JPH03184988A - Fractional recovery of saccharide mono-, di-and tri-fatty acid ester - Google Patents
Fractional recovery of saccharide mono-, di-and tri-fatty acid esterInfo
- Publication number
- JPH03184988A JPH03184988A JP32305589A JP32305589A JPH03184988A JP H03184988 A JPH03184988 A JP H03184988A JP 32305589 A JP32305589 A JP 32305589A JP 32305589 A JP32305589 A JP 32305589A JP H03184988 A JPH03184988 A JP H03184988A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- sugar
- acid ester
- hexane
- eluent
- 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
- 239000000194 fatty acid Substances 0.000 title claims abstract description 59
- 238000011084 recovery Methods 0.000 title description 2
- 150000001720 carbohydrates Chemical class 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 51
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 37
- 150000002148 esters Chemical class 0.000 claims abstract description 37
- 229930195729 fatty acid Natural products 0.000 claims abstract description 37
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 27
- -1 hexose fatty acid ester Chemical class 0.000 claims abstract description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 15
- 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 12
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 12
- 150000002402 hexoses Chemical class 0.000 claims abstract description 5
- 235000000346 sugar Nutrition 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 34
- 239000003480 eluent Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 230000009967 tasteless effect Effects 0.000 claims description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 239000012043 crude product Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- 239000006185 dispersion Substances 0.000 claims 1
- 125000005313 fatty acid group Chemical group 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 abstract description 12
- 239000003995 emulsifying agent Substances 0.000 abstract description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
- 239000008103 glucose Substances 0.000 description 8
- 235000019658 bitter taste Nutrition 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003463 adsorbent Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000001983 dialkylethers Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000004088 foaming agent Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000019640 taste Nutrition 0.000 description 2
- 229940034610 toothpaste Drugs 0.000 description 2
- 239000000606 toothpaste Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000003084 food emulsifier Nutrition 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は糖脂肪酸エステルの製造において、反応粗生成
物より糖モノ−、ジ−及びトリ−脂肪酸エステルを分別
回収する方法に関し、特に実質的に無味の糖モノ−及び
ジ−脂肪酸エステルを分別回収する方法に関する。Detailed Description of the Invention [Industrial Application Field] The present invention relates to a method for fractionating and recovering sugar mono-, di-, and tri-fatty acid esters from a crude reaction product in the production of sugar-fatty acid esters, and particularly relates to a method for fractionating and recovering sugar mono-, di-, and tri-fatty acid esters from a crude reaction product in the production of sugar-fatty acid esters. The present invention relates to a method for separately recovering tasteless sugar mono- and di-fatty acid esters.
従来、六炭糖の脂肪酸エステルは、糖をピリジン溶媒中
で脂肪酸クロライド又は脂肪酸無水物と反応させること
によって合成されている。たＳ′この方法では、反応生
成物は糖のモノ−、ジ−、トリ及びテトラ−脂肪酸エス
テルの混合物として得られ、モノ−あるいはジ−脂肪酸
エステルのみを主成分とする反応生成物を得ることはで
きない。Traditionally, fatty acid esters of hexoses have been synthesized by reacting sugars with fatty acid chlorides or fatty acid anhydrides in pyridine solvent. In this method, the reaction product is obtained as a mixture of mono-, di-, tri- and tetra-fatty acid esters of sugars, and it is possible to obtain a reaction product containing only mono- or di-fatty acid esters as the main component. I can't.
しかも、上記反応生成物について、ジアルキルエーテル
、酢酸エチル、アセトン、エタノール等の溶媒を用いて
、再結晶法により精製を行なっても、糖のモノ−、ジ−
及びトリ−脂肪酸エステルの分別は困難であった。その
上、このようにして得られた再結晶品でも、苦み等の不
快感があり、歯磨発泡剤、食品乳化剤としては不適当で
ある。Moreover, even if the above reaction product is purified by recrystallization using a solvent such as dialkyl ether, ethyl acetate, acetone, or ethanol, the sugar mono- and di-
It was difficult to separate tri-fatty acid esters. Moreover, even the recrystallized product obtained in this way has an unpleasant taste such as bitterness and is unsuitable as a toothpaste foaming agent or a food emulsifier.
糖のモノ脂肪酸エステルとジ脂肪酸エステル等のポリ脂
肪酸エステルとを効率的に分離するために、メタノール
、アセトン等の含水溶媒を用いる方法が提案されている
（特公昭３８−６１６５号公報）。In order to efficiently separate monofatty acid esters of sugars from polyfatty acid esters such as difatty acid esters, a method using a water-containing solvent such as methanol or acetone has been proposed (Japanese Patent Publication No. 38-6165).
ところが、この方法はモノエステルの収率が低く（５３
％以下）、また反応粗生成物のモノエステルの純度が低
い場合、精製して得られるモノエステルの純度が低下す
るなどという欠点を有する。However, this method has a low yield of monoester (53
% or less), and if the purity of the monoester of the reaction crude product is low, there is a drawback that the purity of the monoester obtained by purification decreases.
従って、本発明の目的は、糖脂肪酸エステル反応粗生成
物から糖モノ−、ジ−及びトリ−脂肪酸エステルを高収
率で選択的に分別し、しかも実質的に無味の糖モノ−及
びジ−脂肪酸エステルを９０％以上の高純度で得る方法
を提供することにある。Therefore, an object of the present invention is to selectively separate sugar mono-, di-, and tri-fatty acid esters from a crude product of sugar-fatty acid ester reaction in high yield, and to selectively separate sugar mono-, di-, and tri-fatty acid esters from a crude product of sugar-fatty acid ester reaction, and to provide substantially tasteless sugar mono- and di-fatty acid esters. The object of the present invention is to provide a method for obtaining fatty acid esters with a high purity of 90% or more.
−
〔課題を解決するための手段〕
本発明によれば、六炭糖と脂肪酸又は脂肪酸誘導体との
反応によって得られた六炭糖脂肪酸エステル反応粗生成
物を、ｎ−ヘキサンを満したシリカゲル充填カラムの上
部に供給、分散させた後、下記４種類の溶離液をその順
に流下させ、糖トリ−、ジ−及びモノ−脂肪酸エステル
の夫々を分別回収することを特徴とする糖モノ−、ジ−
及び−トリ−脂肪酸エステルの分別回収方法が提供され
る。- [Means for Solving the Problem] According to the present invention, a hexose fatty acid ester reaction crude product obtained by the reaction of a hexose with a fatty acid or a fatty acid derivative is filled with silica gel filled with n-hexane. After being supplied to the upper part of the column and dispersed, the following four types of eluents are allowed to flow down in that order to separately recover sugar tri-, di-, and mono-fatty acid esters. −
and -tri-fatty acid ester fractional recovery method is provided.
（ｉ）ジエチルエーテルＩｎ−ヘキサン１／３（Ｖ／Ｖ
）ｍ離液（ｉｉ）ジエチルエーテル／ｎ−ヘキサン１／
１（Ｖ／Ｖ）溶離液（昂）ジエチルエーテル溶離液
（ｉｖ）メタノール／エチルエーテル１／９（Ｖ／Ｖ）
溶離液また、本発明によれば、上記方法で得られた糖モ
ノ脂肪酸エステルをジアルキルエーテル、アセトン及び
酢酸エチルから選ばれた少くとも１種の溶媒に分散させ
た後、不溶物を濾別し、減圧乾燥することを特徴とする
糖の６位に脂肪酸が結合した実質的に無味の糖モノ脂肪
酸エステルの分別回収方法が提供される。(i) Diethyl ether In-hexane 1/3 (V/V
) m syneresis (ii) diethyl ether/n-hexane 1/
1 (V/V) Eluent (Kyo) Diethyl ether Eluent (iv) Methanol/Ethyl ether 1/9 (V/V)
Eluent According to the present invention, the sugar monofatty acid ester obtained by the above method is dispersed in at least one solvent selected from dialkyl ether, acetone, and ethyl acetate, and then insoluble matter is filtered off. Provided is a method for fractionating and recovering a substantially tasteless sugar monofatty acid ester in which a fatty acid is bonded to the 6-position of the sugar, which is characterized by drying under reduced pressure.
４−
即ち、本発明は糖脂肪酸エステル反応粗生成物中の糖モ
ノ−、ジ−及びトリ−脂肪酸エステル各成分を分別する
のに、各成分のシリカゲル吸着剤に対する親和性の差を
利用するものであり、そのことによって各成分を選択的
に９０％以上の高純度で分別回収することができ、しか
も実質的に無味の糖ジ脂肪酸エステルを得ることができ
る。また、本発明で得られた糖モノ脂肪酸エステルにつ
いては、糖の６位に脂肪酸が結合した実質的に無味の糖
モノ脂肪酸エステルと糖の１〜４位に脂肪酸が結合した
有隙の糖モノ脂肪酸エステルとの、有機溶媒に対する溶
解度差を利用することによって、実質的に無味の糖モノ
脂肪酸エステルを得ることができる。4- That is, the present invention utilizes the difference in affinity of each component to the silica gel adsorbent to separate the sugar mono-, di-, and tri-fatty acid ester components in the crude sugar-fatty acid ester reaction product. As a result, each component can be selectively separated and recovered with a high purity of 90% or more, and a substantially tasteless sugar difatty acid ester can be obtained. Furthermore, regarding the sugar monofatty acid ester obtained in the present invention, there is a substantially tasteless sugar monofatty acid ester in which a fatty acid is bound to the 6th position of the sugar, and a porous sugar monofatty acid ester in which a fatty acid is bound to the 1st to 4th positions of the sugar. Substantially tasteless sugar monofatty acid esters can be obtained by utilizing the difference in solubility in organic solvents between fatty acid esters and fatty acid esters.
本発明の対象となる糖脂肪酸エステル反応粗生成物の原
料となる糖としては、六炭糖で糖の数が１つのモノヘキ
ソース類、例えばグルコース、ガラクトース、フルクト
ースなどが挙げられる。また、糖脂肪酸エステルを構成
するアシル基は、炭素数Ｃ５＝Ｃｚ＋のアルキル鎖を有
するＣ、、〜Ｃ１Ｚのアシル基である。糖脂肪酸エステ
ル反応粗生成物は、モノヘキソースとＣ６〜Ｃ１Ｚの脂
肪酸、ＣＧ−Ｃ□２の脂肪酸アルキルエステル（アルキ
ル基としてはメチル、エチル、プロピル基等のＣ工〜Ｃ
８のアルキル基）又は０６〜Ｃ１□の脂肪酸ハロゲン化
物とから合成される。Examples of sugars that can be used as raw materials for the sugar fatty acid ester reaction crude product that is the object of the present invention include monohexoses that are hexoses and have one sugar, such as glucose, galactose, and fructose. Further, the acyl group constituting the sugar fatty acid ester is an acyl group of C, . . . -C1Z having an alkyl chain with carbon number C5=Cz+. The crude sugar fatty acid ester reaction product consists of monohexose, C6 to C1Z fatty acids, and CG-C□2 fatty acid alkyl esters (alkyl groups include C to C such as methyl, ethyl, and propyl groups).
8 alkyl group) or a fatty acid halide of 06 to C1□.
合成方法は、リパーゼなどの酵素を用いる方法や酸、ア
ルカリ土類金属系触媒を用いる純化学合成的方法などを
採用することができる。As the synthesis method, a method using an enzyme such as lipase, a pure chemical synthesis method using an acid or an alkaline earth metal catalyst, etc. can be adopted.
