2420-87-3

Basic information

• Product Name: 3,3',4,4'-Biphenyltetracarboxylic dianhydride
• Synonyms: [1,1'-Biphenyl]-3,3',4,4'-tetracarboxylic3,4:3',4'-dianhydride;3,4,3',4'-Biphenyltetracarboxylic acid dianhydride;3,3',4,4'-Biphenyl tetracarboxylic diandhydride;3,3',4,4'-Biphenyltetracarboxylic dianhydride 97%;4,4'-Biphthalic Anhydride (purified by sublimation);3,3'4,4'-Biphenyl tetracarboxylic acid dianhydride(s-BPDA);3,3',4,4'-Biphenyltetracarboxylic dianhydride (s-BPDA);S-BDPA
• CAS NO: 2420-87-3
• Molecular Formula: C₁₆H₆O₆
• Molecular Weight: 294.22
• EINECS: 219-342-9
• Product Categories: API;strong recommend;Biphenyl & Diphenyl ether;Aromatic Tetracarboxylic Dianhydrides (for High-Performance Polymer Research);Biphenyls (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Monomer for Polyimide film;Anhydride Monomers;Monomers;Polymer Science;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, monomer for polyimide film, pharmaceutical intermediates;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, functional materials
• Mol File: 2420-87-3.mol

Chemical Properties

• Melting Point: 299-305°C
• Boiling Point: 614.9 °C at 760 mmHg
• Flash Point: 277.4 °C
• Appearance: /
• Density: 1.625 g/cm³
• Vapor Pressure: 0Pa at 20℃
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: almost transparency in hot DMF
• CAS DataBase Reference: 3,3',4,4'-Biphenyltetracarboxylic dianhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3',4,4'-Biphenyltetracarboxylic dianhydride(2420-87-3)
• EPA Substance Registry System: 3,3',4,4'-Biphenyltetracarboxylic dianhydride(2420-87-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2420-87-3(Hazardous Substances Data)

Usage

Uses

Used in Polymer Industry:
3,3',4,4'-Biphenyltetracarboxylic dianhydride is used as a monomer for the preparation of polyimide materials. These polyimide materials are known for their high thermal stability, excellent mechanical properties, and good chemical resistance, making them suitable for various applications such as aerospace, electronics, and automotive industries.
Used in Textile Industry:
s-BPDA is used as a monomer in the synthesis of high molecular weight aromatic polyamide fibers. These fibers, commonly known as aramids, exhibit exceptional strength, heat resistance, and chemical stability, making them ideal for applications such as ballistic protection, high-strength ropes, and friction materials.
Used in Nanotechnology:
3,3',4,4'-Biphenyltetracarboxylic dianhydride can be used in the formation of hybrid nanocomposite films. These films combine the properties of s-BPDA with other materials to create innovative products with enhanced performance characteristics, such as improved thermal and mechanical properties, for use in various applications, including electronics and energy storage devices.

Preparation

The preparation of 3,3',4,4'-Biphenyltetracarboxylic dianhydride is as follows:In a nitrogen atmosphere, add N-(3-N,N-dimethylamino-propyl)-4-chlorophthalimide (26.65g, 0.1moL),Zinc powder (3.25g, 0.05moL), anhydrous NiCl2 (127.5mg, 1mmoL),Triphenylphosphine (250mg, 1mmoL) and 70 mL of anhydrous DMAc were stirred at 50°C for 24 hours, and 55mL of solvent DMAc was recovered under reduced pressure. Add 80g of xylene to the system and reflux (recrystallize), filter out the inorganic matter, the clarified filtrate will be cooled and precipitated, filtered, and vacuum dried for 10 hours. 21.8g of 3,3',4,4'-biphenylbisimine was obtained with a yield of 94%. In a 100mL reaction flask, add 4.62g (0.01mol) of the above 3,3',4,4'-biphenylbisimine and 9g of 20% sodium hydroxide aqueous solution, and heat to reflux for 24 hours. Filter and adjust pH=1 with concentrated hydrochloric acid to obtain 3,3’,4,4’-biphenyltetracarboxylic acid. After filtering, wash with water three times and reflux with water with 20mL trimethylbenzene.2.85g of white 3,3′,4,4′-biphenyltetracarboxylic dianhydride was obtained, the yield was 97%.

