JP2946692B2 - Method for producing 3,3-dimethyl-2-butanone - Google Patents
Method for producing 3,3-dimethyl-2-butanoneInfo
- Publication number
- JP2946692B2 JP2946692B2 JP2227269A JP22726990A JP2946692B2 JP 2946692 B2 JP2946692 B2 JP 2946692B2 JP 2227269 A JP2227269 A JP 2227269A JP 22726990 A JP22726990 A JP 22726990A JP 2946692 B2 JP2946692 B2 JP 2946692B2
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- butanone
- present
- producing
- dimethylbutane
- 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 - Fee Related
Links
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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、2,3−エポキシ−2,3−ジメチルブタンから
3,3−ジメチル−２−ブタノンを製造する方法に関する
ものである。DETAILED DESCRIPTION OF THE INVENTION INDUSTRIAL APPLICATION The present invention relates to 2,3-epoxy-2,3-dimethylbutane.
The present invention relates to a method for producing 3,3-dimethyl-2-butanone.
2,3−エポキシ−2,3−ジメチルブタンから3,3−ジメ
チル−２−ブタノンを製造する方法において、過塩素酸
水溶液を作用させる方法が報告されている（J.Am.Chem.
Soc.,102,5311（1980）他）。In a method for producing 3,3-dimethyl-2-butanone from 2,3-epoxy-2,3-dimethylbutane, a method of reacting an aqueous solution of perchloric acid has been reported (J. Am. Chem.
Soc., 102 , 5311 (1980), etc.).
しかし、この方法では3,3−ジメチル−２−ブタノン
は高々36％の低収率であり、工業上利用するには未だ不
充分であった。However, in this method, 3,3-dimethyl-2-butanone has a low yield of at most 36%, and is still insufficient for industrial use.
かかる情に鑑み、本発明者らは3,3−ジメチル−２−
ブタノンの収率向上を目的に鋭意検討を重ねた結果、特
定の触媒の存在下で反応させると2,3−エポキシ−2,3−
ジメチルブタンから3,3−ジメチル−２−ブタノンが収
率よく製造することができることを見出すとともに、さ
らに種々の検討を加え、本発明を完成するに至った。In view of such circumstances, the present inventors have found that 3,3-dimethyl-2-.
As a result of intensive studies aimed at improving the yield of butanone, it was found that when reacted in the presence of a specific catalyst, 2,3-epoxy-2,3-
The inventors have found that 3,3-dimethyl-2-butanone can be produced in good yield from dimethylbutane, and have further conducted various studies to complete the present invention.
すなわち、本発明は2,3−エポキシ−2,3−ジメチルブ
タンから3,3−ジメチル−２−ブタノンを製造する方法
において、硫酸、スルホン酸、三フッ化ホウ素錯化合
物、強酸性イオン交換樹脂の中から選ばれる触媒の存在
下に反応させることを特徴とする3,3−ジメチル−２−
ブタノンの製造方法を提供するものである。That is, the present invention relates to a method for producing 3,3-dimethyl-2-butanone from 2,3-epoxy-2,3-dimethylbutane, comprising sulfuric acid, sulfonic acid, a boron trifluoride complex compound, and a strongly acidic ion exchange resin. 3,3-dimethyl-2- characterized by reacting in the presence of a catalyst selected from
A method for producing butanone is provided.
以下、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明で用いる触媒は、硫酸、スルホン酸、三フッ化
ホウ素錯化合物、強酸性イオン交換樹脂の中から選ばれ
る触媒が挙げられる。The catalyst used in the present invention includes a catalyst selected from sulfuric acid, sulfonic acid, boron trifluoride complex compound, and a strongly acidic ion exchange resin.
本発明に用いる硫酸は、通常工業的に使用されるもの
でよく、たとえば濃度が70〜98％程度のものが好まし
い。The sulfuric acid used in the present invention may be one generally used industrially, and for example, preferably has a concentration of about 70 to 98%.
本発明に用いるスルホン酸としては、例えば、ベンゼ
ンスルホン酸、トルエンスルホン酸、メタンスルホン
酸、エタンスルホン酸、プロパンスルホン酸、ブタンス
ルホン酸等が挙げられる。Examples of the sulfonic acid used in the present invention include benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, and butanesulfonic acid.
本発明に用いる三フッ化ホウ素錯化合物としては、例
えば、三フッ化ホウ素エーテル錯化合物、三フッ化ホウ
素フェノール錯化合物、三フッ化ホウ素アルコール錯化
合物、三フッ化ホウ素酢酸錯化合物等が挙げられる。Examples of the boron trifluoride complex compound used in the present invention include a boron trifluoride etherate compound, a boron trifluoride phenol complex compound, a boron trifluoride alcohol complex compound, and a boron trifluoride acetic acid complex compound. .
本発明に用いる強酸性イオン交換樹脂としては、例え
ば、スルホン基を官能基として有するポリスチレン系イ
オン交換樹脂等が好適に用いられる。As the strongly acidic ion exchange resin used in the present invention, for example, a polystyrene ion exchange resin having a sulfone group as a functional group is preferably used.
本発明に用いる触媒の量は、2,3−エポキシ−2,3−ジ
メチルブタンに対しモル比で、通常0.05〜10であり、好
ましくは0.1〜２程度である。The amount of the catalyst used in the present invention is usually from 0.05 to 10, preferably from about 0.1 to 2, in molar ratio to 2,3-epoxy-2,3-dimethylbutane.
本発明は無溶媒でも反応は進行するが、溶媒を用いて
反応を行ってもよい。溶媒としては、反応に不活性であ
れば特に限定されるものではないが、例えば、ペンタ
ン、ヘキサン、ベンゼン、トルエン、キシレン等の炭化
水素系の溶媒が好適である。In the present invention, the reaction proceeds even without solvent, but the reaction may be performed using a solvent. The solvent is not particularly limited as long as it is inert to the reaction. For example, hydrocarbon solvents such as pentane, hexane, benzene, toluene, and xylene are suitable.
本発明の反応温度は、通常０〜100℃であり、好まし
くは５〜70℃である。The reaction temperature of the present invention is usually from 0 to 100 ° C, preferably from 5 to 70 ° C.
本発明の反応圧力は通常１気圧であるが、加・減圧下
で行っても差し支えない。The reaction pressure of the present invention is usually 1 atm, but may be carried out under increased or reduced pressure.
以上、詳述したように本発明は特定の触媒を存在させ
ることにより、2,3−エポキシ−2,3−ジメチルブタンか
ら3,3−ジメチル−２−ブタノンを高収率で製造するこ
とができる。As described in detail above, the present invention makes it possible to produce 3,3-dimethyl-2-butanone from 2,3-epoxy-2,3-dimethylbutane in high yield by the presence of a specific catalyst. it can.
以下、本発明を実施例により説明するが、本発明はこ
れら実施例によって限定されるものではない。Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited to these examples.
なお、転化率、収率は以下の式により算出した。 The conversion and the yield were calculated by the following equations.
転化率（％）＝（Ａ−Ｂ）×100/A 収 率（％）＝Ｃ×100/A ただし、 Ａ＝原料2,3−エポキシ−2,3−ジメチルブタン（mmol
e） Ｂ＝反応後、回収した2,3−エポキシ−2,3−ジメチル
ブタン（mmole） Ｃ＝生成した3,3−ジメチル−２−ブタノン（mmole） 実施例１〜７ 内容積200mlのカラム製４ツ口フラスコ内に、テフロ
ン被覆の磁石回転子を入れ、さらに表１に示す触媒とヘ
キサン10mlを入れた。Conversion (%) = (AB) × 100 / A Yield (%) = C × 100 / A where A = raw material 2,3-epoxy-2,3-dimethylbutane (mmol
e) B = 2,3-epoxy-2,3-dimethylbutane (mmole) recovered after the reaction C = 3,3-dimethyl-2-butanone (mmole) produced Examples 1-7 Column with 200 ml internal volume A Teflon-coated magnet rotor was placed in a four-necked flask made by Teflon, followed by the catalyst shown in Table 1 and 10 ml of hexane.
次に前記フラスコ内を400〜500rpmで撹拌しながら、
フラスコ内に2,3−エポキシ−2,3−ジメチルブタン16.0
gとヘキサン50gとの混合溶液を40分間かけて供給した。Next, while stirring the inside of the flask at 400 to 500 rpm,
2,3-epoxy-2,3-dimethylbutane 16.0 in a flask
A mixed solution of g and 50 g of hexane was supplied over 40 minutes.
反応温度は、表１の所定の温度になるように、内温を
コントロールした。上記混合溶液を供給した後、10分間
そのまま放置し反応を完結させた。The internal temperature was controlled so that the reaction temperature became a predetermined temperature in Table 1. After supplying the mixed solution, the mixture was allowed to stand for 10 minutes to complete the reaction.
次に、フラスコ内に水40gを冷却下に添加した後、撹
拌を止め、油層と水層を分離させた。Next, after adding 40 g of water to the flask under cooling, stirring was stopped, and an oil layer and an aqueous layer were separated.
水層をヘキサン30mlで１回抽出した。ついで油層と該
抽出ヘキサンとを混合し、ガスクロマトグラフィにより
生成物を分析した。The aqueous layer was extracted once with 30 ml of hexane. Subsequently, the oil layer and the extracted hexane were mixed, and the product was analyzed by gas chromatography.
分析した結果を表１に示す。 The results of the analysis are shown in Table 1.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０７Ｃ 45/58 Ｃ０７Ｃ 45/58 // Ｃ０７Ｂ 61/00 ３００ Ｃ０７Ｂ 61/00 ３００ (56)参考文献 特開 昭57−18643（ＪＰ，Ａ) Ｊｏｕｒｎａｌ ｏｆ ｔｈｅ Ａｍ ｅｒｉｃａｎ Ｃｈｅｍｉｃａｌ Ｓｏ ｃｉｅｔｙ（1980）102 ｐ．5311− 5316 (58)調査した分野(Int.Cl.6，ＤＢ名) ＷＰＩ／Ｌ（ＱＵＥＳＴＥＬ) ＣＡ（ＳＴＮ)────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code FI C07C 45/58 C07C 45/58 // C07B 61/00 300 C07B 61/00 300 (56) References JP-A-57-18643 ( JP, A) Journal of the American Chemical Society (1980) 102 p. 5311-5316 (58) Fields surveyed (Int. Cl. 6 , DB name) WPI / L (QUESTEL) CA (STN)
Claims (1)
3,3−ジメチル−２−ブタノンを製造する方法におい
て、硫酸、スルホン酸、三フッ化ホウ素錯化合物、強酸
性イオン交換樹脂の中から選ばれる触媒の存在下に反応
させることを特徴とする3,3−ジメチル−２−ブタノン
の製造方法。(1) From 2,3-epoxy-2,3-dimethylbutane
A method for producing 3,3-dimethyl-2-butanone, wherein the reaction is carried out in the presence of a catalyst selected from sulfuric acid, sulfonic acid, a boron trifluoride complex compound, and a strongly acidic ion exchange resin. , 3-Dimethyl-2-butanone production method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2227269A JP2946692B2 (en) | 1990-08-28 | 1990-08-28 | Method for producing 3,3-dimethyl-2-butanone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2227269A JP2946692B2 (en) | 1990-08-28 | 1990-08-28 | Method for producing 3,3-dimethyl-2-butanone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04108756A JPH04108756A (en) | 1992-04-09 |
| JP2946692B2 true JP2946692B2 (en) | 1999-09-06 |
Family
ID=16858177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2227269A Expired - Fee Related JP2946692B2 (en) | 1990-08-28 | 1990-08-28 | Method for producing 3,3-dimethyl-2-butanone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2946692B2 (en) |
-
1990
- 1990-08-28 JP JP2227269A patent/JP2946692B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Ｊｏｕｒｎａｌ ｏｆ ｔｈｅ Ａｍｅｒｉｃａｎ Ｃｈｅｍｉｃａｌ Ｓｏｃｉｅｔｙ（１９８０）１０２ ｐ．５３１１−５３１６ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04108756A (en) | 1992-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |