IP Library Granted Patent US 7,311,815
Granted Patent B2
US 7,311,815 · App. 10/427,508 · Granted Dec 25, 2007

Hydrocarbon products and methods of preparing hydrocarbon products

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Quick Facts
Patent No.
US 7,311,815
App. No.
10/427,508
Granted
Dec 25, 2007
Kind
B2
Abstract

A method of preparing high linear paraffin or high end-chain monomethyl content products is accomplished by converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon products. These may be hydrotreated to provide an n-paraffin content of greater than 50% by weight, with substantially all branched paraffins being monomethyl end-chain branched paraffins. At least one non-linear paraffin isomer, which may be a monomethyl paraffin isomer, may be separated from the hydrocarbon products through distillation to provide an n-paraffin product having an n-paraffin content percentage by weight of the n-paraffin product that is greater than the initial n-paraffin content.

Claims (60)

1. A method of forming a hydrocarbon product consisting of:

converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon products;

hydrotreating the hydrocarbon products to provide hydrotreated hydrocarbon products, the hydrotreated hydrocarbon products having an n-paraffin content of at least 50% by weight of the hydrotreated hydrocarbon products and branched paraffins,

wherein the ratio of end-chain monomethyl branching to internal branching of the monomethyl branched paraffins is at least about 1:1.

2. A method of forming a hydrocarbon product consisting of:

converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon products;

hydrotreating the hydrocarbon products to provide hydrotreated hydrocarbon products, the hydrotreated hydrocarbon products having an n-paraffin content of at least 50% by weight of the hydrotreated hydrocarbon products and branched paraffins,

wherein the ratio of end-chain monomethyl branching to internal branching of the monomethyl branched paraffins is at least about 2:1.

3. A method of forming a hydrocarbon product consisting of:

converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon products;

hydrotreating the hydrocarbon products to provide hydrotreated hydrocarbon products, the hydrotreated hydrocarbon products having an initial n-paraffin content of greater than about 67% by weight of the hydrotreated hydrocarbon products and having branched paraffins;

separating at least a portion of at least one non-linear branched paraffin isomer from the hydrocarbon products through distillation to provide an n-paraffin product having an n-paraffin content percentage by weight of the n-paraffin product that is greater than the initial n-paraffin content; and

isolating C 8 to C 24 hydrocarbon products from the hydrocarbon products; and wherein the initial n-paraffin content is the initial n-paraffin content of the C 8 to C 24 hydrocarbon products.

4. The method of claim 3 , wherein the C 8 to C 24 hydrocarbon products are C 10 to C 14 hydrocarbon products.

5. A method of forming a hydrocarbon product consisting of:

converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon products;

hydrotreating the hydrocarbon products to provide hydrotreated hydrocarbon products, the hydrotreated hydrocarbon products having an initial n-paraffin content of greater than about 67% by weight of the hydrotreated hydrocarbon products and having branched paraffins; and

separating at least a portion of at least one non-linear branched paraffin isomer from the hydrocarbon products through distillation to provide an n-paraffin product having an n-paraffin content percentage by weight of the n-paraffin product that is greater than the initial n-paraffin content,

wherein the hydrotreated hydrocarbon products have an initial monomethyl branched paraffin content of greater than about 2% by weight of the hydrotreated hydrocarbon products without employing non-distillation separation techniques,

wherein separating at least a portion of at least one non-linear branched paraffin isomer includes separating at least one monomethyl branched paraffin isomer from the hydrocarbon products,

wherein separating the at least one monomethyl branched paraffin isomer includes separating a monomethyl fraction containing the at least one monomethyl branched paraffin isomer, and

wherein the monomethyl fraction contains the at least one monomethyl branched paraffin isomer in an amount of at least 20% by weight of the monomethyl fraction.

6. A method of forming a hydrocarbon product consisting of:

converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon products;

hydrotreating the hydrocarbon products to provide hydrotreated hydrocarbon products, the hydrotreated hydrocarbon products having an initial n-paraffin content of greater than about 67% by weight of the hydrotreated hydrocarbon products and having branched paraffins; and

separating at least a portion of at least one non-linear branched paraffin isomer from the hydrocarbon products through distillation to provide an n-paraffin product having an n-paraffin content percentage by weight of the n-paraffin product that is greater than the initial n-paraffin content,

wherein the hydrotreated hydrocarbon products have an initial inonomethyl branched paraffin content of greater than about 2% by weight of the hydrotreated hydrocarbon products without employing non-distillation separation techniques,

wherein separating at least a portion of at least one non-linear branched paraffin isomer includes separating at least one monomethyl branched paraffin isomer from the hydrocarbon products, and

wherein at least 50% by weight of the monomethyl branched paraffins are end-chain monomethyl branched paraffins.

