WO2011085461A1 - Procédé pour désémulsification et estérification intégrée d'acides gras et de leurs dérivés au moyen de réactifs résiduels et récupération simultanée d'alcool et élimination d'eau - Google Patents

Procédé pour désémulsification et estérification intégrée d'acides gras et de leurs dérivés au moyen de réactifs résiduels et récupération simultanée d'alcool et élimination d'eau Download PDF

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WO2011085461A1
WO2011085461A1 PCT/BR2011/000007 BR2011000007W WO2011085461A1 WO 2011085461 A1 WO2011085461 A1 WO 2011085461A1 BR 2011000007 W BR2011000007 W BR 2011000007W WO 2011085461 A1 WO2011085461 A1 WO 2011085461A1
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process according
carried out
esterification
acid
alcohol
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Portuguese (pt)
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Marcos Vinicios Marques Fagundes
Luciano Bastos Oliveira
Luiz Guilherme Da Costa Marques
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    • 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
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds

Definitions

  • the present invention consists in the breakdown of stable fatty acid emulsions and their derivatives through the isolated or combined use of physical processes, as well as by acidification of the medium followed by esterification by acid catalysis.
  • controlled amounts of alcohol are employed in conjunction with the simultaneous distillation of alcohol and water.
  • This procedure aims to allow the formation of two phases, one apolar containing grease and alcohol and the other polar and denser containing water and alcohol which is removed from the reaction medium thus inhibiting the reverse reaction of esterification that has water as one of your reagents.
  • hydrated alcohol may be used and only the use of anhydrous alcohol in the final stages of the reaction is required.
  • Triglycerides are spontaneously degraded to form fatty acids and glycerin.
  • some residual sources of grease such as sewage treatment plant skim and grease Retaining housings for building toilets are formed almost exclusively by emulsions of fatty acids and water.
  • Others, such as vegetable oil refining lees have a fatty acid content typically between 30% and 70% depending on the process and the raw material employed. Often these sources are considered to be tailings that have limited or no acceptance in the market and therefore have serious disruptions to their final disposal given the range of environmental issues related to them.
  • triglycerides and fatty acids have strong nonpolar character in their molecules, therefore, have limited solubility in polar solvents, such as water. In addition, they have relatively high viscosity. Such characteristics make such compounds prone to form water stable emulsions. Above all, fatty acids that have such high viscosities that they are mostly pasty at room temperature. Thus, aqueous fatty acid emulsions are solid in appearance and contain various types of substances, such as plastics and paper, among others, provided they are available in the medium, as is the case, for example. grease traps and sewage scum.
  • the breakdown of aqueous emulsion is essential for the desired process to occur. This breakdown has been accomplished by extracting the grease with a water-immiscible, but low viscosity, nonpolar solvent. Thus, the resulting nonpolar solution also has low viscosity which allows the coalescence of the dispersed water droplets in the emulsion and the consequent separation of the phases.
  • the first of these is related to the difficulty of its recovery from grease because, due to the existence of Raoult's law, the boiling point of the binary mixture still containing part of the volatile solvent becomes close to the boiling point of the fatty acids, in fact. in some cases exceeding 350 ° Celsius. This temperature is sufficient for a number of undesirable side reactions to occur and also represents a strong energy consumption for the recovery process.
  • Another important issue that deserves comment is the capture of a portion of the solvent in the aqueous phase due to the presence of emulsifying substances that are naturally present in the oils and are purposely added in some cases, such as in the kitchen sinks of the house.
  • the esterification itself can be performed.
  • Acid catalysis esterification typically employs temperatures between 60 ° and 90 ° Celsius and reaction time between 3 hours and 7 hours.
  • the use of excess alcohol is adopted as a way to improve the conversion of reagents to product, which in some patent applications reaches a ratio of up to 10/1 such as PI0500333-4, or even more, as the application for patent PI0301254-9 which advocates up to 15/1 as an efficient way to convert.
  • the conversion to ester in patent application PI0301254-9 is about 60%. This percentage is well inferred from the resolution of ANP 007/2008 which now requires a minimum ester content of 96.5% for the fuel to be classified as biodiesel in Brazil.
  • the purpose of the present invention is to exploit the high acidity grease, whether naturally obtained or produced from glyceride hydrolysis by thermal, enzymatic or otherwise processes, in esterification reactions with short chain alcohols, or more specifically, up to eight carbon atoms by acid catalysis without the use of flammable organic solvents that are harmful to health and the environment in the extraction of the raw material.
