ANIONIC-CATIONIC-NONIONIC SURFACTANT, PRODUCTION AND USE THEREOF

• US 20190330516A1
• Filed: 07/11/2019
• Published: 10/31/2019
• Est. Priority Date: 10/22/2014
• Status: Active Grant

• Current Assignee: China Petroleum & Chemical Corporation (Central People's Government of The People's Republic of China), SINOPEC Shanghai Research Institute of Petrochemical Technology
• Original Assignee: China Petroleum & Chemical Corporation (Central People's Government of The People's Republic of China), SINOPEC Shanghai Research Institute of Petrochemical Technology
• Inventors: LI, Yingcheng, GU, Songyuan, ZHANG, Weidong, BAO, Xinning, SHA, Ou, SHEN, Zhiqin, YANG, Yiqing, ZHAI, Xiaodong
• Granted Patent: US 11,186,764 B2
• Time in Patent Office: Days
• CPC Class Codes: C07C 213/06 from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
• CPC Class Codes: C07C 217/08 the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
• CPC Class Codes: C07C 231/14 by formation of carboxamide groups together with reactions not involving the carboxamide groups
• CPC Class Codes: C07C 233/05 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 233/09 with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
• CPC Class Codes: C07C 233/36 having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 237/08 having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 237/40 having the nitrogen atom of the carboxamide group bound to a carbon atom of a six-membered aromatic ring
• 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 309/10 with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
• CPC Class Codes: C09K 8/584 characterised by the use of specific surfactants
• CPC Class Codes: C09K 8/602 containing surfactants

Abstract

This invention relates to an anionic-cationic-nonionic surfactant as substantially represented by the formula (I), production and use thereof in tertiary oil recovery. The anionic-cationic-nonionic surfactant of this invention exhibits significantly improved interfacial activity and stability as compared with the prior art. With the present anionic-cationic-nonionic surfactant, a flooding fluid composition for tertiary oil recovery with improved oil displacement efficiency and oil washing capability as compared with the prior art could be produced.

In the formula (I), each group is as defined in the specification.

Claims

1. The anionic-cationic-nonionic surfactant, which is one or more selected from the group consisting of the compound as substantially represented by the formula (I-1), and the compound as substantially represented by the formula (I-2) with the proviso that, at least one N atom contained in the molecular structure thereof bonds to an additional group Rh and an additional group X so as to form into a quaternary ammonium salt/hydroxide group represented by the formula

2. The anionic-cationic-nonionic surfactant according to claim 1, wherein numerical value m′

is identical with or different from one another, each independently represents a value from 0 to 50, plural numerical value n′

may be identical with or different from one another, each independently represents a value from 0 to 50, the plural numerical value m″

is identical with or different from one another, each independently represents a value from 0 to 50, and the plural numerical value n″

is identical with or different from one another, each independently represents a value from 0 to 50.

3. The anionic-cationic-nonionic surfactant according to claim 1, wherein throughout the molecular structure of the anionic-cationic-nonionic surfactant, assuming that a total number of the group X⁻

is e1, a total number of the group N⁺ is e2, a total number of the group A⁻

is e3, a total number of the group (M)_r⁺ is e4, when e2=e3, then 0≤

e1≤

e2, 0≤

e4≤

e3;

or, when e2>

e3, then 0<

e1≤

e2, 0≤

e4≤

e3;

or, when e2≤

e3, then 0≤

e1≤

e2, 0<

e4≤

e3, with the proviso that e1+e3=e2+e4, or e2=e3, e1=0, and e4=0

7. A process for producing an anionic-cationic-nonionic surfactant according to claim 1, which is characterized by including the following steps:

Step (1);

reacting one or more multifunctional compound containing nitrogen and carrying one or more functional group selected from the group consisting of —

OH, —

NH₂ and —

NH—

with one or more alkylene oxide represented by the following formula (Y) in the presence of an alkaline catalyst, to obtain an ether product,

9. The process according to claim 7, wherein the ratio by molar of the multifunctional compound to the alkylene oxide is 1:

0-200, excluding 0;

the ratio by molar of the multifunctional compound to the compound represented by the formula (Z) is 1;

1-10;

the reaction conditions in Step (1) include a reaction temperature from the room temperature to 300 degrees Celsius, a reaction duration from 1 to 20 h;

the reaction conditions in Step (2) include a reaction temperature from 0 to 300 degrees Celsius, a reaction duration from 1 to 20 h;

the reaction conditions in Step (3) include a reaction temperature from 0 to 300 degrees Celsius, a reaction duration from 1 to 20 h.

10. The process according to claim 7, wherein the alkylene oxide comprises at least propylene oxide, and the multifunctional compound is made to firstly react with propylene oxide.

13. A flooding fluid composition for tertiary oil recovery, which is characterized by comprising an anionic-cationic-nonionic surfactant according to claim 1, and water, wherein the content of the anionic-cationic-nonionic surfactant is 0.001-10 wt %, relative to the total weight (as 100 wt %) of the flooding fluid composition for tertiary oil recovery.

14. The flooding fluid composition for tertiary oil recovery according to claim 13, comprising no inorganic alkali.

17. A tertiary oil recovery process, which is characterized by including a step of conducting tertiary oil recovery in the presence of an anionic-cationic-nonionic surfactant according to claim 1 as a flooding fluid.

18. The tertiary oil recovery process according to claim 17, wherein no inorganic alkali is used.

4. The anionic-cationic-nonionic surfactant, which is one or more selected from the group consisting of the compound as substantially represented by the formula (I-3), and the compound as substantially represented by the formula (I-4), with the proviso that, at least one N atom contained in the molecular structure thereof bonds to an additional group Rh and an additional group X so as to form into a quaternary ammonium salt/hydroxide group represented by the formula

5. The anionic-cationic-nonionic surfactant according to claim 4, wherein numerical value m′

is identical with or different from one another, each independently represents a value from 0 to 50, plural numerical value n′

may be identical with or different from one another, each independently represents a value from 0 to 50, the plural numerical value m″

is identical with or different from one another, each independently represents a value from 0 to 50, and the plural numerical value n″

is identical with or different from one another, each independently represents a value from 0 to 50.

6. The anionic-cationic-nonionic surfactant according to claim 4, wherein throughout the molecular structure of the anionic-cationic-nonionic surfactant, assuming that a total number of the group X⁻

is e1, a total number of the group N⁺ is e2, a total number of the group A⁻

is e3, a total number of the group (M)_r⁺ is e4, when e2=e3, then 0<

e1≤

e2, 0≤

e4≤

e3;

or, when e2>

e3, then 0<

e1≤

e2, 0≤

e4≤

e3;

or, when e2<

e3, then 0≤

e1≤

e2, 0<

e4≤

e3, with the proviso that e1+e3=e2+e4, or e2=e3, e1=0, and e4=0

8. A process for producing an anionic-cationic-nonionic surfactant according to claim 4, which is characterized by including the following steps:

Step (1);

reacting one or more multifunctional compound containing nitrogen and carrying one or more functional group selected from the group consisting of —

OH, —

NH₂ and —

NH—

with one or more alkylene oxide represented by the following formula (Y) in the presence of an alkaline catalyst, to obtain an ether product,

11. The process according to claim 8, wherein the ratio by molar of the multifunctional compound to the alkylene oxide is 1:

0-200, excluding 0;

the ratio by molar of the multifunctional compound to the compound represented by the formula (Z) is 1;

1-10;

the reaction conditions in Step (1) include a reaction temperature from the room temperature to 300 degrees Celsius, a reaction duration from 1 to 20 h;

the reaction conditions in Step (2) include a reaction temperature from 0 to 300 degrees Celsius, a reaction duration from 1 to 20 h;

the reaction conditions in Step (3) include a reaction temperature from 0 to 300 degrees Celsius, a reaction duration from 1 to 20 h.

12. The process according to claim 8, wherein the alkylene oxide comprises at least propylene oxide, and the multifunctional compound is made to firstly react with propylene oxide.

15. A flooding fluid composition for tertiary oil recovery, which is characterized by comprising an anionic-cationic-nonionic surfactant according to claim 6, and water, wherein the content of the anionic-cationic-nonionic surfactant is 0.001-10 wt %, relative to the total weight (as 100 wt %) of the flooding fluid composition for tertiary oil recovery.

16. The flooding fluid composition for tertiary oil recovery according to claim 15, comprising no inorganic alkali.

19. A tertiary oil recovery process, which is characterized by including a step of conducting tertiary oil recovery in the presence of an anionic-cationic-nonionic surfactant according to claim 6 as a flooding fluid.

20. The tertiary oil recovery process according to claim 19, wherein no inorganic alkali is used.