JPH04321697A - Purification of sucrose fatty acid ester - Google Patents
Purification of sucrose fatty acid esterInfo
- Publication number
- JPH04321697A JPH04321697A JP282091A JP282091A JPH04321697A JP H04321697 A JPH04321697 A JP H04321697A JP 282091 A JP282091 A JP 282091A JP 282091 A JP282091 A JP 282091A JP H04321697 A JPH04321697 A JP H04321697A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- ester
- sucrose fatty
- sucrose
- acid ester
- 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.)
- Granted
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 63
- 239000000194 fatty acid Substances 0.000 title claims abstract description 63
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 63
- -1 sucrose fatty acid ester Chemical class 0.000 title claims abstract description 63
- 229930006000 Sucrose Natural products 0.000 title claims abstract description 43
- 239000005720 sucrose Substances 0.000 title claims abstract description 43
- 238000000746 purification Methods 0.000 title description 2
- 238000000199 molecular distillation Methods 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 238000006467 substitution reaction Methods 0.000 claims abstract description 7
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 abstract description 6
- 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 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000593 microemulsion method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明はショ糖脂肪酸エステルの
精製方法に関する。詳しくは、ショ糖脂肪酸エステルの
精製において、脂肪酸アルコールエステルを除去するシ
ョ糖脂肪酸エステルの精製方法に関する。FIELD OF THE INVENTION The present invention relates to a method for purifying sucrose fatty acid esters. Specifically, the present invention relates to a method for purifying sucrose fatty acid ester, which removes fatty acid alcohol ester in purifying sucrose fatty acid ester.
【０００２】0002
【従来の技術】ショ糖脂肪酸エステルの合成法には種々
の方法があるが、いずれの合成反応で得られた粗エステ
ル中にも、目的のショ糖脂肪酸エステルの他、過剰の原
料脂肪酸アルコールエステル及び石けんが含まれるため
、これらの夾雑物を除去する操作が必要である。[Prior Art] There are various methods for synthesizing sucrose fatty acid esters, but in any of the crude esters obtained by the synthesis reaction, in addition to the target sucrose fatty acid ester, there is an excess of raw fatty acid alcohol ester. and soap, so it is necessary to remove these impurities.
【０００３】石けんは、通常、水又は少量のアルコール
を含んだ水を用いて、粗エステルから抽出して比較的容
易に除去することが可能である。しかし、未反応の脂肪
酸アルコールエステルは、水によって抽出されないので
除くことが難しい。Soap can be relatively easily removed by extraction from the crude ester, usually using water or water containing a small amount of alcohol. However, unreacted fatty acid alcohol esters are difficult to remove because they are not extracted by water.
【０００４】従来知られている方法としては、特公平２
−９０３６による分子蒸留処理方法がある。該方法では
、温度を１５０℃以上に上げるとショ糖エステルの分解
が進み、精製物は褐色ないし濃赤色に着色するので好ま
しくないとして、分子蒸留処理温度を６０〜１５０℃、
好ましくは、１２０℃以下で実施するとしている。
しかし、該方法では処理温度が低いため、ショ糖エステ
ルの分解が起こりにくいとしても、一方では低い処理温
度のために単位時間当りの分子蒸留処理量が極めて少な
い量に制限されることとなり、また、脂肪酸炭素数の長
い脂肪酸アルコールエステルの除去が難しいなどの問題
点を抱えている。[0004] As a conventionally known method, there is
There is a molecular distillation treatment method using -9036. In this method, the molecular distillation treatment temperature is set at 60 to 150°C, since raising the temperature to 150°C or higher causes the decomposition of the sucrose ester to proceed and the purified product is colored brown to dark red, which is undesirable.
Preferably, it is carried out at 120°C or lower. However, since the processing temperature is low in this method, even though decomposition of sucrose ester is unlikely to occur, the low processing temperature limits the amount of molecular distillation processed per unit time to an extremely small amount. , there are problems such as difficulty in removing fatty acid alcohol esters that have a long fatty acid carbon number.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、ショ糖脂肪
酸エステル反応物中に残存する原料脂肪酸アルコールエ
ステルを分子蒸留処理法で除去し、高純度のショ糖脂肪
酸エステルを工業的有利に製造する方法を提供するもの
である。[Problems to be Solved by the Invention] The present invention removes the raw fatty acid alcohol ester remaining in the sucrose fatty acid ester reaction product by a molecular distillation process to produce highly pure sucrose fatty acid ester with industrial advantage. The present invention provides a method.
【０００６】[0006]
【課題を解決するための手段】本発明者等は前述の問題
点を解決するため鋭意検討した結果、従来は分解のため
不適当とされていた１６０℃以上のような高い温度の下
でもあらかじめ脂肪酸アルコールエステルの含有量を０
．１〜１０重量という低レベルに調節しておき、短時間
での分子蒸留処理を行えばショ糖脂肪酸エステルの精製
が可能であり、かつ多量処理が可能であり、効率的であ
ることを見い出し、本発明に到達した。[Means for Solving the Problems] As a result of intensive studies in order to solve the above-mentioned problems, the present inventors have developed a method that can be used in advance even at high temperatures of 160°C or higher, which were conventionally considered inappropriate due to decomposition. Content of fatty acid alcohol ester is 0
．． We discovered that it is possible to purify sucrose fatty acid ester by adjusting it to a low level of 1 to 10 weight and performing a molecular distillation process in a short time, and that it is possible to process a large amount and is efficient. We have arrived at the present invention.
【０００７】即ち、本発明の要旨は、脂肪酸アルコール
エステルの含有量が０．１〜１０重量％のショ糖脂肪酸
エステル反応物を、温度１５５〜２２０℃、仕込み流量
６０〜５００リットル／ｍ２ ・ｈｒの条件下において
、分子蒸留処理し、脂肪酸アルコールエステルを除去す
ることを特徴とするショ糖脂肪酸エステルの精製方法に
存する。That is, the gist of the present invention is to prepare a sucrose fatty acid ester reactant having a fatty acid alcohol ester content of 0.1 to 10% by weight at a temperature of 155 to 220°C and a charging flow rate of 60 to 500 liters/m2/hr. The present invention provides a method for purifying sucrose fatty acid esters, which comprises performing a molecular distillation treatment to remove fatty acid alcohol esters under the following conditions.
【０００８】以下、本発明を詳細に説明する。本発明の
対象とするショ糖脂肪酸エステルは、ショ糖と脂肪酸と
のエステルであり、１分子中の脂肪酸置換数（置換度）
には特定に限定されない。但し、平均置換度が４〜７の
高置換度ショ糖脂肪酸エステルでは、一般に、反応原料
として、より過剰の脂肪酸アルコールエステルが必要と
なることから、該高置換度ショ糖脂肪酸エステルの精製
に本発明は特に有用である。The present invention will be explained in detail below. The sucrose fatty acid ester targeted by the present invention is an ester of sucrose and fatty acid, and the number of fatty acid substitutions in one molecule (degree of substitution)
is not specifically limited to. However, since highly substituted sucrose fatty acid esters with an average degree of substitution of 4 to 7 generally require an excess of fatty acid alcohol ester as a reaction raw material, it is difficult to purify the highly substituted sucrose fatty acid esters. The invention is particularly useful.
【０００９】本発明における脂肪酸アルコールエステル
としては、特に限定はないが、沸点範囲の関係により、
通常、炭素数６〜３０、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
飽和脂肪酸と、通常、炭素数１〜６のアルコール、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。また、かかるアルコ
ールエステルは、２種以上の混合物として用いてもよい
。[0009] The fatty acid alcohol ester in the present invention is not particularly limited, but depending on the boiling point range,
Usually saturated or unsaturated fatty acids having 6 to 30 carbon atoms, preferably 12 to 22 carbon atoms, such as caproic acid, capric acid,
Saturated fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, unsaturated fatty acids such as linoleic acid, oleic acid, linoleic acid, erucic acid, ricinoleic acid, and alcohols having 1 to 6 carbon atoms, Examples include esters with methanol, ethanol, propanol, butanol, and the like. Further, such alcohol esters may be used as a mixture of two or more kinds.
