JPH02139000A - Production of high-purity maltose - Google Patents
Production of high-purity maltoseInfo
- Publication number
- JPH02139000A JPH02139000A JP10218689A JP10218689A JPH02139000A JP H02139000 A JPH02139000 A JP H02139000A JP 10218689 A JP10218689 A JP 10218689A JP 10218689 A JP10218689 A JP 10218689A JP H02139000 A JPH02139000 A JP H02139000A
- Authority
- JP
- Japan
- Prior art keywords
- maltose
- rich fraction
- fraction
- content
- sugar solution
- 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
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 title claims abstract description 129
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 title claims abstract description 127
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 229920002472 Starch Polymers 0.000 claims abstract description 29
- 235000019698 starch Nutrition 0.000 claims abstract description 29
- 239000008107 starch Substances 0.000 claims abstract description 29
- 239000008103 glucose Substances 0.000 claims abstract description 18
- 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 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229920001353 Dextrin Polymers 0.000 claims abstract description 13
- 239000004375 Dextrin Substances 0.000 claims abstract description 13
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 13
- 235000019425 dextrin Nutrition 0.000 claims abstract description 13
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 11
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 10
- 230000002378 acidificating effect Effects 0.000 claims abstract description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 9
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 8
- 239000011347 resin Substances 0.000 claims description 37
- 229920005989 resin Polymers 0.000 claims description 37
- 239000000843 powder Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 5
- 239000011343 solid material Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 43
- 238000000034 method Methods 0.000 description 16
- 238000005194 fractionation Methods 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 8
- 239000003957 anion exchange resin Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 235000012907 honey Nutrition 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000002692 maltoses Chemical class 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- -1 alkali metal salt Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 108010019077 beta-Amylase Proteins 0.000 description 2
- 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 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- 229940023913 cation exchange resins Drugs 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 210000002196 fr. b Anatomy 0.000 description 2
- 210000000540 fraction c Anatomy 0.000 description 2
- 229940079826 hydrogen sulfite Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- 208000007976 Ketosis Diseases 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 108090000637 alpha-Amylases Proteins 0.000 description 1
- 102000004139 alpha-Amylases Human genes 0.000 description 1
- 229940024171 alpha-amylase Drugs 0.000 description 1
- 230000003625 amylolytic effect Effects 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000002584 ketoses Chemical class 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Abstract
Description
【発明の詳細な説明】 本発明は、高純度マルトースの製造方法に関する。[Detailed description of the invention] The present invention relates to a method for producing high purity maltose.
近年、マルトースの持つ長所が次々と見いだされ、その
用途は飲食物、医薬などに急速に拡大されてきた。In recent years, the advantages of maltose have been discovered one after another, and its uses have rapidly expanded to include foods, drinks, and medicine.
それにつれて、高純度マルトースに対する要望は非常に
高まってきた。Along with this, the demand for high purity maltose has increased significantly.
従来、マルトースは、液化澱粉に麦芽酵素を作用させて
、マルトース含有量が固形物当り約４０〜５０Ｗ／Ｗ％
（以下、特にことわらない限り、含有量％は、固形物当
りＷ／Ｗ％を意味する）の澱粉糖化物として供給されて
きた。近年になって、澱粉糖化方法の研究開発が進み、
例えば、澱粉枝切酵素とβ−アミラーゼとの併用により
澱粉からマルトース含有量５０％以上の澱粉糖化物も比
較的容易に得られるようになってきた。Conventionally, maltose is produced by treating liquefied starch with malt enzyme, and the maltose content is approximately 40 to 50 W/W% based on solid matter.
(Hereinafter, unless otherwise specified, content % means W/W % per solid matter). In recent years, research and development of starch saccharification methods has progressed,
For example, starch saccharified products with a maltose content of 50% or more can be obtained relatively easily from starch by using a starch debranching enzyme and β-amylase in combination.
しかし、これらの澱粉糖化方法によっても、澱粉からマ
ルトース含有量９０％以上の高純度マルトースを直接製
造することは経済的、技術的にかなり困難がともなって
いる。However, even with these starch saccharification methods, it is economically and technically very difficult to directly produce high-purity maltose with a maltose content of 90% or more from starch.
最近、高純度マルトースを製造する方法として、マルト
ースを含有する澱粉糖液なアニオン交換樹脂を充填した
カラムに通液する方法が開示されている。Recently, as a method for producing high-purity maltose, a method has been disclosed in which a maltose-containing starch sugar solution is passed through a column filled with an anion exchange resin.
例えば、昭和５２年特許出願公告第４６２９０号公報に
は、澱粉から主としてマルトースとデキストリンとから
なるマルトース含有置駒６５％の澱粉糖液を製造し、こ
の糖液なＯＨ型アニオン交換樹脂に通液し、マルトース
を選択的に吸着させ、デキストリンを分別除去する方法
により高純度マルトースを得ようとしている。しかしな
がら、この方法では、マルトースをＯＨ型イオン交換樹
脂に吸着させるため、その処理量が少ないだけでなく、
異性化を防ぐために、できるだけ低温望ましくは２０℃
以下で通液しなければならず、糖液の粘度上昇及び微生
物汚染を受は易（、工業的に実施することは極めて困難
である。For example, in Patent Application Publication No. 46290 of 1972, a starch sugar solution containing 65% maltose, which is mainly composed of maltose and dextrin, is produced from starch, and this sugar solution is passed through an OH-type anion exchange resin. However, attempts are being made to obtain high-purity maltose by selectively adsorbing maltose and fractionally removing dextrin. However, in this method, maltose is adsorbed onto the OH-type ion exchange resin, so not only is the amount of maltose processed small, but
To prevent isomerization, keep the temperature as low as possible, preferably 20°C.
