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Methods and compositions for removing sulfur from liquid hydrocarbons using ammonium adducts

a technology of ammonium adducts and liquid hydrocarbons, which is applied in the petroleum industry, hydrocarbon oil refining, acid salt refining, etc., can solve the problems of significant reduction of the fuel value of the desulfurized end product, high cost and inherent chemical limitations, and the difficulty of hds removal, etc., to achieve convenient dispersibility and facilitate handling

Inactive Publication Date: 2007-04-12
JACAM CHEM COMPANY 2013
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0013] The adducts of the invention can be used in either solid (e.g., pellets, balls, sticks, or powders) or liquid dispersion form. In the case of solids, the adduct(s) can be mixed using a high intensity mixing device, followed by forming discrete, solid bodies. If desired, a minor amount of an anti-caking agent may be added to facilitate handling, e.g., up to about 5% (and usually no more than about 1%) by weight of an agent such a

Problems solved by technology

Upon combustion, the sulfur in fuels can contribute to air pollution in the form of particulate material and acidic gases, such as sulfur dioxide.
However, middle-distillate fractions, e.g., the diesel and fuel oil range, contain significant amounts of benzothiophenes and dibenzothiophenes (DBTs), which are considerably more difficult to remove by HDS.
Due to their resistance to HDS, sterically hindered compounds represent a significant barrier to reaching very low sulfur levels in middle- and heavy-distillate-range fuels.
The high cost and inherent chemical limitations associated with HDS make alternatives to this technology of interest to the petroleum industry.
The use of hydrocarbon degradation pathways that attached DBT were unsuccessful because these systems relied on the oxidation and mineralization of the carbon skeleton instead of on sulfur removal and therefore significantly reduced the fuel value of the desulfurized end product.

Method used

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  • Methods and compositions for removing sulfur from liquid hydrocarbons using ammonium adducts

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0022] In this example, a preferred amine adduct was prepared and used to desulfurize Saudi crude oil having a sulfur content of 3.16%.

[0023] The amine adduct was prepared by mixing together 20% by weight of solid benzoic acid and 80% by weight of liquid coco-1,3-diaminopropane, followed by moderate mixing. The reaction was slightly exothermic. Next, 2.5 gms. of the resultant adduct product were added to 30 ml. of water, and this aqueous dispersion was added to 120 ml. of Saudi crude oil. The oil / aqueous adduct mixture was then placed in a separatory funnel which was shaken vigorously approximately 100 times. The hydrocarbon and aqueous phases were then allowed to separate, and the hydrocarbon fraction was drawn off and analyzed to determine total sulfur content. The treated hydrocarbon fraction exhibited a sulfur content of 2.32%, constituting a 26.5% sulfur reduction.

example 2

[0024] The desulfurization test of Example 1 was repeated using 6 additional amine adduct products. Specifically, each amine adduct was prepared by reacting coco-1,3-diaminopropane with glacial acetic acid (Sample A), propionic acid (Sample B), boric acid (Sample C), hydroacetic acid (Sample D), adipic acid (Sample E), and succinic acid (Sample F). The respective samples were dispersed in 30 ml. water, and the resulting dispersions were added to 120 ml. of Alaskan crude oil. The above-described separatory funnel treatment was then carried out on each oil sample.

[0025] The results of this series of tests are set forth in FIG. 1. As illustrated, the untreated oil had a sulfur content of 0.905% and the treatment according to the invention resulted in a reduction in sulfur content of from about 49.2 to 66.4%.

example 3

[0026] In this example, Alaskan crude oil having a sulfur content of 0.894% was mixed with distilled water at varying percentages, and the resulting mixtures were each treated with 25 gms. of the amine-benzoic acid composition of Example 1 in 100 ml. of water. The test protocol of Example 1 was then carried out on each sample, giving the following results:

OilAliquotMixingSulfur Content% Sulfur(ml)Water (ml)(ml)Temp (° F.)(wt. %)Reduction1200101200.3406212010101200.23573.712020101200.52541.312030101200.25271.812050101200.23274.0

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Abstract

Improved desulfurization compositions are provided for removing substantial fractions of sulfur, sulfur complexes, and sulfur compounds from liquid hydrocarbons such as crude oil and fuels. The preferred compositions comprise amine adducts, such as the adduct formed by reacting benzoic acid and a fatty acid amine. The compositions may be contacted with liquid hydrocarbons in the presence of water to achieve high levels of desulfurization. Preferably, the compositions are added substantially continuously to a flowing stream of liquid hydrocarbon and water, e.g., to the output from a producing oil well or in pipeline transmission and / or refinery equipment.

Description

BACKGROUND OF THE INVENTION [0001] 1. Field of the Invention [0002] The present invention is broadly concerned with desulfurization of liquid hydrocarbon / water mixtures such as crude oils and derivatives thereof. More particularly, the invention is concerned with compositions which can be directly contacted with liquid hydrocarbons and water to effect substantial desulfurization of the hydrocarbon fractions thereof, as well as methods of preparing and using the compositions. The compositions of the invention preferably are made up of solid or liquid materials including therein an amine adduct such as the adduct derived from the reaction of coco-1,3-diaminopropane and an acid such as benzoic acid. [0003] 2. Description of the Prior Art [0004] The concentration of sulfur in crude oil is typically between 0.05 and 5.0% (by weight), although values as high as 13.95% have been reported. In general, the distribution of sulfur in crude oil is such that the proportion of sulfur increases al...

Claims

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Application Information

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IPC IPC(8): C10G45/00C10G17/00
CPCC10G17/09
Inventor ZAID, GENE H.WOLF, BETH ANNZORN, GARY W.
Owner JACAM CHEM COMPANY 2013