19618-93-0

Usage

InChI:InChI=1/C8H10O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-2,5-6H,3-4H2,(H,9,10)(H,11,12)

Upstream product

• 74-85-1 ethene 
• 3588-17-8 trans,trans-muconic acid 
• 1119-73-9 (2Z,4E)-2,4-hexadienedioic acid 
• 124-38-9 carbon dioxide 
• 110-83-8 cyclohexene 
• 1165952-91-9 cyclohexa-1,3-diene 
• 592-46-1 hexa-2,4-diene 
• 74-86-2 acetylene 
• 1659-68-3 cyclohexa-1,3-diene-1,4-dicarboxylic acid 
• 90006-40-9 2,3-dibromo-cyclohexane-1,4-dicarboxylic acid 
• 71195-27-2 trans-dimethyl cyclohex-2-ene-1,4-dicarboxylate 
• 100-21-0 terephthalic acid 

Downstream Products

• 72903-27-6 cyclohexane-1,4-dicarboxylic acid diethyl ester 
• 636-09-9 diethyl terephthalate 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 94-60-0 dimethyl 1,4-cyclohexane dicarboxylate 
• 71195-27-2 cis-dimethyl cyclohex-2-ene-1,4-dicarboxylate 
• 71195-27-2 trans-dimethyl cyclohex-2-ene-1,4-dicarboxylate 
• 110-15-6 succinic acid 
• 100-21-0 terephthalic acid 
• 3399-22-2 dimethyl 1,4-cyclohexanedicarboxylate 
• 1659-68-3 cyclohexa-1,3-diene-1,4-dicarboxylic acid 
• 1659-95-6 dimethyl 1,3-cyclohexadiene-1,4-dicarboxylate 
• 131721-14-7 (Z)-6-[(1R,4R)-((1Z,4Z)-4-Deca-1,4-dienyl)-cyclohex-2-enyl]-hex-5-enoic acid 
• 131721-16-9 (Z)-5-[(1R,4R)-((1Z,4Z)-4-Deca-1,4-dienyl)-cyclohex-2-enyl]-pent-4-enoic acid 
• 131721-15-8 (5Z,8Z)-9-[(1R,4R)-((Z)-4-Hept-1-enyl)-cyclohex-2-enyl]-nona-5,8-dienoic acid 

Relevant academic research and scientific papers

Ni-Catalyzed Site-Selective Dicarboxylation of 1,3-Dienes with CO2

A site-selective catalytic incorporation of multiple CO2 molecules into 1,3-dienes en route to adipic acids is described. This protocol is characterized by its mild conditions, excellent chemo- and regioselectivity and ease of execution under CO2 (1 atm), including the use of bulk butadiene and/or isoprene feedstocks.

METHOD FOR PREPARING DIMETHYL TEREPHTHALATE USING ACETYLENE

The present invention relates to a method for manufacturing dimethyl terephthalate, which uses a cycloaddition reaction using acetylene and dimethyl muconate in one pot unlike existing commercial processes. The manufacturing method according to the present invention is very simple compared with existing methods, can use bio-derived muconic acid and bio-derived acetylene, and thus is eco-friendly, economical, and efficient. The method for manufacturing dimethyl terephthalate comprises the step of obtaining the product of a cycloaddition reaction by inputting dimethyl muconate and acetylene gas into a reactor and making the same react in a solvent.COPYRIGHT KIPO 2015

Electrochemical dicarboxylation of conjugated fatty acids as an efficient valorization of carbon dioxide

Carbon dioxide was electrochemically incorporated in internal conjugated dienes and the process was optimized to achieve satisfactory yields (>70%) even for less reactive substrates. Reactions were performed galvanostatically in an undivided cell at room temperature with a magnesium or aluminium sacrificial anode. Using an optimized electrosynthetic method for the dicarboxylation of 1,3-cyclohexadiene (optimal electrode material, CO2 pressure, amount of charge), the effect of molecular configuration and alkyl substitution on the reactivity of conjugated double bonds towards carboxylation was studied. Use of a bubble reactor at atmospheric pressure instead of a higher pressure reactor, and lowering of the current density made it possible to effectively perform the double carboxylation of internal conjugated double bonds in open chains. Conjugated linoleic acid methyl esters were used in this reaction for the first time and by searching for the optimal reaction conditions (solvent, supporting electrolyte, reactant concentration, amount of charge, current density) yields approaching 80% of the corresponding fatty triacid product could be obtained, at current efficiencies over 50%.

CONTINUOUS DEHYDROGENATION OF 1,4-CARBOXYLATE SUBSTITUTED CYCLOHEXENES

A method which comprises contacting the cyclohexene ring containing compounds having carboxylate derivatives at the 1 and 4, and optionally the 2, positions with one or more dehydrogeoation catalysts, optionally in the presence of one or more oxidants, in a continuous flow mode under conditions such that compounds containing an aromatic ring with carboxylate derivatives at the 1. and 4 positions, and optionally the 2 position, are prepared. The invention also relates to such compounds derived from starting materials derived from renewable resources.

Highly regioselective electrochemical synthesis of dioic acids from dienes and carbon dioxide

A simple and efficient electrochemical method has been developed for highly regioselective synthesis of unsaturated 1,6-dioic acids from 1,3-dienes and CO2. The electrosynthesis was successfully carried out by using a nickel cathode and an aluminum anode in an undivided cell containing n-Bu 4NBr-DMF electrolyte with a constant current under 3 MPa pressure of CO2, and the sole 1,4-addition products were obtained in good to excellent yields. The plausible mechanism for electrodicarboxylation reaction of 1,3-butadiene with CO2 was discussed briefly. In addition, further research shows that 3-hexene-1,6-dioic acid could be easily converted into adipic acid via the electroreduction in the diluted H2SO4 solution.

PREPARATION OF TRANS,TRANS MUCONIC ACID AND TRANS,TRANS MUCONATES

The present invention relates to the isomerization of cis,cis and/or cis,trans muconic acid or esters thereof to trans,trans muconic acid or esters thereof and to the esterification of such muconic acids.

Synthesis of rigidified arachidonic acid analogues

The synthesis of eight arachidonic acid analogues, rigidified by bridging the 7- and 10- or the 10-and 13-bis-allylic positions, is described.