EP4036197A1 - Procédé d'affinage de pâte de neutralisation par acidulation et extraction de solvant - Google Patents

Procédé d'affinage de pâte de neutralisation par acidulation et extraction de solvant Download PDF

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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
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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
Application number
EP22153446.4A
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German (de)
English (en)
Inventor
Valdis Kampars
R ta Kampare
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rigas Tehniska Univ
Rigas Tehniska Universitate
Original Assignee
Rigas Tehniska Univ
Rigas Tehniska Universitate
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Rigas Tehniska Univ, Rigas Tehniska Universitate filed Critical Rigas Tehniska Univ
Priority to EP22153446.4A priority Critical patent/EP4036197A1/fr
Publication of EP4036197A1 publication Critical patent/EP4036197A1/fr
Pending legal-status Critical Current

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    • 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.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Fats And Perfumes (AREA)
EP22153446.4A 2022-01-26 2022-01-26 Procédé d'affinage de pâte de neutralisation par acidulation et extraction de solvant Pending EP4036197A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP22153446.4A EP4036197A1 (fr) 2022-01-26 2022-01-26 Procédé d'affinage de pâte de neutralisation par acidulation et extraction de solvant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP22153446.4A EP4036197A1 (fr) 2022-01-26 2022-01-26 Procédé d'affinage de pâte de neutralisation par acidulation et extraction de solvant

Publications (1)

Publication Number Publication Date
EP4036197A1 true EP4036197A1 (fr) 2022-08-03

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EP (1) EP4036197A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
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 (fr) 2004-11-09 2007-07-25 Cognis IP Management GmbH Production de biodiesel a partir de soapstock
CN113717796A (zh) * 2021-08-20 2021-11-30 南京林业大学 一种超声波辅助皂脚加压水解一步转化脂肪酸的方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
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 (fr) 2004-11-09 2007-07-25 Cognis IP Management GmbH Production de biodiesel a partir de soapstock
EP1809755B1 (fr) 2004-11-09 2009-07-08 Cognis IP Management GmbH Production de biodiesel a partir de soapstock
CN113717796A (zh) * 2021-08-20 2021-11-30 南京林业大学 一种超声波辅助皂脚加压水解一步转化脂肪酸的方法

Non-Patent Citations (12)

* Cited by examiner, † Cited by third party
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>

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