JPS6033095B2 - indane derivative - Google Patents
indane derivativeInfo
- Publication number
- JPS6033095B2 JPS6033095B2 JP14112777A JP14112777A JPS6033095B2 JP S6033095 B2 JPS6033095 B2 JP S6033095B2 JP 14112777 A JP14112777 A JP 14112777A JP 14112777 A JP14112777 A JP 14112777A JP S6033095 B2 JPS6033095 B2 JP S6033095B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- parts
- isoprobenylphenol
- mixture
- weight
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
【発明の詳細な説明】
本発明は、次の式（１）
〔但し、Ｒは、ｔ−ブチル基を表す〕
で表わされる１・１・３ートリメチルー３一（３．５−
ジーｔ−ブチルー４−オキシフエニル）一６−ｔ−ブチ
ルインダンー５ーオールに関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides 1,1,3-trimethyl-3-(3,5-
(di-t-butyl-4-oxyphenyl)-6-t-butylindan-5-ol.
本発明の化合物は、塩化ビニル樹脂、ポリエチレン、ポ
リプロピレン、ポリウレタン、ポリスチレン、ゴム等の
安定剤として、効果を発揮するものである。The compound of the present invention is effective as a stabilizer for vinyl chloride resin, polyethylene, polypropylene, polyurethane, polystyrene, rubber, and the like.
本発明の〔１〕式の化合物は、例えば、ｐーィソプロベ
ニルフェノールまたはその重合体を含むものを出発原料
として、これを鎖状２量体とし、次に環化反応を行って
１・１・３ートリメチル−３一（４−オキシフエニル）
ーインダンー５ーオールを合成し、続いてアルキル化反
応させて、ｔープチル基を導入することによって製造す
ることができる。The compound of formula [1] of the present invention can be obtained by using, for example, a starting material containing p-isoprobenylphenol or a polymer thereof, converting this into a chain dimer, and then performing a cyclization reaction. 1,1,3-trimethyl-3-(4-oxyphenyl)
It can be produced by synthesizing -indan-5-ol and subsequently performing an alkylation reaction to introduce a t-butyl group.
而して、ｐーイソプロベニルフェノールの鎖状２量体は
、及び
の構造を有するものであって、公知の方法、例えば特公
昭５２−１０８６ｙ言明細書に記載された方法によって
合成することがだでき、且つ容易に単離することができ
る。Therefore, the chain dimer of p-isoprobenylphenol has the structure of It can be separated and easily isolated.
ｐーィソプロベニルフェノールの鎖状２重体を環化反応
する際に用いる触媒は、フェノールのアルキル化反応に
用いられる公知の酸触媒が用いられ、例えば、塩化アル
ミニウム、塩化第２鉄、塩化第２スズ、フッ化ホウ素等
のルイス酸、硫酸、リン酸、塩酸、過塩素酸、ベンゼン
スルホン酸、トルェンスルホン酸等のプロトン酸、およ
びシリカァルミナ、活性白土、陽イオン交換樹脂等の固
体酸が用いられる。The catalyst used in the cyclization reaction of the chain doublet of p-isoprobenylphenol is a known acid catalyst used in the alkylation reaction of phenol, such as aluminum chloride, ferric chloride, Lewis acids such as stannic chloride and boron fluoride, protonic acids such as sulfuric acid, phosphoric acid, hydrochloric acid, perchloric acid, benzenesulfonic acid and toluenesulfonic acid, and solids such as silica alumina, activated clay, and cation exchange resins. Acid is used.
而して上記した触媒の使用量は、原料物質の総量に対し
て通常０．０１〜２０重量％、好ましくは０．５〜１の
重量％の範囲である。The amount of the above-mentioned catalyst used is usually in the range of 0.01 to 20% by weight, preferably 0.5 to 1% by weight, based on the total amount of raw materials.
反応に際しては、ベンゼン、トルェン・キシレンなどの
芳香族炭化水素、ニトロベンゼン、アニソール、クロル
ベンゼンなどの置換芳香族炭化水素、および塩化メチレ
ン、クロロホルム、四塩化炭素、エチレンジクロリド、
テトラクロルェタンなどのハロゲン化炭化水素が用いら
れる。During the reaction, aromatic hydrocarbons such as benzene, toluene/xylene, substituted aromatic hydrocarbons such as nitrobenzene, anisole, and chlorobenzene, methylene chloride, chloroform, carbon tetrachloride, ethylene dichloride,
Halogenated hydrocarbons such as tetrachloroethane are used.
これらの溶剤の使用量は、通常原料物質の総量に対し２
０〜５００の重量％、好ましくは１００〜２００の重量
％の範囲で用いられる。而してこの反応における反応温
度は、通常３０〜２０ぴ○の範囲である。The amount of these solvents used is usually 2 times the total amount of raw materials.