The liquid must be passed through the process at a lower temperature, and the sugar solution is susceptible to increased viscosity and microbial contamination (and is extremely difficult to implement industrially).
また、昭和５４年特許出願公告第２０５７９号公報には
、マルトースとグルコースとを含有する澱粉糖液を、亜
硫酸型または亜硫酸水素型アニオン交換樹脂に通液し、
マルトースとグルコースとを分別して高純度マルトース
を得ようとしている。しかしながら、この方法は、アニ
オン交換樹脂から亜硫酸または亜硫酸水素がはずれやす
く、高純度マルトースの大量生産方法としては不適当で
ある。In addition, Patent Application Publication No. 20579 of 1982 discloses that a starch sugar solution containing maltose and glucose is passed through a sulfite type or hydrogen sulfite type anion exchange resin,
We are trying to obtain high-purity maltose by separating maltose and glucose. However, this method is unsuitable for mass production of high-purity maltose because sulfite or hydrogen sulfite is easily removed from the anion exchange resin.
本発明者らは、上述のような欠点を有するアニオン交換
樹脂を避け、カチオン交換樹脂、なかでもアルカリ金属
型またはアルカリ土類金属型強酸性カチオン交換樹脂を
用いる高純度マルトースの製造方法を鋭意研究した。The present inventors have conducted intensive research into a method for producing high-purity maltose using cation exchange resins, particularly alkali metal type or alkaline earth metal type strongly acidic cation exchange resins, avoiding anion exchange resins that have the drawbacks mentioned above. did.
その結果、原料の澱粉糖液（以下、単に原糖液と略称す
る。）をマルトース含有量７０％以上の澱粉糖液とし、
これをアルカリ金属型またはアルカリ土類金属型強酸性
カチオン交換樹脂を樹脂層の全長を７ｍ以上に充填した
カラムに流し、次いで水で溶出し、デキストリン高含有
画分、デキストリン・マルトース高含有画分、マルトー
ス高含有画分、マルトース・グルコース高含有画分及び
グルコース高含有画分の順になるように複数の画分、通
常５乃至１００、望ましくは５乃至３０両分に分画して
、このうちマルトース高含有画分を採取することにより
、容易に高純度マルトースが製造されることを見いだし
た。As a result, the raw starch sugar solution (hereinafter simply referred to as raw sugar solution) was made into a starch sugar solution with a maltose content of 70% or more,
This is passed through a column packed with an alkali metal type or alkaline earth metal type strongly acidic cation exchange resin so that the total length of the resin layer is 7 m or more, and then eluted with water to separate a dextrin-rich fraction and a dextrin/maltose-rich fraction. , fractionated into multiple fractions, usually 5 to 100, preferably 5 to 30, in the order of high maltose content fraction, high maltose/glucose content fraction, and high glucose content fraction, and It has been found that high purity maltose can be easily produced by collecting a fraction containing high maltose.
また、原料糊をカラムに流して分画するに際し、既に得
られているデキストリン・マルトース高含有画分及びマ
ルトース・グルコース高含有画分とともに流して分画し
、マルトース高含有画分を採取し、同時に得られるデキ
ストリン・マルトース高含有画分及びマルトース・グル
コース高含有画分を更に次回の原糖液とともに流す方式
な採用することにより目的とする高純度マルトースを高
濃度、高収率で繰り返し安定して製造し得ることを見い
だし、本発明を完成した。In addition, when the raw material glue is passed through the column and fractionated, it is passed together with the already obtained dextrin/maltose high content fraction and the maltose/glucose high content fraction, and the maltose high content fraction is collected. By using a system in which the dextrin/maltose-rich fraction and maltose/glucose-rich fraction obtained at the same time are further passed along with the next raw sugar solution, the target high-purity maltose can be repeatedly stabilized at high concentration and high yield. The present invention has been completed based on the discovery that it can be manufactured using the same method.
本発明に用いる原糖液は、マルトース含有量が７０％以
上で、実質的にケトースな含有しない澱粉質由来のアル
ドース混合物含有液であり、本発明によってマルトース
含有量９０％以上、望ましくはマルトース含有量９３％
以上の高純度マルトースが高収率で採取できるものであ
ればよく、例えば、澱粉にα−アミラーゼ、β−アミラ
ーゼ、澱粉枝切酵素などの澱粉分解酵素を作用させて得
られるマルトース含有量７０％以上の澱粉糖化液であっ
ても、また、マルトース含量７０％以上を含有する市販
の澱粉糖化物溶液であってもよい。The raw sugar solution used in the present invention has a maltose content of 70% or more and is a liquid containing an aldose mixture derived from starch that does not substantially contain ketose. Amount 93%
Any maltose with the above-mentioned high purity can be collected at a high yield. For example, a maltose content of 70% obtained by treating starch with an amylolytic enzyme such as α-amylase, β-amylase, or starch debranching enzyme is sufficient. The above starch saccharified solution may be used, or a commercially available starch saccharified solution containing 70% or more of maltose may be used.
