5680-10-4

Usage

Classification

Phthalic acid derivative

Uses

Production of polymers and resins
Crosslinking agent in polyester resins
Manufacture of dyes, pigments, and pharmaceuticals

Toxicity

Low-toxicity compound

Health effects

Limited evidence of adverse health effects from exposure

Safety precautions

Proper handling and safety measures should be followed when working with this chemical

Upstream product

• 17649-59-1 dimethyl 4,5-dimethylphthalate 
• 4430-91-5 2,3-dimethyl-cyclohexa-1,3-diene 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 6433-42-7 1,2-dimethylcyclohexene-4,5-trans-dicarboxylic acid 
• 10564-89-3 1,2-dimethylcyclohexene-4,5-cis-dicarboxylic acid 
• 6096-53-3 dimethyl trans-1,2-dimethylcyclohexene-4,5-dicarboxylate 
• 55264-91-0 dimethyl 1,2-dimethylcyclohexene-4,5-cis-dicarboxylate 
• 95-47-6 o-xylene 
• 201230-82-2 carbon monoxide 
• 26620-46-2 4,5-dimethyl-cyclohex-4-ene-1r,2c-dicarboxylic acid diethyl ester 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 57100-45-5 4,5-Dimethyl-cyclohex-4-ene-1,2-dicarboxylic acid diethyl ester 
• 69094-40-2 diethyl 4,5-dimethylphthalate 
• 5438-24-4 4,5-dimethyl-4-cyclohexene-1,2-dicarboxylic acid anhydride 

Downstream Products

• 619-04-5 3,4-dimethylbenzoic acid 
• 69094-40-2 diethyl 4,5-dimethylphthalate 
• 89-05-4 1,2,4,5-benzenetetracarboxylic acid 
• 4612-57-1 2-bromo-4,5-dimethyl-benzoic acid 
• 5999-20-2 4,5-dimethylphthalic anhydride 
• 25445-42-5 4,5-dimethylbenzene-1,2-dicarbaldehyde 
• 855199-91-6 4,5-dimethyl-2,4'-imino-di-benzoic acid 

Relevant academic research and scientific papers

Highly-functionalized arene synthesis based on palladium on carbon-catalyzed aqueous dehydrogenation of cyclohexadienes and cyclohexenes

Transition metal-catalyzed dehydrogenation is a clean oxidation method requiring no additional oxidants. We have accomplished a heterogeneous Pd/C-catalyzed aqueous dehydrogenation of 1,4-cyclohexadienes and cyclohexenes to give the corresponding highly-functionalized arenes. Furthermore, various arenes could be efficiently constructed in a one-pot manner via a Diels-Alder reaction and the following dehydrogenation.

A method of preparing 1,2,4,5-benzenetetracarboxylic acid or trimellitic acid from pinacol

The invention relates to a method of preparing 1,2,4,5-benzenetetracarboxylic acid or trimellitic acid from pinacol. The method includes a first step of selectively dehydrating the pinacol in an acid/ionic liquid catalytic system to generate 2,-3-dimethyl-1,3-butadiene; a second step of subjecting the 2,-3-dimethyl-1,3-butadiene and maleate or acrylate to a D-A cycloaddition/dehydrogenation tandemreaction to generate an aromatic ring product; and a third step of subjecting the aromatic ring product to hydrolysis and oxidation to prepare the 1,2,4,5-benzenetetracarboxylic acid or the trimellitic acid. The catalytic system adopted in the method is green, and can be recycled. The raw material is a biomass-based platform chemical, and is cheap and easily available. All reaction processes aresimple. The pinacol dehydration reaction, the dehydrogenation reaction of a D-A product and an oxidation reaction are high in activity and selectivity. The novel method for preparing the 1,2,4,5-benzenetetracarboxylic acid and the trimellitic acid which are fine chemicals from the pinacol that is a lignocelluloses based platform chemical is provided by the invention.

Ligand-accelerated non-directed C-H functionalization of arenes

The directed activation of carbon-hydrogen bonds (C-H) is important in the development of synthetically useful reactions, owing to the proximity-induced reactivity and selectivity that is enabled by coordinating functional groups. Palladium-catalysed non-directed C-H activation could potentially enable further useful reactions, because it can reach more distant sites and be applied to substrates that do not contain appropriate directing groups; however, its development has faced substantial challenges associated with the lack of sufficiently active palladium catalysts. Currently used palladium catalysts are reactive only with electron-rich arenes, unless an excess of arene is used, which limits synthetic applications. Here we report a 2-pyridone ligand that binds to palladium and accelerates non-directed C-H functionalization with arene as the limiting reagent. This protocol is compatible with a broad range of aromatic substrates and we demonstrate direct functionalization of advanced synthetic intermediates, drug molecules and natural products that cannot be used in excessive quantities. We also developed C-H olefination and carboxylation protocols, demonstrating the applicability of our methodology to other transformations. The site selectivity in these transformations is governed by a combination of steric and electronic effects, with the pyridone ligand enhancing the influence of sterics on the selectivity, thus providing complementary selectivity to directed C-H functionalization.

Sustainable production of pyromellitic acid with pinacol and diethyl maleate

Herein, we report an unprecedented and sustainable route to synthesize pyromellitic acid (PMA), a monomer of polyimide, with pinacol and diethyl maleate which can be derived from lignocellulose. Analogously, a sustainable route to trimellitic acid (TMA) was also developed using pinacol and acrylate as the feedstocks.

Inclusion complex containing epoxy resin composition for semiconductor encapsulation

The invention is an epoxy resin composition for sealing a semiconductor, including (A) an epoxy resin and (B) a clathrate complex. The clathrate complex is one of (b1) an aromatic carboxylic acid compound, and (b2) at least one imidazole compound represented by formula (II): wherein R2 represents a hydrogen atom, C1-C10 alkyl group, phenyl group, benzyl group or cyanoethyl group, and R3 to R5 represent a hydrogen atom, nitro group, halogen atom, C1-C20 alkyl group, phenyl group, benzyl group, hydroxymethyl group or C1-C20 acyl group. The composition has improved storage stability, retains flowability when sealing, and achieves an effective curing rate applicable for sealing delicate semiconductors.

Dehydro-aromatization of cyclohexene-carboxylic acids by sulfuric acid: Critical route for bio-based terephthalic acid synthesis

A novel dehydro-aromatization reaction under mild reaction conditions was successfully developed using sulfuric acid as a cost-effective and efficient oxidant. This reaction simplified the synthesis of terephthalic acid (TA, an important aromatic monomer precursor) from biomass-derived isoprene and acrylic acid.