WO2015184629A1 - Procédé de rupture de parois de microalgues et d'extraction d'huile tout en estérifiant simultanément l'huile algale à l'aide d'un liquide ionique acide tolérant à l'eau - Google Patents

Procédé de rupture de parois de microalgues et d'extraction d'huile tout en estérifiant simultanément l'huile algale à l'aide d'un liquide ionique acide tolérant à l'eau Download PDF

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Publication number
WO2015184629A1
WO2015184629A1 PCT/CN2014/079324 CN2014079324W WO2015184629A1 WO 2015184629 A1 WO2015184629 A1 WO 2015184629A1 CN 2014079324 W CN2014079324 W CN 2014079324W WO 2015184629 A1 WO2015184629 A1 WO 2015184629A1
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Prior art keywords
oil
microalgae
water
ionic liquid
breaking
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PCT/CN2014/079324
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English (en)
Chinese (zh)
Inventor
曾雅秀
黄铭郁
吴荣宗
周金言
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台湾中油股份有限公司
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Priority to PCT/CN2014/079324 priority Critical patent/WO2015184629A1/fr
Publication of WO2015184629A1 publication Critical patent/WO2015184629A1/fr

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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
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/10—Production of fats or fatty oils from raw materials by extracting
    • 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
    • C11B3/00—Refining fats or fatty oils
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/04—Refining fats or fatty oils by chemical reaction with acids

Definitions

  • the invention relates to a method for simultaneously esterifying algae oil by microalgae breaking and extracting oil with water-resistant acidic ionic liquid, in particular to using a water-resistant acidic ionic liquid to break the microalgae and catalyzing the esterification of microalgae oil into The fatty acid methyl ester; the acidic ionic liquid is hydrophilic, and can be automatically stratified with the oil phase of the microalgae oil and the fatty acid methyl ester, thereby achieving the purpose of wall breaking, oil extraction, esterification, oil-water phase separation.
  • Background technique
  • Biomass fuel is the most promising renewable energy source to replace fossil energy in the future.
  • Biodiesel is one of the most commonly used biofuels. Its main component is fatty acid methyl ester (FAME, Fatty Acid Methyl Ester). It is prepared by esterification or transesterification of biomass (lipid).
  • FAME Fatty Acid Methyl Ester
  • Microalgae is a good raw material for the production of quality diesel. Microalgae can synthesize the biomass (saccharides, lipids, proteins) required by sunlight, water and C0 2 .
  • Many microalgae have high oil content, suitable for cultivation. Under the conditions, some oil content is as high as 50 ⁇ 70% of dry algae, and the fatty acid carbon number in microalgae oil is suitable for preparing biodiesel.
  • algae Compared with plants, algae has the characteristics of high photosynthesis efficiency, strong environmental adaptability, short growth cycle and high biological yield. According to conservative estimates, micro-algae can produce 8,200-34,000 L of oil per hectare per year, while oil-rich plants such as palm and jatropha produce only 1,300-2,700 L per hectare.
  • microalgae oil is mostly present in algal cells, and some oils are present in the form of lipoproteins or lipopolysaccharides bound to proteins or sugars, algae cells are wrapped by relatively tough cell walls, making it difficult to extract the oil directly. . Therefore, the algae body needs to be broken before the oil is extracted.
  • Common methods are mainly divided into physical, chemical and biological wall breaking methods. After the microalgae cells are pretreated by some methods of breaking the wall, most of the oil is still stored in the cells, and the oil in the microalgae cells is extracted by a suitable method.
  • the commonly used microalgae oil extraction methods include: organic solvent extraction method, supercritical extraction method, subcritical solvent method and coupled extraction technology.
  • Ionic liquids are structurally composed of an organic cation and an anion Coupled salts, which are liquid at room temperature.
  • the organic cations of ionic liquids are usually organic nitrogen compounds, such as alkylamine, Alkylimidazole, Alkylpyridine organic nitrogen compounds, and anions can be various negatively charged molecules.
  • organic nitrogen compounds such as alkylamine, Alkylimidazole, Alkylpyridine organic nitrogen compounds, and anions can be various negatively charged molecules.
  • ionic liquids have the following characteristics: (1) no vapor pressure; ( 2 ) high boiling point; ( 3 ) low toxicity; ( 4 ) solubility can be adjusted; (5) polarity and conductivity, and is considered to be a green solvent.
  • Ionic liquids have been used to extract proteins from two-phase aqueous solutions, from urine. Extracting hormones from liquids, esterification of oils and fats, and solvents as biodegradable copolymers.
  • an auxiliary base containing pyridine and its derivative
  • the method uses an auxiliary base in combination with an acid (which may be hydrochloric acid, acetic acid, p-toluenesulfonic acid, formamidinesulfonic acid or trifluoromethanesulfonic acid) to form a salt which is a liquid ionic liquid at the reaction temperature. And in a solution in a suitable solvent, a valuable product or a valuable product acid can be formed into a liquid phase which is immiscible.
  • an acid which may be hydrochloric acid, acetic acid, p-toluenesulfonic acid, formamidinesulfonic acid or trifluoromethanesulfonic acid
  • Ionic liquids have been used in the extraction of microalgae algae oil. It has been studied that l-ethyl-3-methyl imidazolium methyl sulfate ([EMIM]S0 3 ) and methanol can be co-solvent at 65°. After 18 hours of C reaction, the algae oil extract of freeze-dried Chlorella was raised from 11.23% to 38%; the ionic liquid against Duniella: a seawater algae without cell wall resistance and high permeability The algae oil extraction rate decreased from 11.1% to 8.6% compared to the conventional rope extraction method (extracted with hexane). In this study, the effect of the type of EMIM co-solution on the extraction rate was also compared. The results were better with methanol and isopropanol.
  • the ionic liquid [EMIM]CI when added by 25 ⁇ 100%, the single-cell or multi-cellular algae with partial dehydration (water content 0 ⁇ 25%) can be broken at 15CTC. Algae oil and ionic liquids can be separated by automatic separation due to differences in hydrophobicity and hydrophilicity.
  • the [EMIM]CI ionic liquid is added to the cell wall microcellulose component of the Chlorella pyreniodosa algae at 1-20%, and the algal oil (triglyceride) is separated at 105-140 °C.
  • the invention provides a method for simultaneously esterifying algae oil by microalgae breaking and extracting oil with water-resistant acidic ionic liquid, and the acidic ionic liquid can catalyze the esterification reaction of methanol-hexane solvent in the algae oil, using the cable type
  • the extraction device can effectively extract the algae oil and esterify the free fatty acid in the algae oil into a fatty acid methyl ester, and can effectively remove the algal residue in the oil or ionic liquid, and the obtained low acid algae oil can be directly applied to the rotation. Esterification process to produce fatty acid methyl ester (FAME, Fatty Acid Methyl Ester).
  • a method for simultaneously esterifying algae oil with a water-resistant acidic ionic liquid for microalgae breaking and oil extraction is as follows:
  • microalgae is broken by a water-resistant acidic ionic liquid to form a first microalgae wall-breaking mixture
  • the first microalgae wall-breaking mixture is placed in a methanol and a first organic solvent to form a second microalgae wall-breaking mixture;
  • the second microalgae wall-breaking mixture is subjected to reflux oil extraction and homo-esterification reaction, followed by filtration to form an upper layer liquid and a lower layer liquid;
  • the first microalgae wall-breaking mixture is a mixture of the water-resistant acidic ionic liquid in a wet algae body, the mass ratio is 5 to 100%, the heating temperature is between 50 and 180 ° C, and the stirring time is between 5 and 300. Minutes, the microalgae broke.
  • refluxing oil extraction and the homologous esterification reaction and filtration are carried out by moving the first microalgae broken wall mixture into a glass fiber material of a cable fat extractor filter paper to add 1 to 50 times the first microalgae to be broken.
  • the volume of the wall mixture and the first organic solvent in a volume of 1 to 50 times the algae solution are refluxed at 50-90 ° C for 2 to 5 hours; the reflux oil extraction and the same
  • the second microalgae wall-breaking mixture after esterification is left to be layered, the upper layer liquid is the first organic solvent of algae oil, and the lower layer liquid is dissolved in the methanol and water by the water-resistant acidic ionic liquid; After the upper liquid and the lower liquid are separated, respectively, vacuum distillation is performed, and the upper liquid can obtain the algal oil and the recovered first organic solvent, and the lower liquid can obtain the methanol and the water resistant acidic ionic liquid.
  • the organic nitrogen-containing compound in the sulfonic acid lactone-containing organic nitrogen-containing compound is a nitrogen compound of Alkylimidazole, Alkylpyridine and Alkylamine.
  • the strong acid of Brunstr is sulfoxide (Thionyl chloride, S0C1 2 ), sulfuric acid (H 2 S0 4 ) or monoterpene sulfonic acid (R-S0 3 H) Bronsted acid.
  • the sulfhydryl group of the Alkylimidazole, Alkylpyridine and Alkylamine nitrogen compounds of the organic nitrogen-containing compound in the sulfonic acid lactone-containing organic nitrogen-containing compound is C m H 2m+1 , where m is from 1 to 18.
  • the sulfonate group of the sulfonate-containing organic nitrogen-containing compound has a sulfonate group of C n H 2n , wherein n is from 3 to 6.
  • sulfonic acid (R-S0 3 H) Bronsted acid is fluorosulfonic acid (FS0 3 H), trifluoromethanesulfonic acid (CF 3 S0 3 H) and p-toluenesulfonic acid (p-CH) 3 -C 6 H 4 -S0 3 H).
  • the wet algae body is mixed with the water-resistant acidic ionic liquid by a mass ratio of 20 to 70%.
  • the wet algae body is mixed with the water-resistant acidic ionic liquid, and a second organic solvent is further added.
  • the second organic solvent is an anthracene hydrocarbon solvent (C n H 2n+2 ), a cyclic anthraquinone hydrocarbon solvent (C n H 2n ), or a mixed organic solvent containing an anthracene hydrocarbon or a cyclic anthracene hydrocarbon.
  • the amount of the terpene hydrocarbon solvent (0 ⁇ 2 . +2 ) in the second organic solvent is between 10% and 100%.
  • the amount of the cyclic anthraquinone solvent (C n H 2n ) in the second organic solvent is between 10% and 100%.
  • the heating temperature is preferably further between 80 and 130 ° C.
  • the stirring time is preferably between 5 and 60 minutes.
  • the volume ratio of the methanol to the first microalgae wall-breaking mixture is preferably between 5 and 30.
  • the first organic solvent is a hydrazine hydrocarbon solvent (C n H 2n+2 ), a cyclic hydrazine hydrocarbon solvent (C n H 2n ), or a mixed organic solvent containing an anthracene hydrocarbon or a cyclic hydrazine hydrocarbon.
  • the amount of the terpene hydrocarbon solvent (0 ⁇ 2 . +2 ) in the first organic solvent is between 10% and 100%.
  • the amount of the cyclic hydrazine hydrocarbon solvent (0 ⁇ 2 ) in the first organic solvent is between 10% and 100%.
  • volume ratio of the first organic solvent to the first microalgae wall-breaking mixture is
  • the wet algae body is a single-cell freshwater or seawater algae whose cell walls are cellulose, pectin and glycoprotein, and is a Chlorella, Chlamydomonas, and a grid. Algae (Scendesmus), Nannochloropsis and Ettlia.
  • the wet algae body is a microalgae cultured in a photoreactor, an open cell or a fermentation tank for self-operating, multi-battalion or mixed culture.
  • the wet algae body is a microalgae obtained by cultivating sea water, fresh water or waste water.
  • the wet algae body is used to remove part of the water for the cultured microalgae by centrifugation, filtration or natural sedimentation, and the wet algae body having a concentration of the algae of 250-1000 g/L is obtained.
  • the invention provides a method for esterifying algae oil by microalgae breaking and oil extraction with water-resistant acidic ionic liquid, and the steps are as follows:
  • PPS pyridinium propyl sulfobetaine
  • Bronsted strong acid such as sulfuric acid (H 2 S0 4 , SA), thionyl chloride (S0CI 2 ) or sulfonic acid (R-S0 3 H a class of trifluoromethanesulfonic acid (CF 3 S0 3 H, TFMSA) and p-toluenesulfonic acid (p-CH 3 -C 6 H 4 -S0 3 H, P-TSA) and other strong acids, at 60 ⁇ 90°
