel from non-food feedstocks.
Abstract
Description
- The invention relates to the vegetable oil refining and energy sector, in particular to the production of a raw material for the industrial manufacturing of advanced biodiesel from the residue of vegetable oil refining process, called a soapstock (SS), which is obtained after washing the crude oil with aqueous alkaline solution.
- Fossil fuels in the form of LPG, petrol, diesel, and jet fuels continue to dominate the transportation sector, exerting catastrophic effect on the environment and facilitate the climate change. The replacement of fossil fuels in the transport sector is particularly relevant. As a waste material containing free fatty acids (FFA) and mono-, di- and triglycerides (MDTG) acid oil (AO) leads to a high interest in the production of all commodities containing fatty acid moiety, including biodiesel. As the production of biofuels from food materials (conventional biofuels) is planned to be limited to 7%, ensuring the prognosticate increase in the total share of biofuels becomes a rather difficult challenge. Significance of low-quality feedstock, including AO, increases [2].
- AO is obtained by acidulation of soapstock (SS) by adding an acid and lowering the pH of the mixture to around 2-3 so as to fully convert the soap into FFA [4]. SS is generated at almost 6% of the volume of the crude oil production amounts, and is classified as both a waste and a low quality by-product which costs significantly less than vegetable oil, therefore it can be considered as a raw material for synthesis of advanced biodiesel.
- SS contains a high amount of water, which is emulsified with lipid components, such as acylglycerols, FFA, salts (soap), and other components (phosphoacylglycerols, tocopherols, sterols, and pigments) from crude oil. It is known that the acidulation of SS is always carried out simultaneously with at least of partial hydrolysis of glycerides in the presence of phosphoric, hydrochloric, or sulfuric acid [4, 5]. The reaction temperature usually does not exceed 90 °C and the reaction time is about 1 h [4].
- Wang et al describes recovery technology of acid oil (AO) from SS with only sulfuric acid solution addition under the ambient temperature (25±2 °C) [6]. After drying, AO contained 50.0% FFA, 15.5% TG, 6.9% DG, 3.1% MG, 0.8% water, and other inert materials. The recovery yield of AO was about 97% (w/w) based on the total fatty acids of the SS.
- Systematic studies of acidulation at room temperature, as well as the results of literature [7], showed that acidulation alone does not provide a quality feedstock for biodiesel synthesis and requires an additional purification process. This process can be extraction with organic solvent. Acidulation and extraction with organic solvent can be performed in one step [8, 9].
- The disadvantage of this method is the low yield of the required products. More often, however, acidulation and extraction are carried out as two separate processes. The method makes it possible to dry the substrate before the extraction, which significantly increase the extraction yield [10]. Usually such fat well-dissolving solvent as hexane [10] is used, but for isolation of fatty components also isopropyl alcohol, toluene, fusel oil, and a mixture of common salt and non-ionic surfactants [11] were used. The extraction temperature is around 60 °C [10] and the extraction time is 2 to 12 h. Ultrasound environment increases the extraction yield from dry substrate [10].
- Pure extracts can be prepared by consecutive extraction method using few organic solvents [12], but it substantially lowers the yield of products and is not acceptable for industrial purpose. Soxhlet extraction with hexane taking more than 6 h is often successfully performed [13,14] and can be considered as a standard extraction method. Its main disadvantage is longevity of the process and energy consumption [15].
- Other processes are offered in
patent application US3965085A and patentEP 1809755 B1 . According to theUS3965085A , the extraction is carried out with water-immiscible solvents (hexane, heptane, benzene and light petroleum) from a previously prepared mixture obtained by adding a low-molecule ketone (acetone) to the raw material and then carrying out the extraction. The result is a water-acetone phase containing fatty acids and fatty acid-containing saponifiable products and an organic phase. The disadvantage of the method is the use of at least 2 solvents (acetone and a water-immiscible solvent) that need to be recovered and the long duration of the process. The production of raw materials suitable for the synthesis of biofuels does not take place directly, but by trying to remove the impurities with the help of acetone-water solution. Acetone recovery is problematic and the yield is not high. -
EP 1809755 B1 applies to a compact and more environmentally friendly fatty acid esterification production process to make alkyl and mainly methyl and ethyl esters starting directly from SS waste. The benefit of this process is the use of enzymes as esterification catalysts able to convert the FFA into esters in the presence of water, salts, soaps, and many other impurities. As the process should be carried out from a contaminated environment, the enzymatic process is expensive and inefficient. - SS is an emulsion of complex organic and inorganic substances in water, a mixture of monoglycerides (MG), diglycerides (DG), triglycerides (TG) and free fatty acids (FFA). Feedstock for biodiesel called acid oil (AO), must first be obtained from SS. MDTG and FFA are the raw material for obtaining advanced biodiesel and AO can be used for its synthesis. In this invention, a new and efficient method for obtaining AO from SS with good yield and high quality is proposed. The proposed method is based on acidulation and extraction of SS in ultrasound environment in a fast and energy consuming process.
- The objective of the invention is to change the acidification of soapstock (SS) and extraction of acid oil (AO) in such a way that it takes place within a maximum of 2-3 h, excluding the dehydration and drying of the intermediate and ensuring a high yield and quality of AO.
- The goal is achieved by the invented method, which comprises following steps:
- a) providing soapstock of vegetable oil refining process;
- b) acidulation of the soapstock of step (a) with phosphoric acid in amount which provides reduction of the pH of said soapstock to pH 2-3, obtaining a mixture (i);
- c) heating the mixture (i) from step (b) in an ultrasonic environment at a temperature 95-97 °C for 15-45 min, obtaining mixture (ii);
- d) cooling of the mixture of step (c) to room temperature;
- e) extraction of mixture of step (d) at room temperature in an ultrasonic environment for 25-45 min by adding a quantity of cyclohexane in ml that is equal or exceeds 1.5-fold the mass in g of the mixture (ii), obtaining mixture (iii);
- f) centrifugation of the mixture (iii) of step (e), obtaining a liquid mixture (iv);
- g) obtaining of an oil layer and a water layer by settling of the mixture (iv) of step (f)
- h) separating the oil layer of step (g);
- i) obtaining an acid oil by distilling cyclohexane from the oil layer of step (h).
- Significant simplification has been made in the extraction process with cyclohexane. The extraction process takes place in an ultrasonic environment, without prior separation of the water layer. Such extraction without ultrasound would lead to a significant (30-50%) reduction in the yield of AO, but in the ultrasonic environment the opposite effect is observed, therefore it is possible to simplify the extraction process. The extraction with cyclohexane in an ultrasonic medium takes place at the same time as rinsing the raw material with the water contained in the SS. As a result, the AO's output increases and its quality improves.
- Another aspect of the invention is an acid oil, obtained by the method according to the invention and use of this acid oil in advanced biodiesel synthesis.
-
Figure 1 shows production of advanced biodiesel, comparing the invention and industrial methods, which shows both the formation of SS in the oil refining process and its use in the production of advanced biodiesel. - The invention is described but not limited by the following examples.
- According to the preffered embodiment obtaining an acid oil comprises following steps:
- a) providing 40 g soapstock of vegetable oil refining process;
- b) acidulation of the soapstock of step (a) with phosphoric acid in amount which provides reduction of the pH of said soapstock to pH 2-3, obtaining a mixture (i);
- c) heating the mixture (i) from step (b) in an ultrasonic environment at a temperature 95 °C for 30 min, obtaining mixture (ii);
- d) cooling of the mixture of step (c) to room temperature;
- e) extraction of mixture of step (d) at room temperature in an ultrasonic environment for 30 min by adding 60 ml of cyclohexane without water removing, obtaining mixture (iii);
- f) centrifugation of the mixture (iii) of step (e), obtaining a liquid mixture (iv);
- g) obtaining of an oil layer and a water layer by settling of the mixture (iv) of step (f) and
- h) separating the oil layer of step (g);
- i) obtaining an acid oil by distilling cyclohexane from the oil layer of step (h).