  • grease is made available for the esterification process by breaking the aqueous emulsion through the joint use or in isolation of physical demulsification processes such as 2.4 GHz to 2.5 GHZ microwave with exposure time from 0.01 minute to 120 minutes, ultrasound with frequency from 15Khz to 10Mhz, application of electric field using direct or alternating current from 10V / cm to 10KV / cm, use of saturated solution of such as NaCI, among others, or from the chemical process of reducing the pH of the reaction medium using the acid ester catalyst of the esterification reaction which may be residual of the latter having reaction capacity to break the emulsion, what, aided by other processes of separation of the emulsified phases.
  • This procedure is more economically competitive, and more environmentally sound.
  • distillation causes water enrichment in the reaction medium allowing phase separation at a given time.
  • phase separation is achieved, the aqueous phase is decanted quickly if agitation is stopped as there is a large density difference between the phases as well as low viscosity in the reaction medium, especially at temperatures close to the reaction ones. then a new reaction step can be restarted by repeating the cycle with the aqueous phase moving away from the reaction medium.
  • the first step of the present invention is the separation of grease from other contaminants in order to take it suitable for the esterification process.
  • Some sources of grease such as those from household grease traps or primary decanters in sewage treatment plants, have an acid content of around 100%, while others, such as vegetable oil refining sludge, have typical levels in the order of 100%. 30% to 70%.
  • the increase in acidity is related to the natural process of glyceride degradation in fatty acids. Thus, the more degraded the raw material the higher the acidity content.
  • the oxidative rancidity that is related to the reaction with air oxygen and the related hydrolytic rancidity and enzymes that degrade glyceride in aqueous medium.
  • the higher the acidity content the higher the viscosity of the grease and therefore the greater the propensity to form stable emulsions with polar solvents, especially water.
  • water and grease emulsions with water content ranging from 40% to 80% with solid aspect and trapping other materials such as wood chips, paper, plastics, even very high density objects. like sand, small stones and metal. Under these conditions the emulsion is not suitable for use in the esterification process, so these contaminants need to be separated from the grease.
  • the stability of these emulsions is mainly due to two factors.
  • the first of these refers to the high viscosity of grease, which increases significantly with the proportion of fatty acids present.
  • the second factor is related to the occurrence of emulsifying substances that act in the water interphase with the grease matter.
  • These emulsifiers are naturally present in vegetable oils and even petroleum, in addition to In addition, they are purposely added in some cases, such as kitchen sinks to facilitate the transport of grease.
  • most emulsifiers have in their molecule a polar part that has affinity for water and an apolar part with affinity for the grease phase. In this way they form miscelas isolating the dispersed phase from the dispersing phase.
  • one way to break the stability of grease emulsions with water is to heat the emulsion until the viscosity of the grease is reduced to the extent that the water particles that are meeting to form larger particles can move and can occur. the phase separation.
  • heating alone is often not sufficient to break the emulsion due to the presence of emulsifying agents.
  • other methods alone or together may be used to allow phase separation.
  • One is the use of ultrasound equipment to destabilize the emulsion, in which case sound wave frequencies ranging from 15 KHz to over 10 MHz are used.
  • Another way to separate the phases is by using electromagnetic microwaves. frequency between 2.4GHz and 2.5GHz.
  • the polar part of the emulsifying agent is usually formed by an ionic bond between a carbon atom and a strongly electropositive chemical element.
  • one way to depolarize this part of the emulsifier is to replace this electropositive element by reaction with a strong acid so that a more thermodynamically stable ionic salt can be formed than the originally present organic salt.
  • the result of this reaction is the formation of an ionic salt generally soluble in the aqueous medium and a water-insoluble apolar compound unable to form miscellae. Under these conditions, ie, temperature high enough to reduce the viscosity of the grease and pH low enough to depolarize the emulsifier, phase separation may occur.
  • the temperature required to allow droplet coalescence depends on the specific composition of the grease present. However, the values are often within the range of 50 ° to 85 ° Celsius. There are several ways in which this heating can be done, including direct flame, electric heating, the use of thermal fluids and even solar energy due to the low temperatures involved. In addition to this, the heat provided by other processes, such as that released in the distillation stage of the esterified product to be examined below, or the heat from the burning of biogas used to dry the sludge at the wastewater treatment plants, can be used. sewage treatment, or from the burning of methane in landfills, as well as from any other source of heat made available by industrial process. Due to the relatively high temperatures The low temperatures required in the phase separation process, heating is a very simple step and, as can be deduced, can be done by conduction, convection and irradiation.