【００１０】本発明において用いるショ糖脂肪酸エステ
ル反応物とは、ショ糖脂肪酸エステルの一般的な合成方
法により反応を行なった後、溶媒、石けん等を除去した
粗ショ糖脂肪酸エステルである。また、該反応物中の脂
肪酸アルコールエステルの含有量は０．１〜１０重量％
の範囲のものが用いられる。脂肪酸アルコールエステル
の含有量がこの範囲を越える場合は、分子蒸留での精製
回数を甚だしく多くする必要があるので本発明では用い
られない。[0010] The sucrose fatty acid ester reaction product used in the present invention is a crude sucrose fatty acid ester obtained by removing solvent, soap, etc. after performing a reaction using a general method for synthesizing sucrose fatty acid ester. In addition, the content of fatty acid alcohol ester in the reaction product is 0.1 to 10% by weight.
Those within the range of are used. If the content of fatty acid alcohol ester exceeds this range, it will not be used in the present invention because it will be necessary to significantly increase the number of times of purification by molecular distillation.
【００１１】ショ糖脂肪酸エステルの合成方法について
は特に限定されないが、好ましくは、溶媒法である。溶
媒法とは、ショ糖と脂肪酸アルコールエステルのいずれ
をも溶解させる溶媒、たとえば、ジメチルスルホキシド
（以下「ＤＭＳＯ」という）、ジメチルホルムアミドな
どを用いて、均一反応させる方法である。該方法は、他
のショ糖脂肪酸エステルの合成法、例えば、無溶媒法、
ミクロエマルジョン法などと比較して、原料の脂肪酸ア
ルコールエステルの量が少なくて済む。従って、特に高
置換度のショ糖脂肪酸エステルを製造する際でも、脂肪
酸アルコールエステルの含有量が０．１〜１０重量％の
エステル反応物を容易に得ることができる。[0011] The method for synthesizing the sucrose fatty acid ester is not particularly limited, but preferably a solvent method is used. The solvent method is a method in which a homogeneous reaction is carried out using a solvent that dissolves both sucrose and fatty acid alcohol ester, such as dimethyl sulfoxide (hereinafter referred to as "DMSO") and dimethyl formamide. The method is similar to other sucrose fatty acid ester synthesis methods, such as a solvent-free method,
Compared to the microemulsion method, the amount of fatty acid alcohol ester used as a raw material is small. Therefore, even when producing a sucrose fatty acid ester with a particularly high degree of substitution, an ester reaction product having a fatty acid alcohol ester content of 0.1 to 10% by weight can be easily obtained.
【００１２】本発明で使用する分子蒸留装置としては、
遠心式と流下膜式のいずれの方法も使用できる。通常１
ｍｍＨｇ以下、好ましくは１０−１〜１０−４ｍｍＨｇ
の減圧下で行なわれる。分子蒸留の温度は、１５５〜２
２０℃である。かかる温度は、通常、仕込液が分子蒸留
装置内で形成する薄膜の近傍に温度センサーを設置する
ことにより精密測定される。また、分子蒸留機への反応
物の仕込み流量は、分子蒸留機の加熱面積に対して６０
〜５００リットル／ｍ２ ・ｈｒ、好ましくは１００〜
４００リットル／ｍ２ ・ｈｒから選択される。分子蒸
留の温度が１５５℃に満たない場合は、上述の仕込み流
量の範囲では、分離効率が著しく低下するので、処理量
が制限されるので好ましくない。一方、２２０℃を越え
るとショ糖脂肪酸エステルの熱分解も無視しえなくなり
不都合である。[0012] The molecular distillation apparatus used in the present invention includes:
Both centrifugal and falling film methods can be used. Usually 1
mmHg or less, preferably 10-1 to 10-4 mmHg
This is done under reduced pressure. The temperature of molecular distillation is 155-2
The temperature is 20°C. Such temperature is usually precisely measured by placing a temperature sensor near the thin film that the feed liquid forms in the molecular distillation apparatus. In addition, the flow rate of reactants to the molecular distillation machine is 60% relative to the heating area of the molecular distillation machine.
~500 liters/m2・hr, preferably 100~
Selected from 400 liters/m2/hr. If the molecular distillation temperature is less than 155° C., the separation efficiency will be significantly lowered within the above-mentioned feed flow rate range, which will limit the throughput, which is not preferable. On the other hand, if the temperature exceeds 220°C, thermal decomposition of the sucrose fatty acid ester cannot be ignored, which is disadvantageous.
【００１３】[0013]
【実施例】以下に実施例をあげて詳述するが、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。[Examples] The present invention will be described in detail with reference to Examples, but the present invention is not limited by these Examples unless the gist thereof is exceeded.
【００１４】参考例 （ショ糖脂肪酸エステルの合成
）十分に乾燥した３０リットル容反応器にショ糖１４０
５ｇとＤＭＳＯを６３４６ｇ仕込み、２３ｍｍＨｇの減
圧下で沸騰させながら溶媒を還流させた。２０分後にＤ
ＭＳＯを留出させ脱水した。留出量が１０００ｇに達し
たところで留出を止め、系内の水分を測定したところ、
残存水分は０．０６重量％であった。次に、無水炭酸カ
リウム６３ｇとステアリン酸メチル６６１５ｇを仕込み
、２３ｍｍＨｇで沸騰させながら、溶媒は還流し、生成
したメタノールは系外に留出させた。Reference Example (Synthesis of sucrose fatty acid ester) 140 liters of sucrose was placed in a sufficiently dry 30 liter reactor.
5 g and 6346 g of DMSO were charged, and the solvent was refluxed while boiling under reduced pressure of 23 mmHg. D after 20 minutes
MSO was distilled off and dehydrated. When the distillation amount reached 1000g, the distillation was stopped and the water content in the system was measured.
The residual moisture was 0.06% by weight. Next, 63 g of anhydrous potassium carbonate and 6615 g of methyl stearate were charged, and the solvent was refluxed while boiling at 23 mmHg, and the generated methanol was distilled out of the system.
【００１５】反応液が実質的に均一になった時点で溶媒
の留去を開始し、温度を１１０℃まで上げ、７ｍｍＨｇ
まで減圧し、一定に保持した。反応開始後、１０時間で
反応を止め、得られた反応液を中和、温水にて洗浄した
ところ、未反応のステアリン酸メチルの含有量は４．２
６重量％、平均置換度（以下「ＥＶ値」と略す）５．３
、色価（以下「ＣＶ値」と略す）０．５の粗ショ糖脂肪
酸エステル７１７０ｇが得られた。なお、ＣＶ値は下式
で定義されるものである。[0015] When the reaction solution became substantially homogeneous, distillation of the solvent was started, and the temperature was raised to 110°C and 7mmHg.
The pressure was reduced to and held constant. The reaction was stopped 10 hours after the start of the reaction, and the resulting reaction solution was neutralized and washed with warm water, and the content of unreacted methyl stearate was 4.2
6% by weight, average degree of substitution (hereinafter abbreviated as "EV value") 5.3
, 7170 g of crude sucrose fatty acid ester with a color value (hereinafter abbreviated as "CV value") of 0.5 was obtained. Note that the CV value is defined by the following formula.
【００１６】[0016]
【数１】[Math 1]
【００１７】ｌ：測定に用いたセルの液層の厚さ（ｃｍ
）ｃ：被検液１ｍｌ中に含まれる試料（ｇ）Ｔ：波長４
２０ｍμでの透過率
製品の着色度（特に黄色味）を表示するために光の波長
４２０ｍμを選定した。色価は低い方が黄色味が少なく
望ましい。l: Thickness of the liquid layer of the cell used for measurement (cm
) c: Sample contained in 1 ml of test liquid (g) T: Wavelength 4
Transmittance at 20 mμ A light wavelength of 420 mμ was selected to indicate the degree of coloration (especially yellowishness) of the product. The lower the color value, the less yellowish, which is desirable.
【００１８】実施例１
参考例の方法で製造した粗ショ糖ステアリル酸エステル
２０ｋｇを日本車輌製造株式会社製の遠心式分子蒸留処
理装置（ＭＳ−３８０型）に仕込んだ。温度１００℃、
仕込み流量２６５リットル／ｍ２ ・ｈｒおよび１０−
１ｍｍＨｇの減圧下で脱気操作を行った後、温度１６５
℃、仕込み流量１９５リットル／ｍ２ ・ｈｒおよび１
０−３ｍｍＨｇの減圧下で第１回目の分子蒸留処理を行
った。Example 1 20 kg of crude sucrose stearyl ester produced by the method of Reference Example was charged into a centrifugal molecular distillation apparatus (Model MS-380) manufactured by Nippon Sharyo Manufacturing Co., Ltd. Temperature 100℃,
Feeding flow rate 265 liters/m2 ・hr and 10-
After degassing under a reduced pressure of 1 mmHg, the temperature was reduced to 165
°C, charging flow rate 195 liters/m2 ・hr and 1
The first molecular distillation treatment was performed under reduced pressure of 0-3 mmHg.
【００１９】次に、第１回目の分子蒸留処理品を使用し
て第２回目の分子蒸留処理を温度１７０℃、仕込み流量
２６５リットル／ｍ２ ・ｈｒおよび１０−３ｍｍＨｇ
の条件で行った。第３回目の分子蒸留処理は第２回目の
分子蒸留処理品を使用して温度１８０℃、仕込み流量２
６５リットル／ｍ２ ・ｈｒおよび１０−３ｍｍＨｇの
条件で行った。以上の結果を表１に示す。ＣＶ値および
ＥＶ値とも特に変化は認められなかった。Next, using the first molecular distillation product, a second molecular distillation treatment is performed at a temperature of 170°C, a feed flow rate of 265 liters/m2·hr, and 10-3 mmHg.
It was conducted under the following conditions. The third molecular distillation treatment uses the second molecular distillation treated product at a temperature of 180°C and a feed flow rate of 2.
The test was carried out under the conditions of 65 liters/m2·hr and 10-3 mmHg. The above results are shown in Table 1. No particular changes were observed in either the CV value or the EV value.
【００２０】実施例２〜７
原料脂肪酸メチルエステルの種類及び仕込み量を変えた
以外は、参考例と同様な方法で各種のショ糖脂肪酸エス
テルを合成した。これらについて、実施例１に準じた方
法で分子蒸留処理（圧力はいずれも１０−３ｍｍＨｇ）
を行った結果を表１および表２に示す。Examples 2 to 7 Various sucrose fatty acid esters were synthesized in the same manner as in Reference Example except that the type and amount of raw fatty acid methyl ester were changed. These were treated with molecular distillation in the same manner as in Example 1 (pressure was 10-3 mmHg in both cases).
The results are shown in Tables 1 and 2.
【００２１】実施例８、比較例１〜２
参考例の方法に準じて製造した粗ショ糖ステアリル酸エ
ステルを、圧力１０−３ｍｍＨｇ、仕込み流量１５０リ
ットル／ｍ２ ・ｈｒとし、温度を各々１８０℃、１４
０℃、１２０℃に設定して分子蒸留処理を２回行った結
果を表３に示す。Example 8, Comparative Examples 1 and 2 Crude sucrose stearyl ester produced according to the method of the reference example was prepared at a pressure of 10-3 mmHg, a charging flow rate of 150 liters/m2/hr, and a temperature of 180°C and 180°C, respectively. 14
Table 3 shows the results of performing molecular distillation twice at temperatures of 0°C and 120°C.
【００２２】[0022]
【表１】[Table 1]
【００２３】[0023]
【表２】[Table 2]
【００２４】[0024]
【表３】[Table 3]
【００２５】[0025]
【発明の効果】本発明の方法によれば、ショ糖脂肪酸エ
ステル中に残存する脂肪酸アルコールエステルを効率よ
く分離・除去することができるので、極めて高純度のシ
ョ糖脂肪酸エステルを経済的に製造することができる。[Effects of the Invention] According to the method of the present invention, the fatty acid alcohol ester remaining in the sucrose fatty acid ester can be efficiently separated and removed, so that extremely pure sucrose fatty acid ester can be economically produced. be able to.
Claims (4)
０．１〜１０重量％のショ糖脂肪酸エステル反応物を、
温度１５５〜２２０℃、仕込み流量６０〜５００リット
ル／ｍ２ ・ｈｒの条件下において分子蒸留処理し、脂
肪酸アルコールエステルを除去することを特徴とするシ
ョ糖脂肪酸エステルの精製方法。Claim 1: A sucrose fatty acid ester reaction product having a fatty acid alcohol ester content of 0.1 to 10% by weight,
A method for purifying sucrose fatty acid ester, which comprises removing fatty acid alcohol ester by molecular distillation under conditions of a temperature of 155 to 220°C and a feed flow rate of 60 to 500 liters/m2/hr.