7. A method of forming a hydrocarbon product consisting of:

converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon products;

hydrotreating the hydrocarbon products to provide hydrotreated hydrocarbon products, the hydrotreated hydrocarbon products having an initial n-paraffin content of greater than about 67% by weight of the hydrotreated hydrocarbon products and having branched paraffins; and

separating at least a portion of at least one non-linear branched paraffin isomer from the hydrocarbon products through distillation to provide an n-paraffin product having an n-paraffin content percentage by weight of the n-paraffin product that is greater than the initial n-paraffin content,

wherein the hydrotreated hydrocarbon products have an initial monomethyl branched paraffin content of greater than about 2% by weight of the hydrotreated hydrocarbon products without employing non-distillation separation techniques,

wherein separating at least a portion of at least one non-linear branched paraffin isomer includes separating at least one monomethyl branched paraffin isomer from the hydrocarbon products,

wherein at least 67% by weight of the monomethyl branched paraffins are end-chain monomethyl branched paraffins.

8. A method of forming hydrocarbon products consisting of:

converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon F-T reaction products;

hydrotreating the hydrocarbon F-T reaction products to form hydrocarbon products;

isolating C 8 to C 24 hydrocarbons from the hydrocarbon products, the C 8 to C 24 hydrocarbons having an initial n-paraffin content greater than about 92% by weight of the hydrotreated hydrocarbon products and having an initial monomethyl branched paraffin content of greater than about 2% by weight of the C 8 to C 24 hydrocarbon products; and

separating at least a portion of at least one monomethyl branched paraffin isomer from the C 8 to C 24 hydrocarbon products through distillation to provide an n-paraffin product having an n-paraffin content percentage by weight of the n-paraffin product that is greater than the initial n-paraffin content,

wherein separating the at least one monomethyl branched paraffin isomer includes separating a monomethyl fraction containing the at least one monomethyl branched paraffin isomer, and

wherein the monomethyl fraction contains the at least one monomethyl branched paraffin isomer in an amount of at least 20% by weight of the monomethyl fraction.

9. A method of forming hydrocarbon products consisting of:

converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon F-T reaction products;

hydrotreating the hydrocarbon F-T reaction products to form hydrocarbon products:

isolating C 8 to C 24 hydrocarbons from the hydrocarbon products, the C 8 to C 24 hydrocarbons having an initial n-paraffin content greater than about 92% by weight of the hydrotreated hydrocarbon products and having an initial monomethyl branched paraffin content of greater than about 2% by weight of the C 8 to C 24 hydrocarbon products; and

separating at least a portion of at least one monomethyl branched paraffin isomer from the C 8 to C 24 hydrocarbon products through distillation to provide an n-paraffin product having an n-paraffin content percentage by weight of the n-paraffin product that is greater than the initial n-paraffin content,

wherein at least 40% by weight of the monomethyl branched paraffins are end-chain monomethyl branched paraffins.

10. A method of forming hydrocarbon products consisting of: converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon F-T reaction products;

hydrotreating the hydrocarbon F-T reaction products to form hydrocarbon products:

isolating C 8 to C 24 hydrocarbons from the hydrocarbon products, the C 8 to C 8 to C 24 hydrocarbons having an initial n-paraffin content greater than about 92% by weight of the hydrotreated hydrocarbon products and having an initial monomethyl branched paraffin content of greater than about 2% by weight of the C 8 to C 24 hydrocarbon products; and

separating at least a portion of at least one monomethyl branched paraffin isomer from the C 8 to C 24 hydrocarbon products through distillation to provide an n-paraffin product having an n-paraffin content percentage by weight of the n-paraffin product that is greater than the initial n-paraffin content,

wherein at least 67% by weight of the monomethyl branched paraffins are end-chain monomethyl branched paraffins.

11. A method of forming a hydrocarbon product consisting of:

converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon products; and

hydrotreating at least a portion of the hydrocarbon products to provide hydrotreated hydrocarbon products; and

removing oxygenates from the hydrotreated hydrocarbon products by passing the hydrotreated hydrocarbon products over at least one of an alumina, silica or alumina-silica molecular sieve adsorbent so that the hydrotreated hydrocarbon products contain less than 20 ppm by weight of oxygenates,

wherein the hydrotreated hydrocarbon products contain from 50 to 500 ppm by weight oxygenates prior to the removal of oxygenates, and

wherein the hydrotreated hydrocarbon products include at least one of chemical naphtha for ethylene cracking in the C 8 to C 8 range, fuel cell feedstocks in the C 4 -C 8 range, normal paraffin compounds in the C 5 -C 30 range, isoparaffin compounds in the C 5 -C 30 range, normal paraffin and isoparaffin drilling fluids in the C 8 -C 25 range, lubricating fluids in the C 5 -C 30 range, drilling fluids in the C 5 -C 30 range, food grade solvents in the C 5 -C 60 range, base oils in the C 5 -C 60 range, solvents in the C 5 -C 60 range, oils in the C 5 -C 60 range, and functional fluids in the C 5 -C 60 range.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 29, 2014
From: SYNTROLEUM CORPORATION
To: REG SYNTHETIC FUELS, LLC
Reel/Frame 033430/0470 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 30, 2003
From: ABAZAJIAN, ARMEN N.
To: SYNTROLEUM CORPORATION
Reel/Frame 014039/0743 →