JPH04154792A - Purification of alkylhalogenophosphonyl - Google Patents
Purification of alkylhalogenophosphonylInfo
- Publication number
- JPH04154792A JPH04154792A JP27919890A JP27919890A JPH04154792A JP H04154792 A JPH04154792 A JP H04154792A JP 27919890 A JP27919890 A JP 27919890A JP 27919890 A JP27919890 A JP 27919890A JP H04154792 A JPH04154792 A JP H04154792A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- boiling point
- alkylhalogenophosphonyl
- high boiling
- ether
- 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
- 238000000746 purification Methods 0.000 title description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000002904 solvent Substances 0.000 claims abstract description 44
- 238000009835 boiling Methods 0.000 claims abstract description 28
- 239000012535 impurity Substances 0.000 claims abstract description 12
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 11
- 150000001350 alkyl halides Chemical class 0.000 abstract description 8
- 125000005499 phosphonyl group Chemical group 0.000 abstract 2
- 238000004821 distillation Methods 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- -1 alkyl phosphine Chemical compound 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 101150084763 RPH1 gene Proteins 0.000 description 2
- 101100408281 Schizosaccharomyces pombe (strain 972 / ATCC 24843) pfh1 gene Proteins 0.000 description 2
- 101100517294 Yarrowia lipolytica (strain CLIB 122 / E 150) NTF2 gene Proteins 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol Cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 UOACKFBJUYNSLK-XRKIENNPSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002109 crystal growth method Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002488 metal-organic chemical vapour deposition Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、アルキルハロゲノホスホニルの精製方法に関
する０本発明は特に、 ＭＯＣＶＤ（Ｍｅｔａｌｏｒｇ
ａ−ｎｉｃ Ｃｈｅｍｉｃａｌ Ｖａｐｏｒ Ｄｅｐｏ
ｓｉｔｉｏｎｌ用の高純度アルキルホスフィンの合成原
料に適する高純度アルキルハロゲノホスホニルの精製方
法に関する。Detailed Description of the Invention [Industrial Application Field] The present invention relates to a method for purifying alkylhalogenophosphonyl.
a-nic Chemical Vapor Depo
The present invention relates to a method for purifying high-purity alkylhalogenophosphonyl suitable as a raw material for the synthesis of high-purity alkylphosphine for site use.
［従来の技術］
インジウム−リンをはじめとするＩＩＩ族−Ｖ族化合物
半導体薄膜の形成方法として、ＭＯＣＶＤあるいは Ｍ
ＯＭＢＥｆｕｅｔａｌｏｒｇａｎｉｃ Ｍｏ１ｅｃｕ
ｌａｒ Ｆｌｅａｓ Ｅｐｉｌ、ａｘｙｌは納品成
長系内を高真空に保つ必要がなく原料の交換が容易であ
り、メンテナンスが楽であるため、使用頻度の高まりと
ともに注目されつつある結晶成長法である。[Prior Art] MOCVD or M
OMBE fueta organic Mo1ecu
LAR Fleas Epil and Axyl are crystal growth methods that are attracting attention as their frequency of use increases, as there is no need to maintain a high vacuum in the delivery growth system, raw materials can be easily replaced, and maintenance is easy.
近年、これらの方法において使用されるリン原料として
、ホスフィンに代わってアルキルホスフィンＲＰＨ１（
ここでＲはアルキル基を示す）が提案されているが、該
用途用のアルキルホスフィンにはきわめて高純度のもの
が必要である。このため該アルキルホスフィン製造のた
めの出発原料としてのアルキルハロゲノホスホニルにも
不純物を含まない高純度のものを用いることが必須であ
る。しかしながらアルキルハロゲノホスホニルにはその
合成過程で用いられるハロゲン化アルキルやエーテルが
不純物として存在し、そのままではアルキルホスフィン
原料としては使用できず、これら不純物の除去が必要で
ある。In recent years, alkylphosphine RPH1 (RPH1) has replaced phosphine as the phosphorus raw material used in these methods.
Here, R represents an alkyl group) has been proposed, but the alkyl phosphine for this purpose needs to be of extremely high purity. Therefore, it is essential to use a highly pure alkylhalogenophosphonyl containing no impurities as a starting material for producing the alkylphosphine. However, alkylhalogenophosphonyl contains alkyl halides and ethers used in its synthesis process as impurities, and cannot be used as an alkylphosphine raw material as is, and these impurities must be removed.
さらにこれら不純物は、アルキルハロゲノホスホニルと
相互作用するため、これらを除去するには多くの工程を
必要とし、精製に時間がかかり。Furthermore, since these impurities interact with alkylhalogenophosphonyl, many steps are required to remove them, and purification takes time.
あるいは通常の除去操作では完全に除去するのが困難な
ため、高純度アルキルホスフィン製造用原料としては純
度が満足すべきものとならないという問題があった６
［発明が解決しようとする課題］
本発明の目的はアルキルホスフィンの合成中間体として
汎用されているアルキルハロゲノホスホニルの製造の際
混入するエーテル、ハロゲン化アルキル等を簡単な方法
で除去し、有機不純物の混入がない高純度のアルキルハ
ロゲノホスホニルを得ることにある。Alternatively, since it is difficult to completely remove it by normal removal operations, there is a problem that the purity is not satisfactory as a raw material for producing high-purity alkyl phosphine.6 [Problems to be Solved by the Invention] The present invention The purpose is to use a simple method to remove ethers, alkyl halides, etc. that are mixed in during the production of alkyl halogenophosphonyl, which is commonly used as an intermediate in the synthesis of alkyl phosphines, and to produce highly pure alkyl halogenophosphonyl free from organic impurities. It's about getting.
［課題を解決するための手段１
本発明の発明者らは、アルキルハロゲノホスホニル中に
混入しているエーテル、ハロゲン化アルキル等を除去す
るために、高沸点溶媒あるいは高沸点溶媒を含有する溶
媒を添加した後、これを留去すれば、これらエーテル、
ハロゲン化アルキルが有効に除去され、不純物が苫しく
低減された高純度のアルキルハロゲノホスボニルが得ら
れることを見出し本発明に至った。[Means for Solving the Problems 1] The inventors of the present invention developed a high-boiling point solvent or a solvent containing a high-boiling point solvent in order to remove ether, alkyl halide, etc. mixed in alkylhalogenophosphonyl. If this is distilled off after adding, these ethers,
The inventors have discovered that alkyl halides can be effectively removed and highly pure alkylhalogenophosbonyl with significantly reduced impurities can be obtained, leading to the present invention.
すなわち本発明は、
アルキルハロゲノホスホニルに、高沸点溶媒あるいは高
沸点溶媒を含有する溶媒を添加した後、これを留去して
不純物を除去することを特徴とするアルキルハロゲノホ
スホニルの精製方法である。That is, the present invention provides a method for purifying alkylhalogenophosphonyl, which comprises adding a high-boiling point solvent or a solvent containing a high-boiling point solvent to alkylhalogenophosphonyl, and then distilling the solvent off to remove impurities. be.
なお本発明で言うアルキルハロゲノホスホニルとは次式
で表わされる化合物である。Note that the alkylhalogenophosphonyl referred to in the present invention is a compound represented by the following formula.
−Ｐ−Ｘ２
（ここに、Ｒはアルキル基を示し、好ましくは炭素数１
〜１０個のアルキル基であり、Ｘはハロゲンを示す。）
本発明で添加する高沸点溶媒の種類は、除去すべき化合
物の種類にもよるが、精製効果を大きくするためには、
ハロゲン化アルキルとの分離が可能な限り高くすること
が望ましく、具体的には沸点が１００℃以上の脂肪族エ
ーテルが望ましい。-P-X2 (here, R represents an alkyl group, preferably having 1 carbon number
~10 alkyl groups, and X represents halogen. ) The type of high boiling point solvent added in the present invention depends on the type of compound to be removed, but in order to increase the purification effect,
It is desirable that the separation from the alkyl halide be as high as possible, and specifically an aliphatic ether with a boiling point of 100° C. or higher is desirable.
またアルキルハロゲノホスホニル中に混入しても問題が
ない溶媒を用いることが望ましい。このような脂肪族エ
ーテルとしては例えば、ジブチルエーテル、ジイソペン
チルエーテル、アニソール、フエネトール等を例示する
ことができる。Further, it is desirable to use a solvent that does not cause any problem even if mixed into the alkylhalogenophosphonyl. Examples of such aliphatic ethers include dibutyl ether, diisopentyl ether, anisole, and phenethole.
本発明においては、精製すべきアルキルハロゲノホスホ
ニルに、前記高沸点溶媒のみを添加し、これを留去する
方法でも精製効果は十分に発揮されるが、高沸点溶媒の
みでは留去操作に時間を要する。このため前記高沸点溶
媒に対して、それよりも低沸５占の溶媒を添加した混合
溶媒として用いるのが一層好ましい、このような低沸点
の溶媒としてはジエチルエーテル、テトラヒドロフラン
（ＴＨＦ）、ｎ−ヘキサンなどを例示することができる
が、特にジエチルエーテルが好ましい、ジエチルエーテ
ルを不純物として含有するアルキルハロゲノホスホニル
からジエチルエーテルを除去、精製する場合においても
、ジエチルエーテルの添加は留去速度促進のためには有
効であり、除去すべき成分であるジエチルエーテルを積
極的に添加することによって精製効果がかえって促進さ
れるという予想外の現象が見出された。ここで、高沸点
溶媒に対して混合するジエチルエーテルは容量比で１．
２〜２０、好ましくは１５〜１０である。In the present invention, a method in which only the high-boiling point solvent is added to the alkylhalogenophosphonyl to be purified and distilled off can also achieve a sufficient purification effect, but if only the high-boiling point solvent is used, the distillation operation takes time. It takes. Therefore, it is more preferable to use a mixed solvent in which a lower boiling point solvent is added to the high boiling point solvent. Examples of such low boiling point solvents include diethyl ether, tetrahydrofuran (THF), n- Examples include hexane, but diethyl ether is particularly preferred. Even when removing and purifying diethyl ether from alkylhalogenophosphonyl containing diethyl ether as an impurity, diethyl ether is added to accelerate the rate of distillation. An unexpected phenomenon has been discovered in which the purification effect is actually accelerated by actively adding diethyl ether, which is a component to be removed. Here, the volume ratio of diethyl ether to be mixed with the high boiling point solvent is 1.
2-20, preferably 15-10.
高沸点溶媒あるいは高沸点溶媒を含有する溶媒の添加量
は特に限定されないが、除去すべきエーテル、ハロゲン
化アルキルに対し、容量比で１００〜２０００倍が望ま
しい、添加量がこれよりも少ないと精製効果が不十分と
なり、また多すぎると添加した溶媒の留去に時間を要す
る。The amount of the high boiling point solvent or solvent containing the high boiling point solvent added is not particularly limited, but it is preferably 100 to 2000 times the volume of the ether or alkyl halide to be removed. The effect will be insufficient, and if the amount is too high, it will take time to distill off the added solvent.
［実施例］
以下実施例により本発明方法を具体的に説明する。なお
実施例および比較例におけるｔｅｒＬ−ブチルジクロＮ
ロホスホニル中の有機不純物の定量は、ｔｅｒｔ−ブチ
ルジクロロホスホニルをトルエンに溶解さセ、ガスクロ
マトグラフ法により測定した。[Example] The method of the present invention will be specifically explained below using Examples. In addition, terL-butyldichloroN in Examples and Comparative Examples
The organic impurities in lophosphonyl were determined by gas chromatography using tert-butyldichlorophosphonyl dissolved in toluene.
実」〔例」４
ジエチルエーテルｌ０３８ｐｐｓ＋ 、 ｔｅｒｔ−ブ
チルクロライド６４７ ｐｐｍが混入しているｔｅｒｔ
−ブチルジクロロホスホニル４７０ｇに、ジブチルエー
テル３００ｍ１を添加し、フラスコ底部を７０℃、蒸留
塔をリボンヒーター７０℃に加熱し２０ ＋１１＋＊ｌ
１ｇで添加溶媒を留去した。この溶媒の留去には９時間
を要した。その後型に、フラスコ底部を８０℃、蒸留塔
をリボンヒーターで８０℃に加熱し５＊ｍｔ１ｇで６時
間蒸留した。こうして得られた白色固体中のジエチルエ
ーテルは２５ ｐｐｌ＋以下、ｔｅｒｔ−ブチルクロラ
イドは２５ ｐｐＨ以下であった。[Example] 4 Tert containing 1038 pps+ of diethyl ether and 647 ppm of tert-butyl chloride
- Add 300 ml of dibutyl ether to 470 g of butyldichlorophosphonyl, heat the bottom of the flask to 70°C and the distillation column to 70°C with a ribbon heater to give 20 +11+*l
The added solvent was distilled off after 1 g. It took 9 hours to distill off this solvent. Thereafter, the bottom of the flask was heated to 80° C. and the distillation column was heated to 80° C. with a ribbon heater, and distillation was carried out at 1 g of 5*mt for 6 hours. Diethyl ether and tert-butyl chloride in the white solid thus obtained were below 25 ppl+ and below 25 ppH.
実ｍ
実施例１と同じ組成のｔｅｒＬ−ブチルジクロロホスホ
ニル４７０ｇに、ジブチルエーテル１００ｍ１、ジエチ
ルエーテル３００ｍ１を添加した後、実施例１と同じ条
件で溶媒留去、蒸留を行なった。溶媒の留去に要した時
間は３時間と短縮された６昇温、減圧して蒸留を６時間
行なった後に（１１られた白色固体中の不純物はジエヂ
ルエーデル、ｔ、ｃｒｔ−ブヂルクロライドともに２５
ｐｐ−以下であった。After adding 100 ml of dibutyl ether and 300 ml of diethyl ether to 470 g of terL-butyldichlorophosphonyl having the same composition as in Example 1, the solvent was distilled off and distilled under the same conditions as in Example 1. The time required for distilling off the solvent was shortened to 3 hours.6 After distillation was carried out for 6 hours at elevated temperature and reduced pressure (11), the impurities in the white solid obtained were 25.
It was less than pp-.
Ｌ較亘ニ
ジエチルエーテル４９９ ｐｐｍ 、 ＬｅｒＬ−ブチ
ルクロライド３６０ ｐｐｍが混入しているｔｅｒｔ−
ブチルジクロロホスホニル４５０ｇに溶媒を添加せずに
、他は実施例１と同様な操作を行った。７０℃、 ２０
ｍｍＨｇで６時間、及び８０℃、５ｆｆｌＩＩＩＩ４
ｇで６時間蒸留を行なった。得られた白色固体中のジエ
チルエーテルは１５２ ｐｐｍ 、 ＬｅｒＬ−ブチル
クロライド３０３ ｐｐｍで、両者ともほとんど低減さ
れていなかった。tert- containing 499 ppm of L-diethyl ether and 360 ppm of L-butyl chloride.
The same operation as in Example 1 was carried out except that no solvent was added to 450 g of butyl dichlorophosphonyl. 70℃, 20
6 hours at mmHg and 80°C, 5fflIII4
Distillation was carried out at g for 6 hours. Diethyl ether in the obtained white solid was 152 ppm, and LerL-butyl chloride was 303 ppm, both of which were hardly reduced.
［発明の効果］
本発明によれば、アルキルハロゲノホスボニルに、高沸
点溶媒あるいは高沸点溶媒を含イー１する溶媒を添加し
これを留去することにより、！ｎに蒸留操作では除去困
難であったアルキルハロゲノホスホニル中に混入したエ
ーテルおよびハロゲン化アルキルを、簡単な操作でしか
も効率的に除去することができ、半導体薄膜製造用高純
度アルキルホスフィンの合成原料に適する高純度アルキ
ルハロゲノホスホニルが得られる。[Effects of the Invention] According to the present invention, by adding a high boiling point solvent or a solvent containing a high boiling point solvent to the alkyl halogenophosphonyl and distilling it off,! Ethers and alkyl halides mixed in alkylhalogenophosphonyl, which were difficult to remove by distillation, can be removed easily and efficiently, making it a raw material for the synthesis of high-purity alkylphosphine for semiconductor thin film production. High purity alkylhalogenophosphonyl suitable for
Claims (3)
いは高沸点溶媒を含有する溶媒を添加した後、これを留
去して不純物を除去することを特徴とするアルキルハロ
ゲノホスホニルの精製方法。(1) A method for purifying alkylhalogenophosphonyl, which comprises adding a high-boiling point solvent or a solvent containing a high-boiling point solvent to alkylhalogenophosphonyl, and then distilling the solvent off to remove impurities.
部とジエチルエーテル２〜２０容量部との混合物である
ことを特徴とする請求項１記載のアルキルハロゲノホス
ホニルの精製方法。(2) The method for purifying alkylhalogenophosphonyl according to claim 1, wherein the solvent containing a high-boiling point solvent is a mixture of 1 part by volume of a high-boiling point solvent and 2 to 20 parts by volume of diethyl ether.
エーテルであることを特徴とする請求項１又は２記載の
アルキルハロゲノホスホニルの精製方法。(3) The method for purifying alkylhalogenophosphonyl according to claim 1 or 2, wherein the high boiling point solvent is an aliphatic ether having a boiling point of 100°C or higher.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27919890A JP2809859B2 (en) | 1990-10-19 | 1990-10-19 | Purification method of alkylhalogenophosphonyl |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27919890A JP2809859B2 (en) | 1990-10-19 | 1990-10-19 | Purification method of alkylhalogenophosphonyl |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04154792A true JPH04154792A (en) | 1992-05-27 |
| JP2809859B2 JP2809859B2 (en) | 1998-10-15 |
Family
ID=17607802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27919890A Expired - Fee Related JP2809859B2 (en) | 1990-10-19 | 1990-10-19 | Purification method of alkylhalogenophosphonyl |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2809859B2 (en) |
-
1990
- 1990-10-19 JP JP27919890A patent/JP2809859B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2809859B2 (en) | 1998-10-15 |
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