The preparation of chlorinated hydrocarbons by reacting a chlorinated alkane substrate, such as 1,1,1,3-tetrachloropropane, with a source of chlorine, such as chlorine (Cl.sub.2), in the presence of a polyvalent molybdenum compound, such as molybdenum pentachloride, is described. With the method of the present invention, the chlorinated alkane product has covalently bonded thereto at least one more chlorine group than the chlorinated alkane substrate, and the chlorinated alkane substrate and the chlorinated alkane product each have a carbon backbone structure that is in each case the same.

Olefins and diolefins, such as 1,3-butiadiene, may be produced by a method utilizing a series of bromination and dehydrobromination reactions. Bromine may be reacted with n-butane to form dibromobutane. The dibromobutanes may be dehydrobrominating to form 1,3-butadiene. The method may include reacting butene with bromine to form bromobutenes, and dehydrobrominating the bromobutenes to form 1,3-butadiene. The method may include reacting butene with hydrogen bromide in the presence of oxygen to form bromobutenes, and dehydrobrominating the bromobutenes to form 1,3-butadiene. The method may include reacting butene with bromine to form dibromobutanes, and dehydrobrominating the dibromobutanes to form 1,3-butadiene.

Olefins and diolefins, such as 1,3-butiadiene, may be produced by a method utilizing a series of bromination and dehydrobromination reactions. Bromine may be reacted with n-butane to form dibromobutane. The dibromobutanes may be dehydrobrominating to form 1,3-butadiene. The method may include reacting butene with bromine to form bromobutenes, and dehydrobrominating the bromobutenes to form 1,3-butadiene. The method may include reacting butene with hydrogen bromide in the presence of oxygen to form bromobutenes, and dehydrobrominating the bromobutenes to form 1,3-butadiene. The method may include reacting butene with bromine to form dibromobutanes, and dehydrobrominating the dibromobutanes to form 1,3-butadiene.

Olefins and diolefins, such as 1,3-butiadiene, may be produced by a method utilizing a series of bromination and dehydrobromination reactions. Bromine may be reacted with n-butane to form dibromobutane. The dibromobutanes may be dehydrobrominating to form 1,3-butadiene. The method may include reacting butene with bromine to form bromobutenes, and dehydrobrominating the bromobutenes to form 1,3-butadiene. The method may include reacting butene with hydrogen bromide in the presence of oxygen to form bromobutenes, and dehydrobrominating the bromobutenes to form 1,3-butadiene. The method may include reacting butene with bromine to form dibromobutanes, and dehydrobrominating the dibromobutanes to form 1,3-butadiene.

Provided is a method for producing a fluorine-containing organic compound. The method can immediately detect the occurrence of a side reaction in direct fluorination reaction using fluorine gas and can give a highly pure fluorine-containing organic compound at a high yield. A raw material liquid (1) containing a raw material organic compound having a hydrogen atom and two or more carbon atoms is reacted with fluorine gas in a reaction container (11) to replace the hydrogen atom of the raw material organic compound with a fluorine atom to give a fluorine-containing organic compound. In the reaction, tetrafluoromethane contained in a gas phase (2) in the reaction container (11) is continuously measured, and the amount of the fluorine gas supplied to the reaction container (11) is controlled depending on the measured value of the tetrafluoromethane.

Provided is a method for producing a fluorine-containing organic compound. The method can immediately detect the occurrence of a side reaction in direct fluorination reaction using fluorine gas and can give a highly pure fluorine-containing organic compound at a high yield. A raw material liquid (1) containing a raw material organic compound having a hydrogen atom and two or more carbon atoms is reacted with fluorine gas in a reaction container (11) to replace the hydrogen atom of the raw material organic compound with a fluorine atom to give a fluorine-containing organic compound. In the reaction, tetrafluoromethane contained in a gas phase (2) in the reaction container (11) is continuously measured, and the amount of the fluorine gas supplied to the reaction container (11) is controlled depending on the measured value of the tetrafluoromethane.

Provided is a method for producing a fluorine-containing organic compound. The method can immediately detect the occurrence of a side reaction in direct fluorination reaction using fluorine gas and can give a highly pure fluorine-containing organic compound at a high yield. A raw material liquid (1) containing a raw material organic compound having a hydrogen atom and two or more carbon atoms is reacted with fluorine gas in a reaction container (11) to replace the hydrogen atom of the raw material organic compound with a fluorine atom to give a fluorine-containing organic compound. In the reaction, tetrafluoromethane contained in a gas phase (2) in the reaction container (11) is continuously measured, and the amount of the fluorine gas supplied to the reaction container (11) is controlled depending on the measured value of the tetrafluoromethane.

Processes for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same. A process for producing 2-chloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the liquid phase in the presence of a fluorination catalyst. A process for producing 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 2-chloro-1,1,1,4,4,4-hexafluorobutane with a chlorine source. A process for producing 1,1,1,4,4,4-hexafluoro-2-butyne comprises contacting 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane with a base. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,1,4,4,4-hexafluoro-2-butyne with hydrogen.

Processes for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same. A process for producing 2-chloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the liquid phase in the presence of a fluorination catalyst. A process for producing 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 2-chloro-1,1,1,4,4,4-hexafluorobutane with a chlorine source. A process for producing 1,1,1,4,4,4-hexafluoro-2-butyne comprises contacting 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane with a base. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,1,4,4,4-hexafluoro-2-butyne with hydrogen.

In one aspect, the disclosure relates to a method for functionalizing hydrocarbons. In a further aspect, the method involves heating a hydrocarbon with a composition having an acid and an oxidant. In other aspects, the composition can further include an iodine-based compound and/or a compound having formula A.sub.aX.sub.n. In any of these aspects, the oxidant can be regenerated in situ or in a separate regeneration step. Also disclosed are functionalized hydrocarbons produced by the disclosed method. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.