Carbonylation process
AssigneeUop LLC
InventorsLance A. Baird, Leonid B. Galperin, R. Joe Lawson, Robert H. Jensen, Oleg L. Eliseev, Albert L. Lapidus, Aduard G. Ostapenco
Life of this patent
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Abstract
Long chain alcohols and acids or other similar oxygenates such as esters are produced from paraffins of similar carbon number by a process comprising paraffin dehydrogenation, carbonylation, and separation. Preferably a mixture of paraffins extending over several carbon numbers and recovered from a kerosene fraction is processed, and unconverted paraffins are recycled to a dehydrogenation zone. Alternative reaction zone configurations, catalyst systems and product recovery methods are disclosed.
Claims30
A continuous process for the production of oxygenated hydrocarbons which comprises:
- (a) passing a feed stream comprising at least two different paraffinic hydrocarbons, each having a carbon number above 6, into a dehydrogenation zone operated at dehydrogenation conditions and converting a least a portion of the entering paraffinic hydrocarbons to olefinic hydrocarbons of the same carbon number to form a dehydrogenation zone effluent stream comprising a mixture of olefinic and paraffinic hydrocarbons;
- (b) passing at least a portion of the hydrocarbons of said dehydrogenation zone effluent stream, carbon monoxide and a hydroxyl-supplying feed compound chosen from water and a light alcohol into contact with a homogeneous carbonylation catalyst in a carbonylation zone operated at carbonylation conditions and converting at least a portion of said olefinic hydrocarbons to desired carbonylation products, and recovering a process stream comprising carbonylation products and paraffinic hydrocarbons from the carbonylation zone;
- (c) passing said process stream into a fractional distillation zone in which the process stream is separated into at least a hydrocarbon recycle stream comprising paraffinic hydrocarbons and an oxygenate stream comprising carbonylation products recycling the hydrocarbon recycle stream to the dehydrogenation zone;
- and,
- (d) recovering the carbonylation products.
A process for the production of oxygenated hydrocarbons which comprises:
- (a) passing a feed stream comprising a mixture of different paraffinic feed hydrocarbons having carbon numbers above 6 into a dehydrogenation zone operated at dehydrogenation conditions and converting a fractional portion of the entering paraffinic hydrocarbons into olefinic hydrocarbons of the same carbon number as the corresponding feed hydrocarbons to form a dehydrogenation zone effluent stream comprising a mixture of olefinic and paraffinic hydrocarbons;
- (b) passing said dehydrogenation zone effluent stream, carbon monoxide and water into contact with a homogeneous carbonylation catalyst in a carbonylation zone operated at carbonylation conditions and converting at least a portion of said olefinic hydrocarbons to carboxylic acids, and recovering a product stream comprising carboxylic acids and paraffinic hydrocarbons from the carbonylation zone;
- (c) passing said product stream into a product recovery zone comprising a fractional distillation zone to yield at least a hydrocarbon recycle stream comprising paraffinic hydrocarbons and an acid stream comprising carboxylic acids originally present in the product stream;
- (d) recycling the hydrocarbon recycle stream to the dehydrogenation zone;
- and,
- (e) withdrawing the acid stream from the process.
A process for the production of oxygenated hydrocarbons which comprises:
- (a) passing a feed stream comprising a mixture of different acyclic paraffinic feed hydrocarbons having carbon numbers above 6 into a dehydrogenation zone operated at dehydrogenation conditions and converting a fractional portion of the entering paraffinic hydrocarbons into olefinic hydrocarbons of the same carbon number as the corresponding feed hydrocarbons to form a dehydrogenation zone effluent stream comprising a mixture of acyclic olefinic and paraffinic hydrocarbons;
- (b) passing at least a portion of said dehydrogenation zone effluent stream, carbon monoxide and water into contact with a homogeneous carbonylation catalyst system comprising a palladium triphenyl phosphine complex or a palladium imidazole complex, formic acid and lithium iodide in a carbonylation zone operated at carbonylation conditions and converting at least a portion of said olefinic hydrocarbons to carboxylic acids, and recovering a product stream comprising carboxylic acids and paraffinic hydrocarbons from the carbonylation zone;
- (c) passing said product stream into a fractional distillation zone in which the product stream is separated into at least a hydrocarbon recycle stream comprising paraffinic hydrocarbons and an acid stream comprising acyclic carboxylic acids;
- (d) recycling the hydrocarbon recycle stream to the dehydrogenation zone;
- and,
- (e) recovering acyclic carboxylic acids from the acid stream.
A carbonylation process which comprises passing water, carbon monoxide and a C8-plus aliphatic substrate chosen from the group consisting of olefins, alcohols and esters into a carbonylation reaction zone maintained at carbonylation conditions and into contact with a homogeneous carbonylation catalyst system comprising a palladium imidazole complex, an aliphatic organic acid and a solvent to produce the corresponding carboxylic acids, and recovering said carboxylic acids from the carbonylation reaction zone.
A carbonylation process which comprises passing water, carbon monoxide and a C8-plus aliphatic substrate chosen from the group consisting of olefins, alcohols and esters into a carbonylation reaction zone maintained at carbonylation conditions and into contact with a homogeneous carbonylation catalyst system comprising either a palladium imidazole complex or palladium triphenyl phosphine complex, an aliphatic organic acid, lithium iodide, and a solvent to produce the corresponding carboxylic acids, and recovering said carboxylic acids from the carbonylation reaction zone.
A carbonylation process which comprises desulfurizing a C8-plus aliphatic substrate chosen from the group consisting of olefins, alcohols and esters to a sulfur content below 2 ppm;
- passing water, carbon monoxide and the C8-plus aliphatic substrate into a carbonylation reaction zone maintained at carbonylation conditions and into contact with a homogeneous carbonylation catalyst system comprising either a palladium imidazole complex or palladium triphenyl phosphine complex, an aliphatic organic acid, and a solvent to produce the corresponding carboxylic acids, and recovering said carboxylic acids from the carbonylation reaction zone.
A carbonylation process which comprises passing water, carbon monoxide and a C8-plus aliphatic substrate chosen from the group consisting of olefins, alcohols and esters into a carbonylation reaction zone maintained at carbonylation conditions and into contact with a homogeneous carbonylation catalyst system consisting essentially of a palladium triphenyl phosphine complex, an aliphatic organic acid and a solvent to produce the corresponding carboxylic acids, and recovering said carboxylic acids from the carbonylation reaction zone.
Dependencies are inferred from the claim text.