45130-04-9

Upstream product

• 629-27-6 1-Iodooctane 
• 64-17-5 ethanol 
• 124-38-9 carbon dioxide 
• 111-87-5 octanol 
• 105-58-8 Diethyl carbonate 
• 17049-49-9 octylmagnesium bromide 
• 541-41-3 chloroformic acid ethyl ester 
• 104483-19-4 Octyl carbonofluoridate 
• 7452-59-7 octyl chloroformate 

Downstream Products

• 1680-31-5 dioctyl carbonate 

Relevant academic research and scientific papers

Mild and efficient capture and functionalisation of CO2 using silver(i) oxide and application to 13C-labelled dialkyl carbonates

A high yielding three-component reaction between β-iodo ethylamine derivatives, MeOH and gaseous CO2 at ambient temperatures and pressures is reported using silver(i) oxide. Unfunctionalised alkyl iodides were also found to be effective in this transformation and their optimisation is also described. To highlight the ease and control with which gaseous CO 2 can be captured and functionalised under mild conditions, the reaction was performed using 13C-enriched CO2 to afford specifically 13C-carbonyl-labelled dialkyl carbonates with exquisite control of the isotopic purity in good yields and without the need for specialised equipment.

Synthesis of ethyl octyl ether from diethyl carbonate and 1-octanol over solid catalysts. A screening study

The synthesis of ethyl octyl ether (EOE) from a mixture of diethyl carbonate (DEC) and 1-octanol (1:2 molar ratio) over several solid catalysts was studied in batch mode at 150 °C and 25 bar. Catalyst screening revealed that EOE could be successfully obtained over some acid catalysts. In particular the highest yield was achieved over acid ion-exchange resins (33% after 8 h). A reaction scheme of the process is proposed. Selectivity to EOE was mainly affected by the production of diethyl ether (DEE) and di-n-octyl ether (DNOE). However, EOE was the main ether obtained (60 mol%), followed by DEE (20 mol%) and DNOE (20 mol%). By comparing the behavior of several acid resins, it was seen that the synthesis of EOE was highly related to the structural resin properties. It was found that the accessibility of DEC and 1-octanol to acid centers was improved over highly swollen and low polymer density resins. Thus, gel-type resins with low divinylbenzene content are the most suitable to produce EOE (e.g., Amberlyst 121, Dowex 50Wx2-100 and CT224).

The continuous acid-catalysed etherification of aliphatic alcohols using stoichiometric quantities of dialkyl carbonates

A range of methyl and ethyl ethers of aliphatic alcohols have been synthesized cleanly in high yield by reacting the corresponding alcohol with dimethyl carbonate or diethyl carbonate over the solid acid catalyst, I-alumina. The reaction could be conducted at ambient pressure without the need for the large excess of dialkyl carbonate as previously reported in the literature. If the reaction was conducted at high pressure, the conversion of the starting alcohol was greatly reduced. However, high pressure CO2 can be used as the solvent without significant reduction in yield. This has implications for tandem reactions.

A new versatile synthesis of esters from Grignard reagents and chloroformates

Cross-coupling reactions of chloroformates with organocopper reagents, derived from Grignard reagents, cuprous bromide and lithium bromide, provide a rapid and straightforward method for the synthesis of esters. Georg Thieme Verlag Stuttgart.

Correlation of the rates of solvolysis of n-octyl fluoroformate and a comparison with n-octyl chloroformate solvolysis

The specific rates of solvolysis of n-octyl fluoroformate have been measured at 24.2°C in 28 pure and binary solvents. For the 23 solvents for which both NT(solvent nucleophilicity) and YCl (solvent ionizing power) values are known, a correlation using the two-term Grunwald-Winstein equation leads to sensitivities towards changes in the two scales of 1.80 ± 0.13 (l value) and 0.79 ± 0.06 (m value), respectively. For seven solvents, a parallel study was made of n-octyl chloroformate solvolysis and F:Cl specific rate ratios were, in most instances, above unity, consistent with the association step of an association-dissociation (addition-elimination) pathway being rate-determining.

ORGANIC SYNTHESES WITHOUT SOLVENT: BASE-CATALYSED ESTER INTERCHANGE

Ester interchange of methyl or ethyl carboxylic esters by primary or secondary alcohols is carried out effectively when solid-liquid phase transfer catalysis (PTC) is achieved in the absence of added organic solvent.Vinyl and isopropenyl acetates undergo ester interchange, even in the absence of PTC catalyst, with primary alcohols and phenols.