また、本発明で使用されるアルカリ金属型またはアルカ
リ土類金属型強酸性カチオン交換樹脂には、例えば、ス
ルホン酸基を結合したスチレン−ジビニルベンゼン架橋
共重合体樹脂のＮａ’″型、Ｋ′″型などのアルカリ金
属塩型またはＣａ＋＋型、Ｍｇ−型などのアルカリ土類
金属塩型の１種または２種以上が適宜使用され、市販品
としては、例えば、ダウケミカル社製造の商品名ダウエ
ックス５０ＷＸ ２、ダウエックス５０ＷＸ４、ダウエ
ックス５０Ｗｘ８、ローム＆ハース社製造の商品名アン
バーライトＣＧ−１２０、東京有機化学工業社製造の商
品名ＸＴ−１０２２Ｅ、三菱化成工業社製造の商品名ダ
イヤイオン５ＫＩＢ、ダイヤイオン５Ｋ１０２、ダイヤ
イオン５Ｋ１０４などがある。これらの樹脂は、マルト
ース高含有画分の分画に優れているだけでなく、耐熱性
、耐摩耗性にも優れ、高純度マルトースの大量生産に極
めて有利である。In addition, examples of the alkali metal type or alkaline earth metal type strongly acidic cation exchange resin used in the present invention include Na''' type of styrene-divinylbenzene crosslinked copolymer resin bonded with sulfonic acid groups, K' One or more types of alkali metal salt types such as ``type'' or alkaline earth metal salt types such as Ca++ type and Mg- type are used as appropriate. X 50W , Diaion 5K102, and Diaion 5K104. These resins are not only excellent in fractionating high maltose-containing fractions, but also have excellent heat resistance and abrasion resistance, and are extremely advantageous for mass production of high-purity maltose.
本発明では、通常、０．０１＝０．５ｍｍ程度の粒径の
樹脂をカラムに充填して使用すればよい。カラム内に充
填する樹脂層の長さは全長で７ｍ以上が望ましく、この
際１本のカラムで７ｍ以上にしても、また、２本以上の
カラムを直列に連結して７ｍ以上にしてもよい。In the present invention, resin having a particle size of approximately 0.01=0.5 mm may be used by filling a column. The length of the resin layer filled in the column is preferably 7 m or more in total length, and in this case, one column may be 7 m or more, or two or more columns may be connected in series to be 7 m or more. .
カラムの材質、形状は、本発明の目的が達成できる限り
自由に選択できる。その材質は、例えば、ガラス、プラ
スチック、ステンレスなどが利用でき、その形状は充填
した樹脂層内を液ができるだけ層流になる、例えば、円
筒状、角柱状などが適宜利用できる。The material and shape of the column can be freely selected as long as the purpose of the present invention can be achieved. Its material can be, for example, glass, plastic, stainless steel, etc., and its shape can be appropriately used, such as a cylindrical shape or a prismatic shape, so that the liquid can flow as laminarly as possible within the filled resin layer.
以下、本発明の実施方法をより具体的に述べる。Hereinafter, the method of implementing the present invention will be described in more detail.
アルカリ金属型またはアルカリ土類金属型強酸性カチオ
ン交換樹脂を水に懸濁してカラムに充填して樹脂層の全
長が７ｍ以上になるようにし、このカラム内の温度を通
常４５℃〜８５℃に維持しつつ、これに濃度的１０〜７
０Ｗ／Ｗ％の原糖液を樹脂に対して約１〜６０ Ｖ／Ｖ
％を加え、これに水をＳｖ約０．１〜２．０の流速で上
昇法または下降法により流して溶出し、原糖液をデキス
トリン高含有画分、デキストリン・マルトース高含有画
分、マルトース高含有画分、マルトース・グルコース高
含有画分及びグルコース高含有画分に分画し、このマル
トース高含有画分を採取すればよい。An alkali metal type or alkaline earth metal type strongly acidic cation exchange resin is suspended in water and packed into a column so that the total length of the resin layer is 7 m or more, and the temperature inside this column is usually 45°C to 85°C. While maintaining this, the concentration is 10-7
Approximately 1 to 60 V/V of 0W/W% raw sugar solution to resin
% and elute by flowing water at a flow rate of about 0.1 to 2.0 Sv using an ascending or descending method. What is necessary is to fractionate into a high content fraction, a high maltose/glucose content fraction, and a high glucose content fraction, and collect this high maltose content fraction.
この際、溶出液の採取は、通常、使用樹脂に対して約１
〜２０Ｖ／Ｖ％毎に行われるが、これを自動化し、前記
画分に振り分けることも容易である。At this time, the eluate is usually collected at approximately 1% of the resin used.
This is carried out every ~20V/V%, but it is also easy to automate this and distribute it to the above-mentioned fractions.
