JPH0210142B2 - - Google Patents
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- Publication number
- JPH0210142B2 JPH0210142B2 JP57139935A JP13993582A JPH0210142B2 JP H0210142 B2 JPH0210142 B2 JP H0210142B2 JP 57139935 A JP57139935 A JP 57139935A JP 13993582 A JP13993582 A JP 13993582A JP H0210142 B2 JPH0210142 B2 JP H0210142B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- general formula
- platinum
- platinum group
- 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
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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
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本発明はハロベンゼンとヒドロキシベンゼンと
一酸化炭素とを、白金族触媒と塩基との共存下に
反応させて安息香酸フエニルエステルを製造する
方法に関するものである。
安息香酸フエニルエステルは耐熱性ポリエステ
ル原料，有機電子材料等の原料として有用であ
る。
従来，安息香酸フエニルエステルは、安息香酸
とフエノールの縮合反応により得られることが知
られているが、複雑な触媒を必要とし、また高価
な脱水剤を使用しなければならず、必ずしも満足
できる収率を得ることはできなかつた。また安息
香酸クロライドとフエノールの縮合反応により得
られることも知られているが、安息香酸クロライ
ドを工業的に有利に得ることが困難であつた。
本発明者は工業的に有利に安息香酸フエニルエ
ステルを得ることを目的に鋭意研究した結果、新
規反応を見出し、本発明に到達した。
すなわち、本発明は、一般式（）
（式中のＸは臭素原子又は沃素原子を示し、Ｒは
アルキル基，アルケニル基，アリール基，シクロ
アルキル基，アルコキシ基，フエノキシ基，アシ
ル基、アシロキシ基，ニトロ基，シアノ基，ホル
ミル基，カルボアルコキシ基及びヒドロキシ基を
示し、ｎは０〜３を示す）で表わされるハロベン
ゼンと、
一般式（）
（式中のＲ及びｎは前記と同じ意味を有する）で
表わされるヒドロキシベンゼンと、一酸化炭素と
を、白金族金属単体または該白金族金属の塩と有
機配位子との錯体からなる群から選ばれた１種の
白金族触媒と塩基との共存下、反応させることを
特徴とする、一般式（）
（式中のＲ及びｎは前記と同じ意味を有する）で
表わされる安息香酸フエニルエステルの製法に関
するものである。
本発明の方法に使用する前記一般式（）で表
わされるハロベンゼンとして、例えばブロモベン
ゼン，ｏ―ブロモトルエン，ｐ―メトキシブロモ
ベンゼン，ｐ―フエノキシブロモベンゼン，ｐ―
ブロモフエノール，ｍ―アセチルブロモベンゼ
ン，酢酸ｐ―ブロモフエニル，ｐ―ニトロブロモ
ベンゼン，ｍ―シアノブロモベンゼン，ｐ―ブロ
モベンズアルデヒド，ヨードベンゼン，ｍ―ヨー
ドトルエン，ｐ―メトキシヨードベンゼン，ｐ―
ヨードフエノール，ｐ―ブロモ安息香酸メチル，
ｏ―ニトロヨードベンゼン，ｍ―ヨードベンズア
ルデヒド，ｐ―シアノヨードベンゼンなどがあげ
られる。
また前記一般式（）で表わされるヒドロキシ
ベンゼンとして、例えばフエノール，ｏ―メトキ
シフエノール，ｐ―メトキシフエノール，ｐ―フ
エノキシフエノール，ハイドロキノン，ｍ―アセ
チルフエノール，レゾルシンモノ酢酸エステル，
ｐ―ニトロフエノール，ｐ―シアノフエノール，
ｐ―ヒドロキシベンズアルデヒド，ｐ―ヒドロキ
シ安息香酸メチルなどがあげられる。
ヒドロキシベンゼンの使用量は、ハロベンゼン
１モルに対して0.1〜10モル倍，特に0.3〜３モル
倍が好ましい。
さらに、一酸化炭素は純粋なガスであつてもよ
いが、必ずしも高純度でなくてもよく窒素ガス，
炭酸ガスなどのような不活性ガスで希釈された混
合ガスを使用してもよい。
一酸化炭素の圧力は常圧で十分であるが、当然
加圧してもよく，通常，0.1〜100Kg／cm2Ｇが適当
である。
本発明の方法に使用する白金族触媒として、(i)
パラジウム、白金、ロジウム、ルテニウム、イリ
ジウム、オスミウムのような白金族金属単体また
は(ii)これらの金属の酢酸塩、硝酸塩、塩化物、臭
化物などのような白金族金属塩と有機配位子との
錯体があげられる。
(i)の白金族金属単体はそれ単独でも使用できる
が、これらの金属を活性炭，グラフアイト，シリ
カゲル，アルミナ，シリカアルミナ，モルキユラ
シーブなどの担体に担持させて使用することもで
きる。また(ii)の白金族金属塩と有機配位子との錯
体として、例えば塩化パラジウム、臭化パラジウ
ム、塩化ロジウム、臭化ルテニウムなどの白金族
金属塩とトリフエニルホスフイン，トリｏ―トリ
ルホスフイン，１，２―ビス（ジフエニルホスフ
イノ）エタン，トリｎ―ブチルホスフイン，トリ
エチルホスフイン，ベンゾニトリル，カルボニル
などとの錯体であるところのPdCl2（Pph3）2，
PdBr2（Pph3）2，Pd（Pph3）4，PdCl2（phCN）2，
Pd（CO）（Pph3）3，RhCl（Pph3）3，RhCl（CO）
（Pph3）2，Pt（CO）2（Pph3）2（ただし，phはフエニ
ル基を示す）などがあげられる。なお場合により
有機配位子を白金族金属塩と錯体を形成する以上
の過剰量加えてもよい。
前記白金族触媒の使用量は、反応媒体に対して
0.01〜10重量％，特に0.05〜２重量％が好まし
い。
また白金族触媒とともに用いられる塩基とし
て、トリエチルアミン，トリｎ―ブチルアミン，
ピリジン，ジメチルアニリン，テトラメチル尿素
のようなアミン類，フエノール類のアルカリ金属
塩及びアルカリ土類金属塩，酢酸ナトリウム，プ
ロピオン酸カリウムのような有機カルボン酸，炭
酸ナトリウム，炭酸カリウム，炭酸水素ナトリウ
ム，酸化カルシウム，水酸化ナトリウム，水酸化
カリウム，水酸化カルシウムのような無機の塩基
などがあげられる。
このような塩基の使用量は、ハロベンゼン１モ
ルに対して0.1〜10モル倍，特に0.3〜３モル倍が
好ましい。
本反応は無溶媒あるいは溶媒中で行われる。溶
媒として、ジエチルエーテル，ジエチレングリコ
ールジエチルエーテル，テトラヒドロフランのよ
うなエーテル類，ベンゼン，トルエン，キシレ
ン，ニトロベンゼン，クロロベンゼンのような芳
香族炭化水素，アセトニトリル，ベンゾニトリル
のようなニトリル類，その他，Ｎ，Ｎ―ジメチル
ホルムアミド，Ｎ，Ｎ―ジメチルアセトアミド，
ジメチルスルホキシド，Ｎ―メチルピロリドン，
ヘキサメチルホスホルアミドなどがあげられる。
反応温度は室温ないし250℃，特に50〜160℃が
好ましい。
本反応は常温，常圧下という極めて温和な反応
条件下で十分に進行する。もちろん高温高圧下に
保持することはさらに本反応を効果的に進行させ
ることができる。
本発明の方法によつて得られる安息香酸フエニ
ルエステルは前記一般式（）によつて表わされ
る化合物であり、その代表例として安息香酸フエ
ニル，ｐ―ヒドロキシ安息香酸フエニル，ｐ―メ
トキシ安息香酸ｐ―メトキシフエニル，ｐ―ヒド
ロキシ安息香酸ｏ―クレジル，ｐ―メトキシ安息
香酸フエニル，ｐ―ヒドロキシ安息香酸ｐ―ヒド
ロキシフエニル，ｐ―ヒドロキシ安息香酸ｍ―ア
セチルフエニル，ｐ―アセトキシ安息香酸ｐ―カ
ルボメトキシフエニル，ｏ―メチル安息香酸ｐ―
ニトロフエニル，ｐ―シアノ安息香酸ｐ―シアノ
フエニル，ｐ―ニトロ安息香酸フエニルなどがあ
げられる。
実施例 １〜７
内容積100mlの回転撹拌式ステンレス鋼製オー
トクレーブに、ハロベンゼン，ヒドロキシベンゼ
ン，白金族触媒，及び塩基，場合により溶媒のそ
れぞれ所定量を充填し、密封後，一酸化炭素を20
気圧圧入し、100℃に保持して1.5〜５時間反応さ
せて安息香酸フエニルエステルを得た。なお副生
成物はほとんど認められなかつた。その結果を第
１表に示す。
The present invention relates to a method for producing phenyl benzoate by reacting halobenzene, hydroxybenzene, and carbon monoxide in the presence of a platinum group catalyst and a base. Benzoic acid phenyl ester is useful as a raw material for heat-resistant polyesters, organic electronic materials, etc. Conventionally, benzoic acid phenyl ester is known to be obtained by the condensation reaction of benzoic acid and phenol, but this method requires a complex catalyst and an expensive dehydrating agent, which is not always satisfactory. No yield could be obtained. It is also known that benzoic acid chloride can be obtained by a condensation reaction of benzoic acid chloride and phenol, but it has been difficult to obtain benzoic acid chloride industrially advantageously. As a result of intensive research aimed at obtaining benzoic acid phenyl ester in an industrially advantageous manner, the present inventor discovered a new reaction and arrived at the present invention. That is, the present invention provides the general formula () (X in the formula represents a bromine atom or an iodine atom, R represents an alkyl group, an alkenyl group, an aryl group, a cycloalkyl group, an alkoxy group, a phenoxy group, an acyl group, an acyloxy group, a nitro group, a cyano group, a formyl group, represents a carbalkoxy group and a hydroxy group, and n represents 0 to 3), and a halobenzene represented by the general formula () (R and n in the formula have the same meanings as above) and carbon monoxide are combined into a group