JPH06128274A - Production of t-butyldimethylchlorosilane - Google Patents
Production of t-butyldimethylchlorosilaneInfo
- Publication number
- JPH06128274A JPH06128274A JP4302847A JP30284792A JPH06128274A JP H06128274 A JPH06128274 A JP H06128274A JP 4302847 A JP4302847 A JP 4302847A JP 30284792 A JP30284792 A JP 30284792A JP H06128274 A JPH06128274 A JP H06128274A
- Authority
- JP
- Japan
- Prior art keywords
- butyldimethylchlorosilane
- acid
- butylpentamethyldisiloxane
- reaction
- thionyl chloride
- 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.)
- Pending
Links
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 16
- KDJUMPQFOPXSMM-UHFFFAOYSA-N tert-butyl-dimethyl-trimethylsilyloxysilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C KDJUMPQFOPXSMM-UHFFFAOYSA-N 0.000 claims abstract description 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 8
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 11
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 125000006239 protecting group Chemical group 0.000 description 3
- 239000005051 trimethylchlorosilane Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000012070 reactive reagent Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はシリル化剤として有用な
ｔ−ブチルジメチルクロロシランの製造方法に関し、特
に医薬品工業の分野で廃棄されているｔ−ブチルペンタ
メチルジシロキサンを原料とするｔ−ブチルジメチルク
ロロシランの製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing t-butyldimethylchlorosilane useful as a silylating agent, and in particular, t-butyl prepared from t-butylpentamethyldisiloxane which has been discarded in the field of pharmaceutical industry. The present invention relates to a method for producing dimethylchlorosilane.
【０００２】[0002]
【従来技術】医薬品工業の分野においては、医薬（例え
ば、プロスタグランジン、チェナマイシン等）を合成す
る際の反応過程で、水酸基、カルボキシル基、アミノ基
等が有する活性水素原子を、シリル化剤と反応させるこ
とによって保護基を導入し、目的とする反応を行った後
に該保護基を加水分解（脱シリル化）することによって
もとの水酸基等にもどす方法が広く利用されている。こ
のようなシリル化剤としては、トリメチルクロロシラン
と共に、バルキーな基を有しているｔ−ブチルジメチル
クロロシランが多用されている。2. Description of the Related Art In the field of the pharmaceutical industry, active hydrogen atoms possessed by a hydroxyl group, a carboxyl group, an amino group, etc. are treated with a silylating agent in the reaction process when synthesizing a drug (eg, prostaglandin, chenamycin, etc.) A method is widely used in which a protective group is introduced by reacting with, the target reaction is performed, and then the protective group is hydrolyzed (desilylated) to restore the original hydroxyl group or the like. As such a silylating agent, t-butyldimethylchlorosilane having a bulky group is often used together with trimethylchlorosilane.
【０００３】これらの中でも、ｔ−ブチルジメチルクロ
ロシランは立体選択性が高く、且つそれによってシリル
化されたシリル化物は反応性の高い試薬に対しても比較
的安定であり、湿度の高い雰囲気中や中性の水溶液中で
も加水分解をすることがなく取扱が容易であるので、シ
リル化剤として特に優れている。また、ｔ−ブチルジメ
チルクロロシランは、これによって保護された保護基
が、強い酸性条件下や非水溶媒中では、フッ素イオンに
よって選択的に脱シリル化されるという優れた特徴を有
している。Of these, t-butyldimethylchlorosilane has a high stereoselectivity, and the silylated product silylated thereby is relatively stable even to a highly reactive reagent, and is used in an atmosphere of high humidity and It is particularly excellent as a silylating agent because it does not hydrolyze even in a neutral aqueous solution and is easy to handle. Further, t-butyldimethylchlorosilane has an excellent feature that the protective group protected thereby is selectively desilylated by fluoride ion under a strongly acidic condition or in a non-aqueous solvent.
【０００４】[0004]
【発明が解決しようとする課題】しかしながら、ｔ−ブ
チルジメチルクロロシランは高価であるので、シリル化
剤としてトリメチルクロロシランと共に使用されること
が多く、目的とする反応が終了した後にはｔ−ブチルペ
ンタメチルジシロキサンとして廃棄されている。そこ
で、このように廃棄されるｔ−ブチルペンタメチルジシ
ロキサンを原料として有効に利用し、ｔ−ブチルジメチ
ルクロロシランを安価に製造（回収）することが強く望
まれている。従って本発明の目的は、ｔ−ブチルペンタ
メチルジシロキサンを原料としてｔ−ブチルジメチルク
ロロシランを安価に製造する方法を提供することにあ
る。However, since t-butyldimethylchlorosilane is expensive, it is often used together with trimethylchlorosilane as a silylating agent, and t-butylpentamethyl after completion of the desired reaction. Abandoned as disiloxane. Therefore, it is strongly desired that t-butylpentamethyldisiloxane thus discarded is effectively used as a raw material to produce (recover) t-butyldimethylchlorosilane at low cost. Therefore, an object of the present invention is to provide a method for inexpensively producing t-butyldimethylchlorosilane from t-butylpentamethyldisiloxane as a raw material.
【０００５】[0005]
【課題を解決するための手段】本発明の上記の目的は、
ｔ−ブチルペンタメチルジシロキサンを塩化チオニルと
反応させてｔ−ブチルジメチルクロロシランに変換する
方法であって、前記反応の際に、メタンスルホン酸、ト
リフロロメタンスルホン酸、硫酸及び燐酸からなる群の
中から選択される少なくとも１種の化合物を存在させる
ことを特徴とする、ｔ−ブチルジメチルクロロシランの
製造方法によって達成された。The above objects of the present invention are as follows.
A method for converting t-butylpentamethyldisiloxane into th-butyldimethylchlorosilane by reacting it with thionyl chloride, wherein in the reaction, methanesulfonic acid, trifluoromethanesulfonic acid, sulfuric acid and phosphoric acid are selected. It was achieved by a process for the preparation of t-butyldimethylchlorosilane, characterized in that at least one compound selected from among them is present.
【０００６】ｔ−ブチルペンタメチルジシロキサンを塩
化チオニルと反応させｔ−ブチルジメチルクロロシラン
に変換することは、下記化１で表される反応式に従って
行わせることができる。The reaction of t-butylpentamethyldisiloxane with thionyl chloride to convert it into t-butyldimethylchlorosilane can be carried out according to the reaction formula represented by the following chemical formula 1.
【化１】 [Chemical 1]
【０００７】この反応の場合、二酸化イオウが副生して
ガスとして反応系外に出ていくので、該ガスの発生が停
止したときに反応が終了したことが分かる。塩化チオニ
ルは、ｔ−ブチルペンタメチルジシロキサンに対して１
〜２当量使用することが好ましい。用いる酸（メタンス
ルホン酸、トリフロロメタンスルホン酸、硫酸及び燐
酸）の量は、反応させるｔ−ブチルペンタメチルジシロ
キサン及び塩化チオニルの全量に対して１〜２０重量％
であることが好ましく、特に５〜１５重量％であること
が好ましい。In the case of this reaction, since sulfur dioxide is by-produced and goes out of the reaction system as a gas, it can be seen that the reaction is completed when the generation of the gas is stopped. Thionyl chloride is 1 for t-butylpentamethyldisiloxane.
It is preferred to use ~ 2 equivalents. The amount of acid (methanesulfonic acid, trifluoromethanesulfonic acid, sulfuric acid and phosphoric acid) used is 1 to 20% by weight based on the total amount of t-butylpentamethyldisiloxane and thionyl chloride to be reacted.
Is preferable, and particularly preferably 5 to 15% by weight.
【０００８】反応は、４０〜１５０℃の範囲、特に８５
〜１２５℃の範囲で行わせることが好ましい。上記反応
は、必要に応じて、溶媒中で行わせても良い。上記の溶
媒としては、ジクロロメタン、クロロホルム、四塩化炭
素、ジクロロエタン等の塩素化炭化水素溶媒、ベンゼ
ン、トルエン、キシレン等の芳香族炭化水素溶媒、ヘキ
サン等の脂肪族炭化水素溶媒等が挙げられる。以上のよ
うにして得られた反応生成液から、副生したトリメチル
クロロシラン、未反応の塩化チオニル及び溶媒を留去
し、得られた残留物を更に分留することによって、ｔ−
ブチルジメチルクロロシランを約８０％の収率で得るこ
とができる。The reaction is carried out in the range of 40 to 150 ° C., especially 85
It is preferable to carry out the treatment in the range of to 125 ° C. The above reaction may be carried out in a solvent, if necessary. Examples of the solvent include chlorinated hydrocarbon solvents such as dichloromethane, chloroform, carbon tetrachloride and dichloroethane, aromatic hydrocarbon solvents such as benzene, toluene and xylene, and aliphatic hydrocarbon solvents such as hexane. From the reaction product solution obtained as described above, the by-produced trimethylchlorosilane, unreacted thionyl chloride and the solvent were distilled off, and the resulting residue was further fractionally distilled to obtain t-
Butyldimethylchlorosilane can be obtained in a yield of about 80%.
【０００９】[0009]
【発明の効果】本発明の製造方法によれば、従来廃棄さ
れていたｔ−ブチルペンタメチルジシロキサンを原料と
して、高価なｔ−ブチルジメチルクロロシランを効率良
く製造することができるので、極めて経済的にｔ−ブチ
ルジメチルクロロシランを製造することができる。According to the production method of the present invention, expensive t-butyldimethylchlorosilane can be efficiently produced from conventionally discarded t-butylpentamethyldisiloxane as a raw material, which is extremely economical. In addition, t-butyldimethylchlorosilane can be produced.
【００１０】[0010]
【実施例】以下、本発明を実施例に従って更に詳述する
が、本発明はこれによって限定されるものではない。EXAMPLES The present invention will be described in more detail below with reference to Examples, but the present invention is not limited thereto.
【００１１】実施例１．攪拌機、滴下ロート、冷却機及
び温度計を備えた２００ｍｌの四つ口フラスコに、ｔ−
ブチルペンタメチルジシロキサン５１．１ｇ（０．２５
モル）及び塩化チオニル４１．６ｇ（０．３５モル）を
仕込み、攪拌しながら、加熱して９０℃とし、１時間掛
けてトリフロロメタンスルホン酸１３．９ｇを滴下した
後、２時間熟成させた。得られた反応生成液を減圧下で
粗蒸留して、粗ｔ−ブチルジメチルクロロシランを得
た。更に、該粗ｔ−ブチルジメチルクロロシランを精留
して、８２％の収率でｔ−ブチルジメチルクロロシラン
３０．９ｇ（０．２１モル）を得た。結果は表１に纏め
た。Embodiment 1. In a 200 ml four-necked flask equipped with a stirrer, a dropping funnel, a cooler and a thermometer, t-
Butyl pentamethyldisiloxane 51.1 g (0.25
Mol) and 41.6 g (0.35 mol) of thionyl chloride were added and heated to 90 ° C. with stirring, and 13.9 g of trifluoromethanesulfonic acid was added dropwise over 1 hour, followed by aging for 2 hours. . The obtained reaction product liquid was roughly distilled under reduced pressure to obtain crude t-butyldimethylchlorosilane. Further, the crude t-butyldimethylchlorosilane was rectified to obtain 30.9 g (0.21 mol) of t-butyldimethylchlorosilane with a yield of 82%. The results are summarized in Table 1.
【００１２】実施例２〜４．実施例１で用いたトリフロ
ロメタンスルホン酸に代えて表１に示した酸を用いた他
は、実施例１と全く同様にしてｔ−ブチルジメチルクロ
ロシランを得た。結果は表１に示した通りである。 比較例１〜３．実施例１で用いたトリフロロメタンスル
ホン酸に代えて表１に示した酸を用いた他は、実施例１
と全く同様にしてｔ−ブチルジメチルクロロシランを得
た。結果は表１に示した通りである。Examples 2-4. T-Butyldimethylchlorosilane was obtained in exactly the same manner as in Example 1 except that the acid shown in Table 1 was used instead of the trifluoromethanesulfonic acid used in Example 1. The results are as shown in Table 1. Comparative Examples 1-3. Example 1 except that the acid shown in Table 1 was used instead of the trifluoromethanesulfonic acid used in Example 1.
T-Butyldimethylchlorosilane was obtained in exactly the same manner as. The results are as shown in Table 1.
【００１３】[0013]
【表１】 [Table 1]
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 // Ｃ０７Ｂ 61/00 ３００ (72)発明者 槻岡 一正 群馬県安中市磯部２−13−１ 信越化学工 業株式会社磯部工場内─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification number Reference number within the agency FI Technical display location // C07B 61/00 300 (72) Inventor Kazumasa Tsukioka 2-13 Isobe, Gunma Prefecture Annaka City -1 Inside the Isobe factory of Shin-Etsu Chemical Co., Ltd.
Claims (1)
化チオニルと反応させてｔ−ブチルジメチルクロロシラ
ンに変換する方法であって、前記反応の際に、メタンス
ルホン酸、トリフロロメタンスルホン酸、硫酸及び燐酸
からなる群の中から選択される少なくとも１種の化合物
を存在させることを特徴とする、ｔ−ブチルジメチルク
ロロシランの製造方法。1. A method of reacting t-butylpentamethyldisiloxane with thionyl chloride to convert it to t-butyldimethylchlorosilane, which comprises reacting methanesulfonic acid, trifluoromethanesulfonic acid, sulfuric acid and A method for producing t-butyldimethylchlorosilane, characterized in that at least one compound selected from the group consisting of phosphoric acid is present.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4302847A JPH06128274A (en) | 1992-10-14 | 1992-10-14 | Production of t-butyldimethylchlorosilane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4302847A JPH06128274A (en) | 1992-10-14 | 1992-10-14 | Production of t-butyldimethylchlorosilane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06128274A true JPH06128274A (en) | 1994-05-10 |
Family
ID=17913817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4302847A Pending JPH06128274A (en) | 1992-10-14 | 1992-10-14 | Production of t-butyldimethylchlorosilane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06128274A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115010746A (en) * | 2022-07-20 | 2022-09-06 | 江苏八巨药业有限公司 | Preparation method of tert-butyldimethylsilyl chloride |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6210095A (en) * | 1985-07-05 | 1987-01-19 | Shin Etsu Chem Co Ltd | Method of recovering tert-butyldimethylchloro silane |
-
1992
- 1992-10-14 JP JP4302847A patent/JPH06128274A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6210095A (en) * | 1985-07-05 | 1987-01-19 | Shin Etsu Chem Co Ltd | Method of recovering tert-butyldimethylchloro silane |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115010746A (en) * | 2022-07-20 | 2022-09-06 | 江苏八巨药业有限公司 | Preparation method of tert-butyldimethylsilyl chloride |
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