JP2630182B2 - Method for producing sucrose fatty acid ester - Google Patents

Method for producing sucrose fatty acid ester

Info

Publication number
JP2630182B2
JP2630182B2 JP4242306A JP24230692A JP2630182B2 JP 2630182 B2 JP2630182 B2 JP 2630182B2 JP 4242306 A JP4242306 A JP 4242306A JP 24230692 A JP24230692 A JP 24230692A JP 2630182 B2 JP2630182 B2 JP 2630182B2
Authority
JP
Japan
Prior art keywords
fatty acid
reaction
stage condenser
condenser
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.)
Expired - Fee Related
Application number
JP4242306A
Other languages
Japanese (ja)
Other versions
JPH06122694A (en
Inventor
成男 深谷
和彦 政岡
寛 山本
壽龍 高橋
行雄 加曽利
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Chemical Corp
Original Assignee
Mitsubishi Chemical Corp
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Filing date
Publication date
Application filed by Mitsubishi Chemical Corp filed Critical Mitsubishi Chemical Corp
Priority to JP4242306A priority Critical patent/JP2630182B2/en
Publication of JPH06122694A publication Critical patent/JPH06122694A/en
Application granted granted Critical
Publication of JP2630182B2 publication Critical patent/JP2630182B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/52Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

  • Saccharide Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Biological Depolymerization Polymers (AREA)

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【0001】[0001]

【産業上の利用分野】本発明は、ショ糖脂肪酸エステル
(以下、SEと略記する)の製造法に関する。詳しくは
本発明は、効率的な反応器(反応システム)を用いて、
ショ糖と脂肪酸アルキルエステルとのエステル交換反応
を行うことによりSEを製造する方法に関する。
The present invention relates to a method for producing a sucrose fatty acid ester (hereinafter abbreviated as SE). Specifically, the present invention uses an efficient reactor (reaction system),
The present invention relates to a method for producing SE by performing a transesterification reaction between sucrose and a fatty acid alkyl ester.

【0002】[0002]

【従来の技術】SEは優れた界面性能、良好な生分解性
及び高い安全性を兼備しているので、従来、食品、化粧
品、医薬品、台所用洗剤、飼料、樹脂等の添加剤とし
て、また化学工業においては、例えば重合反応、酸化反
応等の、反応系の助剤として用いられており、極めて有
用な化合物である。
2. Description of the Related Art SE has excellent interfacial performance, good biodegradability and high safety, and is conventionally used as an additive for foods, cosmetics, pharmaceuticals, kitchen detergents, feeds, resins, and the like. In the chemical industry, it is used as an auxiliary for a reaction system such as a polymerization reaction and an oxidation reaction, and is a very useful compound.

【0003】従来SEの製造方法として、ジメチルホル
ムアミド、ジメチルスルホキシド(以下DMSOと略記
する)等の有機溶媒中で、アルカリ触媒の存在下、ショ
糖と脂肪酸アルキルエステルとを反応させる方法、有機
溶媒を用いずに水を使用してショ糖を脂肪酸石鹸と共に
溶融混合物とした後、アルカリ触媒の存在下、脂肪酸ア
ルキルエステルを反応させる方法、更にはショ糖と脂肪
酸とを特定酵素の存在下に直接反応させるいわゆるバイ
オ法等が知られている。
Conventional methods for producing SE include a method of reacting sucrose with a fatty acid alkyl ester in an organic solvent such as dimethylformamide or dimethylsulfoxide (hereinafter abbreviated as DMSO) in the presence of an alkali catalyst. A method in which sucrose is melted with fatty acid soap using water without using water, and then a fatty acid alkyl ester is reacted in the presence of an alkali catalyst.Furthermore, sucrose and fatty acid are directly reacted in the presence of a specific enzyme. There is known a so-called biomethod.