- The second embodiment obtaining an acid oil comprises following steps:
- a) providing 40 g soapstock of vegetable oil refining process;
- b) acidulation of the soapstock of step (a) with phosphoric acid in amount which provides reduction of the pH of said soapstock to pH 2-3, obtaining a mixture (i);
- c) heating the mixture (i) from step (b) in an ultrasonic environment at a temperature 95 °C for 15 min, obtaining mixture (ii);
- d) cooling of the mixture of step (c) to room temperature;
- e) extraction of mixture of step (d) at room temperature in an ultrasonic environment for 25 min by adding 40 ml of cyclohexane without water removing, obtaining mixture (iii);
- f) centrifugation of the mixture (iii) of step (e), obtaining a liquid mixture (iv);
- g) obtaining of an oil layer and a water layer by settling of the mixture (iv) of step (f) and
- h) separating the oil layer of step (g);
- i) obtaining an acid oil by distilling cyclohexane from the oil layer of step (h).
- The third embodiment obtaining an acid oil comprises following steps:
- a) providing 40 g soapstock of vegetable oil refining process;
- b) acidulation of the soapstock of step (a) with phosphoric acid in amount which provides reduction of the pH of said soapstock to pH 2-3, obtaining a mixture (i);
- c) heating the mixture (i) from step (b) in an ultrasonic environment at a temperature 97 °C for 30 min, obtaining mixture (ii);
- d) cooling of the mixture of step (c) to room temperature;
- e) extraction of mixture of step (d) at room temperature in an ultrasonic environment for 30 min by adding 40 ml of cyclohexane without water removing, obtaining mixture (iii);
- f) centrifugation of the mixture (iii) of step (e), obtaining a liquid mixture (iv);
- g) obtaining of an oil layer and a water layer by settling of the mixture (iv) of step (f) and
- h) separating the oil layer of step (g);
- i) obtaining an acid oil by distilling cyclohexane from the oil layer of step (h).
- The fourth embodiment obtaining an acid oil comprises following steps:
- a) providing 40 g soapstock of vegetable oil refining process;
- b) acidulation of the soapstock of step (a) with phosphoric acid in amount which provides reduction of the pH of said soapstock to pH 2-3, obtaining a mixture (i);
- c) heating the mixture (i) from step (b) in an ultrasonic environment at a temperature 95 °C for 45 min, obtaining mixture (ii);
- d) cooling of the mixture of step (c) to room temperature;
- e) extraction of mixture of step (d) at room temperature in an ultrasonic environment for 30 min by adding 40 ml of cyclohexane without water removing, obtaining mixture (iii);
- f) centrifugation of the mixture (iii) of step (e), obtaining a liquid mixture (iv);
- g) obtaining of an oil layer and a water layer by settling of the mixture (iv) of step (f) and
- h) separating the oil layer of step (g);
- i) obtaining an acid oil by distilling cyclohexane from the oil layer of step (h).
- The fifth embodiment obtaining an acid oil comprises following steps:
- a) providing 40 g soapstock of vegetable oil refining process;
- b) acidulation of the soapstock of step (a) with phosphoric acid in amount which provides reduction of the pH of said soapstock to pH 2-3, obtaining a mixture (i);
- c) heating the mixture (i) from step (b) in an ultrasonic environment at a temperature 95 °C for 30 min, obtaining mixture (ii);
- d) cooling of the mixture of step (c) to room temperature;
- e) extraction of mixture of step (d) at room temperature in an ultrasonic environment for 45 min by adding 40 ml of cyclohexane without water removing, obtaining mixture (iii);
- f) centrifugation of the mixture (iii) of step (e), obtaining a liquid mixture (iv);
- g) obtaining of an oil layer and a water layer by settling of the mixture (iv) of step (f) and
- h) separating the oil layer of step (g);
- i) obtaining an acid oil by distilling cyclohexane from the oil layer of step (h).
