94-49-5

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1S/C16H14O4/c17-15(13-7-3-1-4-8-13)19-11-12-20-16(18)14-9-5-2-6-10-14/h1-10H,11-12H2

Upstream product

• 75-21-8 oxirane 
• 98-88-4 benzoyl chloride 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 65-85-0 benzoic acid 
• 96-49-1 [1,3]-dioxolan-2-one 
• 93-97-0 benzoic acid anhydride 
• 107-21-1 ethylene glycol 
• 2902-69-4 2,2,2-trichloroacetophenone 
• 532-31-0 silver benzoate 
• 106-93-4 ethylene dibromide 
• 98-87-3 benzylidene dichloride 
• 936-51-6 2-phenyl-1,3-dioxolane 
• 19807-41-1 chlorophenylcarbene 
• 67592-95-4 1,6-diphenyl-2,5,7,8-tetraoxabicyclo<4.2.0>octane 

Downstream Products

• 769-78-8 vinyl benzoate 
• 939-55-9 2-chloroethyl benzoate 
• 65-85-0 benzoic acid 
• 94-33-7 C₉H₁₀O₃ 
• 38353-69-4 2-(acetyloxy)ethyl benzoate 
• 134-81-6 benzil 
• 93-89-0 benzoic acid ethyl ester 
• 582-25-2 Potassium benzoate 
• 22513-32-2 acid sodium salt of benzohydroxamic acid 
• 74-85-1 ethene 
• 93-58-3 benzoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases

Polyethylene terephthalate (PET) is widely used material and as such became highly enriched in nature. It is generally considered inert and safe plastic, but due to the recent increased efforts to break-down PET using biotechnological approaches, we realized the scarcity of information about structural analysis of possible degradation products and their ecotoxicological assessment. Therefore, in this study, 11 compounds belonging to the group of PET precursors and possible degradation products have been comprehensively characterized. Seven of these compounds including 1-(2-hydroxyethyl)-4-methylterephthalate, ethylene glycol bis(methyl terephthalate), methyl bis(2-hydroxyethyl terephtahalate), 1,4-benzenedicarboxylic acid, 1,4-bis[2-[[4-(methoxycarbonyl)benzoyl]oxy]ethyl] ester and methyl tris(2-hydroxyethyl terephthalate) corresponding to mono-, 1.5-, di-, 2,5- and trimer of PET were synthetized and structurally characterized for the first time. In-silico druglikeness and physico-chemical properties of these compounds were predicted using variety of platforms. No antimicrobial properties were detected even at 1000 μg/mL. Ecotoxicological impact of the compounds against marine bacteria Allivibrio fischeri proved that the 6 out of 11 tested PET-associated compounds may be classified as harmful to aquatic microorganisms, with PET trimer being one of the most toxic. In comparison, most of the compounds were not toxic on human lung fibroblasts (MRC-5) at 200 μg/mL with inhibiting concentration (IC50) values of 30 μg/mL and 50 μg/mL determined for PET dimer and trimer. Only three of these compounds including PET monomer were toxic to nematode Caenorhabditis elegans at high concentration of 500 μg/mL. In terms of the applicative potential, PET dimer can be used as suitable substrate for the screening, identification and characterization of novel PET-depolymerizing enzymes.

Expanding the Tool Kit of Automated Flow Synthesis: Development of In-line Flash Chromatography Purification

Recent advancements in in-line extraction and purification technology have enabled complex multistep synthesis in continuous flow reactor systems. However, for the large scope of chemical reactions that yield mixtures of products or residual starting materials, off-line purification is still required to isolate the desired compound. We present the in-line integration of a commercial automated flash chromatography system with a flow reactor for the continuous synthesis and isolation of product(s). A proof-of-principle study was performed to validate the system and test the durability of the column cartridges, performing an automated sequence of 100 runs over 2 days. Three diverse reaction systems that highlight the advantages of flow synthesis were successfully applied with in-line normal- or reversed-phase flash chromatography, continuously isolating products with 97-99% purity. Productivity of up to 9.9 mmol/h was achieved, isolating gram quantities of pure product from a feed of crude reaction mixture. Herein, we describe the development and optimization of the systems and suggest guidelines for selecting reactions well suited to in-line flash chromatography.

