JPH0543694B2 - - Google Patents
Info
- Publication number
- JPH0543694B2 JPH0543694B2 JP60231303A JP23130385A JPH0543694B2 JP H0543694 B2 JPH0543694 B2 JP H0543694B2 JP 60231303 A JP60231303 A JP 60231303A JP 23130385 A JP23130385 A JP 23130385A JP H0543694 B2 JPH0543694 B2 JP H0543694B2
- Authority
- JP
- Japan
- Prior art keywords
- amylbenzoyl
- benzoic acid
- amylbenzene
- benzene
- 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.)
- Expired - Lifetime
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 48
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 22
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 claims description 18
- RDQYZLXSZLXNJY-UHFFFAOYSA-N 2-(4-pentylbenzoyl)benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O RDQYZLXSZLXNJY-UHFFFAOYSA-N 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 11
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 10
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 10
- 239000012429 reaction media Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- QHTJSSMHBLGUHV-UHFFFAOYSA-N 2-methylbutan-2-ylbenzene Chemical compound CCC(C)(C)C1=CC=CC=C1 QHTJSSMHBLGUHV-UHFFFAOYSA-N 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010555 transalkylation reaction Methods 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 230000020335 dealkylation Effects 0.000 description 5
- 238000006900 dealkylation reaction Methods 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 2
- UMWZLYTVXQBTTE-UHFFFAOYSA-N 2-pentylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CCCCC)=CC=C3C(=O)C2=C1 UMWZLYTVXQBTTE-UHFFFAOYSA-N 0.000 description 2
- 235000010893 Bischofia javanica Nutrition 0.000 description 2
- 240000005220 Bischofia javanica Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- INPHIYULSHLAHR-UHFFFAOYSA-N 1-pentylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CCCCC INPHIYULSHLAHR-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- -1 amylbenzoyl Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
産業上の利用分野
本発明は２−（4′−アミルベンゾイル）安息香
酸を製造するための改良方法に関するものであ
る。さらに詳しくいえば、本発明は、溶媒中にお
いて、ベンゼン及び塩化アルミニウムの存在下に
アミルベンゼンと無水フタル酸とをフリーデル・
クラフト反応させて、収率よく２−（4′−アミル
ベンゾイル）安息香酸を製造する方法に関するも
のである。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to an improved process for producing 2-(4'-amylbenzoyl)benzoic acid. More specifically, the present invention combines amylbenzene and phthalic anhydride in a solvent in the presence of benzene and aluminum chloride using Friedel's
The present invention relates to a method for producing 2-(4'-amylbenzoyl)benzoic acid in good yield through a craft reaction.
従来の技術
２−（4′−アミルベンゾイル）安息香酸は、各
種有機薬品の中間原料として重要な化合物であ
り、特に過酸化水素の製造に使用される２−アミ
ルアントラキノンを得るための原料として有用な
化合物である。Prior Art 2-(4'-amylbenzoyl)benzoic acid is an important compound as an intermediate raw material for various organic chemicals, and is particularly useful as a raw material for obtaining 2-amyl anthraquinone, which is used in the production of hydrogen peroxide. It is a chemical compound.
この２−（4′−アミルベンゾイル）安息香酸は、
通常クロロベンゼン、ジクロロベンゼン、トリク
ロロベンゼンなどの溶媒中において、無水塩化ア
ルミニウムの存在下に、tert−アミルベンゼンと
無水フタル酸とを反応させることにより得られる
（特開昭48−75558号公報、特開昭53−127445号公
報、米国特許第4035396号明細書）。一方、本発明
者らは、先に塩化アルミニウム−ニトロ化合物錯
体の存在下に、tert−アミルベンゼンと無水フタ
ル酸とを反応させることにより、２−（4′−tert−
アミルベンゾイル）安息香酸の含有率の高い２−
（4′−アミルベンゾイル）安息香酸混合物を製造
する方法を見出した（特願昭60−151号）。しかし
ながら、これらの方法はいずれも収率に関しては
必ずしも満足しうるものではない。 This 2-(4′-amylbenzoyl)benzoic acid is
It is usually obtained by reacting tert-amylbenzene and phthalic anhydride in a solvent such as chlorobenzene, dichlorobenzene, or trichlorobenzene in the presence of anhydrous aluminum chloride (JP-A-48-75558, JP-A-48-75558; Publication No. 53-127445, US Pat. No. 4,035,396). On the other hand, the present inventors discovered that 2-(4'-tert-
2- with a high content of amylbenzoyl) benzoic acid
We have discovered a method for producing a (4'-amylbenzoyl)benzoic acid mixture (Japanese Patent Application No. 1983-151). However, none of these methods is necessarily satisfactory in terms of yield.
