JP2763789B2 - Modification method of hardened oil - Google Patents
Modification method of hardened oilInfo
- Publication number
- JP2763789B2 JP2763789B2 JP1168093A JP16809389A JP2763789B2 JP 2763789 B2 JP2763789 B2 JP 2763789B2 JP 1168093 A JP1168093 A JP 1168093A JP 16809389 A JP16809389 A JP 16809389A JP 2763789 B2 JP2763789 B2 JP 2763789B2
- Authority
- JP
- Japan
- Prior art keywords
- oil
- weight
- hardened
- hardened oil
- reaction
- 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 - Fee Related
Links
- 238000002715 modification method Methods 0.000 title description 2
- 102000004882 Lipase Human genes 0.000 claims description 16
- 108090001060 Lipase Proteins 0.000 claims description 16
- 239000004367 Lipase Substances 0.000 claims description 16
- 235000019421 lipase Nutrition 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 14
- 238000002844 melting Methods 0.000 claims description 12
- 230000008018 melting Effects 0.000 claims description 12
- 238000005809 transesterification reaction Methods 0.000 claims description 10
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 9
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 235000021314 Palmitic acid Nutrition 0.000 claims description 7
- 235000021355 Stearic acid Nutrition 0.000 claims description 7
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 7
- 239000008117 stearic acid Substances 0.000 claims description 7
- 239000003921 oil Substances 0.000 description 63
- 235000019198 oils Nutrition 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000002255 enzymatic effect Effects 0.000 description 4
- 235000013310 margarine Nutrition 0.000 description 4
- 239000003495 polar organic solvent Substances 0.000 description 4
- 150000003626 triacylglycerols Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 235000019485 Safflower oil Nutrition 0.000 description 3
- 235000019486 Sunflower oil Nutrition 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000002407 reforming Methods 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 235000005713 safflower oil Nutrition 0.000 description 3
- 239000003813 safflower oil Substances 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000002600 sunflower oil Substances 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 241000235527 Rhizopus Species 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 235000021323 fish oil Nutrition 0.000 description 2
- 230000003100 immobilizing effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-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 compound 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
- 241000588986 Alcaligenes Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000303962 Rhizopus delemar Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000010495 camellia oil Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 102220229106 rs753340463 Human genes 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、酵素的エステル交換反応による硬化油の改
質方法に関し、詳しくはジグリセライド及び３飽和トリ
グリセライドの生成の少ない、硬化油の改質方法に関す
る。Description: TECHNICAL FIELD The present invention relates to a method for reforming a hardened oil by an enzymatic transesterification reaction, and more particularly, to a method for reforming a hardened oil with less generation of diglyceride and trisaturated triglyceride. About.
油脂の硬化は、液状油等を使用目的に適した硬度とす
るために重要なプロセスであり、硬化により得られた硬
化油は、使用目的に応じて様々な物性、例えば、稠度、
結晶性等を改質して広範な用途に利用されている。The hardening of fats and oils is an important process for obtaining a liquid oil or the like having a hardness suitable for the purpose of use, and the hardened oil obtained by hardening has various physical properties depending on the purpose of use, for example, consistency,
It is used for a wide range of applications by modifying its crystallinity.
従来より硬化油の改良方法としてはアルカリ金属触媒
（ナトリウムメチラート等）を使用したランダムエステ
ル交換法があり、硬化油の結晶性や伸展性等の物理特性
を改良する方法として広く利用されている。Conventionally, there has been a random transesterification method using an alkali metal catalyst (such as sodium methylate) as a method for improving a hardened oil, and is widely used as a method for improving physical properties such as crystallinity and extensibility of a hardened oil. .
しかしながら、このような公知の方法は、次の様な欠
点があった。However, such known methods have the following disadvantages.
グリセライドの脂肪酸の位置に対する選択性が無く、
３飽和トリグリセライドが多く生成する。Lack of selectivity for glyceride fatty acid position,
A large amount of trisaturated triglyceride is produced.
反応前に触媒毒となる水や脂肪酸の除去等の前処理が
必要である。Prior to the reaction, pretreatment such as removal of water and fatty acids which are poisons of the catalyst is required.
反応を化学触媒下高温で行う為、不飽和脂肪酸の熱的
な変性劣化が起こる。Since the reaction is performed at a high temperature in the presence of a chemical catalyst, thermal denaturation and degradation of unsaturated fatty acids occurs.