consisting of a simple platinum group metal or a complex of a salt of the platinum group metal and an organic ligand. General formula (), characterized in that the reaction is carried out in the coexistence of one type of platinum group catalyst selected from the following and a base: The present invention relates to a method for producing benzoic acid phenyl ester represented by the formula (R and n have the same meanings as above). Examples of the halobenzene represented by the general formula () used in the method of the present invention include bromobenzene, o-bromotoluene, p-methoxybromobenzene, p-phenoxybromobenzene, p-
Bromophenol, m-acetylbromobenzene, p-bromophenyl acetate, p-nitrobromobenzene, m-cyanobromobenzene, p-bromobenzaldehyde, iodobenzene, m-iodotoluene, p-methoxyiodobenzene, p-
Iodophenol, methyl p-bromobenzoate,
Examples include o-nitroiodobenzene, m-iodobenzaldehyde, and p-cyanoiodobenzene. Further, as the hydroxybenzene represented by the general formula (), for example, phenol, o-methoxyphenol, p-methoxyphenol, p-phenoxyphenol, hydroquinone, m-acetylphenol, resorcin monoacetate,
p-nitrophenol, p-cyanophenol,
Examples include p-hydroxybenzaldehyde and methyl p-hydroxybenzoate. The amount of hydroxybenzene used is preferably 0.1 to 10 times, particularly 0.3 to 3 times by mole, per mole of halobenzene. Furthermore, carbon monoxide may be a pure gas, but does not necessarily have to be of high purity, such as nitrogen gas,
A gas mixture diluted with an inert gas such as carbon dioxide may also be used. Normal pressure is sufficient for the pressure of carbon monoxide, but of course it may be pressurized, and usually 0.1 to 100 kg/cm 2 G is appropriate. As the platinum group catalyst used in the method of the present invention, (i)
Platinum group metals alone such as palladium, platinum, rhodium, ruthenium, iridium, osmium or (ii) platinum group metal salts such as acetates, nitrates, chlorides, bromides, etc. of these metals with organic ligands. Examples include complexes. The platinum group metal (i) can be used alone, but these metals can also be supported on a carrier such as activated carbon, graphite, silica gel, alumina, silica alumina, or molecular sieve. In addition, as a complex of a platinum group metal salt and an organic ligand (ii), for example, a platinum group metal salt such as palladium chloride, palladium bromide, rhodium chloride, or ruthenium bromide and triphenylphosphine, tri-o-tolylphosphine, etc. PdCl 2 (Pph 3 ) 2 which is a complex with yne, 1,2-bis(diphenylphosphino)ethane, tri-n-butylphosphine, triethylphosphine, benzonitrile, carbonyl, etc.