Flammability and Explosibility

Nonflammable

Upstream product

• 22803-05-0 4,4'-biphthalic acid 
• 4342-61-4 1,2-dichlorotetramethylsilane 
• 1204-28-0 trimellitic anhydride acid chloride 
• 4920-95-0 3,4,3',4'-Tetramethylbiphenyl 
• 6301-60-6 4-iodophthalic acid 
• 36978-37-7 3,3',4,4'-biphenyltetracarboxylic acid tetramethyl ester 
• 59340-47-5 dimethyl 4-iodophthalate 
• 36978-40-2 2,3,3′,4′-biphenyl tetracarboxylic dianhydride 
• 1371598-36-5 3,4-dimethylbiphenyl-3',4'-dicarboxylic acid dimethyl ester 
• 87639-57-4 4-bromophthalic Acid Dimethyl Ester 
• 1371598-37-6 3,4-dicarbomethoxybiphenyl-3',4'-dicarboxylic acid 
• 1371598-38-7 3,4-dicarbomethoxybiphenyl-3',4'-dicarboxylic acid anhydride 
• 1352221-13-6 3,4-dimethoxycarbonylcyclohexyl-3′,4′-dimethylbenzene 
• 7500-55-2 dimethyl cyclohex-4-ene-1,2-dicarboxylate 

Relevant articles and documents

Method for preparing biphenyldianhydride through microwave-assisted catalytic coupling

The invention discloses a method for preparing biphenyldianhydride through microwave-assisted catalytic coupling. In a green solvent 2 - methyltetrahydrofuran (2-THF) system, under microwave irradiation, under microwave irradiation, under a temperature 60 - 95 °C condition, the reaction time is over 20-60 minutes to prepare a biphenyl derivative, and after hydrolysis and dehydration, biphenyldianhydride is obtained. The present invention is characterized in that an organometallic complex is formed by using a halogenated monomer having a complexing action, and zinc halide generated by the reaction with the reaction. It is avoided that its deposition on the reducing agent metal surface results in a reduction in its reducing ability. Compared with the traditional method for preparing the same biphenyl dianhydride, the method is high in reaction speed, the reducing agent is close to the quantitative reaction, and the cost is lower.

Method for preparing and separating and purifying biphenyl derivatives through catalytic coupling

The invention discloses a method for preparing and separating and purifying biphenyl derivatives by catalytic coupling, which mainly comprises the following steps: taking zinc as a reducing agent, carrying out cross-coupling to generate 3 - and 4 - biphenyldianhydrides in an aprotic solvent system and carrying out cross-coupling reaction under the ultrasonic-assisted catalysis to separate the prepared terphenyl derivatives. 3 3 ’ - 4 ’ - 4 ’ - The invention discloses a method for 3 preparing and 4 separating and purifying biphenyl derivatives by using zinc as a reducing agent 3 4 ’ . 3,3 ’ - And 4, 4 ’ - biphenyl derivatives, which are hydrolyzed and dehydrated to obtain three biphenyldianhydride isomer pure products respectively.

Preparation and separation method of biphenyldianhydride isomer

The method mainly comprises the following steps: taking nickel salt as a catalyst, coupling with zinc as a reducing agent, coupling with an aliphatic 3 - chloronaphthalimide and an aryl 4 - chlorosuccinimide mixture as a raw material to generate a biphenyl dianhydride derivative, and separating by using different solubility parameters and obtaining 3 and 4 ’ - respectively. 3,3 ’ - And 4, 4 ’ - biphenyl derivatives are hydrolyzed and dehydrated to obtain three biphenyldianhydride isomers, and the patent application is characterized in that a simple method for separating the three biphenyltetracarboxylic dianhydride intermediate is established.

Method for preparing biphenyldianhydride isomer by ultrasonic-assisted catalytic coupling

The invention discloses a method for preparing biphenyldianhydride isomers through ultrasonic-assisted catalytic coupling. The main contents include a mixture of a nickel salt catalyst and zinc as a reducing agent, 2-THF used as a solvent, an aryl (or methyl) N - chloronaphthalimide and -4 - propyl (or isopropyl) N - chlorodifluoroimide, under -3 - by means of an ultrasonic-assisted catalytic coupling reaction 60 - 100 °C 0.5 - 3 hours. The separation and purification of the three biphenyltetracarboxylic acid isomers are realized by using different solubility parameters, and the biphenyldianhydride isomer pure product is finally obtained. The invention is characterized in that a simple method for separating the three biphenyltetracarboxylic acid isomers is established, the problem of difficulty in separation of the three biphenyl dianhydride mixtures is solved, and 3,4 - biphenyl dianhydride ’ with an asymmetric structure is obtained at lower cost.

