Alkylaromatic Sulfonate Compositions From Mixed Hydrocarbons

• US 20180057451A1
• Filed: 08/09/2017
• Published: 03/01/2018
• Est. Priority Date: 09/01/2016
• Status: Active Grant

• Current Assignee: ExxonMobil Chemical Patents Inc. (Exxon Mobil Corporation)
• Original Assignee: ExxonMobil Chemical Patents Inc. (Exxon Mobil Corporation)
• Inventors: Owens, Tracie L., Reiner, Virginia M., Zhao, Mosha H., Zhang, Jingwen, Gooding, Beatrice M., Bielenberg, James R.
• Granted Patent: US 10,435,359 B2
• Time in Patent Office: Days
• CPC Class Codes: C07C 15/107 having saturated side-chain containing at least six carbon atoms, e.g. detergent alkylates
• CPC Class Codes: C07C 2602/28 Hydrogenated naphthalenes
• CPC Class Codes: C07C 303/06 by reaction with sulfuric acid or sulfur trioxide
• CPC Class Codes: C07C 303/22 from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
• CPC Class Codes: C07C 303/32 of salts of sulfonic acids
• CPC Class Codes: C07C 303/44 Separation; Purification
• CPC Class Codes: C07C 309/31 by alkyl groups containing at least three carbon atoms
• CPC Class Codes: C07C 309/34 formed by two rings
• CPC Class Codes: C07C 7/005 Processes comprising at least two steps in series
• CPC Class Codes: C07C 7/04 by distillation
• CPC Class Codes: C07C 7/10 by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
• CPC Class Codes: C09K 8/584 characterised by the use of specific surfactants
• CPC Class Codes: E21B 43/16 Enhanced recovery methods for obtaining hydrocarbons
• CPC Class Codes: G01N 13/02 Investigating surface tension of liquids
• CPC Class Codes: G01N 2013/0275 involving surface-active agents
• CPC Class Codes: G01N 2013/0283 methods of calculating surface tension

Abstract

Provided herein are various methods for forming alkylaromatic sulfonate compositions and blended alkylaromatic sulfonate compositions, and such compositions themselves. The methods of various embodiments include obtaining a C₈-C₃₀ hydrocarbon mixture, optionally treating the mixture to concentrate the mixture in sulfonatable aromatics, and sulfonating the mixture to form the alkylaromatic sulfonates. The mixture or treated mixture may be blended with linear alkyl benzene (LAB) compositions and sulfonated, and/or the alkylaryl sulfonates may be blended with linear alkylbenzene sulfonate (LAS) compositions, to form the blended alkylaromatic sulfonates of some embodiments. These compositions and processes for making them may be tailored to serve a variety of end uses, such as detergents in cleaning solutions or for enhanced oil recovery operations, and/or as low foaming and/or hydrotropic additives in detergent formulations, and the like.

Claims

1. A process comprising:

(a) obtaining a hydrocarbon mixture comprising at least 90 wt % C₇-C₃₀ hydrocarbons;

wherein the hydrocarbon mixture comprises 5-40 wt % sulfonatable aromatics comprising;

(i) mono-alkyl benzenes;

(ii) multi-alkyl benzenes in which any two adjacent alkyl substitutions on the benzene may be joined to form a non-aromatic ring fused to the benzene, provided that either or both of the benzene and the fused non-aromatic ring is further alkyl-substituted; and

, optionally, (iii) alkyl-substituted polycyclic aromatics;

further wherein the hydrocarbon mixture comprises 1.75-30 wt % of the mono-alkyl benzenes, 0.25-30 wt % of the multi-alkyl benzenes, and 0-20 wt % of the alkyl-substituted polycyclic aromatics, such wt % s based on the total mass of the hydrocarbon mixture;

(b) treating the hydrocarbon mixture so as to obtain a precursor alkylaromatic composition comprising 30-80 wt % sulfonatable aromatics;

wherein the treating comprises 1, 2, 3, 4, or 5 solvent extractions; and

further wherein the precursor alkylaromatic composition comprises 15-35 wt % mono-alkyl benzenes, 15-30 wt % multi-alkyl benzenes; and

0-25 wt % alkyl-substituted polycyclic aromatics, such wt % s based on the total mass of the precursor alkylaromatic composition, provided that the wt % of each of the mono-alkyl benzenes, multi-alkyl benzenes, and, if present, alkyl-substituted polycyclic aromatics in the precursor alkylaromatic composition is greater than the wt % of such alkylaromatic in the hydrocarbon mixture; and

(c) sulfonating the precursor alkylaromatic composition to obtain an alkylaromatic sulfonate composition.

2. The process of claim 1, wherein the hydrocarbon mixture comprises at least 90 wt % C₁₆-C₂₆ hydrocarbons.

3. The process of claim 1, wherein the hydrocarbon mixture is a crude oil fraction comprising hydrocarbons having boiling points within the range from 140°

C. to 420°

C.

4. The process of claim 1, wherein the multi-alkyl benzenes are each selected from the group consisting of (i) benzene having two or more alkyl substitutions and (ii) alkyl-substituted tetralins;

and further wherein the alkyl-substituted polycyclic aromatics are each selected from the group consisting of alkyl substituted naphthalenes.

5. The process of claim 1, wherein the wt % of the multi-alkyl benzenes in the precursor alkylaromatic composition (1) differs from the wt % of the mono-alkyl benzenes in the precursor alkylaromatic composition by no more than 10 wt %, and (2) differs from the wt % of the alkyl-substituted polycyclic aromatics in the precursor alkylaromatic composition by no more than 10 wt %, such wt % s based on the total mass of the precursor alkylaromatic composition.

6. The process of claim 1, wherein the precursor alkylaromatic composition comprises branched mono- and multi-alkylated aromatics, and further comprises alkylated tetralins.

7. The process of claim 1, wherein at least one of the solvent extractions is carried out using N-methyl-2-pyrrolidone (NMP).

8. The process of claim 1, wherein the treating (b) further comprises one or both of hydrotreatment and reforming.

9. The process of claim 1, wherein the sulfonating (c) includes separating a light oil phase from a sulfonation reaction product and extracting the sulfonation reaction product with a sulfonation product solvent so as to obtain the alkylaromatic sulfonate.

10. The process of claim 9, wherein the sulfonation product solvent is isopropyl alcohol.

11. The process of claim 1, wherein the alkylaromatic sulfonate composition has surfactant activity within the range from 65% to 98%.

12. The process of claim 1, wherein the alkylaromatic sulfonate composition exhibits one or more of the following properties:

(i) Critical micelle concentration (CMC) within the range from 0.01-0.05 wt %;

(ii) Draves wetting within the range from 100-600 sec;

(iii) Ross-Miles Foam Height (initial) within the range from 10-40 mm;

(iv) Ross-Miles Foam Height (5 min) within the range from 10-25 mm;

(v) Interfacial Tension (IFT) of a 0.10 wt % solution of the alkylaromatic sulfonate in distilled water within the range from 5.5-9.5 mN/m; and

(vi) Calcium tolerance within the range from 50-90 mCa/g of the alkylaromatic sulfonate composition.

13. The process of claim 12, wherein the alkylaromatic sulfonate composition has Calcium tolerance within the range from 65-90 mg Ca/g of the alkylaromatic sulfonate composition.

14. An alkylaromatic sulfonate composition obtained by the process of claim 1.

15. The alkylaromatic sulfonate composition of claim 14, wherein the alkylaromatic sulfonate composition exhibits one or more of the following properties:

(i) Critical micelle concentration (CMC) within the range from 0.01-0.05 wt %;

(ii) Draves wetting within the range from 100-600 sec;

(iii) Ross-Miles Foam Height (initial) within the range from 10-40 mm;

(iv) Ross-Miles Foam Height (5 min) within the range from 10-25 mm;

(v) Interfacial Tension (IFT) of a 0.10 wt % solution of the alkylaromatic sulfonate in distilled water within the range from 5.5-9.5 mN/m; and

(vi) Calcium tolerance within the range from 50-90 mg Ca/g of the alkylaromatic sulfonate composition.

16. The alkylaromatic sulfonate composition of claim 15, having Calcium tolerance within the range from 65-90 mg Ca/g of the alkylaromatic sulfonate composition.