法で製造されたものである請求項１記載の方法。2. The method according to claim 1, wherein the sucrose fatty acid ester reaction product is produced by a solvent method.
のショ糖脂肪酸エステルである請求項１記載の方法。[Claim 3] The sucrose fatty acid ester has a degree of substitution of 4 to 7.
The method according to claim 1, wherein the sucrose fatty acid ester is a sucrose fatty acid ester.
脂肪酸の炭素数が１２〜２２である請求項１記載の方法
。4. The method according to claim 1, wherein the fatty acid constituting the fatty acid alcohol ester has 12 to 22 carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP282091A JP2694775B2 (en) | 1991-01-14 | 1991-01-14 | Purification method of sucrose fatty acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP282091A JP2694775B2 (en) | 1991-01-14 | 1991-01-14 | Purification method of sucrose fatty acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04321697A true JPH04321697A (en) | 1992-11-11 |
| JP2694775B2 JP2694775B2 (en) | 1997-12-24 |
Family
ID=11540053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP282091A Expired - Fee Related JP2694775B2 (en) | 1991-01-14 | 1991-01-14 | Purification method of sucrose fatty acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2694775B2 (en) |
-
1991
- 1991-01-14 JP JP282091A patent/JP2694775B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2694775B2 (en) | 1997-12-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4954621A (en) | Process for producing sucrose fatty acid polyester | |
| JPS6115893A (en) | Purification of sucrose fatty acid ester | |
| EP2139844B1 (en) | CONVERSION OF TEREPHTHALIC ACID TO DI-n-BUTYL TEREPHTHALATE | |
| JPH01246243A (en) | Production of alkylglyconate | |
| JP2956504B2 (en) | Method for producing sucrose fatty acid ester | |
| JP4238300B2 (en) | Method for producing high purity bis-β-hydroxyethyl terephthalate | |
| EP1770082B1 (en) | Process for producing sorbitan fatty acid ester | |
| CA1304402C (en) | Process for the purification of 2-hydroxynaphthalene-6-carboxylic acid | |
| JPH04321697A (en) | Purification of sucrose fatty acid ester | |
| JPH07118285A (en) | Production of sucrose fatty acid ester | |
| CN112739675A (en) | Method for recovering high-quality 3-methyl-but-3-en-1-ol | |
| KR100257052B1 (en) | Process for the preparation of 4-amino-1,2,4-triazoles | |
| RU1836348C (en) | Method for obtaining higher alkyl ethers of (4-amino-3,5-dichloro-6-fluoro-2-pyridinyloxy) acetic acid | |
| US3259662A (en) | Purification of trimethylolpropane | |
| KR101688859B1 (en) | Anhydrosugar alcohol ester with improved color and method for preparing the same | |
| US4970336A (en) | Method of purifying α-substituted acetic acids | |
| JPH0390080A (en) | Method for preparation of pure guanine improved in coloration | |
| JPH0478637B2 (en) | ||
| US4760177A (en) | Process for preparing alkali metal salts of trifluoroacetic acid in the anhydrous and crystalline state | |
| US2495440A (en) | Dichloroacetic acid purification | |
| JPH07206889A (en) | Production of sucrose fatty acid ester | |
| JPH08176044A (en) | Production of 2-t-butylhydroquinone | |
| JPH01313491A (en) | Production of sucrose fatty acid polyester with low color value | |
| JP2711887B2 (en) | Method for producing sucrose unsaturated fatty acid ester | |
| JP3312811B2 (en) | Method for purifying trans-1,4-cyclohexanedimethanol dialkyl sulfonate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20070912 Year of fee payment: 10 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080912 Year of fee payment: 11 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080912 Year of fee payment: 11 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090912 Year of fee payment: 12 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090912 Year of fee payment: 12 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100912 Year of fee payment: 13 |
|
| LAPS | Cancellation because of no payment of annual fees |