本発明においては、前記糖脂肪酸エステル反応粗生成物
から、糖モノ−、ジ−及びトリ−脂肪酸エステルの各成
分を分別するのに、該反応粗生成物をｎ−ヘキサンを満
したシリカゲル充填カラムの上部に供給、分散させた後
、上記各成分のシリカゲル吸着剤に対する親和性の差を
利用して、メタノール／ジエチルエーテル／ｎ−ヘキサ
ンの比率を変えた少くとも４種類、好ましくは５種類の
溶離液を、極性の低いもの順に流下させることによって
行なう。In the present invention, in order to separate each component of sugar mono-, di- and tri-fatty acid esters from the crude sugar fatty acid ester reaction product, the crude reaction product is passed through a silica gel packed column filled with n-hexane. At least four types, preferably five types, of methanol/diethyl ether/n-hexane with different ratios are supplied and dispersed in the upper part of the silica gel adsorbent by utilizing the difference in affinity of each component to the silica gel adsorbent. This is done by flowing the eluents in descending order of polarity.
本発明の実施に当っては、先ず分離カラムが調製される
。前記反応粗生成物１重量部に対し、該カラムは３０−
４３０−４Ｏ０、好ましくは７０−２７０−２３Ｏのシ
リカゲルの例えば１０重量部を、ｎ−ヘキサンを用いて
内径×長さの比がｌＸ５〜１×２０のカラムに充填し、
充分に脱泡することによって調製される。In carrying out the present invention, first a separation column is prepared. For 1 part by weight of the reaction crude product, the column contains 30-
For example, 10 parts by weight of 430-4O0, preferably 70-270-23O silica gel is packed into a column with an inner diameter x length ratio of 1 x 5 to 1 x 20 using n-hexane,
Prepared by thorough defoaming.
続いて、前記の反応粗生成物を上記のシリカゲル充填カ
ラムの上部に供給、分散させた後、以下の４種類（好ま
しくは５種類）の溶離液を下記の順序で流下させる。Subsequently, the reaction crude product is supplied and dispersed in the upper part of the silica gel-packed column, and then the following four (preferably five) types of eluents are allowed to flow down in the following order.
（ｉ）先ず、ジエチルエーテル／ｎ−ヘキサンｌ／３（
Ｖ／Ｖ）溶離液の例えば１００容量部をカラムに流下さ
せることにより、糖のテトラ−以上のポリー脂肪酸エス
テルを主溶出成分とする溶出液が得られる。なお、該溶
離液の流下前に、ジエチルエーテル／ｎ−ヘキサンｌ／
９ （Ｖ／Ｖ）溶離液の例えば１００容量部を流下させ
ると、炭化水素、脂肪酸等の油分が除去される外、テト
ラ脂肪酸エステルを主溶出成分とする溶出液が得られる
ので、糖のテトラ以上のポリ脂肪酸エステル成分を利用
する場合には、この予備溶離液処理を行なうことが好ま
しい。(i) First, diethyl ether/n-hexane l/3 (
V/V) By flowing, for example, 100 parts by volume of the eluent through the column, an eluate containing tetra- or higher polyfatty acid ester of sugar as the main eluate component can be obtained. In addition, before flowing down the eluent, diethyl ether/n-hexane l/
9 (V/V) When, for example, 100 parts by volume of the eluent is allowed to flow down, oil components such as hydrocarbons and fatty acids are removed, and an eluate containing tetra fatty acid ester as the main eluate component is obtained. When using the above polyfatty acid ester component, it is preferable to carry out this preliminary eluent treatment.
′（ｉｉ）次に、ジエチルエーテル／ｎ−ヘキサン１／
１ （Ｖ／Ｖ）溶離液の例えば１５０容量部をカラムに
流下させることにより、糖のトリ脂肪酸エステルを主溶
出成分とする溶出液が得られる。'(ii) Next, diethyl ether/n-hexane 1/
By flowing, for example, 150 parts by volume of the 1 (V/V) eluent down the column, an eluate containing trifatty acid ester of sugar as the main eluate component is obtained.
（石）Ｍいて、ジエチルエーテル溶離液の例えば２００
容量部をカラムに流下させると、糖のジ脂肪酸エステル
を主溶出成分とする溶出液が得られる。(Stone)M, for example 200% of diethyl ether eluent
When a volumetric portion is allowed to flow down the column, an eluate containing sugar difatty acid ester as the main eluate component is obtained.