Solvent-free synthesis of symmetric methylene diestersviadirect reaction of aromatic carboxylates with 1,n-dihaloalkanes

An efficient methodology for the synthesis of symmetrical methylene diesters was developed through direct reaction of various aromatic carboxylates with 1,n-dihaloalkanes under solvent-free conditions. This strategy offers a high product yield, facile work-up and purification, and an environmentally friendly approach to obtain long-chain methylene carboxylate scaffolds with increased diversity.

Electrochemical esterification via oxidative coupling of aldehydes and alcohols

An electrolytic method for the direct oxidative coupling of aldehydes with alcohols to produce esters is described. Our method involves anodic oxidation in presence of TBAF as supporting electrolyte in an undivided electrochemical cell equipped with graphite electrodes. This method successfully couples a wide range of alcohols to benzaldehydes with yields ranging from 70 to 90%. The protocol is easy to perform at a constant voltage conditions and offers a sustainable alternative over conventional methods.

METHODS FOR DEPOLYMERIZING POLYESTERS

A method for depolymerizing a polyester may comprise heating a polyester at a temperature and for a period of time in the presence of a supported metal-dioxo catalyst, optionally, in the presence of H2, to induce hydrogenolysis of ester groups in the polyester and provide monomers of the polyester.

Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters

The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]

Polyethylene Terephthalate Deconstruction Catalyzed by a Carbon-Supported Single-Site Molybdenum-Dioxo Complex

Polyethylene terephthalate (PET) is selectively depolymerized by a carbon-supported single-site molybdenum-dioxo catalyst to terephthalic acid (PTA) and ethylene. The solventless reactions are most efficient under 1 atmosphere of H2. The catalyst exhibits high stability and can be recycled multiple times without loss of activity. Waste beverage bottle PET or a PET + polypropylene (PP) mixture (simulating the bottle + cap) proceeds at 260 °C with complete PET deconstruction and quantitative PTA isolation. Mechanistic studies with a model diester, 1,2-ethanediol dibenzoate, suggest the reaction proceeds by initial retro-hydroalkoxylation/β-C?O scission and subsequent hydrogenolysis of the vinyl benzoate intermediate.

PROCESS FOR PREPARING A POWDERY ORGANIC PEROXIDE FORMULATION

Process for preparing a powdery organic peroxide formulation, said process comprises the following steps: a) preparing a reaction mixture comprising: - 40-80 wt% water - 10-25 wt% of an acid chloride or chloroformate, - 1 -4 wt% hydrogen peroxide, - 2-8 wt% alkali metal hydroxide, - 1 -25 wt% of a phlegmatizer selected from the group consisting of ethylene glycol dibenzoate, phenyl benzoate, trimethylol propane tribenzoate, glyceryl tribenzoate, ethylene glycol ditoluate, 1,3-propanediol ditoluate, ethylene glycol 4-tert-butylbenzoate, ethylene glycol monobenzoate monotoluate, 2,3- butanediol dibenzoate, 4-methylphenyl benzoate acid ester, trimethylolpropane dibenzoate, and combinations thereof - 0.002-0.20 wt% of a surfactant, and - 0.25-5.0 wt% of an inert organic solvent, all percentages based on the weight of the reaction mixture, b) heating the reaction mixture at a temperature in the range 5-50°C.

A Straightforward Conversion of Activated Amides and Haloalkanes into Esters under Transition-Metal-Free Cs 2 CO 3 /DMAP Conditions

The esterification of activated amides, N -acylsaccharins, under transition-metal-free conditions with good functional group tolerance has been developed, resulting in C-N cleavage leading to efficient synthesis of a variety of esters in moderate to good yields. This work demonstrates that esterification may proceed by using simple N -acylsaccharins, haloalkanes, and Cs 2 CO 3 as oxygen source.

Synthesis of glycol diesters through the depolymerization of polyethylene glycols with carboxylic acids using a proton-exchanged montmorillonite catalyst

A convenient and sustainable method for the synthesis of glycol diesters was developed through the depolymerization of polyethylene glycols (PEGs) with carboxylic acids using proton-exchanged montmorillonite as an efficient solid acid catalyst. Several functionalized glycol diesters were obtained in good yields from PEGs and readily available carboxylic acids. Upon reaction completion, the catalyst could be easily separated by filtration and reused with its activity remaining unchanged.