JPS62273293A - Production of interesterified oils and fats - Google Patents
Production of interesterified oils and fatsInfo
- Publication number
- JPS62273293A JPS62273293A JP11833886A JP11833886A JPS62273293A JP S62273293 A JPS62273293 A JP S62273293A JP 11833886 A JP11833886 A JP 11833886A JP 11833886 A JP11833886 A JP 11833886A JP S62273293 A JPS62273293 A JP S62273293A
- Authority
- JP
- Japan
- Prior art keywords
- fats
- fatty acids
- oils
- thin film
- film evaporator
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 235000014593 oils and fats Nutrition 0.000 title description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 27
- 229930195729 fatty acid Natural products 0.000 claims description 27
- 239000000194 fatty acid Substances 0.000 claims description 27
- 150000004665 fatty acids Chemical class 0.000 claims description 27
- 239000003921 oil Substances 0.000 claims description 25
- 239000010409 thin film Substances 0.000 claims description 24
- 239000003925 fat Substances 0.000 claims description 21
- 238000005809 transesterification reaction Methods 0.000 claims description 9
- 102000004882 Lipase Human genes 0.000 claims description 5
- 108090001060 Lipase Proteins 0.000 claims description 5
- 239000004367 Lipase Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 235000019421 lipase Nutrition 0.000 claims description 5
- 244000299461 Theobroma cacao Species 0.000 claims description 3
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 claims description 2
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 claims description 2
- 235000001046 cacaotero Nutrition 0.000 claims description 2
- 235000019198 oils Nutrition 0.000 description 23
- 238000000034 method Methods 0.000 description 13
- 238000004821 distillation Methods 0.000 description 6
- 238000001256 steam distillation Methods 0.000 description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 235000002316 solid fats Nutrition 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 235000013341 fat substitute Nutrition 0.000 description 2
- 239000003778 fat substitute Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Fats And Perfumes (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】
３、発明の詳細な説明
ｆａ）産業上の利用分野
本発明は油脂と脂肪酸のエステル交換後に系に存在する
脂肪酸を効率的に除去して良質のエステル交換油脂を製
造する方法に関する。Detailed Description of the Invention 3. Detailed Description of the Invention fa) Industrial Application Field The present invention efficiently removes fatty acids present in the system after transesterification of fats and oils to produce high-quality transesterified fats and oils. Regarding how to.
（ｂ）従来の技術
油脂を改質する手段としてのエステル交換反応は特定の
脂肪酸と油脂を反応させることによって液体油を個体脂
に、また、固体脂を液体油に転換せしめることができる
。同様に固体脂と脂肪酸を反応させることにより性質の
異なる固体脂を得ることができる。さらに液体油と脂肪
酸の反応についても同様な結果を得ることができる。(b) Prior Art Transesterification as a means of modifying fats and oils can convert liquid oils into solid fats and solid fats into liquid oils by reacting specific fatty acids with fats and oils. Similarly, solid fats with different properties can be obtained by reacting solid fats and fatty acids. Furthermore, similar results can be obtained for reactions between liquid oils and fatty acids.
油脂と脂肪酸を反応させる一例として、トリグリセリド
の２位がオレイン酸に冨む油脂にパルミチン酸もしくは
ステアリン酸を１，３特異性を有するリパーゼを用いて
エステル交換を行いカカオ代用脂を得る方法がある。こ
の場合にパルミチン酸もしくはステアリン酸は油脂１モ
ルに対し相当量すなわち少なくとも２モルを超え望まし
くは３〜４モルを用いる必要がある。これらの脂肪酸は
反応により油脂（トリグリセリド）に含まれる脂肪酸と
入れ代わり、また未反応の脂肪酸が残存する。One example of reacting fats and oils with fatty acids is a method of transesterifying palmitic acid or stearic acid to fats and oils in which the 2nd position of the triglyceride is oleic acid using a lipase with 1,3 specificity to obtain a cocoa fat substitute. . In this case, it is necessary to use palmitic acid or stearic acid in a considerable amount, that is, at least 2 moles, preferably 3 to 4 moles, per mole of oil or fat. These fatty acids replace fatty acids contained in fats and oils (triglycerides) through reaction, and unreacted fatty acids remain.
したがって、反応終了後には目的の油脂を得るために上
記の脂肪酸を除去する必要がある。Therefore, after the completion of the reaction, it is necessary to remove the above-mentioned fatty acids in order to obtain the desired fat or oil.
その他の油脂と脂肪酸とのエステル交換反応の場合も、
同様である。In the case of transesterification reactions between other fats and oils and fatty acids,
The same is true.
油脂と共存する脂肪酸を除去もしくは分離する手段とし
て広く利用されている方法は、いわゆる水蒸気蒸留法と
よばれる方法である。この方法では一定容量を有する容
器内に油脂と脂肪酸の混合物を入れこれに高温真空下に
おいて水蒸気を吹き込んで脂肪酸を留出除去する。この
方法は脂肪酸が留出し始めてから留出し終わるまでに少
なくとも６０分以上の滞留時間が必要である。このよう
な条件下においてエステル交換反応物から脂肪酸を除去
しようとすれば、油脂（トリグリセリド）と脂肪酸の間
でエステル交換および／又は分子内転移が起こり、本来
の目的とする油脂（トリグリセリド）の収率が低下する
。この傾向は温度が高いほど、また時間が長くなるほど
強く現われる。A widely used method for removing or separating fatty acids coexisting with fats and oils is a method called steam distillation. In this method, a mixture of fats and oils and fatty acids is placed in a container having a certain volume, and steam is blown into the mixture under high-temperature vacuum to distill and remove the fatty acids. This method requires a residence time of at least 60 minutes from the start of fatty acid distillation until the end of distillation. If fatty acids are attempted to be removed from the transesterification product under these conditions, transesterification and/or intramolecular transfer will occur between the fats and oils (triglycerides) and the fatty acids, and the original target yield of fats and oils (triglycerides) will be hindered. rate decreases. This tendency becomes more pronounced as the temperature gets higher and the time gets longer.
又、脂肪酸を高温に長くさらすことは着色の原因にもな
り好ましくない。Furthermore, exposing fatty acids to high temperatures for a long period of time is undesirable as it may cause discoloration.
（Ｃ１発明が解決しようとする問題点
本発明の目的は、従来用いられている水蒸気蒸留法に代
って短時間で熱変化を受けることなく連続的に効率よく
脂肪酸を分離除去し、良質のエステル交換油を製造する
方法を提供することにある。(C1 Problems to be Solved by the Invention The purpose of the present invention is to replace the conventionally used steam distillation method by separating and removing fatty acids continuously and efficiently without undergoing thermal changes in a short period of time, thereby producing high-quality fatty acids. An object of the present invention is to provide a method for producing transesterified oil.
（ｄ１問題点を解決するための手段
本発明者らは鋭意研究の結果、脂肪酸の除去に薄膜蒸留
装置を用いると上記の目的が達成されることを見い出し
た。(Means for Solving Problem d1) As a result of extensive research, the present inventors have discovered that the above object can be achieved by using a thin film distillation apparatus to remove fatty acids.
本発明はかかる知見に基づいて完成されたもので、油脂
を脂肪酸とエステル交換させたのち、反応系中に存在す
る脂肪酸を薄膜蒸留装置を用いて除くことを特徴とする
エステル交換油の製造法である。The present invention was completed based on this knowledge, and is a method for producing transesterified oil, which comprises transesterifying fats and oils with fatty acids, and then removing fatty acids present in the reaction system using a thin film distillation apparatus. It is.
エステル交換反応はリパーゼを用いる方法、アルカリ触
媒を用いる方法などの公知の手段によることできるが、
カカオ代用脂を目的とする場合は、１．３特異性のリパ
ーゼを用いることが望ましい。The transesterification reaction can be carried out by known means such as a method using lipase or a method using an alkali catalyst.
If the purpose is to use a cacao fat substitute, it is desirable to use a lipase with 1.3 specificity.
本発明で使用する薄膜式蒸発装置としては円錐型固定翼
式遠心薄膜蒸発機、円筒横型固定翼式遠心薄膜蒸発機、
円筒竪型固定翼式遠心薄膜蒸発機、円筒竪型かき取り式
遠心薄膜蒸発機、凝縮器内蔵型かき取り式遠心薄膜蒸発
機、円錐型遠心薄膜蒸などを挙げることができるが、こ
のうち円筒竪型固定翼式遠心薄膜蒸発機が好ましい。薄
膜蒸発装置の運転条件は温度２００〜２６０°Ｃ１真空
圧力０．１〜５−寵Ｈｇ、滞留時間１〜１０秒が適当で
ある。Thin-film evaporators used in the present invention include a conical fixed-blade centrifugal thin-film evaporator, a cylindrical horizontal fixed-blade centrifugal thin-film evaporator,
Examples include a cylindrical vertical fixed-blade centrifugal thin film evaporator, a cylindrical vertical scraping type centrifugal thin film evaporator, a scraping type centrifugal thin film evaporator with a built-in condenser, and a conical centrifugal thin film evaporator. A vertical fixed-blade centrifugal thin film evaporator is preferred. Appropriate operating conditions for the thin film evaporator are a temperature of 200 to 260 DEG C., a vacuum pressure of 0.1 to 5 mmHg, and a residence time of 1 to 10 seconds.