- The production of AO by the invented acidification-extraction method provides a significantly higher yield of AO from SS than the previously known methods and is feasible in a shorter time with lower energy consumption.
- The invention is applicable to the industrial production of advanced biodiesel from SS, which is generally considered as waste and cannot be used for food production. As a result of the use of the method, SS is transformed from waste into a feedstock for the production of the advanced biodiesel. The use of SS will expand the feedstock base for advanced biodiesel production and promote the production of fuel from non-food feedstocks.
-
- [1] Eurostat Statistics Explained - Europa EU, 2020. https://ec.europa.eu/eurostat/statistics-explained/index.php
- [2] Directive (EU) 2018/2001, PE/48/2018/REV/1
- [3] EU Biofuels Annual 2020,https://www.fas.usda.gov/data/9eaction-union-biofuels-annual-0
- [4] Michael J. Haas, Improving the economics of biodiesel production through the use of low value lipids as feedstocks: vegetable oil soapstock. Fuel Processing Technology, 86(2005), 1087-1096. 10.1016/j.fuproc.2004.11.004
- [5] M. M. Ostafin et al. Recovering of the long-chain fatty acids from soapstock, PRZEMYSL CHEMICZNY. 2018-3. DOI:10.15199/62.2018.3.9
- [6] Z.M.Wang, J.S. Lee, J.Y. Park, Z.H.Yuan. Novel biodiesel production from soybean soapstock. Korean J. Chem. Eng. 24(2007), 1027-1030. https://doi.org/10.1007/s11814-007-0115-6
- [7] C. Echim, R.Verhe, W. De Grey, C. Stevens. Production of biodiesel from sidestream refining products. Energy Environ. Sci., 2(2009), 1131-1141. https://doi.org/10.1039/B905925C
- [8]
US20010049452A1 - Method for soapstock acidulation. - [9] C. Nakyung, J.S. Lee, J. Kwak, J. Lee, I.H. Kim. Production of Biodiesel from Acid Oil via a Two-Step Enzymatic Transesterification, J. Oleo Sci. 65 (2016), 913-921. doi:10.5650/jos.ess16092
- [10] B. H. Goh, H. C. Ong, C. T. Chong, W. Chen, K. Y. Leong, S. X. Tan, X. J. Lee. Ultrasonic assisted oil extraction and biodiesel synthesis of Spent Coffee Ground. Fuel 261 (2020) 116121 https://doi.org/10.1016/j.fuel.2019.116121
- [11] Y.I. Prokof'ev, T. N. Poyarkova, A. R. Bykov, A. S. Shestakov, V. A. Kuznetsov, O.G. Androsova. Influence of the isolation method of the soapstock fatty component on its characteristics. Res. Agr. Eng., 61 (2015), 111-115. doi: 10.17221/20/2014-RAE
- [12]_H. Nawaz, M. A. Shad, N. Rehman, H. Andaleeb, N. Ullah. Effect of solvent polarity on extraction yield and antioxidant properties of phytochemicals from bean (Phaseolus vulgaris) seeds. Braz. J. Pharm. Sci., 56 (2020) ISSN 2175-9790 https://doi.org/10.1590/s2175-97902019000417129
- [13] M. Cruz, E. Costa, M. F. Almeida, M. da Conceicao Alvim-Ferraz, J. M. Dias. Recovery of by-products from the olive oil production and the vegetable oil refining for biodiesel production. Detritus, 4 (2018), DOI:10.31025/2611-4135/2018.13728
- [14] I. Efthymiopoulos, P. Hellier, N. Ladommatos, A. Kay, B. Mills-Lamptey. Integrated strategies for water removal and lipid extraction from coffee industry residues. Sustainable Energy Technologies and Assessments 29 (2018) 26-35 https://doi.org/10.1016/j.seta.2018.06.016
