1,3-プロパンジオール 化学特性,用途語,生産方法
外観
無色〜ほとんど無色, 澄明の液体
定義
本品は、次の化学式で表される二価アルコールである。
溶解性
水、エタノール及びアセトンに溶ける。
用途
工業用および化粧品?パーソナルケア原料
化粧品の成分用途
減粘剤、溶剤
使用上の注意
アルゴン封入
解説
1,3-プロパンジオール：HO(CH2)3OH．臭化トリメチレンの加水分解，アクリルアルデヒドに水を付加させた後還元してつくる．淡黄緑色の粘ちゅうな液体．甘味をもつ．融点－32 ℃，沸点201～211 ℃．d
20D1.053．n
20D1.439．水，エタノール，エーテルに易溶．
化学的特性
1,3-Propanediol, an isomer of propylene glycol, is a viscous, colorless, odorless, hygroscopic liquid that has a brackish irritating taste. miscible with various solvents such as water, ethanol, acetone, chloroform (chloroform) and ether, and is insoluble in benzene. Combustible.
定義
ChEBI: Propane-1,3-diol is the simplest member of the class of propane-1,3-diols, consisting of propane in which one hydrogen from each methyl group is substituted by a hydroxy group. A colourless, viscous, water-miscible liquid with a high (210℃) boiling point, it is used in the synthesis of certain polymers and as a solvent and antifreeze. It has a role as a protic solvent and a metabolite.
主な応用
1,3-Propanediol /PDO/ is mainly used for making polytrimethylene terephthalate polymer, which is used in fibers and fabrics, for example, carpets, textiles, engineering thermoplastics, nonwovens, films, and monofilaments. PDO finds also use as chain extender in thermoplastic polyurethanes, where it contributes to improved thermal, hydrolytic and dimensional stability. In adipate polyesters with other diols these diols are partly substituted by 1,3-propanediol to break crystallinity in order to obtain liquid polyester polyols. In polyesters for powder coatings PDO improves the flexibility but lowers the glass transition temperature somewhat. PDO finds also uses in cosmetics and personal care products, engine coolants, and solvents for ink-jet and screen inks.
生合成
1,3-Propanediol (1,3-PDO) can be produced by fermentation from glycerol, with different strains such as Klebsiella pneumoniae, Clostridium butyricum, Clostridium pasteurianum, and Citrobacter freundii. Drawbacks of industrial fermentation using these strains are strong inhibition of 1,3-PDO production and by-products during fermentation.
化学性质
100％植物由来のバイオ化学品
合成
1,3-Propanediol is produced commercially by Degussa starting from acrolein.
CH2CHCHO + H2O → HOHCH2CH2CHO
HOHCH2CH2CHO + H2 → HOHCH2CH2CH2OH
The addition of water under mild acidic conditions gives 3-hydroxypropionaldehyde with high selectivity. Preferentially buffer solutions with a pH 4-5 or weak acidic ion exchange resins are used as catalysts. Further hydrogenation of this aqueous solutions gives 1,3-propanediol. There is an alternative route via hydroformylation of ethylene oxide and subsequent hydrogenation of the intermediate 3-hydroxypropionaldehyde.
合成方法
バイオマス原料から得られるグルコースが大腸菌内の代謝経路を経由してグリセロールに変換され，さらに2段階の酵素反応を経ることで生産される
純化方法
Dry this diol with K2CO3 and distil it under reduced pressure. More extensive purification involves conversion with benzaldehyde to 2-phenyl-1,3-dioxane (m 47-48o) which is subsequently decomposed by shaking with 0.5M HCl (3mL/g) for 15minutes and standing overnight at room temperature. After neutralisation with K2CO3, the benzaldehyde is removed by steam distillation and the diol is recovered from the remaining aqueous solution by continuous extraction with CHCl3 for 1day. The extract is dried with K2CO3, the CHCl3 is evaporated and the diol is distilled. [Foster et al. Tetrahedron 6 177 1961, Beilstein 1 IV 2493.]
1,3-プロパンジオール 上流と下流の製品情報
原材料
準備製品