亜りん酸トリエチル 化学特性,用途語,生産方法
外観
無色澄明の液体
溶解性
水に難溶, エタノールに混和。エタノール及びアセトンに極めて溶けやすく、水にほとんど溶けない。
解説
C6H15O3P(166.16).(C2H5O)3P.亜リン酸トリエチル,トリエチルホスファイトともいう.三塩化リンとエタノールまたはエトキシドとを反応させると得られる.特有の臭気を有する無色の液体.沸点156 ℃,57~58 ℃(2.13 kPa).[α]20D 0.969.n20D 1.413.エタノール,エーテルに可溶,水に難溶.アルキル化試薬,脱酸素,脱硫黄試薬,殺虫剤合成中間体として使用される.高分子安定剤にも用いられる.森北出版「化学辞典(第2版)
用途
ホスホン酸エチルの合成やアルキル化試薬、脱酸素、脱硫黄試薬として有機合成に広く用いられる。高分子安定剤、難燃性高分子、潤滑油添加剤、殺虫剤などの合成原料。
化学的特性
Triethyl phosphite is a clear colorless liquid with a strong foul odor. Insoluble in water; soluble in alcohol and ether. Combustible.Vapors heavier than air.
使用
Triethyl phosphite is an organophosphorus compound. It is used as a reducing agent; can react with electrophiles to form phosphonates or phosphates; forms a stable complex with copper(I) iodide.
Triethyl phosphite is a very good nucleophile. The carbon adjacent to the bromine is the most electrophilic position, and phosphorus is the only nucleophile. Triethyl phosphite displaces the bromine in an SN2-like process, and back attack by the bromide which is released generates a phosphonate product, in which the α-protons are strongly acidic.
製造方法
Triethyl phosphite is produced in a closed system by reaction of phosphorous trichlorid and ethanol in the presence of an inorganic or organic base. The product is purified by distillation (Bayer AG, 2002a).
![説明図](https://www.chemicalbook.com/NewsImg/2020-06-29/2020629129228818.jpg)
Triethyl phosphite is exclusively used as an intermediate for the manufacturing of different products: flame retardants (about 60 %), optical brighteners (about 15 %), pesticides (about 15 %), antioxidants (about 5 %), and pharmaceuticals (about 5 %).
反応性
This reaction is currently used for the preparation of synthetically useful phosphonate reagents employed in modified retinal studies. Thus, diethyl 3-alkoxycarbonyl-2-propenylphosphonates are prepared in 72-91% yields by the reaction of methyl or ethyl 4-bromocrotonates with triethyl phosphite at 150-160°C. Similarly, diethyl 3-(ethoxycarbonyl)-2 methyl-2-propenylphosphonate is prepared in 81% yield from triethyl phosphite and ethyl 3-methyl-4-chlorocrotonate by heating at 180- 200°C.The diethyl (E)- and (Z)-3-ethoxycarbonyl-3 fluoro-2 -methyl-2-propenylphosphonates are respectively obtained from triethyl phosphite and (E)- or (Z)-4-bromo-2-fuoro-3-methyl-2-butenoates at 140°C.
反応プロフィール
Triethyl phosphite is colorless, moderately toxic liquid, combustible. Flammable when exposed to heat or flame. When heated to decomposition Triethyl phosphite emits toxic fumes of oxides of phosphorus [Lewis, 3rd ed., 1993, p. 1271].
健康ハザード
Exposure to high concentrations may cause headache, nausea, and dizziness due to reduced chlolinesterase activity.
火災危険
Special Hazards of Combustion Products: May form hazardous decomposition products.
安全性プロファイル
Moderately toxic by
ingestion. A skin and eye irritant. Flammable
liquid when exposed to heat, sparks, or
flame. When heated to decomposition it
emits toxic fumes of POx.
亜りん酸トリエチル 上流と下流の製品情報
原材料
準備製品
2-(2,3-DIHYDRO-1BENZENESULFONYL-PYRROLO[2,3-B]PYRIDIN-3-YL)ETHANAMINE
4'-(2-シアノスチリル)-4-スチルベンカルボニトリル
2-[2-(2-チエニル)エチル]安息香酸
(N-メトキシ-N-メチルカルバモイルメチル)ホスホン酸ジエチル
Phosphite
エチルジチオホスホン酸O-エチルS-フェニル
1,1-シクロペンタン二酢酸
2,1,3-ベンゾオキサジアゾール-4-カルボキシアルデヒド
2-アミノエチルホスホン酸
1,2-ジ(4-ピリジル)エチレン
(4-ニトロベンジル)ホスホン酸ジエチル
1-CYCLOPENTYLIDENE-PROPAN-2-ONE
スピロ[4.5]デカン-7,9-ジオンシクロペンタノン
9,10-ジヒドロ-4H-ベンゾ[4,5]シクロヘプタ[1,2-B]チオフェン-4-オン (90%)
4,4'-ビス(2-スルホナトスチリル)ビフェニル二ナトリウム
ホスカルネットナトリウム
2-メチルシクロプロパンカルボン酸
7-メチル-1,6-オクタジエン
N-(2-Methylpropylidene)-butylamine
2-(b-(2-Thienyl)vinyl)benzoicacid
2-(2,3-DIHYDRO-1-BENZENESULFONYL-PYRROLO[2,3-B]PYRIDIN-3-YL)ACETONITRILE
Optical Brighter FP127
2-テニルホスホン酸ジエチル
プロピルホスホン酸無水物
3,7-ジメチル-2,6-オクタジエン酸