【0004】これらの方法はいずれも一長一短はある
が、DMSOを用いる溶媒法は比較的低温で反応がで
き、副生するアルコールを反応系外に除去することによ
り反応を進行させることができ工業的実績も大きい。副
生アルコールを容易に反応系外に除去するDMSO溶媒
法として、DMSO溶媒中に低級アルキルベンゼン類を
存在させて温和な条件下で行う方法(特公昭58−21
637)が提案されているが、人体に有毒な低級アルキ
ルベンゼン類を使用する問題点がある。
Although all of these methods have advantages and disadvantages, the solvent method using DMSO can carry out the reaction at a relatively low temperature, and the reaction can proceed by removing the by-product alcohol to the outside of the reaction system. The achievements are also large. As a DMSO solvent method for easily removing by-product alcohol out of the reaction system, a method in which lower alkylbenzenes are present in a DMSO solvent under mild conditions (Japanese Patent Publication No. 58-21)
637) has been proposed, but there is a problem in that lower alkylbenzenes toxic to the human body are used.

【0005】有害な溶媒を併用しないDMSO溶媒法で
は、副生アルコールを効率よく除去することは同時にD
MSO溶媒の反応留出にもつながり、結果としてDMS
O溶媒濃度を一定に保つことが困難となり、所望の品質
が得られなくなる。一方DMSO溶媒濃度を一定に保つ
とアルコールの円滑な除去が妨げられ反応速度が遅延す
るなど、より効率的な反応方法が求められている。
In the DMSO solvent method in which no harmful solvent is used, the efficient removal of by-product alcohol is at the same time as the DSO method.
This also leads to the distilling off of the MSO solvent, resulting in DMS
It becomes difficult to keep the O solvent concentration constant, and desired quality cannot be obtained. On the other hand, if the concentration of the DMSO solvent is kept constant, a more efficient reaction method is required, for example, the smooth removal of alcohol is hindered and the reaction rate is delayed.

【0006】[0006]

【発明が解決しようとする課題】本発明は、DMSO溶
媒の存在下、エステル交換反応によりSEを製造する方
法において、反応速度を遅延させることなくDMSO濃
度を一定に保持する効率的な反応システムを提供するも
のである。
SUMMARY OF THE INVENTION The present invention provides a method for producing SE by transesterification in the presence of a DMSO solvent, which comprises an efficient reaction system for maintaining a constant DMSO concentration without delaying the reaction rate. To provide.

【0007】[0007]

【課題を解決するための手段】本発明の要旨は、アルカ
リ触媒の存在下、DMSOを溶媒としてショ糖と脂肪酸
アルキルエステルとのエステル交換反応によりショ糖脂
肪酸エステルを製造する方法において、充填塔と複数個
の凝縮器とを直列に配置した反応器を使用し、且つ第1
段凝縮器の凝縮液を充填塔の塔頂に還流することを特徴
とするショ糖脂肪酸エステルの製造法にある。
The gist of the present invention is to provide a method for producing a sucrose fatty acid ester by a transesterification reaction between sucrose and a fatty acid alkyl ester using DMSO as a solvent in the presence of an alkali catalyst. A reactor in which a plurality of condensers are arranged in series;
A method for producing a sucrose fatty acid ester, comprising refluxing a condensate from a stage condenser to the top of a packed column.

【0008】以下、本発明を詳細に説明する。本発明に
おける脂肪酸アルキルエステルとしては、炭素数6〜3
0、好ましくは12〜22の飽和または不飽和脂肪酸
(例えばカプロン酸、カプリン酸、ラウリン酸、ミリス
チン酸、パルミチン酸、ステアリン酸、ベヘニン酸など
の飽和脂肪酸;リノール酸、オレイン酸、リノレイン
酸、エルカ酸、リシノール酸などの不飽和脂肪酸など)
と炭素数1〜6の低級アルコール(例えばメタノール、
エタノール、プロパノール、ブタノールなど)とのエス
テルが挙げられる。かかる脂肪酸アルキルエステルは、
2種以上の混合物として用いてもよい。脂肪酸アルキル
エステルは、ショ糖1モルに対して通常0.1〜20モ
ル、好ましくは0.2〜8モル使用する。
Hereinafter, the present invention will be described in detail. The fatty acid alkyl ester in the present invention has 6 to 3 carbon atoms.
0, preferably 12 to 22 saturated or unsaturated fatty acids (for example, saturated fatty acids such as caproic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid; linoleic acid, oleic acid, linoleic acid, elka Acid, unsaturated fatty acid such as ricinoleic acid)
And a lower alcohol having 1 to 6 carbon atoms (eg, methanol,
Esters with ethanol, propanol, butanol, etc.). Such fatty acid alkyl esters are:
It may be used as a mixture of two or more. The fatty acid alkyl ester is used in an amount of usually 0.1 to 20 mol, preferably 0.2 to 8 mol, per 1 mol of sucrose.

【0009】反応溶媒としては、熱的安定性、ショ糖に
対する溶解性および安全性の点からして、DMSOが用
いられる。溶媒の使用量は、ショ糖と脂肪酸低級アルコ
ールエステルとの合計仕込量に対して、通常20〜15
0重量%、好ましくは30〜80重量%である。アルカ
リ触媒としては、アルカリ金属水素化物、アルカリ金属
水酸化物、弱酸のアルカリ金属塩等が有効であり、特に
炭酸アルカリ金属塩(例えば炭酸カリウムなど)が好ま
しい。
As a reaction solvent, DMSO is used in view of thermal stability, solubility in sucrose and safety. The amount of the solvent used is usually 20 to 15 with respect to the total charged amount of sucrose and fatty acid lower alcohol ester.
0% by weight, preferably 30 to 80% by weight. As the alkali catalyst, an alkali metal hydride, an alkali metal hydroxide, an alkali metal salt of a weak acid, or the like is effective, and an alkali metal carbonate (eg, potassium carbonate) is particularly preferable.

【0010】反応温度は通常40〜150℃の範囲が採
用され、特に60〜130℃の範囲が好ましい。反応圧
力は通常0.01〜200mmHgの範囲が採用され、
特に0.1〜70mmHgの範囲が好ましい。本発明に
おける最も大きな特徴は、充填塔と複数個の凝縮器とを
直列に配置した反応器を使用し且つ第1段凝縮器の凝縮
液を充填塔塔頂に還流させながら反応を行うことにあ
る。かかる組み合わせにより反応溶媒として用いたDM
SOと、反応で副生したアルコールを効率的に分離する
ことができ、良好な精留効果が発揮される。
[0010] The reaction temperature is usually in the range of 40 to 150 ° C, particularly preferably in the range of 60 to 130 ° C. The reaction pressure is usually in the range of 0.01 to 200 mmHg,
Particularly, the range of 0.1 to 70 mmHg is preferable. The most significant feature of the present invention is that the reaction is carried out while using a reactor in which a packed column and a plurality of condensers are arranged in series, and refluxing the condensate of the first stage condenser to the top of the packed column. is there. DM used as a reaction solvent by such a combination
SO and the alcohol by-produced in the reaction can be efficiently separated, and a good rectification effect is exhibited.

【0011】充填塔は構造が簡単で製作が容易であり且
つガスの圧力損失が少ないなどの特徴を有する。これに
対し、棚段塔、泡鐘塔形式等では圧力損失が大きく、良
好な精留効果があがらない。充填塔の充填物としては、
ラッシヒリング、ベルルサドル、マクマホン、キャノ
ン、ステッドマン、スルーザーパッキンおよびディクソ
ン等が有効である。充填塔の理論段数としては、通常1
〜20段の範囲が採用され、特に1〜10段の範囲が好
ましい。
The packed tower has features such as a simple structure, easy manufacture, and low gas pressure loss. On the other hand, in a tray column, a bubble bell tower, or the like, the pressure loss is large and a good rectification effect is not obtained. As the packing for the packed tower,
Raschig rings, Berl saddles, McMahons, Cannons, Steadmans, Sulzer packings, Dicksons and the like are effective. The theoretical number of packed columns is usually 1
A range of up to 20 steps is employed, and a range of 1 to 10 steps is particularly preferred.

【0012】本発明においては、充填塔の下流に複数個
の凝縮器が接続される。凝縮器は少なくとも2個好まし
くは3個用いられる。4個以上設けてもよいが特別の利
点は得られ難い。第1段凝縮器の目的は、副生メタノー
ルを反応系外へ除去する一方、DMSOを凝縮させ、回
収し、充填塔塔頂に還流することである。この様な目的
のため温度は通常50〜100℃の範囲が採用され、特
に40〜70℃が好ましい。副生メタノールを反応系外
へ除去しないと、反応速度の遅延の原因となる。また凝
縮液の主成分はDMSOであるので、これを還流せずに
系外に除去すると、反応系内のDMSO溶媒濃度が一定
に保たれないため、エステル組成が変化し、所望の品質
が得られなくなる。またDMSO濃度が低くなりすぎ
て、反応が進行しなくなってしまうなどの問題が生じ
る。
In the present invention, a plurality of condensers are connected downstream of the packed tower. At least two, and preferably three, condensers are used. Four or more may be provided, but a special advantage is hardly obtained. The purpose of the first-stage condenser is to condense and recover DMSO while removing by-product methanol to the outside of the reaction system, and to reflux to the top of the packed column. For such a purpose, the temperature is usually in the range of 50 to 100C, and particularly preferably 40 to 70C. If the by-product methanol is not removed to the outside of the reaction system, the reaction rate will be delayed. In addition, since the main component of the condensate is DMSO, if this is removed from the system without reflux, the concentration of the DMSO solvent in the reaction system cannot be kept constant, so that the ester composition changes and the desired quality is obtained. Can not be. In addition, there is a problem that the DMSO concentration becomes too low and the reaction does not proceed.

【0013】第2段凝縮器の目的は、主として副生メタ
ノールを凝縮・回収することであり、合わせて第1段凝
縮器で未回収部分のDMSOを凝縮・回収することにあ
る。温度は、通常−20〜50℃の範囲が採用され、特
に−5〜30℃の範囲が好ましい。第3段凝縮器の目的
は、主として第2段凝縮器で未回収部分の副生メタノー
ルを完全に凝縮・回収し、真空系に接続することにあ
る。温度は、通常−10℃以下の範囲が採用され、−4
0〜−20℃の範囲が好ましい。
The purpose of the second-stage condenser is mainly to condense and recover by-product methanol, and also to condense and recover the unrecovered portion of DMSO in the first-stage condenser. The temperature is usually in the range of -20 to 50C, and particularly preferably in the range of -5 to 30C. The purpose of the third-stage condenser is to completely condense and recover the unrecovered portion of the by-product methanol mainly in the second-stage condenser, and connect it to a vacuum system. The temperature is usually in the range of −10 ° C. or less, and −4 ° C.
A range from 0 to -20C is preferred.

【0014】本発明における真空系としては、機械式真
空ポンプ、拡散ポンプ等のポンプ、及びガスエジェクタ
ー、スチームエジェクターなどが有効である。
As the vacuum system in the present invention, pumps such as a mechanical vacuum pump and a diffusion pump, a gas ejector and a steam ejector are effective.

【0015】[0015]

【実施例】以下に実施例を挙げて詳述するが、本発明は
その要旨を超えない限りこれらの実施例によって限定さ
れるものではない。 実施例1 図1に示す反応装置を使用した。
The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples unless it exceeds the gist. Example 1 The reactor shown in FIG. 1 was used.

【0016】(DMSO脱水工程)反応器1にショ糖9
4.8部、及び溶媒としてDMSO400部を仕込み、
真空装置6により20mmHgの圧力とし、90℃の加
熱下、溶媒を沸騰させた。溶媒蒸気を直径2cm、高さ
15cmの充填塔2(充填物としては、直径3mmのデ
ィクソン型パッキンを高さ9cmまで充填し、理論段数
を3段とした)を通過させた後、第1凝縮器3(冷媒温
度45℃)にて冷却し、凝縮液の全量を充填塔上部に還
流させた。還流開始20分後から凝縮液の一部を系外に
除去し、反応器内を脱水した。DMSOの留出量が50
部に達した時点で留去を止め、反応器内液の水分を測定
したところ0.06重量%であった。
(DMSO dehydration step) Sucrose 9
4.8 parts and 400 parts of DMSO were charged as a solvent,
The pressure was adjusted to 20 mmHg by the vacuum device 6, and the solvent was boiled under heating at 90 ° C. After passing the solvent vapor through a packed tower 2 having a diameter of 2 cm and a height of 15 cm (as a packing, a Dickson-type packing having a diameter of 3 mm was filled to a height of 9 cm and the number of theoretical plates was set to 3), the first condensation was performed. Cooling was performed in the vessel 3 (refrigerant temperature: 45 ° C.), and the entire amount of the condensate was refluxed to the upper portion of the packed tower. After 20 minutes from the start of reflux, a part of the condensate was removed from the system, and the inside of the reactor was dehydrated. DMSO distillate 50
At the time when the amount of the solution reached the maximum, the water content of the liquid in the reactor was measured and found to be 0.06% by weight.