- [15] Al Juhaimi F, Ozcan MM, Ghafoor K, Babiker EE, Hussain S. Comparison of cold-pressing and soxhlet extraction systems for bioactive compounds, antioxidant properties, polyphenols, fatty acids and tocopherols in eight nut oils. J Food Sci Technol. 55 (2018), 3163-3173. doi:10.1007/s13197-018-3244-5
-
-
Claims (5)
- A method of obtaining an acid oil wherein the method comprises following steps:a) providing soapstock of vegetable oil refining process;b) acidulation of the soapstock of step (a) with phosphoric acid in amount which provides reduction of the pH of said soapstock to pH 2-3, obtaining a mixture (i);c) heating the mixture (i) from step (b) in an ultrasonic environment at a temperature 95-97 °C for 15-45 min, obtaining mixture (ii);d) cooling of the mixture of step (c) to room temperature;e) extraction of mixture of step (d) at room temperature in an ultrasonic environment for 25-45 min by adding a quantity of cyclohexane in ml that is equal or exceeds 1.5-fold the mass in g of the mixture (ii), obtaining mixture (iii);f) centrifugation of the mixture (iii) of step (e), obtaining a liquid mixture (iv);g) obtaining of an oil layer and a water layer by settling of the mixture (iv) of step (f)h) separating the oil layer of step (g);i) obtaining an acid oil by distilling cyclohexane from the oil layer of step (h).
- The method according to claim 1, wherein the mixture (i) from step (b) is heated in an ultrasonic environment at a 95 °C for 30 min.
- The method according to claim 1 or 2, wherein the extraction of step (e) is carried out for 30 min.
- An acid oil, obtained by the method according to any of claims 1 to 3.
- Use of the acid oil according to claim 4 in advanced biodiesel synthesis.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP22153446.4A EP4036197A1 (en) | 2022-01-26 | 2022-01-26 | Method for refining of soapstock by acidulation and solvent extraction |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP22153446.4A EP4036197A1 (en) | 2022-01-26 | 2022-01-26 | Method for refining of soapstock by acidulation and solvent extraction |
Publications (1)
Publication Number | Publication Date |
---|---|
EP4036197A1 true EP4036197A1 (en) | 2022-08-03 |
Family
ID=80035187
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP22153446.4A Pending EP4036197A1 (en) | 2022-01-26 | 2022-01-26 | Method for refining of soapstock by acidulation and solvent extraction |
Country Status (1)
Country | Link |
---|---|
EP (1) | EP4036197A1 (en) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3428660A (en) * | 1964-01-20 | 1969-02-18 | Baker Perkins Inc | Process for recovering fatty acids and triglyceride oil from soapstock |
US3965085A (en) | 1973-06-29 | 1976-06-22 | Bjarne Holmbom | Method for refining of soaps using solvent extraction |
US20010049452A1 (en) | 2000-03-24 | 2001-12-06 | Reaney Martin J. | Method for soapstock acidulation |
US20030186818A1 (en) * | 2002-03-26 | 2003-10-02 | Reaney Martin J. T. | Oil soluble photoprotective compounds and compositions from plant oil processing |
EP1809755A1 (en) | 2004-11-09 | 2007-07-25 | Cognis IP Management GmbH | Biodiesel production from soapstock |
CN113717796A (en) * | 2021-08-20 | 2021-11-30 | 南京林业大学 | Method for converting fatty acid in one step by ultrasonic-assisted pressure hydrolysis of soapstock |
-
2022