ｔｅｌ実施例
実施例１
オレイックひまわり油１部（重量）に対しステアリン酸
１部（重量）を混合し、７０℃で溶解した。これに０．
２〜０．３％の水を加え攪拌する。これを６８〜６９℃
に保った固定化リパーゼの層を通しエステル交換反応を
行った。反応物は円筒竪型固定翼式遠心薄膜蒸発機（関
西化学機械製作（株）製）で油脂と脂肪酸を分離した。tel Examples Example 1 1 part (by weight) of stearic acid was mixed with 1 part (by weight) of oleic sunflower oil and dissolved at 70°C. 0 for this.
Add 2-0.3% water and stir. This is 68-69℃
The transesterification reaction was carried out through a layer of immobilized lipase maintained at . The reactants were separated into fats and oils and fatty acids using a cylindrical vertical fixed-blade centrifugal thin film evaporator (manufactured by Kansai Kagaku Kikai Seisaku Co., Ltd.).
比較のため従来の水蒸気蒸留法により脂肪酸の分離を行
った。For comparison, fatty acids were separated using a conventional steam distillation method.
以上の結果を第１表に示す。The above results are shown in Table 1.
（ｆ）発明の効果
本発明の方法では脂肪酸を分離する際の滞留時間が極め
て短いため、温度を水蒸気蒸留法に比べて２０〜５０℃
以上高くしても油脂の熱的変化を起こさない利点がある
。即ち従来の水蒸気蒸留法にみられる望ましくないエス
テル交換や分子内転移が起こらず目的とするエステル交
換油の収率が高い。また熱による着色も起きにくい。(f) Effect of the invention In the method of the present invention, the residence time when separating fatty acids is extremely short, so the temperature is 20 to 50°C compared to the steam distillation method.
Even if the temperature is higher than that, there is an advantage that no thermal changes occur in the oil or fat. That is, undesirable transesterification and intramolecular rearrangement that occur in conventional steam distillation methods do not occur, and the yield of the desired transesterified oil is high. It is also less prone to discoloration due to heat.
さらに薄膜式蒸発装置は熱効率が高いので熱エネルギー
の節約が可能となる。Furthermore, the thin film evaporator has high thermal efficiency, making it possible to save thermal energy.
特許出願人 日清製油株式会社
手続補正書（自発）
昭和６１ｖ、８Ｊ−１）９日
１、事件の表示
昭和６１年特許願第１）８３３８号
２、発明の名称
エステル交換油脂の製造法
３、 補正をする者
事件との関係 特許出願人
住 所 東京都中央区新川−丁目２３番１号本件に
関する連絡は下記にお願いします。Patent Applicant: Nisshin Oil Co., Ltd. Procedural Amendment (Voluntary) 1988 61v, 8J-1) 9th 1, Indication of Case 1988 Patent Application No. 1) 8338 2, Title of Invention Process for Producing Transesterified Oils and Fats 3 , Relationship with the case of the person making the amendment Patent Applicant Address: 23-1 Shinkawa-chome, Chuo-ku, Tokyo For inquiries regarding this matter, please contact the following.
郵便番号 ２２１
住 所 神奈川県横浜市神奈用区千若町１−３名
称 日清製油株式会社 研究所４、補正の対象
明細書の発明の詳細な説明の欄
５、補正の内容
（１） 明細書第４頁５行「薄膜蒸留装置」を「薄膜
蒸発装置」と訂正する。Postal code 221 Address 1-3 Chiwaka-cho, Kanayō-ku, Yokohama-shi, Kanagawa Prefecture
Name Nisshin Oil Co., Ltd. Research Institute 4, Detailed explanation of the invention column 5 of the specification subject to amendment, Contents of the amendment (1) Page 4 of the specification, line 5, “thin film distillation device” is changed to “thin film evaporation device” correct.
（２）同第４頁９行「薄膜蒸留装置」を「薄膜蒸発装置
」と訂正する。(2) On page 4, line 9, “thin film distillation device” is corrected to “thin film evaporation device.”
（３）同第４頁１６行「薄膜式蒸発装置」を「薄膜蒸発
装置」と訂正する。(3) On page 4, line 16, "thin film evaporator" is corrected to "thin film evaporator."
（４） 同第７頁９行「薄膜式蒸発装置」を「薄膜蒸
発装置」と訂正する。(4) On page 7, line 9, "thin film evaporator" is corrected to "thin film evaporator."
Claims (4)
中に存在する脂肪酸を薄膜蒸発装置を用いて除くことを
特徴とするエステル交換油脂の製造法。(1) A method for producing transesterified fats and oils, which comprises transesterifying fats and oils with fatty acids and then removing fatty acids present in the reaction system using a thin film evaporator.
範囲第（１）項記載の製造法。(2) The production method according to claim (1), in which the transesterification is carried out using lipase.
である特許請求の範囲第（１）項記載の製造法。(3) The manufacturing method according to claim (1), wherein the thin film evaporator is a cylindrical vertical fixed-blade centrifugal thin film evaporator.
の範囲第（１）項記載の製造法。(4) The production method according to claim (1), wherein the transesterified fat is a cacao substitute fat.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61118338A JPH0631396B2 (en) | 1986-05-21 | 1986-05-21 | Method for producing transesterified oils and fats |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61118338A JPH0631396B2 (en) | 1986-05-21 | 1986-05-21 | Method for producing transesterified oils and fats |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62273293A true JPS62273293A (en) | 1987-11-27 |
| JPH0631396B2 JPH0631396B2 (en) | 1994-04-27 |
Family
ID=14734199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61118338A Expired - Fee Related JPH0631396B2 (en) | 1986-05-21 | 1986-05-21 | Method for producing transesterified oils and fats |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0631396B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8435592B2 (en) | 2010-09-13 | 2013-05-07 | General Mills, Inc. | Shortening particle compositions and dough products made therefrom |
| US9040110B2 (en) | 2010-09-13 | 2015-05-26 | General Mills, Inc. | Shortening particle compositions and dough products made therefrom |
| US9801392B2 (en) | 2012-04-27 | 2017-10-31 | General Mills, Inc. | Fat particle compositions containing salt, dough and baked dough articles made therefrom, and related methods |
| US9943084B2 (en) | 2011-05-09 | 2018-04-17 | General Mills, Inc. | Fat compositions and related methods, including shortening particles and shortening compositions without added non-interestified hardstock fat, and related products |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4950746A (en) * | 1972-09-18 | 1974-05-17 | ||
| JPS5512080A (en) * | 1978-07-13 | 1980-01-28 | Takeshi Hiramatsu | Method of bonding label to extruded polyethylene net sack |
| JPS5544120A (en) * | 1978-09-19 | 1980-03-28 | Nec Corp | Rotary air bearing |
| JPS62272982A (en) * | 1986-05-21 | 1987-11-27 | Nisshin Oil Mills Ltd:The | Production of 1,3-distearo-2-olefin |
-
1986
- 1986-05-21 JP JP61118338A patent/JPH0631396B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4950746A (en) * | 1972-09-18 | 1974-05-17 | ||
| JPS5512080A (en) * | 1978-07-13 | 1980-01-28 | Takeshi Hiramatsu | Method of bonding label to extruded polyethylene net sack |
| JPS5544120A (en) * | 1978-09-19 | 1980-03-28 | Nec Corp | Rotary air bearing |
| JPS62272982A (en) * | 1986-05-21 | 1987-11-27 | Nisshin Oil Mills Ltd:The | Production of 1,3-distearo-2-olefin |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8435592B2 (en) | 2010-09-13 | 2013-05-07 | General Mills, Inc. | Shortening particle compositions and dough products made therefrom |
| US8920865B2 (en) | 2010-09-13 | 2014-12-30 | General Mills, Inc. | Shortening particle compositions and dough products made therefrom |
| US9040110B2 (en) | 2010-09-13 | 2015-05-26 | General Mills, Inc. | Shortening particle compositions and dough products made therefrom |
| US9814250B2 (en) | 2010-09-13 | 2017-11-14 | General Mills, Inc. | Shortening particle compositions and dough products made therefrom |
| US9943084B2 (en) | 2011-05-09 | 2018-04-17 | General Mills, Inc. | Fat compositions and related methods, including shortening particles and shortening compositions without added non-interestified hardstock fat, and related products |
| US9801392B2 (en) | 2012-04-27 | 2017-10-31 | General Mills, Inc. | Fat particle compositions containing salt, dough and baked dough articles made therefrom, and related methods |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0631396B2 (en) | 1994-04-27 |
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