また、原糖液をカラムに流して分画するに際し、既に得
られているデキストリン・マルトース高含有画分及びマ
ルトース・グルコース高含有画分を原糖液の前後に、ま
たは原糖液とともに流すことにより分画に要する使用水
量を減少させ、原糖液中のマルトースを高純度、高濃度
、高回収率で採取できるので好都合である。In addition, when fractionating the raw sugar solution by flowing it through a column, the already obtained dextrin/maltose-rich fraction and maltose/glucose-rich fraction may be passed before, after, or together with the raw sugar solution. This is advantageous because the amount of water required for fractionation can be reduced and maltose in the raw sugar solution can be collected with high purity, high concentration, and high recovery rate.
−ＪＱ的には、既に得られているデキストリン・マルト
ース高含有画分を流した後に原糖液を流し、次いで既に
知られているマルトース・グルコース高含有画分を流す
という順序を採用するのが好ましい。- From a JQ perspective, the following sequence is adopted: flow the already obtained dextrin/maltose high content fraction, then flow the raw sugar solution, and then flow the already known maltose/glucose high content fraction. preferable.
また、本発明で使用される分画法は、固定床方式、移動
床方式、擬似移動床方式のいずれであってもよい。Further, the fractionation method used in the present invention may be a fixed bed method, a moving bed method, or a pseudo moving bed method.
このようにして分画し、採取されたマルトース高含有画
分を、そのままで用いることもできるが、必要ならば、
常法に従って、例えば、濾過、脱色、脱塩、精製した後
、例えば、濃縮してシラツブとするか、さらに晶出させ
てマスキットとし、これを噴霧乾燥して含蜜結晶粉末と
するか、または晶出解せたマスキットを分蜜してさらに
高純度のマルトース結晶を採取することも自由である。The maltose-rich fraction collected in this way can be used as it is, but if necessary,
After filtration, bleaching, desalting, and purification according to conventional methods, for example, concentrating to obtain a silica, or further crystallizing it to obtain a muskit, which is then spray-dried to obtain a honey-containing crystal powder, or It is also free to extract maltose crystals of even higher purity by dividing the crystallized mascit into honey.
マスキットの調製方法は、通常３０〜７０℃の比較的高
温の過飽和マルトース溶液を助晶缶により、これに種晶
を望ましくは０．１〜２０％共存せしめて、ゆっくり撹
拌しつつ除冷し、晶出を促がせばよい。マスキットを噴
霧乾燥する場合は、通常、濃度７０〜８０％、晶出率２
５〜６０％程度のマスキ、ットを高圧ポンプでノズルか
ら噴霧するか、回転円板などを利用して噴霧し、結晶粉
末が溶融しない温度、例えば６０〜１００℃の熱風で乾
燥し、次いで３０〜６０℃の温風で約１〜２０時間熟成
すれば、非吸湿性又は難吸湿性の含蜜結晶が容易に製造
できる。また、ブロック粉砕方法の場合は、通常、水分
７〜１５％、晶出率ｌＯ〜６０％程度のマスキットを０
５〜７日間静置して全体をブロック状に晶出固化させ、
これを粉砕または切削などの方法によって粉砕し、乾燥
すれば、非吸湿性又は難吸湿性の含窒結晶が容易に製造
できる。更には、分蜜方法の場合は、マスキットをバス
ケット型遠心分離機にかけ、結晶と蜜とに分離する方法
で、必要により、該結晶に小量の冷水をスプレーして洗
浄することも容易であり、より高純度の結晶マルトース
を製造するのに好都合である。The method for preparing Maskit is to prepare a supersaturated maltose solution at a relatively high temperature of usually 30 to 70°C in a auxiliary crystal can, with preferably 0.1 to 20% of seed crystals coexisting therein, and slowly cooling while stirring. It is sufficient to promote crystallization. When spray drying Maskit, the concentration is usually 70-80% and the crystallization rate is 2.
About 5 to 60% maskite is sprayed from a nozzle with a high-pressure pump or using a rotating disk, dried with hot air at a temperature that does not melt the crystal powder, for example 60 to 100 ° C, and then By aging with warm air at 30 to 60°C for about 1 to 20 hours, non-hygroscopic or hardly hygroscopic honey-containing crystals can be easily produced. In addition, in the case of the block crushing method, the mass kit with a moisture content of 7 to 15% and a crystallization rate of 10 to 60% is usually
Let stand for 5 to 7 days to crystallize and solidify the whole into a block shape,
If this is pulverized by a method such as pulverization or cutting and dried, a non-hygroscopic or hardly hygroscopic nitrogen-containing crystal can be easily produced. Furthermore, in the case of the honey separation method, the mass kit is separated into crystals and honey by using a basket centrifuge, and if necessary, the crystals can be easily washed by spraying a small amount of cold water. , which is advantageous for producing higher purity crystalline maltose.
このようにして製造される高純度マルトースは、飲食物
、医薬など、更には、マルチトール結晶粉末の原料など
各種用途に対して有利に利用できる。The high-purity maltose produced in this way can be advantageously used for various purposes such as food and drink, medicine, and furthermore, raw material for maltitol crystal powder.
以下、本発明を実験で詳細に説明する。Hereinafter, the present invention will be explained in detail through experiments.
実験１．原糖液の比較
原糖液は、第１表に示した林原株式会社製造の各種澱粉
糖商品を濃度４５Ｗ／Ｗ％水溶液にして使用した。Experiment 1. Comparison of raw sugar solutions As raw sugar solutions, various starch sugar products manufactured by Hayashibara Co., Ltd. shown in Table 1 were used in an aqueous solution with a concentration of 45 W/W%.
樹脂は、アルカリ金属型強酸性カチオン交換樹脂（ダウ
ケミカル社製造、商品名ダウエックス５０ＷＸ４、Ｎａ
“型）を使用し、これを水懸濁液として内径５．４ｃｍ
のジャケット付ステンレス性カラム１本に樹脂層長が１
０ｍになるように充填した。The resin is an alkali metal type strong acid cation exchange resin (manufactured by Dow Chemical Company, trade name DOWEX 50WX4, Na
5.4cm inner diameter as a water suspension.
One jacketed stainless steel column with one resin layer length.
It was filled to a depth of 0 m.
カラム内温度を７５℃に維持しつつ、原糖液を樹脂に対
して５Ｖ／Ｖ％加え、これに７５℃の温水をＳＶｏ、４
の流速で流して分画し、マルトス含有量９３％以上のマ
ルトース高含有画分を採取した。結果は第２表に示した
。While maintaining the column internal temperature at 75°C, add 5V/V% raw sugar solution to the resin, and add 75°C warm water to it at SVo, 4
The maltose-rich fraction with a maltose content of 93% or more was collected. The results are shown in Table 2.
第 １ 表
第 ２ 表
チオン交換樹脂をカラムの１本または２本に充填し、そ
の樹脂層の全長を１〜２０ｍとした。Table 1 Table 2 One or two columns were filled with thione exchange resin, and the total length of the resin layer was 1 to 20 m.
これら樹脂層長の異なる各カラムに、カラム内温度を７
５℃に維持しつつ、マルトース含有量８５．０％の澱粉
糖（商品名サンマルト）を濃度４５Ｗ／Ｗ％水溶液とし
た原糖液を樹脂に対して５Ｖ／Ｖ％加え、７５℃の温水
をＳＶｏ、４の流速で流して各画分に分画し、マルトー
ス含有量９３％以上のマルトース高含有画分を採取した
。結果は第３表に示した。For each column with different resin layer length, the column internal temperature was set to 7.
While maintaining the temperature at 5℃, add 5V/V% of a raw sugar solution containing 85.0% maltose content starch sugar (trade name Sunmalt) to the resin at a concentration of 45W/W%, and add 75℃ hot water. It was run at a flow rate of SVo, 4 to separate each fraction, and a maltose-rich fraction with a maltose content of 93% or more was collected. The results are shown in Table 3.
組成としてマルトース含有量を７０％以上にすれば、マ
ルトース含有量９３％以上のマルトース高含有画分中に
マルトースが原糖液マルトースに対して８０％以上の高
収率で採取できることが判明した。It has been found that when the maltose content is set to 70% or more, maltose can be collected in a maltose-rich fraction with a maltose content of 93% or more at a high yield of 80% or more based on maltose in the raw sugar solution.
実験２．樹脂層長の比較
実験１と同様にして、アルカリ金属型強酸性力第 ３
表
長を７ｍ以上にすれば、マルトース含有量９３％以上の
マルト−ス高含有画分中にマルトースが原糖液マルトー
スに対して８０％以上にも達し、樹脂層の全長が６ｍ以
下の場合と比較して極めて高収率に採取できることが判
明した。Experiment 2. In the same manner as in Comparative Experiment 1 for Resin Layer Length, alkali metal type strong acidic force No. 3 was conducted.
If the surface length is 7 m or more, the maltose in the maltose-rich fraction with a maltose content of 93% or more will reach 80% or more of the maltose in the raw sugar solution, and the total length of the resin layer is 6 m or less. It was found that it could be collected at an extremely high yield compared to the conventional method.
実験３ 分画時の温度の比較
実験ｌと同様にして、アルカリ金属型強酸性カチオン交
換樹脂を樹脂層長が１０ｍになるように充填し、このカ
ラムに実験２と同様にして調整した原糖液を加え、カラ
ム内温度を３５〜９５℃に変えた以外は、実験２と同様
に分画して、マルトス含有量９３％以上のマルトース高
含有画分を採取した。Experiment 3 Comparison of temperature during fractionation In the same manner as in Experiment 1, an alkali metal type strongly acidic cation exchange resin was packed so that the resin layer length was 10 m, and raw sugar prepared in the same manner as in Experiment 2 was packed in this column. The fractionation was carried out in the same manner as in Experiment 2, except that the column temperature was changed to 35 to 95° C., and a maltose-rich fraction with a maltose content of 93% or more was collected.
結果は第４表に示した。The results are shown in Table 4.
第３表の結果から明らがなように、樹脂層の全第 ４
表
（注）表中、着色度（Ａ）とはマルトース高含有画分の
糖液な１０ｃｍセルで吸光度（Ａ４２０ｎｍＡ７□。、
）を測定し、糖濃度３０Ｗ／Ｗ％として表示した値であ
る。As is clear from the results in Table 3, all 4 parts of the resin layer
Table (Note) In the table, the degree of coloration (A) refers to the absorbance (A420nmA7□.