It is used in a range of 0 to 500% by weight, preferably 100 to 200% by weight. The reaction temperature in this reaction is usually in the range of 30 to 20 pi.
Ｐーィソプロベニルフェノールの鎖状２量体の環化反応
によって得られた環状２量体のアルキル化反応は、環化
反応生成物より環状２重体を単離しても、また単離しな
くても行いうる。In the alkylation reaction of the cyclic dimer obtained by the cyclization reaction of the chain dimer of P-isoprobenylphenol, the cyclic dimer can be isolated even if the cyclic dimer is isolated from the cyclization reaction product. You can do it without it.
アルキル化反応に用いられる触媒および溶剤は、上記環
化反応において用いられたものが同様に使用可能であり
、また反応温度条件も同様である。ｔーブチル化に使用
されるブチル化剤としては、ハロゲン化ブチル、セカン
ダリープチルアルコール、イソブチレン等が使用でき、
反応は、常氏下でも加圧下でも行いうる。The catalyst and solvent used in the alkylation reaction can be the same as those used in the cyclization reaction, and the reaction temperature conditions are also the same. As the butylating agent used for t-butylation, halogenated butyl, secondary butyl alcohol, isobutylene, etc. can be used.
The reaction can be carried out under normal conditions or under pressure.
以下実施例によって更に説明する。This will be further explained below with reference to Examples.
実施例 １
Ｐーイソブロベニルフェノールより製造した純度９０重
量％のＰーィソプロベニルフヱノールの鎖状２塁体１０
部（以下、部は重量部を示す〉、ベンゼン５礎部、市販
シリカアルミナ１部を、ガラス製反応器に菱入し、沸点
下で３時間加熱環流させた。Example 1 Chain-like second base body of P-isoprobenylphenol with a purity of 90% by weight produced from P-isoprobenylphenol 10
(Hereinafter, "parts" indicate parts by weight), 5 parts of benzene, and 1 part of commercially available silica alumina were charged into a glass reactor, and heated under reflux for 3 hours at the boiling point.
冷却后メタノール１礎都を添加し、触媒のシリカアルミ
ナを炉別した。炉液よりメタノールを留去し、冷却して
析出してくる結晶を炉別、乾燥を行ない、８．２部の環
状２量体を得た。上記の環状２量体５部、ベンゼン２５
部、および腸イオン交換樹脂アンバーリスト−１５（商
品名）１．５部を２００泌フラスコに装入し、温度６０
午○でかさまぜながら、ィソプチレンを１４叫′ｍｉｎ
の速度で４時間吹き込んだ。After cooling, one portion of methanol was added, and the silica alumina catalyst was separated in the furnace. Methanol was distilled off from the furnace liquid, and the crystals precipitated by cooling were separated in the furnace and dried to obtain 8.2 parts of a cyclic dimer. 5 parts of the above cyclic dimer, 25 parts of benzene
and 1.5 parts of intestinal ion exchange resin Amberlyst-15 (trade name) were placed in a 200-ml flask and heated to 60°C.
While stirring in the afternoon, add isoptylene for 14 min.
The air was blown at a speed of 4 hours.
反応終了後、腸イオン交換樹脂を炉刺し、母液を濃縮、
続いて冷却することにより白色結晶が析出した。結晶の
乾燥重量は４．＄部であった。After the reaction is complete, the intestinal ion exchange resin is pierced in a furnace, the mother liquor is concentrated,
Subsequently, white crystals were precipitated by cooling. The dry weight of the crystals is 4. It was the $ section.
この結晶の融点は、１７９．５℃であり、核磁気共鳴の
測定結果は、以下の通りであった。核磁気共鳴（６、肌
）
１．０５ＣＨ３ ａ
１．２９ＣＨ３ ｂ
１．３８ＣＨ３ ｃ
１．４３ＣＨ３ ｄ
１．６２ＣＨ３ ｅ
１．９５ＣＨ３ ｆ
２．１７ 〃
２．２４ 〃
２．４５ 〃
６．３２ ０−Ｈ ｇ
６．９１ 〃 ｉ
６．９７ 〃 ｊ
４．４５０日 ｋ
４．班 〃
核弱気共鳴スペクトル図を第１図に示し、赤外吸収スペ
クトル図を第２図に示した。The melting point of this crystal was 179.5°C, and the results of nuclear magnetic resonance measurements were as follows. Nuclear magnetic resonance (6, skin) 1.05CH3 a 1.29CH3 b 1.38CH3 c 1.43CH3 d 1.62CH3 e 1.95CH3 f 2.17 〃 2.24 〃 2.45 〃 6.32 0-H g 6.91 〃 i 6.97 〃 j 4.450 days k 4. Team Figure 1 shows the nuclear bearish resonance spectrum, and Figure 2 shows the infrared absorption spectrum.
実施例 ２
Ｐーイソプロベニルフエノールのモノマ−１０．５％、
ダイマー６０．３％、トリマー１５．６％、テトラマー
８．６％、ベンタマ−１．０％およびへキサマー以上１
．５％（何れも重量％）よりなる、Ｐーィソプロベニル
フェノールおよびその重合体の混合物５碇郭とベンゼン
１０礎郭、および、陽イオン交換樹脂アンバーリンス１
５（商品名）５部を５００の【フラスコに仕込み、反応
温度６び０で６時間燈拝させた。Example 2 P-isoprobenylphenol monomer 10.5%,
60.3% dimer, 15.6% trimer, 8.6% tetramer, 1.0% bentamer and more than 1 hexamer
．． A mixture of P-isoprobenylphenol and its polymer consisting of 5% (both weight %) 5. Anchorage, 10. Benzene and 1.0% cation exchange resin Amber Rinse.
5 (trade name) was placed in a 500ml flask, and the mixture was heated at a reaction temperature of 6-0 for 6 hours.
この反応物を冷却后生成した白色結晶とイオン交換樹脂
との混合物をベンゼン層より炉別した。After cooling the reaction product, a mixture of white crystals and ion exchange resin was separated from the benzene layer.
得られた混合物は環状２量体２８部とイオン交換樹脂５
部との混合物３３部であった。この混合物１５部と塩化
メチレン５碇部をフラスコに装入し、温度４０℃で燈拝
しながら、ィソプチレンを毎分１０泌の速．度で吹き込
みならが１岬時間反応させた。反応物から塩化メチレン
を蟹去した后、メタノールを加えて生成物を溶解した後
、炉過し、触媒を分離した。炉液に水を加え生成する沈
澱を炉別した。この沈毅物をベンゼンーメタノールで再
結晶させ、白色結晶５．＄部を得た。この結晶の融点は
１８０ｑｏであり、赤外吸収スペクトルおよび核磁気共
鳴の測定結果は、実施例１と同じであった。The resulting mixture contained 28 parts of the cyclic dimer and 5 parts of the ion exchange resin.
The total amount of the mixture was 33 parts. 15 parts of this mixture and 5 parts of methylene chloride were charged into a flask, and while heating at a temperature of 40°C, isoptylene was secreted at a rate of 10 parts per minute. It was blown at a temperature of 50°C and allowed to react for 1 hour. After methylene chloride was removed from the reaction mixture, methanol was added to dissolve the product, and the mixture was filtered through an oven to separate the catalyst. Water was added to the furnace liquid and the resulting precipitate was separated from the furnace. This precipitate was recrystallized from benzene-methanol to give white crystals5. I got the $ part. The melting point of this crystal was 180 qo, and the measurement results of infrared absorption spectrum and nuclear magnetic resonance were the same as in Example 1.
第１図は本発明の１・１・３ートリメチルー３−（３．
５ージーｔ−プチルー４ーオキシフエニル）−６−ｔー
ブチルィンダンー５−オールの核磁気共鳴スペクトル図
を示したものであり、第２図は同じく赤外吸収スペクト
ル図である。
多ｌ図
第２図FIG. 1 shows the 1,1,3-trimethyl-3-(3.
This figure shows a nuclear magnetic resonance spectrum of 5-di-t-butyl-4-oxyphenyl)-6-t-butylindan-5-ol, and FIG. 2 is an infrared absorption spectrum as well. Figure 2
Claims (1)
ジ−ｔ−ブチル−４−オキシフエニル）−６−ｔ−ブチ
ルインダン−５−オール。[Claims] 1 1.1.3-trimethyl-3-(3.5 −
di-t-butyl-4-oxyphenyl)-6-t-butylindan-5-ol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14112777A JPS6033095B2 (en) | 1977-11-26 | 1977-11-26 | indane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14112777A JPS6033095B2 (en) | 1977-11-26 | 1977-11-26 | indane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5476564A JPS5476564A (en) | 1979-06-19 |
| JPS6033095B2 true JPS6033095B2 (en) | 1985-08-01 |
Family
ID=15284783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14112777A Expired JPS6033095B2 (en) | 1977-11-26 | 1977-11-26 | indane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6033095B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19728378C1 (en) * | 1997-07-03 | 1999-03-11 | Bayer Ag | Preparation and purification of 3- (4-hydroxyphenyl) -1,1,3-trimethylindan-5-ol |
| DE19728377C1 (en) * | 1997-07-03 | 1999-02-18 | Bayer Ag | Preparation and purification of 3- (4-hydroxyphenyl) -1,1,3-trimethylindan-5-ol |
| DE19728379C1 (en) * | 1997-07-03 | 1999-02-18 | Bayer Ag | Preparation and purification of 3- (4-hydroxyphenyl) -1,1,3-trimethylindan-5-ol |
-
1977
- 1977-11-26 JP JP14112777A patent/JPS6033095B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5476564A (en) | 1979-06-19 |
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