- 2022-01-26 EP EP22153446.4A patent/EP4036197A1/en active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3428660A (en) * | 1964-01-20 | 1969-02-18 | Baker Perkins Inc | Process for recovering fatty acids and triglyceride oil from soapstock |
US3965085A (en) | 1973-06-29 | 1976-06-22 | Bjarne Holmbom | Method for refining of soaps using solvent extraction |
US20010049452A1 (en) | 2000-03-24 | 2001-12-06 | Reaney Martin J. | Method for soapstock acidulation |
US20030186818A1 (en) * | 2002-03-26 | 2003-10-02 | Reaney Martin J. T. | Oil soluble photoprotective compounds and compositions from plant oil processing |
EP1809755A1 (en) | 2004-11-09 | 2007-07-25 | Cognis IP Management GmbH | Biodiesel production from soapstock |
EP1809755B1 (en) | 2004-11-09 | 2009-07-08 | Cognis IP Management GmbH | Biodiesel production from soapstock |
CN113717796A (en) * | 2021-08-20 | 2021-11-30 | 南京林业大学 | Method for converting fatty acid in one step by ultrasonic-assisted pressure hydrolysis of soapstock |
Non-Patent Citations (12)
Title |
---|
A1 JUHAIMI FOZCAN MMGHAFOOR KBABIKER EEHUSSAIN S: "Comparison of cold-pressing and soxhlet extraction systems for bioactive compounds, antioxidant properties, polyphenols, fatty acids and tocopherols in eight nut oils", J FOOD SCI TECHNOL, vol. 55, 2018, pages 3163 - 3173, XP036547849, DOI: 10.1007/s13197-018-3244-5 |
B. H. GOHH. C. ONGC. T. CHONGW. CHENK. Y. LEONGS. X. TANX. J. LEE: "Ultrasonic assisted oil extraction and biodiesel synthesis of Spent Coffee Ground", FUEL, vol. 261, 2020, pages 116121, Retrieved from the Internet <URL:https://doi.ors/10.1016/i.fuel.2019.116121> |
C. ECHIMR.VERHEW. DE GREYC. STEVENS: "Production of biodiesel from sidestream refining products", ENERGY ENVIRON. SCI., vol. 2, 2009, pages 1131 - 1141, Retrieved from the Internet <URL:https://doi.ors/10.1039/B905925C> |
C. NAKYUNGJ.S. LEEJ. KWAKJ. LEEI.H. KIM: "Production of Biodiesel from Acid Oil via a Two-Step Enzymatic Transesterification", J. OLEO SCI., vol. 65, 2016, pages 913 - 921 |
H. NAWAZM. A. SHADN. REHMANH. ANDALEEBN. ULLAH: "Effect of solvent polarity on extraction yield and antioxidant properties of phytochemicals from bean (Phaseolus vulgaris) seeds. Braz", J. PHARM. SCI., vol. 56, 2020, Retrieved from the Internet <URL:https://doi.org/10.1590/s2175-97902019000417129> |
I. EFTHYMIOPOULOSP. HELLIERN. LADOMMATOSA. KAYB. MILLS-LAMPTEY: "Integrated strategies for water removal and lipid extraction from coffee industry residues", SUSTAINABLE ENERGY TECHNOLOGIES AND ASSESSMENTS, vol. 29, 2018, pages 26 - 35, Retrieved from the Internet <URL:https://doi.ors/10.1016/i.seta.2018.06.016> |
M. CRUZE. COSTAM. F. ALMEIDAM. DA CONCEICAO ALVIM-FERRAZJ. M. DIAS: "Recovery of by-products from the olive oil production and the vegetable oil refining for biodiesel production", DETRITUS, vol. 4, 2018 |
M. M. OSTAFIN ET AL.: "Recovering of the long-chain fatty acids from soapstock", PRZEMYSL CHEMICZNY, 2018 |
MICHAEL J. HAAS: "Improving the economics of biodiesel production through the use of low value lipids as feedstocks: vegetable oil soapstock", FUEL PROCESSING TECHNOLOGY, vol. 86, 2005, pages 1087 - 1096 |
SHAO P ET AL: "Process optimisation for the production of biodiesel from rapeseed soapstock by a novel method of short path distillation", BIOSYSTEMS ENGINEERING, ELSEVIER, AMSTERDAM, NL, vol. 102, no. 3, 1 March 2009 (2009-03-01), pages 285 - 290, XP025952054, ISSN: 1537-5110, [retrieved on 20090106], DOI: 10.1016/J.BIOSYSTEMSENG.2008.11.014 * |
