JPS62129294A - Production of sucrose fatty acid ester - Google Patents
Production of sucrose fatty acid esterInfo
- Publication number
- JPS62129294A JPS62129294A JP60270270A JP27027085A JPS62129294A JP S62129294 A JPS62129294 A JP S62129294A JP 60270270 A JP60270270 A JP 60270270A JP 27027085 A JP27027085 A JP 27027085A JP S62129294 A JPS62129294 A JP S62129294A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- sucrose
- acid ester
- reaction
- dmso
- 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
- 229930006000 Sucrose Natural products 0.000 title claims abstract description 31
- 239000005720 sucrose Substances 0.000 title claims abstract description 31
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 26
- 239000000194 fatty acid Substances 0.000 title claims abstract description 26
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 26
- -1 sucrose fatty acid ester Chemical class 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 50
- 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 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 238000003756 stirring Methods 0.000 claims abstract description 11
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000007810 chemical reaction solvent Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 abstract description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 11
- 238000005886 esterification reaction Methods 0.000 description 10
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000000593 microemulsion method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- SZYSLWCAWVWFLT-UTGHZIEOSA-N [(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl octadecanoate Chemical compound O([C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@]1(COC(=O)CCCCCCCCCCCCCCCCC)O[C@H](CO)[C@@H](O)[C@@H]1O SZYSLWCAWVWFLT-UTGHZIEOSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 238000001641 gel filtration chromatography Methods 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- General Preparation And Processing Of Foods (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、ショ糖脂肪酸エステルの製造法に関する。さ
らに詳しくはジメチルスルホキシドを反応溶媒として使
用し、ショ糖と脂肪酸エステルとをアルカリ触媒の存在
下に反応させてなるショ糖脂肪酸エステル［以下ＳＥと
いう］の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing sucrose fatty acid ester. More specifically, the present invention relates to a method for producing sucrose fatty acid ester (hereinafter referred to as SE) by reacting sucrose and fatty acid ester in the presence of an alkali catalyst using dimethyl sulfoxide as a reaction solvent.
ＳＨの製造法は、数多く提案されているが、そのうち１
食品添加物としての製造を目的に、工業化されている製
造法としては、ジメチルホルムアミド、あるいはジメチ
ルスルホキシド［以下ＤＭＳＯという］を反応溶媒とし
て使用し、製造する溶媒法とアルカリ石鹸をショ糖と脂
肪酸エステルの溶融化剤として使用し、製造するミクロ
エマルジョン法の二つの方法がある。Many methods for producing SH have been proposed, but one of them is
Production methods that have been industrialized for the purpose of production as food additives include a solvent method in which dimethylformamide or dimethyl sulfoxide (hereinafter referred to as DMSO) is used as a reaction solvent, and a solvent method in which alkaline soap is produced using sucrose and fatty acid ester. There are two methods of manufacturing microemulsion using it as a melting agent.
ショ糖は、その分子内に８個の水酸基を含有することか
ら、ショ糖と脂肪酸エステルの反応モル比率を任意に調
整して反応することにより、ＨＬＢ値の異なるＳＥが製
造できる。Since sucrose contains eight hydroxyl groups in its molecule, SEs with different HLB values can be produced by arbitrarily adjusting the reaction molar ratio of sucrose and fatty acid ester.
例えば、水と油の乳化剤としてコーヒーホワイトなどに
使用される高いＨＬＢ値を有するＳＥを製造するには、
ショ糖の仕込みモル数を脂肪酸エステルの仕込みモル数
に対して過剰量使用して反応させる。また、低いＨＬＢ
値を有するＳＥを製造するには、逆にショ糖に対して脂
肪酸エステルを過剰量使用して反応させることにより得
られる。For example, to produce SE with a high HLB value, which is used as an emulsifier for water and oil in coffee white, etc.
The reaction is carried out by using an excess amount of sucrose in moles relative to the amount of fatty acid ester in moles. Also, low HLB
In order to produce SE having a certain value, conversely, it can be obtained by reacting fatty acid ester with excess amount of sucrose.
また、一般に高ＨＬＢ値のＳＥを製造する場合には、溶
媒法が適している。即ち、比較的低温１例えば、７０〜
９０℃の温度で反応が容易に進行するため、前述した通
り、過剰量使用したショ糖の−うち、未反応として、相
当量残存するが、これらのショ糖は、熱による分解等を
、はとんど受けず、安定な状態であることから、その未
反応ショ糖を容易に回収して再使用することができる。Further, in general, when producing an SE with a high HLB value, a solvent method is suitable. That is, relatively low temperature 1, for example, 70~
Since the reaction proceeds easily at a temperature of 90°C, as mentioned above, a considerable amount of the excess sucrose remains as unreacted, but this sucrose is resistant to decomposition due to heat. Since the unreacted sucrose is hardly affected and is in a stable state, the unreacted sucrose can be easily recovered and reused.
つまり、製造コストが安くなり、工業化のメリットが大
きい。In other words, manufacturing costs are lower, and there are great benefits to industrialization.
逆に、低ＨＬＢ値のＳＥを製造する場合は、ミクロエマ
ルジョン法が適している。On the other hand, when producing SE with a low HLB value, the microemulsion method is suitable.
即ち、比較的高温、例えば、１４０〜１８０℃の温度で
反応させる方法であることから、ショ糖が持っている８
個の水酸基のうち１反応性が低い５個の二級水酸基を効
率的に反応させることができるためである。That is, since the reaction is carried out at a relatively high temperature, for example, 140 to 180°C, the 8
This is because five secondary hydroxyl groups, one of which has a low reactivity among the hydroxyl groups, can be efficiently reacted.
この場合、溶媒法では使用する溶媒の訓点の関係上、１
００°Ｃ以上の温度による反応は難しく、また溶媒法の
特徴として挙げられている製品の着色にも影響を及ぼす
。In this case, in the solvent method, due to the precepts of the solvent used, 1
Reactions at temperatures above 00°C are difficult and also affect the coloration of the product, which is a feature of the solvent method.
本発明者らは、これら問題点を解消すべく鋭意研究の結
果、ＤＭＳＯを反応溶媒に使用した溶媒法で、低減化Ｈ
ＬＢ値を有するＳＥの製造法を見い出したものである。As a result of intensive research to solve these problems, the present inventors have succeeded in reducing H
A method for producing SE having a LB value has been discovered.
即ち、本発明は、
ジメチルスルホキシドを反応溶媒として使用し、ショ糖
と脂肪酸エステルとを、アルカリ触媒の存在下に反応さ
せてショ糖脂肪酸エステルを製造する方法において、７
０〜９０℃の反応温度で、ジメチルスルホキシドが沸騰
する減圧下において、反応を完結した後、さらに、その
状態を維持しながら攪拌を続けることを特徴とする、低
減化ＨＬＢ値を有するショ糖脂肪酸エステルの製造法を
提供するものである。That is, the present invention provides a method for producing sucrose fatty acid ester by reacting sucrose and fatty acid ester in the presence of an alkali catalyst using dimethyl sulfoxide as a reaction solvent.
A sucrose fatty acid having a reduced HLB value, which is characterized in that after the reaction is completed at a reaction temperature of 0 to 90°C and under reduced pressure where dimethyl sulfoxide boils, stirring is continued while maintaining that state. A method for producing an ester is provided.
この場合、反応温度が７０〜９０℃におてＤＭＳＯが沸
騰する真空度は、例えば、７０℃では、約１０ｍｍＨｇ
以下、また９０°Ｃでは、約２８ ｍ ｍＨｇ以下であ
る。In this case, the degree of vacuum at which DMSO boils at a reaction temperature of 70 to 90°C is, for example, approximately 10 mmHg at 70°C.
Below, and at 90°C, it is about 28 m mHg or below.
本発明によれば、理論値より、過剰量必要とされるシヨ
糖、脂肪酸エステルの仕込みモル比率および両成分の仕
込み合計量よりも少ないモル比率および仕込み合計量で
任意の低減化ＨＬＥ値を有するＳＥが得られることから
、ショ糖と脂肪酸エステルの利用率は高く、必然的に高
収率でＳＥが得られ、また高温を必要とするミクロエマ
ルジョン法に比べて、７０〜９０℃と比較的低温で低減
化ＨＬＢを有するＳＥが得られることから、製品の着色
度も少なく、エネルギーコストも低いことなどから、工
業化には極めて有利な方法である。According to the present invention, an arbitrary reduced HLE value can be obtained at a molar ratio and a total amount of the charged sucrose and fatty acid ester that are smaller than the theoretical value and the total amount of the two components. Since SE can be obtained, the utilization rate of sucrose and fatty acid ester is high, and SE is naturally obtained in high yield.Also, compared to the microemulsion method which requires high temperature, the temperature is relatively low at 70 to 90℃. Since SE having a reduced HLB can be obtained at low temperatures, the degree of coloration of the product is low, and the energy cost is low, so it is an extremely advantageous method for industrialization.
本発明で使用する蔗糖は、その品質形態に関して、はと
んど制限ない、即ち、重版のグラニユー糖、上白糖など
の固形の蔗糖は、いずれも使用できる。脂肪酸エステル
は、一般にＳＨの製造に使用される炭素数８〜２２の高
級脂肪酸と炭素数４以下の低級−価アルコールとのエス
テルである。The quality of the sucrose used in the present invention is not limited in terms of its form; in other words, any solid sucrose such as reprinted granulated sugar or caster sugar can be used. The fatty acid ester is an ester of a higher fatty acid having 8 to 22 carbon atoms and a lower-hydric alcohol having 4 or less carbon atoms, which is generally used in the production of SH.
脂肪酸成分は不飽和結合および／または分岐鎖を有して
もよい。脂肪酸エステルの混合物でもよい、蔗糖と脂肪
酸エステルとのエステル化触媒として、炭酸カリウム、
炭酸ナトリウム、水酸化カリウム、水酸化ナトリウムな
どの無機アルカリ化合物、ナトリウムエチラート、カリ
ウムメチラートなどの有機アルカリ化合物が使用される
。触媒は蔗糖に対して０．１〜６％、好ましくは１〜３
％使用する。The fatty acid component may have unsaturated bonds and/or branched chains. Potassium carbonate,
Inorganic alkali compounds such as sodium carbonate, potassium hydroxide, and sodium hydroxide, and organic alkali compounds such as sodium ethylate and potassium methylate are used. The catalyst is 0.1 to 6%, preferably 1 to 3% based on sucrose.
%use.
反応原料の添加方法としては、特に制限はないが、通常
、次の様な一般的な操作法に従って製造する。 まず、
７０〜９０℃に加熱されたＤＭＳＯ液中にショ糖を添加
して溶解させ、その後５０〜ＬＯＯｍｍＨｇ、好ましく
は７０〜８０ｍｍＨｇに減圧し、脱水操作を行なう０次
いで、触媒を添加し、再び５０〜１００ｍｍＨｇ、好ま
しくは７０〜８０ ｍｍＨｇで脱水する。脱水後、常圧
に戻し、脂肪酸エステルを添加し、７０〜９０°Ｃの温
度範囲でＤＭＳＯが沸騰する状態１例えば８〜２５ ｍ
ｍＨｇ程度の減圧下で、エステル化反応させる。There are no particular restrictions on the method of adding the reaction raw materials, but they are usually produced according to the following general operating method. first,
Add sucrose to the DMSO solution heated to 70-90°C to dissolve it, then reduce the pressure to 50-LOO mmHg, preferably 70-80 mmHg, and perform a dehydration operation. Dehydrate at 100 mmHg, preferably 70-80 mmHg. After dehydration, return to normal pressure, add fatty acid ester, and boil DMSO in a temperature range of 70 to 90 ° C. 1 For example, 8 to 25 m
The esterification reaction is carried out under reduced pressure of approximately mHg.
この場合、反応時間としては反応装置のスケールおよび
仕込み量、あるいは脂肪酸エステルの種類等により適性
な時間を選択することができるが、通常０．５〜３時間
程度でよい。In this case, an appropriate reaction time can be selected depending on the scale of the reactor, the amount charged, the type of fatty acid ester, etc., but it is usually about 0.5 to 3 hours.
この様にしてエステル化反応を完結させた後、その状態
を維持しながら、さらに攪拌を続ける。After completing the esterification reaction in this manner, stirring is continued while maintaining this state.
この場合の時間は前述のエステル化反応時間と同様に、
反応装置のスケールおよび仕込み量、あるいは脂肪酸エ
ステルの種類等により異なるが１通常１〜３時間で充分
である。In this case, the time is the same as the esterification reaction time described above.
Although it varies depending on the scale of the reactor, the amount charged, the type of fatty acid ester, etc., 1 to 3 hours is usually sufficient.
以上の様な操作により、ショ糖と脂肪酸エステルとの仕
込みモル比率を同じくしても、従来法によるＳＥに比べ
て、さらに低い即ち、低減化ＨＬＢ値を有するＳＥが製
造できる。By the above-described operation, even if the molar ratio of sucrose and fatty acid ester is the same, an SE having a lower HLB value than that of the conventional SE can be produced.
本発明において、何故、低減化ＨＬＢ値のＳＥが得られ
るのか、その解明は明確でないが、ミクロエマルジョン
法、および溶媒法でもジメチルホルムアミドを用いた場
合は、この様な現象が起こらないことから、ＤＭＳＯを
用いることによることが、ひとつの要因として考えられ
る。In the present invention, it is not clear why the SE of the reduced HLB value is obtained, but since this phenomenon does not occur when dimethylformamide is used in the microemulsion method and the solvent method, One of the factors is thought to be due to the use of DMSO.
また、エステル化の平衡時点では、通常のＨＬＢ値であ
るにかかわらず、それから、さらに攪拌を続けることに
より、ＨＬＢ値の低下が発生することが判明したので、
その状７ｇで何らかの影響により各エステルの平衡移動
が発生するものと推測できる。In addition, it was found that even if the HLB value is normal at the equilibrium point of esterification, the HLB value will decrease if stirring is continued.
It can be inferred that equilibrium movement of each ester occurs due to some influence at 7 g of that state.
なお、ここで言うエステル化の平衡時点とは、反応に使
用される脂肪酸エステルの消費量を、例えばガスクロマ
トグラフィー等を使用して定量し。Note that the equilibrium point of esterification as referred to herein means that the consumption amount of fatty acid ester used in the reaction is quantified using, for example, gas chromatography.
その量が、もはや、それ以上、下らない点を意味する。It means that the amount no longer decreases.
以下、本発明を実施例により具体的に説明する。Hereinafter, the present invention will be specifically explained with reference to Examples.
実施例１
攪拌機、温度計、減圧装置、およびＤＭＳＯの速流装置
を備えた１１フラスコに、ＤＭＳＯを５゜Ｏｍｌ仕込み
、９０℃まで攪拌しながら、加熱した。その中ニシヨ糖
１５４．４ｇ ［０，４５１％ル］を添加して溶解させ
、系内を７０ ｍ ｍ Ｈｇまで減圧にし、３０分間脱
水した。Example 1 5° Oml of DMSO was charged into a No. 11 flask equipped with a stirrer, a thermometer, a pressure reducing device, and a DMSO rapid flow device, and heated to 90° C. while stirring. Into the mixture, 154.4 g [0.451% L] of western sugar was added and dissolved, the pressure inside the system was reduced to 70 mm Hg, and the mixture was dehydrated for 30 minutes.
常圧に戻して炭酸カリウムを２．０ｇ［０，０１４モル
コ添加し、再び系内を７０ ｍｍＨｇまで減圧にし、１
０分間脱水した。The pressure was returned to normal, 2.0 g [0,014 mol] of potassium carbonate was added, and the pressure inside the system was reduced to 70 mmHg again.
Dehydrated for 0 minutes.
常圧に戻して、ステアリン酸メチルを４４．０ｇ［０，
１５０％ル］加えた後、系内を１５ｍｍＨｇまで減圧に
し、１．５時間エステル化反応を行った。Return to normal pressure and add 44.0g of methyl stearate [0,
After adding 150% L], the pressure inside the system was reduced to 15 mmHg, and the esterification reaction was carried out for 1.5 hours.
反応中、温度は８５°Ｃであり、ＤＭＳＯは沸隠しなが
ら還流された状態であった。During the reaction, the temperature was 85°C, and the DMSO was under reflux while being boiled.
エステル化反応終了後、常圧に戻し１反応液を一部抜き
取って［サンプル（ａ）］分析するとともに、さらに、
再び反応時と同じ状態で２時間攪拌を続けた後、この反
応液［サンプル（ｂ）］も分析した。After the esterification reaction is completed, the pressure is returned to normal pressure, a portion of the reaction solution is extracted and analyzed [sample (a)], and further,
After stirring was continued for 2 hours under the same conditions as during the reaction, this reaction solution [sample (b)] was also analyzed.
［サンプル（ａ）］ 、および［サンプル（ｂ）］の分
析結果を表−１に示した。The analysis results of [Sample (a)] and [Sample (b)] are shown in Table-1.
表−１の結果より、ステアリン酸メチルの反応率は［サ
ンプル（ａ）］ 、および［サンプル（ｂ）］ とも、
はとんど変らないが、エステル組成には、明らかに変化
が認められ、［サンプル（ａ）］に比べＣサンプル（ｂ
〕］では、それよりも低いＨＬＢ値のショ糖ステアリン
酸エステルが得られた。From the results in Table 1, the reaction rate of methyl stearate is as follows for both [sample (a)] and [sample (b)].
There is almost no change in the ester composition, but there is a clear change in the ester composition, and compared to [sample (a)], sample C (b)
]], sucrose stearate with a lower HLB value was obtained.
尚、分析中、ステアリン酸メチルの反応率は、ガスクロ
マトグラフィーを使用して、未反応のステアリン酸メチ
ルを定量することにより算出 し、エステル組成は、ゲ
ル濾過クロマトグラフィーより、各々エステル値を求め
た。また、ＨＬＢ値は油脂の安定した乳化状態で判定す
る乳化法で測定した。During the analysis, the reaction rate of methyl stearate was calculated by quantifying unreacted methyl stearate using gas chromatography, and the ester composition was determined by determining each ester value using gel filtration chromatography. Ta. In addition, the HLB value was measured by an emulsification method that determines the stable emulsified state of fats and oils.
比較例１
実施例１と全く同じ装置、原料を用いて、１．５時間の
エステル化反応までは同じ操作で行い、ここで［サンプ
ル（Ｃ）］をした後、真空度を７０ｍｍＨＨにして、Ｄ
ＭＳＯを琲騰させない状態で、同様に２時間攪拌した後
の反応液［サンプル（ｄ）］を分析した。Comparative Example 1 Using exactly the same equipment and raw materials as in Example 1, the same operations were carried out up to the esterification reaction for 1.5 hours.After performing [sample (C)] here, the degree of vacuum was set to 70 mmHH, D
The reaction solution [sample (d)] was analyzed after stirring for 2 hours in the same manner without stirring the MSO.
［サンプル（ｃ）］ 、および［サンプル（ｄ）］の分
析結果を表−２に示した。The analysis results of [Sample (c)] and [Sample (d)] are shown in Table 2.
表−２から明らかなように、［サンプル（Ｃ）］と［サ
ンプル（ｄ）］のステアリン酸メチルの反応率、ＨＬＢ
値に、はとんど変化は認められないことから、エステル
化反応終了後、ＤＭＳＯを沸臆させながら反応すること
によってのみＨＬＢ値の低いＳＥが得られることが確認
できる。As is clear from Table 2, the reaction rate of methyl stearate of [Sample (C)] and [Sample (d)], HLB
Since there is almost no change in the value, it can be confirmed that SE with a low HLB value can be obtained only by reacting while boiling DMSO after the esterification reaction is completed.
実施例２
実施例１と全く同じ装置、操作で、原料は同じであるが
、ショ糖とステアリン酸メチルの仕込みモル比率を表−
３に記載の通り、変えて行った。その分析結果を表−３
に示した。Example 2 The equipment and operation were exactly the same as in Example 1, and the raw materials were the same, but the molar ratios of sucrose and methyl stearate were as follows:
The changes were made as described in 3. Table 3 shows the analysis results.
It was shown to.
表−３から明らかなように、ショ糖とステアリン酸メチ
ルの仕込みモリ比率を変えて、エステル化反応終了後、
ＤＭＳＯの浪騰下で撹拌を続けることにより、［サンプ
ル（ｆ）］、［サンプル（ｈ）］に見られるようなＨＬ
Ｂ値の異なるショ糖ステアリン酸エステルが得られるこ
とを確認した。As is clear from Table 3, by changing the charging ratio of sucrose and methyl stearate, after the esterification reaction was completed,
By continuing to stir under the rising of DMSO, HL as seen in [sample (f)] and [sample (h)]
It was confirmed that sucrose stearate esters having different B values could be obtained.
表−１ 表−２Table-1 Table-2
Claims (1)
と脂肪酸エステルとを、アルカリ触媒の存在下に反応さ
せてショ糖脂肪酸エステルを製造する方法において、７
０〜９０℃の反応温度で、ジメチルスルホキシドが沸騰
する減圧下において、反応を完結した後、さらに、その
状態を維持しながら攪拌を続けることを特徴とする、低
減化ＨＬＢ値を有するショ糖脂肪酸エステルの製造法。In a method for producing sucrose fatty acid ester by reacting sucrose and fatty acid ester in the presence of an alkali catalyst using dimethyl sulfoxide as a reaction solvent, 7
A sucrose fatty acid having a reduced HLB value, which is characterized in that after the reaction is completed at a reaction temperature of 0 to 90°C and under reduced pressure where dimethyl sulfoxide boils, stirring is continued while maintaining that state. Method for producing esters.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60270270A JPS62129294A (en) | 1985-11-30 | 1985-11-30 | Production of sucrose fatty acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60270270A JPS62129294A (en) | 1985-11-30 | 1985-11-30 | Production of sucrose fatty acid ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62129294A true JPS62129294A (en) | 1987-06-11 |
Family
ID=17483908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60270270A Pending JPS62129294A (en) | 1985-11-30 | 1985-11-30 | Production of sucrose fatty acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62129294A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01143888A (en) * | 1987-11-30 | 1989-06-06 | Kurooda Japan Kk | Production of sugaralcohol fatty acid ester with high monoester content |
| US5565557A (en) * | 1993-12-24 | 1996-10-15 | Mitsubishi Chemical Corporation | Process for producing sucrose fatty acid ester |
-
1985
- 1985-11-30 JP JP60270270A patent/JPS62129294A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01143888A (en) * | 1987-11-30 | 1989-06-06 | Kurooda Japan Kk | Production of sugaralcohol fatty acid ester with high monoester content |
| US5565557A (en) * | 1993-12-24 | 1996-10-15 | Mitsubishi Chemical Corporation | Process for producing sucrose fatty acid ester |
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