Integrated process to coproduce aromatic hydrocarbons and ethylene and propylene

A process for producing phenol which comprises producing benzene by

• (a) contacting one or more low molecular weight alkanes, preferably methane, with a halogen, preferably bromine, under process conditions sufficient to produce a monohaloalkane, preferably monobromomethane,
• (b) reacting a first portion of the monohaloalkane in the presence of a coupling catalyst under process conditions sufficient to produce aromatic hydrocarbons and C2-5 alkanes and optionally C2-5 alkenes,
• (c) separating the aromatic hydrocarbons from the product mixture of step (b) to produce aromatic hydrocarbons, and
• (d) reacting a second portion of the monohaloalkane in the presence of a coupling catalyst under process conditions sufficient to produce ethylene and propylene;
• and then either:
• 1) reacting benzene with propylene to produce cumene, oxidizing the cumene to produce cumene hydroperoxide and then hydrolyzing the cumene hydroperoxide in an acidic medium to produce phenol, or
• 2) directly oxidizing benzene using air or oxygen, or
• 3) sulfonating the benzene and then hydrolyzing the sulfonate product, or
• 4) chlorinating the benzene and the hydrolyzing the chlorinated product to produce phenol.

A process for producing styrene which comprises producing benzene by

• (a) contacting one or more low molecular weight alkanes, preferably methane, with a halogen, preferably bromine, under process conditions sufficient to produce a monohaloalkane, preferably monobromomethane,
• (b) reacting a first portion of the monohaloalkane in the presence of a coupling catalyst under process conditions sufficient to produce aromatic hydrocarbons and C2-5 alkanes and optionally C2-5 alkenes,
• (c) separating the aromatic hydrocarbons from the product mixture of step (b) to produce aromatic hydrocarbons, and
• (d) reacting a second portion of the monohaloalkane in the presence of a coupling catalyst under process conditions sufficient to produce ethylene and propylene;
• and then reacting the benzene with ethylene to produce ethylbenzene and then dehydrogenating the ethylbenzene to produce styrene.

A process for producing terephthalic acid which comprises producing paraxylene by

• (a) contacting one or more low molecular weight alkanes, preferably methane, with a halogen, preferably bromine, under process conditions sufficient to produce a monohaloalkane, preferably monobromomethane,
• (b) reacting a first portion of the monohaloalkane in the presence of a coupling catalyst under process conditions sufficient to produce aromatic hydrocarbons and C2-5 alkanes and optionally C2-5 alkenes,
• (c) separating the aromatic hydrocarbons from the product mixture of step (b) to produce aromatic hydrocarbons, and
• (d) reacting a second portion of the monohaloalkane in the presence of a coupling catalyst under process conditions sufficient to produce ethylene and propylene;
• and then oxidizing the paraxylene in the presence of molecular oxygen to produce terephthalic acid.