JPH08245501A - Production of aromatic carboxylic acid - Google Patents

Production of aromatic carboxylic acid

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Publication number
JPH08245501A
JPH08245501A JP7051485A JP5148595A JPH08245501A JP H08245501 A JPH08245501 A JP H08245501A JP 7051485 A JP7051485 A JP 7051485A JP 5148595 A JP5148595 A JP 5148595A JP H08245501 A JPH08245501 A JP H08245501A
Authority
JP
Japan
Prior art keywords
acid
salt
palladium
carboxylic acid
aromatic carboxylic
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.)
Withdrawn
Application number
JP7051485A
Other languages
Japanese (ja)
Inventor
Yuzo Fujiwara
祐三 藤原
Ken Takagi
謙 高木
Hiroki Taniguchi
裕樹 谷口
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP7051485A priority Critical patent/JPH08245501A/en
Publication of JPH08245501A publication Critical patent/JPH08245501A/en
Withdrawn legal-status Critical Current

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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

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

Abstract

PURPOSE: To readily obtain the subject compound even under mild conditions according to an industrially excellent method by reacting an aromatic compound with carbon monoxide in the presence of a palladium salt, a peroxy acid salt, etc., and a haloalkylcarboxylic acid. CONSTITUTION: An aromatic compound (e.g, benzene or biphenyl) is reacted with carbon monoxide in the presence of an organic acid salt and/or an inorganic acid salt of palladium [e.g. Pd(NH3 )2 Br2 or Pd(OCOC2 H5 )2 ], a peroxy acid salt (e.g. ammonium peroxydisulfate) and/or oxygen and a haloalkylcarboxylic acid (e.g. trifluoroacetic acid) to afford the objective compound.

Description

【発明の詳細な説明】Detailed Description of the Invention

【０００１】[0001]

【産業上の利用分野】本発明は、芳香族カルボン酸の製
造方法に関し、詳しくは、パラジウムの有機塩及び／又
は無機塩と、ペルオキシ酸の塩及び／又は酸素と、ハロ
アルキルカルボン酸の存在下に、芳香族化合物と一酸化
炭素を反応せしめることを特徴とする芳香族カルボン酸
の製造方法に関するものである。FIELD OF THE INVENTION The present invention relates to a method for producing an aromatic carboxylic acid, more specifically, in the presence of an organic salt and / or an inorganic salt of palladium, a salt of peroxy acid and / or oxygen, and a haloalkylcarboxylic acid. In addition, the present invention relates to a method for producing an aromatic carboxylic acid, which comprises reacting an aromatic compound with carbon monoxide.

【０００２】[0002]

【従来の技術、発明が解決しようとする課題】本発明者
らは、芳香族カルボン酸の製造方法として、酢酸パラジ
ウム又はパラジウム担持炭素の存在下にベンゼンと一酸
化炭素とを140 ℃、20気圧で反応させて安息香酸を製造
する方法を既に提案している（例えば、特開昭62-29463
9 号公報) 。2. Description of the Related Art As a method for producing an aromatic carboxylic acid, the present inventors have proposed that benzene and carbon monoxide are added at 140 ° C. and 20 atm in the presence of palladium acetate or palladium-supporting carbon. Has already been proposed for producing benzoic acid by reacting with (for example, JP-A-62-29463).
No. 9 bulletin).

【０００３】その後、本発明者等は芳香族カルボン酸を
より有利に製造すべく、鋭意検討を重ねた結果、パラジ
ウムの有機塩及び／又は無機塩と、ペルオキシ酸の塩及
び／又は酸素と、ハロアルキルカルボン酸を共存させれ
ば、より温和な条件下でも効率良く芳香族カルボン酸が
製造し得ることを見出すとともに、更に種々の検討を加
えて本発明を完成した。After that, the inventors of the present invention have conducted extensive studies to produce an aromatic carboxylic acid more advantageously, and as a result, organic salt and / or inorganic salt of palladium, salt of peroxy acid and / or oxygen, and It was found that an aromatic carboxylic acid can be efficiently produced even under milder conditions by coexisting with a haloalkylcarboxylic acid, and further various studies were conducted to complete the present invention.