【0017】(エステル交換反応工程)次いで、反応器
1に無水炭酸カリウム0.767部、ステアリン酸メチ
ル55.2部を添加し、第2凝縮器4(冷媒温度2℃)
と第3凝縮器5(冷媒温度−30℃)を作動させ20m
mHgの圧力下、90℃に加熱した。反応器1からの発
生蒸気は充填塔2を通り、第1凝縮器3で大部分が凝縮
した。凝縮液の全量を充填塔上部に還流させた。還流開
始約5分後から第2凝縮器4と第3凝縮器5からも凝縮
液が得られるようになったので、それらを合わせて反応
系外に留去した。
(Transesterification step) Then, 0.767 parts of anhydrous potassium carbonate and 55.2 parts of methyl stearate were added to the reactor 1, and the second condenser 4 (refrigerant temperature 2 ° C.)
And the third condenser 5 (refrigerant temperature −30 ° C.) is operated to 20 m
Heated to 90 ° C. under mHg pressure. Most of the vapor generated from the reactor 1 passed through the packed column 2 and was condensed in the first condenser 3. The entire amount of the condensate was refluxed at the top of the packed column. Approximately 5 minutes after the start of reflux, condensed liquid began to be obtained from the second condenser 4 and the third condenser 5, and these were combined and distilled out of the reaction system.

【0018】留去した凝縮液を分析したところ、メタノ
ール99.3%、DMSO0.7%であった。留去した
メタノールから算出した脂肪酸メチル99%転換率の到
達時間は4.2時間であった。溶媒量は反応開始から終
了までほぼ一定であることが観察された。反応液をゲル
パーミエーションクロマトグラフィーで分析したところ
エステルの組成はモノエステルが82%であった。
Analysis of the condensed liquid distilled off revealed that it was 99.3% methanol and 0.7% DMSO. The time required to reach a 99% conversion of fatty acid methyl calculated from the distilled methanol was 4.2 hours. It was observed that the amount of solvent was almost constant from the start to the end of the reaction. When the reaction solution was analyzed by gel permeation chromatography, the composition of the ester was 82% for the monoester.

【0019】実施例2 ディクソン型パッキンの充填高さを変え、理論段数を
1.5段とした以外は実施例1と同様に行った。脂肪酸
メチル99%転換率の到達時間は4.4時間であった。
溶媒量は一定に保たれ、エステル組成はモノエステル8
1%であった。
Example 2 The procedure of Example 1 was repeated, except that the filling height of the Dickson packing was changed and the number of theoretical plates was changed to 1.5. The time to reach 99% conversion of fatty acid methyl was 4.4 hours.
The amount of solvent was kept constant and the ester composition was monoester 8
1%.

【0020】実施例3 ディクソン型パッキンの充填高さを変え、理論段数を
5.0段とした以外は実施例1と同様に行った。脂肪酸
メチル99%転換率の到達時間は4.2時間であった。
Example 3 The same procedure as in Example 1 was carried out except that the filling height of the Dickson type packing was changed and the theoretical plate number was changed to 5.0. The time to reach 99% conversion of fatty acid methyl was 4.2 hours.

【0021】比較例1 ディクソン型パッキンを充填しない(理論段数1段)こ
ととした以外は実施例1と同様に行った。脂肪酸メチル
99%転換率の到達時間は8.9時間であった。
Comparative Example 1 The procedure of Example 1 was repeated except that the Dickson type packing was not filled (the number of theoretical plates was one). The time to reach the 99% conversion of fatty acid methyl was 8.9 hours.