PdBr 2 (Pph 3 ) 2 , Pd (Pph 3 ) 4 , PdCl 2 (phCN) 2 ,
Pd(CO)( Pph3 ) 3 , RhCl( Pph3 ) 3 , RhCl(CO)
(Pph 3 ) 2 , Pt(CO) 2 (Pph 3 ) 2 (where ph represents a phenyl group), etc. In some cases, the organic ligand may be added in an excess amount to form a complex with the platinum group metal salt. The amount of platinum group catalyst used is based on the reaction medium.
0.01-10% by weight, especially 0.05-2% by weight is preferred. In addition, bases used with platinum group catalysts include triethylamine, tri-n-butylamine,
Amines such as pyridine, dimethylaniline, and tetramethylurea, alkali metal and alkaline earth metal salts of phenols, organic carboxylic acids such as sodium acetate and potassium propionate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, Examples include inorganic bases such as calcium oxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide. The amount of such a base to be used is preferably 0.1 to 10 times, particularly 0.3 to 3 times by mole, per mole of halobenzene. This reaction is carried out without a solvent or in a solvent. As a solvent, ethers such as diethyl ether, diethylene glycol diethyl ether, and tetrahydrofuran, aromatic hydrocarbons such as benzene, toluene, xylene, nitrobenzene, and chlorobenzene, nitriles such as acetonitrile and benzonitrile, and others such as N, N- dimethylformamide, N,N-dimethylacetamide,
Dimethyl sulfoxide, N-methylpyrrolidone,
Examples include hexamethylphosphoramide. The reaction temperature is preferably room temperature to 250°C, particularly 50 to 160°C. This reaction proceeds satisfactorily under extremely mild reaction conditions of room temperature and pressure. Of course, maintaining the reaction under high temperature and high pressure allows the reaction to proceed more effectively. The benzoic acid phenyl ester obtained by the method of the present invention is a compound represented by the above general formula (), and representative examples thereof include phenyl benzoate, p-hydroxybenzoic acid phenyl, and p-methoxybenzoic acid phenyl ester. -Methoxyphenyl, p-hydroxybenzoic acid o-cresyl, p-methoxybenzoic acid phenyl, p-hydroxybenzoic acid p-hydroxyphenyl, p-hydroxybenzoic acid m-acetylphenyl, p-acetoxybenzoic acid p- Carbomethoxyphenyl, o-methylbenzoic acid p-
Examples include nitrophenyl, p-cyanophenyl p-cyanobenzoate, phenyl p-nitrobenzoate, and the like. Examples 1 to 7 A rotary stirring type stainless steel autoclave with an internal volume of 100 ml was filled with predetermined amounts of halobenzene, hydroxybenzene, a platinum group catalyst, a base, and optionally a solvent, and after sealing, carbon monoxide was added to the autoclave for 20 minutes.
The mixture was charged under pressure and kept at 100°C to react for 1.5 to 5 hours to obtain benzoic acid phenyl ester. Incidentally, almost no by-products were observed. The results are shown in Table 1.
【表】【table】
【表】
実施例 ８〜11
ガス導入管及び冷却管付きの内容積100mlのフ
ラスコに，ハロベンゼン，ヒドロキシベンゼン，
白金族触媒，及び塩基，場合により溶媒のそれぞ
れ所定量を仕込み，常圧下，一酸化炭素を２／
hrの流速で流通して，100℃で３時間反応させて、
安息香酸フエニルエステルを得た。なお副生成物
はほとんど認められなかつた。その結果を第２表
に示す。[Table] Examples 8 to 11 In a flask with an internal volume of 100 ml equipped with a gas introduction pipe and a cooling pipe, halobenzene, hydroxybenzene,
Predetermined amounts of a platinum group catalyst, a base, and optionally a solvent are charged, and carbon monoxide is evaporated to 2/2% under normal pressure.
Flowed at a flow rate of hr, reacted at 100℃ for 3 hours,
Benzoic acid phenyl ester was obtained. Incidentally, almost no by-products were observed. The results are shown in Table 2.
