JPS61134336A - 2-alkoxy-5,9-cyclododecadien-1-ol - Google Patents
2-alkoxy-5,9-cyclododecadien-1-olInfo
- Publication number
- JPS61134336A JPS61134336A JP25788084A JP25788084A JPS61134336A JP S61134336 A JPS61134336 A JP S61134336A JP 25788084 A JP25788084 A JP 25788084A JP 25788084 A JP25788084 A JP 25788084A JP S61134336 A JPS61134336 A JP S61134336A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- unsaturated
- epoxy
- reacting
- 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
Abstract
Description
【発明の詳細な説明】
Ａ、産業上の利用分野
本発明は一般式（１）式で表わされる２−アルコキシ５
．９−シクロドデカジエン−１−オールに関するもので
ある。DETAILED DESCRIPTION OF THE INVENTION A. Industrial Application Field The present invention relates to 2-alkoxy 5 represented by the general formula (1).
．． It relates to 9-cyclododecadien-1-ol.
（Ｉ）
（式中Ｒは、低級アルキル基を示す。）Ｂ１発明が解決
しようとする問題点および問題点を解決するための手段
本発明化合物は文献未記載の新規化合物であり、不飽和
ポリエステル、不飽和エポキシ。(I) (In the formula, R represents a lower alkyl group.) Problems to be solved by the B1 invention and means for solving the problems The compound of the present invention is a new compound that has not been described in any literature, and is an unsaturated polyester. , unsaturated epoxy.
不飽和ポリウレタンの原料として有用なものである。It is useful as a raw material for unsaturated polyurethane.
本発明化合物（Ｉ）は、後述の一般式（Ｉ［＞で表わさ
れる１、５．９〜シクロドデカトリエン（以下、単にＣ
ＤＴと略す。）を出発原料としている。ＣＤＴは、例え
ば、Ｚ １ｌｌｌｏＩｅｒ型触媒を用い、１．３−ブタ
ジェンを三量化することによって得られるものである。The compound (I) of the present invention is a 1,5.9-cyclododecatriene (hereinafter simply referred to as C
It is abbreviated as DT. ) is used as the starting material. CDT is obtained, for example, by trimerizing 1,3-butadiene using a Z 1lloIer type catalyst.
Ｃ６作用
本発明化合物（Ｉ）は、ＣＤＴ（Ｉ［）を用いて、例え
ば、次のような方法で製造することができる。C6 action Compound (I) of the present invention can be produced using CDT (I[), for example, by the following method.
（ｎ）
ＲＯＨＯＲ
（式中Ｒは、例えばメチル、エチルのような低級アルキ
ル基を示す。）
すなわち、（ＩＩ）式で表わされるＣＯＴをエポキシ化
して得られる１、２−エポキシ−５，９−シクロドデカ
ジエン（ＩＩＩ）のオキシラン環の部分にメタノールを
付加することにより得ることができる。ＣＤＴのエポキ
シ化は、例えば、特許第３０９７２８号に記載されてい
る過酸を用いる方法によって行なうことができる。(n) ROHOR (In the formula, R represents a lower alkyl group such as methyl or ethyl.) That is, 1,2-epoxy-5,9- obtained by epoxidizing COT represented by the formula (II) It can be obtained by adding methanol to the oxirane ring portion of cyclododecadiene (III). Epoxidation of CDT can be carried out, for example, by a method using a peracid as described in Japanese Patent No. 309728.
上記のメタノール付加反応は、プロトン酸。The above methanol addition reaction involves protonic acids.
ルイス酸、アルカリ金属およびアルカリ土類金属の水酸
化物、ナトリウム、カリウムのアルコラードなどエーテ
ル化触媒として公知のものから任意に選択して使用する
ことができる。Any known etherification catalyst can be used, such as Lewis acids, hydroxides of alkali metals and alkaline earth metals, and alcoholades of sodium and potassium.
Ｄ、実施例 以下、実施例をあげて本発明を具体的に示す。D. Example Hereinafter, the present invention will be specifically illustrated by giving Examples.
ＣＤＴ （ＩＦ ） １６２ｇ（１ｖｌｌｏｊ！ ＞
を３０％過酸化水素水５５ｇ（ｏ、５１ｏλ）に加え、
ギ酸１３．８＃ （０，３１０ｇ ）の存在下に４０℃
で１１時間反応させた。反応後、蒸留を行ない未反応Ｃ
ＤＴ（ＩＩ ） １０４９ （０，６４１１０λ）と
１．２−エポキシ−５，９−シクロドデカジエン（ＩＩ
Ｉ）６０ｇ（０，３４ｓｏ、ｅ ）を得た（過酸化水素
に対する転化率６８％）。このようにして得られた化合
物（ＩＩＩ） １７８ｇ（１ｓｏぶ）をメタノール３
２０９（１０１０λ）に加え、硫酸０，５Ｊ （０，０
０５ＳＯλ）の存在下に５時間還流させ、反応させた。CDT (IF) 162g (1vlloj! >
was added to 55g (o, 51oλ) of 30% hydrogen peroxide solution,
40°C in the presence of formic acid 13.8# (0,310g)
The reaction was carried out for 11 hours. After the reaction, distillation is performed to remove unreacted C.