（ｉｖ ）更に続いて、メタノール／ジエチルエーテル
ｌ／９ （Ｖ／Ｖ）溶離液の例えば２００容量部をカラ
ムに流下させると、糖のモノ脂肪酸エステルを主成分と
する溶出液が得られる。(iv) Subsequently, for example, 200 parts by volume of the methanol/diethyl ether l/9 (V/V) eluent is allowed to flow down the column to obtain an eluate whose main component is monofatty acid ester of sugar.
なお、分画処理における反応粗生成物供給量と溶離液と
の供給量の比率は、ｌ／１０〜１／２０００（重量／容
量）の範囲で行なうことが好ましく、反応粗生成物供給
量とシリカゲルとの比率は、１１５〜１／１００の範囲
で行なうことが好ましい。また、溶出する場合のカラム
温度は、反応粗生成物の溶媒への溶解性の面から、１５
〜３５℃の範囲とするのが好ましい。In addition, the ratio of the reaction crude product supply amount and the eluent supply amount in the fractionation treatment is preferably in the range of 1/10 to 1/2000 (weight/volume), and the reaction crude product supply amount and The ratio with silica gel is preferably in the range of 115 to 1/100. In addition, the column temperature for elution is 15
It is preferable to set it as the range of -35 degreeC.
得られた各溶出液から溶媒を減圧留去した後、乾燥する
ことにより、前記各成分を９０％以上の純度で得ること
ができる。しかも、この分画方法によって得られた糖ジ
脂肪酸エステルは、実質的に無味である。By distilling off the solvent from each of the obtained eluates under reduced pressure and then drying them, each of the above-mentioned components can be obtained with a purity of 90% or more. Furthermore, the sugar difatty acid ester obtained by this fractionation method is substantially tasteless.
たゾ、得られた糖モノ脂肪酸エステルは苦みを有する。However, the obtained sugar monofatty acid ester has a bitter taste.
しかし、この糖モノ脂肪酸エステルからは、有機溶媒に
対する溶解度差を利用することによって、糖の６位に脂
肪酸が結合した、実質的に無味の糖モノ脂肪酸エステル
を分画することができる。However, from this sugar monofatty acid ester, a substantially tasteless sugar monofatty acid ester in which a fatty acid is bonded to the 6-position of the sugar can be fractionated by utilizing the difference in solubility in organic solvents.
即ち、前記の糖モノ脂肪酸エステルを、ジアルキルエー
テル、アセトン及び酢酸エチルから選ばれた少くとも１
種の溶媒に分散後、不溶分を濾別してから減圧乾燥する
ことにより、糖の６位にアシル基が結合した糖モノ脂肪
酸エステルを得ることができ、しかもこのようにして得
られた糖モノ脂肪酸エステルは実質的に無味である。こ
の場合、糖の１〜４位に脂肪酸が結合したモノ脂肪酸エ
ステルは、前記溶媒に対する溶解度が大きく、溶解成分
として得られ、この成分は苦みを有している。That is, the sugar monofatty acid ester is combined with at least one selected from dialkyl ether, acetone, and ethyl acetate.
After dispersing the seeds in a solvent, filtering off the insoluble matter and drying under reduced pressure, it is possible to obtain a sugar monofatty acid ester in which an acyl group is bonded to the 6-position of the sugar. Esters are virtually tasteless. In this case, the monofatty acid ester in which fatty acids are bonded to the 1st to 4th positions of the sugar has high solubility in the solvent and is obtained as a dissolved component, which has a bitter taste.
本発明の方法は、糖脂肪酸エステル反応粗生成物中の糖
のモノ−、ジ−、トリ−及びテトラ−脂肪酸エステル各
成分のシリカゲル吸着剤に対する親和性の差を利用した
ことから、本発明の方法によると、上記各成分を９０％
以上の純度で分画することができ、しかも実質的に無味
の糖ジ脂肪酸エステルを得ることができる。The method of the present invention utilizes the difference in affinity for the silica gel adsorbent of the mono-, di-, tri-, and tetra-fatty acid ester components of sugar in the crude sugar fatty acid ester reaction product. According to the method, each of the above ingredients is 90%
It is possible to fractionate with a purity higher than that, and to obtain a substantially tasteless sugar difatty acid ester.