  • the mixture is stirred for 0.5 to 1 hour to obtain a transparent viscous water-resistant acidic ionic liquid, wherein the molar ratio of the strong acid to the amphoteric compound is from 1.0 to 0.5.
  • the solution is allowed to stand layering.
  • the upper layer is dissolved in hexane and the lower layer is acidic ionic liquid dissolved in methanol and water.
  • the upper layer and the lower layer are separately collected for vacuum distillation, and the upper layer can recover algae oil and hexane.
  • the lower layer recovers methanol and acidic ionic liquids.
  • the microalgae of the present invention refers to single-cell freshwater or seawater algae whose cell walls are cellulose (cell U
  • the wet algae body of the present invention refers to the microalgae after being cultured to 1-3 g / L, and then removing part of the water by centrifugation, filtration or natural sedimentation to reach an algae body having a concentration of 250-1000 g/L.
  • the algal oil of the present invention means a mixture of oil-soluble components such as fatty acid methyl ester (FAME) and triglyceride (TAG).
  • FAME fatty acid methyl ester
  • TAG triglyceride
  • the water-resistant acidic ionic liquid of the invention has a wall-breaking oil extraction rate which is 1.1 to 3.8 times higher than that of the same concentration of Brunsten acid under the same conditions; the esterification rate of the algae oil can reach 98.9%.
  • the ionic liquid of the invention can be reused for more than four times, and is only interfered by the accumulation of chlorophyll of the microalgae when used repeatedly, and the rate of broken wall oil is reduced by 7-10%
  • Fig. 1 is a flow chart showing the method for simultaneously esterifying algae oil by microalgae breaking and oil extraction with water-resistant acidic ionic liquid according to the present invention. detailed description
  • a flow chart of a method for simultaneously esterifying algae oil by microalgae breaking and extracting with a water-resistant acidic ionic liquid according to the present invention is as follows:
  • Microalgae cultivation is a microalgae cultivated in a photoreactor, open pond, fermenter seawater, fresh water or wastewater for self-operated, hetero-barrier, mixed operation, and the concentration of microalgae at this time is l ⁇ 3 g/L. ;
  • S12 collecting algae, collecting microalgae, centrifuging, filtering or sedimenting, wherein the concentration of microalgae is 250 ⁇ 1000 g/L;
  • S15 separation of algae oil, the above liquid is allowed to stand layered, the upper layer is dissolved in hexane by the algae oil, and the ionic liquid is dissolved in methanol and water in the lower layer;
  • S16 Solvent and ionic liquid recovery, respectively, the algae oil solution and the ionic solution are distilled under reduced pressure, and the algae oil [FAME] and triglyceride (TG) are recovered, and methanol, hexane, water and ionic liquid are recovered. reusable.
  • Example 1 Water-resistant acidic ionic liquid on the dewatering and refining rate of freshwater algae:
  • the freshwater aquaculture Chlorella sorokiniana was collected by centrifugation, and 10 g of wet algae (dry weight about 0.8 ⁇ ll g) was weighed.
  • the acidic ionic liquid prepared above was added and heated at 60 ° C for 250 min at 250 rpm. , the microalgae broke.
  • the solvent and water are separately concentrated under reduced pressure, and the upper layer liquid can obtain the algal oil product, and the lower layer can recover the acidic ionic liquid.
  • the algae oil product was weighed, and its composition was analyzed by a gas chromatograph, and the oil extraction rate and esterification rate were calculated. The extraction rate and esterification rate are calculated as follows:
  • Oil extraction rate (algal oil weight / dry algae weight) ⁇ 100%
  • Esterification rate (FAME total weight / extraction oil weight) ⁇ 100%
  • the sulfuric acid ionic liquid has a higher oil recovery rate and a catalytic esterification rate than the sulfuric acid in the same molar number of sulfuric acid.
  • Example 2 Comparison of the breakwater extraction and homogenization rate of seawater algae by different acidic ionic liquids: According to the reaction test procedure mentioned in the embodiment, the cultured seawater (containing 3% NaCI) is cultured with Nannochloropsis sp., and the wet algae body is 10 g (dry weight about 1.9-2.1 g). Add 20% (w/w) of acidic ionic liquid and heat and stir at rpm at 90 °C.
  • the oil extraction rates of different acidic ionic liquids containing the same number of moles at 9CTC were PTSA>TFMSA>SA>SOCI 2 ; the catalytic esterification rate was PTSA>SOCI 2 >SA>TFMSA.
  • This trend is different from the results of Example 1 freshwater algae because the oil extraction rate and algal oil esterification rate of different acidic ionic liquids are affected by the difference in cell wall composition of the microalgae and the salt concentration of the algae.
  • the ground leaching oil of Chlorella somkiniana and the lower layer of sulfated ionic liquid recovered after esterification are collected, and the equal weight of hexane is extracted three times to remove residual algal oil.
  • the methanol solvent and water are removed by concentration under reduced pressure, that is, the sulfuric acid ionic liquid is recovered.
  • 20% (w/w) sulfuric acid ionic liquid was added per 10 g of wet algae to carry out algae-breaking oil extraction, and the oil extraction rate and esterification rate were evaluated; the results showed that the ionic liquid can be reused four times.
  • the efficiency of the wall-breaking oil recovery can be maintained at 95% or more, and the esterification efficiency is hardly affected.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

L'invention concerne un procédé de rupture de parois de microalgues tout en extrayant d'huile et en estérifiant simultanément l'huile algale à l'aide d'un liquide ionique acide tolérant à l'eau. Ce liquide ionique acide est utilisé pour extraire une huile algale dans un solvant méthanol-hexane et, en même temps, pour réaliser un procédé d'estérification de l'huile algale ; et le liquide ionique acide et le solvant méthanol-hexane dans le procédé peuvent tous deux être recyclés et réutilisés.
PCT/CN2014/079324 2014-06-06 2014-06-06 Procédé de rupture de parois de microalgues et d'extraction d'huile tout en estérifiant simultanément l'huile algale à l'aide d'un liquide ionique acide tolérant à l'eau WO2015184629A1 (fr)

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PCT/CN2014/079324 WO2015184629A1 (fr) 2014-06-06 2014-06-06 Procédé de rupture de parois de microalgues et d'extraction d'huile tout en estérifiant simultanément l'huile algale à l'aide d'un liquide ionique acide tolérant à l'eau

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
CN109055228A (zh) * 2018-07-10 2018-12-21 大连理工大学 碳酸盐辅助提取微藻油脂并吸收二氧化碳循环培养的方法
CN110354897A (zh) * 2019-02-19 2019-10-22 河北科技大学 一种酸性聚合离子液体树脂催化剂的制备方法和应用

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WO2009114830A2 (fr) * 2008-03-14 2009-09-17 University Of Hawaii Procédés et compositions pour extraction et transestérification de composants de biomasse
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CN1861750A (zh) * 2005-09-09 2006-11-15 清华大学 一种制备生物柴油的方法
WO2009114830A2 (fr) * 2008-03-14 2009-09-17 University Of Hawaii Procédés et compositions pour extraction et transestérification de composants de biomasse
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109055228A (zh) * 2018-07-10 2018-12-21 大连理工大学 碳酸盐辅助提取微藻油脂并吸收二氧化碳循环培养的方法
CN110354897A (zh) * 2019-02-19 2019-10-22 河北科技大学 一种酸性聚合离子液体树脂催化剂的制备方法和应用
CN110354897B (zh) * 2019-02-19 2022-04-26 河北科技大学 一种酸性聚合离子液体树脂催化剂的制备方法和应用

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