JP5720113B2 - Production method of solid fat - Google Patents
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- JP5720113B2 JP5720113B2 JP2010099122A JP2010099122A JP5720113B2 JP 5720113 B2 JP5720113 B2 JP 5720113B2 JP 2010099122 A JP2010099122 A JP 2010099122A JP 2010099122 A JP2010099122 A JP 2010099122A JP 5720113 B2 JP5720113 B2 JP 5720113B2
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- 239000007787 solid Substances 0.000 title claims description 70
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- 239000003925 fat Substances 0.000 claims description 138
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 80
- 239000003921 oil Substances 0.000 claims description 80
- 125000005456 glyceride group Chemical group 0.000 claims description 47
- 235000021314 Palmitic acid Nutrition 0.000 claims description 40
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 40
- 238000005809 transesterification reaction Methods 0.000 claims description 39
- 238000005194 fractionation Methods 0.000 claims description 20
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 19
- 239000011630 iodine Substances 0.000 claims description 19
- 239000002994 raw material Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 11
- 229930195729 fatty acid Natural products 0.000 claims description 11
- 239000000194 fatty acid Substances 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 239000013078 crystal Substances 0.000 claims description 9
- 239000000470 constituent Substances 0.000 claims description 7
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 claims description 6
- 125000005313 fatty acid group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
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- 239000000203 mixture Substances 0.000 description 16
- 235000019482 Palm oil Nutrition 0.000 description 15
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- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 12
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- 150000004665 fatty acids Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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- 230000003247 decreasing effect Effects 0.000 description 8
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
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- 244000299461 Theobroma cacao Species 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000005457 triglyceride group Chemical group 0.000 description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 235000013310 margarine Nutrition 0.000 description 2
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- 238000002844 melting Methods 0.000 description 2
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- 239000003094 microcapsule Substances 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 1
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910000574 NaK Inorganic materials 0.000 description 1
- 108010084311 Novozyme 435 Proteins 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 239000000828 canola oil Substances 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 238000004817 gas chromatography Methods 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000021243 milk fat Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
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- 238000004904 shortening Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
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- 239000008117 stearic acid Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008256 whipped cream Substances 0.000 description 1
Landscapes
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
Description
本発明は、固体脂の製造法及び固体脂に関する。 The present invention relates to a method for producing solid fat and solid fat.
パーム油は、酸化安定性が高く、価格競争力もあることから、年々生産量が増加している。そのため、パ−ム油を原料として、マーガリン、チョコレート、ホイップクリームなどの加工油脂食品やサラダ油などの液状油脂など様々な用途で利用されおり、今後更なる利用の拡大が予想される。そこで、パ−ム油を原料として液状油脂を作製する方法がいくつか提案されている（非特許文献１）。その際にろ別される固体脂は、構成脂肪酸としてパルミチン酸が多いものの、その殆どが１、３位に結合している。 Palm oil has high oxidation stability and is competitive in price, so its production volume is increasing year by year. For this reason, palm oil is used as a raw material for various uses such as processed fat and oil foods such as margarine, chocolate, and whipped cream, and liquid fats and oils such as salad oil, and further expansion of use is expected in the future. Thus, several methods for producing liquid oils and fats using palm oil as a raw material have been proposed (Non-Patent Document 1). Although the solid fat filtered off in that case has much palmitic acid as a constituent fatty acid, most of them are bonded to the 1st and 3rd positions.
一方、２位にパルミチン酸を有するグリセライドは、母乳の油脂成分に多く含まれるＯＰＯ（２−パルミトイル−１，３−ジオレイルトリグリセライド）構造の原料や、マーガリンやチョコレートの原料に利用されるＰＰＯ（１，２−ジパルミトイル−３−ジオレイルトリグリセライド）構造の原料になり、例えばオレイン酸と、トリパルミチン酸グリセライド（ＰＰＰ）のように２位にパルミチン酸を有するトリグリセライドとを１，３位特異的酵素などによって１，３位を特異的にエステル交換することで作製される。また、ＰＰＰを主とする油脂は、チョコレート油脂の原料やそのまま加工してマイクロカプセルの基材などにも利用されている。 On the other hand, glyceride having palmitic acid at the 2-position is a raw material having an OPO (2-palmitoyl-1,3-dioleyl triglyceride) structure, which is contained in a large amount of fat and oil components in breast milk, and PPO ( 1,2-dipalmitoyl-3-dioleyl triglyceride) structure, for example, oleic acid and triglyceride having palmitic acid at the 2-position such as tripalmitic acid glyceride (PPP) are specific to the 1,3-position It is produced by specific transesterification at positions 1 and 3 with an enzyme or the like. Further, fats and oils mainly composed of PPP are used as raw materials for chocolate fats and oils, processed as they are, and used as a base material for microcapsules.
２位にパルミチン酸を有するグリセライドを多く含む天然の油脂としては、ラードを挙げられるが、ラードは独特の獣臭が発現し、更に時間の経過と共に戻り臭が発生し、また宗教上の理由で使用が困難な場合があったり、といろいろな問題がある。そこで、植物油から２位にパルミチン酸を有するグリセライドを多く含む油脂の開発が望まれている。 Natural fats and oils containing a lot of glycerides with palmitic acid at the 2nd position include lard, but lard develops a unique animal odor, and a return odor develops over time, and for religious reasons There are various problems such as difficult to use. Therefore, development of fats and oils containing a large amount of glyceride having palmitic acid at the second position from vegetable oil is desired.
自然界に豊富にあるオレイン酸やリノール酸を多く含んだ油脂を水素添加して得られるステアリン酸を有するグリセライドを含む油脂とは異なり、パルミトオレイン酸などの炭素数１６の不飽和脂肪酸含量は自然界に極端に少ないため、天然原料を水素添加して２位にパルミチン酸を有するグリセリドを得ることは出来ない。 Unlike fats and oils containing glycerides with stearic acid obtained by hydrogenation of fats and oils rich in oleic acid and linoleic acid that are abundant in nature, the content of unsaturated fatty acids having 16 carbon atoms such as palmitooleic acid is Therefore, it is not possible to obtain a glyceride having palmitic acid at the 2-position by hydrogenating natural raw materials.
２位にパルミチン酸を有するグリセライド得る方法として、パルミチン酸の含量が多いが、２位にパルミチン酸を有するグリセライドが少ないパーム油を化学的にランダムエステル交換することで、２位のパルミチン酸含量を増加させる方法がある（特許文献１）が、この方法はランダムエステル交換のみで行われており、得られる２位にパルミチン酸を有するグリセライド含量も５８％が限界であった。 As a method of obtaining glyceride having palmitic acid at the 2-position, the palmitic acid content at the 2-position is obtained by chemically random transesterifying palm oil having a high palmitic acid content at the 2-position but less glyceride having palmitic acid at the 2-position. Although there is a method of increasing (Patent Document 1), this method is carried out only by random transesterification, and the obtained glyceride content having palmitic acid at the 2-position was limited to 58%.
高純度なＰＰＰを得る方法として、パーム油を原料として溶剤を用いて繰り返し分別する方法（特許文献２）がある。しかし、パーム油自体には構成脂肪酸としてパルミチン酸が多く含まれているものの、ＰＰＰの形としては多く含まれないため、高純度のＰＰＰを得るには溶剤を用いて繰り返し分別する必要があり、最終的に得られる収率も低く、また、溶剤を使用しているため溶剤を除去する必要があり生産性が悪い。また油脂中のＰＰＰ以外の油脂組成はＰＯＰやＰＯＯなど２位にパルミチン酸を含まないグリセライドが殆どであるため、油脂中の２位にパルミチン酸を有するグリセライドの含量は低い。 As a method for obtaining high-purity PPP, there is a method (Patent Document 2) in which palm oil is used as a raw material and is repeatedly fractionated using a solvent. However, although palm oil itself contains a large amount of palmitic acid as a constituent fatty acid, it does not contain much as the form of PPP, so it is necessary to repeatedly fractionate using a solvent to obtain high-purity PPP, The yield finally obtained is low, and since the solvent is used, it is necessary to remove the solvent, resulting in poor productivity. In addition, since the fat composition other than PPP in the fat is mostly glyceride containing no palmitic acid at the second position such as POP and POO, the content of glyceride having palmitic acid at the second position in the fat is low.
別の方法としてグリセリンとパルミチン酸のエステル合成反応により合成する方法もあるが、この方法は高純度なＰＰＰが得られるが純度の高い脂肪酸、グリセリンが必要であることや反応後に脂肪酸を除去する必要があるなど非常にコストがかかるといったデメリットがあった。 Another method is to synthesize by ester synthesis reaction of glycerin and palmitic acid, but this method can obtain high-purity PPP, but high-purity fatty acid, glycerin is necessary and it is necessary to remove the fatty acid after the reaction There was a demerit that it was very costly.
本発明の目的は、パーム系油脂から、２位にパルミチン酸を有するグリセライドを多く含有し、中でもトリパルミチン酸グリセライド（ＰＰＰ）を多く含む油脂を、安価で液状油脂と同時に製造する方法を提供することである。 An object of the present invention is to provide a method for producing a fat and oil containing a large amount of glyceride having palmitic acid at the 2-position from palm oil and containing a large amount of glyceride tripalmitate (PPP) at the same time as liquid oil and fat at a low cost. That is.
本発明者らは上記課題を解決するために鋭意研究を重ねた結果、ヨウ素価５５以上のパーム油脂を原料にしてダイレクトエステル交換反応を行ない、２位にパルミチン酸を有するグリセライドを増加させた後分別することで、２位にパルミチン酸を有するグリセライドを高含有する油脂を安価に得られることが出来ることを見出し、本発明を完成するに至った。 As a result of intensive studies to solve the above-mentioned problems, the present inventors conducted direct transesterification using palm oil having an iodine value of 55 or more as a raw material, and increased glyceride having palmitic acid at the 2-position. By separating, it was found that fats and oils containing a high content of glyceride having palmitic acid at the 2-position can be obtained at low cost, and the present invention has been completed.
即ち、本発明の第一は、ヨウ素価５５以上のパーム系油脂を原料にして得られる、固体脂全体中のトリパルミチン酸グリセライド含量が４５重量％以上、かつ、２位の構成脂肪酸がパルミチン酸であるグリセライドの含量が６５重量％以上である固体脂に関する。好ましい実施態様は、固体脂全体中のトリパルミチン酸グリセライド含量が６０重量％以上である上記記載の固体脂に関する。本発明の第二は、ヨウ素価５５以上のパーム系油脂を原料にし、エステル交換能を有した触媒下で油脂結晶を発生させながら１０℃〜４０℃でダイレクトエステル交換反応した後、液状油脂を分別除去することを特徴とする固体脂の製造方法に関する。好ましい実施態様は、反応物中のＳＳＳ含量が３１重量％を越えることなく、Ｓ２Ｕ含量が１４重量％以下になるまでダイレクトエステル交換反応を行ない、その後軟質部を分別除去することを特徴とする上記記載の固体脂の製造方法に関する。より好ましくは、ダイレクトエステル交換後の油脂を０〜４０℃で冷却結晶化し、その後乾式分別により軟質部を分別除去することを特徴とする上記記載の固体脂の製造方法、更に好ましくは、乾式分別温度が、０〜３０℃である上記記載の固体脂の製造方法、特に好ましくは、軟質部を乾式分別により分別除去して得た固体脂を、４０〜６０℃まで昇温した後、乾式分別により再び軟質部を除去することを特徴とする上記記載の固体脂の製造方法、に関する。 That is, the first of the present invention is obtained by using palm-based fats and oils having an iodine value of 55 or more as a raw material, the content of glyceride tripalmitate in the whole solid fat is 45% by weight or more , and the constituent fatty acid at the 2-position is palmitic acid. This relates to a solid fat having a glyceride content of 65% by weight or more . A preferred embodiment relates to the solid fat described above, wherein the content of glyceride tripalmitate in the whole solid fat is 60% by weight or more . In the second aspect of the present invention, palm oil or fat having an iodine value of 55 or more is used as a raw material, and after direct transesterification at 10 to 40 ° C. while generating oil or fat crystals under a catalyst having transesterification ability , The present invention relates to a method for producing a solid fat characterized by separating and removing. A preferred embodiment is characterized in that the direct transesterification is carried out until the S2U content becomes 14% by weight or less without the SSS content in the reaction product exceeding 31% by weight, and then the soft part is separated and removed. It relates to a method for producing the described solid fat. More preferably, the oil / fat after direct transesterification is cooled and crystallized at 0 to 40 ° C., and then the soft part is separated and removed by dry fractionation, and more preferably dry fractionation. The method for producing a solid fat as described above, wherein the temperature is from 0 to 30 ° C., particularly preferably, after the solid fat obtained by separating and removing the soft part by dry fractionation is heated to 40 to 60 ° C., then dry fractionation The method for producing a solid fat according to the above, wherein the soft part is removed again by the method described above.
本発明に従えば、パーム系油脂から２位にパルミチン酸を有するグリセライドを多く含有し、中でもトリパルミチン酸グリセライド（ＰＰＰ）を多く含む油脂を安価に製造する方法を提供することができる。 According to the present invention, it is possible to provide a method for inexpensively producing fats and oils containing a large amount of glyceride having palmitic acid at the 2-position from palm-based fats and oils, and especially containing a large amount of glyceride of tripalmitic acid (PPP).
以下、本発明につき、さらに詳細に説明する。本発明の固体脂は、パーム軟質油を原料にして、特定量のトリパルミチン酸グリセライドを含有することを特徴とする。なお、本発明におけるトリグリセライドの表記は以下の通りである。
ＳＳＳ：トリ飽和脂肪酸グリセライド
ＰＰＰ：トリパルミチン酸グリセライド
Ｓ２Ｕ：ジ飽和脂肪酸モノ不飽和脂肪酸グリセライド
Hereinafter, the present invention will be described in more detail. The solid fat of the present invention is characterized by containing a specific amount of glyceride tripalmitate using palm soft oil as a raw material. In addition, the description of the triglyceride in this invention is as follows.
SSS: Trisaturated fatty acid glyceride PPP: Tripalmitic acid glyceride S2U: Disaturated fatty acid monounsaturated fatty acid glyceride
本発明の固体脂におけるトリパルミチン酸グリセライド含量は、４５重量％以上が好ましく、６０重量％以上がより好ましい。トリパルミチン酸グリセライド含量が４５重量％未満であると、該固体脂を原料として２位の構成脂肪酸がパルミチン酸である油脂組成物を効率的に作製できない。そして、該固体脂全体中には、２位の構成脂肪酸がパルミチン酸であるグリセライドを６５重量％以上含有することが好ましい。６５重量％未満であると、該固体脂を原料として２位の構成脂肪酸がパルミチン酸である油脂組成物を効率的に作製できない場合がある。 The glyceride tripalmitate content in the solid fat of the present invention is preferably 45% by weight or more, and more preferably 60% by weight or more. If the content of tripalmitic acid glyceride is less than 45% by weight, an oil / fat composition in which the constituent fatty acid at position 2 is palmitic acid cannot be produced efficiently using the solid fat as a raw material. And it is preferable to contain 65 weight% or more of glycerides whose constituent fatty acid at the 2-position is palmitic acid in the whole solid fat. If it is less than 65% by weight, it may not be possible to efficiently produce an oil and fat composition in which the constituent fatty acid at the 2-position is palmitic acid using the solid fat as a raw material.
本発明の固体脂の製造方法は、特に限定はないが、例えば以下のようにすれば、パーム系油脂から２位にパルミチン酸を有するグリセライドを多く含有し、中でもＰＰＰを多く含む油脂を容易に安価で作製することができる。 The production method of the solid fat of the present invention is not particularly limited. For example, if it is as follows, it contains a large amount of glyceride having palmitic acid at the 2-position from palm-based fats and oils, and especially fats and fats that contain a large amount of PPP. It can be manufactured at low cost.
使用する原料としてはパーム系油脂が主であり、パーム系油脂としてはパーム精製油、未精製のクルード油および一回以上の分別によって得られた分画油が例示される。また、パーム系油脂のヨウ素価は５５以上であることが好ましい。ヨウ素価が５５未満の場合は、同時に作製されるパーム系油脂由来液状油脂の量が少なくなりすぎる場合がある。 Palm oils and fats are mainly used as raw materials, and examples of palm oils and fats include palm refined oil, unrefined crude oil, and fractionated oil obtained by one or more fractionations. Moreover, it is preferable that the iodine value of palm oil fat is 55 or more. If the iodine value is less than 55, the amount of palm-based oil-derived liquid oil produced at the same time may be too small.
本発明の固体脂の製造方法においては、原料油脂としてパーム系油脂以外の油脂をさらに用いても良い。但し、本発明の効果をより享受するためにはパーム系油脂以外の油脂の含有量は、原料油脂全体中５０重量％以下である。 In the manufacturing method of the solid fat of this invention, you may further use fats and oils other than palm oil fat as raw material fats and oils. However, in order to enjoy the effects of the present invention, the content of fats and oils other than palm-based fats and oils is 50% by weight or less in the total raw material fats and oils.
前記パーム系油脂以外の油脂としては、食用であれば特に限定はないが、大豆油、ナタネ油、ひまわり油、オリーブ油、ごま油、キャノーラ油、やし油、パーム核油、シア油、サル脂、イリッぺ脂、カカオ脂、牛脂、豚脂、乳脂、これらの油脂の分別脂、硬化油、エステル交換油などが挙げられる。 Oils and fats other than the palm oil and fat are not particularly limited as long as they are edible, but soybean oil, rapeseed oil, sunflower oil, olive oil, sesame oil, canola oil, palm oil, palm kernel oil, shea oil, monkey fat, Illippe fat, cacao fat, beef fat, pork fat, milk fat, fractionated fats of these fats, hardened oil, transesterified oil and the like can be mentioned.
そして、ヨウ素価５５以上のパーム系油脂を原料としたダイレクトエステル交換反応を、少なくとも反応中の油脂組成物中のＳＳＳ含量が３１重量％を越えることなく、Ｓ２Ｕ含量が１４重量％以下になり、反応を停止させるまで行うことが好ましく、その後液状油脂を分別除去することを特徴とする。前記を満たせば、ダイレクトエステル交換反応はどれだけ行っても良いが、コストを考え、前記を満たせば直ぐに停止させることが好ましい。ここでダイレクトエステル交換反応とは、エステル交換能を有した触媒下で油脂結晶を発生させながらエステル交換を行う反応のことである。本発明のダイレクトエステル交換反応の方法はバッチ式、連続式を問わない。 And, the direct transesterification reaction using palm-based fats and oils having an iodine value of 55 or more as a raw material, the SSS content in the fat composition during the reaction does not exceed 31 wt%, and the S2U content is 14 wt% or less, It is preferable to carry out until the reaction is stopped, and then liquid oil is removed by separation. If the above is satisfied, any number of direct transesterification reactions may be performed. However, considering the cost, it is preferable to stop the transesterification immediately if the above is satisfied. Here, the direct transesterification reaction is a reaction in which transesterification is carried out while generating fat crystals under a catalyst having transesterification ability. The direct transesterification method of the present invention may be a batch type or a continuous type.
前記ダイレクトエステル交換反応に使用する触媒は特に限定せず、エステル交換能を有していれば化学触媒、酵素触媒など何を使用しても良い。化学触媒の中でもカリウムナトリウム合金は低温での活性が高いことから好ましく、ナトリウムメチラートは経済性や扱い易さからより好ましい。化学触媒の使用量は特に限定されず、通常のエステル交換で使用される量で良いが、反応効率と経済性から反応油脂１００重量部に対して０．０１重量部〜１重量部が好ましい。酵素触媒は、エステル交換能を有するリパーゼであれば特に限定されず、位置特異性が全くないランダムエステル交換酵素でも、１，３位特異性を有するエステル交換酵素でも良い。酵素触媒の使用量はエステル交換反応が進行する量で良く、特に限定されないが、反応効率と経済性から反応油脂１００重量部に対して０．５重量部〜２０重量部が好ましい。 The catalyst used for the direct transesterification reaction is not particularly limited, and any catalyst such as a chemical catalyst or an enzyme catalyst may be used as long as it has transesterification ability. Among the chemical catalysts, potassium sodium alloy is preferable because of its high activity at low temperatures, and sodium methylate is more preferable because of economy and ease of handling. The amount of the chemical catalyst used is not particularly limited, and may be an amount used in ordinary transesterification, but is preferably 0.01 part by weight to 1 part by weight with respect to 100 parts by weight of the reaction fat and oil from the viewpoint of reaction efficiency and economy. The enzyme catalyst is not particularly limited as long as it is a lipase having transesterification ability, and may be a random transesterase having no positional specificity or a transesterase having 1,3-position specificity. The amount of the enzyme catalyst used may be an amount allowing the transesterification reaction to proceed, and is not particularly limited, but is preferably 0.5 to 20 parts by weight with respect to 100 parts by weight of the reaction fat and oil from the viewpoint of reaction efficiency and economy.
