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PROCESS FOR PRODUCING SUGAR FATTY ACID ESTER USING ANION EXCHANGER AS CATALYST

Foreign code F180009360
File No. (S2016-1061-N0)
Posted date Apr 19, 2018
Country WIPO
International application number 2017JP029937
International publication number WO 2018038103
Date of international filing Aug 22, 2017
Date of international publication Mar 1, 2018
Priority data
  • P2016-162015 (Aug 22, 2016) JP
Title PROCESS FOR PRODUCING SUGAR FATTY ACID ESTER USING ANION EXCHANGER AS CATALYST
Abstract The purpose of the present invention is to provide a process for producing a sugar fatty acid ester such as sucrose fatty acid ester (FASuc) and provide a composition containing the sugar fatty acid ester, the process solving the various problems of conventional processes for producing such esters. The process has advantages including no generation of a by-product soap and ease of separation between the catalyst and the reaction product, and enables the ester to be efficiently synthesized in a flow system by a simple operation under mild conditions. The present invention relates to: a process for producing a sugar fatty acid ester by transesterification between a fatty acid ester and a sugar using an anion exchanger as a catalyst; and a composition containing the sugar fatty acid ester.
Outline of related art and contending technology BACKGROUND ART
The sugar is sucrose (Suc), about 1.8 billion tons per year it is said that the amount of production, as a single organic compound, having the largest production scale, high-purity products be available at low cost, various usages as a chemical raw material has been proposed. Current, and the industrial production as one of sucrose derivative, sucrose fatty acid ester is (FASuc).
Is FASuc, hydrophilic groups and lipophilic groups Suc FA is derived from vegetable oil fatty acid and an ester bond of the non-ionic surfactant. 8 Combine with the hydroxyl group of a sucrose fatty acid by the number of hydrophilic, lipophilic can be changed, a wide variety of hydrophilic, lipophilic balance (HLB) value. Is FASuc, in addition to the emulsifying action, the solubilizing ability, dispersing ability, has high functionality such as a lubricating ability.
In addition, in recent years, the pharmaceutical field, for use as a binder of tablets FASuc the studies performed, the pharmaceutical field is expected to be also used.
In this way, the FASuc, sugar produced from vegetable oils and inexpensive with high added value of the biomass-derived in a chemical, hydrophilic fatty acid and low miscibility Suc are difficult to be synthesized are known.
Current, industrial production processes are FASuc, dimethyl sulfoxide (DMSO) of the amphiphilic solvent is used, an Na phase equalizing2 CO3 Suc and fatty acid methyl esters catalyzed transesterification reaction (FAMe) has been used.
However, in order to enhance the conversion rate of the byproduct methanol (MeOH) is essential to the vacuum condition is removed, the catalyst by the reaction of the byproduct soap FAMe, uniform phase separation of the catalyst difficult, non-continuous operation, and has a problem, a factor of high cost. In order to cope with such a problem, for example, a packed column and a plurality of the condenser placed in series with the reactor, the second stage condenser 1 is filled with a liquid condensation reflux to the top of the tower are proposed (Patent Document 1).
Of another manufacturing method is the industrial FASuc, without using a catalyst and an organic solvent, an ester exchange an attempt has also been performed (Patent Document 2 and Patent Document 3). For example, to Patent Document 3, an aqueous solution of sucrose fatty acid methyl ester as an emulsifying agent was added to the sugar fatty acid ester, ultrasound and microwave was irradiated to the emulsion to a method to promote the reaction and have been described.
On the other hand, the inventors of the present invention, the fat and fatty alcohols and fatty acid esters by transesterification reaction in the method of manufacturing, the anion exchange body is used as a catalyst, an alcohol and fats 1/30-1/1 in the molar ratio of the fatty acid ester and a manufacturing method (Patent Document 4).
