JPS6381132A - Hydrolyzing method for alkoxysilane - Google Patents
Hydrolyzing method for alkoxysilaneInfo
- Publication number
- JPS6381132A JPS6381132A JP22519987A JP22519987A JPS6381132A JP S6381132 A JPS6381132 A JP S6381132A JP 22519987 A JP22519987 A JP 22519987A JP 22519987 A JP22519987 A JP 22519987A JP S6381132 A JPS6381132 A JP S6381132A
- Authority
- JP
- Japan
- Prior art keywords
- alcohol
- water
- alkoxysilane
- halogenating agent
- group
- 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
- 230000003301 hydrolyzing effect Effects 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- 230000002140 halogenating effect Effects 0.000 claims abstract description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 7
- 150000003509 tertiary alcohols Chemical class 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 5
- 230000007062 hydrolysis Effects 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- -1 organic acid halide Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- ZVJXKUWNRVOUTI-UHFFFAOYSA-N ethoxy(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OCC)C1=CC=CC=C1 ZVJXKUWNRVOUTI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- FBGNFSBDYRZOSE-UHFFFAOYSA-N tris(ethenyl)-ethoxysilane Chemical compound CCO[Si](C=C)(C=C)C=C FBGNFSBDYRZOSE-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、アルフキジシランを直接水を加えることなく
加水分解してシロキサンを製造する方法に関するもので
ある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing siloxane by hydrolyzing alfukidisilane without directly adding water.
最近ケイ素化合物は、電子部品、特にエレクトロニクス
関係の部品を製造する材料として広く利。Recently, silicon compounds have been widely used as materials for manufacturing electronic parts, especially electronics-related parts.
用されている。これらの材料は、例えばハロゲン化シラ
ンを水の存在下で加水分解して５１−Ｃｍ結合を５ｉ−
ＯＲに変えることによって製造されているが、このよう
に水を用いた加水分解では品質にバラツキを生じ、精密
な電子部品に適合する良質の加水分解物を得ることが困
難である。It is used. These materials are produced by, for example, hydrolyzing halogenated silane in the presence of water to convert 51-Cm bonds into 5i-
However, such hydrolysis using water causes variations in quality, making it difficult to obtain a high-quality hydrolyzate suitable for precision electronic parts.
本発明者らは、アルコキシシランの加水分解について種
々検討した結果、水を用いずに、ある種のアルコール又
はアルコールと有機カルボン酸とハロゲン化剤とを反応
させ、この際生じる水を利用すれば、均一な状態で加水
分解が進行することを見出し、本発明をなすに至った。As a result of various studies on the hydrolysis of alkoxysilanes, the present inventors found that if a certain type of alcohol or an alcohol is reacted with an organic carboxylic acid and a halogenating agent without using water, and the water produced at this time is used. It was discovered that hydrolysis proceeds in a uniform state, leading to the present invention.
すなわち、本発明は、一般式
％式％
（式中のＲ及びＲ′はアルキル基、アルケニル基又はア
リール基、厘は３以下の数である）で示されるアルコキ
シシランに、水の不存在下、第三級アルコールとハロゲ
ン化剤あるいはアルコールと有機カルボン酸とハロゲン
化剤とを反応させることを特徴とする前記アルコキシシ
ランの加水分解方法を提供するものである。That is, the present invention provides an alkoxysilane represented by the general formula % (in which R and R' are an alkyl group, an alkenyl group, or an aryl group, and 厘 is a number of 3 or less) in the absence of water. The present invention provides a method for hydrolyzing alkoxysilane, which comprises reacting a tertiary alcohol with a halogenating agent or an alcohol, an organic carboxylic acid, and a halogenating agent.
前記一般式（１）中のＲとＲ′とは同じでも、また異な
っていてもよく、それぞれがメチル基、エチル基、プロ
ピル基のようなアルキル基、ビニル基、プロペニル基の
ようなアルケニル基又は７エ二ル基のようなアリール基
を示す。したがって、一般式（１）のアルコキシシラン
の例としては、トリエトキシメチルシラン、トリエトキ
シフェニルシランなどのトリアルコキシシラ−ン類、ジ
ェトキシジメチルシラン、ジェトキシメチルビニルシラ
ン、ジェトキシメチルフェニルシラン、ジェトキシジビ
ニルシラン、ジェトキシビニルフェニルシラン、ジェト
キシジフェニルシランなどのジアルコキシシラン類、エ
トキシトリメチルシラン、エトキシトリビニルシラン、
エトキシトリフェニルシランなどのモノアルコキシシラ
ン類を挙げることができる。これらは単独で用いてもよ
いし、２種以上混合して用いてもよい。また、トリアル
コキシシラン類とテトラアルコキシシラン類の混合物の
ようなＯ＜ＩＩ＜１に相当するものも用いることができ
る。R and R' in the general formula (1) may be the same or different, and each represents an alkyl group such as a methyl group, an ethyl group, or a propyl group, or an alkenyl group such as a vinyl group or a propenyl group. Or it represents an aryl group such as a 7-enyl group. Therefore, examples of the alkoxysilane of general formula (1) include trialkoxysilanes such as triethoxymethylsilane and triethoxyphenylsilane, jetoxydimethylsilane, jetoxymethylvinylsilane, jetoxymethylphenylsilane, and Dialkoxysilanes such as toxydivinylsilane, jetoxyvinylphenylsilane, jetoxydiphenylsilane, ethoxytrimethylsilane, ethoxytrivinylsilane,
Monoalkoxysilanes such as ethoxytriphenylsilane can be mentioned. These may be used alone or in combination of two or more. Moreover, those corresponding to O<II<1, such as a mixture of trialkoxysilanes and tetraalkoxysilanes, can also be used.
次に、第三級アルコールとしては通常市販されている第
三級ブチルアルコーノ呟第三級アミルアルコールを用い
るのが便利である。この第三級アルコールは５ｉ−ＯＲ
’結合１モルに対して０．５モル以上あればよいが、有
利なのは０．５から１．５モルまでである。Next, as the tertiary alcohol, it is convenient to use commercially available tertiary butyl alcohol or tertiary amyl alcohol. This tertiary alcohol is 5i-OR
'The amount may be 0.5 mole or more per mole of bond, but is preferably from 0.5 to 1.5 mole.
また、ハロゲン化剤としては、アルコールと反応してハ
ロゲン化水素を発生するような化合物、例えば有機酸ハ
ライド、ハロゲン化チオニノ呟ハロゲン化カルボニルな
どが用いられる。このものの使用量は、５ｉＯＲ’結合
１モルに対し、ハロゲン化水素換算で０．５モル以上、
好ましくは０．５〜１．Ｓモルである。Further, as the halogenating agent, a compound that reacts with alcohol to generate hydrogen halide, such as an organic acid halide, a halogenated thioninol, or a halogenated carbonyl, is used. The amount of this substance used is 0.5 mol or more in terms of hydrogen halide per 1 mol of 5iOR' bond,
Preferably 0.5-1. It is S mole.
他方、有機カルボン酸と併用するアルコールは第−級又
は第二級アルコールであり、例えばメチルアルコール、
エチルアルコール、プロピルアルコールなどを挙げるこ
とができる。有機カルボン酸としては、酢酸、プロピオ
ン酸、酪酸などが用いられる。このアルコール及び有機
カルボン酸の量は、５ｉ−（ＯＲ’ ）結合１モルに対
し、０．５モル以上、好ましくは０．５〜１．ｓモルの
範囲が選ばれる。On the other hand, the alcohol used in combination with the organic carboxylic acid is a primary or secondary alcohol, such as methyl alcohol,
Examples include ethyl alcohol and propyl alcohol. As the organic carboxylic acid, acetic acid, propionic acid, butyric acid, etc. are used. The amount of alcohol and organic carboxylic acid is 0.5 mol or more, preferably 0.5 to 1.5 mol or more, per 1 mol of 5i-(OR') bond. A range of s moles is chosen.
本発明によると直接水を加えないで反応系内で生成する
水によってアルコキシシランが加水分解をされるために
加水分解反応が均一系で進行するようになり、操作が簡
便化される。また生成物も直接水と反応させる方法をと
る場合に比し異なったものとなる。例えば、メチルトリ
エトキシシランを第三級ブチルアルコールとアセチルク
ロリドを用いて加水分解すると固いゲル状加水分解物と
なり、アルコールと酢酸を用いる方法で加水分解すると
粘稠な加水分解物が得られる。According to the present invention, since the alkoxysilane is hydrolyzed by the water generated within the reaction system without directly adding water, the hydrolysis reaction proceeds in a homogeneous system, which simplifies the operation. In addition, the product is different from that obtained by directly reacting with water. For example, when methyltriethoxysilane is hydrolyzed using tertiary butyl alcohol and acetyl chloride, a hard gel-like hydrolyzate is obtained, and when hydrolyzed using alcohol and acetic acid, a viscous hydrolyzate is obtained.
次に実施例により本発明をさらに詳細に説明す実施例１
メチルトリエトキシシラン１８ｇ、第三級アルコール３
０９とトルエン３０社の溶液にアセチルクロリド１６ｇ
とトルエン３０ｄの溶液を滴下し、１夜放置後減圧下に
溶媒を留去して固いゲル状加水分解物を得た。Next, the present invention will be explained in more detail with reference to examples.Example 1: 18 g of methyltriethoxysilane, 3 g of tertiary alcohol
16g of acetyl chloride in a solution of 09 and toluene 30
A solution of 30 d of toluene was added dropwise, and after standing overnight, the solvent was distilled off under reduced pressure to obtain a hard gel-like hydrolyzate.