ところで、tert−アルキルベンゼンは塩化アル
ミニウムの存在下では、トランスアルキル化、脱
アルキル化及びアルキル基の分子内転位などがこ
の順で起きやすいことや〔工化、第72巻、第1305
ぺージ（1969年）〕、塩化アルミニウムの存在下に
おけるアミルベンゼンの脱アルキル化の速度は、
第三級＞第二級＞第一級アルキル基の順であるこ
と〔工化、第70巻、第918ぺージ（1967年）〕など
が報告されている。 By the way, in the presence of aluminum chloride, tert-alkylbenzene tends to undergo transalkylation, dealkylation, and intramolecular rearrangement of alkyl groups in this order [Koka, Vol. 72, No. 1305]
Page (1969)], the rate of dealkylation of amylbenzene in the presence of aluminum chloride is
It has been reported that the order is tertiary>secondary>primary alkyl group [Koka, Vol. 70, p. 918 (1967)].
また、本発明者らは、１，２−ジクロロエタン
中において、塩化アルミニウムの存在下にtert−
アミルベンゼンと無水フタル酸とを40℃にて４時
間反応した生成物を検討した結果、イソペンタン
及びベンゼンの生成を認めた。さらに生成物を減
圧蒸留し、得られ留分（70〜85℃／３mmHg）を
ガスクロマトグラフイーにより分析したところ、
トランスアルキル化によつて生じたと思われる多
数のピークの存在を認めた。 The present inventors also discovered that tert-
As a result of examining the product obtained by reacting amylbenzene and phthalic anhydride at 40°C for 4 hours, it was found that isopentane and benzene were produced. The product was further distilled under reduced pressure, and the resulting fraction (70-85°C/3mmHg) was analyzed by gas chromatography.
The presence of numerous peaks that appeared to be caused by transalkylation was observed.
これらのことから、明らかにtert−アミルベン
ゼンのアシル化においても、tert−アミルベンゼ
ンのトランスアルキル化や脱アルキル化は避けら
れず、したがつて従来の２−（4′−アミルベンゾ
イル）安息香酸の製造方法では、収率の低下や、
トランスアルキル化によつて生じたジアルキルベ
ンゼンなどと無水フタル酸との反応生成物の生成
は免れない。 From these facts, it is clear that even in the acylation of tert-amylbenzene, transalkylation and dealkylation of tert-amylbenzene are unavoidable, and therefore conventional 2-(4'-amylbenzoyl)benzoic acid In the manufacturing method of
The production of reaction products between dialkylbenzene and the like produced by transalkylation and phthalic anhydride is unavoidable.
発明が解決しようとする問題点
本発明の目的は、このような従来の２−（4′−
アミルベンゾイル）安息香酸の製造方法における
副生物の生成及び収率の低下の問題を解決し、過
酸化水素の製造に用いられる２−アミルアントラ
キノンの出発原料などとして有用な２−（4′−ア
ミルベンゾイル）安息香酸を収率よく製造しうる
工業的に有利な方法を提供することにある。Problems to be Solved by the Invention The purpose of the present invention is to solve the conventional 2-(4'-
2-(4'-amyl benzoyl)benzoic acid is useful as a starting material for 2-amyl anthraquinone used in the production of hydrogen peroxide. The object of the present invention is to provide an industrially advantageous method for producing benzoylbenzoic acid in good yield.
