# US 11,441,089 B2 · High napthenic content distillate fuel compositions

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- Number: US 11,441,089 B2
- Document ID: US11441089B2
- Status: Granted
- Kind: B2
- Application number: 17/325,944
- Filed: 2021-05-20
- Published: 2021-11-25
- Granted: 2022-09-13
- Earliest claimed: 2020-05-22
- Assignees: ExxonMobil Technology and Engineering Company
- Applicants: ExxonMobil Technology and Engineering Company
- Inventors: Sheryl B. Rubin-Pitel; Timothy J. Anderson; Kenneth C. H. Kar; Marcia E. Dierolf; Shifang Luo; Ian J. Laurenzi; Xinrui Yu; Yi Xu
- Web page: https://patentgrep.com/patent/US11441089B2

## CPC

- C10L 1/08: for compression ignition
- C10G 7/00: Distillation of hydrocarbon oils
- C10G 45/02: to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing
- C10G 45/44: Hydrogenation of the aromatic hydrocarbons
- C10G 65/08: at least one step being a hydrogenation of the aromatic hydrocarbons
- C10G 67/02: plural serial stages only
- C10G 2300/107: Atmospheric residues having a boiling point of at least about 538 °C
- C10G 2300/202: Heteroatoms content, i.e. S, N, O, P
- C10G 2300/301: Boiling range
- C10G 2300/307: Cetane number, cetane index
- C10G 2300/4043: Limiting CO2 emissions
- C10G 2300/405: Limiting CO, NOx or SOx emissions
- C10G 2400/04: Diesel oil
- C10L 2200/0446: Diesel
- C10L 2200/0469: Renewables or materials of biological origin
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES

## Abstract

Distillate boiling range and/or diesel boiling range compositions are provided that are formed from crude oils with unexpected combinations of high naphthenes to aromatics weight and/or volume ratio and a low sulfur content. This unexpected combination of properties is characteristic of crude oils that can be fractionated to form distillate/diesel boiling range compositions that can be used as fuels/fuel blending products with reduced or minimized processing. The resulting distillate boiling range fractions and/or diesel boiling range fractions can have an unexpected combination of a high naphthenes to aromatics weight and/or volume ratio, a low but substantial aromatics content, and a low sulfur content. By reducing, minimizing, or avoiding the amount of hydroprocessing needed to meet fuel and/or fuel blending product specifications, the fractions derived from the high naphthenes to aromatics ratio and low sulfur crudes can provide fuels and/or fuel blending products having a reduced or minimized carbon intensity.

## Claims

### Claim 1

A distillate boiling range composition comprising a T90 distillation point of 360° C. or less, a cetane index of 45 or more, a naphthenes to aromatics weight ratio of 2.5 or more, an aromatics content of 4.5 wt % to 25 wt %, a sulfur content of 1000 wppm or less, and a weight ratio of aliphatic sulfur to total sulfur of 0.15 or more, and
wherein the distillate boiling range composition has not been exposed to hydroprocessing conditions.

### Claim 2 (depends on 1)

The distillate boiling range composition of claim 1, wherein the distillate boiling range composition comprises a naphthenes to aromatics ratio of 2.6 or more, an aromatics content of 5.0 wt % to 18 wt %, and a sulfur content of 500 wppm or less.

### Claim 3 (depends on 1)

The distillate boiling range composition of claim 1, wherein the distillate boiling range composition comprises a sulfur content of 500 wppm or less, or wherein the density at 15.6° C. is 870 kg/m3 or less, or wherein the saturates content is 78 wt % or more, or wherein the distillate boiling range composition comprises a weight ratio of basic nitrogen to total nitrogen of 0.15 or more, or wherein the cetane index is 55 or more, or a combination thereof.

### Claim 4 (depends on 1)

The distillate boiling range composition of claim 1, wherein the aromatics content is 4.5 wt % to 18 wt %, or wherein the saturates content is 82 wt % or more, or wherein the sulfur content is 500 wppm or less, or wherein the density at 15.6° C. is 835 kg/m3 or less, or a combination thereof.

### Claim 5 (depends on 1)

The distillate boiling range composition of claim 1, wherein the distillate boiling range composition comprises a ratio of cetane index to weight percent of aromatics of 2.8 or higher.

### Claim 6 (depends on 1)

The distillate boiling range composition of claim 1, wherein the distillate boiling range composition is used as a fuel in an engine, a furnace, a burner, a combustion device, or a combination thereof.

### Claim 7 (depends on 1)

The distillate boiling range composition of claim 1, wherein the distillate boiling range composition comprises a carbon intensity of 88 g CO2eq/MJ of lower heating value or less.

### Claim 8

A diesel boiling range composition comprising a T90 distillation point of 375° C. or less, a naphthenes to aromatics weight ratio of 2.5 or more, an aromatics content of 4.5 wt % to 18 wt %, a cetane index of 55 or more, a density at 15° C. of 810 to 835 kg/m3, and a sulfur content of 10 wppm or less.

### Claim 9 (depends on 8)

The diesel boiling range composition of claim 8, wherein the aromatics content is 4.5 wt % to 16 wt %, or wherein the naphthenes to aromatics weight ratio is 2.9 or more, or a combination thereof.

### Claim 10 (depends on 8)

The diesel boiling range composition of claim 8, wherein the aromatics content is 4.5 wt % to 10 wt %, the naphthenes to aromatics weight ratio is 4.0 or more, and the cetane index is 57 or more.

### Claim 11 (depends on 10)

The diesel boiling range composition of claim 10, wherein the naphthenes content is 40 wt % or more.

### Claim 12 (depends on 8)

The diesel boiling range composition of claim 8, wherein the aromatics content is 4.5 wt % to 10 wt %, the naphthenes content is 20 wt % to 35 wt %, and the cetane index is 57 or more.

### Claim 13 (depends on 8)

The diesel boiling range composition of claim 8, wherein the diesel boiling range composition comprises a ratio of cetane index to weight percent of aromatics of 2.8 or higher, or wherein the diesel boiling range composition comprises a volumetric energy density of 36.1 MJ/liter or higher or a combination thereof.

### Claim 14 (depends on 1)

The diesel boiling range composition of claim 1, wherein the diesel boiling range composition is used as a fuel in an engine, a furnace, a burner, a combustion device, or a combination thereof, the diesel boiling range composition optionally comprising a carbon intensity of 90 g CO2eq/MJ of lower heating value or less.

### Claim 15 (depends on 14)

The diesel boiling range composition of claim 14, wherein the diesel boiling range composition is used in an engine of a vehicle, a tailpipe emission of at least one of NOx, CO2, CO, and hydrocarbons for the engine being reduced relative to a fuel having an aromatics content of 25 wt % or more.

### Claim 16 (depends on 14)

The diesel boiling range composition of claim 14, wherein the diesel boiling range composition is used in an engine of a vehicle, a fuel consumption for the engine being reduced relative to a fuel having an aromatics content of 25 wt % or more and being reduced relative to a fuel having an aromatics content of 3.0 wt % or less.

### Claim 17

A diesel boiling range composition comprising a T10 distillation point of 250° C. or more, a T90 distillation point of 375° C. or less, a naphthenes to aromatics weight ratio of 1.6 or more, an aromatics content of 4.5 wt % to 25 wt %, a cetane index of 55 or more, a density at 15° C. of 810 to 835 kg/m3, and a sulfur content of 10 wppm or less.

### Claim 18 (depends on 17)

The diesel boiling range composition of claim 17, wherein the aromatics content is 4.5 wt % to 10 wt %, the naphthenes to aromatics weight ratio is 4.0 or more, and the cetane index is 65 or more.

### Claim 19 (depends on 17)

The diesel boiling range composition of claim 17, wherein the aromatics content is 5.0 wt % to 25 wt %.

### Claim 20 (depends on 17)

The diesel boiling range composition of claim 17, wherein the diesel boiling range composition comprises a ratio of cetane index to weight percent of aromatics of 2.8 or higher, or wherein the diesel boiling range composition comprises a volumetric energy density of 36.1 MJ/liter or higher or a combination thereof.

### Claim 21

A method for forming a diesel boiling range composition, comprising:
fractionating a crude oil comprising a final boiling point of 550° C. or more to form at least a diesel boiling range fraction, the crude oil comprising a naphthenes to aromatics volume ratio of 1.6 or more and a sulfur content of 0.2 wt % or less, the diesel boiling range fraction comprising a T90 distillation point of 375° C. or less; and
hydrotreating the diesel boiling range fraction to form a hydrotreated diesel boiling range fraction comprising a naphthenes to aromatics weight ratio of 1.6 or more, an aromatics content of 4.5 wt % to 22 wt %, a cetane index of 55 or more, a density at 15° C. of 810 to 835 kg/m3, and a sulfur content of 10 wppm or less.

### Claim 22 (depends on 21)

The method of claim 21, wherein the diesel boiling range fraction comprises a sulfur content of 40 wppm to 500 wppm prior to the hydrotreating; or wherein the diesel boiling range fraction is hydrotreated prior to the fractionating, the fractionating comprising forming at least the hydrotreated diesel boiling range fraction; or wherein the hydrotreated diesel boiling range fraction comprises a carbon intensity of 90 g CO2eq/MJ of lower heating value or less; or a combination thereof.

### Claim 23 (depends on 21)

The method of claim 21, wherein the hydrotreated diesel boiling range fraction comprises an aromatics content of 4.5 wt % to 18 wt %, or wherein the hydrotreated diesel boiling range fraction comprises a naphthenes to aromatics weight ratio of 2.8 or more, or a combination thereof.

### Claim 24 (depends on 21)

The method of claim 21, further comprising exposing the hydrotreated diesel boiling range fraction to aromatic saturation conditions to form an aromatic saturated, hydrotreated diesel boiling range fraction comprising an aromatics content of 4.5 wt % to 10 wt %, a naphthenes to aromatics weight ratio is 4.0 or more, and a cetane index of 57 or more, the aromatic saturated, hydrotreated diesel boiling range fraction optionally comprising a naphthenes content of 40 wt % or more.

### Claim 25 (depends on 21)

The method of claim 21, wherein the hydrotreated diesel boiling range fraction comprises an aromatics content is 4.5 wt % to 10 wt %, a naphthenes to aromatics weight ratio is 2.4 or more, a naphthenes content of 20 wt % to 35 wt %, and a cetane index is 57 or more.

### Claim 26 (depends on 21)

The method of claim 21, further comprising blending at least a portion of the diesel boiling range fraction with a renewable distillate fraction.