【０００４】[0004]

【課題を解決する手段】すなわち本発明は、パラジウム
の有機塩及び／又は無機塩と、ペルオキシ酸の塩及び／
又は酸素と、ハロアルキルカルボン酸の存在下に、芳香
族化合物と一酸化炭素を反応せしめることを特徴とする
芳香族カルボン酸の工業的に優れた製造方法を提供する
ものである。That is, the present invention provides an organic salt and / or an inorganic salt of palladium and a salt of peroxy acid and / or
Alternatively, the present invention provides an industrially excellent method for producing an aromatic carboxylic acid, which comprises reacting an aromatic compound with carbon monoxide in the presence of oxygen and a haloalkylcarboxylic acid.

【０００５】以下、本発明について詳細に説明する。パ
ラジウムの有機又は無機塩としては、例えばパラジウム
のアセチルアセトナート塩、カルボン酸塩、酸化物、ハ
ロゲン化物、アンモニウム塩、硫酸塩、硝酸塩などの塩
やその配位化合物等が挙げられる。The present invention will be described in detail below. Examples of the organic or inorganic salt of palladium include salts such as acetylacetonate salts, carboxylates, oxides, halides, ammonium salts, sulfates and nitrates of palladium, and coordination compounds thereof.

【０００６】具体化合物としては、例えばPd(NH3)2B
r2 、Pd(NH3)2Cl2 、PdCl2(CH3CN)2 、PdCl2(PhCN)2、P
dCl2(1,5-C8H12)、Pd(O2CCH3)2 、Pd(O2CCF3)2 、Pd(O2
CC3H7)2、Pd(CH3COCHCOCH3)2 、PdBr2 、PdCl2 、Pd
I2、Pd(CN)2 、Pd(NO3)2・xH2O、PdO 、Pd(OCOC2H5)2、
PdSO4・2H2O、Pd(O2CCF3)2 、[Pd(NH3)2](N03)2、Pd(C
H3CN)2(BF4)2、PdCl2[(Ph)3P]2等が例示される。なかで
もPd(O2CCH3)2 、Pd(O2CCF3)2 、Pd(O2CC2H5)2、Pd(O2C
C3H7)2、PdCl2 等が好ましく使用される。Specific compounds include, for example, Pd (NH 3 ) 2 B
r 2 , Pd (NH 3 ) 2 Cl 2 , PdCl 2 (CH 3 CN) 2 , PdCl 2 (PhCN) 2 , P
dCl 2 (1,5-C 8 H 12 ), Pd (O 2 CCH 3 ) 2 , Pd (O 2 CCF 3 ) 2 , Pd (O 2
CC 3 H 7 ) 2 , Pd (CH 3 COCHCOCH 3 ) 2 , PdBr 2 , PdCl 2 , Pd
I 2, Pd (CN) 2 , Pd (NO 3) 2 · xH 2 O, PdO, Pd (OCOC 2 H 5) 2,
PdSO 4 · 2H 2 O, Pd (O 2 CCF 3) 2, [Pd (NH 3) 2] (N0 3) 2, Pd (C
H 3 CN) 2 (BF 4 ) 2, PdCl 2 [(Ph) 3 P] 2 and the like. Among them, Pd (O 2 CCH 3 ) 2 , Pd (O 2 CCF 3 ) 2 , Pd (O 2 CC 2 H 5 ) 2 , Pd (O 2 C
C 3 H 7) 2, PdCl 2 and the like are preferably used.

【０００７】パラジウムの有機又は無機塩の使用量は、
芳香族化合物に対して、通常１×10 -5〜１×10-1モル倍
程度である。The amount of the organic or inorganic salt of palladium used is
Usually 1 x 10 for aromatic compounds -Five~ 1 x 10-1Mole times
It is a degree.

