36978-41-3

Basic information

• Product Name: 2,3,3',4'-BIPHENYL TETRACARBOXYLIC DIANHYDRIDE
• Synonyms: 4,5'-bi-2-benzofuran-1,1',3,3'-tetrone;2,3,3',4'-biphenyl tetraCarbocylic dianhydride;[4,5']BIISOBENZOFURANYL-1,3,1',3'-TETRAONE;2,3,3',4'-BIPHENYL TETRACARBOXYLIC DIANHYDRIDE;1,1'-Biphenyl-2,3,3',4'-tetracarboxylic acid 2,3:3',4'-dianhydride;2,3,3',4'-Biphenyltetracarboxylic 2,3:3',4'-dianhydride;4,5'-Bi(1,3-isobenzofurandione);4,5'-Bi[isobenzofuran]-1,1',3,3'-tetrone
• CAS NO: 36978-41-3
• Molecular Formula: C₁₆H₆O₆
• Molecular Weight: 294.21524
• EINECS: 1592732-453-0
• Product Categories: strong recommend
• Mol File: 36978-41-3.mol

Chemical Properties

• Melting Point: 199 °C
• Boiling Point: 609.3 °C at 760 mmHg
• Flash Point: 275 °C
• Appearance: /
• Density: 1.625 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 2,3,3',4'-BIPHENYL TETRACARBOXYLIC DIANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,3',4'-BIPHENYL TETRACARBOXYLIC DIANHYDRIDE(36978-41-3)
• EPA Substance Registry System: 2,3,3',4'-BIPHENYL TETRACARBOXYLIC DIANHYDRIDE(36978-41-3)

Safety Data

• Hazardous Substances Data: 36978-41-3(Hazardous Substances Data)

Usage

Uses

Used in Polymer Industry:
2,3,3',4'-BIPHENYL TETRACARBOXYLIC DIANHYDRIDE is used as a monomer for the synthesis of polyimide materials due to its high thermal stability and excellent mechanical properties. These polyimide materials are known for their exceptional performance in high-temperature environments and are widely used in applications such as aerospace, electronics, and automotive industries.
Used in Electronics Industry:
In the electronics industry, 2,3,3',4'-BIPHENYL TETRACARBOXYLIC DIANHYDRIDE is used as a precursor for the production of polyimide films and coatings. These materials are valued for their excellent electrical insulation properties, high-temperature resistance, and mechanical strength, making them ideal for use in various electronic components and devices, such as flexible circuits, insulating layers, and protective coatings.
Used in Aerospace Industry:
2,3,3',4'-BIPHENYL TETRACARBOXYLIC DIANHYDRIDE is used as a key component in the development of high-performance composite materials for aerospace applications. The resulting polyimide materials offer superior thermal stability, mechanical strength, and resistance to environmental factors, making them suitable for use in aircraft components, such as heat shields, engine parts, and structural elements.
Used in Automotive Industry:
In the automotive industry, 2,3,3',4'-BIPHENYL TETRACARBOXYLIC DIANHYDRIDE is utilized in the production of polyimide-based materials for high-temperature applications. These materials are employed in components such as engine seals, gaskets, and insulating layers, where their thermal stability and mechanical properties are crucial for performance and reliability.
Overall, 2,3,3',4'-BIPHENYL TETRACARBOXYLIC DIANHYDRIDE plays a significant role in the development and production of polyimide materials across various industries, thanks to its unique properties and versatile applications.

Preparation

The preparation of 2,3,3',4'-biphenyl tetracarboxylic dianhydride is as follows:In a 1000 ml three-necked flask, 18.3 g (0.1 mol) of 4-chlorophthalic anhydride and 18.3 g (0.1 mol) were added 3-chlorophthalic anhydride, 300 g of anisole as solvent, 0.13 g (0.001 mol) of nickel chloride as a catalyst, 0.198 g (0.001 mol) of C-1 as a catalyst ligand, and 0.03 g (0.0003 mol) of sodium bromide as a catalyst Auxiliary, 13 g (0.2 mol) of zinc powder was used as a reducing agent, and the reaction was stirred at 30 ° C for 8 hours under a nitrogen atmosphere. The reaction solution was filtered to remove insoluble solids in the reaction liquid. 300 g of methanol was added to the filtration mother liquor, and the product was precipitated, filtered, and dried to obtain 25.8 g of the product 2,3,3',4'-biphenyltetracarboxylic dianhydride, yield 87.7%.

Upstream product

• 26491-49-6 4-chloro-N-phenyl phthalimide 
• 86-90-8 4-bromophthalic anhydride 
• 82-73-5 3-bromophthalic anhydride 
• 118-45-6 4-chlorophthalic anhydride 
• 117-21-5 3-chlorophthalic anhydride 
• 28418-89-5 4-iodophthalic anhydride 
• 28418-88-4 3-iodophthalic anhydride 
• 67-56-1 methanol 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 36978-40-2 2,3,3′,4′-biphenyl tetracarboxylic dianhydride 

Relevant articles and documents

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 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.

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.

A 2, 3, 3 ', 4' - biphenyl tetracarboxylic acid dianhydride

The invention relates to a 2, 3, 3 ', 4' - biphenyl tetracarboxylic acid dianhydride, 4 - substituted phthalic anhydride and 3 - substituted phthalic anhydride, in a solvent, under protection of inert gas, catalyst, catalyst ligand, catalyst promoter, the presence of a reducing agent reaction, can be under mild condition, one-step reaction for preparing 2, 3, 3 ', 4' - biphenyl tetracarboxylic dianhydride.

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.

PROCESS FOR PRODUCING 2, 3, 3', 4', -BIPHENYLTETRACARBOXYLIC DIANHYDRIDE

2,3,3′,4′-biphenyltetracarboxylic acid is heat-dehydrated in a molten state at a temperature not lower than 200° C. in a flow of an inert gas in a reactor 10 having at least one reaction vessel 11 by stirring the molten material to produce 2,3,3′,4′-biphenyltetracarboxylic dianhydride. Thus obtained 2,3,3′,4′-biphenyltetracarboxylic dianhydride in the molten state is subsequently cooled and solidified in an inert gas or dry air, or cooled and solidified in the ambient air at a temperature of 40° C. or lower or 100° C. or higher.

Process for production of 2, 3, 3', 4'-biphenyltetracarboxylic dianhydride

A process for producing 2,3,3′,4′-biphenyltetracarboxylic dianhydride (a-BPDA), comprising dehydrating 2,3,3′,4′-biphenyltetracarboxylic acid in an inert gas atmosphere under heating at 180 to 195° C is disclosed. This process produces high-purity a-BPDA which is suitable for production of a polyimide.

Diamines and photosensitive polyimides made therefrom

Disclosed is an aromatic diamine having the general formula where A is a group containing at least one aromatic ring, each Y is independently selected from or -OR, R is a group containing at least one olefinically unsaturated group, R' is hydrogen, alkyl to C25, aryl, or R, n is 1 to 4, and the number of olefinic groups in Y is at least 3 when each Y is and otherwise is at least 2. Photosensitive polyamic acids and polyimides can be prepared from the aromatic diamines which can be crosslinked with light to a mask to form patterns on a substrate.

Process for producing biphenyltetracarboxylic dianhydrides

A process for separating and purifying biphenyltetracarboxylic dianhdride isomers from a mixture of these isomers by fractional crystallization in aliphatic acid anhydrides or acetone. The isomeric mixture is obtained by heating biphenyltetracarboxylic acids, optionally in the presence of an aliphatic acid anhydride. The biphenyltetracarboxylic acids are obtained by oxidizing coupling dimers of o-xylene or by hydrolyzing coupling dimers of dimethyl phthalate.