) was measured and the value is expressed as a sugar concentration of 30W/W%.
第４表の結果から明らかなように、分画温度を４５〜８
５℃の範囲内にすれば、糖の褐変着色を懸念することも
なく、マルトース含有量９３％以上のマルトース高含有
画分中にマルトースが原糖液マルトースに対して８０％
以上の高収率で採取できることが判明した。As is clear from the results in Table 4, the fractionation temperature was set at 45-8
If the temperature is within the range of 5℃, there is no concern about browning or coloring of the sugar, and the maltose in the maltose-rich fraction with a maltose content of 93% or more is 80% of the maltose in the raw sugar solution.
It was found that it could be collected with a higher yield than above.
以下、２〜３の実施例を述べる。A few examples will be described below.
実施例１
マルトース含有量７６．８％の澱粉糖液（林原株式会社
製造、商品名ＨＭ−７５）を濃度４５Ｗ／Ｗ％水溶液に
して原糖液とした。樹脂は、アルカリ金属型強酸性カチ
オン交換樹脂（東京有機化学工業社製造、商品名ＸＴ−
１０２２Ｅ、Ｎａ＋型）を使用し、内径５．４ｃｍのジ
ャケット付ステンレス製カラム水懸濁液状で充填した。Example 1 A starch sugar solution with a maltose content of 76.8% (manufactured by Hayashibara Co., Ltd., trade name HM-75) was made into an aqueous solution with a concentration of 45 W/W% to obtain a raw sugar solution. The resin is an alkali metal type strong acid cation exchange resin (manufactured by Tokyo Organic Chemical Industry Co., Ltd., trade name XT-
1022E, Na+ type) was used, and a jacketed stainless steel column with an inner diameter of 5.4 cm was packed in the form of a water suspension.
この際、樹脂層長５ｍのカラム４本に充填し、その液が
直列に流れるようにカラム４本を連結して樹脂層全長を
２０ｍとした。At this time, four columns each having a resin layer length of 5 m were filled, and the four columns were connected so that the liquid flowed in series, so that the total length of the resin layer was 20 m.
カラム内温度を５５℃に維持しつつ、原糖液を樹脂に対
して５Ｖ／Ｖ％加え、これに５５℃の温水をＳＶｏ、１
３の流速で流して分画し、マルトス含有量９３％以上の
マルトース高含有画分を採取した。このマルトース高含
有画分には、マルトースが８０８．２ｇ含まれ、原糖液
マルトースに対して８４．３％の高収率であった。While maintaining the column internal temperature at 55°C, 5V/V% raw sugar solution was added to the resin, and 55°C warm water was added to it at SVo, 1
The mixture was fractionated by flowing at a flow rate of 3, and a maltose-rich fraction with a maltose content of 93% or more was collected. This maltose-rich fraction contained 808.2 g of maltose, and had a high yield of 84.3% based on maltose in the raw sugar solution.
実施例２
マルトース含有量８５．０％の澱粉糖粉末（林原株式会
社製造、商品名サンマルト）を濃度６０Ｗ／Ｗ％水溶液
にして原糖液とした。樹脂は、実施例１に用いたものを
に１型に変えた後使用し、内径２’、２ｃｍのジャケッ
ト付ステンレス製カラム１本に樹脂層長がｌｏｍになる
ように充填した。Example 2 Starch sugar powder (manufactured by Hayashibara Co., Ltd., trade name: Sunmalt) with a maltose content of 85.0% was made into an aqueous solution with a concentration of 60 W/W% to obtain a raw sugar solution. The resin used in Example 1 was changed to type 1, and one jacketed stainless steel column with an inner diameter of 2' and 2 cm was filled with the resin so that the resin layer length was lom.
カラム内温度を６０℃に維持しつつ、原糖液を樹脂に対
して３Ｖ／Ｖ％加え、これに６０℃の温水をＳＶｏ、２
の流速で流して分画し、マルトース含有量９３％以上の
マルトース高含有画分を採取した。このマルトース高含
有画分にはマルトスが６５．７ｇ含まれ、原糖液マルト
ースに対して８８．３％の高収率であった。While maintaining the column internal temperature at 60°C, add 3V/V% raw sugar solution to the resin, and add 60°C warm water to it at SVo, 2
It was fractionated by flowing at a flow rate of , and a maltose-rich fraction with a maltose content of 93% or more was collected. This maltose-rich fraction contained 65.7 g of maltos, and had a high yield of 88.3% based on maltose in the raw sugar solution.
実施例３
マルトース含有量８５０％の澱粉糖粉末（商品名サンマ
ル日を濃度４５Ｗ／Ｗ％水溶液にして原糖液とした。樹
脂は、アルカリ土類金属型強酸性カチオン交換樹脂（ダ
ウケミカル社製造、商品名ダウエックス５０ＷＸ４、Ｍ
ｇ”型）を使用し、実施例１と同じカラムに樹脂層の全
長が１５ｍになるように充填した。カラム内温度を７５
℃に維持しつつ原糖液を樹脂に対して６．６Ｖ／Ｖ％加
え、これに７５℃の温水をＳＶｏ、１３の流速で流して
９分画し、マルトース含有量９３％以上のマルトース高
含有画分を採取した。このマルトース高含有画分にはマ
ルトースが９１３．７ｇ含まれ、原糖液マルトースに対
して８７．１％の高収率であった。Example 3 Starch sugar powder (trade name: Sanmaruhi) with a maltose content of 850% was made into an aqueous solution with a concentration of 45 W/W% to obtain a raw sugar solution.The resin was an alkaline earth metal type strong acid cation exchange resin (manufactured by Dow Chemical Company) , Product name DOWEX 50WX4, M
The same column as in Example 1 was packed so that the total length of the resin layer was 15 m.The temperature inside the column was set to 75 m.