実施例２
メチルトリエトキシシラン１８ｇ、エチルアルコール１
ｏａ１とトルエン３０ｍ１の溶液に酢酸１２ｒＲ１１ア
セチルクロリド５ｍｌとトルエン３０ｍ１の溶液を滴下
し、１夜放置後減圧下に溶媒を留去して６．０ｇの粘稠
な樹脂状物を得た。Example 2 18 g of methyltriethoxysilane, 1 part of ethyl alcohol
A solution of 5 ml of acetic acid 12rR11 acetyl chloride and 30 ml of toluene was added dropwise to a solution of oa1 and 30 ml of toluene, and after standing overnight, the solvent was distilled off under reduced pressure to obtain 6.0 g of a viscous resinous material.
特許出願人 工業技術院長 飯塚幸三復代理人 阿
形 明Patent applicant Director of the Agency of Industrial Science and Technology Kozo Iizuka Agent A
Shape Akira
Claims (1)
リール基、ｍは３以下の数である） で示されるアルコキシシランに、水の不存在下、第三級
アルコール及びハロゲン化剤とを反応させることを特徴
とする前記アルコキシシランの加水分解方法。 ２ 一般式 Ｒ＿ｍＳｉ（ＯＲ′）＿４＿−＿ｍ （式中のＲ及びＲ′はアルキル基、アルケニル基又はア
リール基、ｍは３以下の数である） で示されるアルコキシシランに、水の不存在下、アルコ
ール、有機カルボン酸及びハロゲン化剤とを反応させる
ことを特徴とする前記アルコキシシランの加水分解方法
。[Claims] 1 An alkoxysilane represented by the general formula R_mSi(OR')_4_-_m (wherein R and R' are an alkyl group, an alkenyl group, or an aryl group, and m is a number of 3 or less) . A method for hydrolyzing alkoxysilane, which comprises reacting a tertiary alcohol and a halogenating agent in the absence of water. 2 In the absence of water, an alkoxysilane represented by the general formula R_mSi(OR')_4_-_m (R and R' in the formula are an alkyl group, an alkenyl group, or an aryl group, and m is a number of 3 or less) , an alcohol, an organic carboxylic acid, and a halogenating agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22519987A JPS6381132A (en) | 1987-09-10 | 1987-09-10 | Hydrolyzing method for alkoxysilane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22519987A JPS6381132A (en) | 1987-09-10 | 1987-09-10 | Hydrolyzing method for alkoxysilane |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11356184A Division JPS60258189A (en) | 1984-06-02 | 1984-06-02 | Hydrolysis of alkylchlorosilane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6381132A true JPS6381132A (en) | 1988-04-12 |
| JPH0217573B2 JPH0217573B2 (en) | 1990-04-20 |
Family
ID=16825526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22519987A Granted JPS6381132A (en) | 1987-09-10 | 1987-09-10 | Hydrolyzing method for alkoxysilane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6381132A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013209649A (en) * | 2012-03-16 | 2013-10-10 | Air Products & Chemicals Inc | Catalyst synthesis for organosilane sol-gel reaction |
| US9809711B2 (en) | 2012-01-17 | 2017-11-07 | Versum Materials Us, Llc | Catalyst and formulations comprising same for alkoxysilanes hydrolysis reaction in semiconductor process |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49107065A (en) * | 1973-02-12 | 1974-10-11 | ||
| JPS5038085A (en) * | 1973-08-10 | 1975-04-09 | ||
| JPS5534258A (en) * | 1978-09-01 | 1980-03-10 | Tokyo Denshi Kagaku Kabushiki | Coating solution for forming silica film |
| JPS5534276A (en) * | 1978-09-04 | 1980-03-10 | Tokyo Denshi Kagaku Kabushiki | Preparation of coating liquid for silica-based film formation |
-
1987
- 1987-09-10 JP JP22519987A patent/JPS6381132A/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49107065A (en) * | 1973-02-12 | 1974-10-11 | ||
| JPS5038085A (en) * | 1973-08-10 | 1975-04-09 | ||
| JPS5534258A (en) * | 1978-09-01 | 1980-03-10 | Tokyo Denshi Kagaku Kabushiki | Coating solution for forming silica film |
| JPS5534276A (en) * | 1978-09-04 | 1980-03-10 | Tokyo Denshi Kagaku Kabushiki | Preparation of coating liquid for silica-based film formation |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9809711B2 (en) | 2012-01-17 | 2017-11-07 | Versum Materials Us, Llc | Catalyst and formulations comprising same for alkoxysilanes hydrolysis reaction in semiconductor process |
| JP2013209649A (en) * | 2012-03-16 | 2013-10-10 | Air Products & Chemicals Inc | Catalyst synthesis for organosilane sol-gel reaction |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0217573B2 (en) | 1990-04-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |