JPH0499744A - Aromatic dialdehyde and synthesis thereof - Google Patents

Aromatic dialdehyde and synthesis thereof

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Publication number
JPH0499744A
JPH0499744A JP2215985A JP21598590A JPH0499744A JP H0499744 A JPH0499744 A JP H0499744A JP 2215985 A JP2215985 A JP 2215985A JP 21598590 A JP21598590 A JP 21598590A JP H0499744 A JPH0499744 A JP H0499744A
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formula
general formula
chemical
formulas
aromatic
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JP2535742B2 (en
Inventor
Mutsuo Tanaka
睦生 田中
Yoshie Soma
相馬　芳枝
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National Institute of Advanced Industrial Science and Technology
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Agency of Industrial Science and Technology
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

NEW MATERIAL:An aromatic dialdehyde expressed by either one of formula I (R1 is 1-3C alkyl), formula II (R2 is H or 1-3C alkyl) and formula III (R3 is 1-3C alkylene). EXAMPLE:1,5-Naphthodialdehyde (formula I), 4,4'-formyldiphenyl (formula II) or 4,4'-formyldibenzyl (formula III). USE:Useful as a synthetic intermediate for medicine or dye and as a raw material for producing plastic. PREPARATION:An aromatic compound expressed by either one of formula IV to formula VI is reacted with carbon monoxide in the presence of hydrogen fluoride and antimony pentafluoride to provide the corresponding compound expressed by formula I to formula III.

Description

【発明の詳細な説明】 産業上の利用分野 本発明は、医薬品、染料、エンジニアリングプラスティ
ック等の原料として有用な芳香族ジアルデヒド及びその
合成方法に関する。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to an aromatic dialdehyde useful as a raw material for pharmaceuticals, dyes, engineering plastics, etc., and a method for synthesizing the same.

従来の技術 芳香族アルデヒド化合物は、医薬品や染料などの合成中
間体として、また、エンジニアリングプラスティックの
製造原料として、工業−１−重要な化合物である。BACKGROUND OF THE INVENTION Aromatic aldehyde compounds are important compounds in industry as synthetic intermediates for pharmaceuticals and dyes, and as raw materials for manufacturing engineering plastics.

従来より、ルイス酸とブレンステッド酸の存在下、芳香
族化合物と一酸化炭素を反応させて、芳香族化合物に一
つのホルミル基を導入する方法はガラターマン−コツホ
反応としてよく知られている。しかしながら、芳香族化
合物に二つのホルミル基を一段階で導入する合成方法は
知られていない。Conventionally, a method of introducing one formyl group into an aromatic compound by reacting an aromatic compound with carbon monoxide in the presence of a Lewis acid and a Brønsted acid is well known as the Galaterman-Kotzho reaction. However, no synthetic method is known for introducing two formyl groups into an aromatic compound in one step.

発明の開示 本発明芳香族ジアルデヒド化合物は、文献未載の新規化
合物であって、下記一般式（１）〜（３）のいずれかで
表わされる。Disclosure of the Invention The aromatic dialdehyde compound of the present invention is a novel compound that has not been published in any literature, and is represented by any of the following general formulas (1) to (3).

一般式（１） 〔式中、Ｒ１は％　ＣＩ　−０３のアルキル基を示す。General formula (1) [In the formula, R1 represents an alkyl group of % CI-03.

〕 一般式（２） ％式％ 〔式中、Ｒ２は、ＨもしくはＣ１〜Ｃ３のアルキル基を
示す。〕 一般式（３） 〔式中、Ｒ３は、ｃ、−Ｃ３のアルキル鎖を示す。〕 本発明石は、芳香族化合物のカルボニル化反応に関して
鋭意研究を進めた結果、芳香族化合物に二つのホルミル
基を導入した化合物を、わずか−段階で合成し得ること
を見出し、本発明を完成するに至った。] General formula (2) % formula % [In the formula, R2 represents H or a C1 to C3 alkyl group. ] General formula (3) [In the formula, R3 represents an alkyl chain of c or -C3. 〕 As a result of intensive research into the carbonylation reaction of aromatic compounds, the present inventor discovered that it is possible to synthesize a compound in which two formyl groups are introduced into an aromatic compound in just a few steps, and completed the present invention. I ended up doing it.

一酸化炭素雰囲気下、従来の触媒中に芳香族化合物を加
えただけでは、一つのホルミル基が導入された芳香族化
合物しか得られない。If an aromatic compound is simply added to a conventional catalyst under a carbon monoxide atmosphere, only an aromatic compound into which one formyl group has been introduced can be obtained.

しかしながら本発明者の研究によれば、−に記−酸化炭
素と芳香族化合物との反応をフッ化水素及び五フッ化ア
ンチモンの存在下で行ったときは、−段の反応で二つの
ホルミル基が導入された芳香族化合物が得られることが
わかった。However, according to the research of the present inventor, when the reaction between carbon oxide and an aromatic compound is carried out in the presence of hydrogen fluoride and antimony pentafluoride, two formyl groups are formed in the -stage reaction. It was found that an aromatic compound into which is introduced can be obtained.

本発明の一般式（１）〜（３）で表わされる化合物は、
それぞれ下記一般式（４）〜（６）で表わされる芳香族
化合物と一酸化炭素との反応により得られる。The compounds represented by general formulas (1) to (3) of the present invention are:
They are obtained by reacting aromatic compounds represented by the following general formulas (4) to (6) with carbon monoxide.

一般式（４） 〔式中、Ｒ２は、前記と同じ。〕 一般式（５） 〔式中、Ｒ２は、前記と同じ。〕 一般式（６） 〔式中、Ｒ３は、前記と同じ。〕 上記一般式（４）で表わされる化合物としては、例えば
ナフタレン、１−メチルナフタレン、２−メチルナフタ
レン、１−エチルナフタレン、２−エチルナフタレン、
１−プロピルナフタレン等が挙げられる。General formula (4) [In the formula, R2 is the same as above. ] General formula (5) [In the formula, R2 is the same as above. ] General formula (6) [In the formula, R3 is the same as above. ] Examples of the compound represented by the above general formula (4) include naphthalene, 1-methylnaphthalene, 2-methylnaphthalene, 1-ethylnaphthalene, 2-ethylnaphthalene,
Examples include 1-propylnaphthalene.

一般式（５）で表わされる化合物としては、例えばジフ
ェニル、４−メチルジフェニル、４−エチルジフェニル
、４−プロピルジフェニル、２メチルジフエニル、３−
メチルジフェニル等が挙げられる。Examples of the compound represented by the general formula (5) include diphenyl, 4-methyldiphenyl, 4-ethyldiphenyl, 4-propyldiphenyl, 2methyldiphenyl, 3-
Examples include methyldiphenyl.

一般式（６）で表わされる化合物としては、例えばジフ
ェニルメタン、ジベンジル、１，３−ジフェニルプロパ
ン等が挙げられる。Examples of the compound represented by general formula (6) include diphenylmethane, dibenzyl, and 1,3-diphenylpropane.

本発明において、上記一般式（４）〜（６）で表わされ
る芳香族化合物は、フッ化水素及び五フッ化アンチモン
の混合溶液中に加えられ、−酸化炭素雰囲気中、撹拌下
に反応させられる。In the present invention, the aromatic compounds represented by the above general formulas (4) to (6) are added to a mixed solution of hydrogen fluoride and antimony pentafluoride, and reacted with stirring in a carbon oxide atmosphere. .

上記五フッ化アンチモンの使用量としては、特に制限さ
れないが、通常、加えられる芳香族化合物の０．５〜１
０倍モル量程度、好ましくは２〜８倍モル量程度とする
のがよい。The amount of antimony pentafluoride used is not particularly limited, but is usually 0.5 to 1 % of the aromatic compound added.
The amount is preferably about 0 times the molar amount, preferably about 2 to 8 times the molar amount.

フッ化水素の使用量としては、特に制限されず広い範囲
から選ぶことができるが、通常五フッ化アンチモンに対
して５〜５０倍モル量とするのがよい。反応は、−酸化
炭素雰囲気中で行われるが、そのときの圧力は、特に制
限されず、常圧でも加圧でもよい。The amount of hydrogen fluoride to be used is not particularly limited and can be selected from a wide range, but it is usually 5 to 50 times the molar amount of antimony pentafluoride. The reaction is carried out in a -carbon oxide atmosphere, but the pressure at that time is not particularly limited and may be normal pressure or increased pressure.

また、反応温度は、０〜３０℃程度が好ましい。Moreover, the reaction temperature is preferably about 0 to 30°C.

本発明では、反応途中又は反応終了後、例えば反応混合
物を水中に注ぎ、ベンゼンで抽出して目的物のホルミル
基を二つ導入した芳香族化合物を回収することができる
。また、得られた多環芳香族化合物は、再結晶すること
によって精製され得る。In the present invention, during or after the reaction, for example, the reaction mixture is poured into water and extracted with benzene to recover the target aromatic compound into which two formyl groups have been introduced. Moreover, the obtained polycyclic aromatic compound can be purified by recrystallization.

発明の効果 本発明化合物は、置換基が複数導入されているので、医
薬、農薬等の原料又は中間体として用いた場合、最終目
的化合物への合成工程の短縮を図ることができる。また
、エンジニアリングプラスティックの原料として用いた
場合には、新たな物性を庁する新規化合物が得られると
期待される。Effects of the Invention Since the compound of the present invention has a plurality of substituents introduced therein, when used as a raw material or intermediate for medicines, agricultural chemicals, etc., it is possible to shorten the synthesis steps to obtain the final target compound. Furthermore, when used as a raw material for engineering plastics, it is expected that new compounds with new physical properties will be obtained.

実施例 以下実施例を示し、本発明の特徴とするところをより一
層明確なものとする。尚、実施例で得られた生成物の構
造は、ＮＭＲ１ＩＲ１質量分析により確認された。EXAMPLES Hereinafter, examples will be shown to further clarify the characteristics of the present invention. The structure of the product obtained in the example was confirmed by NMR1IR1 mass spectrometry.

実施例１ フッ化水素１０．０ｇ　（５００ｍｍｏｌ）と五フッ化
アンチモン１２．　９６ｇ　（６０ｍｍｏｌ）の混合溶
液に、０℃でナフタレン１．　２８ｇ　（１０ｍｍｏｌ
）を加え、−酸化炭素圧６０気圧の下で、最初の１時間
は０℃、残りの１時間は２０℃で合計２時間撹拌した後
、反応液を水中に注ぎ、ベンゼンで抽出して、１−ナフ
トアルデヒド０．　３４ｇ　（収率２２％）、１．５−
ナフトジアルデヒド０．８７ｇ（収率４７％）を得た。Example 1 10.0 g (500 mmol) of hydrogen fluoride and 12.0 g (500 mmol) of hydrogen fluoride and antimony pentafluoride. To a mixed solution of 96 g (60 mmol) was added 1.0 ml of naphthalene at 0°C. 28g (10mmol
) and stirred under a carbon oxide pressure of 60 atm at 0°C for the first hour and 20°C for the remaining hour for a total of 2 hours, the reaction solution was poured into water and extracted with benzene. 1-Naphthaldehyde 0. 34g (yield 22%), 1.5-
0.87 g (yield 47%) of naphthodialdehyde was obtained.

物性値 １．５−ナフトジアルデヒド ＩＲ（ｃｍ””）：１６８０，１５００．１２００゜９
２０．７８０ ＩＨ−ＮＭＲδ（ＣＤＣＡ！３）ニ ア、　６〜９．８　（ｍ、　６Ｈ，ａｒｏｍａｔｉｃＨ
）１０．４９　（ｓ、２Ｈ，−ＣＨＯ） ＭＳ：Ｍ”＝１８４ 融点：１９２〜１９３℃ 実施例２ フッ化水素１０．　０ｇ　（５００ｍｍｏｌ）と五フッ
化アンチモン５．４０　ｇ　（２５ｍｍｏｌ）の混合溶
液に、０℃で１−メチルナフタレン１．４２ｇ　（１０
ｍｍｏｌ）を加え、−酸化炭素圧２０気圧の下で６時間
撹拌した後、反応液を水中に注ぎ、ベンゼンで抽出して
、４−メチルナフトアルデヒド０．６６ｇ（収率３９％
）と、４−メチル−１，５−ナフトジアルデヒド１．０
３ｇ　（収率５２％）を得た。Physical property value 1.5-naphthodialdehyde IR (cm""): 1680, 1500.1200°9
20.780 IH-NMRδ (CDCA!3) Near, 6-9.8 (m, 6H, aromaticH
) 10.49 (s, 2H, -CHO) MS: M''=184 Melting point: 192-193°C Example 2 Mixing of 10.0 g (500 mmol) of hydrogen fluoride and 5.40 g (25 mmol) of antimony pentafluoride Add 1.42 g of 1-methylnaphthalene (10
After stirring for 6 hours under a carbon oxide pressure of 20 atm, the reaction solution was poured into water and extracted with benzene to give 0.66 g of 4-methylnaphthaldehyde (yield: 39%).
) and 4-methyl-1,5-naphthodialdehyde 1.0
3 g (yield 52%) was obtained.

物性値 ４−メチル−２，５−ナフトジアルデヒドＩＲ（ｃｍ”
）：１６５５．１２１５．１１７０゜８１５．７８５ ＩＨ−ＮＭＲδ（ＣＤＣ７３）： ３．０８　（ｓ、３Ｈ，−ＣＨ３） ７、　６〜９．４　（ｍ、　　５Ｈ，ａｒｏｍａｔｉｃ
Ｈ）１０．５６　（ｓ、ＩＨ，−ＣＨｏ） １０．７６　（ｓ、ＩＨ，−ＣＨＯ） ＭＳ：Ｍ÷−１９８ 融点＝１５７〜１５８℃ 実施例３ フッ化水素１０．０ｇ　（５００ｍｍｏｌ）と五フッ化
アンチモン５．４０　ｇ　（２５ｍｍｏｌ）の混合溶液
に、０℃で２−メチルナフタレン１．４２ｇ　（１０ｍ
ｍｏｌ）を加え、−酸化炭素圧２０気圧の下で６時間撹
拌した後、反応液を水中に注ぎ、ベンゼンで抽出して、
２−メチルナフトアルデヒド０．４６ｇ（収率２７％）
と、２−メチル−１，５−ナフトジアルデヒド０．　９
９ｇ　（収率５０％）を得た。Physical properties 4-methyl-2,5-naphthodialdehyde IR (cm”
): 1655.1215.1170°815.785 IH-NMRδ (CDC73): 3.08 (s, 3H, -CH3) 7, 6-9.4 (m, 5H, aromatic
H) 10.56 (s, IH, -CHO) 10.76 (s, IH, -CHO) MS: M÷-198 Melting point = 157-158°C Example 3 10.0 g (500 mmol) of hydrogen fluoride and Add 1.42 g (10 mmol) of 2-methylnaphthalene to a mixed solution of 5.40 g (25 mmol) antimony fluoride at 0°C.
After stirring for 6 hours under a carbon oxide pressure of 20 atm, the reaction solution was poured into water and extracted with benzene.
2-methylnaphthaldehyde 0.46g (yield 27%)
and 0.2-methyl-1,5-naphthodialdehyde. 9
9 g (yield 50%) was obtained.

物性値 ２−メチル−１，５−ナフトジアルデヒドＩＲ（ｃｍ−
’）：１６８０，１６７０，１５１０゜１２０５．１１
８０．９２０ ＩＨ−ＮＭＲδ（ＣＤＣ／３）： ２．８５　（ｓ、３Ｈ，−ＣＨ５） ７、４〜９．　６　（ｍ、　　５Ｈ，ａｒｏｍａｉｉｃ
Ｈ）１０．４６　（ｓ、ＩＨ，−ＣＨｏ） １１．０６　（ｓ、ＩＨ，−ＣＨＯ） ＭＳ：Ｍ”＝１９８ 融点：＝１３４〜１３５℃ 実施例４ フッ化水素１０．０ｇ　（５００ｍｍｏｌ）と五フッ化
アンチモン５．４０　ｇ　（２５ｍｍｏｌ）の混合溶液
に、０℃でジフェニル１．　５４　ｇ　（１０ｍｍｏｌ
）を加え、−酸化炭素圧２０気圧の下で２時間撹拌した
後、反応液を水中に注ぎ、ベンゼンで抽出して、４．４
′−ホルミルジフェニル１．７０ｇ　（収率８１％）を
得た。Physical properties 2-methyl-1,5-naphthodialdehyde IR (cm-
'): 1680, 1670, 1510°1205.11
80.920 IH-NMRδ (CDC/3): 2.85 (s, 3H, -CH5) 7, 4-9. 6 (m, 5H, aromaiic
H) 10.46 (s, IH, -CHO) 11.06 (s, IH, -CHO) MS: M'' = 198 Melting point: = 134-135°C Example 4 10.0 g (500 mmol) of hydrogen fluoride Add 1.54 g (10 mmol) of diphenyl to a mixed solution of 5.40 g (25 mmol) of antimony pentafluoride at 0°C.
) and stirred for 2 hours under a carbon oxide pressure of 20 atm, the reaction solution was poured into water and extracted with benzene to obtain 4.4
1.70 g (yield: 81%) of '-formyldiphenyl was obtained.

物性値 ４．４′−ホルミルジフェニル ＩＲ（ｃｍ−’）：１６８５，１５９０，１２００゜１
１５５．９９０．７９５ ＩＨ−ＮＭＲδ（ＣＤＣＡｉ’３）ニ ア、　　７〜８．　３　（ｍ、　８Ｈ，ａｒｏｍａｉｉ
ｃＨ）１０．３０　（ｓ、２Ｈ，−ＣＨＯ） ＭＳ：Ｍ”−２１０ 融点＝１４５〜１４７℃ 実施例５ フッ化水素１０．　０ｇ　（５００ｍｍｏｌ）と五フッ
化アンチモン２．　１６　ｇ　（１０ｍｍｏｌ）の混合
溶液に、０℃で４−メチルジフェニル１．６８ｇ　（Ｉ
Ｑｍｍｏｌ）を加え、−酸化炭素圧２０気圧の下で２時
間撹拌した後、反応液を水中に注ぎ、ベンゼンで抽出し
て、３，４′　−ホルミル−４−メチルジフェニル０．
６１ｇ（収率２７％）を得た。Physical property value 4.4'-Formyldiphenyl IR (cm-'): 1685, 1590, 1200°1
155.990.795 IH-NMRδ (CDCAi'3) Near, 7-8. 3 (m, 8H, aromaii
cH) 10.30 (s, 2H, -CHO) MS: M''-210 Melting point = 145-147°C Example 5 10.0 g (500 mmol) of hydrogen fluoride and 2.16 g (10 mmol) of antimony pentafluoride Add 1.68 g of 4-methyldiphenyl (I
After stirring for 2 hours under a carbon oxide pressure of 20 atm, the reaction solution was poured into water and extracted with benzene to give 3,4'-formyl-4-methyldiphenyl.
61 g (yield 27%) was obtained.

物性値 ３．４′　−ホルミル−４−メチルジフェニルＩＲ（ｃ
ｍ””）：１６８０．１５９５．１１９５゜１１６０．
８００ ＩＨ−ＮＭＲδ（ＣＤＣ７３）： ２．７６　（ｓ、３Ｈ，−ＣＨ５） ７、　２〜８．　２　（ｍ、　　７Ｈ，ｉｒｏｍａｊｉ
ｃＨ）１０．０９　（ｓ、ＩＨ，−ＣＨｏ） １０．３８　（ｓ、ＩＨ，−ＣＨＯ） ＭＳ　：Ｍ”　＝２２４ 融点＝７６〜７８℃ 実施例６ フツ化水素１０．　０ｇ　（５００ｍｍｏｌ）と五フッ
化アンチモン４．　３２　ｇ　（２０ｍｍｏｌ）の混合
溶液に、０℃でジフェニルメタン１．６８ｇ　（ＩＱｍ
ｍｏｌ）を加え、−酸化炭素圧２０気圧の下で２時間撹
拌した後、反応液を水中に注ぎ、ベンゼンで抽出して、
４−ホルミルジフェニルメタン０．０４ｇ（収率２％）
と、４．４’　−ホルミルジフェニルメタン０．４７ｇ
（収率２１％）を得た。Physical property value 3.4'-formyl-4-methyldiphenyl IR (c
m""): 1680.1595.1195°1160.
800 IH-NMRδ (CDC73): 2.76 (s, 3H, -CH5) 7, 2-8. 2 (m, 7H, iromaji
cH) 10.09 (s, IH, -CHO) 10.38 (s, IH, -CHO) MS: M'' = 224 Melting point = 76-78°C Example 6 Hydrogen fluoride 10.0 g (500 mmol) and To a mixed solution of 4.32 g (20 mmol) of antimony fluoride was added 1.68 g of diphenylmethane (IQm
After stirring for 2 hours under a carbon oxide pressure of 20 atm, the reaction solution was poured into water and extracted with benzene.
4-formyldiphenylmethane 0.04g (yield 2%)
and 0.47 g of 4,4'-formyldiphenylmethane
(yield 21%).

物性値 ４．４′−ホルミルジフェニルメタン ＩＲ（ｃｍ”’）：１６８０，１５９５，１２００゜１
１５５．７５５ ＩＨ−ＮＭＲδ（ＣＤＣ７３）： ４、０８　（ｓ、　２Ｈ，ＣＨ２−） ７、　１〜７．８　（ｍ、　８Ｈ，ａｒｏｍａｌｉｃＨ
）９．８７　（ｓ、２Ｈ，−ＣＨＯ） ＭＳ：Ｍ”＝２２４ 融点：６２〜６３℃ 実施例７ フツ化水素１０．０ｇ　（５００ｍｍｏｌ）と五フッ化
アンチモン５．４０　ｇ　（２５ｍｍｏｌ）の混合溶液
に、０℃でジベンジル１．　８２ｇ　（ＩＱｍｍｏｌ）
を加え、−酸化炭素圧２０気圧の下で２時間撹拌した後
、反応液を水中に注ぎ、ベンゼンで抽出して、４．４′
−ホルミルジベンジル２．　３４ｇ　（収率９８％）を
得た。Physical property value 4.4'-Formyldiphenylmethane IR (cm"'): 1680, 1595, 1200°1
155.755 IH-NMRδ (CDC73): 4,08 (s, 2H, CH2-) 7, 1-7.8 (m, 8H, aromaticH
)9.87 (s, 2H, -CHO) MS: M''=224 Melting point: 62-63°C Example 7 Mixing of 10.0 g (500 mmol) of hydrogen fluoride and 5.40 g (25 mmol) of antimony pentafluoride Add 1.82 g (IQ mmol) of dibenzyl to the solution at 0°C.
After stirring for 2 hours under a -carbon oxide pressure of 20 atm, the reaction solution was poured into water and extracted with benzene to give 4.4'
-Formyldibenzyl2. 34 g (yield 98%) was obtained.

物性値 ４．４′−ホルミルジベンジル ＩＲ（ｃｍ−’）：１６８５．１５９５．１２０５゜１
１５５．８０５ ＩＨ−ＮＭＲδ（ＣＤ（、／３）： ３．０７　（ｓ、４Ｈ，−ＣＨ２） ７、　２〜８．　０　（ｍ、　８Ｈ，ａｒｏｍａｆｉｃ
Ｈ）１０．０５　（ｓ、２Ｈ，−ＣＨＯ） ＭＳ　：Ｍ”　＝２３８ 融点＝２９０〜２９２℃ （以　上） 特許出願人　工業技術院長　杉　浦　　　賢指定代理人
　工業技術院大阪工業技術試験所長小見出　　　亨Physical property value 4.4'-formyldibenzyl IR (cm-'): 1685.1595.1205°1
155.805 IH-NMRδ (CD(,/3): 3.07 (s, 4H, -CH2) 7, 2~8.0 (m, 8H, aromafic
H) 10.05 (s, 2H, -CHO) MS: M” = 238 Melting point = 290 to 292°C (or higher) Patent applicant: Director of the Agency of Industrial Science and Technology Ken Sugiura Designated agent: Director of the Osaka Institute of Industrial Science and Technology, Agency of Industrial Science and Technology Heading Toru

Claims (2)

【特許請求の範囲】[Claims] （１）一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿１は、Ｃ＿１〜Ｃ＿３のアルキル基を示す
。〕、 一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿２は、ＨもしくはＣ＿１〜Ｃ＿３のアルキ
ル基を示す。〕 及び一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿３は、Ｃ＿１〜Ｃ＿３のアルキレン鎖を示
す。〕 のいずれかで表される芳香族ジアルデヒド。(1) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R_1 represents an alkyl group of C_1 to C_3. ], General formula ▲ There are numerical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_2 represents H or an alkyl group of C_1 to C_3. [In the formula, R_3 represents an alkylene chain of C_1 to C_3.] and general formula ▲ Numerical formula, chemical formula, table, etc. ] An aromatic dialdehyde represented by any of the following. （２）一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿２は、ＨもしくはＣ＿１〜Ｃ＿３のアルキ
ル基を示す。〕、 一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿２は、前記と同じ。〕 及び一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿３は、Ｃ＿１〜Ｃ＿３のアルキル鎖を示す
。〕 のいずれかで表される芳香族化合物を、フッ化水素と五
フッ化アンチモンとの存在下に一酸化炭素と反応させる
ことを特徴とする一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿２は、前記と同じ。〕、 一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿２は、前記と同じ。〕、 又は一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿３は、前記と同じ。〕 で表される芳香族ジアルデヒドの合成方法。(2) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R_2 represents H or an alkyl group of C_1 to C_3. ], General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_2 is the same as above. ] and general formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R_3 represents an alkyl chain of C_1 to C_3. ] A general formula characterized by reacting an aromatic compound represented by one of the following with carbon monoxide in the presence of hydrogen fluoride and antimony pentafluoride ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ In the formula, R_2 is the same as above. ], General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_2 is the same as above. ], or general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_3 is the same as above. ] A method for synthesizing an aromatic dialdehyde represented by
JP2215985A 1990-08-15 1990-08-15 Method for synthesizing aromatic dialdehyde Expired - Lifetime JP2535742B2 (en)

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WO2012133689A1 (en) * 2011-03-31 2012-10-04 三菱瓦斯化学株式会社 Method for producing 4,4'-diformyldiphenylalkane
CN113149830A (en) * 2021-04-27 2021-07-23 深圳市沃特新材料股份有限公司 Preparation method of 1,4 bis (4-phenoxybenzoyl) benzene and polyether ketone

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JPS6267457A (en) * 1985-09-14 1987-03-27 ベ−リンガ−・マンハイム・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング Method of measuring glycocylated hemoglobin in glood sample
JPS632943A (en) * 1986-06-20 1988-01-07 Sumikin Chem Co Ltd Production of 1-alkyl, 4-formylnaphthalene
JPS63256623A (en) * 1987-04-15 1988-10-24 Hitachi Ltd Polymer with dihydropyridine ring, its production method and uses
JPH01103484A (en) * 1987-10-19 1989-04-20 Mitsui Toatsu Chem Inc Coloring matter for recording material

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Publication number Priority date Publication date Assignee Title
JPS5852247A (en) * 1981-09-24 1983-03-28 Sagami Chem Res Center Preparation of oxocarboxylic acid ester
JPS6267457A (en) * 1985-09-14 1987-03-27 ベ−リンガ−・マンハイム・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング Method of measuring glycocylated hemoglobin in glood sample
JPS632943A (en) * 1986-06-20 1988-01-07 Sumikin Chem Co Ltd Production of 1-alkyl, 4-formylnaphthalene
JPS63256623A (en) * 1987-04-15 1988-10-24 Hitachi Ltd Polymer with dihydropyridine ring, its production method and uses
JPH01103484A (en) * 1987-10-19 1989-04-20 Mitsui Toatsu Chem Inc Coloring matter for recording material

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012133689A1 (en) * 2011-03-31 2012-10-04 三菱瓦斯化学株式会社 Method for producing 4,4'-diformyldiphenylalkane
CN103459360A (en) * 2011-03-31 2013-12-18 三菱瓦斯化学株式会社 Method for producing 4,4'-diformyldiphenylalkane
KR20140027125A (en) * 2011-03-31 2014-03-06 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 Method for producing 4,4'-diformyldiphenylalkane
US8969627B2 (en) 2011-03-31 2015-03-03 Mitsubishi Gas Chemical Company, Inc Method for producing 4,4'-diformyldiphenylalkane
TWI513680B (en) * 2011-03-31 2015-12-21 Mitsubishi Gas Chemical Co Method for producing 4,4'-diformyl diphenylalkane
JP5999371B2 (en) * 2011-03-31 2016-09-28 三菱瓦斯化学株式会社 Method for producing 4,4'-diformyldiphenylalkane
CN113149830A (en) * 2021-04-27 2021-07-23 深圳市沃特新材料股份有限公司 Preparation method of 1,4 bis (4-phenoxybenzoyl) benzene and polyether ketone

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