JPH0783718B2 - Process for producing 1,3-distearo-2-olein - Google Patents
Process for producing 1,3-distearo-2-oleinInfo
- Publication number
- JPH0783718B2 JPH0783718B2 JP61118339A JP11833986A JPH0783718B2 JP H0783718 B2 JPH0783718 B2 JP H0783718B2 JP 61118339 A JP61118339 A JP 61118339A JP 11833986 A JP11833986 A JP 11833986A JP H0783718 B2 JPH0783718 B2 JP H0783718B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- stearic acid
- fat
- transesterification reaction
- oleic
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title description 10
- 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 title description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 28
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 28
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 28
- 239000008117 stearic acid Substances 0.000 claims description 28
- 238000005809 transesterification reaction Methods 0.000 claims description 23
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 18
- 229930195729 fatty acid Natural products 0.000 claims description 18
- 239000000194 fatty acid Substances 0.000 claims description 18
- 150000004665 fatty acids Chemical class 0.000 claims description 18
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 17
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 12
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 12
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 12
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000005642 Oleic acid Substances 0.000 claims description 12
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 12
- 239000002994 raw material Substances 0.000 claims description 10
- 102000004882 Lipase Human genes 0.000 claims description 9
- 108090001060 Lipase Proteins 0.000 claims description 9
- 239000004367 Lipase Substances 0.000 claims description 9
- 235000019421 lipase Nutrition 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 235000021314 Palmitic acid Nutrition 0.000 claims description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 3
- -1 In addition Substances 0.000 claims 1
- 239000003925 fat Substances 0.000 description 20
- 235000019197 fats Nutrition 0.000 description 19
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 125000005456 glyceride group Chemical group 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 235000019486 Sunflower oil Nutrition 0.000 description 4
- 239000002600 sunflower oil Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 230000001737 promoting effect Effects 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 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
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Description
【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ファットという）を安価に製
造する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION (a) Field of Industrial Application The present invention relates to a method for inexpensively producing symmetric triglyceride 1,3-distearo-2-olein (hereinafter referred to as SOS fat).
（ｂ）従来の技術 SOSファットは、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例えば、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
交換反応時の水分含量の多少により、油脂が部分的加水
分解されて部分グリセリドとなり、あるいはエステル交
換反応に長時間を必要とする。このためエステル交換反
応時の系の最適水分量が検討されている。また、エステ
ル交換反応後に存在する脂肪酸を除去し回収する必要が
ある。しかし、この脂肪酸は副生し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、これを新たなエ
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。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とを分離してステア
リン酸を再利用する方法が考えられる。(B) Prior art SOS fat is produced by transesterification of fats and oils containing a large amount of oleic acid as a constituent fatty acid and stearic acid, for example, by lipase, but depending on the water content during the transesterification reaction, Fats and oils are partially hydrolyzed to partial glycerides, or transesterification requires a long time. Therefore, the optimum water content of the system during the transesterification reaction has been investigated. In addition, it is necessary to remove and recover the fatty acids present after the transesterification reaction. However, this fatty acid is a mixed fatty acid of by-produced oleic acid and unreacted stearic acid, and cannot be reused as it is as a raw material for a new transesterification reaction. Therefore, in the conventional technique, a method of rectifying this mixed fatty acid, separating oleic acid and stearic acid, and reusing stearic acid can be 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, in such a method, both the equipment cost and the operating cost are high, and only stearic acid can be reused after separation, but oleic acid cannot be reused. There is a drawback of.
本発明の目的はこのようなエステル交換反応において、
効率的にエステル交換反応を進め、およびエステル交換
反応物から回収した脂肪酸を有効に再利用し、SOSファ
ッ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 object of the present invention is to perform such a transesterification reaction,
It is an object of the present invention to provide a method for industrially and efficiently producing SOS fat by efficiently promoting a transesterification reaction and effectively reusing a fatty acid recovered from a transesterification reaction product.
（ｄ）問題点を解決するための手段 すなわち本発明は、構成脂肪酸としてオレイン酸を多く
含み、かつパルミチン酸およびステアリン酸を実質的に
含まない油脂とステアリン酸とを、予め70℃に加温融解
して水分を飽和させ、これを固定化1,3特異性リパーゼ
を充填したカラムに流してエステル交換反応させ、該反
応物から脱酸回収したステアリン酸およびオレイン酸の
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ファットの製造法である。(D) Means for Solving the Problems That is, according to the present invention, an oil and fat containing a large amount of oleic acid as a constituent fatty acid and substantially free of palmitic acid and stearic acid and stearic acid are heated to 70 ° C. in advance. After melting and saturating water, the water was passed through a column packed with immobilized 1,3-specific lipase for transesterification reaction, and the mixture of stearic acid and oleic acid recovered from the reaction product was steared by hydrogenation. It is a method for producing SOS fat, which is characterized in that it is converted into an acid and 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み、かつパルミチ
ン酸およびステアリン酸を実質的に含まない油脂として
は、オレイックひまわり油脂、オレイックサフラワー油
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。As the oil and fat containing a large amount of oleic acid as a constituent fatty acid, and substantially free of palmitic acid and stearic acid, natural oils and fats such as oleic sunflower oil and fat, oleic safflower oil and synthetic oil rich in oleic acid can be used. .
エステル交換反応に供する原料は、前記油脂とステアリ
ン酸とを例えば等重量で混合し、これを70℃に加温して
溶解し、この温度で水分を飽和させる。原料を溶解させ
るための溶媒は必要ない。As a raw material to be subjected to the transesterification reaction, for example, the oil and fat and stearic acid are mixed in equal weights, and the mixture is heated to 70 ° C. to dissolve it, and the water content is saturated at this temperature. No solvent is needed to dissolve the raw materials.
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ファッ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。また、リパーゼは公知の担
体に固定化して固定化リパーゼとし、これを充填したカ
ラムを反応器とすることが好ましい。The transesterification reaction can be carried out by a known means such as a method using lipase or a method using an alkali catalyst, but it is desirable to use a 1,3-specific lipase in order to increase the yield of SOS fat. Further, it is preferable that the lipase is immobilized on a known carrier to be immobilized lipase, and the column packed with this is used as a reactor.
前記の水飽和した原料を、例えば固定化1,3特異性リパ
ーゼを充填したカラムに連続的に通し、エステル交換反
応を行わせる。The water-saturated raw material is continuously passed through, for example, a column packed with immobilized 1,3-specific lipase to carry out a transesterification reaction.
エステル交換した後、反応物からグリセリドと脂肪酸と
を分離する。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。このような装置とし
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, the reaction product is separated into glyceride and fatty acid. As the method, a known method such as a steam distillation method can be adopted, but it is preferable to use a thin film evaporator because deoxidation can be efficiently performed. As such an apparatus, for example, a cylindrical vertical fixed blade type centrifugal thin film evaporator is suitable.
反応物から分離回収されたグリセリドは、目的とするSO
Sファットを主成分とするものであるから、これをその
まま製品とし、またはこれを前記同様のエステル交換反
応に供してさらに高純度SOSファットとすることもでき
る。The glyceride separated and recovered from the reaction product is the target SO
Since S fat is the main component, it can be used as a product as it is, or it can be subjected to the same transesterification reaction as described above to obtain a higher purity SOS fat.
一方、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プもしくはこ
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素添加を行う。水素添加反応
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ないステアリン酸を得る。On the other hand, the separated and recovered mixed fatty acid can be hydrogenated by an autoclave used for hydrogenation reaction of general animal and vegetable oils and fats or an apparatus having a function equivalent to this. The conditions are not particularly limited, but hydrogenation is performed until all the oleic acid is converted to stearic acid. After the hydrogenation reaction, the catalyst and a trace amount of fatty acid soap are removed, and therefore citric acid or the like is usually added to obtain stearic acid by filtration.
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 for reuse as stearic acid which is a raw material for the first 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、加温融解した後、水を飽和させた（70℃）。
これを、固定化リパーゼ20gを充填し68℃に保ったカラ
ムに通してエステル交換反応を行った。得られた反応物
は約1,000gの混合脂肪酸を含む。反応物500gを2lのガラ
ス製蒸留装置で常法により処理し、グリセリドと脂肪酸
とを各々分離回収した。(E) Examples Example 1 1,000 g of oleic sunflower oil to 1,000 g of stearic acid
Were mixed, heated and melted, and then saturated with water (70 ° C.).
This was passed through a column filled with 20 g of immobilized lipase and kept at 68 ° C. for transesterification reaction. The resulting reaction product contains about 1,000 g of mixed fatty acids. 500 g of the reaction product was treated with a 2 liter glass distillation apparatus by a conventional method to separate and collect glyceride and fatty acid.
回収したグリセリドの組成をGLC分析により求めたとこ
ろ、トリグリセリド:96％、ジグリセリド:4％であり、
トリグリセリドはSOSを多量に含有するものであった。When the composition of the collected glyceride was determined by GLC analysis, it was 96% for triglyceride and 4% for diglyceride.
The triglyceride contained a large amount of SOS.
