Chemical compounds

Abstract

The present invention relates to novel compounds of polyfunctionalized polyethylene and polypropylene glycols, their synthesis and their use, in particular as tracers in applications related to oil and gas production, and especially as specific markers of various target fluids.

Claims

1. A compound of the following formula:
R.sup.1R.sup.2R.sup.3(OCHR.sup.4CH.sub.2).sub.nR.sup.5[(CH.sub.2CHR.sup.6O).sub.mR.sup.7R.sup.8R.sup.9].sub.p, wherein: R.sup.5 is selected from the group consisting of: ##STR00039## ##STR00040## ##STR00041## ##STR00042## R.sup.4 and R.sup.6 are H or CH.sub.3 to give PEG or PPG chains; n and m are integers between 2 and 12 in which n is the same or different from m; p is an integer between 1 and 3 depending on R.sup.5; R.sup.3 and R.sup.7 are alkylic or alkenylic or aromatic hydrocarbon moieties with 2-40 carbon coupled to the PEG units or the PPG units by an ester or ether bond; R.sup.2 and R.sup.8 are H; R.sup.1 and R.sup.9 are sulfonic or phosphonic acid groups; or salts, hydrates and solvates thereof; or a compound selected from the group consisting of: 1,2-bis(2-(2-(2-(benzyloxy)ethoxy)ethoxy)ethoxy)benzene, 1,2-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13-yl)oxy)benzene, 1,2-bis((1-phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl)oxy)benzene, 1,2-bis((1-phenyl-2,5,8,11,14,17-hexaoxanonadecan-19-yl)oxy)benzene, 1,2-bis((1-phenyl-2,5,8,11,14,17,20,23-octaoxapentacosan-25-yl)oxy)benzene, 1,2-bis(2-(2-((4-methylbenzyl)oxy)ethoxy)ethoxy)benzene, 1,2-bis(2-(2-(2-((4-methylbenzyl)oxy)ethoxy)ethoxy)ethoxy)benzene, 1,2-bis((1-(p-tolyl)-2,5,8,11-tetraoxatridecan-13-yl)oxy)benzene, 1,2-bis((1-(p-tolyl)-2,5,8,11,14-pentaoxahexadecan-16-yl)oxy)benzene, 1,2-bis((1-(p-tolyl)-2,5,8,11,14,17-hexaoxanonadecan-19-yl)oxy)benzene, 1,2-bis((1-(4-(tert-butyl)phenyl)-2,5,8,11-tetraoxatridecan-13-yl)oxy)benzene, 1,2-bis((1-(4-(tert-butyl)phenyl)-2,5,8,11,14,17,20,23-octaoxapentacosan-25-yl)oxy)benzene, 1,2-bis(2-(2-(naphthalen-2-ylmethoxy)ethoxy)ethoxy)benzene, 1,2-bis((1-naphthalen-2-yl)-2,5,8,11,14,17-hexaoxanonadecan-19-yl)oxy)benzene, 1,3-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13-yl)oxy)benzene, (((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))dibenzene, (((((((((4-methyl-1,2-phenylene)bis(oxy))bis ethane-2,1-diyl))bis ox))bis ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))dibenzene, 13,13-((4-methyl-1,2-phenylene)bis(oxy))bis(1-phenyl-2,5,8,11-tetraoxatridecane), 16,16-(4-methyl-1,2-phenylene)bis(oxy))bis(1-phenyl-2,5,8,11,14-pentaoxahexadecane), 19,19-(4-methyl-1,2-phenylene)bis(oxy))bis(1-phenyl-2,5,8,11,14,17-hexaoxanonadecane), 25,25-((4-methyl-1,2-phenylene)bis(oxy))bis(1-phenyl-2,5,8,11,14,17,20,23-octaoxapentacosane), 4,4-((((((4-methyl-1,2-phenylene)bis(oxy))bis ethane-2,1-diyl))bis(oxy))bis ethane-2,1-diyl))bis(oxy))bis(methylene))bis(methylbenzene), 4,4-(((((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))bis(methylbenzene), 13,13-((4-methyl-1,2-phenylene)bis(oxy))bis(1-(p-tolyl)-2,5,8,11-tetraoxatridecane), 16,16-(4-methyl-1,2-phenylene)bis(oxy))bis(1-(p-tolyl)-2,5,8,11,14-pentaoxahexadecane), 19,19-((4-methyl-1,2-phenylene)bis(oxy))bis(1-(p-tolyl)-2,5,8,11,14,17-hexaoxanonadecane), 4,4-((((((4-ethyl-1,3-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))bis(methylbenzene), 13,13-((4-ethyl-1,3-phenylene)bis(oxy))bis(1-(p-tolyl)-2,5,8,11-tetraoxatridecane), 19,19-((4-ethyl-1,3-phenylene)bis(ox))bis(1-(p-tolyl)-2,5,8,11,14,17-hexaoxanonadecane), (((((((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))dibenzene, (((((((((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))dibenzene, 13,13-((4-(tert-butyl)-1,2-phenylene)bis(ox))bis(1-phenyl-2,5,8,11-tetraoxatridecane), 16,16-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1-phenyl-2,5,8,11,14-pentaoxahexadecane), 19,19-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1-phenyl-2,5,8,11,14,17-hexaoxanonadecane), 25,25-((4-(tert-butyl)-1,2-phenylene)bis(ox))bis(1-phenyl-2,5,8,11,14,17,20,23-octaoxapentacosane), 4,4-(((((((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))bis(methylbenzene), 4,4-((((((((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))bis(methylbenzene), 13,13-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1-(p-tolyl)-2,5,8,11-tetraoxatridecane), 16,16-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1-(p-tolyl)-2,5,8,11,14-pentaoxahexadecane), 19,19-((4-(tert-butyl)-1,2-phenylene)bis(ox))bis(1-(p-tolyl)-2,5,8,11,14,17-hexaoxanonadecane), 25,25-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1-(4-(tert-butyl)phenyl)-2,5,8,11,14,17,20,23-octaoxapentacosane), 19,19-((4-(tert-butyl)-1,2-phenylene)bis(ox))bis(1-(naphthalen-2-yl)-2,5,8,11,14,17-hexaoxanonadecane), (((((((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))dibenzene, 13,13-((3,5-di-tert-butyl-1,2-phenylene)bis ox))bis(1-phenyl-2,5,8,11-tetraoxatridecane), 19,19-((3,5-di-tert-butyl-1,2-phenylene)bis ox))bis(1-phenyl-2,5,8,11,14,17-hexaoxanonadecane), 25,25-((3,5-di-tert-butyl-1,2-phenylene)bis(ox))bis(1-phenyl-2,5,8,11,14,17,20,23-octaoxapentacosane), 13,13-((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))bis(1-(4-(tert-butyl)phenyl)-2,5,8,11-tetraoxatridecane), 25,25-((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))bis(14-(tert-butyl)phenyl)-2,5,8,11,14,17,20,23-octaoxapentacosane), 1,2-bis(15-phenyl-2,5,8,11,14-pentaoxapentadecyl)benzene, 1,2-bis 27-phenyl-2,5,8,11,14,17,20,23,26-nonaoxaheptacosyl)benzene, 1,2-bis 15-(4-(tert-butyl)phenyl)-2,5,8,11,14-pentaoxapentadecyl)benzene, 4,4-(((((((4-chloro-1,3-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))bis(methylbenzene), 13,13-(4-cloro-1,3-phenylene)bis ox))bis(1-(p-tolyl)-2,5,8,11-tetraoxatridecane), 1,5-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13-yl)oxy)naphthalene, 2,3-bis(2-(2-(benzyloxy)ethoxy)ethoxy)naphthalene, 2,3-bis(2-(2-(2-(benzyloxy)ethoxy)ethoxy)ethoxy)naphthalene, 2,3-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13-yl)oxy)naphthalene, 2,3-bis((1-phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl)oxy)naphthalene, 2,3-bis((1-phenyl-2,5,8,11,14,17-hexaoxanonadecan-19-yl)oxy)naphthalene, 2,3-bis((1-phenyl-2,5,8,11,14,17,20,23-octaoxapentacosan-25-yl)oxy)naphthalene, 2,3-bis(2-(2-((4-methylbenzyl)oxy)ethoxy)ethoxy)naphthalene, 2,3-bis(2-(2-(2-((4-methylbenzyl)oxy)ethoxy)ethoxy)ethoxy)naphthalene, 2,3-bis((1-(p-tolyl)-2,5,8,11-tetraoxatridecan-13-yl)oxy)naphthalene, 2,3-bis((1-(p-tolyl)-2,5,8,11,14-pentaoxahexadecan-16-yl)oxy)naphthalene, 2,3-bis(1-(p-tolyl)-2,5,8,11,14,17-hexaoxanonadecan-19-yl)oxy)naphthalene, 13,13-(propane-2,2-diylbis 4,1-phenylene))bis ox))bis(1-(p-tolyl)-2,5,8,11-tetraoxatridecane), 19,19-((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(1-(p-tolyl)-2,5,8,11,14,17-hexaoxanonadecane), 1,33-bis 4-tert-butyl)phenyl)-15,19-dimethyl-2,5,8,11,14,17,20,23,26,29,32-undecaoxatritriacontane, 1,56-diphenyl-2,5,8,11,14,17,20,23,26,31,34,37,40,43,46,49,52,55-octadecaoxahexapentacontane, bis(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) succinate, bis(1-(4-(tert-butyl)phenyl)-2,5,8,11-tetraoxatridecan-13-yl) succinate, bis(1-(4-(tert-butyl)phenyl)-2,5,8,11,14,17,20,23-octaoxapentacosan-25-yl) succinate, bis(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) glutarate, bis(1-phenyl-2,5,8,11,14,17,20,23-octaoxapentacosan-25-yl) glutarate, bis(1-(4-(tert-butyl)phenyl)-2,5,8,11-tetraoxatridecan-13-yl) glutarate, bis(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) adipate, 1,3,5-tris((1-(4-tert-butyl)phenyl)-2,5,8,11-tetraoxatridecan-13-yl)oxy)benzene, 1,3,5-tris(1,5-phenyl-2,5,8,11,14-pentaoxapentadecyl)benzene, 1,3,5-tris(27-phenyl-2,5,8,11,14,17,20,23,26-nonaoxaheptacosyl)benzene, tris(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) benzene-1,3,5-tricarboxylate, 25,25-((4-ethyl-1,3-phenylene)bis(ox))bis(1-phenyl-2,5,8,11,14,17,20,23-octaoxapentacosane), 1,2-bis((1-(naphthalen-2-yl)-2,5,8,11-tetraoxatridecan-13-yl)oxy)benzene, 2,2-(((((((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))dinaphthalene, and 13,13-((4-(tert-butyl)-1,2-phenylene)bis(ox))bis(1-(naphthalen-2-yl)-2,5,8,11-tetraoxatridecane).

2. The compound according to claim 1, wherein n and m are integers between 3 and 12.

3. The compound according to claim 1, which is selected from the group consisting of: potassium 3,3-(((((1,2-phenylenebis(oxy))bis(ethane-21-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(propane-1-sulfonate), potassium 3,3-(((((((1,2-phenylenebis(oxy))bis(ethane-21-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(propane-1-sulfonate), potassium 1,1-(1,2-phenylenebis(oxy))bis(3,6,9,12-tetraoxapentadecane-15-sulfonate), potassium 1,1-(1,2-phenylenebis(oxy))bis(3,6,9,12,15,18-hexaoxahenicosane-21-sulfonate), potassium 1,1-(1,2-phenylenebis(oxy))bis(3,6,9,12,15,18,21,24-octaoxaheptacosane-27-sulfonate), potassium 4,4-(((((1,2-phenylenebis(ox))bis(ethane-2,1-diyl))bis(ox))bis(ethane-2,1-diyl))bis(oxy))bis(butane-1-sulfonate), potassium 1,1-(1,2-phenylenebis(oxy))bis(3,6,9,12-tetraoxahexadecane-16-sulfonate), potassium 1,1-(1,2-phenylenebis(ox))bis(3,6,9,12,15,18-hexaoxadocosane-22-sulfonate), potassium 1,1-(1,2-phenylenebis(oxy))bis(3,6,9,12,15,18,21,24-octaoxaoctacosane-28-sulfonate), potassium 3,3-((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(propane-1-sulfonate), potassium 1,1-((4-methyl-1,2-phenylene)bis(ox))bis(3,6,9,12-tetraoxapentadecane-15-sulfonate), potassium 1,1-((4-methyl-1,2-phenylene)bis(oxy))bis(3,6,9,12,15,18-hexaoxahenicosane-21-sulfonate, potassium 1,1-((4-methyl-1,2-phenylene)bis ox))bis 3,6,9,12,15,18,21,24-octaoxaheptacosane-27-sulfonate), potassium 4,4-((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(butane-1-sulfonate), potassium 1,1-((4-methyl-1,2-phenylene)bis(oxy))bis 3,6,9,12-tetraoxahexadecane-16-sulfonate), potassium 1,1-((4-methyl-1,2-phenylene)bis(oxy))bis(3,6,9,12,15,18-hexaoxadocosane-22-sulfonate, potassium 1,1-((4-methyl-1,2-phenylene)bis(oxy))bis 3,6,9,12,15,18,21,24-octaoxaoctacosane-28-sulfonate), potassium 1,1-((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(pentane-3-sulfonate), potassium 4,4-((((((4-methyl-1,2-phenylene)bis(oxy))bis ethane-2,1-diyl))bis(oxy))bis ethane-2,1-diyl))bis(oxy))bis(1-phenylbutane-2-sulfonate), potassium 1,1-((4-methyl-1,2-phenylene)bis(oxy))bis(28-phenyl-3,6,9,12,15,18,21,24-octaoxaoctacosane-27-sulfonate), potassium 3,3-((((((4-ethyl-1,3-phenylene)bis(oxy))bis ethane-2,1-diyl))bis(oxy))bis ethane-2,1-diyl))bis(oxy))bis(propane-1-sulfonate), potassium 1,1-((4-ethyl-1,3-phenylene)bis(oxy))bis(3,6,9,12-tetraoxapentadecane-15-sulfonate), potassium 1,1-((4-ethyl-1,3-phenylene)bis(oxy))bis(3,6,9,12,15,18-hexaoxahenicosane-2,1-sulfonate), potassium 1,1-((4-ethyl-1,3-phenylene)bis(oxy))bis(3,6,9,12,15,18,21,24-octaoxaheptacosane-27-sulfonate), potassium 4,4-((((((4-ethyl-1,3-phenylene)bis(oxy))bis ethane-2,1-diyl))bis(oxy))bis ethane-2,1-diyl))bis(oxy))bis(butane-1-sulfonate), potassium 1,1-((4-ethyl-1,3-phenylene)bis(oxy))bis(3,6,9,12-tetraoxahexadecane-16-sulfonate), potassium 1,1-((4-ethyl-1,3-phenylene)bis(oxy))bis 3,6,9,12,15,18-hexaoxadocosane-22-sulfonate), potassium 1,1-((4-ethyl-1,3-phenylene)bis(oxy))bis(3,6,9,12,15,18,21,24-octaoxaoctacosane-28-sulfonate), potassium 3,3-((((((4-tert-butyl)-1,2-phenylene)bis(oxy))bis ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis propane-1-sulfonate), potassium 1,1-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(3,6,9,12-tetraoxapentadecane-15-sulfonate), potassium 1,1-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis 3,6,9,12,15,18-hexaoxahenicosane-21-sulfonate), potassium 1,1-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(3,6,9,12,15,18,21,24-octaoxaheptacosane-27-sulfonate), potassium 4,4-((((((4-tert-butyl)-1,2-phenylene)bis(oxy))bis ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(butane-1-sulfonate), potassium 1,1-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(3,6,9,12-tetraoxahexadecane-16-sulfonate), potassium 1,1-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis 3,6,9,12,15,18-hexaoxadocosane-22-sulfonate, potassium 1,1-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(3,6,9,12,15,18,21,24-octaoxaoctacosane-28-sulfonate), potassium 1,1-((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))bis 3,6,9,12-tetraoxapentadecane-15-sulfonate, potassium 1,1-((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))bis(3,6,9,12,15,18-hexaoxahenicosane-21-sulfonate), potassium 1,1-((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))bis(3,6,9,12-tetraoxahexadecane-16-sulfonate), potassium 3,3-((((((4-chloro-1,3-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(propane-1-sulfonate), potassium 1,1-((4-chloro-1,3-phenylene)bis(oxy))bis(3,6,9,12-tetraoxapentadecane-15-sulfonate), potassium 4,4-((((((4-chloro-1,3-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(butane-1-sulfonate), potassium 1,1-((4-chloro-1,3-phenylene)bis(oxy))bis(3,6,9,12-tetraoxahexadecane-16-sulfonate), potassium 3,3-(((((naphthalene-2,3-diylbis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(propane-1-sulfonate), potassium 1,1-(naphthalene-2,3-diylbis(oxy))bis(3,6,9,12-tetraoxapentadecane-15-sulfonate), potassium 1,1-(naphthalene-2,3-diylbis(oxy))bis(3,6,9,12,15,18-hexaoxahenicosane-21-sulfonate), potassium 1,1-(naphthalene-2,3-diylbis(ox))bis(3,6,9,12,15,18,21,24-octaoxaheptacosane-27-sulfonate), potassium 4,4-(((((naphthalene-2,3-diylbis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(butane-1-sulfonate), potassium 1,1-(naphthalene-2,3-diylbis(oxy))bis(3,6,9,12-tetraoxahexadecane-16-sulfonate), potassium 1,1-(naphthalene-2,3-diylbis(ox))bis(3,6,9,12,15,18-hexaoxadocosane-22-sulfonate), potassium 1,1-(naphthalene-2,3-diylbis(oxy))bis(3,6,9,12,15,18,21,24-octaoxaoctacosane-28-sulfonate), 1,1-(1,2-phenylenebis(ox))bis(3,6,9,12,15,18,21,24-octaoxaoctacosane-28-sulfonic acid), 25,25-((4-ethyl-1,3-phenylene)bis(ox))bis(1-phenyl-2,5,8,11,14,17,20,23-octaoxapentacosane), and potassium 1,1-((4-methyl-1,2-phenylene)bis(oxy))bis(3,6,9,12-tetraoxaheptadecane-15-sulfonate).