In addition, as a manufacturing method of the sucrose fatty acid ester, sucrose fatty acid glycerides or a lower alkanol and an alkali metal ion-exchanged cation exchange resin in the presence of the ester exchange reaction method is disclosed (Patent Document 5). However, a functional group having a quaternary ammonium group as the basic anion exchange resin having functional group of tertiary amine or a basic anion exchange resin is used when the reaction is not obtained satisfactory results have been described (Patent Document 5, page 4 left column).
Scope of claims (In Japanese)[請求項1]
脂肪酸エステルと糖類とのエステル交換反応を用いて糖脂肪酸エステルを製造する方法であって、触媒として陰イオン交換体を用いる前記方法。
[請求項2]
前記陰イオン交換体が、実質的に予め糖類が吸着された陰イオン交換体である請求項1に記載の方法。
[請求項3]
糖類を陰イオン交換体へ吸着させる吸着工程、次いで、吸着工程により糖類が吸着した陰イオン交換体を用いて糖脂肪酸エステルを合成させる合成工程を含む、請求項2に記載の方法。
[請求項4]
前記吸着工程が、糖類を含む反応液を陰イオン交換体に供給することにより糖類を陰イオン交換体へ吸着させることを特徴とする請求項3に記載の方法。
[請求項5]
前記合成工程が、前記吸着工程により糖類が吸着した陰イオン交換体に脂肪酸エステルを含む反応液を供給させることにより糖脂肪酸エステルを合成させることを特徴とする請求項3または4に記載の方法。
[請求項6]
前記脂肪酸エステルを含む反応液は、更に糖類を含むことを特徴とする請求項5に記載の方法。
[請求項7]
前記合成工程で使用する反応液に於ける脂肪酸エステルと糖類のモル濃度比が1:0.5~1:5である、請求項6記載の方法。
[請求項8]
陰イオン交換体が、強塩基性陰イオン交換樹脂である請求項1~7のいずれか一項に記載の方法。
[請求項9]
脂肪酸エステルが、炭素数1~30の脂肪酸と炭素数1~8の低級アルコールから成るエステルである、請求項1~8のいずれか一項にの方法。
[請求項10]
糖類が、単糖類、二糖類、及び、多糖類からなる群から選ばれる少なくとも1種である、請求項1~9のいずれか一項に記載の方法。
[請求項11]
脂肪酸エステルがオレイン酸メチルであり、糖類がスクロースである、請求項1~8のいずれか一項に記載の方法。
[請求項12]
請求項1~11のいずれか一項に記載の方法で製造された糖脂肪酸エステルを含む組成物。
[請求項13]
糖脂肪酸エステルの80質量%以上がモノ体であることを特徴とする、請求項12記載の組成物。
  • Applicant
  • ※All designated countries except for US in the data before July 2012
  • TOHOKU UNIVERSITY
  • Inventor
  • KITAKAWA Naomi
  • SASAYAMA Tomone
  • KAMIKANDA Yuto
IPC(International Patent Classification)
Specified countries National States: AE AG AL AM AO AT AU AZ BA BB BG BH BN BR BW BY BZ CA CH CL CN CO CR CU CZ DE DJ DK DM DO DZ EC EE EG ES FI GB GD GE GH GM GT HN HR HU ID IL IN IR IS JO JP KE KG KH KN KP KR KW KZ LA LC LK LR LS LU LY MA MD ME MG MK MN MW MX MY MZ NA NG NI NO NZ OM PA PE PG PH PL PT QA RO RS RU RW SA SC SD SE SG SK SL SM ST SV SY TH TJ TM TN TR TT TZ UA UG US UZ VC VN ZA ZM ZW
ARIPO: BW GH GM KE LR LS MW MZ NA RW SD SL SZ TZ UG ZM ZW
EAPO: AM AZ BY KG KZ RU TJ TM
EPO: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
OAPI: BF BJ CF CG CI CM GA GN GQ GW KM ML MR NE SN ST TD TG
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