以上の操作を計４回行い、得られた脂肪酸を一括し4l型
オートクレーブで水素添加を行った。条件は、温度180
℃、H2圧1.5kg/cm2、攪拌300rpm、触媒ニッケル系0.2％
（対仕込原料）、時間1.5時間、触媒濾別時使用クエン
酸（粉末）0.3％である。The above operation was performed 4 times in total, and the fatty acids obtained were collectively hydrogenated in a 4 l type autoclave. Conditions are temperature 180
℃, H 2 pressure 1.5kg / cm 2 , stirring 300rpm, catalytic nickel 0.2%
(To the charged raw material), time is 1.5 hours, and citric acid (powder) used in filtering the catalyst is 0.3%.
水素添加物を分析の結果、脂肪酸中のステアリン酸含量
はほぼ100％であった。As a result of analyzing the hydrogenated product, the content of stearic acid in the fatty acid was almost 100%.
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, and the result was no different from that of stearic acid used first.
比較例１ 実施例１で用いたオレイックひまわり油1,000gおよびス
テアリン酸1,000gを混合し、70℃に加温融解した後、減
圧乾燥して水分含量を0.03重量％とした。これを実施例
１と同様に処理してエステル交換反応させ、グリセリド
と脂肪酸とを分離回収した。このグリセリドは原料オレ
イックひまわり油成分を主体とし、SOSは微量であっ
た。Comparative Example 1 1,000 g of the oleic sunflower oil used in Example 1 and 1,000 g of stearic acid were mixed, heated and melted at 70 ° C., and dried under reduced pressure to a water content of 0.03% by weight. This was treated in the same manner as in Example 1 to cause a transesterification reaction, and glyceride and fatty acid were separated and recovered. This glyceride consisted mainly of the raw oleic sunflower oil component, and the SOS content was very small.
（ｆ）発明の効果 本発明によれば、SOS成分を含まない油脂原料から、副
反応物を生じることなく、SOSファットを多量に含むエ
ステル交換油脂が得られる。また、エステル交換反応に
よりSOSファッ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、
これはが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ファットの製造にあたってはス
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よ
い。これは製造コスト面での利点が極めて大きく、SOS
ファットの製造費を大幅に低減できる。(F) Effect of the Invention According to the present invention, a transesterified oil and fat containing a large amount of SOS fat can be obtained from an oil and fat raw material containing no SOS component without producing a side reaction product. Further, although the mixed fatty acid generated in the step of producing SOS fat by the transesterification reaction contains oleic acid once, according to the present invention,
This is returned to stearic acid by the elementary addition reaction and reused.Therefore, in the production of SOS fat, the stearic acid needs to be replenished by the loss produced in each step, and new stearic acid is prepared each time the reaction is performed. You don't have to. This is extremely advantageous in terms of manufacturing cost, and SOS
The fat manufacturing cost can be significantly reduced.
Claims (1)
かつパルミチン酸およびステアリン酸を実質的に含まな
い油脂とステアリン酸とを、予め70℃に加温融解して水
分を飽和させ、これを固定化1,3特異性リパーゼを充填
したカラムに流してエステル交換反応させ、該反応物か
ら脱酸回収したステアリン酸および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 high content of oleic acid as a constituent fatty acid,
In addition, fat and stearic acid substantially free of palmitic acid and stearic acid and stearic acid are heated and melted at 70 ° C in advance to saturate the water, and this is passed through a column packed with immobilized 1,3 specific lipase. A mixture of stearic acid and oleic acid, which have been subjected to transesterification and deoxidized and recovered from the reaction product, is converted into stearic acid by hydrogenation, and this is used as stearic acid as a raw material for the transesterification reaction. A method for producing 3,3-distearo-2-olein.
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 JPS62272982A (en) | 1987-11-27 |
| JPH0783718B2 true 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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7442531B2 (en) | 2003-07-09 | 2008-10-28 | The Nisshin Oillio Group, Ltd. | Method for producing symmetric triglycerides |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0631396B2 (en) * | 1986-05-21 | 1994-04-27 | 日清製油株式会社 | Method for producing transesterified oils and fats |
| WO2003000832A1 (en) * | 2001-06-26 | 2003-01-03 | Fuji Oil Company, Limited | Process for producing processed glyceride fat |
| GB2490324B (en) * | 2011-04-21 | 2014-06-11 | Desmet Ballestra Engineering S A Nv | Improved enzyme interesterification process |
Citations (2)
| 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 |
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE54838B1 (en) * | 1982-04-30 | 1990-02-28 | Unilever Plc | Improvements in and relating to interesterification of triglycerides of fatty acids |
-
1986
- 1986-05-21 JP JP61118339A patent/JPH0783718B2/en not_active Expired - Lifetime
Patent Citations (2)
| 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 |
| 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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7442531B2 (en) | 2003-07-09 | 2008-10-28 | The Nisshin Oillio Group, Ltd. | Method for producing symmetric triglycerides |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62272982A (en) | 1987-11-27 |
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