DT(II) 1049 (0,64110λ) and 1,2-epoxy-5,9-cyclododecadiene (II
I) 60 g (0.34 so, e ) were obtained (conversion rate relative to hydrogen peroxide 68%). 178 g (1 sob) of the compound (III) thus obtained was added to 3 methanol
209 (1010λ) plus 0.5J sulfuric acid (0,0
05SOλ) for 5 hours to react.
反応後、炭酸バリウム８ｇを加え、ｒａ酸の中和を行っ
た。減圧下にメタノールを除去し、残渣を濾過して無色
液状の化合物（Ｉ）１９５ｇを得た（収率９３％）。こ
の化合物の物性値は次の通りである。After the reaction, 8 g of barium carbonate was added to neutralize the RA acid. Methanol was removed under reduced pressure, and the residue was filtered to obtain 195 g of colorless liquid compound (I) (yield 93%). The physical properties of this compound are as follows.
ＯＬ！（２５℃） ： １．０１４０ 粘度（２
５℃、ＣＰＳ） ： ３３３０ 沸点（℃／１閣）
−１（１） ： １２００ １Ｒスペクトル（液膜
、ａ＋−’）３４６０（０−Ｈ伸縮振動）
２９３６（Ｃ−Ｈ伸縮振動）
１０９２ （Ｃ−０−Ｃ伸縮振動）
ＯＮＭＲスペ’ｙトル（’ＨＮＭＲ，８９，５５Ｍｚ
、ＣＤ（、Ｊ２ｘ ）δ（＋）ｐｍ ）
１．２〜２．４ （ＩＯＨ，シクロドデカジエン核−〇
Ｈｒ ）２．７８ （１Ｈ，シクロドデカジエ
ン核ゝＣＨ−ＯＣＨ３＞３．３６ （３Ｈ，メト
＊シ）Ｌｔ基−０−ＣＨａ）３．８０ （１Ｈ，
ｔニトロキシル基−０−Ｈ）５．２〜５．５（３Ｈ，シ
クロドデカジエン核：Ｃ−ＣＨ−）手続補正書輸発）
昭和６０年２月１９日OL! (25℃): 1.0140 Viscosity (2
5℃, CPS): 3330 Boiling point (℃/1 cabinet)
-1(1): 1200 1R spectrum (liquid film, a+-') 3460 (0-H stretching vibration) 2936 (C-H stretching vibration) 1092 (C-0-C stretching vibration) ONMR spectrum (' HNMR, 89.55Mz
, CD(,J2x)δ(+)pm) 1.2-2.4 (IOH, cyclododecadiene nucleus -〇Hr) 2.78 (1H, cyclododecadiene nucleus もCH-OCH3>3.36 (3H ,meth*shi)Lt group-0-CHa)3.80 (1H,
tNitroxyl group-0-H) 5.2-5.5 (3H, cyclododecadiene nucleus: C-CH-) Procedural amendment imported) February 19, 1985
Claims (1)
る２−アルコキシ−５，９−シクロドデカジエン−１−
オール。[Claims] General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) 2-alkoxy-5,9-cyclo represented by (R in the above formula represents a lower alkyl group) Dodecadiene-1-
All.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25788084A JPS61134336A (en) | 1984-12-05 | 1984-12-05 | 2-alkoxy-5,9-cyclododecadien-1-ol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25788084A JPS61134336A (en) | 1984-12-05 | 1984-12-05 | 2-alkoxy-5,9-cyclododecadien-1-ol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61134336A true JPS61134336A (en) | 1986-06-21 |
Family
ID=17312463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25788084A Pending JPS61134336A (en) | 1984-12-05 | 1984-12-05 | 2-alkoxy-5,9-cyclododecadien-1-ol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61134336A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4990495A (en) * | 1988-12-23 | 1991-02-05 | Firmenich S.A. | Oxygen containing macrocyclic compounds, a process for their preparation and their use as perfuming ingredients |
-
1984
- 1984-12-05 JP JP25788084A patent/JPS61134336A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4990495A (en) * | 1988-12-23 | 1991-02-05 | Firmenich S.A. | Oxygen containing macrocyclic compounds, a process for their preparation and their use as perfuming ingredients |
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