【0022】比較例2 凝縮器として第1凝縮器3のみを使用(第2凝縮器4と
第3凝縮器5は不使用)した以外は実施例1と同様に行
った。脂肪酸メチル99%転換率の到達時間は4.3時
間であった(反応液を経時的にサンプリングしてガスク
ロマトグラフィーにより未反応脂肪酸メチルを分析した
結果)。しかし、真空ポンプの、真空ポンプオイル中に
メタノールが混入したため、真空度が下がり、反応系内
の温度が上昇し、ショ糖脂肪酸エステルの着色の原因と
なった。
Comparative Example 2 The same operation as in Example 1 was performed except that only the first condenser 3 was used as the condenser (the second condenser 4 and the third condenser 5 were not used). The time to reach 99% conversion of fatty acid methyl was 4.3 hours (result of sampling the reaction solution with time and analyzing unreacted fatty acid methyl by gas chromatography). However, since methanol was mixed into the vacuum pump oil of the vacuum pump, the degree of vacuum was lowered, the temperature in the reaction system was raised, and the sucrose fatty acid ester was colored.

【0023】比較例3 充填塔の代わりに直径2cm、高さ15cmの還流冷却
器を用い、また凝縮器として第1凝縮器のみを使用した
以外は実施例1と同様に行った。10時間反応させた
後、ガスクロマトグラフィーで未反応脂肪酸メチルを分
析したところ、転換率は73%であった。また、比較例
2と同様に真空ポンプオイル中にメタノールが混入した
ため、真空度が不十分となった。
Comparative Example 3 The procedure of Example 1 was repeated, except that a reflux condenser having a diameter of 2 cm and a height of 15 cm was used instead of the packed tower, and only the first condenser was used as the condenser. After reacting for 10 hours, the unreacted fatty acid methyl was analyzed by gas chromatography, and the conversion was 73%. Further, as in the case of Comparative Example 2, methanol was mixed in the vacuum pump oil, so that the degree of vacuum was insufficient.

【0024】実施例4 脂肪酸メチルとしてステアリン酸メチル30%とパルミ
チン酸メチル70%の混合脂肪酸メチルを36.3部、
ショ糖113.0部、炭酸カリ0.73部、及びDMS
Oを400部仕込み、DMSOを50部留出させた後
(反応系内DMSO濃度70重量%)実施例1と同様に
行った。脂肪酸メチル99%の転換率の到達時間は5時
間であり、エステル組成はモノエステルが80%であっ
た。
Example 4 As a fatty acid methyl ester, 36.3 parts of a mixed fatty acid methyl ester composed of 30% of methyl stearate and 70% of methyl palmitate,
113.0 parts of sucrose, 0.73 part of potassium carbonate, and DMS
400 parts of O was charged, and 50 parts of DMSO was distilled off (DMSO concentration in the reaction system: 70% by weight). The time to reach the conversion of 99% fatty acid methyl was 5 hours, and the monoester composition was 80%.

【0025】比較例4 第1段凝縮器の凝縮液を充填塔に還流せずに系外に除去
した以外は実施例4と同様に行ったところ、10時間後
反応器内に残ったDMSOは130部であった。この時
点で脂肪酸メチルの転換率は80%にとどまっておりま
たモノエステルの組成は74%であった。
Comparative Example 4 The same procedure as in Example 4 was carried out except that the condensate in the first-stage condenser was removed from the system without refluxing to the packed column. After 10 hours, DMSO remaining in the reactor was 130 parts. At this point, the conversion of fatty acid methyl was only 80% and the monoester composition was 74%.

【0026】[0026]

【発明の効果】エステル交換反応に伴うアルコールの除
去が円滑で、かつDMSO溶媒濃度を一定に保持するこ
とができる。反応速度が大きく、かつ品質の高いSEを
製造することができる。
According to the present invention, the removal of alcohol accompanying the transesterification reaction can be carried out smoothly, and the concentration of the DMSO solvent can be kept constant. It is possible to produce SE with high reaction rate and high quality.

【図面の簡単な説明】[Brief description of the drawings]

【図1】本発明の工程の一例を示すフロー図である。FIG. 1 is a flowchart showing an example of the process of the present invention.