4. A compound according to claim 1, as tracers by LC-MS.

5. A composition comprising at least one compound according to claim 1 and at least one additional constituent selected from the group consisting of a solvent, a diluent, a surfactant, an absorbent and a stabilizer.

6. The composition according to claim 5, wherein the composition is formulated into a tablet, capsule, matrix or other geometric shape.

7. A method of using a compound according to claim 1 as a tracer, comprising injecting the compound into an oil and gas well and then later detecting the compound.

8. The method according to claim 7, wherein the compound is later detected topside after release from the oil and gas well.

9. The method according to claim 7, wherein the compound is later detected topside after release from the oil and gas well by LCMS, GCMS or a combination thereof.

10. A method of marking a fluid for permanent inflow monitoring, comprising implementing at least two compounds according to claim 1 into or onto a material.

11. The method according to claim 10, wherein the material is at least one material selected from the group consisting of a polymer, a ceramic, sand, shale, completion equipment, a tool and a pipe.

12. The method according to claim 10, further comprising implementing an additive into the material in combination with the at least two compounds.

13. A method of using 1,2-bis(2-(2-(benzyloxy)ethoxy)ethoxy)benzene as a tracer, comprising injecting 1,2-bis(2-(2-(benzyloxy)ethoxy)ethoxy)benzene into an oil and gas well and then later detecting the 1,2-bis(2-(2-(benzyloxy)ethoxy)ethoxy)benzene.

14. The method according to claim 13, wherein the 1,2-bis(2-(2-(benzyloxy)ethoxy)ethoxy)benzene is later detected topside after release from the oil and gas well.

15. The method according to claim 13, wherein the 1,2-bis(2-(2-(benzyloxy)ethoxy)ethoxy)benzene is later detected topside after release from the oil and gas well by LCMS, GCMS or a combination thereof.

16. A method of marking a fluid for permanent inflow monitoring, comprising implementing 1,2-bis(2-(2-(benzyloxy)ethoxy)ethoxy)benzene and at least one compound according to claim 1 into or onto a material.

17. The method according to claim 16, wherein the material is at least one material selected from the group consisting of a polymer, a ceramic, sand, shale, completion equipment, a tool and a pipe.

18. The method according to claim 16, further comprising implementing an additive into the material in combination with the 1,2-bis(2-(2-(benzyloxy)ethoxy)ethoxy)benzene and the at least one compound according to claim 1.

Description

LIST OF FIGURES

(1) FIG. 1 MS scan of product 1,2-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13-yl)oxy)benzene obtained from synthesis in example 1

(2) FIG. 2 MS scan of product bis(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) glutarate obtained from synthesis in example 2

(3) FIG. 3 MS scan of crude product tris(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) benzene-1,3,5-tricarboxylate obtained from synthesis in example 3

(4) FIG. 4 MS scan of purified product tris(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) benzene-1,3,5-tricarboxylate obtained from synthesis in example 3

(5) FIG. 5 MS scan of product 1,1-(1,2-henylenebis(oxy))bis(3,6,9,12,15,18,21,24-octaoxaoctacosane-28-sulfonic acid) obtained from synthesis in example 4

(6) FIG. 6 MS scan of product 1,2-bis(2-(2-(benzyloxy)ethoxy)ethoxy)benzene obtained from synthesis in example 5

(7) FIG. 7 MS scan of product 2,3-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13-yl)oxy)naphthalene obtained from synthesis in example 6

(8) FIG. 8 MS scan of product potassium 3,3-(((((1,2-phenylenebis(oxy)) bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(propane-1-sulfonate) obtained from synthesis in example 7

(9) FIG. 9 MS scan of product potassium 1,1-(1,2-phenylenebis(oxy))bis(3,6,9,12-tetraoxapentadecane-15-sulfonate) obtained from synthesis in example 8

(10) FIG. 10 MS scan of product potassium 1,1-((4-methyl-1,2-phenylene)bis(oxy))bis(3,6,9,12-tetraoxapentadecane-15-sulfonate) obtained from synthesis in example 9

(11) FIG. 11 MS scan of product potassium 1,1-((4-methyl-1,2-phenylene)bis(oxy))bis(3,6,9,12-tetraoxahexadecane-16-sulfonate) obtained from synthesis in example 10

(12) FIG. 12 MS scan of product 4,4-(((((((4-ethyl-1,3-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))bis(methylbenzene) obtained from synthesis in example 11

(13) FIG. 13 MS scan of product 13,13-((4-ethyl-1,3-phenylene)bis(oxy))bis(1-(p-tolyl)-2,5,8,11-tetraoxatridecane) obtained from synthesis in example 12

(14) FIG. 14 MS scan of product 19,19-((4-ethyl-1,3-phenylene)bis(oxy))bis(1-(p-tolyl)-2,5,8,11,14,17-hexaoxanonadecane) obtained from synthesis in example 13