  • the amount of acid required to depolarize emulsifying agents depends on their concentration. This concentration also depends on the grease, its contaminants and, above all, on the strength and quality of the acid used. This is because residual acids or even from industrial waste may be used. Therefore, only the specific case can safely determine the volume of acid solution to be employed. In cases where concentrated strong acids are used this concentration is between 1% and 25% by weight of the emulsion.
  • the medium is heated and acidified with a strong acid, coalescence of the dispersed phase droplets begins to occur and consequent phase separation.
  • the emulsion should be allowed to settle for a period ranging from one to twenty four hours at a temperature between 50 ° to 85 ° Celsius.
  • the settling time will depend on the viscosity, the average density of the grease being separated and the degree of utilization to be achieved in the settling process.
  • a centrifuge may be used as a means of accelerating phase separation.
  • the impurities of the grease phase can be sieved.
  • the mesh size of the sieve will depend on the average size of the impurities, as they vary greatly according to the origin of the raw material employed.
  • the demulsification can be done continuously or in batch.
  • centrifuges coupled to sieves with mesh suitable for the size of the contaminants present in the specific raw material should be used.
  • the best way to separate the phases is by pouring the grease through a drain in the upper part of the vessel by increasing the internal pressure of the equipment. This can be accomplished by injecting pressurized water into it, or by expanding a plunger or any other equipment to increase the volume of compressed air within the demulsification vessel without, however, letting air escape to the upper part where the desulsified grease is to be poured. In this way, the internal pressure of the vessel can be increased, thus expelling the raw material through the spillway, while sieving it under pressure.
  • Acid de-emulsification often gives off a bad smell, this problem can be mitigated by using tall chimneys, or by venting exhaled gases through deodorizing filters or any other available deodorizing method.
  • the grease Once separated from its contaminants and acidified, the grease will be ready for the esterification process.
  • the first is the presence of 100% acidity grease. In this case, esterification as will be shown later.
  • the second is the existence of mono-, di- and triglycerides mixed with fatty acids. In this situation one can opt for two distinct routes. The first is to hydrolyze the glycerides present converting them into fatty acids and then normally follow the esterification route.
  • the second refers to the esterification of fatty acids, to then transesterify the glycerides present using the basic catalysis.
  • the whole process takes place in acid medium, however there is a higher energy consumption.
  • less energy is consumed but more reagents are consumed as part of the basic catalyst is used to neutralize the acid catalyst.
  • the choice of one or another variant will depend on the acidity content. A presence of triglycerides greater than 50% favors the option for transesterification, a smaller presence favors the option for hydrolysis reaction.
  • the esterification with acid catalysis itself can be performed regardless of how the grease has been separated from its contaminants, ie it may have been extracted with solvents or by any other separation method.
  • Its source of origin can be varied such as sewage scum, grease boxes, industrial processing waste, agricultural processing waste, urban waste and oil refining sludge. It can also be obtained from thermal, enzymatic or chemical catalysis of new or used vegetable oils such as soybean, canola, rapeseed, palm, palm, peanut, sunflower, cotton, olive, coconut, babassu, canola, corn, castor. and Jatropha curcas, as well as animal fats such as beef, pork, goat, sheep and horse tallow, fish oil and chicken fat, duck and turkey.
  • this acid present in the grease may be used as a catalyst in the esterification process to which more acid may or may not be added depending on the specific reaction conditions.
  • a higher catalyst concentration favors the reaction rate and the separation of the aqueous phase from the organic phase by increasing the density and polar character of the catalyst. same. However, it also favors the occurrence of undesirable side reactions such as polymerization, condensation and dehydration among others.
  • catalyst concentrations should be between 0.01% to 25% by weight of the grease to be esterified. Preferably in the range 0.05% to 10%.
  • Suitable acids for the process include homogeneous catalysts such as sulfuric acid, hydrochloric acid, phosphoric acid, sulfonic acid, methanesulfonic acid and toluenesulfonic acid among others.
  • Heterogeneous catalysts having thermal stability and Brönsted and / or Lews acidity may also be used under the conditions of the reaction such as calcium chloride, ferric chloride, zinc chloride, ferric sulfate, sulfated zirconia , niobic acid and zeolites provided they have hydrogen as the exchange cation.
  • the catalyst such as the alcohol employed, may be of inferior quality. This enables the use of residual catalysts or waste from other industrial processes.
  • esterification with acid catalysis has as a slow reaction stage the formation of carbon dioxide, also known as carbocation. Once formed, this ion reacts rapidly with any nucleophilic reagent present in the reaction medium making it possible for several parallel reactions to occur. In addition, the carbon ion undergoes rearrangement to form more stable ions which makes the situation even more complex. Thus, the use of low catalyst concentrations as well as temperatures tend to decrease the occurrence of parallel reactions, conduit slows down the main reaction. Double bonds in unsaturated fatty acids are particularly problematic as they are highly nucleophilic due to the configuration of the p orbitals that make electrons highly available for carbon-ion electrophilic attack.
  • the higher the water concentration in the medium the greater the occurrence of the inverse reaction and, therefore, the lower the esterification reaction conversion.
  • distillation makes the vapor more It is rich in alcohol and the richest liquid phase in this way can result in the two-phase separation of the reaction medium. Due to the low viscosity of the esters formed and the large density difference, the decantation of the aqueous phase occurs between 1 minute and 20 minutes when stirring is stopped. Once the aqueous phase is separated, it may be removed from the reaction medium and subsequently directed to an alcohol recovery process. Once this is done, a new esterification step can be restarted.
  • the reactor has background heating, mechanical stirring can be replaced by hydraulic stirring, since the aqueous phase is denser but has a lower boiling point than the ester formed as well as unreacted fatty acid. This causes bubbles to form at the bottom of the reactor that rise to the surface promoting agitation of the reaction medium.
  • the distillation temperature is an important indicator of the volatile phase composition and therefore of the phase separation of the reaction medium, so the following temperature ranges should be observed in order to stop heating and allow the aqueous phase to settle if reaction is being processed at atmospheric pressure.
  • water separates when the temperature is between 69 ° and 78 ° Celsius, which corresponds to a concentration of water in the aqueous solution between 30% and 70% mole fraction of water, which can be verified.
  • water withdrawal may be conducted only by distilling the water and alcohol mixture simultaneously with the esterification reaction.
  • water withdrawal is possible only with distillation even for the more volatile alcohols than water, due to Raoult's law, the liquid part becomes increasingly rich in water. This necessitates the use of large amounts of alcohol and energy to be able to remove all the water present without compromising the degree of conversion of the reaction.
  • the esterification reaction may be carried out at a temperature below the atmosphere by the use of a vacuum pump or at pressures higher than the pressure with the use of pressurized vessels.
  • the temperature range described above will vary.
  • lower pressures decrease the reaction speed, as well as the occurrence of parallel reactions due to temperature drop, on the other hand, the use of high pressures has the opposite effect.
  • Agitation can be mechanical, hydraulic or compressed air acting both together and separately.
  • the process heating system has characteristics similar to those exhibited for demulsification, including temperatures close to atmospheric pressure reactions. However, in esterification reactions with pressurized systems the temperature can rise significantly.
  • reaction rate increases greatly with the start of each new step. This is because water that inhibits product formation and slows down the reaction rate is removed at the end of the previous step. This way, each cycle lasts between 10 minutes and 80 minutes on average with conversions between 40% and 60% in contrast to the traditional process that uses between three and seven hours for each reaction step with yields around 60%.
  • part of the alcohol is recovered simultaneously with the reaction itself which reduces the total processing time.
  • Another advantage of the process resulting from this invention is that hydrated alcohol may be used in the early stages of the esterification reaction.
  • ethanol is less dangerous than methanol, which is the main reagent used by current processes.
  • ethanol is predominantly produced from biomass, which gives it a renewable character thus enhancing the environmental appeal of bio-oil or biodiesel produced from this reagent.
  • methanol may also be of renewable origin, as it may be obtained by pyrolysis of the material itself rejected by the esterification process, or from the distillation of the esterified material as well as from any urban, industrial or agricultural organic waste.
  • a drain can be used below the bottom of the reactor, which bottom should be tilted with the drain as its lowest elevation point.
  • a reservoir below the bottom of the reactor without agitation and preferably kept at a temperature slightly lower than the reaction medium in order to accumulate the decanted polar phase within it.
  • this reservoir may also be provided with a valve with intermediate density between the nonpolar and polar phase to close when the reservoir is full of the denser polar phase.
  • communication between the reservoir and the vessel housing the reaction medium should be small to reduce contact between the two phases when the valve is open. If process operation is continuous, perfect mix type reactors for homogeneous catalysts or fixed bed reactors for heterogeneous catalysts may be employed.
  • the ester produced by the above process is cooled to room temperature and then washed with cold water. If liquid catalyst has been used, it is recommended to use two to five washing steps, using pure water or aqueous alcohol solution with contents ranging from 10% to 40% by weight of alcohol.
  • the volume of water or alcohol solution to be employed in each step should be between 30% and 100% of the volume of the esterified product to be washed. This allows virtually all of the remaining catalyst to be removed as well as other polar contaminants that may be present.
  • the wash water of this process can be neutralized with commercial neutralizing reagents such as NaOH, KOH, CaCO 3 , Na 2 CO 3 and ammonia, or if alkaline solutions are used.
  • solid catalyst it can be physically or chemically supported, it can also come in various forms such as powder, pellet, pellet and molded. Whatever the presentation, it may be necessary to recover it by some sorting process such as filtration, decantation and centrifugation. Depending on the type of catalyst and reaction conditions the recovered solid catalyst can be regenerated.
  • this ester may be used as a filler in other types of biodiesel obtained from vegetable oils, or as a bio-oil, provided that it undergoes at least one filtration process which may be accompanied by discoloration and / or deodorization.
  • this ester in order to remove the dark color and the remaining odor it is necessary to purify it with vacuum distillation of the obtained esters which must be carried out at pressures below 350 mm Hg and at temperatures below 350 ° Celsius. These are the limit conditions to prevent product degradation. The more drastic the reaction conditions, the greater the occurrence of undesirable reactions.
  • the fraction of esterified and distilled matter usually represents between 50% and 90% of the total esterified volume.
  • the undistilled part undergoes some degradation, it can be harnessed as a source of energy in the process itself or marketed as bio-oil.
  • the distillation process can occur not only after the last esterification step, but also between them. However, washing for catalyst removal is of paramount importance.
  • distillation during the intermediate steps has the drawback of requiring a higher consumption of acid catalyst, and therefore neutralization reagent, if the process occurs through the homogeneous catalysis route.
  • it has the advantage of immediately improving the smell, color and reaction control conditions.
  • Distillation may also be used to purify fatty acid prior to the esterification reaction.
  • special attention should be paid to the cooling fluid which needs to be carefully controlled since, due to the high viscosity of the fatty acids, they can clog the condenser. Therefore, most of the time it is not necessary to use any refrigerant to make the condensation, only the cooling resulting from the contact of the equipment with the atmosphere of the place is enough.
  • the distillation of fatty acid prior to esterification has the advantage of avoiding the drawbacks of the presence of supporting grease contaminants making reaction control conditions easier, especially with the removal of color and odor early in the process.
  • steam dragging with water may be used to assist in the vacuum distillation of fatty acid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General 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 Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention consiste en la déstabilisation d'émulsions d'acides gras et d'eau en vue d'une utilisation ultérieure comme matière première dans la réaction d'estérification en présence d'alcools à chaîne courte, avec mise à profit comme catalyseur de l'acide restant utilisé dans l'étape de désémulsification. En outre, le procédé d'estérification fait intervenir une distillation simultanée d'alcool et d'eau pendant la réaction d'estérification, et utilise également une séparation de phases du milieu réactionnel en vue d'éliminer la phase aqueuse et, par conséquent, de favoriser la conversion de l'estérification. L'utilisation de la présente invention permet de réduire la taille des équipements, la consommation d'énergie et de réactifs ainsi que le temps total de traitement, et d'obtenir une meilleure conversion en produits par comparaison avec les techniques d'estérification actuellement disponibles. Par ailleurs, elle permet de traiter des matières premières à indice d'acidité élevé qui, de ce fait, sont difficiles ou impossibles à commercialiser, telles que celles présentes dans l'écume d'égouts et dans les collecteurs de graisse de restaurants.
PCT/BR2011/000007 2010-01-18 2011-01-17 Procédé pour désémulsification et estérification intégrée d'acides gras et de leurs dérivés au moyen de réactifs résiduels et récupération simultanée d'alcool et élimination d'eau Ceased WO2011085461A1 (fr)

Applications Claiming Priority (2)

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BRPI1000113A BRPI1000113B1 (pt) 2010-01-18 2010-01-18 processo para desemulsificação e esterificação integrada de ácidos graxos e seus derivados com emprego de reagentes residuais e recuperação simultânea de álcool e retirada de água
BRPI1000113-1 2010-01-18

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WO2011085461A1 true WO2011085461A1 (fr) 2011-07-21

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107010706A (zh) * 2017-05-16 2017-08-04 昌邑市银江生物科技有限公司 一种利用花生壳提取物分离水中铜盐的方法
WO2023159293A1 (fr) * 2022-02-24 2023-08-31 Brasil Bio Fuels S.A Composition, procédé de production de triglycérides et de glycérides partiaux à faible acidité et produit ainsi obtenu

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR9007038A (pt) * 1989-01-17 1991-11-12 Davy Mckee London Processo e aparelho
WO2004099115A1 (fr) * 2003-05-06 2004-11-18 Coppe/Ufrj - Coordenação Dos Programas De Pós Graduação De Engenharia Da Universidade Federal Do Rio De Janeiro Procede d'extraction et d'esterification catalytique d'acides gras se trouvant dans l'ecume des eaux usees
WO2006081644A2 (fr) * 2005-02-02 2006-08-10 Universidade Federal Do Rio De Janeiro-Ufrj Procede catalytique d'esterification d'acides gras
EP1942095A2 (fr) * 2004-06-15 2008-07-09 Carnegie Mellon University Procédés de production de biodiesel

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR9007038A (pt) * 1989-01-17 1991-11-12 Davy Mckee London Processo e aparelho
WO2004099115A1 (fr) * 2003-05-06 2004-11-18 Coppe/Ufrj - Coordenação Dos Programas De Pós Graduação De Engenharia Da Universidade Federal Do Rio De Janeiro Procede d'extraction et d'esterification catalytique d'acides gras se trouvant dans l'ecume des eaux usees
EP1942095A2 (fr) * 2004-06-15 2008-07-09 Carnegie Mellon University Procédés de production de biodiesel
WO2006081644A2 (fr) * 2005-02-02 2006-08-10 Universidade Federal Do Rio De Janeiro-Ufrj Procede catalytique d'esterification d'acides gras

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107010706A (zh) * 2017-05-16 2017-08-04 昌邑市银江生物科技有限公司 一种利用花生壳提取物分离水中铜盐的方法
CN107010706B (zh) * 2017-05-16 2021-04-16 昌邑市银江生物科技有限公司 一种利用花生壳提取物分离水中铜盐的方法
WO2023159293A1 (fr) * 2022-02-24 2023-08-31 Brasil Bio Fuels S.A Composition, procédé de production de triglycérides et de glycérides partiaux à faible acidité et produit ainsi obtenu

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BRPI1000113A2 (pt) 2011-08-30

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