Y.I. PROKOFEVT. N. POYARKOVAA. R. BYKOVA. S. SHESTAKOVV. A. KUZNETSOVO.G. ANDROSOVA: "Influence of the isolation method of the soapstock fatty component on its characteristics", RES. AGR. ENG., vol. 61, 2015, pages 111 - 115 |
Z.M.WANGJ.S. LEEJ.Y. PARKZ.H.YUAN: "Novel biodiesel production from soybean soapstock", KOREAN J. CHEM. ENG., vol. 24, 2007, pages 1027 - 1030, Retrieved from the Internet <URL:https:Hdoi.org/10.1007/s11814-007-0115-6> |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2114851B1 (en) | Process for separating saturated and unsaturated fatty acids | |
Boey et al. | Ultrasound aided in situ transesterification of crude palm oil adsorbed on spent bleaching clay | |
JP6316590B2 (en) | Refined vegetable oil and method for producing the same | |
EP1894913A1 (en) | Production of esters of fatty acids and lower alcohols | |
EP3010995B1 (en) | Process for producing biodiesel and related products | |
WO2011012440A3 (en) | A process for the production of bio-naphtha from complex mixtures of natural occurring fats & oils | |
EP2038389B1 (en) | Process for production of fatty acids, fatty acid esters and sterolesters from soapstock | |
US20170107452A1 (en) | Products Produced From Distillers Corn Oil | |
US20080015367A1 (en) | Process for isolating phytosterols and tocopherols from deodorizer distillate | |
Díaz-Suárez et al. | Aqueous enzymatic extraction of Ricinus communis seeds oil using Viscozyme L | |
WO2002046339A3 (en) | Method for pretreating crude oils and raw fats for the production of fatty acid esters | |
CN111315855A (en) | Improved method for extracting cholesterol from fish oil waste residue | |
CN101056985B (en) | Soapstock biodiesel | |
WO2015106186A2 (en) | Compositions of cosmetic, personal care and skin care products derived from lipid feedstocks and methods to produce the same | |
EP4036197A1 (en) | Method for refining of soapstock by acidulation and solvent extraction | |
EP1644469B1 (en) | Process for preparing purified fatty acids | |
AU2020254063A1 (en) | Fish oil cholesterol | |
US20080287697A1 (en) | Process for preparing fatty acid esters from pre-treated glyceride oils | |
CN103588855B (en) | A kind of method of plant sterol of purifying from deodorization distillate | |
EP3245277B1 (en) | Recovery of tocopherols/tocotrienols, carotenoids, glycerols, sterols and fatty acid esters from crude vegetable oil and the process thereof | |
JP4645997B2 (en) | Method for recovering unsaponifiable matter from tall oil pitch and method for producing sterols | |
US20150344797A1 (en) | Fatty acid reduction of feedstock and neutral and acidic alkyl ester | |
RU2676485C1 (en) | Method of obtaining biodiesel fuel in medium of supercritical dimethyl carbonate | |
Thorat et al. | Production of Fatty Acid Methyl Ester from Acid Oil an Edible Oil Refinery By-Product by Two Step Esterification Followed by Trans-Esterification Process | |
EP4223860A1 (en) | Method for obtaining cholesterol present in fish oil |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN PUBLISHED |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 20220803 |
|
RBV | Designated contracting states (corrected) |
Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |