AMINE ADDUCTS, DERIVATIVES THEREOF, METHODS FOR MAKING SUCH ADDUCTS AND DERIVATIVES, AND METHODS FOR USING SUCH ADDUCTS AND DERIVATIVES

• US 20130161014A1
• Filed: 12/21/2012
• Published: 06/27/2013
• Est. Priority Date: 12/21/2011
• Status: Active Grant

• Current Assignee: Energysolutions LLC (Rockwell Holdco, Inc.)
• Original Assignee: Rhodia Operations (Solvac SA)
• Inventors: Pakenham, Derek, Degre, Guillaume, Morvan, Mikal
• Granted Patent: US 10,259,987 B2
• Time in Patent Office: Days
• US Class Current: 166/308.1
• CPC Class Codes: C07C 227/02 Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
• CPC Class Codes: C07C 231/14 by formation of carboxamide groups together with reactions not involving the carboxamide groups
• CPC Class Codes: C07C 233/38 having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
• CPC Class Codes: C07C 233/39 having the carbon atom of the carboxamide group bound to an acyclic carbon atom of an unsaturated carbon skeleton containing rings other than six-membered aromatic rings
• CPC Class Codes: C07C 303/20 by addition of sulfurous acid or salts thereof to compounds having carbon-to-carbon multiple bonds
• CPC Class Codes: C07C 309/14 containing amino groups bound to the carbon skeleton
• CPC Class Codes: C09K 8/584 characterised by the use of specific surfactants
• CPC Class Codes: C11D 1/62 Quaternary ammonium compounds
• CPC Class Codes: C11D 1/90 Betaines
• CPC Class Codes: C11D 1/92 Sulfobetaines ; Sulfitobetaines
• CPC Class Codes: C11D 1/94 Mixtures with anionic, cationic or non-ionic compounds
• CPC Class Codes: E21B 43/16 Enhanced recovery methods for obtaining hydrocarbons
• CPC Class Codes: E21B 43/26 by forming crevices or fractures
• CPC Class Codes: Y10T 137/0318 Processes

Abstract

An amine adduct is made by (1) forming an addition intermediate by heating a mixture comprising at least one diene and at least one unsaturated fatty acyl compound, and reacting the addition intermediate with a diamine to form the amine adduct, or by (2) reacting at least one unsaturated fatty acyl compound with at least one diamine to form an amine intermediate, and heating a mixture of the amidoamine intermediate and at least one diene to form the amine adduct, or by (3) reacting at least one unsaturated fatty tertiary amine compound with at least at least one diene to form the amine adduct. A surfactant composition is derived from the amine adduct and is particularly useful in a method for enhancing the recovery of oil from a reservoir having a production wellbore, comprising introducing an aqueous flooding fluid into the reservoir at one or more locations different from the location of the production wellbore, said fluid comprising the surfactant composition and recovering the oil through the production wellbore.

Claims

1. An amine adduct, comprising the product obtained by:

(1)(a) forming an addition intermediate by heating a mixture comprising at least one diene and at least one unsaturated fatty acyl compound, and

(b) reacting the addition intermediate with a diamine to form the amine adduct, or

(2)(a) reacting at least one unsaturated fatty acyl compound with at least one diamine to form an amidoamine intermediate, and

(b) heating a mixture of the amidoamine intermediate and at least one diene to form the amine adduct, or

(3) reacting at least one unsaturated fatty tertiary amine compound with at least at least one diene to form the amine adduct.

2. The amine adduct of claim 1 wherein the adduct is an amidoamine product, obtained by:

(1)(a) forming an addition intermediate by heating a mixture comprising at least one diene and at least one unsaturated fatty acyl compound, and

(b) reacting the addition intermediate with a diamine to form the amidoamine product, or

(2)(a) reacting at least one unsaturated fatty acyl compound with at least one diamine to form an amidoamine intermediate, and

(b) heating a mixture of the amidoamine intermediate and at least one diene to form the amidoamine product.

3. The amine adduct of claim 1, wherein the amine adduct is the amine product obtained by reacting at least one unsaturated fatty tertiary amine compound with at least at least one diene to form the amine product.

7. A surfactant composition comprising at least one surfactant compound derived from an amine adduct according to claim 1.

8. A surfactant composition, comprising at least one surfactant compound derived from the amidoamine product of claim 2.

9. A surfactant composition comprising at least one surfactant compound derived from an amine adduct according to claim 3.

10. The surfactant composition of claim 7, wherein the at least one surfactant compound is derived from the amine adduct by:

(a) treatment of the adduct with acid to form an amine salt surfactant compound,

(b) quaternization of the adduct to form a quaternary ammonium salt surfactant compound,

(c) carboxymethylation of the adduct to form a betaine surfactant compound,

(d) reaction of the adduct with a sultone or a sulfonate, to sulfobetaine surfactant compound, or

(e) oxidation of the adduct to form an amine oxide surfactant compound.

11. The surfactant composition of claim 8, wherein the at least one surfactant compound is derived from the amidoamine product by:

(a) treatment of the amidoamine product with acid to form an amine salt surfactant compound,

(b) quaternization of the amidoamine product to form a quaternary ammonium salt surfactant compound,

(c) carboxymethylation of the amidoamine product to form a betaine surfactant compound,

(d) reaction of the amidoamine product with a sultone or a sulfonate, to sulfobetaine surfactant compound, or

(e) oxidation of the amidoamine product to form an amine oxide surfactant compound.

12. The surfactant composition of claim 9, wherein the at least one surfactant compound is derived from the amine adduct by:

(a) treatment of the adduct with acid to form an amine salt surfactant compound,

(b) quaternization of the adduct to form a quaternary ammonium salt surfactant compound,

(c) carboxymethylation of the adduct to form a betaine surfactant compound,

(d) reaction of the adduct with a sultone or a sulfonate, to sulfobetaine surfactant compound, or

(e) oxidation of the adduct to form an amine oxide surfactant compound.

16. A method for handling particles, comprising dispersing the particles in an aqueous fluid comprising one or more surfactants according to claim 7 to form an aqueous particle dispersion and transporting the aqueous particle dispersion by pumping the aqueous particle dispersion through a conduit.

17. A process for fracturing a subterranean formation, comprising pumping an fluid comprising a surfactant composition according to claim 7 through a wellbore into a subterranean formation at a pressure sufficient to fracture the subterranean formation.

18. A method for enhancing the recovery of oil from a reservoir having a production wellbore, comprising:

(a) introducing an aqueous flooding fluid into the reservoir at one or more locations different from the location of the production wellbore, said fluid comprising a surfactant composition according to claim 7, and

(b) recovering the oil through the production wellbore.

19. A method for enhancing the recovery of oil from a reservoir having a production wellbore, comprising:

(a) introducing an aqueous flooding fluid into the reservoir at one or more locations different from the location of the production wellbore, said fluid comprising a surfactant composition according to claim 8, and

(b) recovering the oil through the production wellbore.

20. The method of claim 19, wherein the surfactant composition comprises a betaine compound, a sulfobetaine compound or a mixture thereof.

21. The method of claim 19, wherein the aqueous flooding fluid further comprises a gas.

22. The method of claim 19, wherein the aqueous flooding fluid is in the form of a supercritical carbon dioxide emulsion.

4. A process for making an amine adduct, comprising:

(1)(a) forming an addition intermediate by heating a mixture of at least one diene and at least one unsaturated fatty acyl compound, and

(b) reacting the addition intermediate with at least one diamine to form the amine adduct, or

(2)(a) reacting at least one unsaturated fatty acyl compound with at least one diamine to form an amine intermediate, and

(b) heating a mixture of the amidoamine intermediate and at least one diene to form the amine adduct, or

(3) reacting at least one unsaturated fatty tertiary amine compound with at least at least one diene to form the amine adduct.

5. The process of claim 4, wherein the process is for making an amidoamine product, comprising:

(1)(a) forming an addition intermediate by heating a mixture of at least one diene and at least one unsaturated fatty acyl compound, and

(b) reacting the addition intermediate with at least one diamine to form the amidoamine product, or

(2)(a) reacting at least one unsaturated fatty acyl compound with at least one diamine to form an amidoamine intermediate, and

(b) heating a mixture of the amidoamine intermediate and at least one diene to form the amidoamine product.

6. The process of claim 4, wherein the process is process is for making an amine product and comprises reacting at least one unsaturated fatty tertiary amine compound with at least at least one diene to form the amine product.

13. A surfactant composition, comprising at least one surfactant compound according to structure (I):

14. The surfactant composition of claim 13, comprising at least one surfactant compound according to structure (II):

15. A surfactant composition according to claim 13, comprising at least one surfactant compound according to structure (III):