反応終了後の触媒除去は、水や酸等で洗浄する必要が
あるため、油脂の加水分解によりジグリセライドが生成
する。Since the removal of the catalyst after the completion of the reaction requires washing with water, an acid or the like, diglyceride is generated by hydrolysis of the fat or oil.
従って、本発明の目的は、硬化油の前処理を必要とせ
ず、不飽和脂肪酸の熱劣化も少なく、ジグリセライド及
び３飽和トリグリセライドの生成を抑制し、硬化油の結
晶性や伸展性を向上させ、食用とした時の食感や口溶け
も良好である硬化油を得ることのできる、硬化油の改質
方法を提供することにある。Accordingly, an object of the present invention is to eliminate the need for pretreatment of a hardened oil, reduce the thermal degradation of unsaturated fatty acids, suppress the production of diglycerides and trisaturated triglycerides, improve the crystallinity and extensibility of the hardened oil, It is an object of the present invention to provide a method for modifying a hardened oil, which can obtain a hardened oil having good texture and dissolution in the mouth when used as food.
本発明者等は、前記目的を、パルミチン酸含量25重量
％以下、且つステアリン酸含量15重量％以下で、融点が
28℃〜42℃である硬化油100重量部に対し、不飽和脂肪
酸含量80重量％以上の液状油を５〜40重量部配合し、1,
3位特異性を有するリパーゼと接触させてエステル交換
反応を行うことを特徴とする硬化油の改質方法を提供す
ることにより達成したものである。The present inventors have aimed at the above-mentioned object with a palmitic acid content of 25% by weight or less, a stearic acid content of 15% by weight or less, and a melting point of
To 100 parts by weight of hardened oil at 28 ° C to 42 ° C, 5 to 40 parts by weight of a liquid oil having an unsaturated fatty acid content of 80% by weight or more is blended.
The present invention has been achieved by providing a method for modifying a hardened oil, which comprises performing a transesterification reaction by contacting with a lipase having 3-position specificity.
以下、本発明の硬化油の改質方法について詳述する。 Hereinafter, the method for modifying a hardened oil of the present invention will be described in detail.
本発明の改質方法の対象とされる硬化油は、パルミチ
ン酸含量が25重量％以下、好ましくは10〜25重量％で、
且つステアリン酸含量が15重量％以下、好ましくは５〜
15重量％であるように水素添加して融点を28℃〜42℃、
好ましくは28℃〜40℃とした硬化油であればどのような
種類のものでも良く、例えば、大豆油、菜種油、トウモ
ロコシ油、米油、魚油等の硬化油を使用することができ
る。The hardened oil targeted by the modification method of the present invention has a palmitic acid content of 25% by weight or less, preferably 10 to 25% by weight,
And a stearic acid content of 15% by weight or less, preferably 5 to 5%.
The melting point is 28 ° C to 42 ° C by hydrogenation so as to be 15% by weight,
Any type of hardened oil, preferably at 28 ° C. to 40 ° C., may be used. For example, hardened oils such as soybean oil, rapeseed oil, corn oil, rice oil, and fish oil can be used.
パルミチン酸含量又はステアリン酸含量が上記量を超
える場合、或いは融点が42℃を超える場合は、食用に供
した時の口溶けが悪く、又、融点が28℃を下回ると、伸
展性の悪いものとなってしまう。If the palmitic acid content or stearic acid content exceeds the above amount, or if the melting point exceeds 42 ° C, the dissolution in the mouth when served for food is poor, and if the melting point is lower than 28 ° C, the extensibility is poor. turn into.
本発明で用いられる液状油は、不飽和脂肪酸含量80重
量％以上、好ましくは80〜95重量％の液状油であれば、
天然に存在するものでも合成されたものでも良く、例え
ば、大豆油、菜種油、トウモロコシ油、米油、ハイオレ
イックヒマワリ油、オリーブ油、茶油、ヒマワリ油、サ
フラワー油、ハイオレイックサフラワー油等を使用する
ことができる。The liquid oil used in the present invention is a liquid oil having an unsaturated fatty acid content of 80% by weight or more, preferably 80 to 95% by weight,
It may be naturally occurring or synthetic, for example, soybean oil, rapeseed oil, corn oil, rice oil, high oleic sunflower oil, olive oil, tea oil, sunflower oil, safflower oil, high oleic saflower oil Etc. can be used.
本発明においては、上記硬化油と上記液状油を、上記
硬化油100重量部に対し、上記液状油５〜40重量部、好
ましくは５〜30重量部の割合で配合する。In the present invention, the hardened oil and the liquid oil are blended at a ratio of 5 to 40 parts by weight, preferably 5 to 30 parts by weight of the liquid oil with respect to 100 parts by weight of the hardened oil.