【０００８】またペルオキシ酸の塩としては、例えばペ
ルオキシ硫酸の塩、ペルオキシ燐酸の塩等が挙げられ
る。具体化合物としては、例えばペルオキシ二硫酸アン
モニウム、ペルオキシ二硫酸ナトリウム、ペルオキシ二
硫酸カリウム、ペルオキシ二燐酸カリウム等が例示され
る。その使用量は、パラジウムの有機又は無機塩に対し
て、通常 5〜200 モル当量程度である。ペルオキシ酸の
塩の代わりに酸素も使用し得る。この場合、反応の進行
に応じて供給する方式が通常採用される。Examples of the salt of peroxy acid include salts of peroxysulfuric acid and salts of peroxyphosphoric acid. Examples of specific compounds include ammonium peroxydisulfate, sodium peroxydisulfate, potassium peroxydisulfate, potassium peroxydiphosphate, and the like. The amount used is usually about 5 to 200 molar equivalents with respect to the organic or inorganic salt of palladium. Oxygen may also be used in place of the salt of peroxyacid. In this case, a method of supplying according to the progress of the reaction is usually adopted.

【０００９】ハロアルキルカルボン酸としては、例えば
トリフルオロ酢酸、ジフルオロ酢酸、パーフルオロプロ
ピオン酸等のフルオロアルキルカルボン酸が好ましく使
用される。 その使用量は、触媒mmolあたり通常1 〜20
0ml 程度である。As the haloalkylcarboxylic acid, for example, fluoroalkylcarboxylic acids such as trifluoroacetic acid, difluoroacetic acid and perfluoropropionic acid are preferably used. The amount used is usually 1 to 20 per mmol of the catalyst.
It is about 0 ml.

【００１０】芳香族化合物としては、芳香環に少なくと
も１個置換可能な水素原子を有すものであれば良く、単
環であっても、多環であっても縮合環であっても良い。
単環芳香族化合物としては、例えばベンゼン、トルエ
ン、キシレン、エチルベンゼン、クメン、トリメチルベ
ンゼン、テトラメチルベンゼン等のアルキルベンゼン
類、クロロベンゼン、フルオロベンゼン等のハロゲン化
ベンゼン類、アニソール等のアルコキシベンゼン類が挙
げられる。また多環芳香族化合物としては、例えばビフ
ェニル、ジフェニルメタン、1,2-ジフェニルエタン、1,
3-ジフェニルプロパン等のジフェニルアルカン類、ジフ
ェニルエーテル等のジフェニルエーテル類、これらの誘
導体等が挙げられる。多環芳香族化合物としては、例え
ばナフタレン、メチルナフタレン、ジメチルナフタレ
ン、エチルナフタレン等のナフタレン類、アンスラセ
ン、フェナンスレン、これらの誘導体等が挙げられる。The aromatic compound may be any one having at least one hydrogen atom capable of substituting in the aromatic ring, and may be monocyclic, polycyclic or condensed ring.
Examples of the monocyclic aromatic compound include alkylbenzenes such as benzene, toluene, xylene, ethylbenzene, cumene, trimethylbenzene and tetramethylbenzene, halogenated benzenes such as chlorobenzene and fluorobenzene, and alkoxybenzenes such as anisole. . Examples of polycyclic aromatic compounds include biphenyl, diphenylmethane, 1,2-diphenylethane, 1,
Examples thereof include diphenylalkanes such as 3-diphenylpropane, diphenylethers such as diphenylether, and derivatives thereof. Examples of the polycyclic aromatic compound include naphthalene such as naphthalene, methylnaphthalene, dimethylnaphthalene, ethylnaphthalene, anthracene, phenanthrene, and derivatives thereof.

【００１１】芳香族化合物と一酸化炭素を反応せしめる
にあたっては、常圧または加圧下で通常実施される。一
酸化炭素の圧力は１〜10気圧程度が通常である。 反応
温度は、通常０〜100 ℃程度であり、反応時間は通常１
〜500 時間程度である。反応は常温、常圧でも充分進行
し、効率良く芳香族カルボン酸を製造し得る。The reaction between the aromatic compound and carbon monoxide is usually carried out under normal pressure or pressure. The pressure of carbon monoxide is usually about 1 to 10 atm. The reaction temperature is usually about 0 to 100 ° C, and the reaction time is usually 1
~ 500 hours. The reaction proceeds sufficiently even at room temperature and atmospheric pressure, and an aromatic carboxylic acid can be efficiently produced.

