Gemini surfactants, process of manufacture and use as multifunctional corrosion inhibitors 机翻标题: 暂无翻译,请尝试点击翻译按钮。

公开号/公开日
US2013340326 A1 2013-12-26 [US20130340326]US9023785 B2 2015-05-05 [US9023785] / 2013-12-262015-05-05
申请号/申请日
2013US-13945307 / 2013-07-18
发明人
HERNANDEZ ALTAMIRANO RAUL;MENA CERVANTES VIOLETA YASMIN;ZAMUDIO RIVERA LUIS SILVESTRE;BELTRAN CONDE HIRAM ISAAC;LOPEZ RAMIREZ SIMON;
申请人
INSTITUTO MEXICANO DEL PETROLEO;
主分类号
IPC分类号
C07C-229/12C09K-005/10C10G-075/02C10L-001/12C10L-001/14C10L-001/16C10L-001/182C10L-001/222C10L-001/223C10L-001/2387C10L-010/04C11D-001/62C23F-011/173
摘要
(US9023785) Gemini surfactants of bis-N-alkyl polyether, bis-N-alkenyl polyether, bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta or alpha-amino acids or their salts, are produced for use as multifunctional corrosion inhibitors, which protect and prevent corrosion of ferrous metals exposed to acidic, basic and neutral liquids when transporting or storing crude oil and liquid fuels.  The surfactants are also used to inhibit corrosion of equipment and pipes used in cooling systems in petroleum and petrochemical equipment.  The Gemini surfactants have the structural formula:
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地址
代理人
代理机构
;
优先权号
2009MX-PA13704 2009-12-15 2010US-12967520 2010-12-14 2013US-13945307 2013-07-18
主权利要求
(US9023785) What is claimed is: 1.  A process for producing bis-N-alkyl polyether, bis-N-alkenyl polyether, bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta or alpha-amino acids or their salts having the formula XII       where: R1 is independently a radical represented by  -- H or  -- CH3,   R2 is an alkyl, alkenyl chain, cycloalkyl or aryl;   R3 is a radical represented by  -- H,  -- CH3,  -- CH.dbd.CH -- CH3, or  -- COOX;   R4 is a radical represented by  -- H,  -- CH3, or  -- CH2 -- COOX;   R5 is a radical represented by  -- H, an alkyl, alkenyl, cycloalkyl, aryl group, or a metal;   R6 is a radical represented by an alkyl, alkenyl, cycloalkyl, or aryl group;   n and m can have values from 1 to 250, and   i can have values of 0 and 1: when i=1: R3 is a radical represented by  -- H,  -- CH3,  -- CH.dbd.CH -- CH3, or  -- COOX, and    when i is equal to 0: R3 is a radical represented by  -- COOX;    In the radical  -- COOX used in R3 and R4, X is represented by:    -- H, an alkyl, alkenyl group, a cycloalkyl or aryl group, or a metal;   wherein said process comprises the reaction scheme    wherein the secondary amine of Formula VIII is reacted with a compound of Formula IX to obtain the compound of Formula IX to obtain the compound of Formula X, wherein said compound of Formula IX is selected from the group consisting of unsaturated alpha or beta acids and salts thereof, halogenated acids and salts thereof, and unsaturated esters, and   reacting the resulting compound of Formula X with a compound of Formula XI, where X is selected from the group consisting of bromide, chloride and iodide, and R6 is as defined above to obtain the compound of Formula XII. 2. The process of claim 1, wherein the ratio of the compound of Formula VIII to the compound of Formula IX is 1:1.5 to 1:4. 3. The process of claim 2, wherein the reaction of the compound of Formula VIII and the compound of Formula IX is carried out in the presence of a solvent selected from the group consisting of water, alcohol, and aromatic hydrocarbons at a temperature of 40 to 180 deg. C. and atmospheric pressure. 4. The process of claim 3, wherein said reaction of the compound of Formula X and said compound of Formula XI is carried out at a ratio of 1:1 to 1:4. 5. The process of claim 4, wherein said reaction of the compound of Formula X and said compound of Formula XI is carried out at a temperature of 15 deg. C. to 90 deg. C. at a pressure of 585 to 760 mmHg. 6. The process of claim 1, wherein the compound of Formula IX is selected from the group consisting of acrylic acid, methacrylic acid, itaconic acid, crotonic acid, fumaric acid, isocrotonic acid, angelic acid, maleic acid, methyl acrylate and methyl methacrylate. 7. The process of claim 1, wherein the molar ratio of compounds of Formula VIII and IX is 1:1.8 to 1:2.6. 8. The process of claim 1, wherein the compound of Formula XI is a linear or branched alkyl or alkenyl halide and contains 1 to 30 carbon atoms. 9. The process of claim 1, wherein the compound of Formula XI is a cycloalkyl or aryl containing 5 to 12 carbon atoms. 10. The process of claim 1, wherein the molar ratio of compounds of Formula X and XI is 1:1.5 to 1:2.6. 11. The process of claim 1, wherein said compound of Formula VIII is obtained by reacting a compound of Formula I with a compound of Formula II to obtain a compound of Formula III, and thereafter reducing the compound of Formula III to obtain the secondary amine of Formula VIII, according to the following reaction scheme       where A is selected from the group consisting of carboxylic acid, carboxylic acid ester, alkyl halide, alkenyl halide, cycloalkyl and aryl. 12. The process of claim 11, wherein said compound of Formula III is reduced to the compound of Formula VIII by reacting with a hydride or by catalytic hydrogenation. 13. The process of claim 11, wherein the compound of Formula I is a polyether derived from ethylene oxide or propylene oxide or copolymers thereof with two amino groups, one at a terminal end and the other at a beginning of the polymer chain and having a molecular weight in the range of 100 to 20,000 g/mol. 14. The process of claim 11, wherein A of the compound of Formula II is a linear or branched alkyl or alkenyl halide and contains 1 to 30 carbon atoms. 15. The process of claim 1, wherein said compound of Formula VIII is obtained by reacting a compound of Formula IV with a compound B of Formula V selected from the group consisting of tosyl chloride, mesyl chloride, bromine, chlorine, and penta or tri chloride or bromide phosphorous, to obtain the compound of Formula VI, and reacting the compound of Formula VI by nucleophilic substitution with a compound of Formula VII to obtain the compound of Formula VIII, according to the reaction scheme    where the compound of Formula VII is selected from the group consisting of alkyl, alkenyl, cycloalkyl and aryl amines. 16. The process of claim 15, wherein said compound of Formula IV and compound B of Formula V are reacted in a ratio of 1:2 to 1:4 with sodium, potassium or cesium hydroxide at a temperature of 0-25 deg. C. 17. The process of claim 16, wherein said compound of Formula IV and compound B of Formula V is in a solvent selected from the group consisting of water, tetrahydrofuran, acetonitrile, and mixtures thereof. 18. The process of claim 17, wherein said compound of Formula VI is reacted with said compound of Formula VII at a ratio of 1:15 to 1:4 at a temperature of 60-100 deg. C. 19. The process of claim 18, wherein said compound of Formula VI is reacted with said compound of Formula VII in a solvent selected from the group consisting of acetonitrile, dimethylformamide, dimethylsulfoxide, acetone and short chain alcohols. 20. The process of claim 15, wherein the compound of Formula IV is a glycol derived from ethylene oxide or propylene oxide or copolymers thereof with two hydroxyl groups, one at a terminal end and the other at a beginning of the polymer chain, and has a molecular weight in the range of 100 to 20,000 g/mol. 21. The process of claim 15, wherein the molar ratio of the compound of Formula IV and compound B of Formula V is 1:2.2 to 1:2.6. 22. The process of claim 15, wherein the compound of Formula VII is linear or branched cycloalkyl or aryl amine and containing 5 to 12 carbon atoms. 23. The process of claim 15, wherein the molar ratio of compounds of Formula VI and VII is 1:1.8 to 1:2.6. 24. A method of inhibiting corrosion of ferrous metals in contact with a liquid selected from the group consisting of crude oil, liquid fuels and water, said method comprising adding a corrosion inhibitor to said liquid, said corrosion inhibitor comprising a Gemini surfactant bis-N-alkyl polyether, bis-N-alkenyl polyether, bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta or alpha-amino acids or their salts in an amount to inhibit corrosion of said ferrous metals, wherein said Gemini surfactants have the formula       where: R1 is independently a radical represented by  -- H or  -- CH3,   R2 is an alkyl, alkenyl chain, cycloalkyl or aryl;   R3 is a radical represented by  -- H,  -- CH3,  -- CH.dbd.CH -- CH3, or  -- COOX;   R4 is a radical represented by  -- H,  -- CH3, or  -- CH2 -- COOX;   R5 is a radical represented by  -- H, an alkyl, alkenyl, cycloalkyl, aryl group, or a metal;   R6 is a radical represented by an alkyl, alkenyl, cycloalkyl, or aryl group;   n and m can have values from 1 to 250, and   i can have values of 0 and 1: when i=1: R3 is a radical represented by  -- H,  -- CH3,  -- CH.dbd.CH -- CH3, or  -- COOX, and    when i is equal to 0: R3 is a radical represented by  -- COOX;    In the radical  -- COOX used in R3 and R4, X is represented by:     -- H, an alkyl, alkenyl group, a cycloalkyl or aryl group, or a metal. 25. The method of claim 24, wherein said corrosion inhibitor comprises 1 to 100 weight percent of said Gemini surfactant. 26. The method of claim 24, wherein said corrosion inhibitor includes a solvent selected from the group consisting of distilled water, brine with a divalent ion selected from the group consisting of calcium, magnesium, strontium and barium, and organic compounds selected from the group consisting of methanol, ethanol, isopropanol, xylene, toluene, diesel, gasoline or mixtures at a concentration of 1 to 99 wt %. 27. The method of claim 24, wherein said corrosion inhibitor is present in an amount of 0.5 to 10,000 ppm.
法律状态
(US9023785) LEGAL DETAILS FOR US2013340326  Actual or expected expiration date=2031-02-13    Legal state=ALIVE    Status=GRANTED     Event publication date=2013-07-18  Event code=US/APP  Event indicator=Pos  Event type=Examination events  Application details  Application country=US US13945307  Application date=2013-07-18  Standardized application number=2013US-13945307     Event publication date=2013-12-26  Event code=US/A1  Event type=Examination events  Application published  Publication country=US  Publication number=US2013340326  Publication stage Code=A1  Publication date=2013-12-26  Standardized publication number=US20130340326     Event publication date=2015-05-05  Event code=US/B2  Event indicator=Pos  Event type=Event indicating In Force  Granted patent as second publication  Publication country=US  Publication number=US9023785  Publication stage Code=B2  Publication date=2015-05-05  Standardized publication number=US9023785     Event publication date=2015-05-05  Event code=US/354  Event indicator=Pos  Event type=Event indicating In Force  Event type=Extension of term of duration of protection  Patent term extension under  35 U.S.C 154(b) until/for:  Number of days of extension=61
专利类型码
A1B2
国别省市代码
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