液状油が上記量以下では伸展性を向上させる効果が不
十分であり、上記量以上であると結晶性が消失する。When the amount of the liquid oil is less than the above amount, the effect of improving the extensibility is insufficient, and when the amount is more than the above amount, the crystallinity is lost.
本発明においては、この配合油を1,3位特異性を有す
るリパーゼを触媒としてエステル交換反応を行う。In the present invention, this oil mixture is subjected to a transesterification reaction using a lipase having 1,3-position specificity as a catalyst.
本発明で用いられるリパーゼとしては、リゾープス
（Rhizopus）属、アスペルギルス（Aspergillus）属、
ムコール（Mucor）属、ペニシリウム（Penicillium）
属、アルカリゲネス（Alcaligenes）属の属する微生物
が生産するリパーゼを使用することができ、また少なく
ともこれらと同等の性質を有するリパーゼであれば、上
記リパーゼの化学修飾物でも、合成されたものでも良
く、何ら差し支えない。The lipase used in the present invention includes genus Rhizopus, genus Aspergillus,
Mucor, Penicillium
A lipase produced by a microorganism belonging to the genus Alcaligenes can be used, and any lipase having at least the same properties as these may be a chemically modified product of the lipase or a synthesized lipase. No problem.
上記リパーゼの使用形態は、特に限定されないが、効
率の点からは、公知の方法で担体に固定化して使用する
ことが好ましく、特に、本発明における反応系で不溶且
つ酵素活性に悪影響を与えない担体に固定化して使用す
ることが好ましい。The use form of the lipase is not particularly limited, but from the viewpoint of efficiency, it is preferable to use the lipase by immobilizing it on a carrier by a known method, and in particular, it is insoluble in the reaction system of the present invention and does not adversely affect enzyme activity. It is preferable to use by immobilizing on a carrier.
上記担体としては、例えば、セライト、アルミナ、イ
オン交換樹脂、キトサン等を挙げることができ、これら
は単独又は組み合わせて使用することができる。Examples of the carrier include celite, alumina, ion exchange resin, chitosan and the like, and these can be used alone or in combination.
上記リパーゼの使用量は、反応条件や希望する硬化油
の性質に応じて適宣決定すれば良く、特に制限されるも
のではないが、例えばバッチ式の場合は油脂100gに対し
て概ね0.05〜50g、好ましくは0.1〜20g程度とすれば良
く、連続式の場合は空筒速度（原料流量／固定化リパー
ゼ容積:h-1）が概ね0.1〜20h-1、好ましくは0.2〜10h-1
となる量とすれば良い。The amount of the lipase to be used may be appropriately determined depending on the reaction conditions and the properties of the desired hardened oil, and is not particularly limited.For example, in the case of a batch system, approximately 0.05 to 50 g per 100 g of fat or oil is used. In the case of a continuous type, the cylinder speed (raw material flow rate / immobilized lipase volume: h -1 ) is generally about 0.1 to 20 h -1 , preferably 0.2 to 10 h -1.
The amount may be set to
本発明における酵素的エスレル交換反応は、非極性有
機溶剤の存在しない系でも、存在する系でも行うことが
でき、硬化油の種類や目的とする物性に応じてフレキシ
ブルに対応することができるが、エステル交換が非極性
有機溶剤の存在に無関係の場合は、非極性有機溶剤の存
在しない系で行うと経済性及び工業化適性の点で好まし
い。The enzymatic esrel exchange reaction in the present invention can be performed in a system in which a non-polar organic solvent is not present, or in a system in which a non-polar organic solvent is present, and can flexibly respond to the type of hardened oil and the desired physical properties. When the transesterification is irrelevant to the presence of the non-polar organic solvent, it is preferable to perform the transesterification in a system free of the non-polar organic solvent from the viewpoint of economic efficiency and industrial applicability.
本発明における酵素的エステル交換反応は、30℃〜50
℃の温度で行うのが良く、より好ましくは35〜50℃の温
度で行うのが良い。The enzymatic transesterification in the present invention is performed at 30 ° C to 50 ° C.
C., and more preferably at a temperature of 35 to 50.degree.
上記温度より低いと粘度上昇や固化等の点で好ましく
なく、又上記温度より高いと酵素活性の低下及びトリグ
リセライドのアシル転移により改質効果が減少する。If the temperature is lower than the above-mentioned temperature, viscosity increase and solidification are not preferable. If the temperature is higher than the above-mentioned temperature, the enzyme activity decreases and the acyl transfer of triglyceride reduces the reforming effect.