ダイレクトエステル交換反応の反応温度は、高融点グリセライドが結晶化する温度であれば特に限定されないが、反応開始時は効率良く反応を行なうために触媒活性が最も高くなる温度が好ましい。具体的にはナトリウムメチラートを使用する場合においては５０℃〜１２０℃が好ましい。また、酵素触媒の場合においては５０℃〜７０℃が好ましい。最終的な温度は、一般的な高融点グリセライドの結晶化効率の観点から１０℃〜４０℃が好ましく、最終的な温度をダイレクトエステル交換温度とする。 The reaction temperature of the direct transesterification reaction is not particularly limited as long as it is a temperature at which the high melting point glyceride is crystallized, but is preferably a temperature at which the catalytic activity is highest in order to perform the reaction efficiently at the start of the reaction. Specifically, when sodium methylate is used, it is preferably 50 ° C to 120 ° C. Moreover, in the case of an enzyme catalyst, 50 to 70 degreeC is preferable. The final temperature is preferably 10 ° C. to 40 ° C. from the viewpoint of the crystallization efficiency of a general high melting point glyceride, and the final temperature is the direct transesterification temperature.
ダイレクトエステル交換反応において、攪拌はあっても無くても良いが、油脂に流動性を与えるためには１０００ｒｐｍ以下の速度で攪拌を行うことが好ましい。分別効率を考慮すると、攪拌速度は６００ｒｐｍ以下で攪拌することがより好ましい。 In the direct transesterification reaction, stirring may or may not be performed, but it is preferable to perform stirring at a speed of 1000 rpm or less in order to impart fluidity to the fats and oils. Considering the separation efficiency, it is more preferable that the stirring speed is 600 rpm or less.
ダイレクトエステル交換反応の停止は、反応が停止しさえすれば方法は問わず、化学触媒であれば水やクエン酸水の添加などが挙げられる。ダイレクトエステル交換反応を停止するタイミングは、液状油脂の収率の観点から反応中の油脂組成中のＳＳＳ含量が３１重量％以下且つＳ２Ｕ含量が１４重量％以下になるまで反応した後が好ましい。 The direct transesterification reaction can be stopped by any method as long as the reaction is stopped, and if it is a chemical catalyst, water or citric acid water can be added. The timing for stopping the direct transesterification reaction is preferably after the reaction is carried out until the SSS content in the oil / fat composition during the reaction is 31% by weight or less and the S2U content is 14% by weight or less from the viewpoint of the yield of the liquid oil / fat.
本発明の固体脂の製造方法における分別の方法は、溶剤分別、乾式分別問わないが、溶剤分別は溶剤の使用により設備費やランニングコストがかかるため、溶剤を使用しない乾式分別が好ましい。もし、溶剤を使用する場合は、ヘキサン、アセトンなどを用いることができる。乾式分別の分別温度は、ろ別する液状油脂の液状性を充分にするためには０〜３０℃以下が好ましく、収率の観点も含めると０℃〜１０℃がより好ましい。固体脂中の２位にパルミチン酸を有するグリセライドの含有量を高めるためには、一旦前記乾式分別を行った後、分別温度を上昇させて、４０℃〜６０℃で再度分別することが好ましく、２位にパルミチン酸を有するグリセライドの含有量と収率を考慮すると４５℃〜５５℃がより好ましい。 The method for fractionation in the method for producing solid fat of the present invention is not limited to solvent fractionation and dry fractionation. However, since solvent fractionation requires equipment costs and running costs due to the use of a solvent, dry fractionation without using a solvent is preferred. If a solvent is used, hexane, acetone or the like can be used. The fractionation temperature for dry fractionation is preferably 0 to 30 ° C. or less in order to ensure the liquidity of the liquid oil to be filtered, and more preferably 0 to 10 ° C. in view of the yield. In order to increase the content of glyceride having palmitic acid at the 2-position in the solid fat, it is preferable to raise the fractionation temperature once after the dry fractionation, and fractionate again at 40 ° C to 60 ° C, Considering the content and yield of glyceride having palmitic acid at the 2-position, 45 ° C. to 55 ° C. is more preferable.
本発明の固体脂は、クリーム、マーガリン、ショートニング、チョコレートなどの加工油脂製品の原料やそのままマイクロカプセルの基材などに利用することが出来る。また、ＯＰＯ（２−パルミトイル−１，３−ジオレイルトリグリセライド）構造油脂の原料や、ＰＰＯ（１，２−ジパルミトイル−３−ジオレイルトリグリセライド）構造油脂の原料などに利用することも出来る。 The solid fat of the present invention can be used as a raw material for processed oil and fat products such as cream, margarine, shortening, and chocolate, or as a base material for microcapsules as it is. Further, it can also be used as a raw material for OPO (2-palmitoyl-1,3-dioleyl triglyceride) structure oil or a PPO (1,2-dipalmitoyl-3-dioleyl triglyceride) structure oil.
なお、本発明において前記各トリグリセライド含量を測定する方法は、以下の通りである。
＜液状油脂中の各トリグリセライド含量の測定＞
本発明の各トリグリセライド含量は、ＨＰＬＣを用いて、ＡＯＣＳ Ｏｆｆｉｃｉａｌ Ｍｅｔｈｏｄ Ｃｅ ５ｃ−９３に準拠して測定し、各ピークのリテンションタイムおよびエリア比から算出した。以下に、分析の条件を記す。
溶離液 ：アセトニトリル：アセトン（７０：３０、体積比）
流速 ：０．９ｍｌ／分
カラム ：ＯＤＳ
カラム温度：３６℃
検出器 ：示差屈折計
In the present invention, the method for measuring each triglyceride content is as follows.
<Measurement of each triglyceride content in liquid oil>
Each triglyceride content of the present invention was measured based on AOCS Official Method Ce 5c-93 using HPLC, and calculated from the retention time and area ratio of each peak. The analysis conditions are described below.
Eluent: Acetonitrile: Acetone (70:30, volume ratio)
Flow rate: 0.9 ml / min Column: ODS
Column temperature: 36 ° C
Detector: Differential refractometer
以下に実施例を示し、本発明をより具体的に説明するが、本発明はこれらの実施例に何ら限定されるものではない。なお、実施例において「部」や「％」は重量基準である。 EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples. In the examples, “parts” and “%” are based on weight.
＜液状油脂中の各トリグリセライド含量の測定＞
本発明の各トリグリセライド含量は、ＨＰＬＣを用いて、ＡＯＣＳ Ｃｅ５ｃ−９７に準拠して測定し、各ピークのリテンションタイムおよびエリア比から算出した。以下に、分析の条件を記す。
溶離液 ：アセトニトリル：アセトン（７０：３０、体積比）
流速 ：０．９ｍｌ／分
カラム ：ＯＤＳ
カラム温度：３６℃
検出器 ：示差屈折計
<Measurement of each triglyceride content in liquid oil>
Each triglyceride content of the present invention was measured based on AOCS Ce5c-97 using HPLC, and calculated from the retention time and area ratio of each peak. The analysis conditions are described below.
Eluent: Acetonitrile: Acetone (70:30, volume ratio)
Flow rate: 0.9 ml / min Column: ODS
Column temperature: 36 ° C
Detector: Differential refractometer
＜２位にパルミチン酸を有するグリセライド含量の測定＞
分析対象の油脂７．５ｇとエタノール２２．５ｇを混合しノボザイム４３５（ノボザイムジャパン社製）を１．２ｇ加えて３０℃で４時間反応させ、反応液を濃縮後、シリカゲルカラムクロマトグラフィー（型番：シリカゲル６０（０．０６３−０．２００ｍｍ）カラムクロマトグラフィー用、メルク社製）によりトリグリセリド、ジグリセリド、モノグリセリドの各成分に分離し、そのうちモノグリセリド成分を回収した。そのモノグリセリド０．０５ｇをイソオクタン５ｍｌに溶解し、０．２ｍｏｌ／Ｌナトリウムメチラート／メタノール溶液１ｍｌを加えて７０℃で１５分間反応させることによりメチルエステル化し、酢酸により反応液を中和した後に適量の水を加え、有機相をガスクロマトグラフ（型番：６８９０Ｎ、Ａｇｉｌｅｎｔ社製）によるリテンションタイム及びピークエリア面積により２位にパルミチン酸を有するグリセライド含有量を決定した。
<Measurement of glyceride content with palmitic acid at the 2-position>
After mixing 7.5g of fats and oils to be analyzed and 22.5g of ethanol, add 1.2g of Novozyme 435 (manufactured by Novozyme Japan) and react at 30 ° C for 4 hours. After concentrating the reaction solution, silica gel column chromatography (model number) : Separation into triglyceride, diglyceride and monoglyceride components by silica gel 60 (0.063-0.200 mm) for column chromatography, manufactured by Merck & Co., Ltd., and the monoglyceride component was recovered. Dissolve 0.05 g of the monoglyceride in 5 ml of isooctane, add 1 ml of 0.2 mol / L sodium methylate / methanol solution, react at 70 ° C. for 15 minutes, methyl esterify, and neutralize the reaction solution with acetic acid. The glyceride content having palmitic acid at the second position was determined based on the retention time and peak area area of the organic phase by gas chromatography (model number: 6890N, manufactured by Agilent).
（実施例１） 固体脂の作製
パームオレイン（ヨウ素価：５７）５０００重量部をセパラブルフラスコに入れ、１００ｒｐｍで攪拌しながら９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後降温し、３０℃でダイレクトエステル交換反応を８時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ２７重量％、１１．６重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を反応停止した。その後、加熱して全ての結晶を溶解し、７０℃の温水を５０００重量部加え、静置して油層と水層を分離し、水を抜いて分離する温水洗浄を行った。分離した水層のｐＨが８以下になるまで温水洗浄を繰り返した後、油層の油脂を９０℃に加熱し、真空脱水を行なった後、白土を２重量部加えて２０分間攪拌し、その後ろ過することで白土を除き、脱色を行なった。脱色後の温度を４０℃までは１℃／分（設定値）、４０℃から０．２℃／分（設定値）で降温し、１０℃に到達したらその温度を保持し、降温開始時から計２４時間になるまで晶析した。晶析後、フィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、固体脂全体中のＳＳＳ含量が５９重量％、ＰＰＰ含量が４５重量％、２位にパルミチン酸を有するグリセライド含量が７６重量％である固体脂を２２５０重量部（収率：４５％）得た。得られた固体脂について表１にまとめた。
(Example 1) Production of solid fat 5000 parts by weight of palm olein (iodine value: 57) was put into a separable flask, vacuum dehydrated at 90 ° C. with stirring at 100 rpm, and then 5 parts by weight of sodium methylate was added. The temperature was lowered after holding at 90 ° C. for 20 minutes, and the direct transesterification reaction was carried out at 30 ° C. for 8 hours. The SSS content and S2U content were 27% by weight and 11.6% by weight, respectively, in the total fats and oils during the reaction. After confirming this, 50 parts by weight of water was added as a reaction terminator to terminate the reaction. Thereafter, all crystals were dissolved by heating, 5000 parts by weight of 70 ° C. warm water was added, and the mixture was allowed to stand to separate the oil layer and the water layer, followed by hot water washing for removing water and separating it. After repeated washing with warm water until the pH of the separated aqueous layer is 8 or less, the oil in the oil layer is heated to 90 ° C., vacuum dehydration is performed, 2 parts by weight of white clay is added, and the mixture is stirred for 20 minutes, and then filtered. By doing so, the white soil was removed and decolorization was performed. The temperature after decolorization is 1 ° C / min (set value) up to 40 ° C, and the temperature is decreased from 40 ° C to 0.2 ° C / min (set value). When the temperature reaches 10 ° C, the temperature is maintained. Crystallization continued until a total of 24 hours. After crystallization, it is filtered using a filter press (pressurized up to 3 MPa), so that the SSS content in the whole solid fat is 59% by weight, the PPP content is 45% by weight, and the glyceride content having palmitic acid at the 2-position is 76%. As a result, 2250 parts by weight of solid fat (yield: 45%) was obtained. The obtained solid fat is summarized in Table 1.
（実施例２） 固体脂の作製
パームオレイン（ヨウ素価：５７）５０００重量部をセパラブルフラスコに入れ、１００ｒｐｍで攪拌しながら９０℃で真空脱水を行なった後ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後降温し、ダイレクトエステル交換反応を３０℃で８時間行った後、さらに２５℃で約２４時間該反応を行ってＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ３０重量％、９．４重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を停止した。その後は実施例１と同様にして、固体脂全体中のＳＳＳ含量が６４重量％、ＰＰＰ含量が４８重量％、２位にパルミチン酸を有するグリセライド含量が８２重量％である固体脂を２３００重量部（収率：４６％）得た。得られた固体脂について表１にまとめた。
(Example 2) Preparation of solid fat 5000 parts by weight of palm olein (iodine value: 57) was put in a separable flask, vacuum dehydrated at 90 ° C. with stirring at 100 rpm, and then 5 parts by weight of sodium methylate was added. After holding at 90 ° C. for 20 minutes, the temperature was lowered, and the direct transesterification reaction was performed at 30 ° C. for 8 hours, and then the reaction was further performed at 25 ° C. for about 24 hours. After confirming that it became 30 wt% and 9.4 wt%, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Example 1, 2300 parts by weight of solid fat having an SSS content of 64% by weight, a PPP content of 48% by weight, and a glyceride content having palmitic acid at the 2-position of 82% by weight in the whole solid fat. (Yield: 46%) was obtained. The obtained solid fat is summarized in Table 1.
（実施例３） 固体脂の作製
パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れ１００ｒｐｍで攪拌しながら９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後降温し、ダイレクトエステル交換反応を３０℃で８時間、２７．５℃で２時間、２５℃で１２時間、２２．５℃で約２４時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ２３重量％、１０．６重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を停止した。その後は実施例１と同様にして、固体脂全体中のＳＳＳ含量が５９重量％、ＰＰＰ含量が４５重量％、２位にパルミチン酸を有するグリセライド含量が７５重量％である固体脂を１９５０重量部（収率：３９％）得た。得られた固体脂について表１にまとめた。
(Example 3) Production of solid fat After 5000 parts by weight of palm olein (iodine value: 64) was put in a separable flask and stirred at 100 rpm under vacuum dehydration at 90 ° C, 5 parts by weight of sodium methylate was added, The temperature was lowered after holding at 90 ° C. for 20 minutes, and the direct transesterification reaction was carried out at 30 ° C. for 8 hours, 27.5 ° C. for 2 hours, 25 ° C. for 12 hours, and 22.5 ° C. for about 24 hours. After confirming that the contents were 23% by weight and 10.6% by weight, respectively, in the entire fat and oil during the reaction, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Example 1, 1950 parts by weight of solid fat having an SSS content of 59% by weight, a PPP content of 45% by weight, and a glyceride content having palmitic acid at the 2-position of 75% by weight in the whole solid fat (Yield: 39%) was obtained. The obtained solid fat is summarized in Table 1.
（実施例４） 固体脂の作製
パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れ、１００ｒｐｍで攪拌しながら９０℃で真空脱水を行なった後、ナトリウムメチラートを１０重量部加え、９０℃で２０分間保持した後降温し、ダイレクトエステル交換反応を３０℃で８時間、２７．５℃で２時間、２５℃で２時間、２２．５℃で５時間、１８℃で約１５時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ２９重量％、３．８重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を停止した。その後は実施例１と同様にして、固体脂全体中のＳＳＳ含量が６４重量％、ＰＰＰ含量が４９重量％、２位にパルミチン酸を有するグリセライド含量が８３重量％である固体脂を２２５０重量部（収率：４５％）得た。得られた固体脂について表１にまとめた。
(Example 4) Production of solid fat 5000 parts by weight of palm olein (iodine value: 64) was placed in a separable flask, vacuum dehydrated at 90 ° C while stirring at 100 rpm, and then 10 parts by weight of sodium methylate was added. The temperature was decreased after holding at 90 ° C. for 20 minutes, and the direct transesterification reaction was performed at 30 ° C. for 8 hours, 27.5 ° C. for 2 hours, 25 ° C. for 2 hours, 22.5 ° C. for 5 hours, and 18 ° C. for about 15 hours. The reaction was stopped by adding 50 parts by weight of water as a reaction terminator after confirming that the SSS content and S2U content were 29% by weight and 3.8% by weight, respectively, in the total fat and oil during the reaction. Thereafter, in the same manner as in Example 1, 2250 parts by weight of solid fat having an SSS content of 64% by weight, a PPP content of 49% by weight, and a glyceride content having palmitic acid at the 2-position of 83% by weight in the whole solid fat. (Yield: 45%) was obtained. The obtained solid fat is summarized in Table 1.
（実施例５） 固体脂の作製
パームオレイン（ヨウ素価：５７）５０００重量部をセパラブルフラスコに入れ、１００ｒｐｍで攪拌しながら９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後降温し、３０℃でダイレクトエステル交換反応を約８時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ２７重量％、１１．６重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を反応停止した。その後、加熱して全て結晶を溶解し、７０℃の温水を加え、静置して油層と水層を分離し、水を抜いて分離する温水洗浄を行った。分離した水層のｐＨが８以下になるまで温水洗浄を繰り返した後、油層の油脂を９０℃に加熱し、真空脱水を行ない、白土を２重量部加えて２０分間攪拌後、ろ過することで白土を除いて脱色を行なった。脱色後の温度を４０℃までは１℃／分（設定値）、４０℃から０．２℃／分（設定値）で下げ、３０℃に到達したらその温度を保持し、降温開始時から計２４時間になるまで晶析した。晶析後、フィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、固体脂全体中のＳＳＳ含量が６８重量％、ＰＰＰ含量が５２重量％、２位にパルミチン酸を有するグリセライド含量が７０重量％である固体脂を２０５０重量部（収率：４１％）得た。得られた固体脂について表１にまとめた。
(Example 5) Production of solid fat 5000 parts by weight of palm olein (iodine number: 57) was put into a separable flask, vacuum dehydrated at 90 ° C. with stirring at 100 rpm, and then 5 parts by weight of sodium methylate was added. , Kept at 90 ° C. for 20 minutes, then cooled down, and subjected to direct transesterification at 30 ° C. for about 8 hours. The SSS content and S2U content were 27% by weight and 11.6% by weight, respectively, in the total fats and oils during the reaction. After confirming this, 50 parts by weight of water was added as a reaction terminator to terminate the reaction. Thereafter, all the crystals were dissolved by heating, warm water at 70 ° C. was added, and the mixture was allowed to stand to separate the oil layer and the water layer, followed by warm water washing for removing water and separating it. After repeated washing with warm water until the pH of the separated aqueous layer is 8 or less, the oil in the oil layer is heated to 90 ° C., vacuum dewatered, added 2 parts by weight of white clay, stirred for 20 minutes, and then filtered. Decolorization was performed except for the white clay. The temperature after decolorization is reduced to 1 ° C / min (set value) up to 40 ° C, and decreased from 40 ° C to 0.2 ° C / min (set value). When the temperature reaches 30 ° C, the temperature is maintained and measured from the start of temperature decrease. Crystallization continued until 24 hours. After crystallization, it is filtered using a filter press (pressurized up to 3 MPa), so that the SSS content in the whole solid fat is 68% by weight, the PPP content is 52% by weight, and the glyceride content having palmitic acid at the 2-position is 70%. As a result, 2050 parts by weight (yield: 41%) of a solid fat having a weight% was obtained. The obtained solid fat is summarized in Table 1.
（実施例６）
パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れ、１００ｒｐｍで攪拌しながら９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後降温し、３０℃でダイレクトエステル交換反応を約８時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ１８重量％、１３．５重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を反応停止した。その後、加熱して全て結晶を溶解し、７０℃の温水を加え、静置して油層と水層を分離し、水を抜いて分離する温水洗浄を行った。分離した水層のｐＨが８以下になるまで温水洗浄を繰り返した後、油層の油脂を９０℃に加熱し、真空脱水を行ない、白土を２重量部加えて２０分間攪拌後、ろ過することで白土を除いて脱色を行なった。脱色後の温度を４０℃までは１℃／分（設定値）、４０℃から０．２℃／分（設定値）で下げ、３０℃に到達したらその温度を保持し、降温開始時から計２４時間になるまで晶析した。晶析後、フィルタープレス（３ＭＰａまで加圧）を用いて軟質部をろ別後、圧力を開放した状態で温度を４５℃まで昇温し再び３ＭＰａまで加圧を行なった後、再び温度を６０℃まで上昇させた後、再度３ＭＰａまで加圧して、固体脂全体中のＳＳＳ含量が９５重量％、ＰＰＰ含量が７８重量％、２位にパルミチン酸を有するグリセライド含量が９１重量％である固体脂を４００重量部（収率：８％）得た。得られた固体脂について表１にまとめた。
(Example 6)
After adding 5000 parts by weight of palm olein (iodine number: 64) to a separable flask and performing vacuum dehydration at 90 ° C. with stirring at 100 rpm, 5 parts by weight of sodium methylate was added and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours. After confirming that the SSS content and S2U content were 18% by weight and 13.5% by weight, respectively, in the entire fat and oil during the reaction, The reaction was stopped by adding 50 parts by weight of water. Thereafter, all the crystals were dissolved by heating, warm water at 70 ° C. was added, and the mixture was allowed to stand to separate the oil layer and the water layer, followed by warm water washing for removing water and separating it. After repeated washing with warm water until the pH of the separated aqueous layer is 8 or less, the oil in the oil layer is heated to 90 ° C., vacuum dewatered, added 2 parts by weight of white clay, stirred for 20 minutes, and then filtered. Decolorization was performed except for the white clay. The temperature after decolorization is reduced to 1 ° C / min (set value) up to 40 ° C, and decreased from 40 ° C to 0.2 ° C / min (set value). When the temperature reaches 30 ° C, the temperature is maintained and measured from the start of temperature decrease. Crystallization continued until 24 hours. After crystallization, the soft part was filtered off using a filter press (pressurized to 3 MPa), the temperature was raised to 45 ° C. with the pressure released, the pressure was increased to 3 MPa, and then the temperature was increased to 60 again. The solid fat having an SSS content of 95% by weight, a PPP content of 78% by weight, and a glyceride content having palmitic acid at the second position of 91% by weight after being pressurized to 3 ° C. 400 parts by weight (yield: 8%) was obtained. The obtained solid fat is summarized in Table 1.
（実施例７）
パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れ、１００ｒｐｍで攪拌しながら９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後降温し、３０℃でダイレクトエステル交換反応を約８時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ１８重量％、１３．５重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を反応停止した。その後、加熱して全て結晶を溶解し、７０℃の温水を加え、静置して油層と水層を分離し、水を抜いて分離する温水洗浄を行った。分離した水層のｐＨが８以下になるまで温水洗浄を繰り返した後、油層の油脂を９０℃に加熱し、真空脱水を行ない、白土を２重量部加えて２０分間攪拌後、ろ過することで白土を除いて脱色を行なった。脱色後の温度を４０℃までは１℃／分（設定値）、４０℃から０．２℃／分（設定値）で下げ、２０℃に到達したらその温度を保持し、降温開始時から計２４時間になるまで晶析した。晶析後、フィルタープレス（３ＭＰａまで加圧）を用いて軟質部をろ別後、圧力を開放した状態で温度を４５℃まで昇温し、再び３ＭＰａまで加圧を行なった後、再び温度を５５℃まで上昇させた後、再度３ＭＰａまで加圧して、固体脂全体中のＳＳＳ含量が８０重量％、ＰＰＰ含量が６１重量％、２位にパルミチン酸を有するグリセライド含量が８２重量％である固体脂を１０００重量部（収率：２０％）得た。得られた固体脂について表１にまとめた。
(Example 7)
After adding 5000 parts by weight of palm olein (iodine number: 64) to a separable flask and performing vacuum dehydration at 90 ° C. with stirring at 100 rpm, 5 parts by weight of sodium methylate was added and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours. After confirming that the SSS content and S2U content were 18% by weight and 13.5% by weight, respectively, in the entire fat and oil during the reaction, The reaction was stopped by adding 50 parts by weight of water. Thereafter, all the crystals were dissolved by heating, warm water at 70 ° C. was added, and the mixture was allowed to stand to separate the oil layer and the water layer, followed by warm water washing for removing water and separating it. After repeated washing with warm water until the pH of the separated aqueous layer is 8 or less, the oil in the oil layer is heated to 90 ° C., vacuum dewatered, added 2 parts by weight of white clay, stirred for 20 minutes, and then filtered. Decolorization was performed except for the white clay. The temperature after decolorization is reduced to 1 ° C / min (set value) up to 40 ° C, and decreased from 40 ° C to 0.2 ° C / min (set value). When 20 ° C is reached, the temperature is maintained and measured from the start of temperature decrease. Crystallization continued until 24 hours. After crystallization, after filtering the soft part using a filter press (pressurization up to 3 MPa), the temperature is raised to 45 ° C. with the pressure released, and after pressurizing up to 3 MPa again, the temperature is increased again. After raising the temperature to 55 ° C., pressurizing again to 3 MPa, the solid fat has an SSS content of 80% by weight, a PPP content of 61% by weight, and a glyceride content having palmitic acid at the 2-position of 82% by weight. 1000 parts by weight (yield: 20%) of fat was obtained. The obtained solid fat is summarized in Table 1.
（実施例８）
パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れ、１００ｒｐｍで攪拌しながら９０℃で真空脱水を行なった後ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後降温し、３０℃でダイレクトエステル交換反応を約８時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ１８重量％、１３．５重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を反応停止した。その後、加熱して全て結晶を溶解し、７０℃の温水を加え、静置して油層と水層を分離し、水を抜いて分離する温水洗浄を行った。分離した水層のｐＨが８以下になるまで温水洗浄を繰り返した後、油層の油脂を９０℃に加熱し、真空脱水を行ない、白土を２重量部加えて２０分間攪拌後、ろ過することで白土を除いて脱色を行なった。脱色後の温度を４０℃までは１℃／分（設定値）、４０℃から０．２℃／分（設定値）で下げ、２０℃に到達したらその温度を保持し、降温開始時から計２４時間になるまで晶析した。晶析後、フィルタープレス（３ＭＰａまで加圧）を用いて軟質部をろ別後、圧力を開放した状態で温度を４５℃まで昇温し、再び３ＭＰａまで加圧を行なった後、再び温度を５０℃まで上昇させた後、再度３ＭＰａまで加圧して、固体脂全体中のＳＳＳ含量が７３重量％、ＰＰＰ含量が５６重量％、２位にパルミチン酸を有するグリセライド含量が８４重量％である固体脂を１１５０重量部（収率：２３％）得た。得られた固体脂について表１にまとめた。
(Example 8)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask, vacuum dehydrated at 90 ° C. with stirring at 100 rpm, 5 parts by weight of sodium methylate was added, and the mixture was kept at 90 ° C. for 20 minutes and then cooled Then, the direct transesterification reaction was carried out at 30 ° C. for about 8 hours. After confirming that the SSS content and the S2U content were 18% by weight and 13.5% by weight, respectively, the reaction oil was water as a reaction terminator. Was added to stop the reaction. Thereafter, all the crystals were dissolved by heating, warm water at 70 ° C. was added, and the mixture was allowed to stand to separate the oil layer and the water layer, followed by warm water washing for removing water and separating it. After repeated washing with warm water until the pH of the separated aqueous layer is 8 or less, the oil in the oil layer is heated to 90 ° C., vacuum dewatered, added 2 parts by weight of white clay, stirred for 20 minutes, and then filtered. Decolorization was performed except for the white clay. The temperature after decolorization is reduced to 1 ° C / min (set value) up to 40 ° C, and decreased from 40 ° C to 0.2 ° C / min (set value). When 20 ° C is reached, the temperature is maintained and measured from the start of temperature decrease. Crystallization continued until 24 hours. After crystallization, after filtering the soft part using a filter press (pressurization up to 3 MPa), the temperature is raised to 45 ° C. with the pressure released, and after pressurizing up to 3 MPa again, the temperature is increased again. After raising the temperature to 50 ° C. and pressurizing again to 3 MPa, the solid fat has an SSS content of 73 wt%, a PPP content of 56 wt%, and a glyceride content having palmitic acid at the 2nd position is 84 wt% 1150 parts by weight of fat (yield: 23%) was obtained. The obtained solid fat is summarized in Table 1.
（実施例９）
パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れ、１００ｒｐｍで攪拌しながら９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後降温し、３０℃でダイレクトエステル交換反応を約８時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ２７重量％、１１．６重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を反応停止した。その後、加熱して全て結晶を溶解し、７０℃の温水を加え、静置して油層と水層を分離し、水を抜いて分離する温水洗浄を行った。分離した水層のｐＨが８以下になるまで温水洗浄を繰り返した後、油層の油脂を９０℃に加熱し、真空脱水を行ない、白土を２重量部加えて２０分間攪拌後、ろ過することで白土を除いて脱色を行なった。脱色後の温度を４０℃までは１℃／分（設定値）、４０℃から０．２℃／分（設定値）で下げ、２０℃に到達したらその温度を保持し、降温開始時から計２４時間になるまで晶析した。晶析後、フィルタープレス（３ＭＰａまで加圧）を用いて軟質部をろ別後、圧力を開放した状態で温度を４５℃まで昇温し、再び３ＭＰａまで加圧を行なった後、再び温度を５５℃まで上昇させた後、再度３ＭＰａまで加圧して、固体脂全体中のＳＳＳ含量が８３重量％、ＰＰＰ含量が６５重量％、２位にパルミチン酸を有するグリセライド含量が８３重量％である固体脂を１５００重量部（収率：３２％）得た。得られた固体脂について表１にまとめた。
Example 9
After adding 5000 parts by weight of palm olein (iodine number: 64) to a separable flask and performing vacuum dehydration at 90 ° C. with stirring at 100 rpm, 5 parts by weight of sodium methylate was added and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification reaction was performed at 30 ° C. for about 8 hours. After confirming that the SSS content and the S2U content were 27% by weight and 11.6% by weight, respectively, as the reaction terminator. The reaction was stopped by adding 50 parts by weight of water. Thereafter, all the crystals were dissolved by heating, warm water at 70 ° C. was added, and the mixture was allowed to stand to separate the oil layer and the water layer, followed by warm water washing for removing water and separating it. After repeated washing with warm water until the pH of the separated aqueous layer is 8 or less, the oil in the oil layer is heated to 90 ° C., vacuum dewatered, added 2 parts by weight of white clay, stirred for 20 minutes, and then filtered. Decolorization was performed except for the white clay. The temperature after decolorization is reduced to 1 ° C / min (set value) up to 40 ° C, and decreased from 40 ° C to 0.2 ° C / min (set value). When 20 ° C is reached, the temperature is maintained and measured from the start of temperature decrease. Crystallization continued until 24 hours. After crystallization, after filtering the soft part using a filter press (pressurization up to 3 MPa), the temperature is raised to 45 ° C. with the pressure released, and after pressurizing up to 3 MPa again, the temperature is increased again. After raising the temperature to 55 ° C., pressurizing again to 3 MPa, the solid fat has an SSS content of 83% by weight, a PPP content of 65% by weight, and a glyceride content having palmitic acid at the 2-position of 83% by weight. 1500 parts by weight of fat (yield: 32%) was obtained. The obtained solid fat is summarized in Table 1.
（比較例１） 固体脂の作製
パームオレイン（ヨウ素価：５７）５０００重量部をセパラブルフラスコに入れ、１００ｒｐｍで攪拌しながら９０℃で真空脱水を行なった後、ナトリウムメチラートを１０重量部加え、９０℃で２０分間保持した後降温し、ダイレクトエステル交換反応を３０℃で８時間、２７．５℃で２時間、２５℃で２時間、２２．５℃で５時間、１８℃で約１５時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ３７重量％、３．４重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を停止した。その後は実施例１と同様にして、固体脂全体中のＳＳＳ含量が４４重量％、ＰＰＰ含量が固体脂全体中３３重量％、２位にパルミチン酸を有するグリセライド含量が３６重量％である固体脂を４１５０重量部（収率：８２％）得た。得られた固体脂について表１にまとめた。
(Comparative example 1) Preparation of solid fat 5000 parts by weight of palm olein (iodine value: 57) was put into a separable flask, vacuum dehydrated at 90 ° C. with stirring at 100 rpm, and then 10 parts by weight of sodium methylate was added. The temperature was decreased after holding at 90 ° C. for 20 minutes, and the direct transesterification reaction was performed at 30 ° C. for 8 hours, 27.5 ° C. for 2 hours, 25 ° C. for 2 hours, 22.5 ° C. for 5 hours, and 18 ° C. for about 15 hours. After confirming that the SSS content and S2U content were 37% by weight and 3.4% by weight, respectively, in the total fat and oil during the reaction, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Example 1, the solid fat had an SSS content of 44% by weight in the whole solid fat, a PPP content of 33% by weight in the whole solid fat, and a glyceride content having palmitic acid at the 2-position of 36% by weight. 4150 parts by weight (yield: 82%) was obtained. The obtained solid fat is summarized in Table 1.
（比較例２） 固体脂の作製
パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れ、１００ｒｐｍで攪拌しながら９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後降温し、ダイレクトエステル交換反応を３６℃で約８時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ１３重量％、１６．５重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を停止した。その後は実施例１と同様にして、固体脂全体中のＳＳＳ含量が３６重量％、ＰＰＰ含量が２７重量％、２位にパルミチン酸を有するグリセライド含量が４７重量％である固体脂を１８００重量部（収率：３５％）得た。得られた固体脂について表１にまとめた。
(Comparative example 2) Preparation of solid fat 5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask, vacuum dehydrated at 90 ° C while stirring at 100 rpm, and then 5 parts by weight of sodium methylate was added. The temperature was lowered after holding at 90 ° C. for 20 minutes, and the direct transesterification reaction was carried out at 36 ° C. for about 8 hours. The SSS content and S2U content were 13% by weight and 16.5% by weight, respectively, in the total fats and oils during the reaction. After confirming this, 50 parts by weight of water was added as a reaction stopper to stop the reaction. Thereafter, in the same manner as in Example 1, 1800 parts by weight of solid fat having an SSS content of 36% by weight, a PPP content of 27% by weight and a glyceride content having palmitic acid at the 2-position of 47% by weight in the whole solid fat (Yield: 35%) was obtained. The obtained solid fat is summarized in Table 1.
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