【表】【table】
Claims (1)
アルキル基、アルケニル基、アリール基、シクロ
アルキル基、アルコキシ基、フエノキシ基、アシ
ル基、アシロキシ基、ニトロ基、シアノ基、ホル
ミル基、カルボアルコキシ基及びヒドロキシ基を
示し、ｎは０〜３を示す）で表わされるハロベン
ゼンと、 一般式（） （式中のＲ及びｎは前記と同じ意味を有する）で
表わされるヒドロキシベンゼンと、一酸化炭素と
を、白金族金属単体または該白金族金属の塩と有
機配位子との錯体からなる群から選ばれた１種の
白金族触媒と塩基との共存下、反応させることを
特徴とする、一般式（） （式中のＲ及びｎは前記と同じ意味を有する）で
表わされる安息香酸フエニルエステルの製造。[Claims] 1 General formula () (X in the formula represents a bromine atom or an iodine atom, R is an alkyl group, an alkenyl group, an aryl group, a cycloalkyl group, an alkoxy group, a phenoxy group, an acyl group, an acyloxy group, a nitro group, a cyano group, a formyl group, represents a carbalkoxy group and a hydroxy group, and n represents 0 to 3), and a halobenzene represented by the general formula () (R and n in the formula have the same meanings as above) and carbon monoxide are combined into a group consisting of a simple platinum group metal or a complex of a salt of the platinum group metal and an organic ligand. General formula (), characterized in that the reaction is carried out in the coexistence of one type of platinum group catalyst selected from the following and a base: Production of benzoic acid phenyl ester represented by the formula (R and n have the same meanings as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57139935A JPS5929641A (en) | 1982-08-13 | 1982-08-13 | Production method of benzoic acid phenyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57139935A JPS5929641A (en) | 1982-08-13 | 1982-08-13 | Production method of benzoic acid phenyl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5929641A JPS5929641A (en) | 1984-02-16 |
| JPH0210142B2 true JPH0210142B2 (en) | 1990-03-06 |
Family
ID=15257088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57139935A Granted JPS5929641A (en) | 1982-08-13 | 1982-08-13 | Production method of benzoic acid phenyl ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5929641A (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6032748A (en) * | 1983-07-29 | 1985-02-19 | Hitachi Ltd | liquid crystal compound |
| JPS60232292A (en) * | 1984-05-02 | 1985-11-18 | Nishihara Environ Sanit Res Corp | Sewage treatment appratus |
| JPH06722B2 (en) * | 1985-02-15 | 1994-01-05 | 旭化成工業株式会社 | Process for producing fluorine-substituted aromatic carboxylic acid aryl ester |
| JPS61293952A (en) * | 1985-06-05 | 1986-12-24 | Sumitomo Chem Co Ltd | Hydroxybenzoate and its manufacturing method |
| JPH0610165B2 (en) * | 1986-02-26 | 1994-02-09 | 旭化成工業株式会社 | Process for producing fluorine-substituted aromatic carboxylic acid aryl ester |
| JPH0610166B2 (en) * | 1986-03-26 | 1994-02-09 | 旭化成工業株式会社 | Process for producing fluorine-substituted aromatic carboxylic acid aryl ester |
| JPH0610167B2 (en) * | 1986-04-08 | 1994-02-09 | 旭化成工業株式会社 | Process for producing fluorine-substituted aromatic carboxylic acid aryl ester |
| JPH0819009B2 (en) * | 1987-03-12 | 1996-02-28 | 日本農薬株式会社 | Method for producing carboxamides |
| JP2832587B2 (en) * | 1987-03-12 | 1998-12-09 | 日本農薬株式会社 | Method for producing carboxylic acid esters |
| JPH0819049B2 (en) * | 1989-05-10 | 1996-02-28 | 工業技術院長 | Dihydrophenanthrenecarboxylic acid ester and method for producing the same |
| JPH0753693B2 (en) * | 1990-10-30 | 1995-06-07 | 工業技術院長 | Method for producing aromatic carboxylic acid esters |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4930339A (en) * | 1972-07-17 | 1974-03-18 | ||
| JPS505347A (en) * | 1973-05-29 | 1975-01-21 |
-
1982
- 1982-08-13 JP JP57139935A patent/JPS5929641A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4930339A (en) * | 1972-07-17 | 1974-03-18 | ||
| JPS505347A (en) * | 1973-05-29 | 1975-01-21 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5929641A (en) | 1984-02-16 |
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