Amine adducts, derivatives thereof, methods for making such adducts and derivatives, and methods for using such adducts and derivatives

• US 10,259,987 B2
• Filed: 12/21/2012
• Issued: 04/16/2019
• 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, Morvan, Mikal, Degre, Guillaume
• Primary Examiner(s): Li, Aiqun
• Application Number:
  US13/724,537
• Publication Number:
  US 20130161014A1
• Time in Patent Office: 2,307 Days
• Field of Search: 507255, 507259
• 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. A dimethyl 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 3-(dimethylamino)-1-propylamine to form the dimethyl amine adduct, or

(2)(a) reacting at least one unsaturated fatty acyl compound with at least one 3-(dimethylamino)-1-propylamine to form an amidoamine intermediate, and

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

wherein the diene is a (C₄-C₃₀) conjugated diene selected from the group consisting of isoprene, butadiene, dimethylbutadiene, and dicyclopentadiene.

2. A surfactant composition comprising at least one diene-modified dimethyl surfactant compound comprising a cycloadduct and derived from a dimethyl amine adduct according to claim 1, wherein the at least one diene-modified dimethyl 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.

3. A method for handling particles, comprising dispersing the particles in an aqueous fluid comprising one or more surfactants according to claim 2 to form an aqueous particle dispersion and transporting the aqueous particle dispersion by pumping the aqueous particle dispersion through a conduit.

4. A process for fracturing a subterranean formation, comprising pumping an fluid comprising a surfactant composition according to claim 2 through a wellbore into a subterranean formation at a pressure sufficient to fracture the subterranean formation.

5. 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 2, and

(b) recovering the oil through the production wellbore.