JPH0519546B2 - - Google Patents
Info
- Publication number
- JPH0519546B2 JPH0519546B2 JP2688586A JP2688586A JPH0519546B2 JP H0519546 B2 JPH0519546 B2 JP H0519546B2 JP 2688586 A JP2688586 A JP 2688586A JP 2688586 A JP2688586 A JP 2688586A JP H0519546 B2 JPH0519546 B2 JP H0519546B2
- Authority
- JP
- Japan
- Prior art keywords
- trifluoro
- acid
- mercaptophthalic
- novel
- mol
- 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 - Lifetime
Links
- JXVICXPMIXTSIU-UHFFFAOYSA-N 3,4,6-trifluoro-5-sulfanylphthalic acid Chemical compound OC(=O)C1=C(F)C(F)=C(S)C(F)=C1C(O)=O JXVICXPMIXTSIU-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 4
- YJLVXRPNNDKMMO-UHFFFAOYSA-N 3,4,5,6-tetrafluorophthalic acid Chemical compound OC(=O)C1=C(F)C(F)=C(F)C(F)=C1C(O)=O YJLVXRPNNDKMMO-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、式（）で示される新規な３，５，
６−トリフルオロ−４−メルカプトフタル酸に関
するものである。Detailed Description of the Invention (Field of Industrial Application) The present invention provides novel 3,5,
It relates to 6-trifluoro-4-mercaptophthalic acid.
本発明によつて提供される式（）で示される
新規な３，５，６−トリフルオロ−４−メルカプ
トフタル酸は、反応活性なＳ−Ｈ基を有する３官
能化合物であり、写真用有機材料、エポキシ硬化
剤、機能性高分子材料や医・農薬合成の出発原料
として使用することの出来るきわめて有用な化合
物である。 The novel 3,5,6-trifluoro-4-mercaptophthalic acid represented by the formula () provided by the present invention is a trifunctional compound having a reactive S-H group, and is a photographic organic compound. It is an extremely useful compound that can be used as a raw material, epoxy curing agent, functional polymer material, and starting material for the synthesis of medicines and agricultural chemicals.
（従来の技術）
本発明による式（）で示される新規な３，
５，６−トリフルオロ−４−メルカプトフタル酸
の製造方法は今までまつたく報告されていない。(Prior art) The novel 3, represented by the formula () according to the present invention,
No method for producing 5,6-trifluoro-4-mercaptophthalic acid has been reported so far.
（発明の概要）
本発明者らは、式（）で示される新規な３，
５，６−トリフルオロ−４−メルカプトフタル酸
の製造方法を検討した結果、水媒体中で例えば水
酸化ナトリウムなどのアルカリ金属水酸化物の存
在下に、テトラフルオロフタル酸と例えば硫化水
素ナトリウムなどの硫化水素アルカリ金属とを反
応させ、ついで酸析することによつて新規な３，
５，６−トリフルオロ−４−メルカプトフタル酸
を高収率で製造できることを見出した。なお、本
発明の３，５，６−トリフルオロ−４−メルカプ
トフタル酸の製造方法が上記のものに限定されな
いことは勿論である。(Summary of the invention) The present inventors have discovered a novel 3,
As a result of studying a method for producing 5,6-trifluoro-4-mercaptophthalic acid, it was found that tetrafluorophthalic acid and sodium hydrogen sulfide, for example, in the presence of an alkali metal hydroxide such as sodium hydroxide in an aqueous medium. A novel 3,
It has been found that 5,6-trifluoro-4-mercaptophthalic acid can be produced in high yield. It goes without saying that the method for producing 3,5,6-trifluoro-4-mercaptophthalic acid of the present invention is not limited to the above method.
以下、本発明における新規物質の製造方法を実
施例により具体的に説明し、得られた新規物質を
同定するための分析結果をもあわせて示した。 Hereinafter, the method for producing the novel substance according to the present invention will be specifically explained using Examples, and the analysis results for identifying the obtained novel substance will also be shown.
実施例 １
攪拌機、温度計、ジムロート型冷却器および滴
下漏斗を備えた容量200mlの４つの口フラスコに
窒素雰囲気下で95％水酸化ナトリウム6.36ｇ
（0.151モル）を60mlの水に溶解し、ついでこの溶
液を20℃に保ちテトラフルオロフタル酸11.98ｇ
（0.050モル）を溶解させた。その後、温度を20℃
に維持しながら70％硫化水素ナトリウム4.43ｇ
（0.055モル）を水40mlに溶解した水溶液を滴下し
た。滴下終了後90℃に昇温し12時間反応した。Example 1 6.36 g of 95% sodium hydroxide under nitrogen atmosphere in a 200 ml four-necked flask equipped with a stirrer, thermometer, Dimroth condenser and addition funnel.
(0.151 mol) in 60 ml of water, then keep this solution at 20°C and 11.98 g of tetrafluorophthalic acid.
(0.050 mol) was dissolved. Then increase the temperature to 20℃
70% Sodium Hydrogen Sulfide 4.43g while maintaining
(0.055 mol) dissolved in 40 ml of water was added dropwise. After the dropwise addition was completed, the temperature was raised to 90°C and the mixture was reacted for 12 hours.
次に、冷却後反応液を過してその液を6N
塩酸水溶液100mlに注入し３，５，６−トリフル
オロ−４−メルカプトフタル酸を生成させた。 Next, after cooling, filter the reaction solution and add 6N
The mixture was poured into 100 ml of an aqueous hydrochloric acid solution to produce 3,5,6-trifluoro-4-mercaptophthalic acid.
得られた３，５，６−トリフルオロ−４−メル
カプトフタル酸を含む水溶液をジエチルエーテル
150mlにより有機層に３，５，６−トリフルオロ
−４−メルカプトフタル酸を抽出した。この抽出
操作を３回行なつた後、得られたジエチルエーテ
ル層全体を50mlの水で２回洗浄して分液し、無水
硫酸マグネシウムで乾燥後、蒸発乾固して３，
５，６−トリフルオロ−４−メルカプトフタル酸
9.92ｇ（0.0394モル、対テトラフルオロフタル酸
収率78.8モル％）を得た。 The resulting aqueous solution containing 3,5,6-trifluoro-4-mercaptophthalic acid was dissolved in diethyl ether.
3,5,6-trifluoro-4-mercaptophthalic acid was extracted into the organic layer using 150 ml. After performing this extraction operation three times, the entire diethyl ether layer obtained was washed twice with 50 ml of water to separate the layers, dried over anhydrous magnesium sulfate, and then evaporated to dryness.
5,6-trifluoro-4-mercaptophthalic acid
9.92 g (0.0394 mol, yield 78.8 mol% based on tetrafluorophthalic acid) was obtained.
さらに、このものをジイソプロピルエーテルよ
り再結晶することによつて精製した３，５，６−
トリフルオロ−４−メルカプトフタル酸について
次の物性値をえて構造を特定した。 Furthermore, 3,5,6- purified by recrystallizing this product from diisopropyl ether
The structure of trifluoro-4-mercaptophthalic acid was determined by obtaining the following physical property values.
Γ融点 148.9℃
Γ元素分析値
Ｃ(%) Ｈ(%) Ｆ(%) Ｓ（％）
理論値 38.11 1.20 22.60 12.71
分析値 37.98 1.25 22.55 12.68
Γ赤外吸収スペクトル （KBr錠剤、単位cm-1）
2990 （ヒドロキシν-O-H）
2572 （メルカプトν-S-H）
1712，1698 （カルボニルν>C=O）
（尚、赤外吸収スペクトル図を第１図に示し
た。）
Γ19F NMR（溶媒：アセトン−d6、
内部標準物質：CF3 COOH）ppm
F3 δ−37.71，dd（Ｊ＝5.3，14.2Hz）
F5 δ−65.03，dd（Ｊ＝14.2，21.4Hz）
F6 δ−51.53，dd（Ｊ＝5.3，21.5Hz）Γ melting point 148.9℃ Γ elemental analysis value C (%) H (%) F (%) S (%) Theoretical value 38.11 1.20 22.60 12.71 Analysis value 37.98 1.25 22.55 12.68 Γ infrared absorption spectrum (KBr tablet, unit cm -1 ) 2990 (Hydroxy ν -OH ) 2572 (Mercapto ν -SH ) 1712, 1698 (Carbonyl ν> C=O ) (The infrared absorption spectrum is shown in Figure 1.) Γ 19 F NMR (Solvent: Acetone −d 6 , internal standard: CF 3 COOH) ppm F 3 δ−37.71, dd (J=5.3, 14.2Hz) F 5 δ−65.03, dd (J=14.2, 21.4Hz) F 6 δ−51.53, dd (J=5.3, 21.5Hz)
第１図は実施例で得られた３，５，６−トリフ
ルオロ−４−メルカプトフタル酸の赤外吸収スペ
クトル図である。
FIG. 1 is an infrared absorption spectrum diagram of 3,5,6-trifluoro-4-mercaptophthalic acid obtained in Examples.
Claims (1)
フタル酸。1 3,5,6-trifluoro-4-mercaptophthalic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2688586A JPS62185066A (en) | 1986-02-12 | 1986-02-12 | 3,5,6-trifluoro-4-mercaptophthalic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2688586A JPS62185066A (en) | 1986-02-12 | 1986-02-12 | 3,5,6-trifluoro-4-mercaptophthalic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62185066A JPS62185066A (en) | 1987-08-13 |
| JPH0519546B2 true JPH0519546B2 (en) | 1993-03-17 |
Family
ID=12205721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2688586A Granted JPS62185066A (en) | 1986-02-12 | 1986-02-12 | 3,5,6-trifluoro-4-mercaptophthalic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62185066A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005036693A1 (en) * | 2005-08-04 | 2007-02-08 | Degussa Ag | Process for the preparation of 2,4,6-trimercapto-1,3,5-triazine |
-
1986
- 1986-02-12 JP JP2688586A patent/JPS62185066A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62185066A (en) | 1987-08-13 |
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