又、反応時間は、バッチ式の場合、通常１時間〜３日
間、好ましくは３〜24時間程度とすれば良い。又、連続
式の場合の反応時間は、前記空筒速度を選定することに
より規定される。In the case of a batch system, the reaction time is usually 1 hour to 3 days, preferably about 3 to 24 hours. The reaction time in the case of the continuous type is defined by selecting the above-mentioned cylinder speed.
本発明における酵素的エステル交換反応は、バッチ式
で行っても良いが、連続式で行うとトリグリセライドの
アシル転移が少なく、又作業性の点で好ましい。The enzymatic transesterification in the present invention may be carried out in a batch system, but is preferably carried out in a continuous system since the acyl transfer of triglyceride is small and the workability is low.
以下に実施例を挙げ本発明をさらに説明するが、本発
明はこれらに限定されるものではない。Hereinafter, the present invention will be further described with reference to Examples, but the present invention is not limited thereto.
実施例１ 魚硬化油（融点36.4℃、ヨウ素価77.6、パルミチン酸
含量18.8重量％、ステアリン酸含量5.8重量％）100重量
部に、ハイオレイックヒマワリ油（不飽和脂肪酸含量9
2.6重量％）20重量部を混合した。Example 1 100 parts by weight of a hardened fish oil (melting point: 36.4 ° C., iodine value: 77.6, palmitic acid content: 18.8% by weight, stearic acid content: 5.8% by weight) were mixed with high oleic sunflower oil (unsaturated fatty acid content: 9
2.6 parts by weight) were mixed.
特開昭59−213390号公報に記載の方法に従って調製し
た、キトサン−セライト複合担体100gにリゾープスデレ
マーリパーゼ（生化学工業製：リゾープス属起源）5.15
gを吸着固定化した固定化リパーゼ20gを充填したカラム
（直径2.0cm×全長25cm）に、前記混合油を流量25ml/時
（空筒速度0.32h-1）で供給し、温度45℃で反応させ、
常法により脱臭した。5.15 g of Rhizopus delemar lipase (manufactured by Seikagaku Corporation, origin of Rhizopus) prepared on 100 g of chitosan-celite composite carrier prepared according to the method described in JP-A-59-213390.
The mixed oil was supplied at a flow rate of 25 ml / h (cylinder speed of 0.32 h -1 ) to a column (2.0 cm in diameter x 25 cm in total length) packed with 20 g of immobilized lipase on which g had been adsorbed and immobilized. Let
Deodorized by a conventional method.
反応前の混合油及び反応後の生成油の融点（基準油脂
分析試験法２・３・４・２−72に従って測定）及び、SF
C〔American Oil Chemical Society Recomended P
ractice Cd16−18 Solid Fat Contentに従って、PR
AXIS MODEL SFC−900（プラクシス社製）を使用して
測定〕を測定した。The melting points of the mixed oil before the reaction and the product oil after the reaction (measured in accordance with the standard fats and oils analysis test method 2, 3, 4, 2, 72) and SF
C (American Oil Chemical Society Recomended P
practice Cd16-18 According to Solid Fat Content, PR
Measurement using AXIS MODEL SFC-900 (manufactured by Praxis).
その結果を下記表−１に示す。 The results are shown in Table 1 below.
実施例２ 大豆硬化油（融点34.0℃、ヨウ素価74.5、パルミチン
酸含量10.3重量％、ステアリン酸含量7.7重量％）100重
量部に、ハイオレイックサフラワー油（不飽和脂肪酸含
量91.1重量％）10重量部を混合した。Example 2 100 parts by weight of hardened soybean oil (melting point: 34.0 ° C., iodine value: 74.5, palmitic acid content: 10.3% by weight, stearic acid content: 7.7% by weight) were mixed with 10 parts of high oleic safflower oil (91.1% by weight of unsaturated fatty acid). Parts by weight were mixed.
リポザイム−IM20（NOVO社製固定化リパーゼ）20gを
充填したカラム（直径2.0cm×全長25cm）に、前記混合
油を流量30mml/時（空筒速度0.38h-1）で供給し、温度4
5℃で反応させ、常法により脱臭した。The mixed oil was supplied to a column (2.0 cm in diameter x 25 cm in total length) packed with 20 g of Lipozyme-IM20 (immobilized lipase manufactured by NOVO) at a flow rate of 30 mml / h (vacuum speed 0.38 h -1 ).
The reaction was carried out at 5 ° C. and deodorized by a conventional method.
反応前の混合油及び反応後の生成油の融点及び、SFC
を実施例１と同様に測定した。Melting point of mixed oil before and after reaction, and SFC
Was measured in the same manner as in Example 1.
その結果を下記表−１に示す。 The results are shown in Table 1 below.
実施例３ 米硬化油（融点40.0℃、ヨウ素価62.7、パルチミン酸
含量16.3重量％、ステアリン酸含量13.6重量％）100重
量部に、ハイオレイックサフラワー油（不飽和脂肪酸含
量91.1重量％）20重量部を混合した。Example 3 100 parts by weight of rice hardened oil (melting point: 40.0 ° C, iodine value: 62.7, content of palmitic acid: 16.3% by weight, content of stearic acid: 13.6% by weight) were mixed with 20 parts of high oleic safflower oil (91.1% by weight of unsaturated fatty acid). Parts by weight were mixed.
リポザイム−IM20（NOVO社製固定化リパーゼ）20gを
充填したカラム（直径2.0cm×全長25cm）に、前記混合
油を流量30ml/時（空筒速度0.38h-1）で供給し、温度45
℃で反応させ、常法により脱臭した。The mixed oil was supplied at a flow rate of 30 ml / hour (empty cylinder speed of 0.38 h -1 ) to a column (2.0 cm in diameter × 25 cm in total length) packed with 20 g of lipozyme-IM20 (immobilized lipase manufactured by NOVO) at a temperature of 45
The reaction was carried out at 0 ° C and deodorized by a conventional method.
反応前の混合油及び反応後の生成油の融点及び、SFC
を実施例１と同様に測定した。Melting point of mixed oil before and after reaction, and SFC
Was measured in the same manner as in Example 1.
その結果を下記表−１に示す。 The results are shown in Table 1 below.
比較例１ 実施例１で使用した混合油をアルカリ脱酸した油1kg
を減圧下100℃で脱水後、温度を85℃に下げ、ナトリウ
ムメチラートを油脂に対して0.15重量％添加し、減圧下
80〜85℃で60分間エステル交換反応させた。Comparative Example 1 1 kg of oil obtained by alkali deoxidizing the mixed oil used in Example 1
Was dehydrated at 100 ° C under reduced pressure, the temperature was lowered to 85 ° C, and sodium methylate was added in an amount of 0.15% by weight based on the fat and oil.
The transesterification was performed at 80 to 85 ° C for 60 minutes.
反応生成油を湯洗、脱水、漂白、脱臭を行い、実施例
１と同様な分析を行った。The reaction product oil was washed with hot water, dehydrated, bleached, and deodorized, and analyzed in the same manner as in Example 1.
その結果を下記表−１に示す。 The results are shown in Table 1 below.
比較例２ 実施例２で使用した混合油を比較例１と同様に処理
し、得られた反応生成油について実施例１と同様な分析
を行った。Comparative Example 2 The mixed oil used in Example 2 was treated in the same manner as in Comparative Example 1, and the obtained reaction product oil was analyzed in the same manner as in Example 1.
その結果を下記表−１に示す。 The results are shown in Table 1 below.
比較例３ 実施例３で使用した混合油を比較例１と同様に処理
し、得られた反応生成油について実施例１と同様な分析
を行った。Comparative Example 3 The mixed oil used in Example 3 was treated in the same manner as in Comparative Example 1, and the obtained reaction product oil was analyzed in the same manner as in Example 1.
その結果を下記表−１に示す。 The results are shown in Table 1 below.
また、実施例１〜３及び比較例１〜３の各反応生成油
のトリグリセライド組成は下記表−２に示す通りであっ
た。〔分析法：油化学 34（１）,36（1985）鎌田恒夫
のTLC−FID法に準じた〕。 The triglyceride compositions of the reaction product oils of Examples 1 to 3 and Comparative Examples 1 to 3 were as shown in Table 2 below. [Analytical method: According to TLC-FID method of Oil Chemistry 34 (1), 36 (1985) Tsuneo Kamada].
表−１及び表−２から明らかな通り、実施例の反応生
成油は何れも、対応する比較例の反応生成油よりも高融
点部（S3）の少ないものであった。 As is clear from Tables 1 and 2, the reaction product oil of each of the examples had a lower melting point (S 3 ) than the corresponding reaction product oil of the comparative example.