6.6 V/V% of the raw sugar solution was added to the resin while maintaining the temperature at The containing fraction was collected. This maltose-rich fraction contained 913.7 g of maltose, and had a high yield of 87.1% based on maltose in the raw sugar solution.
実施例４
まず、第１回目の分画に際して、原糖液を樹脂に対して
２０Ｖ／Ｖ％使用した以外は、実施例３と同様にして分
画した。分画品の溶出パターンを区に示した。Example 4 First, fractionation was carried out in the same manner as in Example 3, except that in the first fractionation, the raw sugar solution was used at 20 V/V% relative to the resin. The elution patterns of fractionated products are shown in the diagram.
図で、Ａはデキストリン高含有画分を示し、Ｂはデキス
トリン マルトース高含有画分を示し、Ｃはマルトース
高含有画分を示し、Ｄはマルトス・グルコース高含有画
分を示し、Ｅはグルコース高含有画分を示す。その溶出
順序はＡ、Ｂ、Ｃ，Ｄ、Ｈの順であった。In the figure, A shows a fraction with high dextrin content, B shows a fraction with high dextrin-maltose content, C shows a fraction with high maltose content, D shows a fraction with high maltos-glucose content, and E shows a fraction with high glucose content. Containing fractions are shown. The elution order was A, B, C, D, H.
分画品Ｃ（マルトース高含有画分）は採取し、分画品Ａ
及びＥは除去した。Fraction C (high maltose content fraction) was collected, and fraction A
and E were removed.
第２回目以降の分画は同じカラムに分画品Ｂ、樹脂に対
して約１０Ｖ／Ｖ％の原糖液及び分画品りの順に加え、
更に７５℃の温水を実施例３と同様に流してマルトース
含有量９４％のマルトース高含有画分を採取した。第２
回目以降の分画操作を延べ３０回繰り返して１回当りの
平均結果を求めたところ、マルトース高含有画分にはマ
ルトスが１４８３ｇ含まれ、原糖液マルトースに対して
９３．３％の高収率であった。For the second and subsequent fractions, add fraction B, raw sugar solution at about 10 V/V% to the resin, and fraction products to the same column in that order.
Furthermore, hot water at 75° C. was poured in the same manner as in Example 3, and a maltose-rich fraction with a maltose content of 94% was collected. Second
After repeating the fractionation operation a total of 30 times and calculating the average result per time, the maltose-rich fraction contained 1483g of maltose, which was a high yield of 93.3% based on maltose in the raw sugar solution. The rate was
実施例５
マルトース含有量９１．５％の澱粉糖粉末（林原株式会
社製造、商品名マルトースＨ）を濃度４５Ｗ／Ｗ％水溶
液にして原糖液とした。樹脂は、アルカリ土類金属型強
酸性カチオン交換樹脂（口ム＆ハース社製造、商品名ア
ンバーライトＣＧ−１２０、Ｃａ＋ ＋型）を使用し、
実施例１で使用したカラムに、樹脂層の全長が１０ｍに
なるように充填した。カラム内温度を８０℃に維持しつ
つ原糖液を樹脂に対して第１回目の分画に際しては２０
Ｖ／Ｖ％加え、これに８０℃の温水をＳＶｏ ６の流速
で流し分画した。Example 5 Starch sugar powder (manufactured by Hayashibara Co., Ltd., trade name: Maltose H) with a maltose content of 91.5% was made into an aqueous solution with a concentration of 45 W/W% to obtain a raw sugar solution. The resin used was an alkaline earth metal type strong acid cation exchange resin (manufactured by Kuchimu & Haas, trade name Amberlite CG-120, Ca+ type).
The column used in Example 1 was packed so that the total length of the resin layer was 10 m. During the first fractionation of the raw sugar solution against the resin, the temperature inside the column was maintained at 80°C.
% V/V was added, and 80° C. hot water was flowed thereto at a flow rate of SVo 6 for fractionation.
実施例４の場合と同様に分画品Ｃ（マルトース高含有画
分）は、採取し、分画品Ａ及びＥは除去した。第２回目
以降の分画は同じカラムに分画品Ｂ、樹脂に対して約１
０Ｖ／Ｖ％の原糖液、及び分画品りの順に加え、更に８
０℃の温水をＳＶｏ、６の流速で流してマルトース含有
量９６％以上のマルトース高含有画分を採取した。As in Example 4, fraction C (high maltose content fraction) was collected, and fractions A and E were removed. For the second and subsequent fractions, add fraction B to the same column, approximately 1% to the resin.
