Fluorine in annual revenue. Due to the danger from direct hydrocarbon–fluorine reactions above −150 °C (−240 °F), industrial fluorocarbon production is indirect, mostly through halogen exchange reactions such as Swarts fluorination, in which chlorocarbon chlorines are substituted for fluorines by hydrogen fluoride under catalysts. Electrochemical fluorination subjects hydrocarbons to electrolysis in hydrogen fluoride, and the Fowler process treats them with solid fluorine carriers like cobalt trifluoride. Halogenated refrigerants, termed Freons in informal contexts, are identified by R-numbers that denote the amount of fluorine, chlorine, carbon, and hydrogen present. Chlorofluorocarbons (CFCs) like R-11, R-12, and R-114 once dominated organofluorines, peaking in production
Chlorine than bromine or iodine. This can be seen from the standard electrode potentials of the X/X couples (F, +2.866 V; Cl, +1.395 V; Br, +1.087 V; I, +0.615 V; At, approximately +0.3 V). However, this trend is not shown in the bond energies because fluorine is singular due to its small size, low polarisability, and lack of low-lying d-orbitals available for bonding (which chlorine has). As another difference, chlorine has a significant chemistry in positive oxidation states while fluorine does not. Chlorination often leads to higher oxidation states than bromination or iodination but lower oxidation states to fluorination. Chlorine tends