JPS62267293A - Method for purifying sucrose fatty acid ester - Google Patents
Method for purifying sucrose fatty acid esterInfo
- Publication number
- JPS62267293A JPS62267293A JP11207586A JP11207586A JPS62267293A JP S62267293 A JPS62267293 A JP S62267293A JP 11207586 A JP11207586 A JP 11207586A JP 11207586 A JP11207586 A JP 11207586A JP S62267293 A JPS62267293 A JP S62267293A
- Authority
- JP
- Japan
- Prior art keywords
- silica gel
- acid ester
- ester
- acetic acid
- isobutyric acid
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 14
- 229930006000 Sucrose Natural products 0.000 title abstract description 11
- 239000005720 sucrose Substances 0.000 title abstract description 11
- -1 sucrose fatty acid ester Chemical class 0.000 title description 8
- 235000014113 dietary fatty acids Nutrition 0.000 title description 7
- 239000000194 fatty acid Substances 0.000 title description 7
- 229930195729 fatty acid Natural products 0.000 title description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000741 silica gel Substances 0.000 claims abstract description 14
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 10
- UVGUPMLLGBCFEJ-SWTLDUCYSA-N sucrose acetate isobutyrate Chemical compound CC(C)C(=O)O[C@H]1[C@H](OC(=O)C(C)C)[C@@H](COC(=O)C(C)C)O[C@@]1(COC(C)=O)O[C@@H]1[C@H](OC(=O)C(C)C)[C@@H](OC(=O)C(C)C)[C@H](OC(=O)C(C)C)[C@@H](COC(C)=O)O1 UVGUPMLLGBCFEJ-SWTLDUCYSA-N 0.000 claims description 14
- 239000001797 sucrose acetate isobutyrate Substances 0.000 claims description 14
- 235000010983 sucrose acetate isobutyrate Nutrition 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 12
- QXNIBPDSSDVBQP-UHFFFAOYSA-N acetic acid;2-methylpropanoic acid Chemical compound CC(O)=O.CC(C)C(O)=O QXNIBPDSSDVBQP-UHFFFAOYSA-N 0.000 abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 11
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 abstract description 8
- 239000002537 cosmetic Substances 0.000 abstract description 5
- 235000013373 food additive Nutrition 0.000 abstract description 2
- 239000002778 food additive Substances 0.000 abstract description 2
- 239000002304 perfume Substances 0.000 abstract description 2
- 239000003208 petroleum Substances 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000019645 odor Nutrition 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 235000013305 food Nutrition 0.000 description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000011325 microbead Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Description
【発明の詳細な説明】
（ａｌ産業上の利用分野
本発明はシミ１１ｇ酢酸イソ酪酸エステル中の有臭成分
を除去し精製することに関する。DETAILED DESCRIPTION OF THE INVENTION (Al Industrial Field of Application) The present invention relates to the purification of stain 11g acetic acid isobutyric acid ester by removing its odoriferous components.
（ｂｌ従来の技術
従来、シ＝３Ｉａｉ脂肪酸エステルは一般的にはショ糖
と脂肪酸エステルをジメチルホルムアミド中でエステル
交換さ・［副生ずるメタノールを留去してつくるＳｈｅ
ｌ ｌ法あるいはショ糖をプロピレングリコールまた
は水に溶解し、脂肪酸石ケンの存在下で脂肪酸エステル
を微細粒子状に分散させ透明な乳化状態で反応させて製
造するＮｅｂｒａｓｋａ ５ｎｅｌｌ法により製造さ
れている。(BL Conventional Technology) Conventionally, She-3Iai fatty acid esters are generally produced by transesterifying sucrose and fatty acid esters in dimethylformamide.
It is produced by the 11 method or the Nebraska 5nell method, in which sucrose is dissolved in propylene glycol or water, and fatty acid esters are dispersed into fine particles in the presence of fatty acid soap and reacted in a transparent emulsified state.
各種のショ糖脂肪酸エステルのうちショ糖酢酸イソ酪酸
エステルは微黄色透明の非常に粘稠な液体であり、接着
性、フィルム特性、熱安定性、電気特性、紫外線安定性
に優れ“でいるなどの特性を生かして塗料、インキ、プ
ラスチソク工業に広く利用されている。Among various sucrose fatty acid esters, sucrose acetate isobutyrate is a pale yellow transparent and extremely viscous liquid that has excellent adhesive properties, film properties, thermal stability, electrical properties, and ultraviolet stability. Due to its characteristics, it is widely used in the paint, ink, and plastic industries.
また食品添加物として許可されており、食品工業、香料
工業、化粧品工業においても使用されている。食品工業
では清涼飲料水業界において比重調整剤として、また化
粧品業界では口紅、アイシャドー、アイライン、マスカ
ラなどの処方に組み込まれている。It is also permitted as a food additive and is used in the food, fragrance, and cosmetic industries. In the food industry, it is used as a specific gravity adjuster in the soft drink industry, and in the cosmetics industry, it is incorporated into formulations of lipstick, eye shadow, eyeliner, mascara, etc.
（Ｃ１発明が解決しようとする問題点
しかしながらシーＪ糖酢酸イソ酪酸エステルは、長期保
存下では不友定であり、保存中に酢酸およびイソ酪酸の
分解がおこり酢酸臭ならびにイソ酪酸臭などのもどり臭
がみられる。このことから従来の製品は食品工業、化粧
品工業への使用において必ずしも満足すべきものとはい
えなかった。(C1 Problem to be solved by the invention However, CJ sugar acetate isobutyric acid ester is unstable under long-term storage, and acetic acid and isobutyric acid decompose during storage, resulting in the return of acetic acid odor and isobutyric acid odor. Odor is observed.For this reason, conventional products are not necessarily satisfactory for use in the food industry and cosmetics industry.
このようなもどり臭を有効に防止する方法はこれまで知
られていない。Until now, no method has been known to effectively prevent such lingering odor.
本発明の目的は長期保存してももどり臭の発生がなく、
またもどり臭がいったん発生してもこれを除くことがで
きるショ糖酢酸イソ酪酸エステルの精製法を提供するこ
とにある。The purpose of the present invention is to prevent the occurrence of odors even after long-term storage.
Another object of the present invention is to provide a method for purifying sucrose acetate isobutyric acid ester, which can remove the residual odor even if it occurs once.
ｉｄ１問題点を解決するための手段
本発明者らは、上記の目的を達成すべく、鋭意研究した
結果、ショ糖酢酸イソ酪酸エステルをシリカゲルと接触
させることにより有臭酸が選択的にシリカゲルに吸着さ
れさらにショ糖酢酸イソ酪酸エステルは吸着されにくい
ことを見出し本発明を完成した。Means for solving the id1 problem In order to achieve the above object, the present inventors conducted extensive research and found that by bringing sucrose acetate isobutyrate into contact with silica gel, hydrobromic acid was selectively converted into silica gel. They found that sucrose acetate isobutyrate is difficult to adsorb, and completed the present invention.
すなわち本発明はショ糖酢酸イソ酪酸エステルに溶剤を
加えこれらをシリカゲルと接触させることを特徴とする
ショ糖酢酸イソ酪酸エステルの精製法である。That is, the present invention is a method for purifying sucrose acetate isobutyrate, which is characterized by adding a solvent to sucrose acetate isobutyrate and bringing the mixture into contact with silica gel.
本発明で使用するシリカゲルの粒子の形状は１８０〜５
００μｍの球状のものがこのましい。市販のものとして
はマイクロビーズ４Ｂ（富士デヴイソン（株）製）、マ
イクロスフエヤーゲル（旭硝子（株）製）などのソリカ
ノノ゛ルを用いることができる。これらはそのまま又は
カラムに充填して用いる。The shape of the silica gel particles used in the present invention is 180-5
A spherical one with a diameter of 00 μm is preferable. Commercially available solica nanosols such as Microbeads 4B (manufactured by Fuji Davison Co., Ltd.) and Microsphere Gel (manufactured by Asahi Glass Co., Ltd.) can be used. These are used as they are or packed in a column.
本発明で使用する溶剤とし′Ｃ番よ石油エーテル、ジエ
チルエーテル、ヘキ→ノ°ンなどの炭化水素系溶剤およ
びメタノール、エタノールなどの低級アルコールとこれ
らの混合物が挙げられる。これらの溶剤の使用量はシミ
１糊酢酸イソ酪酸エステルに対して１−１０倍量が好ま
しい。カラムに充填した場合の通液速度はＳＶ（空間速
度）＝０．１〜５が望ましく通液温度には特に制限はな
いが溶剤の沸点以下であることが必要である。Examples of the solvent used in the present invention include hydrocarbon solvents such as petroleum ether, diethyl ether and hexane, lower alcohols such as methanol and ethanol, and mixtures thereof. The amount of these solvents to be used is preferably 1 to 10 times the amount of acetic acid isobutyrate used in stain 1 paste. When the column is packed, the liquid passing rate is desirably SV (space velocity) = 0.1 to 5, and the liquid passing temperature is not particularly limited, but it is necessary to be below the boiling point of the solvent.
本発明の精製法は製造Ｉｌ′Ｉ後のショ糖酢酸イソ酪酸
エステルに対し゛（４）また製造後保存中にもどり臭を
発生したぜのに火１しても通用することができる。The purification method of the present invention can also be applied to sucrose acetate isobutyrate after production (4), and also to sucrose acetate isobutyric acid ester produced after production and after production, which has developed a lingering odor during storage.
ｔｅｌ実施例
実施例１
製造直後のシミ１糊酢酸イソ酪酸エステル６００ｇを２
．Ｏｌのヘキサンに溶解する。シリカゲル（マイクロス
フエヤーゲル・旭硝子（株）製）１４をガラス製カラム
に充填し、前記ショ糖酢酸イソ酪酸エステルのヘキサン
溶液を５Ｖ＝２．０で通液する。カラムの下口部より得
られた流出液を集めヘキサン溶液を留去しショ糖酢酸イ
ソ酪酸エステル精製物４９０ｇを得た。全工程を通しカ
ラム液温は１９℃であった。tel Examples Example 1 Immediately after production, stain 1 600g of glue acetate isobutyrate 2
．． Dissolve OL in hexane. A glass column is filled with silica gel (Microsphere Gel, manufactured by Asahi Glass Co., Ltd.) 14, and the hexane solution of sucrose acetate isobutyrate is passed therethrough at 5V=2.0. The effluent obtained from the lower part of the column was collected and the hexane solution was distilled off to obtain 490 g of purified sucrose acetate isobutyrate. The column liquid temperature was 19°C throughout the entire process.
製造直後の未処理の試料およびシリカゲル処理した試料
を保存して、もどり臭の発生を比較したところ第１表の
結果を得た。An untreated sample immediately after production and a sample treated with silica gel were stored, and the occurrence of lingering odor was compared, and the results shown in Table 1 were obtained.
第１表
５一
実施例２
製造後保存によりもどり臭が発生したシー１糖酢酸イソ
酪酸エステル３ （１０ｇを１．５ｆｆのジエチルエー
テルに溶解する。シリカゲルＣマイクロビーズ富士デヴ
イソン（株）製）５６０ｍｌをガラス製カラムに充填し
、前記ショ糖酢酸イソ酪酸エステルのジエチルエーテル
溶液を５Ｖ＝１．０で通液しシーｉ糖酢酸イソ酪酸エス
テルの精製物２３０ｇを得た。以上の全工程を１ｆｆｌ
じカラム液温は１５℃であった。Table 1 5-Example 2 Sea monosaccharide acetate isobutyric acid ester 3, which had a lingering odor due to storage after production (dissolve 10 g in 1.5 ff of diethyl ether, Silica Gel C Microbeads manufactured by Fuji Davison Co., Ltd.) 560 ml was packed in a glass column, and the diethyl ether solution of the sucrose acetate isobutyrate was passed therethrough at 5V=1.0 to obtain 230 g of purified sucrose acetate isobutyrate. The entire process above is 1ffl
The column liquid temperature was 15°C.
未処理品がもどり臭をかなり有するのに対し処理品は無
臭であった。While the untreated product had a considerable residual odor, the treated product was odorless.
実施例３
実施例２と同じもどり臭が発生したショ糖酢酸イソ酪酸
エステル３００ｇを１．Ｏｌのへキサンに溶解する。ガ
ラス製容器にシリカゲル（マイクロビーズ 富士デヴイ
ソン（株）製）３００ｇをはかりとり、前記シー１糖酢
酸イソ酪酸エステルのヘキサン溶液を加え室温で５時間
攪拌した後、濾紙を用いて濾過を行ったところシ・を糖
酢酸イソ酪酸エーロ＝
ステルの精製物２０５ｇを得た。Example 3 300 g of sucrose acetate isobutyric acid ester, which had the same returning odor as in Example 2, was mixed with 1. Dissolve OL in hexane. Weighed 300 g of silica gel (Microbeads manufactured by Fuji Davison Co., Ltd.) into a glass container, added the hexane solution of the above sea monosaccharide acetate isobutyrate, stirred at room temperature for 5 hours, and then filtered using filter paper. 205 g of purified sugar acetic acid isobutyric acid aeroester was obtained.
未処理品がもどり臭をかなり有するのに対し処理品は無
臭であった。While the untreated product had a considerable residual odor, the treated product was odorless.
（ｆ１発明の効果
本発明のシリカゲル処理を製造直後のショ糖酢酸イソ酪
酸エステルに施すと、これを保存してももどり臭の発生
がない。(f1 Effects of the Invention When the silica gel treatment of the present invention is applied to sucrose acetate isobutyrate immediately after production, no lingering odor occurs even when the product is stored.
また保存によりもどり臭がいったん生じたショ糖酢酸イ
ソ酪酸エステルに本発明の処理を行うと、もどり臭を除
くことができる。In addition, if sucrose acetate isobutyrate, which has developed a lingering odor due to storage, is treated according to the present invention, the lingering odor can be removed.
なお本発明の方法によれば、有臭成分のみならず着色成
分をも除去することができ、いっそう淡色な製品が得ら
れる。In addition, according to the method of the present invention, not only odorous components but also colored components can be removed, and a product with a lighter color can be obtained.
従って本発明による製品は食品工業、香料工業、化粧品
工業などへの使用において、これまでの製品に比べすぐ
れた性状を備えている。Therefore, the product according to the present invention has superior properties compared to conventional products when used in the food industry, perfume industry, cosmetics industry, etc.
特許出願人 日清製油株式会社
手続補正書（自発）
１、事件の表示
昭和６１年特許願第１１２０７５号
２、発明の名称
ショ糖脂肪酸エステルの精製法
３、補正をする者
事件との関係 特許出願人
住 所 東京都中央区新川−丁目２３番１号本件に
関する連絡ｔｅｌ： ’Ｆ記にお願いします。Patent applicant Nisshin Oil Co., Ltd. Procedural amendment (voluntary) 1. Indication of the case Patent Application No. 112075 of 1985 2. Name of the invention Method for refining sucrose fatty acid ester 3. Person making the amendment Relationship with the case Patent Applicant's address: 23-1 Shinkawa-chome, Chuo-ku, Tokyo Tel: 'F'
郵便番号 ２２１
４、補正の対象
明細書の発明の詳細な説明の欄
５、補正の内容
（１１明細書第１頁下から５行ｒｓｈｅｌｌ法」をｒｓ
ｎｅｌｌ法」と訂正する。Postal code 221 4, Detailed explanation of the invention column 5 of the specification to be amended, contents of the amendment (11 RSELL method in the 5th line from the bottom of page 1 of the specification)
nell method”.
（２）同第３頁９〜ＩＯ行「有臭酸が選択的に」を「有
臭成分が選択的に」と訂正する。(2) On page 3, lines 9 to IO, "bromic acid selectively" is corrected to "selectively odorous component".
＋３１ 同第４頁５〜６行「ジエチルエーテル、ヘキ
サンなどの炭化水素系溶剤およびメタノール、エタノー
ルなどの」を「ヘキサンなどの炭化水素系ｍ 剤、ジエ
チルエーテル、およびメタノール、エタノールなどの」
と訂正する。+31 Same page 4, lines 5-6, "Hydrocarbon solvents such as diethyl ether and hexane, and methanol, ethanol, etc." was changed to "Hydrocarbon solvents such as hexane, diethyl ether, and methanol, ethanol, etc."
I am corrected.
（４）同第４頁１５行「発生したぜのに対しても」を「
発生したものに対しても」と訂正する。(4) On page 4, line 15 of the same page, change “Even for what happened” to “
Even for things that have occurred,” he corrected.
Claims (1)
をシリカゲルと接触させることを特徴とするショ糖酢酸
イソ酪酸エステルの精製法。(1) A method for purifying sucrose acetate isobutyrate, which comprises adding a solvent to sucrose acetate isobutyrate and bringing the mixture into contact with silica gel.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11207586A JPS62267293A (en) | 1986-05-15 | 1986-05-15 | Method for purifying sucrose fatty acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11207586A JPS62267293A (en) | 1986-05-15 | 1986-05-15 | Method for purifying sucrose fatty acid ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62267293A true JPS62267293A (en) | 1987-11-19 |
Family
ID=14577443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11207586A Pending JPS62267293A (en) | 1986-05-15 | 1986-05-15 | Method for purifying sucrose fatty acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62267293A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0424066A2 (en) * | 1989-10-16 | 1991-04-24 | The Procter & Gamble Company | Polyol polyester synthesis |
| JP2009173658A (en) * | 2003-01-06 | 2009-08-06 | Color Access Inc | Alignment of enhancer in cosmetic composition |
-
1986
- 1986-05-15 JP JP11207586A patent/JPS62267293A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0424066A2 (en) * | 1989-10-16 | 1991-04-24 | The Procter & Gamble Company | Polyol polyester synthesis |
| JP2009173658A (en) * | 2003-01-06 | 2009-08-06 | Color Access Inc | Alignment of enhancer in cosmetic composition |
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