Add 0V/V% raw sugar solution and fractionated product in that order, and then add 8
Hot water at 0° C. was flowed at a flow rate of SVo, 6 to collect a maltose-rich fraction having a maltose content of 96% or more.
第２回目以降の分画操作を延べ１００回繰り返して１回
当りの平均結果を求めたところ、マルトース含有量分に
はマルトースが１０８４ｇ含まれ、原糖液マルトースに
対して９５％の高収率であった。When the fractionation operation from the second time onwards was repeated a total of 100 times and the average result per time was calculated, the maltose content contained 1084g of maltose, a high yield of 95% based on the maltose in the raw sugar solution. Met.
図は、原糖液の溶出パターンの一例を示す図である。図
中の符号Ａはデキストリン高含有画分、Ｂはデキストリ
ン・マルトース高含有画分、Ｃはマルトース高含有画分
、Ｄはマルトース・グルコース高含有画分、及びＥはク
ルコース高含有画分を示す。The figure is a diagram showing an example of an elution pattern of a raw sugar solution. In the figure, the symbol A indicates the dextrin-rich fraction, B the dextrin/maltose-rich fraction, C the maltose-rich fraction, D the maltose-glucose-rich fraction, and E the glucose-rich fraction. .
Claims (4)
糖液を、アルカリ金属型又はアルカリ土類金属型強酸性
カチオン交換樹脂を樹脂層の全長を７ｍ以上に充填した
カラムに流し、次いで水で溶け出しデキストリン高含有
画分、デキストリン・マルトース高含有画分、マルトー
ス含有量が固形物当り９０％以上のマルトース高含有画
分、マルトス・グルコース高含有画分及びグルコース高
含有画分の順に分画し、このマルトース高含有画分を採
取してマルトース含有量が固形物当り９０％以上の高純
度マルトースを澱粉糖液中のマルトースに対して８０％
以上の収率で得ることを特徴とする高純度マルトースの
製造方法。(1) A starch sugar solution with a maltose content of 70% or more based on solid matter is poured into a column packed with an alkali metal type or alkaline earth metal type strongly acidic cation exchange resin to a resin layer with a total length of 7 m or more, and then water The dextrin-rich fraction, the dextrin-maltose-rich fraction, the maltose-rich fraction with a maltose content of 90% or more based on solids, the maltos-glucose-rich fraction, and the glucose-rich fraction are separated in this order. The maltose-rich fraction is collected to obtain high-purity maltose with a maltose content of 90% or more based on solid matter, which is 80% of the maltose in the starch sugar solution.
A method for producing high-purity maltose, which is characterized in that it can be obtained with a yield of at least 10%.
とを特徴とする特許請求の範囲第１項又は第２項記載の
高純度マルトースの製造方法。(2) The method for producing high-purity maltose according to claim 1 or 2, characterized in that the temperature inside the column is maintained in the range of 45 to 85°C.
たマルトース高含有画分を濃縮し、マルトースを晶出さ
せる工程を含むことを特徴とする特許請求の範囲第１項
又は第２項記載の高純度マルトースの製造方法。(3) Claim 1 or 2, wherein the step of collecting the high maltose content fraction includes a step of concentrating the fractionated high maltose content fraction and crystallizing maltose. The method for producing high purity maltose as described.
特徴とする特許請求の範囲第３項記載の高純度マルトー
スの製造方法。(4) The method for producing high-purity maltose according to claim 3, wherein the obtained high-purity maltose is a powder product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1102186A JPH0614880B2 (en) | 1989-04-22 | 1989-04-22 | Method for producing high-purity maltose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1102186A JPH0614880B2 (en) | 1989-04-22 | 1989-04-22 | Method for producing high-purity maltose |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56121725A Division JPS5823799A (en) | 1981-08-03 | 1981-08-03 | Production of high purity maltose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02139000A true JPH02139000A (en) | 1990-05-28 |
| JPH0614880B2 JPH0614880B2 (en) | 1994-03-02 |
Family
ID=14320637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1102186A Expired - Lifetime JPH0614880B2 (en) | 1989-04-22 | 1989-04-22 | Method for producing high-purity maltose |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0614880B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008137982A (en) * | 2006-12-01 | 2008-06-19 | Shin Dong Bang Cp Corp | Process for preparing high-purity crystalline maltitol powder |
| CN110938714A (en) * | 2019-12-03 | 2020-03-31 | 山东福田药业有限公司 | Production method of high-purity crystal maltose |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4109075A (en) * | 1976-06-09 | 1978-08-22 | Cpc International Inc. | Separation of saccharides by exclusion chromatography |
-
1989
- 1989-04-22 JP JP1102186A patent/JPH0614880B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4109075A (en) * | 1976-06-09 | 1978-08-22 | Cpc International Inc. | Separation of saccharides by exclusion chromatography |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008137982A (en) * | 2006-12-01 | 2008-06-19 | Shin Dong Bang Cp Corp | Process for preparing high-purity crystalline maltitol powder |
| CN110938714A (en) * | 2019-12-03 | 2020-03-31 | 山东福田药业有限公司 | Production method of high-purity crystal maltose |
| CN110938714B (en) * | 2019-12-03 | 2023-08-15 | 山东福田药业有限公司 | Production method of high-purity crystalline maltose |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0614880B2 (en) | 1994-03-02 |
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