又、実施例１〜３及び比較例１〜３の各反応生成油を
使用して、下記表−３に示す配合でマーガリンを試作
し、これらのマーガリンについて下記表−４に示す組合
せで官能試験を実施したところ、結果は下記表−４に示
す通りであり、10人中７人以上が実施例の反応生成油を
用いたマーガリンは何れも比較例の反応生成油を用いた
マーガリンに比べて良好な食感でありザラツキが無いと
いう結果であり、本発明の方法により改質された油脂は
良好な結晶性及び伸展性を有しているものであった。Also, using the reaction product oils of Examples 1 to 3 and Comparative Examples 1 to 3, margarines were trial-produced in the composition shown in Table 3 below, and the sensory test was performed on these margarines in combinations shown in Table 4 below. Was carried out, the results are as shown in Table 4 below, and 7 or more of 10 margarines using the reaction product oil of the example were compared with the margarines using the reaction product oil of the comparative example. The result was a good texture and no graininess, and the oils and fats modified by the method of the present invention had good crystallinity and extensibility.
又、実施例１〜３の各反応生成油は何れも、クリーミ
ング性、乳化分散性、吸水性等も良好であった。In addition, each of the reaction product oils of Examples 1 to 3 also had good creaming properties, emulsifying and dispersing properties, and water absorption.
〔発明の効果〕 本発明の硬化油の改質方法によれば、硬化油を前処理
することなく、不飽和脂肪酸の熱劣化も少なく、ジグリ
セライド及び３飽和トリグリセライドの生成を抑制し、
硬化油の結晶性や伸展性を向上させ、食用とした時の食
感や口溶けも良好である硬化油を得ることができる。 [Effects of the Invention] According to the method for modifying a hardened oil of the present invention, without pre-treating the hardened oil, the thermal degradation of unsaturated fatty acids is reduced, and the production of diglyceride and trisaturated triglyceride is suppressed,
It is possible to improve the crystallinity and extensibility of the hardened oil and obtain a hardened oil having good texture and dissolution in the mouth when used as food.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 松本 渉 東京都荒川区東尾久７丁目２番35号 旭 電化工業株式会社内 (58)調査した分野(Int.Cl.6，ＤＢ名) C12P 7/64 A23D 7/00──────────────────────────────────────────────────続 き Continuation of the front page (72) Wataru Matsumoto 7-35, Higashiogu, Arakawa-ku, Tokyo Asahi Denka Kogyo Co., Ltd. (58) Investigated field (Int. Cl. 6 , DB name) C12P 7 / 64 A23D 7/00
Claims (1)
アリン酸含量15重量％以下で、融点が28℃〜42℃である
硬化油100重量部に対し、不飽和脂肪酸含量80重量％以
上の液状油を５〜40重量部配合し、1,3位特異性を有す
るリパーゼと接触させてエステル交換反応を行うことを
特徴とする硬化油の改質方法。A liquid having an unsaturated fatty acid content of 80% by weight or more based on 100 parts by weight of a hardened oil having a palmitic acid content of 25% by weight or less and a stearic acid content of 15% by weight or less and a melting point of 28 ° C to 42 ° C. A method for modifying a hardened oil, comprising mixing 5 to 40 parts by weight of an oil, and bringing the oil into contact with a lipase having 1,3-position specificity to carry out a transesterification reaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1168093A JP2763789B2 (en) | 1989-06-29 | 1989-06-29 | Modification method of hardened oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1168093A JP2763789B2 (en) | 1989-06-29 | 1989-06-29 | Modification method of hardened oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0330686A JPH0330686A (en) | 1991-02-08 |
| JP2763789B2 true JP2763789B2 (en) | 1998-06-11 |
Family
ID=15861717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1168093A Expired - Fee Related JP2763789B2 (en) | 1989-06-29 | 1989-06-29 | Modification method of hardened oil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2763789B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5153040B2 (en) * | 2001-08-23 | 2013-02-27 | 株式会社Ａｄｅｋａ | Oil composition for frying or spraying |
| DE102014118400B4 (en) | 2014-12-11 | 2016-08-11 | Kautex Textron Gmbh & Co. Kg | Filling system on a motor vehicle with at least two storage tanks for liquid or gaseous fuels |
| CN112048380B (en) * | 2020-09-03 | 2022-06-14 | 广州白云山汉方现代药业有限公司 | Method for accurately controlling stearic acid content in soybean oil by adopting mixed filler |
-
1989
- 1989-06-29 JP JP1168093A patent/JP2763789B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0330686A (en) | 1991-02-08 |
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