461-57-4

Usage

Physical state

Colorless liquid

Odor

Mild, ether-like

Primary uses

a. Solvent
b. Refrigerant in industrial applications

Environmental properties

a. Low global warming potential
b. Non-ozone depleting

Environmental benefits

More environmentally friendly alternative to traditional refrigerants

Toxicity

Low toxicity

Safety

Considered safe for use in various applications

Potential alternative

To high-global-warming-potential hydrofluorocarbons in air conditioning and refrigeration systems

Upstream product

• 359-07-9 2-bromo-1,1-difluoroethane 
• 124-41-4 sodium methylate 
• 75-02-5 1-fluoroethylene 
• 36336-08-0 methyl hypofluorite 
• 135206-84-7 2,2-difluoroethyl 4-methylbenzenesulfonatemethyl6-bromo-3-(2,2-difluoroethoxy)picolinate 
• 74-87-3 methylene chloride 

Downstream Products

• 381-73-7 Difluoroacetic acid 

Relevant academic research and scientific papers

Method for preparing hydrofluoroether through two-step process

The invention discloses a method for preparing hydrofluoroether through a two-step process. With the method provided by the invention, p-toluensulfonyl chloride and fluorine-containing alcohol are subjected to a reaction to obtain p-toluenesulfonate, and the p-toluenesulfonate and sodium alkoxide are subjected to a Williamson ether synthetic reaction to obtain the hydrofluoroether. The method disclosed by the invention has the advantages of cheap and low-toxicity raw materials, mild and controllable reaction conditions, and high yield.

Hydrogen bonding lowers intrinsic nucleophilicity of solvated nucleophiles

The relationship between nucleophilicity and the structure/environment of the nucleophile is of fundamental importance in organic chemistry. In this work, we have measured nucleophilicities of a series of substituted alkoxides in the gas phase. The functional group substitutions affect the nucleophiles through ion-dipole, ion-induced dipole interactions and through hydrogen bonding whenever structurally possible. This set of alkoxides serves as an ideal model system for studying nucleophiles under microsolvation settings. Marcus theory was applied to analyze the results. Using Marcus theory, we separate nucleophilicity into two independent components, an intrinsic nucleophilicity and a thermodynamic driving force determined solely by the overall reaction exothermicity. It is found that the apparent nucleophilicities of the substituted alkoxides are always much lower than those of the unsubstituted ones. However, ion-dipole, ion-induced dipole interactions, by themselves, do not significantly affect the intrinsic nucleophilicity; the decrease in the apparent nucleophilicity results from a weaker thermodynamic driving force. On the other hand, hydrogen bonding not only stabilizes the nucleophile but also increases the intrinsic barrier height by 3 to ～4 kcal mol-1. In this regard, the hydrogen bond is not acting as a perturbation in the sense of an external dipole but more directly affects the electronic structure and reactivity of the nucleophilic alkoxide. This finding offers a deeper insight into the solvation effect on nucleophilicity, such as the remarkably lower reactivities in nucleophilic substitution reactions in protic solvents than in aprotic solvents.

Methyl hypofluorite (MeOF) reactions with various fluoroolefins

The reaction of methyl hypofluorite (MeOF) with certain fluoroolefins, such as CF2=CF2, CF2=CFCF3, CF2=CFOCF3, CF2=CFOMe, CF2=CClF, CF2=CHF, CF2=CH2, CHF=CH2, CF2=CFCF=CF2, occurred in CD3CN or in the presence of NaF. Using neat MeOF in the presence of NaF was a novel method and gave good results. We observed that when more than three fluorine atoms are bonded to the C-C double bond, the addition products were obtained in mostly good yields.