問題点を解決するための手段
本発明者らは前記目的を達成すべく鋭意研究を
重ねた結果、tert−アミルベンゼンのトランスア
ルキル化及び脱アルキル化は、反応媒質中にベン
ゼンを存在させるという極めて簡単な手段により
抑制することができ、その目的を達成しうること
を見出し、この知見に基づいて本発明を完成する
に至つた。Means for Solving the Problems As a result of extensive research to achieve the above object, the present inventors have found that transalkylation and dealkylation of tert-amylbenzene are extremely difficult to achieve in the presence of benzene in the reaction medium. It was discovered that the problem could be suppressed by simple means and the object could be achieved, and based on this knowledge, the present invention was completed.
すなわち、本発明は、溶媒中において、塩化ア
ルミニウムの存在下にアミルベンゼンと無水フタ
ル酸とを反応させて２−（4′−アミルベンゾイル）
安息香酸を製造するに当り、反応媒質としてベン
ゼンを含む混合溶媒を用いることを特徴とする２
−（4′−アミルベンゾイル）安息香酸の製造方法
を提供するものである。 That is, the present invention produces 2-(4'-amylbenzoyl) by reacting amylbenzene and phthalic anhydride in the presence of aluminum chloride in a solvent.
In producing benzoic acid, a mixed solvent containing benzene is used as a reaction medium 2
A method for producing -(4'-amylbenzoyl)benzoic acid is provided.
本発明方法において用いられるベンゼンの添加
量は、通常tert−アミルベンゼン１モルに対し、
0.2〜５モル、好ましくは0.3〜３モルの範囲で選
ばれる。この際のベンゼンは反応媒質中にあらか
じめ含有させておいてもよいし、またtert−アミ
ルベンゼンと共に反応媒質中に加えてもよい。 The amount of benzene used in the method of the present invention is usually 1 mole of tert-amylbenzene.
It is selected in the range of 0.2 to 5 mol, preferably 0.3 to 3 mol. Benzene at this time may be contained in the reaction medium in advance, or may be added to the reaction medium together with tert-amylbenzene.
このようにベンゼンを含む混合溶媒中で反応を
行うことにより、２−（4′−アミルベンゾイル）
安息香酸の製造における低収率の原因であるtert
−アミルベンゼンのトランスアルキル化及び脱ア
ルキル化を抑制することができる。ベンゼンの前
記抑制効果については、本発明者らの研究による
と、例えば１，２−ジクロロエタン中において、
tert−アミルベンゼンと塩化アルミニウムを10℃
で30分間反応させた場合、残存するアミルベンゼ
ンを重量基準で100とすると、イソペンタン7.1、
ベンゼン37.8、ジアルキルベンゼン49.5であるの
に対し、ベンゼンを添加して同様に反応させた場
合、イソペンタン1.7、ジアルキルベンゼン9.3で
ある。 By performing the reaction in a mixed solvent containing benzene in this way, 2-(4'-amylbenzoyl)
tert is responsible for low yields in the production of benzoic acid
- Transalkylation and dealkylation of amylbenzene can be suppressed. Regarding the suppressing effect of benzene, according to the research of the present inventors, for example, in 1,2-dichloroethane,
tert-amylbenzene and aluminum chloride at 10℃
When reacting for 30 minutes at
Benzene is 37.8 and dialkylbenzene is 49.5, whereas when benzene is added and reacted in the same way, isopentane is 1.7 and dialkylbenzene is 9.3.
本発明方法において用いられる反応溶媒として
は、例えばクロロベンゼン、ジクロロベンゼン、
トリクロロベンゼン、ジクロロメタン、ジクロロ
エタン、クロロホルム、テトラクロロエタン、ニ
トロベンゼン、ニトロメタンなど、従来フリーデ
ル・クラフト反応に用いられてきた溶媒が挙げら
れる。 Examples of the reaction solvent used in the method of the present invention include chlorobenzene, dichlorobenzene,
Solvents conventionally used in Friedel-Crafts reactions include trichlorobenzene, dichloromethane, dichloroethane, chloroform, tetrachloroethane, nitrobenzene, and nitromethane.
本発明におけるアミルベンゼンと無水フタル酸
との使用割合については、通常のフリーデル・ク
ラフト反応の場合と同様に、アミルベンゼン１モ
ルに対し1.0〜1.2モルの無水フタル酸を用いるこ
とが好ましい。塩化アルミニウムの使用量は、通
常のフリーデル・クラフト反応の場合と同様に、
アミルベンゼン１モルに対し2.0〜2.2モルの割合
で用いるのが好ましい。 Regarding the ratio of amylbenzene and phthalic anhydride used in the present invention, it is preferable to use 1.0 to 1.2 mol of phthalic anhydride per 1 mol of amylbenzene, as in the case of the usual Friedel-Crafts reaction. The amount of aluminum chloride used is the same as in the normal Friedel-Crafts reaction.
It is preferably used in a proportion of 2.0 to 2.2 moles per mole of amylbenzene.
また反応温度は、通常０〜60℃の範囲で選ばれ
る。反応温度が高すぎるとｏ−ベンゾイル安息香
酸などの副生物が多く生成するで好ましくない。
一方、反応時間は反応温度に左右されが、通常２
〜12時間程度で十分である。 Further, the reaction temperature is usually selected within the range of 0 to 60°C. If the reaction temperature is too high, a large amount of by-products such as o-benzoylbenzoic acid will be produced, which is not preferable.
On the other hand, the reaction time depends on the reaction temperature, but is usually 2
~12 hours is sufficient.
発明の効果
本発明方法によると、反応系にベンゼンを添加
するという極めて簡単な手段により、従来の方法
に比べて高収率で２−（4′−アミルベンゾイル）
安息香酸を得ることができる。このものは各種有
機薬品の中間原料として使用しうることはもちろ
んのこと、特に過酸化水素の製造に使用される２
−アミルアントラキノンを得るための原料として
有用である。Effects of the Invention According to the method of the present invention, 2-(4'-amylbenzoyl) can be produced in a higher yield than in conventional methods by the extremely simple method of adding benzene to the reaction system.
Benzoic acid can be obtained. This product can not only be used as an intermediate raw material for various organic chemicals, but also used in the production of hydrogen peroxide.
- Useful as a raw material for obtaining amyl anthraquinone.
実施例
次に実施例により本発明をさらに詳細に説明す
るが、本発明はこれらの例によつてなんら限定さ
れるものではない。Examples Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples in any way.
実施例 １
１，２−ジクロロエタン2.0モル中に、無水塩
化アルミニウム0.41モル、無水フタル酸0.21モ
ル、tert−アミルベンゼン0.2モル、ベンゼン0.1
モルを加え、10℃で４時間反応させた。反応終了
後、反応液を希酸中に注入して加水分解したの
ち、油層を分取して十分水洗後、稀アルカリ水溶
液で抽出した。次いで、この希アルカリ水溶液を
鉱酸によりPH３に調整して、２−（4′−アミルベ
ンゾイル）安息香酸を析出させたのち、ろ取し、
水洗及び乾燥した。Example 1 In 2.0 moles of 1,2-dichloroethane, 0.41 moles of anhydrous aluminum chloride, 0.21 moles of phthalic anhydride, 0.2 moles of tert-amylbenzene, and 0.1 moles of benzene.
mol was added and reacted at 10°C for 4 hours. After the reaction was completed, the reaction solution was poured into dilute acid for hydrolysis, and then the oil layer was separated, thoroughly washed with water, and then extracted with dilute aqueous alkaline solution. Next, this dilute aqueous alkaline solution was adjusted to pH 3 with mineral acid to precipitate 2-(4'-amylbenzoyl)benzoic acid, which was then collected by filtration.
Washed with water and dried.
得られた２−（4′−アミルベンゾイル）安息香
酸を液体クロマイトグラフイーにより分析した結
果、収率は91％であつた。 The resulting 2-(4'-amylbenzoyl)benzoic acid was analyzed by liquid chromatography, and the yield was 91%.
比較例 １
実施例１において、ベンゼンを添加しないこと
以外は、実施例１と全く同様にして２−（4′−ア
ミルベンゾイル）安息香酸を得た。このものの収
率は80％であつた。Comparative Example 1 2-(4'-amylbenzoyl)benzoic acid was obtained in exactly the same manner as in Example 1, except that benzene was not added. The yield of this product was 80%.
実施例 ２
実施例１におけるベンゼン添加量を0.06モルに
変える以外は、実施例１と全く同様にして２−
（4′−アミルベンゾイル）安息香酸を得た。この
ものの収率は87％であつた。Example 2 2-
(4'-amylbenzoyl)benzoic acid was obtained. The yield of this product was 87%.
実施例 ３
１，２−ジクロロエタン１モル中に、tert−ア
ミルベンゼン0.2モル、ベンゼン0.3モル及び無水
フタル酸0.3モルを加え、次いで30℃に保ち、か
きまぜながら、これに無水塩化アルミニウム0.6
モル、ニトロベンゼン0.6モル及び１，２−ジク
ロロエタン1.0モルから成る塩化アルミニウム−
ニトロベンゼン錯体溶液を30分かけて滴下した。
滴下終了後、50℃まで昇温し、この温度で５時間
反応を行つた。次いで、反応液を実施例１と同様
に処理して、２−（4′−アミルベンゾイル）安息
香酸を78％の収率で得た。Example 3 0.2 mol of tert-amylbenzene, 0.3 mol of benzene and 0.3 mol of phthalic anhydride were added to 1 mol of 1,2-dichloroethane, and then 0.6 mol of anhydrous aluminum chloride was added to this while stirring while maintaining the temperature at 30°C.
mol, aluminum chloride consisting of 0.6 mol of nitrobenzene and 1.0 mol of 1,2-dichloroethane.
The nitrobenzene complex solution was added dropwise over 30 minutes.
After the dropwise addition was completed, the temperature was raised to 50°C, and the reaction was carried out at this temperature for 5 hours. The reaction solution was then treated in the same manner as in Example 1 to obtain 2-(4'-amylbenzoyl)benzoic acid in a yield of 78%.
比較例 ３
実施例３において、ベンゼンを添加しないこと
以外は、実施例３と全く同様にして２−（4′−ア
ミルベンゾイル）安息香酸を得た。このものの収
率は62％であつた。Comparative Example 3 2-(4'-amylbenzoyl)benzoic acid was obtained in exactly the same manner as in Example 3, except that benzene was not added. The yield of this product was 62%.
Claims (1)
にアミルベンゼンと無水フタル酸とを反応させて
２−（4′−アミルベンゾイル）安息香酸を製造す
るに当り、反応媒質としてベンゼンを含む混合溶
媒を用いることを特徴とする２−（4′−アミルベ
ンゾイル）安息香酸の製造方法。1. Using a mixed solvent containing benzene as a reaction medium when producing 2-(4'-amylbenzoyl)benzoic acid by reacting amylbenzene and phthalic anhydride in the presence of aluminum chloride in a solvent. A method for producing 2-(4'-amylbenzoyl)benzoic acid, characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60231303A JPS6293255A (en) | 1985-10-18 | 1985-10-18 | Production of 2-(4'-amylbenzoyl) benzoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60231303A JPS6293255A (en) | 1985-10-18 | 1985-10-18 | Production of 2-(4'-amylbenzoyl) benzoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6293255A JPS6293255A (en) | 1987-04-28 |
| JPH0543694B2 true JPH0543694B2 (en) | 1993-07-02 |
Family
ID=16921507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60231303A Granted JPS6293255A (en) | 1985-10-18 | 1985-10-18 | Production of 2-(4'-amylbenzoyl) benzoic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6293255A (en) |
-
1985
- 1985-10-18 JP JP60231303A patent/JPS6293255A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6293255A (en) | 1987-04-28 |
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