JPS63303947A - Production of o-formylbenzoic acid - Google Patents
Production of o-formylbenzoic acidInfo
- Publication number
- JPS63303947A JPS63303947A JP14114587A JP14114587A JPS63303947A JP S63303947 A JPS63303947 A JP S63303947A JP 14114587 A JP14114587 A JP 14114587A JP 14114587 A JP14114587 A JP 14114587A JP S63303947 A JPS63303947 A JP S63303947A
- Authority
- JP
- Japan
- Prior art keywords
- alpha
- pentachloro
- xylene
- hydrolyzing
- reaction
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 title claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 6
- UXMNSLMVCBBGCW-UHFFFAOYSA-N 1-(dichloromethyl)-2-(trichloromethyl)benzene Chemical group ClC(Cl)C1=CC=CC=C1C(Cl)(Cl)Cl UXMNSLMVCBBGCW-UHFFFAOYSA-N 0.000 claims abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 230000035484 reaction time Effects 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 10
- 239000013078 crystal Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- CLMSHAWYULIVFQ-UHFFFAOYSA-N 3-bromo-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(Br)OC(=O)C2=C1 CLMSHAWYULIVFQ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
＜１＞ 発明の目的
（産業上の利用分野）
本発明は０−ホルミル安息香酸を工業上有利に製造する
方法に関する。DETAILED DESCRIPTION OF THE INVENTION <1> Object of the Invention (Field of Industrial Application) The present invention relates to an industrially advantageous method for producing 0-formylbenzoic acid.
０−ホルミル安息香酸は医薬、農薬等の中間体としてき
わめて有用な化合物である。O-formylbenzoic acid is an extremely useful compound as an intermediate for pharmaceuticals, agricultural chemicals, and the like.
（従来の技術） 公知の０−ホルミル安息香酸の製造法としては。(Conventional technology) A known method for producing 0-formylbenzoic acid is as follows.
１）３−ブロモフタリドを加水分解する方法。1) Method of hydrolyzing 3-bromophthalide.
（Ｏｒｇ、５ｙｎｔｈ、、ｍ、７Ｂ７）２）α、α、α
、α′、α′−ペンタクロロ−〇−キシレンをベンゼン
スルホン酸の存在下に加水分解する方法、 （米国特許
２．７４８．１３〉α、α、α、α′、α′−ペンタク
ロロ−〇−キシレンを製塩酸中塩化亜鉛の存在下に加水
分解する方法、 く 米国特許２，７４８，１６２ （
１９５６）） 等がある。(Org, 5ynth, , m, 7B7) 2) α, α, α
, a method for hydrolyzing α', α'-pentachloro-〇-xylene in the presence of benzenesulfonic acid, (US Pat. No. 2.748.13) α, α, α, α', α'-pentachloro-〇- A method for hydrolyzing xylene in the presence of zinc chloride in hydrochloric acid, U.S. Pat. No. 2,748,162 (
1956)) etc.
（発明が解決しようとする問題点）
１）の方法は原料が高価である点、２）の方法は高価な
触媒を用いる点、３）の方法は亜鉛排水を生じその処理
を必要とする点、またとくに、２）、３）の方法では触
媒の使用にもかかわらず反応に長時間を必要とし、かつ
、収率がすぐれない点で工業的に有利な製造法とは言い
がたい。(Problems to be solved by the invention) Method 1) uses expensive raw materials, method 2) uses an expensive catalyst, and method 3) generates zinc wastewater, which requires treatment. In particular, methods 2) and 3) require a long reaction time despite the use of a catalyst, and the yields are poor, so they cannot be said to be industrially advantageous production methods.
（２）発明の精成
（問題点を解決するための手段）
本発明者らは上記の問題点を解決するために種々検討し
た結果、経済的に有利であり、かつ、短時間の反応で０
−ホルミル安息香酸を高品質、高収率で得る工業的製造
法を見い出した。(2) Refinement of the invention (means for solving the problems) As a result of various studies to solve the above problems, the present inventors found that it is economically advantageous and requires a short reaction time. 0
-We have discovered an industrial method for producing formylbenzoic acid with high quality and high yield.
以下に本発明の実施方法を更に詳しく説明する。The method of implementing the present invention will be explained in more detail below.
反応温度は１００〜２００℃の範囲で行うが、なかでも
、１４０〜１５０℃の範囲が望ましい、また１反応圧力
は発生する塩酸ガスを反応系内から抜きながら、１〜１
０ Ｋ ｇ ／ ｃ ｍ” （ゲージ圧）の範囲で行う
が、なかでも、３〜４Ｋ ｇ ／ ｃ♂の範囲が望まし
い、これらの条件はとくに限定するものではない。The reaction temperature is in the range of 100 to 200°C, preferably 140 to 150°C, and the reaction pressure is 1 to 1, while removing generated hydrochloric acid gas from the reaction system
It is carried out in a range of 0 K g/cm" (gauge pressure), but a range of 3 to 4 K g/c♂ is particularly desirable; these conditions are not particularly limited.
反応溶媒として水、無機酸、有機酸または有機溶媒と水
との混合溶媒等が用いられる。とくに、水、塩酸が好ま
しい。As a reaction solvent, water, an inorganic acid, an organic acid, a mixed solvent of an organic solvent and water, etc. are used. Particularly preferred are water and hydrochloric acid.
従来の技術では、２０時間程度のきわめて長い反応時間
を必要としたが１本発明法では、無触媒であるにもかか
わらず、わずか１〜３時間で反応が終了する。このこと
は本発明の大きな特徴である。In the conventional technique, an extremely long reaction time of about 20 hours was required, but in the method of the present invention, the reaction is completed in just 1 to 3 hours, even though no catalyst is used. This is a major feature of the present invention.
本発明の出発原料であるα、α、α、α′。α, α, α, α′, which are the starting materials of the present invention.
α′−ペンタクロロー〇−キシレンは、公知の方法によ
り容易に製造できる。 く たとえばＢｅ ｉ １．５
，３６５．Ｃ，Ａ、５２．５４６２ｈ （１９５８））
（実施例）
α、α、α、α′、α′−ペンタクロロ−〇−キシレン
２７８．５ｇ （１，０ｍｏ＋）に水５００ｍ１を加え
オートクレーヴ中１４０〜１５０℃で２時間反応を行っ
た。途中反応により発生する塩酸ガスを抜きながら反応
圧力を３〜４ ｋ ｇ ／ ｃ ｍ”に保った０反応終
了後９０℃まで冷却し１反応液を活性炭２ｇで処理後、
さらに冷却し析出する結晶をろ別した。α'-Pentachloro-xylene can be easily produced by a known method. For example, Be i 1.5
, 365. C, A, 52.5462h (1958)) (Example) 278.5 g (1,0 mo+) of α, α, α, α', α'-pentachloro-〇-xylene was added with 500 ml of water and heated to 140 ~ The reaction was carried out at 150°C for 2 hours. The reaction pressure was maintained at 3 to 4 kg/cm" while removing hydrochloric acid gas generated during the reaction. After the reaction was completed, it was cooled to 90°C and the reaction solution was treated with 2 g of activated carbon.
The mixture was further cooled and precipitated crystals were filtered out.
冷水で洗浄後減圧乾燥し、０−ホルミル安息香酸の白色
結晶１３５．５ｇ （０，９ｍｏ ＋）を得た。収率９
０％ 融点９７．７℃
（参考例）
α、α、α、α′、α′−ペンタクロロ−〇−キシレン
２７８．５ｇ （１，０ｍｏ＋）に３５％塩酸２８０ｍ
１ （３，１ｍｏｌ）と塩化亜鉛５５．７ｇ （０，４
ｍｏ ｌ）とを加え２０時間還流した０反発後水５５０
ｍ１を加え冷却し、析出する結晶をろ過後冷水で洗浄し
た。After washing with cold water and drying under reduced pressure, 135.5 g of white crystals of 0-formylbenzoic acid (0.9 mo +) were obtained. Yield 9
0% Melting point 97.7°C (Reference example) 278.5 g (1,0 mo+) of α, α, α, α', α'-pentachloro-〇-xylene and 280 m of 35% hydrochloric acid
1 (3,1 mol) and zinc chloride 55.7 g (0,4
mol) and refluxed for 20 hours. After 0 repulsion, 550 mol of water
After cooling, the precipitated crystals were filtered and washed with cold water.
３００ｍ１の水から再結晶し、０−ホルミル安息香酸の
白色結晶１２６．０ｇを得た。Recrystallization was performed from 300 ml of water to obtain 126.0 g of white crystals of 0-formylbenzoic acid.
収率８４％ 融点９７．３℃Yield 84% Melting point 97.3°C
Claims (1)
を加圧下に加水分解することを特徴とするｏ−ホルミル
安息香酸の製法。A method for producing o-formylbenzoic acid, which comprises hydrolyzing α, α, α, α', α'-pentachloro-o-xylene under pressure.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14114587A JPS63303947A (en) | 1987-06-04 | 1987-06-04 | Production of o-formylbenzoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14114587A JPS63303947A (en) | 1987-06-04 | 1987-06-04 | Production of o-formylbenzoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63303947A true JPS63303947A (en) | 1988-12-12 |
Family
ID=15285204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14114587A Pending JPS63303947A (en) | 1987-06-04 | 1987-06-04 | Production of o-formylbenzoic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63303947A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5156425A (en) * | 1974-09-20 | 1976-05-18 | Lepetit Spa | |
| JPS525728A (en) * | 1975-06-28 | 1977-01-17 | Dynamit Nobel Ag | Production of phthalaldehyde acid |
-
1987
- 1987-06-04 JP JP14114587A patent/JPS63303947A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5156425A (en) * | 1974-09-20 | 1976-05-18 | Lepetit Spa | |
| JPS525728A (en) * | 1975-06-28 | 1977-01-17 | Dynamit Nobel Ag | Production of phthalaldehyde acid |
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