【００１２】かくして、芳香族化合物と一酸化炭素から
芳香族カルボン酸が生成するが、反応後、触媒を常法に
より除去した後、例えば抽出、蒸留等の手段により目的
とする芳香族カルボン酸をを取り出すことができる。Thus, an aromatic carboxylic acid is produced from an aromatic compound and carbon monoxide. After the reaction, the catalyst is removed by a conventional method, and then the desired aromatic carboxylic acid is extracted by means such as extraction or distillation. Can be taken out.

【００１３】[0013]

【発明の効果】本発明方法によれば、芳香族化合物と一
酸化炭素から温和な条件化でも容易に、しかも効率良く
芳香族カルボン酸を製造し得る。According to the method of the present invention, an aromatic carboxylic acid can be easily and efficiently produced from an aromatic compound and carbon monoxide under mild conditions.

【００１４】[0014]

【実施例】以下、本発明を実施例により更に詳細に説明
するが、本発明はこれら実施例に限定されるものではな
い。尚、収率は下式により算出した。 収率（％）＝生成カルボン酸量（モル）／触媒金属量
（モル）×１００EXAMPLES The present invention will now be described in more detail with reference to examples, but the present invention is not limited to these examples. The yield was calculated by the following formula. Yield (%) = amount of produced carboxylic acid (mol) / amount of catalyst metal (mol) × 100

【００１５】実施例１ 100ml のオートクレーブに酢酸パラジウム(Pd(OAc)2 0.
1mmol)、ペルオキソ二硫酸カリウム(K2S2O4 5mmol)、ト
リフルオロ酢酸( 5ml)、ベンゼン56mmolを入れ、25℃、
一酸化炭素を常圧で供給しながら20時間攪拌を続けた。
次いで反応マスを水酸化カリウムの水溶液で処理して、
水層を分液した後、塩酸酸性にして、ジエチルエーテル
で抽出、抽出層を水洗してガスクロマトグラフィーで分
析した。安息香酸の収率は1400％であった。Example 1 Palladium acetate (Pd (OAc) 2 0.
1 mmol), potassium peroxodisulfate (K 2 S 2 O 4 5 mmol), trifluoroacetic acid (5 ml), benzene 56 mmol, and 25 ° C.
The stirring was continued for 20 hours while supplying carbon monoxide at atmospheric pressure.
The reaction mass is then treated with an aqueous solution of potassium hydroxide,
The aqueous layer was separated, acidified with hydrochloric acid and extracted with diethyl ether. The extracted layer was washed with water and analyzed by gas chromatography. The yield of benzoic acid was 1400%.

【００１６】実施例２ 実施例１において、攪拌120 時間続ける以外は実施例１
に準拠して実施した。安息香酸の収率は3300％であっ
た。Example 2 Example 1 was repeated except that the stirring was continued for 120 hours.
It was carried out in accordance with. The yield of benzoic acid was 3300%.

【００１７】実施例３ 実施例１において、ベンゼンの代わりにトルエン56mmol
用いる以外は実施例１に準拠して実施した。メチル安息
香酸の収率は800 ％であり、o,m,p 異性体比は26:6:67
であった。Example 3 In Example 1, 56 mmol of toluene was used instead of benzene.
It implemented based on Example 1 except using it. The yield of methylbenzoic acid was 800%, and the o, m, p isomer ratio was 26: 6: 67.
Met.

【００１８】実施例４ 実施例１において、ベンゼンの代わりにクロロベンゼン
56mmol用いる以外は実施例１に準拠して実施した。クロ
ロ安息香酸の収率は1700％であり、o,m,p 異性体比は1
9:27:54であった。Example 4 In Example 1, chlorobenzene was used instead of benzene.
It carried out based on Example 1 except using 56 mmol. The yield of chlorobenzoic acid was 1700% and the o, m, p isomer ratio was 1
It was 9:27:54.

