JPS59213798A - Separation of glycerol esters - Google Patents
Separation of glycerol estersInfo
- Publication number
- JPS59213798A JPS59213798A JP58088166A JP8816683A JPS59213798A JP S59213798 A JPS59213798 A JP S59213798A JP 58088166 A JP58088166 A JP 58088166A JP 8816683 A JP8816683 A JP 8816683A JP S59213798 A JPS59213798 A JP S59213798A
- Authority
- JP
- Japan
- Prior art keywords
- glycerol esters
- solvent
- fatty acids
- separating
- oil
- 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.)
- Granted
Links
- 150000002314 glycerols Chemical class 0.000 title claims description 39
- 238000000926 separation method Methods 0.000 title claims description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 40
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 38
- 229930195729 fatty acid Natural products 0.000 claims description 38
- 239000000194 fatty acid Substances 0.000 claims description 38
- 150000004665 fatty acids Chemical class 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 31
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 20
- 238000002844 melting Methods 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- -1 first Chemical class 0.000 claims description 15
- 239000000706 filtrate Substances 0.000 claims description 13
- 238000005194 fractionation Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 7
- 239000012454 non-polar solvent Substances 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 4
- 239000003921 oil Substances 0.000 description 33
- 235000019198 oils Nutrition 0.000 description 33
- 239000002994 raw material Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 235000019879 cocoa butter substitute Nutrition 0.000 description 7
- 238000005809 transesterification reaction Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 5
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- 102000004882 Lipase Human genes 0.000 description 4
- 108090001060 Lipase Proteins 0.000 description 4
- 239000004367 Lipase Substances 0.000 description 4
- 235000019421 lipase Nutrition 0.000 description 4
- 244000299461 Theobroma cacao Species 0.000 description 3
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 3
- 241001135917 Vitellaria paradoxa Species 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 210000002683 foot Anatomy 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229940057910 shea butter Drugs 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 241000235527 Rhizopus Species 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 2
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 235000001046 cacaotero Nutrition 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 244000062730 Melissa officinalis Species 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】 本発明はグリセロールエステル類の分離方法に関する。[Detailed description of the invention] The present invention relates to a method for separating glycerol esters.
さらに詳しくは、主成分が、脂肪酸とグリセロールエス
テル類からなる混合物より、中融点部グリセロールエス
テルを分離する方法に関する。More specifically, the present invention relates to a method for separating intermediate melting point glycerol esters from a mixture whose main components are fatty acids and glycerol esters.
酸価が異常に高くなった油脂、あるいは脂肪酸とグリセ
ロールエステルのエステル基交換反応物などのように、
主たる成分が、脂肪酸とグリセロールエステル類からな
る混合物を脂肪酸とグリセロールエステル類に分離する
工業的方法には、アルカリ脱酸方法及び水蒸気蒸留方法
等が知られている。アルカリ脱酸方法は、脂肪酸含量が
比較的低い場合に適用出来るが、脂肪酸含量が高い場合
にはグリセロールエステル類の石鹸混合物フーツへのロ
スが大きく適用出来ない。また、水蒸気蒸留方法は、グ
リセロールエステル及び／あるいは脂肪酸間のエステル
交換が起こり、グリセロールエステルの組成が変化する
ため、望ましいグリセロールエステル組成物を得ること
が出来ない。また脂肪酸とグリセロールエステル類の実
験室的な分離方法としては、カラムクロマトグー・フィ
ーがアリ、この力比Ｉ“・ 、グリセロールエステル
の組成変化を起こすことなく脂肪酸とグリセロールエス
テル類の分離を行うことが出来る。しかし該カラムクロ
マトグラフィーでは、工程コストが高く工業的に通用す
ることが不可能である。一本発明の目的は、主成分が脂
肪酸とグリセロールエステル類からなる混合物より、グ
リセロールエステル類の組成変化を起こすことなく脂肪
酸とグリセロールエステル類とを分離する方法を提供す
ることにある。また、それと同時にグリセロールエステ
ル類より高品質の中融点部グリセロールジエステルを分
離する方法を提供することにある。Such as oils and fats with abnormally high acid values, or transesterification products of fatty acids and glycerol esters,
As industrial methods for separating a mixture whose main components are fatty acids and glycerol esters into fatty acids and glycerol esters, alkali deoxidation methods, steam distillation methods, and the like are known. The alkaline deoxidation method can be applied when the fatty acid content is relatively low, but cannot be applied when the fatty acid content is high because of the large loss of glycerol esters to the soap mixture foot. Further, in the steam distillation method, transesterification occurs between glycerol esters and/or fatty acids, and the composition of the glycerol esters changes, so that a desirable glycerol ester composition cannot be obtained. In addition, as a laboratory method for separating fatty acids and glycerol esters, column chromatography is the best method.With this power ratio I'', it is possible to separate fatty acids and glycerol esters without causing a change in the composition of the glycerol esters. However, the process cost of column chromatography is high and it is impossible to apply it industrially.An object of the present invention is to reduce the amount of glycerol esters from a mixture whose main components are fatty acids and glycerol esters. The object of the present invention is to provide a method for separating fatty acids and glycerol esters without causing a change in composition.At the same time, it is an object to provide a method for separating a medium-melting point glycerol diester of higher quality than the glycerol esters.
即ち、本発明のグリセロールエステル類の分離方法は、
主脂肪酸とグリセロールエステル類からなる混合物より
、先ず、溶剤（Ａ）による溶剤分別により脂肪酸及び高
融点部グリセロールエステルを結晶部として分離し、得
られた濾液部に液状油物質（Ｂ）を加えアルカリ脱酸に
より残余脂肪酸除去した後、このアルカリ脱酸油を溶剤
（Ｃ）による溶剤分別により、中融点部グリセロールエ
ステルを結晶部として、低融点部グリセロールエステル
を濾液部として分離することを特徴とするものである。That is, the method for separating glycerol esters of the present invention is as follows:
From a mixture consisting of main fatty acids and glycerol esters, fatty acids and high melting point glycerol esters are first separated as crystal parts by solvent fractionation using a solvent (A), and a liquid oil substance (B) is added to the obtained filtrate part to make an alkali. After removing residual fatty acids by deacidification, this alkali-deoxidized oil is separated by solvent fractionation using a solvent (C) to separate medium-melting point glycerol esters as a crystal part and low-melting point glycerol esters as a filtrate part. It is something.
以下に本発明のグリセロールエステル類の分離方法につ
いて詳述する。The method for separating glycerol esters of the present invention will be described in detail below.
前記溶剤（Ａ）としては、脂肪酸と高融点部グリセロー
ルエステルをより選択的に結晶化させるものが望ましく
、非極性溶剤が有効に使用できる。The solvent (A) is preferably one that selectively crystallizes fatty acids and high melting point glycerol esters, and nonpolar solvents can be used effectively.
そのような有効に使用出来る非極性溶剤としては、ｎ−
ヘキサン、イソヘキサン、シクロヘキサン、ｎ−ヘプタ
クン、ｎ−オクタン、イソオクタン等が挙げられるが、
特にｎ−ヘキサン、イソヘキサン（混合物）等のへキサ
ンがより有効に使用出来る。As such a non-polar solvent that can be used effectively, n-
Examples include hexane, isohexane, cyclohexane, n-heptacune, n-octane, isooctane, etc.
In particular, hexane such as n-hexane and isohexane (mixture) can be used more effectively.
前記液状油物質（Ｂ）としては、常温で液体の油状物質
が有効に使用できるが、特に、常温で液状のグリセロー
ルエステル、例えば、大豆油、コーン油、ナタネ油、綿
実サラダ油、あるいは、パーム油、マウア脂、ザル脂、
シア脂等がより有効に使用出来る。As the liquid oil substance (B), oil substances that are liquid at room temperature can be effectively used, but in particular, glycerol esters that are liquid at room temperature, such as soybean oil, corn oil, rapeseed oil, cottonseed salad oil, or palm oil. Oil, maua fat, colander fat,
Shea butter etc. can be used more effectively.
前記溶剤（Ｃ）としては、極性溶剤、非極性溶剤ともに
有効に使用出来るが、極性溶剤が好ましく、特に、メチ
ルエチルケトン、アセトン、メチルエチルケトンあるい
はアセトンと水の混合物、メチルエチルケトンあるいは
アセトンとアルコールの混合物、ヘキサンとアルコール
の混合物等がより有効に使用出来る。これらのなかでも
特にアセトンが簡便に且つ有効に使用出来る。As the solvent (C), both polar and non-polar solvents can be effectively used, but polar solvents are preferred, and in particular, methyl ethyl ketone, acetone, methyl ethyl ketone or a mixture of acetone and water, methyl ethyl ketone or a mixture of acetone and alcohol, hexane and A mixture of alcohols can be used more effectively. Among these, acetone can be used particularly easily and effectively.
溶剤分別に用いる溶剤としては、効果が同一であれば、
二種以上の混合系溶剤よりも、単一溶剤の方が回収系が
単純化されるという点でより望ましい。As for the solvent used for solvent separation, if the effect is the same,
A single solvent is more desirable than a mixed solvent of two or more solvents because it simplifies the recovery system.
溶剤（Ａ）の使用量は原料（主成分が、脂肪酸とグリセ
ロールエステル類からなる混合物）１重量部に対して２
重量部から８重量部が望ましく、より望ましくは、３重
量部から５重量部である。The amount of solvent (A) used is 2 parts by weight of the raw material (a mixture whose main components are fatty acids and glycerol esters).
It is preferably from 8 parts by weight, more preferably from 3 parts by weight to 5 parts by weight.
このときの分別温度は溶剤の種類及びその使用量によっ
て異なるが、ヘキサンの場合、−５°Ｃから５℃が望ま
しい。この溶剤分別で得られた濾液部１重量部に対して
、液状油物質（Ｂ）０．２重量部から２重量部添加する
ことにより、効果的にアルカリ脱酸することが出来る。The separation temperature at this time varies depending on the type of solvent and the amount used, but in the case of hexane, it is preferably -5°C to 5°C. By adding 0.2 to 2 parts by weight of the liquid oil substance (B) to 1 part by weight of the filtrate obtained by this solvent fractionation, effective alkaline deoxidation can be achieved.
また溶剤（Ｃ）の使用量はアルカリ脱酸油１重量部に対
して１重量部から１０重量部が望ましく、より望ましく
は１．５重量部から４重量部である。The amount of solvent (C) used is preferably 1 to 10 parts by weight, more preferably 1.5 to 4 parts by weight, per 1 part by weight of the alkaline deoxidized oil.
このときの分別温度は溶剤の種類及びその使用量によっ
て異なるが、ヘキサンの場合−１５℃から一５℃、アセ
トンの場合、−５℃から＋２℃が望ましい。The separation temperature at this time varies depending on the type of solvent and the amount used, but is preferably -15°C to -5°C in the case of hexane, and -5°C to +2°C in the case of acetone.
本発明の方法によって得られる中融点部グリセロールエ
ステルは主にカカオバター代用脂として用いられるが、
脂肪酸が多（含まれる混合物より該中融点部グリセロー
ルエステルを分取する際、最も注意しなければならない
ことは、グリセロールエステル間及びグリセロールエス
テルと脂肪酸間のランダムエステル交換を最小限に抑制
することである。その理由は脂肪酸が多く含まれる場合
、工程中にランダムエステル交換が非常に起こりやすく
、グリセロールエステルの組成変化が起こり、従って物
性変化が起こりやすいからである。The intermediate melting point glycerol ester obtained by the method of the present invention is mainly used as a cocoa butter substitute, but
When separating the medium-melting point glycerol ester from a mixture containing a large amount of fatty acids, the most important thing to be careful of is to minimize random transesterification between glycerol esters and between glycerol esters and fatty acids. The reason is that when a large amount of fatty acids is contained, random transesterification is very likely to occur during the process, resulting in a change in the composition of the glycerol ester and, therefore, a change in physical properties.
通常の食用油脂の製造の際には組成変化及び物性変化に
よってそれほど大きな影響を受けないが、カカオバター
代用脂あるいはその原料となる中融点部グリセロールエ
ステルの製造の場合には、−担組成変化つまり物性変化
の起こったものは１．カカオバター代用脂あるいはその
原料として使用出来ない。In the production of ordinary edible fats and oils, compositional changes and changes in physical properties do not have a large effect, but in the production of cocoa butter substitutes or intermediate-melting point glycerol esters that are raw materials for them, changes in carrier composition, i.e. Items with physical property changes are 1. Cannot be used as a cocoa butter substitute or its raw material.
本発明のグリセロールエステル類の分離方法ハ脂肪酸含
量が約２０％以上含有される高酸価のグリセロールエス
テルに有効に適用出来る。このような原料を先ずヘキサ
ンのような非極性溶剤（Ａ）で溶剤分別するのであるが
、この溶剤分別では主に飽和脂肪酸、モノグリセリド、
ジグリセリドおよび高融点トリグリセリド等の成分が結
晶部として除去される。得られた濾液部の脂肪酸含量は
原料の脂肪酸含量の約半分程度になる。残余の脂肪酸の
主体は不飽和脂肪酸である。この濾液部に液状油物質（
Ｂ）を添加してアルカリ脱酸することにより、中融点グ
リセロールエステルのフーツのロスを低減させることが
できる。またこのアルカリ脱酸では残余のモノグリセリ
ド、ジグリセリドが除去される。この脱酸油を必要に応
じて湯洗および／あるいは漂白し、さらに溶剤（Ｃ）で
溶剤分別することにより、結晶部に品質良好な中融点部
グリセロールエステルを分離分取することができる。咳
中融点部グリセロールエステルは漂白および脱臭するこ
とにより、カカオバター代用脂あるいはカカオバター代
用脂原料として使用することが出来る。The method for separating glycerol esters of the present invention can be effectively applied to glycerol esters with a high acid value containing about 20% or more of fatty acid content. These raw materials are first subjected to solvent fractionation using a non-polar solvent (A) such as hexane, but in this solvent fractionation, saturated fatty acids, monoglycerides,
Components such as diglycerides and high melting point triglycerides are removed as crystalline parts. The fatty acid content of the obtained filtrate is about half of the fatty acid content of the raw material. The remaining fatty acids are mainly unsaturated fatty acids. This filtrate part contains a liquid oil substance (
By adding B) and performing alkali deoxidation, loss of medium melting point glycerol ester foots can be reduced. Further, in this alkaline deoxidation, residual monoglycerides and diglycerides are removed. By washing this deoxidized oil with hot water and/or bleaching it as necessary, and further solvent fractionating it with a solvent (C), it is possible to separate and fractionate the intermediate melting point glycerol ester of good quality in the crystalline part. By bleaching and deodorizing the cough melting point glycerol ester, it can be used as a cocoa butter substitute or a raw material for a cocoa butter substitute.
以下に実施例を示し、本発明をより詳細に説明する。EXAMPLES The present invention will be explained in more detail with reference to Examples below.
実施例１
ステアリン酸９部とサル脂軟部油１０部をヘキサン溶媒
中でリゾプスデレマー由来のリパーゼによりエステル基
交換反応を行い、酸価９７．７（脂肪酸含量４９％）の
反応油を得た。この反応油のシリル化物のガスクロマト
グラフィーによる組成分析（相対感度考慮していない）
では、脂肪酸５０．２％、ジグリセリド６．１％、１−
ジグリセリド４３．４％であった。この反応油１部にヘ
キサン４部を加え、加熱溶解した後、４℃まで冷却し、
結晶部と濾液部に濾別した。濾液部の収率は６０．７％
、酸価５３．２（脂肪酸含量的２６．６％）であった。Example 1 A transesterification reaction was performed on 9 parts of stearic acid and 10 parts of monkey fat soft part oil in a hexane solvent using lipase derived from Rhizopus deremer to obtain a reaction oil with an acid value of 97.7 (fatty acid content: 49%). Composition analysis of the silylated product of this reaction oil by gas chromatography (relative sensitivity not taken into account)
So, fatty acid 50.2%, diglyceride 6.1%, 1-
The diglyceride content was 43.4%. Add 4 parts of hexane to 1 part of this reaction oil, heat and dissolve, then cool to 4°C.
It was separated by filtration into a crystal part and a filtrate part. Yield of filtrate part is 60.7%
The acid value was 53.2 (fatty acid content 26.6%).
この濾液部のシリル化物のガスクロマトグラフィーによ
る組成分析（相対感度考慮していない）では、脂肪酸３
２．４％、ジグリセリド６．０％、トリグリセリド６１
．６％であった。この濾液部６部に液状油４部を混合し
、アルカリ脱酸を行った。脱酸油のシリル化物のガスク
ロマトグラフィーによる組成分析（相対感度考慮してい
ない）では、脂肪酸０％、ジグリセリド６．１％、トリ
グリセリド９３．９％であった。この脱酸油１部にｎ−
へキサン１．７部を混合し、加熱溶解した後冷却し、−
７°Ｃで溶剤分別を行った。結晶部の収率は、３１．５
％であり、得られた結晶部の性状を調べたところカカオ
バク−代用脂の原料として非常に良好であった。In the compositional analysis of the silylated product in this filtrate by gas chromatography (relative sensitivity not taken into account), fatty acid 3
2.4%, diglyceride 6.0%, triglyceride 61
．． It was 6%. 4 parts of liquid oil was mixed with 6 parts of this filtrate, and alkaline deacidification was performed. Compositional analysis of the silylated product of the deoxidized oil by gas chromatography (relative sensitivity not taken into consideration) revealed that it contained 0% fatty acids, 6.1% diglycerides, and 93.9% triglycerides. One part of this deoxidized oil contains n-
1.7 parts of hexane was mixed, heated and dissolved, and then cooled, -
Solvent fractionation was performed at 7°C. The yield of crystal part is 31.5
%, and when the properties of the obtained crystalline portion were examined, it was found to be very good as a raw material for cacao bak substitute fat.
実施例２
実施例１で得た脱酸油１部にアセトン２．２部を混合し
、加熱熔解した後Ｏ℃で溶剤分別を行った。結晶部の収
率は２８．７％であり、得られた結晶部の性状を開べた
ところ、カカオバク−代用脂の原料として非常に良好で
あった。特にチョコレートのテンパリング作業性の良好
な原料であった。Example 2 1 part of the deoxidized oil obtained in Example 1 was mixed with 2.2 parts of acetone, heated and melted, and then subjected to solvent fractionation at 0°C. The yield of the crystalline part was 28.7%, and when the properties of the obtained crystalline part were examined, it was found to be very good as a raw material for cacao bak substitute fat. It was a raw material with particularly good tempering workability for chocolate.
実施例３
ステアリン酸９部とバーム軟部油１０部をヘキサン溶媒
中でリゾプスデレマー由来のリパーゼによりエステル基
交換反応を行い、酸価９６．２の（脂肪酸含量４８％）
の反応油を得た。この反応油のシリル化物のガスクロマ
トグラフィーによる組成分析（相対感度考慮していない
）では、脂肪酸５７．４％、ジグリセリド５．６％、ト
リグリセリド３６．８％であった。この反応油１部にヘ
キサン４部を加え、加熱溶解した後、２℃で分別した。Example 3 9 parts of stearic acid and 10 parts of balm soft part oil were subjected to a transesterification reaction using lipase derived from Rhizopus delemer in a hexane solvent to obtain an acid value of 96.2 (fatty acid content: 48%).
A reaction oil was obtained. Compositional analysis of the silylated product of this reaction oil by gas chromatography (relative sensitivity not taken into consideration) revealed that it was 57.4% fatty acids, 5.6% diglycerides, and 36.8% triglycerides. 4 parts of hexane was added to 1 part of this reaction oil, heated and dissolved, and then fractionated at 2°C.
濾液部の収率は６１．３％、酸価５Ｂ、４（脂肪酸含量
約２９．２％）であった。この濾液部のシリル化物のガ
スクロマトグラフィーによる組成分析（相対感度考慮し
ていない）では、脂肪酸３３．０％、ジグリセリド６．
１％、トリグリセリド６０．９％であフた。この濾液部
５部に液状油５部を混合し、アルカリ脱酸を行った。脱
酸油のシリル化物のガスクロマ５トゲラフイーによる組
成分析（相対感度考慮していない）では、脂肪酸０％、
ジグリセリド３．９％、トリグリセリド９６．１％であ
った。この脱酸油１部にｎ−ヘキサン１．５部を混合し
、加熱熔解した後冷却し、−７℃で溶剤分別を行った。The yield of the filtrate portion was 61.3%, and the acid value was 5B.4 (fatty acid content: about 29.2%). Compositional analysis of the silylated product in this filtrate by gas chromatography (relative sensitivity not taken into account) revealed that fatty acids were 33.0% and diglycerides were 6.0%.
1%, triglyceride 60.9%. 5 parts of liquid oil was mixed with 5 parts of this filtrate, and alkaline deacidification was performed. Composition analysis of silylated deoxidized oil using Gas Chroma 5 Togelafy (relative sensitivity not taken into account) revealed that fatty acids were 0%,
Diglyceride was 3.9% and triglyceride was 96.1%. 1.5 parts of n-hexane was mixed with 1 part of this deoxidized oil, heated and melted, then cooled, and solvent fractionation was performed at -7°C.
結晶部の収率は、１９．１％であり、得られた結晶部の
性状を調べたところカカオバター代用脂の原料として非
常に良好であった。The yield of the crystalline portion was 19.1%, and when the properties of the obtained crystalline portion were examined, it was found to be very good as a raw material for a cocoa butter substitute.
比較例１
実施例１の、リパーゼによるエステル基交換反応の反応
油（酸価９７．７ ）を水蒸気蒸留法により脱酸した。Comparative Example 1 The reaction oil (acid value 97.7) from the transesterification reaction using lipase in Example 1 was deoxidized by steam distillation.
この方法は、一般にフィジカルリファイニングと呼ばれ
る脱酸方法である。この脱酸油は酸価１２，８であった
。この脱酸油をさらに通常のアルカリ脱酸方法で脱酸し
た。このアルカリ脱酸油を二段溶剤分別にかけ、中融点
部グリセロールエステルを分取したが、カカオバター代
用脂としては使用し得ないものであった。This method is a deoxidizing method generally called physical refining. This deacidified oil had an acid value of 12.8. This deoxidized oil was further deoxidized by a conventional alkaline deoxidation method. This alkali-deoxidized oil was subjected to two-stage solvent fractionation to separate the intermediate melting point glycerol ester, but it could not be used as a cocoa butter substitute.
比較例２
実施例１の、リパーゼによるエステ）Ｉ＜基交換反応の
反応油（酸価９７．７ ＞を通常のアルカリ脱酸方法で
脱酸したが、中性油がフーツから分離しなかった。Comparative Example 2 The reaction oil (acid value 97.7) from the group exchange reaction (Esthetics using lipase) in Example 1 was deacidified by a normal alkaline deacidification method, but the neutral oil was not separated from the foots. .
手続補正書
昭和５８年６月２９日
特許庁長官 若 杉 和 夫 殿
１、事件の表示
特願昭５８−８８１６６号
２、発明の名称
グリセロールエステル類の分離方法
３、補正をする者
事件との関係 特許出願人
（０３８）旭電化工業株式会社
４、代理人
東京都港区赤坂九丁目６番２９号
パシフィック乃木坂６０１号
自発補正（出願口から１年３ケ月以内の補正）６、補正
の対象
７、補正の内容
（１１第４頁８行の「主脂肪酸」を「主に脂肪酸」と補
正。Procedural amendment June 29, 1980 Kazuo Wakasugi, Director General of the Patent Office1, Indication of the case, Patent Application No. 1988-881662, Title of the invention: Method for separating glycerol esters3, Person making the amendment Related Patent applicant (038) Asahi Denka Kogyo Co., Ltd. 4, Agent Pacific Nogizaka 601, 6-29 Akasaka 9-chome, Minato-ku, Tokyo Voluntary amendment (amendment within 1 year and 3 months from filing of application) 6. Subject of amendment 7. Contents of correction ("Main fatty acids" on page 4, line 8 of 11 has been corrected to "mainly fatty acids."
（２）第５頁５行の「ｎ−ヘプタタン」を「ｎ−へブタ
ン」と補正。(2) Corrected "n-heptatan" on page 5, line 5 to "n-hebutane."
（３）第５頁１３行の「シア脂等が」を「シア脂等の分
別軟部油が」と補正。(3) On page 5, line 13, "shea butter, etc." was corrected to "fractionated soft part oil such as shea butter."
以上that's all
Claims (6)
なる混合物より、中融点部グリセロールエステルを分離
する方法に於いて、先ず、溶剤（Ａ）による溶剤分別に
より、脂肪酸及び高融点部グリセロールエステルを結晶
部として分離し、次に、得られた濾液部に液状油物質（
Ｂ）を加えアルカリ脱酸により残余脂肪酸を除去した後
、このアルカリ脱酸油を溶剤（Ｃ）による溶剤分別によ
り、中融点部グリセロールエステルを結晶部として、低
融点部グリセロールエステルを濾液部として分離するこ
とを特徴とするグリセロールエステル類の分離方法。(1) In the method of separating medium-melting point glycerol esters from a mixture whose main components are fatty acids and glycerol esters, first, fatty acids and high-melting point glycerol esters are crystallized by solvent fractionation using solvent (A). The liquid oil substance (
After adding B) and removing residual fatty acids by alkaline deoxidation, this alkaline deoxidized oil was separated by solvent fractionation using solvent (C) to separate the medium melting point glycerol ester as a crystal part and the low melting point glycerol ester as a filtrate part. A method for separating glycerol esters.
特許請求の範囲第（１）項記載のグリセロールエステル
類の分離方法。(2) The method for separating glycerol esters according to claim (1), wherein the solvent (A) is a nonpolar solvent.
テルであることを特徴とする特許請求の範囲第（１）又
は（２）項記載のグリセロールエステル類の分離方法。(3) The method for separating glycerol esters according to claim (1) or (2), wherein the liquid oil substance (B') is a liquid glycerol ester.
許請求の範囲第（１）〜（３）項の何れかに記載のグリ
セロールエステル類の分離７ｊ［。(4) Separation 7j of glycerol esters according to any one of claims (1) to (3), wherein the solvent (C) is a polar solvent.
許請求の範囲第（２）項記載のグリセロールエステル類
の分離方法。(5) The method for separating glycerol esters according to claim (2), characterized in that a non-polar solvent or hexane is used.
請求の範囲第（４）項記載のグリセロールエステル類の
分離方法。(6) The method for separating glycerol esters according to claim (4), wherein the polar solvent is acetone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58088166A JPS59213798A (en) | 1983-05-19 | 1983-05-19 | Separation of glycerol esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58088166A JPS59213798A (en) | 1983-05-19 | 1983-05-19 | Separation of glycerol esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59213798A true JPS59213798A (en) | 1984-12-03 |
| JPH0471119B2 JPH0471119B2 (en) | 1992-11-12 |
Family
ID=13935332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58088166A Granted JPS59213798A (en) | 1983-05-19 | 1983-05-19 | Separation of glycerol esters |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59213798A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003057807A3 (en) * | 2001-12-31 | 2003-10-30 | Cargill Inc | Process for oil extraction |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4834907A (en) * | 1971-09-06 | 1973-05-23 | ||
| JPS56127694A (en) * | 1980-03-12 | 1981-10-06 | Asahi Denka Kogyo Kk | Classification of sulseed fat |
| JPS57212299A (en) * | 1981-06-22 | 1982-12-27 | Asahi Denka Kogyo Kk | Fractionation of oil and fat |
-
1983
- 1983-05-19 JP JP58088166A patent/JPS59213798A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4834907A (en) * | 1971-09-06 | 1973-05-23 | ||
| JPS56127694A (en) * | 1980-03-12 | 1981-10-06 | Asahi Denka Kogyo Kk | Classification of sulseed fat |
| JPS57212299A (en) * | 1981-06-22 | 1982-12-27 | Asahi Denka Kogyo Kk | Fractionation of oil and fat |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003057807A3 (en) * | 2001-12-31 | 2003-10-30 | Cargill Inc | Process for oil extraction |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0471119B2 (en) | 1992-11-12 |
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