【符号の説明】[Explanation of symbols]

1 反応器 2 充填塔 3 第1凝縮器 4 第2凝縮器 5 第3凝縮器 6 真空系 DESCRIPTION OF SYMBOLS 1 Reactor 2 Packing tower 3 1st condenser 4 2nd condenser 5 3rd condenser 6 Vacuum system

───────────────────────────────────────────────────── フロントページの続き (72)発明者 高橋 壽龍 三重県四日市市東邦町1番地 三菱化成 株式会社四日市工場内 (72)発明者 加曽利 行雄 三重県四日市市東邦町1番地 三菱化成 株式会社四日市工場内 ──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor, Jusyu Takahashi 1, Tohocho, Yokkaichi, Mie Prefecture Inside the Mitsubishi Kasei Yokkaichi Plant (72) Inventor, Yukio Kasori 1, Tohocho, Yokkaichi, Mie Prefecture Mitsubishi Kasei, Yokkaichi in the factory

Claims (5)

(57)【特許請求の範囲】(57) [Claims] 【請求項1】 アルカリ触媒の存在下、ジメチルスルホ
キシドを反応溶媒として、ショ糖と脂肪酸アルキルエス
テルとのエステル交換反応によりショ糖脂肪酸エステル
を製造する方法において、充填塔と複数個の凝縮器とを
直列に配置した反応器を使用し、且つ第1段凝縮器の凝
縮液を充填塔の塔頂に還流することを特徴とするショ糖
脂肪酸エステルの製造方法。
1. A method for producing a sucrose fatty acid ester by a transesterification reaction between sucrose and a fatty acid alkyl ester using dimethyl sulfoxide as a reaction solvent in the presence of an alkali catalyst. A method for producing a sucrose fatty acid ester, comprising using a reactor arranged in series and refluxing a condensate of a first-stage condenser to the top of a packed column.
【請求項2】 脂肪酸アルキルエステルとして脂肪酸メ
チルを使用し、第1段凝縮器を40〜70℃、第2段凝
縮器を−5〜30℃に制御することを特徴とする請求項
1の製造方法。
2. The method according to claim 1, wherein fatty acid methyl is used as the fatty acid alkyl ester, and the first stage condenser is controlled at 40 to 70 ° C. and the second stage condenser is controlled at -5 to 30 ° C. Method.
【請求項3】 −10℃以下に制御された第3段凝縮器
を介して真空系が接続された反応器を使用することを特
徴とする請求項2の製造方法。
3. The method according to claim 2, wherein a reactor is connected to a vacuum system via a third-stage condenser controlled at -10 ° C. or lower.
【請求項4】 第2段凝縮器の凝縮液を反応系外に除去
することを特徴とする請求項1の製造方法。
4. The method according to claim 1, wherein the condensate in the second-stage condenser is removed outside the reaction system.
【請求項5】 第2段凝縮器の凝縮液と第3段凝縮器の
凝縮液を合わせて反応系外に除去することを特徴とする
請求項1の製造方法。
5. The method according to claim 1, wherein the condensate from the second-stage condenser and the condensate from the third-stage condenser are removed together outside the reaction system.
JP4242306A 1992-09-10 1992-09-10 Method for producing sucrose fatty acid ester Expired - Fee Related JP2630182B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP4242306A JP2630182B2 (en) 1992-09-10 1992-09-10 Method for producing sucrose fatty acid ester

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP4242306A JP2630182B2 (en) 1992-09-10 1992-09-10 Method for producing sucrose fatty acid ester

Publications (2)

Publication Number Publication Date
JPH06122694A JPH06122694A (en) 1994-05-06
JP2630182B2 true JP2630182B2 (en) 1997-07-16

Family

ID=17087266

Family Applications (1)

Application Number Title Priority Date Filing Date
JP4242306A Expired - Fee Related JP2630182B2 (en) 1992-09-10 1992-09-10 Method for producing sucrose fatty acid ester

Country Status (1)

Country Link
JP (1) JP2630182B2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69428502T2 (en) * 1993-12-24 2002-05-23 Mitsubishi Chemical Corp., Tokio/Tokyo Process for the preparation of sucrose fatty acid esters
KR100443078B1 (en) * 2002-04-16 2004-08-02 (주)코아켐 Producing method of sugar fatty acid ester
US11518778B2 (en) 2018-08-10 2022-12-06 Tohoku University Method for producing sugar fatty acid ester by transesterification reaction

Also Published As

Publication number Publication date
JPH06122694A (en) 1994-05-06

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