また、本発明の方法によって得られた糖モノ脂肪酸エス
テルからは、その６位置換体と１〜４位置換体との特定
溶媒に対する溶解度の差を利用することにより、糖の６
位に脂肪酸が結合した、実質的に無味の糖モノ脂肪酸エ
ステルを得ることができる。In addition, from the sugar monofatty acid ester obtained by the method of the present invention, by utilizing the difference in solubility in a specific solvent between the 6-substituted product and the 1-4-substituted product, it is possible to
It is possible to obtain a substantially tasteless sugar monofatty acid ester in which a fatty acid is bonded to the position.
従って、本発明の方法に従うと、糖脂肪酸エステル反応
粗生成物より、実質的に無味で且っ起泡力、乳化力に優
れた、安全性の高い非イオン活性剤が得られる。この非
イオン活性剤は、糖に対するアルキル基数によって、歯
磨用発泡剤、食品用乳化剤あるいは食品用洗浄剤として
、味が関与する分野での利用に好適なものである。Therefore, according to the method of the present invention, a highly safe nonionic active agent that is substantially tasteless, has excellent foaming power and emulsifying power, and is obtained from the sugar fatty acid ester reaction crude product. Depending on the number of alkyl groups relative to sugar, this nonionic surfactant is suitable for use in fields where taste is involved, such as as a foaming agent for toothpaste, an emulsifier for food, or a detergent for food.
以下、本発明を実施例によって更に詳述するが、本発明
はこれによって限定されるものではない。EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.
実施例１
グルコース１当量に対し直鎖Ｃ□。の脂肪酸クロライド
ｌ当量を、ピリジン溶媒中、反応温度６０℃で３０分間
反応させ、グルコース脂肪酸エステル粗生成物を得た。Example 1 Straight chain C□ per equivalent of glucose. 1 equivalent of fatty acid chloride was reacted in a pyridine solvent at a reaction temperature of 60° C. for 30 minutes to obtain a glucose fatty acid ester crude product.
次に、この粗生成物より溶媒を除去した後、この２ｇを
カラムクロマト（充填剤；ワコーゲルＣ−２００，４０
ｇ）で５つの分画に分離し、各フラクションを減圧留去
し、更に６０℃、２時間減圧乾燥して、各々の留分を得
た。その結果を表−１に示す。なお、これらの留分のう
ち、グルコ−スジ脂肪酸エステルは無味であった。Next, after removing the solvent from this crude product, 2 g of this was subjected to column chromatography (filling material: Wakogel C-200, 40
g) into five fractions, each fraction was distilled off under reduced pressure, and further dried under reduced pressure at 60° C. for 2 hours to obtain each fraction. The results are shown in Table-1. Note that among these fractions, glucose difatty acid ester was tasteless.
１１−
表−ｌ
得られたグルコースモノ脂肪酸エステル留分は苦みを有
していたが、この留分にジエチルエーテルを加えて分散
後、濾別・乾燥したところ、実質的に無味なグルコース
モノ脂肪酸エステル留分が得られた。11-Table-l The obtained glucose monofatty acid ester fraction had a bitter taste, but when diethyl ether was added to this fraction and dispersed, filtered and dried, the glucose monofatty acid ester fraction was found to be essentially tasteless. An ester fraction was obtained.
実施例２
実施例１の反応粗生成物１ｇを、シリカゲル充填剤（ワ
コーゲルＣ−２００，２０ｇ）でシリカゲルカラムクロ
マトを行ない、下記の５種類の溶離液を順次流した後、
各フラクションをロータリーエバボレー１２−
ターにより、減圧留去し、更に６０℃で１時間減圧乾燥
して各々の留分を得た。その結果を表−２に示す。なお
、これらの留分のうち、糖ジ脂肪酸エステルは無味であ
った。Example 2 1 g of the reaction crude product of Example 1 was subjected to silica gel column chromatography using a silica gel packing material (Wako Gel C-200, 20 g), and the following five types of eluents were sequentially passed through, and then
Each fraction was distilled off under reduced pressure using a rotary evaporator 12-meter and further dried under reduced pressure at 60°C for 1 hour to obtain each fraction. The results are shown in Table-2. Note that among these fractions, sugar difatty acid ester was tasteless.
表−２
得られたグルコースモノ脂肪酸エステル留分は苦みを有
していたが、この留分に酢酸エチルを加えて分散後、濾
別・減圧乾燥したところ、実質的に無味なグルコースモ
ノ脂肪酸エステル留分が得られた。Table 2 The obtained glucose monofatty acid ester fraction had a bitter taste, but when ethyl acetate was added to this fraction and the fraction was dispersed, filtered and dried under reduced pressure, the glucose monofatty acid ester was found to be essentially tasteless. A fraction was obtained.
Claims (1)
て得られた六炭糖脂肪酸エステル反応粗生成物を、ｎ−
ヘキサンを満したシリカゲル充填カラムの上部に供給、
分散させた後、下記４種類の溶離液をその順に流下させ
、糖トリ−、ジ−及びモノ−脂肪酸エステルの夫々を分
別回収することを特徴とする糖モノ−、ジ−及びトリ−
脂肪酸エステルの分別回収方法。 （ｉ）ジエチルエーテル／ｎ−ヘキサン１／３（Ｖ／Ｖ
）溶離液（ｉｉ）ジエチルエーテル／ｎ−ヘキサン１／
１（Ｖ／Ｖ）溶離液（ｉｉｉ）ジエチルエーテル溶離液 （ｉｖ）メタノール／エチルエーテル１／９（Ｖ／Ｖ）
溶離液（２）請求項（１）で得られた糖モノ脂肪酸エス
テルをジエチルエーテル、ジイソプロピルエーテル、ア
セトン、及び酢酸エチルから選ばれた少くとも１種の溶
媒に分散させた後、不溶物を濾別し、減圧乾燥すること
を特徴とする糖の６位に脂肪酸が結合した実質的に無味
の糖モノ脂肪酸エステルの分別回収方法。(1) The hexose fatty acid ester reaction crude product obtained by the reaction of hexose and fatty acid or fatty acid derivative is
Feed to the top of a silica gel packed column filled with hexane,
After dispersion, the following four types of eluents are allowed to flow down in that order to separately recover sugar tri-, di-, and mono-fatty acid esters.
Method for separating and recovering fatty acid esters. (i) Diethyl ether/n-hexane 1/3 (V/V
) Eluent (ii) diethyl ether/n-hexane 1/
1 (V/V) Eluent (iii) Diethyl ether eluent (iv) Methanol/ethyl ether 1/9 (V/V)
Eluent (2) After dispersing the sugar monofatty acid ester obtained in claim (1) in at least one solvent selected from diethyl ether, diisopropyl ether, acetone, and ethyl acetate, insoluble matter is filtered. A method for fractionating and recovering a substantially tasteless sugar monofatty acid ester in which a fatty acid is bound to the 6-position of the sugar, the method comprising separating the sugar and drying it under reduced pressure.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32305589A JPH03184988A (en) | 1989-12-12 | 1989-12-12 | Fractional recovery of saccharide mono-, di-and tri-fatty acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32305589A JPH03184988A (en) | 1989-12-12 | 1989-12-12 | Fractional recovery of saccharide mono-, di-and tri-fatty acid ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03184988A true JPH03184988A (en) | 1991-08-12 |
Family
ID=18150594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32305589A Pending JPH03184988A (en) | 1989-12-12 | 1989-12-12 | Fractional recovery of saccharide mono-, di-and tri-fatty acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03184988A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105534867A (en) * | 2016-01-25 | 2016-05-04 | 王嫣俐 | Edible child health care toothpaste and preparation method thereof |
-
1989
- 1989-12-12 JP JP32305589A patent/JPH03184988A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105534867A (en) * | 2016-01-25 | 2016-05-04 | 王嫣俐 | Edible child health care toothpaste and preparation method thereof |
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