Hydroxysultaine- and sulfobetaine-based geminal zwitterionic liquids, method for obtaining same, and use thereof as wettability modifiers having corrosion inhibiting properties

Patent metadata

Field	Value
Publication number	US-11014875-B2
Application number	US-201515535323-A
Country	US
Kind code	B2
Filing date	Nov 27, 2015
Priority date	Dec 11, 2014
Publication date	May 25, 2021
Grant date	May 25, 2021

Abstract

The present disclosure is related to obtaining and using sulfobetaine and hydroxysultaine-based geminal zwitterionic liquids as wettability modifiers for rocks such as limestone, dolomite, sandstone, quartz or heterogeneous lithologies, under the presence of brines having high content of divalent ions as calcium, magnesium, barium and strontium, at high temperature and high pressure conditions for enhanced oil recovery processes to increase the oil production. The geminal zwitterionic liquids of the present disclosure have also the property of acting as corrosion inhibitors of ferrous metals used in pipelines and equipment for crude oil extraction, production, transport and storage operations. A further advantage shown by zwitterionic liquids derived from their molecular structure is they can be dissolved in distilled water, brine, hydrocarbon solvents, aromatics and alcohols.

First claim

What is claimed is:

1. A process to obtain hydroxysultaine- and sulfobetaine-based geminal zwitterionic liquids, wherein the process is carried out to the following synthesis scheme:

and wherein the synthesis comprises the following steps:
the first step comprises reacting polyethylene glycols of the formula I with benzenesulfonyl chloride or tosyl chloride of the formula II, wherein the reaction is carried out in a reaction time from 1 hour to 12 hours, resulting in a compound of formula III;
the second step comprises reacting the compound of the formula III through a nucleophilic substitution with primary or secondary amines of the formula IV, resulting in amino alcohols of formula V; and
the third step comprises obtaining sulfobetaine and hydroxysultaine-based geminal zwitterionic liquids of the formula VII by reacting the amino alcohols of the formula V with sodium 2-bromoethane sulfonate or sodium 3-chloro-2-hydroxypropane sulfonate of the formula VI; and
wherein in all of the formulae above, R 1 is a radical represented by an alkyl or alkenyl, linear or branched chain having 1 to 30 carbon atoms, or a cycloalkyl or aryl group having from 5 to 12 carbon atoms; R 2 is a radical represented by —H; an alkyl or alkenyl, linear or branched chain having from 1 to 30 carbon atoms; or a cycloalkyl or aryl group, having from 5 to 12 carbon atoms; y is 0 or 1; and n is a value from 1 to 500 depending on the molecular weight of the polyether used to prepare the sulfobetaine or hydroxysultaine, wherein the polyether is derived from ethylene oxide and has a molecular weight in the range of 100 to 20,000 g/mol.

2. The process according to claim 1 , wherein the step 1 reaction of the synthesis is carried out with a molar ratio of formula I to formula II of 1:1 to 1:4.

3. The process according to claim 2 , wherein the step 1 reaction of the synthesis is carried out in a basic medium comprising sodium, potassium or cesium hydroxide.

4. The process according to claim 2 , wherein the step 1 reaction of the synthesis further comprises a solvent selected from the group consisting of water, tetrahydrofuran, chloroform, acetonitrile, and mixtures thereof.

5. The process according to claim 1 , wherein the step 1 reaction of the synthesis is carried out at a temperature from 0° C. to 25° C.

6. The process according to claim 1 , wherein the step 2 reaction of the synthesis is carried out with a molar ratio between the compounds of the formula III and the secondary amines of the formula IV from 1:1.5 to 1:4.

7. The process according to claim 1 , wherein the step 2 reaction of the synthesis for the preparation of the amino alcohols of the formula V is carried out in presence of a solvent, wherein the solvent is selected from acetonitrile, chloroform, dimethylformamide, dimethylsulfoxide, acetone, or short chain alcohols.

8. The process according to claim 1 , wherein the step 2 reaction of the synthesis for preparation of amino alcohols of the formula V is carried out in a reaction time from 5 hours to 60 hours.

9. The process according to claim 1 , wherein the step 2 reaction of the synthesis for preparation of amino alcohols of the formula V is carried out at a temperature from 50° C. to 150° C.

10. The process according to claim 1 , wherein the step 3 reaction of the synthesis between the amino alcohols of the formula V with sodium 2-bromoethane sulfonate or sodium 3-chloro-2-hydroxypropane sulfonate of the formula VI is carried out with a molar ratio of formula V to formula VI of 1:1.5 to 1:4.

11. The process according to claim 1 , wherein the step 3 reaction of the synthesis for preparation of compounds of the formula VII can be carried out in the absence or presence of a solvent, wherein the solvent is selected from water, alcohols, aromatics, or inert hydrocarbon solvents.

12. The process according to claim 1 , wherein the reaction time of the step 3 reaction of the synthesis ranges from 6 hours to 72 hours.

13. The process according to claim 1 , wherein the temperature of the step 3 reaction of the synthesis ranges from 40° C. to 180° C.

14. The process according to claim 1 , wherein the pressure of the step 3 reaction of the synthesis ranges from 585 mmHg to 760 mmHg.

Assignees

• Mexicano Inst Petrol

Inventors

• Hernandez Altamirano Raül
• Mena Cervantes Violeta Yasmin
• Zamudio Rivera Luis Silvestre
• Flores Sandoval César Andrés
• Ramírez Estrada Alejandro
• Cisneros Devora Rodolfo
• Martínez Magadan José Manuel
• Oviedo Roa Raúl
• Ramírez Pérez Jorge Francisco

Classifications

• C07C309/18 Primary

  containing amino groups bound to the same carbon skeleton · CPC title

• C07C309/69

  of a carbon skeleton substituted by nitrogen atoms, not being part of nitro or nitroso groups · CPC title

• C09K8/54

  Compositions for in situ inhibition of corrosion in boreholes or wells · CPC title

• C07C303/22

  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 title

• C09K8/584

  characterised by the use of specific surfactants · CPC title