JPS62272982A - Production of 1,3-distearo-2-olefin - Google Patents
Production of 1,3-distearo-2-olefinInfo
- Publication number
- JPS62272982A JPS62272982A JP61118339A JP11833986A JPS62272982A JP S62272982 A JPS62272982 A JP S62272982A JP 61118339 A JP61118339 A JP 61118339A JP 11833986 A JP11833986 A JP 11833986A JP S62272982 A JPS62272982 A JP S62272982A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- stearic acid
- recovered
- oleic acid
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 235000021355 Stearic acid Nutrition 0.000 claims abstract description 29
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 29
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000008117 stearic acid Substances 0.000 claims abstract description 29
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 22
- 229930195729 fatty acid Natural products 0.000 claims abstract description 22
- 239000000194 fatty acid Substances 0.000 claims abstract description 22
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 22
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 18
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 17
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 17
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 17
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000005642 Oleic acid Substances 0.000 claims abstract description 17
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003921 oil Substances 0.000 claims abstract description 9
- 102000004882 Lipase Human genes 0.000 claims abstract description 7
- 108090001060 Lipase Proteins 0.000 claims abstract description 7
- 239000004367 Lipase Substances 0.000 claims abstract description 7
- 235000019421 lipase Nutrition 0.000 claims abstract description 7
- 239000000470 constituent Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 239000010409 thin film Substances 0.000 claims abstract description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 13
- 239000003925 fat Substances 0.000 claims description 12
- 239000002994 raw material Substances 0.000 claims description 6
- RBLADLVPSYELCA-IKPAITLHSA-N 1,3-bis(octadecanoyloxy)propan-2-yl (9z)-octadec-9-enoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC RBLADLVPSYELCA-IKPAITLHSA-N 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract description 9
- 235000019198 oils Nutrition 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 239000004006 olive oil Substances 0.000 abstract description 2
- 235000008390 olive oil Nutrition 0.000 abstract description 2
- 239000000344 soap Substances 0.000 abstract description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- -1 etc. Chemical compound 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 235000019197 fats Nutrition 0.000 description 10
- 238000000034 method Methods 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
【発明の詳細な説明】
３、発明の詳細な説明
（ａ）産業上の利用分野
本発明は対称型トリグリセリドである１、３−ジステア
ロ−２−オレイン（以下ＳＯＳファツトという）を安価
に製造する方法に関するものである。Detailed Description of the Invention 3. Detailed Description of the Invention (a) Industrial Field of Application The present invention produces 1,3-distearo-2-olein (hereinafter referred to as SOS fat), which is a symmetrical triglyceride, at low cost. It is about the method.
（ｂ）従来の技術
ＳＯＳファツトは、構成脂肪酸としてオレイン酸を多く
含む油脂とステアリン酸をたとえば、リパーゼによって
エステル交換を行わせることにより製造されるが、エス
テル交換反応後に系に存在する脂肪酸を除去し回収する
必要がある。しかし、この脂肪酸は副生じたオレイン酸
と未反応のステアリン酸の混合脂肪酸であり、エステル
交換反応の原料としてそのまま再利用することはできな
い。(b) Conventional technology SOS fats are produced by transesterifying fats and oils containing a large amount of oleic acid as constituent fatty acids with stearic acid, for example, using lipase, but after the transesterification reaction, the fatty acids present in the system are removed. It is necessary to collect it. However, this fatty acid is a mixed fatty acid of by-product oleic acid and unreacted stearic acid, and cannot be reused as is as a raw material for transesterification.
そのため従来の技術では、この混合脂肪酸を精留し、オ
レイン酸とステアリン酸を分離してステアリン酸を再利
用する方法が考えられる。Therefore, in the conventional technology, a method of rectifying this mixed fatty acid to separate oleic acid and stearic acid and reusing the stearic acid has been considered.