【００１９】実施例５ 実施例１において、ベンゼンの代わりにアニソール56mm
ol用いる以外は実施例１に準拠して実施した。メトキシ
安息香酸の収率は1700％であり、o,m,p 異性体比は33:
0:67 であった。Example 5 In Example 1, 56 mm anisole was used instead of benzene.
It was carried out in accordance with Example 1 except that ol was used. The yield of methoxybenzoic acid is 1700%, and the o, m, p isomer ratio is 33:
It was 0:67.

【００２０】実施例６ 実施例１において、ベンゼンの代わりにナフタレン56mm
ol用いる以外は実施例１に準拠して実施した。ナフトエ
酸の収率は3300％であり、α, β異性体比は66:34 であ
った。Example 6 In Example 1, naphthalene 56 mm was used instead of benzene.
It was carried out in accordance with Example 1 except that ol was used. The yield of naphthoic acid was 3300%, and the α, β isomer ratio was 66:34.

【００２１】実施例７ 実施例１において、ペルオキソ二硫酸カリウム(K2S2O4
2.5mmol)、トリフルオロ酢酸(1ml) 、ベンゼンの代わり
に1,3-ジフェニルプロパン1000mmol用いる以外は実施例
１に準拠して反応を実施した。次いで反応マスを水酸化
カリウムの水溶液で処理して、水層を分液した後、塩酸
酸性にして、ジエチルエーテル、次いでジクロロメタン
で抽出し、両有機層を合わせて低沸分を留去し、残留物
をジクロロメタン／ジエチルエーテル（容量比1/1)に溶
解してジアソメタンでメチルエステル化し、これをガス
クロマトグラフィーで分析した。モノカルボン酸の収率
は6900％であり、ジカルボン酸の収率は痕跡程度であっ
た。 o,m,p 異性体比は26:10:64であった。Example 7 In Example 1, potassium peroxodisulfate (K 2 S 2 O 4
2.5 mmol), trifluoroacetic acid (1 ml), and the reaction was carried out according to Example 1 except that 1000 mmol of 1,3-diphenylpropane was used instead of benzene. Then, the reaction mass was treated with an aqueous solution of potassium hydroxide, the aqueous layer was separated, acidified with hydrochloric acid, extracted with diethyl ether and then with dichloromethane, both organic layers were combined, and low boiling components were distilled off, The residue was dissolved in dichloromethane / diethyl ether (volume ratio 1/1) and methyl esterified with diazomethane, which was analyzed by gas chromatography. The yield of monocarboxylic acid was 6900%, and the yield of dicarboxylic acid was trace. The o, m, p isomer ratio was 26:10:64.

【００２２】実施例８ 実施例７において、酢酸パラジウム(Pd(OAc)2 0.2mmo
l)、ペルオキソ二硫酸カリウム(K2S2O4 5mmol)、トリフ
ルオロ酢酸(2ml) 、1,3-ジフェニルプロパン1000mmol用
い、攪拌を40時間する以外は実施例７に準拠して実施し
た。ジカルボン酸の収率は7200％であった。pp',op',m
p',oo',om',mm' 異性体比は37:34:15:8:6:<1 であっ
た。Example 8 In Example 7, palladium acetate (Pd (OAc) 2 0.2 mmo
l), potassium peroxodisulfate (K 2 S 2 O 4 5 mmol), trifluoroacetic acid (2 ml) and 1000 mmol of 1,3-diphenylpropane were used, and the stirring was carried out in accordance with Example 7 except for 40 hours. The yield of dicarboxylic acid was 7200%. pp ', op', m
The p ', oo', om ', mm' isomer ratio was 37: 34: 15: 8: 6: <1.

【００２３】実施例９ 実施例１において、ペルオキソ二硫酸カリウム(K2S2O4
2.5mmol)、トリフルオロ酢酸( 1ml)、ベンゼンの代わり
にビフェニル １mmol用いる以外は実施例１に準拠して
実施した。次いで、反応マスにジエチルエーテルを加え
て、苛性カリ水溶液で処理して有機層を分析した。フル
オレノンの収率は100 ％であった。 水層を塩酸酸性に
してジエチルエーテルで抽出、溶媒留去し、残留物をジ
クロロメタン／ジエチルエーテル（容量比１／１）に溶
解してジアゾメタンでメチルエステル化して分析した。
ジカルボン酸の収率は400 ％、モノカルボン酸（p-フ
ェニル安息香酸) の収率は470 ％であった。ジカルボン
酸の異性体比率はNMR により分析したところpp':op'=1
0:1であった。Example 9 In Example 1, potassium peroxodisulfate (K 2 S 2 O 4
2.5 mmol), trifluoroacetic acid (1 ml), and 1 mmol of biphenyl instead of benzene. Then, diethyl ether was added to the reaction mass and treated with an aqueous solution of potassium hydroxide to analyze the organic layer. The yield of fluorenone was 100%. The aqueous layer was acidified with hydrochloric acid, extracted with diethyl ether, the solvent was distilled off, the residue was dissolved in dichloromethane / diethyl ether (volume ratio 1/1), methyl esterified with diazomethane and analyzed.
The yield of dicarboxylic acid was 400%, and the yield of monocarboxylic acid (p-phenylbenzoic acid) was 470%. The isomer ratio of dicarboxylic acid was analyzed by NMR to find that pp ': op' = 1
It was 0: 1.

【００２４】実施例10 実施例１において、ペルオキソ二硫酸カリウムの代わり
に酸素を常圧で供給しながら20時間攪拌した。安息香酸
の収率は100 ％であった。Example 10 In Example 1, stirring was carried out for 20 hours while supplying oxygen at atmospheric pressure instead of potassium peroxodisulfate. The yield of benzoic acid was 100%.

【００２５】比較例１ 実施例１において、トリフルオロ酢酸を用いない以外は
実施例１に準拠して実施した。 安息香酸の生成は認め
られなかった。Comparative Example 1 The procedure of Example 1 was repeated, except that trifluoroacetic acid was not used. No production of benzoic acid was observed.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 // Ｃ０７Ｂ 61/00 ３００ Ｃ０７Ｂ 61/00 ３００ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI technical display location // C07B 61/00 300 C07B 61/00 300

Claims (1)

【特許請求の範囲】[Claims] 【請求項１】パラジウムの有機塩及び／又は無機塩と、
ペルオキシ酸の塩及び／又は酸素と、ハロアルキルカル
ボン酸の存在下に、芳香族化合物と一酸化炭素を反応せ
しめることを特徴とする芳香族カルボン酸の製造方法。1. An organic salt and / or an inorganic salt of palladium,
A process for producing an aromatic carboxylic acid, which comprises reacting an aromatic compound with carbon monoxide in the presence of a peroxy acid salt and / or oxygen and a haloalkylcarboxylic acid.
JP7051485A 1995-03-10 1995-03-10 Production of aromatic carboxylic acid Withdrawn JPH08245501A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP7051485A JPH08245501A (en) 1995-03-10 1995-03-10 Production of aromatic carboxylic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP7051485A JPH08245501A (en) 1995-03-10 1995-03-10 Production of aromatic carboxylic acid

Publications (1)

Publication Number Publication Date
JPH08245501A true JPH08245501A (en) 1996-09-24

Family

ID=12888271

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Application Number Title Priority Date Filing Date
JP7051485A Withdrawn JPH08245501A (en) 1995-03-10 1995-03-10 Production of aromatic carboxylic acid

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Country Link
JP (1) JPH08245501A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111018691A (en) * 2019-11-20 2020-04-17 中国科学技术大学 Green synthesis method of aromatic acid

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111018691A (en) * 2019-11-20 2020-04-17 中国科学技术大学 Green synthesis method of aromatic acid
CN111018691B (en) * 2019-11-20 2022-03-01 中国科学技术大学 Green synthesis method of aromatic acid

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