JPS6050794B2 - Pentaerythritol derivative - Google Patents
Pentaerythritol derivativeInfo
- Publication number
- JPS6050794B2 JPS6050794B2 JP56071981A JP7198181A JPS6050794B2 JP S6050794 B2 JPS6050794 B2 JP S6050794B2 JP 56071981 A JP56071981 A JP 56071981A JP 7198181 A JP7198181 A JP 7198181A JP S6050794 B2 JPS6050794 B2 JP S6050794B2
- Authority
- JP
- Japan
- Prior art keywords
- pentaerythritol
- pentaerythritol derivative
- reaction
- methanol
- stirring
- 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
Links
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 title claims description 6
- 239000000126 substance Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 2
- 235000012141 vanillin Nutrition 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical group ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
【発明の詳細な説明】
本発明は新規化合物、さらに詳しくは、式、、７−Ｎ／
、Ｏ−ＣＨ２、、ＮＣＨ２−ＯＮ゛０−−−＜、、△〕
゛−″Ｃｏ−ｃ、Ｏ、、、・Ｃ・、ｃ、Ｏ−、、Ｏで表
わされるペンタエリトリトール誘導体に関するものであ
る。7-N/
, O-CH2,, NCH2-ON゛0---<,,△]
This invention relates to a pentaerythritol derivative represented by "-"Co-c, O, , .C., c, O-, ,O.
本発明の化合物は、反応中間体、殊に、両端にフェノー
ル性水酸基を２個有することから、二仙カルボン酸と重
合反応させることが可能であり、、／”乙−＼＼、、Ｏ
Ｈ゛、 、−ノ 、／
Ｌ→
・−＝ヘ
ーー／（）゛ＩＨ
゛Ｃ！
ポリエステル用モノマーとして有利に利用される。Since the compound of the present invention has a reaction intermediate, especially two phenolic hydroxyl groups at both ends, it can be polymerized with Nisen carboxylic acid.
H゛, , -ノ , / L→ ・-=Hee / ()゛IH ゛C! It is advantageously used as a monomer for polyester.
本発明による化合物は、バニリンとベンタエリトリトー
ルを反応させることによつて製造することができる。The compounds according to the invention can be prepared by reacting vanillin and bentaerythritol.
この反応は、バリニンとペンタエリトリトールを溶媒、
例えば芳香族炭化水素中において、ｐ−トルエンスルホ
ン酸などの酸性物質に存在下で、加熱攪拌することによ
つて実施することができる。In this reaction, valinine and pentaerythritol are used as a solvent,
For example, it can be carried out by heating and stirring in an aromatic hydrocarbon in the presence of an acidic substance such as p-toluenesulfonic acid.
反応温度は、８０〜１１５℃（使用溶媒の沸点）である
。本発明による化合物は、一般に、無色の針状結晶であ
る。The reaction temperature is 80 to 115°C (boiling point of the solvent used). The compounds according to the invention are generally colorless needle-shaped crystals.
次に本発明を実施例により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
バニリン７．５ｇ１ペンタエリトリトール３．収及びｐ
−トルエンスルホン酸０．６ｇを加熱攪拌下にベンゼン
に溶解し、４時間還流した。Example Vanillin 7.5g 1 Pentaerythritol 3. Revenue and p
-0.6 g of toluenesulfonic acid was dissolved in benzene while stirring with heating, and the mixture was refluxed for 4 hours.
生成した水はＤｅａｎ−Ｓｔａｒｋのトラップを用いて
除いた。反応物を室温に冷却後、炭酸カリウム０．３４
ｇ／水１００ｍ１の−アルカリ性水溶液で洗浄し、さら
に水で洗浄した。ベンゼン層を無水硫酸ナトリウムで乾
燥後、減圧濃縮した。この濃縮液にエチルエーテルを加
え、生成した沈澱を濾別し、トルエンから再結晶した。
収率４．５ｇ（５０％）、Ｍｐｌ６９〜１７１℃。参考
例ビス（４−ヒドロキシー３−メトキシベンジリノデン
）ペンタエリトリトール０．６０７ｇ及びトリエチルア
ミン０．４５ｍ１のジクロルメタン溶液１０ｍ１に塩化
テレフタロイル０．３０５ｇのジクロルメタン溶液５ｍ
１を攪拌下に室温てで滴下し、その後２鞘間反応させた
。The water produced was removed using a Dean-Stark trap. After cooling the reaction to room temperature, potassium carbonate 0.34
g/100 ml of water with an alkaline aqueous solution and then with water. The benzene layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. Ethyl ether was added to this concentrated solution, and the resulting precipitate was filtered off and recrystallized from toluene.
Yield 4.5g (50%), Mpl 69-171°C. Reference Example A solution of 0.305 g of terephthaloyl chloride in 5 ml of dichloromethane solution of 0.607 g of bis(4-hydroxy-3-methoxybenzylinodene)pentaerythritol and 0.45 ml of triethylamine in 10 ml of dichloromethane.
1 was added dropwise at room temperature with stirring, followed by a reaction between the two pods.
反応混合物をメタノール４００ｍ１に加え、生じた沈澱
をグラスフィルター上でメタノールを用いた洗浄した。
ｍ−クレゾールとメタノール系で再沈澱し、精製した。
収率０．７４３ｇ（９２．７％）。また、同様にして、
塩化テレフタロイルの代りにセバシン酸ジクロライドを
用て、対応するポリエステルを製造した。このようにし
て得たポリエステルの物性を次に示す。The reaction mixture was added to 400 ml of methanol, and the resulting precipitate was washed with methanol on a glass filter.
It was reprecipitated with m-cresol and methanol and purified.
Yield 0.743g (92.7%). Also, in the same way,
The corresponding polyester was prepared by substituting sebacic acid dichloride for terephthaloyl chloride. The physical properties of the polyester thus obtained are shown below.
〜ＶＴｂυ．υＪＶＯ乙Ｊｑ （７） Ｔｇ・・・・・・ガラス転移点 Ｔｄ・・・・分解点~VTbυ. υJVOOtsuJq (7) Tg...Glass transition point Td...Decomposition point
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56071981A JPS6050794B2 (en) | 1981-05-13 | 1981-05-13 | Pentaerythritol derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56071981A JPS6050794B2 (en) | 1981-05-13 | 1981-05-13 | Pentaerythritol derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57188591A JPS57188591A (en) | 1982-11-19 |
| JPS6050794B2 true JPS6050794B2 (en) | 1985-11-11 |
Family
ID=13476142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56071981A Expired JPS6050794B2 (en) | 1981-05-13 | 1981-05-13 | Pentaerythritol derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6050794B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2023118156A (en) * | 2022-02-15 | 2023-08-25 | 帝人株式会社 | Crystal polymorph of 3,9-bis(4-oxy-3-methoxyphenyl)-2,4,8,10,-tetraoxaspiro[5.5]undecane and method for producing same |
-
1981
- 1981-05-13 JP JP56071981A patent/JPS6050794B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57188591A (en) | 1982-11-19 |
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