（Ｃ）発明が解決しようとする問題点
しかし乍らこのような方法では、設備費、運転費ともに
高いこと、また分離した後もステアリン酸だけが再利用
されるがオレイン酸は再利用できないなどの欠点がある
。(C) Problems to be solved by the invention However, with this method, both equipment costs and operating costs are high, and even after separation, only stearic acid is reused, but oleic acid cannot be reused. There are drawbacks.
本発明の目的はこのようなエステル交換反応において、
回収した脂肪酸を有効に再利用し、ＳＯＳファツトを工
業的に効率良く製造する方法を提供することにある。The purpose of the present invention is to carry out such a transesterification reaction,
It is an object of the present invention to provide a method for industrially and efficiently producing SOS fat by effectively reusing recovered fatty acids.
（ｄ）問題点を解決するための手段
即ち本発明は、構成脂肪酸としてオレイン酸を多（含む
油脂にステアリン酸をエステル交換反応させてＳＯＳフ
ァツトを製造する方法において、エステル交換反応後に
脱酸回収したステアリン酸とオレイン酸の混合物を水素
添加によりステアリン酸に変換し、これを前記エステル
交換反応の原料であるステアリン酸として用いることを
特徴とするＳＯＳファントの製造法である。(d) Means for solving the problem, that is, the present invention is a method for producing SOS fat by transesterifying stearic acid with fats and oils containing a large amount of oleic acid as a constituent fatty acid, and deacidification and recovery after transesterification. This is a method for producing an SOS fan, which is characterized in that the mixture of stearic acid and oleic acid obtained is converted into stearic acid by hydrogenation, and this is used as stearic acid, which is a raw material for the transesterification reaction.
構成脂肪酸としてオレイン酸を多く含む油脂としては、
オイレックひまわり油、オイレックサフラワー油、オリ
ーブ油などの天然油脂およびオレイン酸に富む合成油を
用いることができる。Oils and fats that contain a large amount of oleic acid as a constituent fatty acid include:
Natural oils such as oilc sunflower oil, oilc safflower oil, olive oil and synthetic oils rich in oleic acid can be used.
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ができるが
、ＳＯＳファツトの収率を高めるには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, but it is preferable to use a lipase with a specificity of 1.3 in order to increase the yield of SOS fat.
エステル交換した後、脂肪酸の除去を行う。その方法は
水蒸気蒸留法などの公知の方法を採用できるが、薄膜蒸
発装置を用いると脱酸を効率良く行うことができるので
好ましい、このうな装置としては例えば円筒竪型固定翼
式遠心薄膜蒸発機が適当である。After transesterification, fatty acids are removed. Although a known method such as steam distillation can be used for this purpose, it is preferable to use a thin film evaporator because deoxidation can be carried out efficiently.An example of such an apparatus is a cylindrical vertical fixed blade centrifugal thin film evaporator. is appropriate.
分離回収された混合脂肪酸は、一般の動植物油脂の水素
添加反応に利用されるオートクレーブもしくはこれと同
等の機能をもつ装置で水素添加できる。その条件は、と
くに限定されないが、すべてのオレイン酸がステアリン
酸に変化するまで水添を行う、水添反応後は触媒と微量
の脂肪酸石けんを除くため、通常クエン酸などを添加し
て濾過を行いステアリン酸を得る。The separated and recovered mixed fatty acids can be hydrogenated in an autoclave that is commonly used for the hydrogenation reaction of animal and vegetable oils and fats, or in a device with equivalent functionality. The conditions are not particularly limited, but hydrogenation is carried out until all of the oleic acid is converted to stearic acid. After the hydrogenation reaction, citric acid is usually added and filtration is carried out to remove the catalyst and trace amounts of fatty acid soap. to obtain stearic acid.
このステアリン酸は、最初のエステル交換反応の原料で
あるステアリン酸として循環再利用する。This stearic acid is recycled and reused as stearic acid, which is the raw material for the initial transesterification reaction.
（ｅ）実施例
実施例１
オレイックひまわり油１．０００ｇに対しステアリン酸
１．０００ｇを混合し加温溶解した汲水を飽和させる（
７０℃）、これを固定化す″パーゼ２０ｇを充填し６８
℃に保ったカラムを通しエステル交換反応を行った。得
られた反応物は１，０００ｇの混合脂肪酸を含む。反応
物５００ｇを２１のガラス製蒸留装置で常法により脂肪
酸を分離回収した。(e) Examples Example 1 Mix 1.000 g of stearic acid with 1.000 g of oleic sunflower oil, dissolve the mixture by heating, and saturate the pumped water (
70°C), then fill with 20g of pase to fix it.
The transesterification reaction was carried out through a column kept at ℃. The resulting reaction product contains 1,000 g of mixed fatty acids. Fatty acids were separated and recovered from 500 g of the reactant using a 21 glass distillation apparatus using a conventional method.
以上の操作を計４回行い得られた脂肪酸を一括し４Ｎ型
オートクレーブで水素添加を行った。条件は、温度１８
０℃、Ｈｚ １．５ｋｇ／ａｄ、 Ｉ％！拌３０Ｑｒｐ
ｍ、触媒ニッケル系０．２％（対仕込原料）、時間１．
５時間、触媒濾別特使用クエン酸（粉末）０．３％であ
る。The above operation was carried out four times in total, and the obtained fatty acids were collectively hydrogenated in a 4N type autoclave. The conditions are temperature 18
0℃, Hz 1.5kg/ad, I%! stirring 30Qrp
m, catalyst nickel system 0.2% (based on charged raw materials), time 1.
5 hours, special use citric acid (powder) 0.3% by catalyst filtration.
水素添加物を分析の結果、脂肪酸中のステアリン酸は１
００．０％であった。As a result of hydrogenation analysis, stearic acid in fatty acids is 1
It was 00.0%.
このものを再度エステル交換反応の原料として用いたが
、最初に用いたステアリン酸と何ら差異のない結果を得
た。This product was used again as a raw material for the transesterification reaction, but the results were no different from those of the stearic acid used initially.
（「）発明の効果
エステル交換反応によりＳＯＳファツトを製造する段階
で生ずる混合脂肪酸は一旦オレイン酸を含むことになる
が、本発明によれば、これが水素添加反応によって再び
ステアリン酸に戻され再利用されるので、ＳＯＳファツ
トの製造にあオこってはステアリン酸は各工程で生じた
損失分だけ補充すればよく、反応の都度新しいステアリ
ン酸を用意しなくてもい、これは製造コスト面での利点
が掻めて大きく、ＳＯＳファツトの製造費を大幅に低減
できる。(“) Effects of the Invention The mixed fatty acids produced in the step of producing SOS fat through the transesterification reaction once contain oleic acid, but according to the present invention, this is returned to stearic acid through the hydrogenation reaction and reused. Therefore, when producing SOS fat, stearic acid only needs to be replenished by the amount lost in each step, and there is no need to prepare new stearic acid for each reaction, which reduces production costs. The advantages are significant and the manufacturing cost of SOS fat can be reduced significantly.
Claims (4)
テアリン酸をエステル交換反応させて１，３−ジステア
ロ−２−オレインを製造する方法において脱酸回収した
ステアリン酸とオレイン酸の混合物を水素添加によりス
テアリン酸に変換し、これを前記エステル交換反応の原
料であるステアリン酸として用いることを特徴とする１
，３−ジステアロ−２−オレインの製造法。(1) A mixture of stearic acid and oleic acid, which has been deoxidized and recovered in a method for producing 1,3-distearo-2-olein by transesterifying stearic acid with fats and oils containing a large amount of oleic acid as a constituent fatty acid, is hydrogenated. 1, characterized in that it is converted into stearic acid and used as stearic acid, which is a raw material for the transesterification reaction.
, 3-distearo-2-olein production method.
の範囲第（１）項の製造法。(2) The production method according to claim (1), in which the transesterification reaction is carried out using lipase.
特許請求の範囲第（２）項記載の製造法。(3) The production method according to claim (2), which uses a mono- and trispecific lipase as the lipase.
求の範囲第（１）項記載の製造法。(4) The production method according to claim (1), in which the fatty acid is recovered using a thin film evaporator.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61118339A JPH0783718B2 (en) | 1986-05-21 | 1986-05-21 | Process for producing 1,3-distearo-2-olein |
| CN 87107927 CN1025630C (en) | 1986-05-21 | 1987-11-20 | Method for the preparation of ester-exchanged oil or fat |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61118339A JPH0783718B2 (en) | 1986-05-21 | 1986-05-21 | Process for producing 1,3-distearo-2-olein |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62272982A true JPS62272982A (en) | 1987-11-27 |
| JPH0783718B2 JPH0783718B2 (en) | 1995-09-13 |
Family
ID=14734227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61118339A Expired - Lifetime JPH0783718B2 (en) | 1986-05-21 | 1986-05-21 | Process for producing 1,3-distearo-2-olein |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0783718B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62273293A (en) * | 1986-05-21 | 1987-11-27 | 日清製油株式会社 | Production of interesterified oils and fats |
| WO2003000832A1 (en) * | 2001-06-26 | 2003-01-03 | Fuji Oil Company, Limited | Process for producing processed glyceride fat |
| GB2490324A (en) * | 2011-04-21 | 2012-10-31 | Desmet Ballestra Engineering S A Nv | Improved enzyme interesterification process |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1642959B1 (en) | 2003-07-09 | 2010-05-19 | The Nisshin OilliO Group, Ltd. | Process for producing symmetrical triglyceride |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56163196A (en) * | 1980-05-20 | 1981-12-15 | Fuji Oil Co Ltd | Process of oil and grease |
| JPS59500649A (en) * | 1982-04-30 | 1984-04-19 | ユニリ−バ−・ナ−ムロ−ゼ・ベンノ−トシヤ−プ | Reordering method |
| JPS6098984A (en) * | 1983-09-05 | 1985-06-01 | ノボ ノルディスク アクティーゼルスカブ | Production of immobilized lipase product |
-
1986
- 1986-05-21 JP JP61118339A patent/JPH0783718B2/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56163196A (en) * | 1980-05-20 | 1981-12-15 | Fuji Oil Co Ltd | Process of oil and grease |
| JPS59500649A (en) * | 1982-04-30 | 1984-04-19 | ユニリ−バ−・ナ−ムロ−ゼ・ベンノ−トシヤ−プ | Reordering method |
| JPS6098984A (en) * | 1983-09-05 | 1985-06-01 | ノボ ノルディスク アクティーゼルスカブ | Production of immobilized lipase product |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62273293A (en) * | 1986-05-21 | 1987-11-27 | 日清製油株式会社 | Production of interesterified oils and fats |
| WO2003000832A1 (en) * | 2001-06-26 | 2003-01-03 | Fuji Oil Company, Limited | Process for producing processed glyceride fat |
| US6969771B2 (en) | 2001-06-26 | 2005-11-29 | Fuji Oil Company, Limited | Process for producing processed glyceride fat |
| GB2490324A (en) * | 2011-04-21 | 2012-10-31 | Desmet Ballestra Engineering S A Nv | Improved enzyme interesterification process |
| US8697393B2 (en) | 2011-04-21 | 2014-04-15 | N.V. Desmet Ballestra Engineering S.A. | Enzyme interesterification process |
| GB2490324B (en) * | 2011-04-21 | 2014-06-11 | Desmet Ballestra Engineering S A Nv | Improved enzyme interesterification process |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0783718B2 (en) | 1995-09-13 |
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