JPH0217573B2 - - Google Patents
Info
- Publication number
- JPH0217573B2 JPH0217573B2 JP62225199A JP22519987A JPH0217573B2 JP H0217573 B2 JPH0217573 B2 JP H0217573B2 JP 62225199 A JP62225199 A JP 62225199A JP 22519987 A JP22519987 A JP 22519987A JP H0217573 B2 JPH0217573 B2 JP H0217573B2
- Authority
- JP
- Japan
- Prior art keywords
- alcohol
- group
- alkoxysilane
- water
- organic
- 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.)
- Expired - Lifetime
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- -1 organic acid halide Chemical class 0.000 claims description 4
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 125000000075 primary alcohol group Chemical group 0.000 claims description 3
- 150000003333 secondary alcohols Chemical class 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 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
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-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
- 230000007062 hydrolysis Effects 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 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 2
- 239000002904 solvent Substances 0.000 description 2
- MLEJMZWVOLYZIP-UHFFFAOYSA-N 2,2-diethoxyethenyl(phenyl)silane Chemical compound C(C)OC(=C[SiH2]C1=CC=CC=C1)OCC MLEJMZWVOLYZIP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 description 1
- MNFGEHQPOWJJBH-UHFFFAOYSA-N diethoxy-methyl-phenylsilane Chemical compound CCO[Si](C)(OCC)C1=CC=CC=C1 MNFGEHQPOWJJBH-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 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
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 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
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
Description
【発明の詳細な説明】
本発明は、アルコキシ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 an alkoxysilane 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
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Si―Cl結合
をSi―OHに変えることによつて製造されている
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。 Recently, silicon compounds have been widely used as materials for manufacturing electronic components, especially electronics-related components. These materials are manufactured by, for example, hydrolyzing halogenated silanes in the presence of water to change Si-Cl bonds to Si-OH, but this hydrolysis with water may result in poor quality. It is 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、本発明をなすに至つた。 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. They discovered that hydrolysis progresses in a uniform manner, leading to the present invention.
すなわち、本発明は、一般式
RnSi（OR′）4-n …(1)
（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、
第三級アルコールと有機ハライドあるいは第一級
又は第二級アルコールと有機カルボン酸と有機酸
ハライド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 a compound with the general formula R n Si(OR') 4-n (1) (wherein R and R' are an alkyl group, an alkenyl group, or an aryl group, and m is a number of 3 or less). In the absence of water, the indicated alkoxysilane
The present invention provides a method for hydrolyzing alkoxysilane, which comprises reacting a tertiary alcohol and an organic halide, or a primary or secondary alcohol, an organic carboxylic acid, and an organic acid halide.
前記一般式(1)中のＲとR′とは同じでも、また
異なつていてもよく、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フエ
ニル基のようなアリール基を示す。したがつて、
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、トリエトキシフエニルシ
ランなどのトリアルコキシシラン類、ジエトキシ
ジメチルシラン、ジエトキシメチルビニルシラ
ン、ジエトキシメチルフエニルシラン、ジエトキ
シジビニルシラン、ジエトキシビニルフエニルシ
ラン、ジエトキシジフエ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、エトキシトリフエニル
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０＜ｍ＜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 an aryl group such as a phenyl group. Therefore,
Examples of the alkoxysilane of general formula (1) include trialkoxysilanes such as triethoxymethylsilane and triethoxyphenylsilane, diethoxydimethylsilane, diethoxymethylvinylsilane, diethoxymethylphenylsilane, and diethoxydimethylsilane. Examples include dialkoxysilanes such as vinylsilane, diethoxyvinylphenylsilane, and diethoxydiphenylsilane, and monoalkoxysilanes such as ethoxytrimethylsilane, ethoxytrivinylsilane, and ethoxytriphenylsilane. These may be used alone, or two
More than one species may be mixed and used. Moreover, those corresponding to 0<m<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ル、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Si―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 and tertiary amyl alcohol. The tertiary alcohol may be present in an amount of 0.5 mole or more per mole of Si--OR' bond, but preferably from 0.5 to 1.5 mole.
また、有機酸ハライドとしては、酢酸、プロピ
オン酸、酪酸のような有機酸のクロリド、ブロミ
ドなどが用いられる。このものの使用量は、
SiOR′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0.5〜1.5モルである。 Further, as the organic acid halide, chloride, bromide, etc. of organic acids such as acetic acid, propionic acid, and butyric acid are used. The amount used for this is
For 1 mole of SiOR′ bond, in terms of hydrogen halide
The amount is 0.5 mol or more, preferably 0.5 to 1.5 mol.
他方、有機カルボン酸と併用するアルコールは
第一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、Si―（OR′）結合１ルに対し、0.5モル以
上、好ましくは0.5〜1.5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, ethyl alcohol, propyl alcohol, and the like. As the organic carboxylic acid, acetic acid, propionic acid, butyric acid, etc. are used. The amount of alcohol and organic carboxylic acid is selected to be 0.5 mol or more, preferably 0.5 to 1.5 mol, per 1 molecule of Si-(OR') bond.
本発明によると直接水を加えないで反応系内で
生成する水にとつ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つ
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
る。 Next, the present invention will be explained in more detail with reference to Examples.
実施例 １
メチルトリエトキシシラン18ｇ、第三級ブチル
アルコール30ｇとトルエン30mlの溶液にアセチル
クロリド16ｇとトルエン30mlの溶液を適下し、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。Example 1 A solution of 16 g of acetyl chloride and 30 ml of toluene was dropped into a solution of 18 g of methyltriethoxysilane, 30 g of tertiary butyl alcohol, and 30 ml of toluene, and 1
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10mlとトルエン30mlの溶液に酢酸12ml、アセ
チルクロリド５mlとトルエン30mlの溶液を適下
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 A solution of 12 ml of acetic acid, 5 ml of acetyl chloride, and 30 ml of toluene was dropped into a solution of 18 g of methyltriethoxysilane, 10 ml of ethyl alcohol, and 30 ml of toluene, and after standing overnight, the solvent was distilled off under reduced pressure to obtain 6.0 g. A viscous resinous material was obtained.
Claims (1)
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、
第三級アルコール及び有機酸ハライドとを反応さ
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 RnSi（OR′）4-n （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、
第一級又は第二級アルコール、有機カルボン酸及
び有機酸ハライド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 Alkoxy represented by the general formula R n Si(OR') 4-n (in the formula, R and R' are an alkyl group, an alkenyl group, or an aryl group, and m is a number of 3 or less) Silane, in the absence of water,
A method for hydrolyzing alkoxysilane, which comprises reacting a tertiary alcohol and an organic acid halide. 2 An alkoxysilane represented by the general formula R n Si(OR') 4-n (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) is In the presence of
A method for hydrolyzing alkoxysilane, which comprises reacting a primary or secondary alcohol, an organic carboxylic acid, and an organic acid halide.
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 JPS6381132A (en) | 1988-04-12 |
| JPH0217573B2 true 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) |
Families Citing this family (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 |
| US20130243968A1 (en) * | 2012-03-16 | 2013-09-19 | Air Products And Chemicals, Inc. | Catalyst synthesis for organosilane sol-gel reactions |
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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6381132A (en) | 1988-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |