JPS61179299A - Recovery of hard butter from vegetable fat - Google Patents
Recovery of hard butter from vegetable fatInfo
- Publication number
- JPS61179299A JPS61179299A JP60285955A JP28595585A JPS61179299A JP S61179299 A JPS61179299 A JP S61179299A JP 60285955 A JP60285955 A JP 60285955A JP 28595585 A JP28595585 A JP 28595585A JP S61179299 A JPS61179299 A JP S61179299A
- Authority
- JP
- Japan
- Prior art keywords
- glycerides
- fraction
- transesterification
- fractionation
- glyceride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- 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
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
Landscapes
- Chemical & Material Sciences (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 Chemistry (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は硬質バターおよび食用脂肪からのその製造に関
する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to hard butter and its production from edible fats.
チョコレート脂肪およびココアバターを含む他の硬質バ
ター組成物の食味性は、対称ジ飽和トリグリセリｒ１
主としてパルミチン酸およびステアリン酸の２−オレイ
ルグリセリドの高割合の存在に帰せられる。この高価な
脂肪の代替物として提示された各種代替脂肪は同様にこ
れらのトリグリセリドを多少なりとも実質量含む。これ
らの別の起源からのココアバター代替物およびエキステ
ンダー脂肪の製造方法は一般に分画工程を含み、この工
程ではこれらの一層貴重なグリセＩＪ Ｐは溶融属性が
あまり望ましくない他のグリセリド、特に分離すること
ができるトリ飽和グリセリドおよびモノ−飽和およびト
リー不飽和トリグリセリド。The palatability of chocolate fat and other hard butter compositions containing cocoa butter is
This is mainly attributed to the presence of a high proportion of 2-oleylglycerides of palmitic and stearic acids. The various alternative fats proposed as replacements for this expensive fat likewise contain more or less substantial amounts of these triglycerides. Processes for producing cocoa butter substitutes and extender fats from these alternative sources generally involve a fractionation step in which these more valuable glycerides are separated from other glycerides, particularly those with less desirable melting properties. tri-saturated and mono-saturated and tri-unsaturated triglycerides.
又非対称ジ飽和グリセリドから分離される。分離は特に
アセトン又はヘキサンのような溶媒から分画結晶により
通例性なわれる。一層高度の飽和グリセリドは高−溶融
又はステアリンフラクション中に除去され、一層高度の
不飽和グリセリドは低−溶融又はオレインフラクション
中に除去される。It is also separated from asymmetric disaturated glycerides. Separation is typically accomplished by fractionated crystallization from solvents such as acetone or hexane, among others. The more highly saturated glycerides are removed in the high-melt or stearin fraction and the more highly unsaturated glycerides are removed in the lower-melt or olein fraction.
これらの望ましさの少ないフラクションは初めの脂肪の
半量を構成し、硬質パターフラクションよりはるかに低
いプレミアムに値する。These less desirable fractions make up half of the initial fat and deserve a much lower premium than the hard putter fraction.
酵素再配列触媒を使用する方法による脂肪およびグリセ
リド油のエステル交換は英国特許第１５７７９３３号明
細書に記載されている。ＥＰ第６９５９９号明細書は得
たフラクション中のグリセＩＪ ｙを再配列し、次いで
所望の場合生成物を分画し、特にココアバター代替脂肪
の製造に対し一層高度の対称グリセリドを回収する脂肪
の分画法を開示する。Transesterification of fats and glyceride oils by a method using enzymatic rearrangement catalysts is described in GB 1577933. EP 69599 describes a process for rearranging the glycerin IJ y in the fractions obtained and then fractionating the product if desired to recover a higher degree of symmetrical glycerides, especially for the production of cocoa butter substitute fats. A fractionation method is disclosed.
本発明は植物脂肪から硬質バターの回収方法を供する。The present invention provides a method for recovering hard butter from vegetable fats.
この方法では０１６および０１８脂肪酸の対称ジ飽和ト
リグリセリドの実質量を含む植物脂肪は分画されて少な
くとも一層高度の不飽和、低−溶融オレインフラクショ
ンを分離することによりこのグリセリドを回収し、オレ
インフラクションは、好ましくは植物脂肪から分離され
た高−溶融ステアリンフラクションと再組み合せするこ
とにより実質的に飽和したＣ１６ ／ Ｃ１ｅ ）リグ
リセリド脂肪と混合され、混合物は好ましくはグリセリ
ドの外側位置でのみ、すなわちグリセリドの１−および
、３−位置又はアルファー位置で選択活性である酵素触
媒の存在でエステル交換され、対称ジ飽和グリセリドを
さらに多く得るものである。In this process, a vegetable fat containing a substantial amount of symmetrically disaturated triglycerides of 016 and 018 fatty acids is fractionated to recover this glyceride by separating at least a more highly unsaturated, low-melting olein fraction; , preferably substantially saturated by recombining with a high-melting stearin fraction separated from vegetable fats (C16/C1e) liglyceride fat, the mixture preferably only in the outer positions of the glycerides, i.e. one of the glycerides - and transesterification in the presence of an enzyme catalyst selectively active at the 3- or alpha-positions to yield more symmetrical disaturated glycerides.
オレインフラクションの最大割合は２−位置に不飽和脂
肪酸残基を有するグリセリドから成るので、これらすべ
ては酵素触媒の作用下にエステル交換することにより対
称ジ飽和トリグリセリドに変換することは理論的に可能
である。但し、混和物中に例えばこれと組み合される高
−溶融又はステアリンフラクション中に、一層高度の不
飽和グリセリドとエステル交換を行なうために触媒作用
を受けやすいアルファ又は、６−位置に飽和脂肪酸残基
を含む十分なグリセリドが存在することのみが条件とな
る。例えば、トリ飽和グリセリドはトリー不飽和グリセ
リドとエステル交換し１−飽和シー不飽和グリセリドを
供し、これらは触媒の選択活性の作用下に順次、３−ジ
飽和グリセリドになる。トリ飽和グリセリド自体は非対
称ジ飽和モノー不飽和グリセリｐおよび対称ジー不飽和
グリセリド、すなわち、６−ジ不飽和、２−飽和グリセ
リドに相応して変換する。Since the largest proportion of the olein fraction consists of glycerides with unsaturated fatty acid residues in the 2-position, it is theoretically possible to convert all of these into symmetric disaturated triglycerides by transesterification under the action of enzyme catalysts. be. However, in the admixture, e.g. in the high-melt or stearinic fractions that are combined, saturated fatty acid residues may be present in the alpha or 6-positions which are susceptible to catalysis in order to carry out the transesterification with the more highly unsaturated glycerides. The only condition is that there is sufficient glyceride containing. For example, trisaturated glycerides are transesterified with tri-unsaturated glycerides to provide 1-saturated tri-unsaturated glycerides, which in turn become 3-disaturated glycerides under the action of the selective activity of the catalyst. The trisaturated glycerides themselves are converted correspondingly into asymmetric di-saturated monounsaturated glycerides p and symmetric di-unsaturated glycerides, ie 6-di-unsaturated, 2-saturated glycerides.
エステル交換グリセリドは通例の分画方法におけるよう
に分離し、ココアバター代替脂肪として使用するため対
称ジ飽和グリセリドから本質的に成るフラクションを回
収することができる。特に対称、３−ジー不飽和グリセ
リドを含むエステル交換混合物中の一層高度の不飽和グ
リセリドは低−溶融オレインフラクションを形成する。The transesterified glycerides can be separated as in conventional fractionation methods to recover a fraction consisting essentially of symmetrical disaturated glycerides for use as a cocoa butter substitute fat. In particular, the more highly unsaturated glycerides in the transesterification mixture containing symmetric, 3-di-unsaturated glycerides form a low-melting olein fraction.
任意の未反応トリ飽和グリセリドは必要の場合頂部フラ
クション中に分離され、任意の非対称ジ飽和グリセリド
とさらにエステル交換するために再循環することができ
る。これらは対称ジ飽和フラクションから分離されたス
テアリン又はオレインフラクションのいずれかに現れる
。Any unreacted trisaturated glycerides can be separated into a top fraction if necessary and recycled for further transesterification with any unsymmetrical disaturated glycerides. These appear in either the stearin or olein fractions separated from the symmetric disaturated fractions.
エステル交換グリセリド混合物は別に分画し、又は方法
の分画工程で原料油脂と再組み合せすることができる。The transesterified glyceride mixture can be separately fractionated or recombined with the raw fat in the fractionation step of the process.
分画およびエステル交換ユニットを経る循環に原料油脂
が導入され、この循環から対称ジ飽和グリセリドフラク
ションが除去される連続操作では、原料油脂はいずれか
のユニットに導入され冷体のエステル交換産出物と混合
して最初に分画され、又は対称ジ飽和グリセリドが除去
される再循環エステル交換フラクションと共に最初ニエ
ステル交換することができる。原料油脂が導入され、対
称ジ飽和フラクションが除去される連続操作では、再循
環組成物中にこの扱いにくい物質の形成を回避するため
に対称ジー不飽和グリセリドの浄化が必要である。再配
列触媒、例えば非−選択触媒、２−選択触媒、又は飽和
脂肪酸残基に対しては選択的活性であるが不飽和脂肪酸
残基に対してはそうでない触媒はこの物質を変換しさら
に扱いやすい形に戻すために使用することもできる。連
続操作の特に有利な点はエステル交換は比較的短時間で
あることが必要であり、エステル交換はユニットのそれ
ぞれの通過に対しては十分でなくてよいからである。酵
素エステル交換は一層高潟で使用される無機触媒の作用
下のエステル交換より一般に実質的に遅い。しかし、連
続再循環によりエステル交換工程の滞留時間は必ず平衡
に達しなくても所望グリセリドの収量にかなり、の改良
を供することができるだけの時間で十分である。In continuous operation, where the feedstock is introduced into a circulation through a fractionation and transesterification unit and the symmetrical disaturated glyceride fraction is removed from this circulation, the feedstock is introduced into either unit to form the cold transesterification product. It can be mixed and initially fractionated, or it can be first transesterified with the recycled transesterified fraction from which the symmetrical disaturated glycerides are removed. In continuous operations where feedstock fats and oils are introduced and the symmetric di-saturated fraction is removed, purification of the symmetric di-unsaturated glycerides is necessary to avoid the formation of this recalcitrant material in the recycle composition. Rearrangement catalysts, such as non-selective catalysts, 2-selective catalysts, or catalysts that are selectively active for saturated fatty acid residues but not for unsaturated fatty acid residues, convert and further process this material. It can also be used to return it to a more convenient shape. A particular advantage of continuous operation is that the transesterification requires a relatively short time and transesterification does not have to be sufficient for each pass through the unit. Enzymatic transesterification is generally substantially slower than transesterification under the action of the inorganic catalysts used in Takagata. However, by continuous recirculation, the residence time of the transesterification step is sufficient to provide a significant improvement in the yield of the desired glyceride even if equilibrium is not necessarily reached.
本発明は分画又は再循環せずに、特に次に液状グリセリ
ド油と混和される硬質原料脂肪の製造に対しマーガリン
又は他のエマルジョン食用スジレッド、又はアイスクリ
ームに使用することができる脂肪を供するために再配列
工程から生成物を回収することを含む。The present invention provides a fat that can be used in margarine or other emulsions, edible streak reds, or ice creams, without fractionation or recirculation, especially for the production of hard stock fats which are then blended with liquid glyceride oils. including recovering the product from the rearrangement step.
本発明に従って行なわれる分画工程は許容しうる溶媒、
例えばアセトン、ヘキサン又はニトロパラフィン又は加
圧液体状態の環境ガスを使用する溶媒分画のいずれかＫ
よる通例的なものである。The fractionation step carried out according to the invention comprises an acceptable solvent,
Any solvent fractionation using e.g. acetone, hexane or nitroparaffin or an environmental gas in pressurized liquid state.
This is a common practice.
分画は少なくとも一部溶媒を使用しない乾燥法であり、
次に分画中液相および固相の分離を有利化する界面活性
剤水性分散液の使用によりいわゆるランデ方法における
ように促進することができる。Fractionation is at least a partially solvent-free drying method;
The separation of liquid and solid phases during the fractionation can then be facilitated by the use of aqueous surfactant dispersions, as in the so-called Lande process.
しかし分画は１５〜−５℃の温度でアセトン中で、又は
１０〜−２０℃の温度でヘキサン中で行なうことが好ま
しい。Preferably, however, the fractionation is carried out in acetone at a temperature of 15 to -5°C or in hexane at a temperature of 10 to -20°C.
グリセリド分子の外側位置でのみエステル交換ル ミニ
ヘイ（Ｍｕｃｏｒ ｍ１ｅｈｅｉ ）を含む。これらの
酵素触媒は低−溶融フラクションのグリセリドの２−位
置の不飽和脂肪酸残基をエステル交換により未作用のま
ま残し、中間フラクションに対する所望の対称ジ飽和グ
リセリドの反応において製造の基礎を供することを保証
する。酵素触媒は特にこの方法に対し好ましいが、他の
触媒はこれらがアルファー位置においてのみ選択活性を
示す条件で勿論採用することができる。エステル交換反
応は触媒に無作用の溶媒、特に酵素触媒に対しヘキサン
中で、又は溶媒なしに行ない、反応はバッチ式又は連続
式で、後者の場合の触媒は反応容器に固定することが好
ましく、この容器を通して高−溶融および低−溶融混合
フラクションを含む反応物（ｒｅａｃｔｉｏｎ ｂｕｒ
ｄｅｎ ）が通過する。酵素触媒は水と接触して予め活
性化され、出願人の英国特許第１５７７９３３号明細書
に記載のように適当な担体上に支持することができる。Contains transesterified mucor mlehei only at the outer position of the glyceride molecule. These enzyme catalysts leave unsaturated fatty acid residues at the 2-position of the low-melting fraction glycerides unaltered by transesterification, providing the basis for the preparation of the desired symmetrical disaturated glycerides in the reaction of the intermediate fractions. Guarantee. Although enzymatic catalysts are particularly preferred for this method, other catalysts can of course be employed provided that they exhibit selective activity only in the alpha position. The transesterification reaction is carried out in a solvent inert to the catalyst, in particular hexane for enzyme catalysts, or without a solvent; the reaction is carried out batchwise or continuously; in the latter case the catalyst is preferably immobilized in the reaction vessel; Through this vessel a reaction mixture containing high-melting and low-melting mixed fractions is passed.
den) passes. The enzyme catalyst can be preactivated by contact with water and supported on a suitable support as described in Applicant's GB 1577933.
水分含量は反応相から水を除去するため保湿剤および／
又は他の手段により出願人の特許明細書（英国特許は放
棄、しかしＩＰ６４８５５）に従って所定限度まで反応
中得ることができる。水分含量は好ましくは溶媒を含む
反応マスの２チより多くなく、特に１チより多くない。Water content is controlled by humectants and/or humectants to remove water from the reaction phase.
or by other means up to the predetermined limits in accordance with the applicant's patent specifications (UK patent abandoned, but IP64855). The water content is preferably no more than 2 g, especially no more than 1 g of the reaction mass containing the solvent.
特に、水分活性ＡＶは反応中５［］％より少ないことが
好ましい。しかし酵素触媒は多価アルコール溶液で使用
し非常に低水分含量を維持することができる。水分含量
は部分グリセリドの生成と共に起こる加水分解の範囲を
最少にするために十分の低さであることが好ましい。In particular, the water activity AV is preferably less than 5% during the reaction. However, enzyme catalysts can be used in polyhydric alcohol solutions to maintain very low water content. Preferably, the water content is low enough to minimize the extent of hydrolysis that occurs with the formation of partial glycerides.
しかしこれらはシリカ−タイプの吸着剤を使用する選択
的吸着手段により除去することができる。However, these can be removed by selective adsorption means using silica-type adsorbents.
適当な脂肪は特にパーム油を含むが、シア、サル、ペン
タデスマ油および勿論フッアバター自体もすべて本発明
に従って加工することができる。Suitable fats include in particular palm oil, but shea, sal, pentadesma oils and, of course, fluorobacter itself can all be processed according to the invention.
植物油脂はこれらがこれらのグリセリドの２−位置に多
くの不飽和脂肪酸残基を含むため使用される。油脂の混
合物は使用することができ、トリ飽和グリセリドの不十
分な脂肪はこれらを含む他の脂肪と混合し、又は水素添
加してエステル交換反応に対し十分量を供することがで
きる。本発明の原料油脂として使用前に油は精製するこ
とが好ましく、中和および未中和油脂の双方は使用する
ことができる。Vegetable oils and fats are used because they contain many unsaturated fatty acid residues in the 2-position of their glycerides. Mixtures of fats and oils can be used, and fats lacking trisaturated glycerides can be mixed with other fats containing these or hydrogenated to provide sufficient amounts for the transesterification reaction. It is preferable to refine the oil before use as the raw material fat for the present invention, and both neutralized and unneutralized fats and oils can be used.
例
パーム油のアセ（ン分画によりパーム中間フラクション
を除去して得た等重量部のオレインおよびステアリンフ
ラクションを併せ、混和物は６倍重量のヘキサンに溶解
し、エステル交換触媒としてムコール ミニヘイ微生物
由来で、充填層反応器の珪藻土に支持され、使用前に水
により活性化された１、３−特異酵素を使用してエステ
ル交換した。５００ ｐｐｍの水を含むミセラは１時間
に６ノで０．７ ｋｌ？の触媒を含む反応器を通して供
給した。Example: Equal weight parts of olein and stearin fractions obtained by removing the palm intermediate fraction by acetic fractionation of palm oil were combined, the mixture was dissolved in 6 times the weight of hexane, and Mucor minihei derived from microorganisms was used as a transesterification catalyst. The mixture was transesterified using a 1,3-specific enzyme supported on diatomaceous earth in a packed bed reactor and activated with water before use. Micella containing 500 ppm water was transesterified at 6 nozzles per hour. It was fed through a reactor containing .7 kl of catalyst.
反応器の滞留時間は約３０分で反応は５５℃で行なった
。The residence time in the reactor was approximately 30 minutes and the reaction was conducted at 55°C.
溶媒は生成物から蒸製し、次に最初に２０℃で、次に５
℃でアセトンから再結晶して中間フラクションを回収し
た。これは表で未修正パーム油から結晶して得た中間フ
ラクションの試料と比較した。The solvent was evaporated from the product, then first at 20°C and then at 5°C.
Intermediate fractions were collected by recrystallization from acetone at °C. This was compared in the table with a sample of the intermediate fraction obtained by crystallization from unmodified palm oil.
原料油脂混和物の組成およびその成分も表に示す。The composition of the raw oil/fat mixture and its components are also shown in the table.
反応生成物由来のオレインおよびステアリンフラクショ
ンはこれらに対する組成が本質的に同じであることがわ
かった。トリグリセリド分析は銀−相ＨＰＬＣ方法忙よ
り測定される。The oleic and stearin fractions derived from the reaction products were found to be essentially the same in composition. Triglyceride analysis is determined using a silver-phase HPLC method.
