US 12,421,186 B2
Organic ammonium salts with traceability and detergent dispersant properties to liquid fuels and processes for their synthesis
Ricardo Cerón Camacho, Mexico City (MX); Raúl Oviedo Roa, Mexico City (MX); Jorge Francisco Ramírez Pérez, Mexico City (MX); Enrique Soto Castruita, Mexico City (MX); Rodolfo Cisneros Dévora, Mexico City (MX); David Aaron Nieto Álvarez, Mexico City (MX); José Manuel Martinez Magadan, Mexico City (MX); Ana Graciela Servín Nájera, Mexico City (MX); and Luis Silvestre Zamudio Rivera, Mexico City (MX)
Assigned to Instituto Mexicano del Petróleo, Mexico City (MX)
Filed by Instituto Mexicano del Petróleo, Mexico City (MX)
Filed on Jun. 5, 2023, as Appl. No. 18/205,604.
Claims priority of application No. MX/a/2022/015075 (MX), filed on Nov. 29, 2022.
Prior Publication US 2024/0190812 A1, Jun. 13, 2024
Int. Cl. C07C 245/08 (2006.01); C07C 211/63 (2006.01); C07C 215/40 (2006.01); C07D 207/40 (2006.01); C09B 29/01 (2006.01); C09B 67/18 (2006.01); C10L 1/222 (2006.01); C10L 1/226 (2006.01); C10L 1/232 (2006.01); C10L 1/233 (2006.01); C10L 10/06 (2006.01); G01N 30/02 (2006.01); G01N 30/74 (2006.01); G01N 30/86 (2006.01); G01N 33/28 (2006.01)
CPC C07C 245/08 (2013.01) [C07C 211/63 (2013.01); C07C 215/40 (2013.01); C07D 207/40 (2013.01); C09B 29/0007 (2013.01); C09B 67/002 (2013.01); C10L 1/2222 (2013.01); C10L 1/226 (2013.01); C10L 1/232 (2013.01); C10L 1/2335 (2013.01); C10L 10/06 (2013.01); G01N 30/74 (2013.01); G01N 30/8624 (2013.01); G01N 33/2835 (2013.01); C10L 2200/0423 (2013.01); C10L 2270/023 (2013.01); G01N 2030/027 (2013.01)] 10 Claims
OG exemplary drawing
 
1. A supramolecular surfactant of structural formula (14):

OG Complex Work Unit Chemistry
wherein the surfactant comprises an AZO:A organic ammonium salt of structural formula (13):

OG Complex Work Unit Chemistry
wherein:
Ar: aromatic, such as an aryl, naphthol, naphthylamide, dimethylaniline, indole, pyrrole, pyrazolone, or substituted quinolones;
R1: is a linear or branched alkyl or alkenyl chain ranging from C1 to C30 or a cycloalkyl or aryl group from C5 to C12 or aromatics, benzyls, naphthols, naphthylamines, or dimethyl anilines substituted with electron donors selected from NH2, OH, alkyl, and/or electro-attractors selected from the group consisting of COOR (ester), CO (ketone), COOH, CN, NO2, and SO3H;
R2: is a substituent of a protic and/or acidic nature selected from the group COOH, SO3H, and OH;
R3: is H or a linear or branched alkyl or alkenyl chain from C1 to C32, or a cycloalkyl or aryl group from C5 to C12, or aromatics, benzyls, naphthols, naphthylamines, or substituted dimethyl anilines;
R4: is H, or a linear or branched alkyl or alkenyl chain from C1 to C32, or a cycloalkyl or aryl group from C5 to C12 or aromatics, benzyls, naphthols, naphthylamines or substituted dimethyl anilines; and
R5: a linear or branched alkyl or alkenyl chain from C1 to C32, or a cycloalkyl or aryl group from C5 to C12, or primary, secondary or tertiary amino alcohols, linear or branched, cyclic or aromatics and/or derived from poly-isobutenyl-succinic anhydrides, poly-isobutylene, poly-isobutenylphenols or Mannich bases,
non-covalently interacting with an organic compound OC of structural formula (6),

OG Complex Work Unit Chemistry
wherein:
R6: is hydrogen, or a linear or branched alkyl or alkenyl chain ranging from C1 to C32, or a cycloalkyl or aryl group from C5 to C12, or substituted aromatic and/or derived from poly-isobutenyl-succinic anhydrides, poly-isobutylene, poly-isobutenylphenols or Mannich bases;
R7: is a linear or branched alkyl or alkenyl chain ranging from C1 to C32, or a cycloalkyl or aryl group from C5 to C12, or substituted aromatic;
R8: is hydrogen, or a linear or branched alkyl or alkenyl chain ranging from C1 to C32, or a cycloalkyl or aryl group from C5 to C12, or substituted aromatic with —OH and —NH2 groups;
n: it has values between zero and four;
D1: nitrogen with substituents R6 and R7; and
D2: is selected from oxygen, nitrogen, or sulfur as a substituent of the R8 group.