JP4568565B2 - Method for producing fats and oils with reduced free fatty acids - Google Patents

Method for producing fats and oils with reduced free fatty acids Download PDF

Info

Publication number
JP4568565B2
JP4568565B2 JP2004271690A JP2004271690A JP4568565B2 JP 4568565 B2 JP4568565 B2 JP 4568565B2 JP 2004271690 A JP2004271690 A JP 2004271690A JP 2004271690 A JP2004271690 A JP 2004271690A JP 4568565 B2 JP4568565 B2 JP 4568565B2
Authority
JP
Japan
Prior art keywords
oil
fat
fatty acid
free fatty
oils
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.)
Expired - Fee Related
Application number
JP2004271690A
Other languages
Japanese (ja)
Other versions
JP2006083343A (en
Inventor
賢紀 新居
利照 小松
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.)
Kao Corp
Original Assignee
Kao Corp
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 Kao Corp filed Critical Kao Corp
Priority to JP2004271690A priority Critical patent/JP4568565B2/en
Publication of JP2006083343A publication Critical patent/JP2006083343A/en
Application granted granted Critical
Publication of JP4568565B2 publication Critical patent/JP4568565B2/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Fats And Perfumes (AREA)
  • Edible Oils And Fats (AREA)

Description

本発明は、遊離脂肪酸を含有する油脂組成物から遊離脂肪酸が効率良く除去された油脂の製造方法に関する。   The present invention relates to a method for producing fats and oils in which free fatty acids are efficiently removed from fat and oil compositions containing free fatty acids.

食用として有用な油脂を製造する際に、油脂組成物中に生成する余分な遊離脂肪酸を除去するために、脱酸という操作が行われる。例えば、油脂中から飽和脂肪酸のみを選択的に加水分解し、これを系外へ除去する場合や、脂肪酸とグリセリンを反応させて油脂を製造する際に、過剰に添加した余分な遊離脂肪酸を反応後に除去する場合等である。この場合、ある程度の量までは蒸留により除去することができるが、完全に除去することはできないため、通常はアルカリ水溶液を用いて脂肪酸の塩とし、水分を除去し脂肪酸塩を析出させて除去する方法が一般的である(特許文献1参照)。   When producing fats and oils useful for edible use, an operation called deoxidation is performed in order to remove excess free fatty acids produced in the fat and oil composition. For example, when selectively hydrolyzing only saturated fatty acids from fats and oils and removing them out of the system, or when producing fats and oils by reacting fatty acids with glycerin, excess excess fatty acids added are reacted. For example, when it is removed later. In this case, it can be removed by distillation up to a certain amount, but it cannot be completely removed. Therefore, it is usually converted to a fatty acid salt using an alkaline aqueous solution, and the water is removed and the fatty acid salt is precipitated to be removed. The method is general (see Patent Document 1).

しかし、この方法では油脂の一部が鹸化するため油脂の収率が低下し、また脂肪酸の含有量が多い場合はアルカリ石鹸による乳化を生じて分離が困難となる。さらに、脂肪酸が多量に存在する場合に予め蒸留により除去しようとすると、熱履歴が高くなるため、特に高度不飽和脂肪酸を多く含む油脂の場合は健康上望ましくないとされるトランス酸が生じてしまい好ましくない。   However, in this method, a part of the fats and oils is saponified, so that the yield of the fats and oils is reduced. When the fatty acid content is high, emulsification with an alkaline soap is caused and separation becomes difficult. Furthermore, if the fatty acid is present in a large amount, if it is previously removed by distillation, the heat history becomes high, resulting in the generation of trans acid, which is undesirable for health especially in the case of fats and oils containing a large amount of highly unsaturated fatty acids. It is not preferable.

そこで、撹拌せずに油脂の表面にアルカリ水溶液を噴霧する方法(特許文献2参照)、アルカリを特定の溶媒に溶かし、油脂と接触させて抽出する方法(特許文献3、及び4参照)等が提案されている。しかし、これらの方法は、油脂中に含有される遊離脂肪酸の量が少ない場合には有効であるが、含有量が多い場合には遊離脂肪酸の除去効率が低下してしまう。また、有機溶媒に油脂組成物を溶解し、アルカリ水溶液を加えて撹拌し、アルカリ石鹸を沈殿させる方法等もある(特許文献5参照)。しかし、この方法では濾過効率の点であまり効果的ではない。
特開昭53−84911号公報 特開昭60−248798号公報 特開平1−207258号公報 特開平2−308896号公報 特開平2−214798号公報
Therefore, there are a method of spraying an alkaline aqueous solution onto the surface of the oil and fat without stirring (see Patent Document 2), a method of dissolving the alkali in a specific solvent and bringing it into contact with the oil and fat (see Patent Documents 3 and 4), etc. Proposed. However, these methods are effective when the amount of free fatty acid contained in the oil and fat is small, but when the content is large, the removal efficiency of free fatty acid is lowered. In addition, there is a method of dissolving an oil and fat composition in an organic solvent, adding an aqueous alkaline solution and stirring to precipitate an alkaline soap (see Patent Document 5). However, this method is not very effective in terms of filtration efficiency.
JP-A-53-84911 JP 60-248798 A JP-A-1-207258 JP-A-2-308896 JP-A-2-214798

本発明は、遊離脂肪酸を含有する油脂組成物から効率的に、低コストで脂肪酸が除去された油脂の製造方法を提供することを目的とする。   An object of this invention is to provide the manufacturing method of the fats and oils from which the fatty acid was efficiently removed from the fats and oils composition containing a free fatty acid at low cost.

そこで本発明者は、従来のアルカリ剤を使用する方法を改良し、生じた脂肪酸石鹸を系内で析出させ、水分を除去することなく、単に濾過するのみで除去する方法を探索したところ、アルカリ剤と有機溶剤とを別々に油脂に添加するのでなく、アルカリ剤と水と有機溶剤とを予め混合した液に油脂を添加することが有効であることを見出し、本発明を完成した。   Therefore, the present inventor improved a method using a conventional alkali agent, and precipitated a fatty acid soap produced in the system, and searched for a method of removing it by simply filtering without removing moisture. The present invention was completed by finding that it is effective to add an oil and fat to a liquid prepared by previously mixing an alkali agent, water and an organic solvent, instead of adding the agent and the organic solvent separately to the oil and fat.

すなわち、本発明は、予め調製した、(A)アルカリ剤、(B)有機溶媒及び(C)水を含有する調製液(D)に、遊離脂肪酸を含有する油脂組成物を混合し、次いで当該混合液を撹拌後固液分離する、油脂組成物から遊離脂肪酸が除去された油脂の製造方法を提供するものである。   That is, this invention mixes the fats and oils composition containing a free fatty acid with the preparation liquid (D) which prepared beforehand (A) alkaline agent, (B) organic solvent, and (C) water, Then, the said The present invention provides a method for producing fats and oils in which free fatty acids have been removed from the fat and oil composition, wherein the mixed liquid is subjected to solid-liquid separation after stirring.

本発明によれば、遊離脂肪酸を含有する油脂組成物から、簡便に高い効率で、かつ低コストで遊離脂肪酸が除去された油脂を製造することが可能となる。特に、遊離脂肪酸を多量に含有する場合であっても、脱脂肪酸効率が低下せず、低コストで脱脂肪酸された油脂を製造することが可能となる。   ADVANTAGE OF THE INVENTION According to this invention, it becomes possible to manufacture the fats and oils from which the free fatty acid was removed simply and with high efficiency from the fat and oil composition containing free fatty acid. In particular, even when a large amount of free fatty acid is contained, the efficiency of defatting does not decrease, and it becomes possible to produce fat and oil that has been defatty acid at low cost.

本発明において使用する成分(A)のアルカリ剤としては、アルカリ金属又はアルカリ土類金属の水酸化物、及び炭酸塩を用いることができる。具体的には、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸ナトリウム、炭酸水素ナトリウム等を用いることができるが、アルカリ金属又はアルカリ土類金属の水酸化物が好ましく、中でも水酸化ナトリウム、水酸化カルシウムを用いることが固液分離効率(濾過速度)、及び油脂分離性(グリセリド回収率)の点から好ましい。アルカリ剤の使用量は、油脂組成物中に含有される遊離脂肪酸の量に左右されるが、調製液(D)中の含有量を遊離脂肪酸に対して100〜1000モル%、さらに150〜500モル%、特に170〜300モル%とすることが、上記同様固液分離効率及び油脂分離性の点から好ましい。   As the alkali agent of component (A) used in the present invention, alkali metal or alkaline earth metal hydroxides and carbonates can be used. Specifically, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, sodium hydrogen carbonate, and the like can be used, and alkali metal or alkaline earth metal hydroxides are preferable, among which sodium hydroxide, It is preferable to use calcium hydroxide from the viewpoints of solid-liquid separation efficiency (filtration rate) and oil / fat separability (glyceride recovery rate). The amount of the alkaline agent used depends on the amount of free fatty acid contained in the oil / fat composition, but the content in the preparation liquid (D) is 100 to 1000 mol%, more preferably 150 to 500, based on the free fatty acid. It is preferable to set it as mol%, especially 170-300 mol% from the point of solid-liquid separation efficiency and oil-fat separability like the above.

本発明において使用する成分(B)の有機溶剤としては、メチルアルコール、エチルアルコール等の低級アルコール、アセトン、酢酸エチル、クロロホルム、ヘキサン等が挙げられるが、食品の製造工程で使用可能なエタノール、アセトン、ヘキサンが好ましく、中でもエタノール、アセトンを用いることが固液分離効率、油脂分離性の点から好ましい。有機溶剤の使用量は、調製液(D)中の含有量を10〜97質量%、さらに50〜95質量%、特に60〜90質量%とすることが、遊離脂肪酸の除去率を向上できる点、固液分離効率を向上できる点から好ましい。   Examples of the organic solvent of component (B) used in the present invention include lower alcohols such as methyl alcohol and ethyl alcohol, acetone, ethyl acetate, chloroform, hexane and the like. Ethanol and acetone that can be used in food production processes Of these, hexane is preferable, and ethanol and acetone are particularly preferable from the viewpoint of solid-liquid separation efficiency and oil / fat separability. The amount of the organic solvent used is such that the content in the preparation liquid (D) is 10 to 97% by mass, further 50 to 95% by mass, particularly 60 to 90% by mass, and the removal rate of free fatty acids can be improved. From the point that the solid-liquid separation efficiency can be improved.

本発明において使用する成分(C)の水は、通常の水であり、精製水を用いることが好ましい。(C)水の使用量は、調製液(D)中の含有量を0.01〜99.99質量%、さらに1〜50質量%、特に3〜10質量%とすることが、遊離脂肪酸の除去率、遊離脂肪酸を除去した後の油脂組成物の回収率を向上できる点から好ましい。   The water of component (C) used in the present invention is ordinary water, and it is preferable to use purified water. (C) The amount of water used is such that the content in the preparation liquid (D) is 0.01 to 99.99% by mass, further 1 to 50% by mass, particularly 3 to 10% by mass. The removal rate and the recovery rate of the oil / fat composition after removing the free fatty acids are preferable.

本発明においては、前記成分(A)、(B)及び(C)は、油脂組成物と別個に混合するのでなく、(A)、(B)及び(C)を含有する調製液(D)を予め調製しておき、これに遊離脂肪酸を含有する油脂組成物を混合することが、固液分離効率及び油脂分離性の点で必要である。当該調製液(D)の調製手段としては、特に限定されないが、(A)アルカリ剤及び(C)水を含有する液と(B)有機溶剤とを混合することにより調製するのが、油脂分離性、脱脂肪酸効率の点で好ましい。
また、本発明においては、(B)有機溶剤/(C)水の質量比が2〜100とすることが好ましく、さらに4〜50、特に5〜25、殊更6〜20とすることが、遊離脂肪酸の除去率、遊離脂肪酸を除去した後の油脂組成物の回収率を向上できる点から好ましい。
In the present invention, the components (A), (B) and (C) are not separately mixed with the oil and fat composition, but a preparation solution (D) containing (A), (B) and (C). It is necessary from the viewpoint of solid-liquid separation efficiency and oil / fat separability that an oil / fat composition containing a free fatty acid is mixed in advance. The preparation means of the preparation liquid (D) is not particularly limited, but it is oil / fat separation that is prepared by mixing (A) a liquid containing an alkali agent and (C) water and (B) an organic solvent. From the viewpoint of the property and the defatty acid efficiency.
In the present invention, the mass ratio of (B) organic solvent / (C) water is preferably 2 to 100, more preferably 4 to 50, particularly 5 to 25, and especially 6 to 20 It is preferable from the point which can improve the recovery rate of the fat and oil composition after removing the fatty acid removal rate and free fatty acid.

本発明に用いられる遊離脂肪酸を含有する油脂組成物としては、脂肪酸とグリセリンとのエステル化により得られる油脂組成物、油脂を高圧加水分解、酵素加水分解、アルカリ処理、加熱処理等することにより得られる油脂分解物等が挙げられる。これらの油脂組成物における油脂には、トリグリセリド、ジグリセリド及びモノグリセリドが含まれる。   As an oil and fat composition containing a free fatty acid used in the present invention, an oil and fat composition obtained by esterification of a fatty acid and glycerin, obtained by subjecting the oil to high-pressure hydrolysis, enzymatic hydrolysis, alkali treatment, heat treatment, etc. And the like. The fats and oils in these fat and oil compositions include triglycerides, diglycerides and monoglycerides.

本発明方法は、油脂組成物中の遊離脂肪酸含量が高いものにも適用可能である。油脂組成物中の遊離脂肪酸含量は、0.01〜99.99質量%、さらに20〜80質量%、特に50〜70質量%であることが、本願発明の特徴である低コストで、効率的に脂肪酸を分離可能である点から好ましい。   The method of the present invention is also applicable to those having a high free fatty acid content in the oil and fat composition. The free fatty acid content in the oil and fat composition is 0.01 to 99.99% by mass, more preferably 20 to 80% by mass, and particularly 50 to 70% by mass. In view of the fact that the fatty acid can be separated.

また、本発明方法は、油脂組成物における構成脂肪酸中の不飽和脂肪酸含量が高い場合でもトランス酸の生成がなく、好ましい。すなわち、本発明方法は、構成脂肪酸中の不飽和脂肪酸含量が1質量%以上、さらに40〜100質量%、特に70〜90質量%である油脂組成物にも適用することができる。   In addition, the method of the present invention is preferable because there is no generation of trans acid even when the content of unsaturated fatty acids in the constituent fatty acids in the oil and fat composition is high. That is, the method of the present invention can be applied to an oil and fat composition having an unsaturated fatty acid content in the constituent fatty acid of 1% by mass or more, further 40 to 100% by mass, particularly 70 to 90% by mass.

油脂組成物と調製液(D)との混合手段は特に限定されないが、調製液(D)に油脂組成物を添加するのが好ましく、特に調製液(D)に対して油脂組成物を徐々に添加、さらに滴下するのが好ましい。添加にかける時間は0.2〜20分、さらに0.5〜5分程度とすることが好ましい。すなわち、例えば油脂組成物1kgを処理する場合は、添加速度は、0.05〜5kg−油脂組成物/分、さらに0.2〜2kg−油脂組成物/分とすることが好ましい。調製液(D)は、油脂組成物100質量部に対して100〜800質量部、さらに200〜600質量部、特に300〜500質量部用いるのが、遊離脂肪酸の除去率、遊離脂肪酸を除去した後の油脂組成物の回収率を向上できる点から好ましい。また、油脂組成物と調製液(D)の混合温度は、0〜50℃、さらに10〜40℃、特に20〜35℃が好ましい。   The mixing means of the oil / fat composition and the preparation liquid (D) is not particularly limited, but the oil / fat composition is preferably added to the preparation liquid (D), and the oil / fat composition is gradually added to the preparation liquid (D). Addition and further dropwise addition are preferred. The time taken for the addition is preferably about 0.2 to 20 minutes, more preferably about 0.5 to 5 minutes. That is, for example, when 1 kg of the oil / fat composition is processed, the addition rate is preferably 0.05 to 5 kg-oil / fat composition / min, and more preferably 0.2 to 2 kg-oil / fat composition / min. The preparation liquid (D) is 100 to 800 parts by mass, more preferably 200 to 600 parts by mass, and particularly 300 to 500 parts by mass with respect to 100 parts by mass of the fat and oil composition. It is preferable from the viewpoint that the recovery rate of the later oil and fat composition can be improved. Moreover, the mixing temperature of the oil and fat composition and the preparation liquid (D) is preferably 0 to 50 ° C, more preferably 10 to 40 ° C, and particularly preferably 20 to 35 ° C.

本発明においては、次に当該混合液を撹拌する。撹拌条件は、油脂組成物と調製液(D)とが、均一に分散できる条件であれば特に限定されないが、好ましくは0.1〜5kW/m3、さらに好ましくは0.2〜3kW/m3の撹拌動力での撹拌が望ましい。撹拌動力が小さい場合、脂肪酸塩の生成が不充分で油脂回収率が低くなる。撹拌動力が大きい場合、微細結晶の生成により固液分離効率が低下する。撹拌することにより、遊離脂肪酸塩が生成するので、これを固液分離することにより油脂組成物と脂肪酸塩とを分離することができる。ここで、固液分離手段としては、油脂組成物と脂肪酸塩と溶剤の混合物を、濾紙または濾布、金網等を使用し、減圧又は加圧濾過を行う方法、遠心分離を行う方法等が挙げられる。操作の簡便性や、回収率の点から濾過が好ましい。これらの撹拌及び固液分離は、0〜40℃、さらに20〜35℃で行うのが好ましい。 In the present invention, the mixture is then stirred. Stirring conditions are not particularly limited as long as the oil and fat composition and the preparation liquid (D) can be uniformly dispersed, but are preferably 0.1 to 5 kW / m 3 , more preferably 0.2 to 3 kW / m. Stirring with a stirring power of 3 is desirable. When the stirring power is small, the production of fatty acid salts is insufficient and the oil recovery rate is low. When the stirring power is large, the solid-liquid separation efficiency decreases due to the formation of fine crystals. Since the free fatty acid salt is produced by stirring, the oil and fat composition and the fatty acid salt can be separated by solid-liquid separation. Here, examples of the solid-liquid separation means include a method of performing filtration under reduced pressure or pressure using a filter paper or a filter cloth, a wire mesh, etc., a method of performing centrifugal separation, etc. It is done. Filtration is preferable from the viewpoint of easy operation and recovery. These stirring and solid-liquid separation are preferably performed at 0 to 40 ° C, and more preferably at 20 to 35 ° C.

本発明方法によれば、特に加熱や冷却することなく、油脂組成物中の遊離脂肪酸が効率良く脂肪酸塩として沈殿し、その沈殿は固液分離性が良好であることから、油脂分離性も良好である。また、不飽和脂肪酸含量の高い油脂組成物を原料とした場合、加熱操作などをすることなく遊離脂肪酸が効率良く除去できるので、得られた油脂組成物中にトランス酸の生成がない。従って、本発明により得られた油脂組成物は食用油脂として特に好ましい。   According to the method of the present invention, the free fatty acid in the oil and fat composition is efficiently precipitated as a fatty acid salt without particularly heating or cooling, and the precipitate has good solid-liquid separation, so that the oil and fat separation is also good. It is. Further, when an oil or fat composition having a high unsaturated fatty acid content is used as a raw material, free fatty acid can be efficiently removed without performing a heating operation and the like, and thus no trans acid is produced in the obtained oil or fat composition. Therefore, the oil and fat composition obtained by the present invention is particularly preferable as an edible oil and fat.

〔原料油脂の調製〕
マグロ油(日本化学飼料(株)製)をリパーゼ-OF(名糖産業(株)製)で加水分解した後、遠心分離を行い、油相を分取し原料油脂組成物(E1)(AV値、123.3)とした。また、ナタネ油と大豆油の混合物をリパーゼ-OF(名糖産業(株)製)で加水分解した後、遠心分離を行い、油相を分取し原料油脂組成物(E2)(AV値、118.6)を調製した。表1にそれぞれの原料油脂組成物の酸価、脂肪酸組成、及びグリセリド組成表を示す。なお、酸価は、基準油脂分析法(2.3.1-1996)に基づき測定した。脂肪酸組成はガスクロマトグラフィーにより、グリセリド組成は液クロマトグラフィーにより分析を行った。
[Preparation of raw oil and fat]
Tuna oil (manufactured by Nippon Chemical Feed Co., Ltd.) is hydrolyzed with lipase-OF (manufactured by Meito Sangyo Co., Ltd.), and then centrifuged to separate the oil phase, and the raw oil composition (E1) Value, 123.3). In addition, a mixture of rapeseed oil and soybean oil was hydrolyzed with lipase-OF (manufactured by Meito Sangyo Co., Ltd.), and then centrifuged, and the oil phase was separated to obtain a raw oil / fat composition (E2) (AV value, 118.6) was prepared. Table 1 shows the acid value, fatty acid composition, and glyceride composition table of each raw oil composition. The acid value was measured based on the standard fat analysis method (2.3.1-1996). The fatty acid composition was analyzed by gas chromatography, and the glyceride composition was analyzed by liquid chromatography.

Figure 0004568565
Figure 0004568565

実施例1
300mL丸底フラスコに水(C)5gと水酸化カルシウム(A)6.5gを添加し、弱撹拌する。さらにアセトン(B)を75g添加し、400r/minで均一に撹拌して調製液(D)とした。液温20℃の条件とした調製液(D)に、撹拌しながら原料油脂組成物(E1)を20g/分の速度で20g滴下した。滴下後20分継続して撹拌し、その後φ70規格No.2の濾紙を使用し、減圧濾過を行った。濾液中のアセトンをエバポレーターにてトッピングし、得られた油脂に70℃蒸留水を対油脂100質量%添加し、70℃下で撹拌湯洗を行った。その後遠心分離し、油相を回収した。上記減圧濾過の際の速度、及び得られた油相の脂肪酸組成、グリセリド組成、酸価、及びグリセリド回収率を表2に示す。なお、濾過速度は、反応停止後(滴下した後20分後)速やかに、φ70規格No.2の濾紙を使用し、減圧濾過を行った時の液切れが終了するまでの時間を計測し、算出した。
Example 1
Add 5 g of water (C) and 6.5 g of calcium hydroxide (A) to a 300 mL round bottom flask and gently stir. Further, 75 g of acetone (B) was added and stirred uniformly at 400 r / min to obtain a preparation liquid (D). 20 g of raw material oil-fat composition (E1) was dripped at the speed | rate of 20 g / min, stirring to the preparation liquid (D) made into the conditions of liquid temperature 20 degreeC. After dropping, the mixture was continuously stirred for 20 minutes, and then filtered under reduced pressure using a filter paper of φ70 standard No. 2. Acetone in the filtrate was topped with an evaporator, 70 ° C. distilled water was added to the obtained oil / fat at 100 mass%, and the mixture was washed with hot water at 70 ° C. with stirring. Thereafter, the mixture was centrifuged to recover the oil phase. Table 2 shows the speed during the vacuum filtration and the fatty acid composition, glyceride composition, acid value, and glyceride recovery rate of the obtained oil phase. The filtration rate was measured immediately after the reaction was stopped (20 minutes after dropping) using a filter paper of φ70 standard No. 2, and the time until the liquid was completely drained when vacuum filtration was performed, Calculated.

実施例2〜7
表2に記載した各成分について、実施例1と同様の操作により、原料油脂組成物(E1)(実施例2〜6)、及び(E2)(実施例7)について脂肪酸の分離を行った。なお、実施例6の成分(B)は、予めアセトンとエタノールを混合した後、(C)と(A)の混合物に添加した。結果を表2に示す。
Examples 2-7
About each component described in Table 2, the fatty acid separation was performed about raw material oil-fat composition (E1) (Examples 2-6) and (E2) (Example 7) by the same operation as Example 1. FIG. In addition, after mixing acetone and ethanol previously, the component (B) of Example 6 was added to the mixture of (C) and (A). The results are shown in Table 2.

比較例1〜3
表2に記載した各成分について、300mL丸底フラスコに(C)(比較例1及び2)、又は(B)(比較例3)と(A)を添加し、調製液とした。その他は実施例1と同様の操作により原料油脂組成物(E1)について脂肪酸の分離を行った。結果を表2に示す。
Comparative Examples 1-3
About each component described in Table 2, (C) (comparative examples 1 and 2) or (B) (comparative example 3) and (A) was added to a 300 mL round bottom flask, and it was set as the preparation liquid. Other than that, fatty acids were separated from the raw oil / fat composition (E1) by the same operation as in Example 1. The results are shown in Table 2.

比較例4及び5
300mL丸底フラスコにアセトン(B)及び原料油脂組成物(E1)を添加し、400r/minで均一に撹拌し、液温20℃の条件で、アルカリ(A)と水(C)の均一溶解液を20g/分の速度で滴下した。滴下後の操作は実施例1と同様に行った。結果を表2に示す。
Comparative Examples 4 and 5
Add acetone (B) and raw oil / fat composition (E1) to a 300 mL round bottom flask, stir uniformly at 400 r / min, and uniformly dissolve alkali (A) and water (C) at a liquid temperature of 20 ° C. The liquid was added dropwise at a rate of 20 g / min. The operation after dropping was performed in the same manner as in Example 1. The results are shown in Table 2.

Figure 0004568565
Figure 0004568565

表2から明らかなように、油脂組成物に有機溶剤を添加した後にアルカリ剤及び水を添加した場合(比較例4及び5)は、脂肪酸塩中に油脂組成物が巻き込まれ、濾過による脂肪酸塩の分離が困難であった。また、アルカリ剤、有機溶剤及び水のいずれか1つを用いない場合(比較例1〜3)は、比較例1では、脂肪酸塩中に油脂組成物が巻き込まれ、濾過による脂肪酸塩の分離が困難であり、比較例2では、粘張な脂肪酸塩が生成し、濾過による脂肪酸塩の分離が極めて困難であり、比較例3では、脂肪酸塩が形成され難く、濾過回収後の油脂組成物中の脂肪酸除去率が低く、好ましい効果は得られなかった。   As is apparent from Table 2, when an alkali agent and water are added after adding an organic solvent to the oil and fat composition (Comparative Examples 4 and 5), the oil and fat composition is involved in the fatty acid salt, and the fatty acid salt by filtration It was difficult to separate. Moreover, when not using any one of an alkali agent, an organic solvent, and water (Comparative Examples 1-3), in Comparative Example 1, the fat and oil composition is involved in the fatty acid salt, and separation of the fatty acid salt by filtration is performed. In Comparative Example 2, a viscous fatty acid salt is formed, and separation of the fatty acid salt by filtration is extremely difficult. In Comparative Example 3, the fatty acid salt is difficult to be formed, and in the oil and fat composition after filtration recovery The fatty acid removal rate was low, and a favorable effect was not obtained.

これに対し、本発明方法によれば、濾過性の良好な沈殿が生成するため濾過速度が高く、また遊離脂肪酸の除去効率も極めて高かった。   On the other hand, according to the method of the present invention, a precipitate having good filterability was generated, so that the filtration rate was high and the removal efficiency of free fatty acids was extremely high.

Claims (3)

予め調製された、(A)アルカリ金属もしくはアルカリ土類金属の水酸化物及び炭酸塩から選ばれるアルカリ剤、(B)エタノール及びアセトンから選ばれる有機溶剤、並びに(C)水を含有する調製液(D)に、遊離脂肪酸を含有する油脂組成物を混合し、次いで当該混合液を攪拌後固液分離する、油脂組成物から遊離脂肪酸が低減された油脂の製造方法であって、
調製液(D)中の(A)アルカリ剤の含有量が油脂組成物中に含有される遊離脂肪酸に対して150〜500モル%で、(B)有機溶剤/(C)水の質量比が2〜100であり、油脂組成物100質量部に対して調製液(D)を100〜800質量部用いる、油脂組成物から遊離脂肪酸が低減された油脂の製造方法。
(A) Alkaline agent selected from alkali metal or alkaline earth metal hydroxide and carbonate , (B) Organic solvent selected from ethanol and acetone , and (C) Preparation solution containing water In (D), a fat and oil composition containing free fatty acids is mixed, and then the mixture is stirred and then solid-liquid separated .
Content of (A) alkaline agent in preparation liquid (D) is 150-500 mol% with respect to the free fatty acid contained in fats and oils composition, and the mass ratio of (B) organic solvent / (C) water is. It is 2-100, The manufacturing method of the fats and oils from which the free fatty acid was reduced from the oil-fat composition which uses 100-800 mass parts of preparation liquids (D) with respect to 100 mass parts of oil-fat compositions.
調製液(D)が、(A)アルカリ金属もしくはアルカリ土類金属の水酸化物及び炭酸塩から選ばれるアルカリ剤並びに(C)水を含有する液と、(B)エタノール及びアセトンから選ばれる有機溶剤とを混合することにより調製されるものである請求項1記載の油脂の製造方法。 Organic preparation (D) is selected from liquid and, (B) ethanol and acetone containing an alkali agent and (C) water selected from (A) an alkali metal or alkaline earth metal hydroxides and carbonates 2. The method for producing fats and oils according to claim 1, which is prepared by mixing with a solvent. 油脂組成物中の遊離脂肪酸含量が20〜80質量%である、請求項1又は2記載の油脂の製造方法。  The manufacturing method of the fats and oils of Claim 1 or 2 whose free fatty acid content in a fat and oil composition is 20-80 mass%.
JP2004271690A 2004-09-17 2004-09-17 Method for producing fats and oils with reduced free fatty acids Expired - Fee Related JP4568565B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2004271690A JP4568565B2 (en) 2004-09-17 2004-09-17 Method for producing fats and oils with reduced free fatty acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2004271690A JP4568565B2 (en) 2004-09-17 2004-09-17 Method for producing fats and oils with reduced free fatty acids

Publications (2)

Publication Number Publication Date
JP2006083343A JP2006083343A (en) 2006-03-30
JP4568565B2 true JP4568565B2 (en) 2010-10-27

Family

ID=36162114

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2004271690A Expired - Fee Related JP4568565B2 (en) 2004-09-17 2004-09-17 Method for producing fats and oils with reduced free fatty acids

Country Status (1)

Country Link
JP (1) JP4568565B2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101285828B1 (en) 2012-08-13 2013-07-12 주식회사 엠알아이 Method for pre-treating a biodiesel feedstock oil

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6316590B2 (en) * 2010-09-13 2018-04-25 パルスガード アグシャセルスガーッブPalsgaard A/S Refined vegetable oil and method for producing the same
EP3694962B1 (en) * 2017-10-13 2023-12-13 GlycosBio Inc. Processed oil comprising monoacylglycerides

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50103506A (en) * 1974-01-23 1975-08-15
JPS62167397A (en) * 1986-01-17 1987-07-23 オリザ油化株式会社 Separation of fatty acid from crude oils and fats
JPH01207258A (en) * 1988-02-12 1989-08-21 Japanese Res & Dev Assoc Bio Reactor Syst Food Ind Method for removing acid
JPH04266998A (en) * 1990-10-23 1992-09-22 Soc Prod Nestle Sa Method for obtaining unsaponifiable compound from wax
JPH04370195A (en) * 1991-06-20 1992-12-22 Asahi Denka Kogyo Kk Method for deacidifying oil and fat
JP2002212586A (en) * 2001-01-19 2002-07-31 Kanegafuchi Chem Ind Co Ltd Method for refining oil and fat
JP2004115711A (en) * 2002-09-27 2004-04-15 Miyoshi Oil & Fat Co Ltd Method for refining waste edible oil

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50103506A (en) * 1974-01-23 1975-08-15
JPS62167397A (en) * 1986-01-17 1987-07-23 オリザ油化株式会社 Separation of fatty acid from crude oils and fats
JPH01207258A (en) * 1988-02-12 1989-08-21 Japanese Res & Dev Assoc Bio Reactor Syst Food Ind Method for removing acid
JPH04266998A (en) * 1990-10-23 1992-09-22 Soc Prod Nestle Sa Method for obtaining unsaponifiable compound from wax
JPH04370195A (en) * 1991-06-20 1992-12-22 Asahi Denka Kogyo Kk Method for deacidifying oil and fat
JP2002212586A (en) * 2001-01-19 2002-07-31 Kanegafuchi Chem Ind Co Ltd Method for refining oil and fat
JP2004115711A (en) * 2002-09-27 2004-04-15 Miyoshi Oil & Fat Co Ltd Method for refining waste edible oil

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101285828B1 (en) 2012-08-13 2013-07-12 주식회사 엠알아이 Method for pre-treating a biodiesel feedstock oil

Also Published As

Publication number Publication date
JP2006083343A (en) 2006-03-30

Similar Documents

Publication Publication Date Title
RU2287519C2 (en) Fatty acid lower alkyl ester production process
JP4872047B2 (en) Method for producing alkyl ester using glycerin
DK2114851T3 (en) PROCEDURE FOR SEPARATING Saturated AND Saturated FAT ACIDS
JPWO2010126136A1 (en) Method for inhibiting the formation of chloropropanols and their forming substances in glyceride oils
JP2005350632A (en) Method for producing biodiesel fuel
JP2006508148A (en) Alkyl ester production method
WO2009020406A1 (en) Methods of making lipid substances, lipid substances made thereby and uses thereof
HU214203B (en) Process for preparing lower alcohol fatty acid esters
JP4374219B2 (en) Chemical recycling method for waste oil
US8440847B2 (en) Method of converting free fatty acid (FFA) from oil to methyl ester
JP5486589B2 (en) Method and system for producing fatty acid alkyl ester
KR101374629B1 (en) Method for preparing high-purified unsaturated fatty acids using waste animal and vegetable oil
JP4568565B2 (en) Method for producing fats and oils with reduced free fatty acids
JP2005350630A (en) Technique for producing low-exhaust type biodiesel fuel
JP3934630B2 (en) Process for producing biodiesel fuel from acidic oils and fats
JP3839791B2 (en) Fatty acid production method
TWI233448B (en) A method for producing a fatty acid
JP2012224797A (en) Method for producing transesterified fat-and-oil
JP2009161776A (en) Method for producing biodiesel fuel and device for producing the same
WO2019237328A1 (en) Method for preparing biodiesel from kitchen waste
JP6641063B2 (en) Method for removing monoglycerides in biodiesel
JP3656863B2 (en) Process for producing fats and oils having a high content of highly unsaturated fatty acid residues
JPS59172596A (en) Purified fish oil and manufacture
WO2013076813A1 (en) Method for producing biodiesel fuel
JP2010189292A (en) Method for purifying fatty acid alkyl ester

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20070123

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20100318

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20100330

A521 Written amendment

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20100527

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20100803

A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20100809

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20130813

Year of fee payment: 3

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

LAPS Cancellation because of no payment of annual fees