表
Ａ朋 野胛懸朗胛ゼ准
４′イｙ７５”” ０ １２．３ ４．９１０−９
，４５．１２７．０ン
頂部フラクション ７７．４１Ｂ、２ ２．６ 、４
０．４ ０混和物 ４２．０１５．９ ３．７
５．５２０．７１２．３生成物 ２２．８２２．
６２５．０ ７．６２０．１１、８生成物からの中間
４．３４３．７３、２ ６．２１Ｌ４ ３．２フラク
シヨンTable A Tomo Notaku Kakero Kuze Jun 4'iy75"" 0 12.3 4.910-9
,45.127.0n top fraction 77.41B,2 2.6 ,4
0.4 0 mixture 42.015.9 3.7
5.520.712.3 Product 22.822.
625.0 7.620.11, intermediate from 8 products
4.343.73, 2 6.21L4 3.2 Fraction
Claims (1)
リドの実質量を含む植物脂肪を分画結晶してこのグリセ
リドおよび一層高度の不飽和オレインフラクションを回
収し、このオレインフラクションは次にこの植物脂肪、
好ましくはパーム油から、好ましくは分画により回収し
た実質的に飽和したグリセリド組成物と混合する、植物
脂肪から硬質バターを回収する方法において、こうして
得た混合物はエステル交換触媒、好ましくはグリセリド
の１−および３−位置においてのみ選択活性のリパーゼ
酵素の存在でエステル交換し、再配列グリセリド生成物
は好ましくは分画し、対称ジ飽和トリグリセリドを好ま
しくは分画およびエステル交換工程を含む連続方法で回
収し、これらの工程間では反応物を循環し、この植物脂
肪を含む原料油脂をそこに導入し、そこから対称ジ飽和
グリセリドフラクションを回収し、必要の場合分画およ
び／又はエステル交換工程のいずれかで溶媒を使用する
ことを特徴とする、上記方法。A vegetable fat containing a substantial amount of symmetrically disaturated triglycerides of C_1_6/C_1_8 fatty acids is fractionated and crystallized to recover this glyceride and more highly unsaturated olein fraction, which olein fraction is then converted into the vegetable fat,
In a process for recovering hard butter from vegetable fats, preferably from palm oil, preferably by mixing with a substantially saturated glyceride composition recovered by fractionation, the mixture thus obtained is combined with a transesterification catalyst, preferably one of the glycerides. transesterification in the presence of selectively active lipase enzymes only in the - and 3-positions, the rearranged glyceride products are preferably fractionated, and the symmetrical disaturated triglycerides are preferably recovered in a continuous process comprising fractionation and transesterification steps. However, the reactants are circulated between these steps, the raw oil containing this vegetable fat is introduced therein, the symmetrical disaturated glyceride fraction is recovered therefrom, and if necessary any of the fractionation and/or transesterification steps are carried out. The above method, characterized in that a solvent is used.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8431789A GB2170506B (en) | 1984-12-17 | 1984-12-17 | Edible fats |
| GB8431789 | 1984-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61179299A true JPS61179299A (en) | 1986-08-11 |
Family
ID=10571300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60285955A Pending JPS61179299A (en) | 1984-12-17 | 1985-12-17 | Recovery of hard butter from vegetable fat |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0185524B1 (en) |
| JP (1) | JPS61179299A (en) |
| AT (1) | ATE61390T1 (en) |
| AU (1) | AU568035B2 (en) |
| DE (1) | DE3582030D1 (en) |
| GB (1) | GB2170506B (en) |
| SE (1) | SE8505956L (en) |
| ZA (1) | ZA859618B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8501957A (en) * | 1985-07-09 | 1987-02-02 | Unilever Nv | FATS AND EDIBLE EMULSIONS, IN PARTICULAR DIET WITH HIGH CONTENT OF CIS-POLY-UNSATURATED FATTY ACIDS. |
| US4883684A (en) * | 1988-07-01 | 1989-11-28 | The Procter & Gamble Company | Functional hardstock fat composition |
| US5288619A (en) * | 1989-12-18 | 1994-02-22 | Kraft General Foods, Inc. | Enzymatic method for preparing transesterified oils |
