Halogenation

McBee, E. T.

doi:10.1021/ie50465a011

Cited by 6 publications

(5 citation statements)

References 38 publications

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“…The authors do not provide any information about the composition of the residual 41%, thoughgiven the excess of HFit presumably contains over-fluorinated products. Fluorination of vinylidene chloride without a catalyst was examined by McBee, 262 whose protocols call for pressurization to as high as 5000 psig (Scheme 51).…”

Section: Bymentioning

confidence: 99%

“…As many equiv of HgO were added as needed to install the desired number of fluorine atoms. 262 Ferstandig (Halocarbon Products), interested primarily in the preparation of 253fb from 250fb, mentioned that in fluorination reactions with HF/SbCl 5 , an unwanted dehydrochlorination could occur whereby 1,1,1,3-tetrachloropropane was converted to 1,1,3-trichloropropylene (Scheme 72). 317 Such reactions can be minimized by careful monitoring of the concentration of pentavalent antimony in the mixture; the ideal loading of antimony salts in total should be from 8−20% by weight of the total mixture.…”

Section: Hydrochlorofluoropropanes (200-series Hcfcs)mentioning

confidence: 99%

“…In a process reported by McBee, VCl2 was fluorinated in the absence of catalyst to produce a mixture of products among which was 143a. 262 1-Bromo-1-iodoethylene could also be used to the same end. Whalley (ICI) used SnCl 4 to catalyze the conversion of ethylidene dichloride at 70 °C to approximately equal parts of 152a and 151a (40% each, balance starting material).…”

Section: Hydrofluoroethanes (120-to 150-series Hfcs)mentioning

confidence: 99%

“…The authors mention that as the reaction temperature drops, the autoreduction of the Sb catalyst becomes less of an issue, and as such it is desirable for the amount of chlorine co-feed to approach (or preferably reach) Scheme 113. Preparations of 143a 218,262,198 Scheme 114. Synthesis of 134a from 130 483 Scheme 115.…”

Section: Hydrofluoroethanes (120-to 150-series Hfcs)mentioning

confidence: 99%

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Fluorocarbon Refrigerants and their Syntheses: Past to Present

2020

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This Review chronicles the progress made in the field of small fluorocarbon synthesis since their invention in the early 1930s by Thomas Midgley, Jr., and his coworkers, with special focus on their application as refrigerants, foam expansion agents, aerosol propellants, and precision solvents. Divided into four generations of C1–C4 halocarbons from CFCs through HCFCs, HFCs, and HFOs, the merits and challenges of each will be discussed in the context of market demands, as well as the evolution of industrial manufacturing methods. Vital transformations, such as exchange (Swarts) fluorination, hydrodehalogenation, dehydrohalogenation, and additions (Kharasch or Prins) will feature prominently and will be discussed in detail, as well as catalysts therefor. Of the myriad of fluorocarbons described herein, the models which have reached particular commercial significance (such as chlorodifluoromethane and 1,1,1,2-tetrafluoroethane) are given special consideration as flag-bearers for the generation to which they belong. Regulatory constraints to which this industry is bound will be outlined in brief, as well as an introduction to safety designations and nomenclature put forth by the American Society for Heating, Refrigerating, and Air-Conditioning Engineers (ASHRAE). This Review includes predominantly works which can only be found in the patent literature, but should be of equal interest to both academic and industrial practitioners of the art as it centers on fundamentals of organofluorine chemistry, which could equally be applied to the synthesis of larger molecules and building blocks for other applications.

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Section: Bymentioning

confidence: 99%

Section: Hydrochlorofluoropropanes (200-series Hcfcs)mentioning

confidence: 99%

Section: Hydrofluoroethanes (120-to 150-series Hfcs)mentioning

confidence: 99%

Section: Hydrofluoroethanes (120-to 150-series Hfcs)mentioning

confidence: 99%

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Fluorocarbon Refrigerants and their Syntheses: Past to Present

2020

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“…A 15% solution of soda ash, in excess of the calculated quantity, is fed to the hydrolvzer first, and the gravity is adjusted to (18) states that it is believed that most of the benzene hexachloride made industrially today is prepared by a photochemical method. Such a product, according to Cooke (9), contains approximately 8 to 12% of the gamma isomer, which is the one desired.…”

Section: Benzyl Alcohol and Benzaldehydementioning

confidence: 99%

Fine Chemicals From Coal

Shearon¹,

Hall²,

Stevens³

1949

Ind. Eng. Chem.

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The structure of chlorosulfonated polyethylene

Nersasian

Andersen

1960

J of Applied Polymer Sci

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The chlorines in chlorosulfonated polyethylene have been characterized by kinetic analysis according to the method of Salomon. It is found that 2.7% of the total chlorine is primary, 89.8% secondary, 3.5% tertiary, and 4% is sulfonyl chloride. These results are in accord with statistical calculations based on a polyethylene model containing the same methylene‐to‐methyl group ratio as the polyethylene precursor. The types and approximate quantities of dichlorides in the chlorosulfonated polyethylene have been determined by reactions with potassium iodide and zinc dust

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Halogenation

Cited by 6 publications

References 38 publications

Fluorocarbon Refrigerants and their Syntheses: Past to Present

Fluorocarbon Refrigerants and their Syntheses: Past to Present

Fine Chemicals From Coal

The structure of chlorosulfonated polyethylene

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