Method for preparing biphenyl dianhydride by coupling halogenated phthalimide monomer based on metal coordination

The invention discloses a method for preparing biphenyl dianhydride by coupling halogenated phthalimide monomers based on metal coordination. The method mainly comprises the following steps: by taking halogenated phthalimide with complexing coordination capacity as a raw material, zinc or magnesium as a reducing agent and nickel salt as a catalyst, carrying out coupling reaction in an aprotic solvent system to generate a biphenyl derivative, and hydrolyzing and dehydrating to obtain anhydride. A halogenated monomer with a coordination effect and a by-product zinc halide generated by a reaction form an organic metal complex, and the organic metal complex is dissolved in a reaction system and is prevented from being deposited on the surface of a reducing agent metal to cause reduction of the reducing capacity of the reducing agent metal. Compared with the traditional similar preparation reaction of biphenyl dianhydride, the reducing agent is close to quantitative reaction and is more suitable for industrialization.

Preparation method of 3, 3', 4, 4'-biphenyltetracarboxylic dianhydride

The invention discloses a preparation method of 3, 3', 4, 4'-biphenyltetracarboxylic dianhydride. The method includes the reactions of: (1) chlorination reaction: taking phthalic anhydride as the rawmaterial, adding a mixed solution of sodium hypochlorite aqueous solution and sodium hydroxide aqueous solution dropwise, carrying out chlorination reaction, and adjusting the pH value to generate 4-chlorophthalic acid monosodium salt; (2) coupling and hydrolysis: carrying out coupling reaction and hydrolysis reaction on the 4-chlorophthalic acid monosodium salt in the presence of a catalyst and acocatalyst under an alkaline condition to generate 3, 3', 4, 4'-biphenyltetracarboxylic acid sodium salt, wherein the catalyst is a palladium-carbon catalyst or a nickel-palladium-carbon catalyst, and the cocatalyst is hydroxylamine sulfate or hydroxylamine hydrochloride; and (3) acidification into 3, 3', 4, 4'-biphenyltetracarboxylic acid, and then drying and dehydration, thus obtaining 3, 3', 4, 4'-biphenyltetracarboxylic dianhydride. The method provided by the invention adopts phthalic anhydride as the raw material for reaction with sodium hypochlorite to synthesize 3, 3', 4, 4'-biphenyltetracarboxylic dianhydride, is low in production cost, avoids the use of potassium permanganate oxidation, simplifies the production process, and has small pollution, and high yield.

Synthesis method of 3,3',4,4'-biphenyltetracarboxylic anhydride

The invention discloses a synthesis method of 3,3',4,4'-biphenyltetracarboxylic anhydride, and belongs to the field of chemical synthesis. The synthesis method comprises the following steps: adding 4-bromo-o-xylene into magnesium powder and iodine (simple substance) to obtain a reactant; heating the reactant and 4-chloro-o-xylene to carry out reactions in the presence of nickel acetylacetone taken as the catalyst to obtain 3,3',4,4'-tetramethyl diphenyl, oxidizing and acidifying 3,3',4,4'-tetramethyl diphenyl to obtain 3,3',4,4'-biphenyltetracarboxylic acid, and finally carrying out high temperature dehydration to obtain 3,3',4,4'-biphenyltetracarboxylic anhydride.

METHOD FOR PRODUCING CARBOXYLIC ACID ANHYDRIDE, METHOD FOR PRODUCING CARBOXYLIC IMIDE, AND METHOD FOR MANUFACTURING ELECTROPHOTOGRAPHIC PHOTOSENSITIVE MEMBER

A method for producing a carboxylic acid anhydride includes heating a composition containing a specific compound in a solvent to yield the carboxylic acid anhydride. The solvent is an aprotic polar solvent having a boiling point of 50° C. or more.

Preparation method for biphenyltetracarboxylic dianhydride mixture

The invention relates to a preparation method for a biphenyltetracarboxylic dianhydride mixture. The preparation method comprises the following steps: with phthalic acid as a starting raw material, carrying out an electrophilic substitution reaction so as to produce a phthalic acid derivative; then subjecting the derivative to esterification so as to produce phthalate; further catalyzing phthalate and carrying out a coupling reaction so as to produce a biphenyl tetraformate mixture; and finally, successively carrying out saponification and acidification so as to produce the product biphenyltetracarboxylic dianhydride mixture. The method provided by the invention uses cheap and easily phthalic acid as the starting raw material and is a novel low-cost easily-operatable environment-friendly production method for biphenyltetracarboxylic dianhydride; moreover, isomeric compounds of all the biphenyltetracarboxylic dianhydride are synthesized at one time in the invention, so efficiency is improved and the cost is reduced.

METHOD FOR PRODUCING MULTISUBSTITUTED BIPHENYL COMPOUND AND SOLID CATALYST TO BE USED THEREIN

A method for producing a multisubstituted biphenyl compound is represented by the following formula (2), including a step of coupling a substituted benzene compound represented by the following formula (1) in the presence of a solid catalyst with gold immobilized onto a support.