| EP0457401A1 (en) * | 1990-05-17 | 1991-11-21 | Unilever N.V. | Mid-fraction production by fractional crystallization with stearin and olein fraction recycling to interesterification |
| EP0519542A1 (en) * | 1991-06-17 | 1992-12-23 | Unilever N.V. | Combined fractionation, refining and interesterification process |
| DE69737169T2 (en) * | 1996-06-26 | 2008-01-03 | Loders Croklaan B.V. | Non-tempered filling greases without trans-content |
| EP0882797B1 (en) * | 1997-06-04 | 2003-07-16 | Loders Croklaan B.V. | Preparation of symmetrical triglycerides aba |
| EP1408765B1 (en) | 2000-11-21 | 2010-09-15 | Unilever N.V. | Edible spread containing a natural fat phase |
| CN1816614B (en) * | 2003-07-09 | 2010-04-21 | 日清奥利友集团株式会社 | Process for producing symmetrical triglyceride |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57111398A (en) * | 1980-12-29 | 1982-07-10 | Asahi Denka Kogyo Kk | Ester exchange process for oils and fats |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1418759A1 (en) * | 1960-03-18 | 1969-05-08 | E F Drew & Co Inc | Method and apparatus for isolating a hard fat product from a glycero oil |
| JPS5571797A (en) * | 1978-11-21 | 1980-05-30 | Fuji Oil Co Ltd | Manufacture of cacao butter substitute fat |
| US4364868A (en) * | 1980-02-07 | 1982-12-21 | Lever Brothers Company | Cocoabutter replacement fat compositions |
| CA1241227A (en) * | 1981-07-08 | 1988-08-30 | Alasdair R. Macrae | Edible fat process |
| AU544682B2 (en) * | 1981-11-18 | 1985-06-13 | Fuji Oil Company Limited | Method for modification of fats and oils |
| EP0079986A1 (en) * | 1981-11-19 | 1983-06-01 | Fuji Oil Company, Limited | Method for the modification of fats and oils |
| IE54838B1 (en) * | 1982-04-30 | 1990-02-28 | Unilever Plc | Improvements in and relating to interesterification of triglycerides of fatty acids |
-
1984
- 1984-12-17 GB GB8431789A patent/GB2170506B/en not_active Expired
-
1985
- 1985-12-13 EP EP85309086A patent/EP0185524B1/en not_active Expired - Lifetime
- 1985-12-13 AT AT85309086T patent/ATE61390T1/en active
- 1985-12-13 DE DE8585309086T patent/DE3582030D1/en not_active Expired - Fee Related
- 1985-12-16 SE SE8505956A patent/SE8505956L/en not_active Application Discontinuation
- 1985-12-16 AU AU51275/85A patent/AU568035B2/en not_active Expired - Fee Related
- 1985-12-17 JP JP60285955A patent/JPS61179299A/en active Pending
- 1985-12-17 ZA ZA859618A patent/ZA859618B/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57111398A (en) * | 1980-12-29 | 1982-07-10 | Asahi Denka Kogyo Kk | Ester exchange process for oils and fats |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8431789D0 (en) | 1985-01-30 |
| GB2170506B (en) | 1989-08-23 |
| ATE61390T1 (en) | 1991-03-15 |
| SE8505956D0 (en) | 1985-12-16 |
| SE8505956L (en) | 1986-06-18 |
| DE3582030D1 (en) | 1991-04-11 |
| EP0185524B1 (en) | 1991-03-06 |
| AU568035B2 (en) | 1987-12-10 |
| EP0185524A3 (en) | 1987-07-15 |
| EP0185524A2 (en) | 1986-06-25 |
| AU5127585A (en) | 1986-06-26 |
| GB2170506A (en) | 1986-08-06 |
| ZA859618B (en) | 1987-08-26 |
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