(15) FIG. 15 MS scan of product 25,25-((4-ethyl-1,3-phenylene)bis(oxy))bis(1-phenyl-2,5,8,11,14,17,20,23-octaoxapentacosane) obtained from synthesis in example 14

(16) FIG. 16 MS scan of product 13,13-((4-chloro-1,3-phenylene)bis(oxy))bis(1-(p-tolyl)-2,5,8,11-tetraoxatridecane) obtained from synthesis in example 15

(17) FIG. 17 MS scan of product potassium 4,4-((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(1-phenylbutane-2-sulfonate) obtained from synthesis in example 16

(18) FIG. 18 MS scan of product potassium 1,1-((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(pentane-3-sulfonate) obtained from synthesis in example 17

(19) FIG. 19 MS scan of product potassium 1,2-bis(15-(4-(tert-butyl)phenyl)-2,5,8,11,14-pentaoxapentadecyl)benzene obtained from synthesis in example 18

(20) FIG. 20 MS scan of product potassium 1,2-bis(15-phenyl-2,5,8,11,14-pentaoxapentadecyl)benzene obtained from synthesis in example 19

(21) FIG. 21 MS scan of product potassium 1,2-bis(27-phenyl-2,5,8,11,14,17,20,23,26-nonaoxaheptacosyl)benzene obtained from synthesis in example 20

(22) FIG. 22 MS scan of product potassium 1,33-bis(4-(tert-butyl)phenyl)-15,19-dimethyl-2,5,8,11,14,17,20,23,26,29,32-undecaoxatritriacontane obtained from synthesis in example 21

(23) FIG. 23 MS scan of product potassium 1,32-diphenyl-2,5,8,11,14,19,22,25,28,31-decaoxadotriacontane obtained from synthesis in example 22

(24) FIG. 24 MS scan of product potassium 1,3,5-tris(15-phenyl-2,5,8,11,14-pentaoxapentadecyl)benzene obtained from synthesis in example 23

(25) FIG. 25 MS scan of product potassium 1,3,5-tris(27-phenyl-2,5,8,11,14,17,20,23,26-nonaoxaheptacosyl)benzene obtained from synthesis in example 24

EXAMPLES

(26) The examples given are only illustrations within the scope of the claims and not intended to limit the scope of the invention. The general synthetic schemes are described above. All the MS spectra are run from FAC/AMAC buffers and hence all the masses are represented by the ammonia adduct M+18 (for single ions) and (M+36)/2 for double ions. The MS is regular scans using electrospray ionization and positive mode settings.

Example 1

(27) Synthesis According to Scheme 1 and 2.

(28) MS Spectrum No 1.

(29) ##STR00015##

1,2-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13-yl)oxy)benzene

Example 2

(30) Synthesis According to Scheme 5.

(31) MS Spectrum No 2.

(32) ##STR00016##

Bis(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) glutarate

Example 3

(33) Synthesis According to Scheme 5.

(34) MS Spectrum No. 3 of Reaction Mixture and MS Spectrum No. 4 of Purified Product No 4.

(35) ##STR00017##

tris(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) benzene-1,3,5-tricarboxylate

Example 4

(36) Synthesis According to Scheme 1, 2 and 4

(37) MS Spectrum No 5

(38) ##STR00018##

1,1-(1,2-phenylenebis(oxy))bis(3,6,9,12,15,18,21,24-octaoxaoctacosane-28-sulfonic acid)

Example 5

(39) Synthesis According to Scheme 1 and 2

(40) MS Spectrum No 6

(41) ##STR00019##

1,2-bis(2-(2-(benzyloxy)ethoxy)ethoxy)benzene

Example 6

(42) Synthesis According to Scheme 1 and 2

(43) MS Spectrum No 7

(44) ##STR00020##

2,3-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13-yl)oxy)naphthalene

Example 7

(45) Synthesis According to Schemes 1, 2 and 4

(46) MS Spectrum No 8

(47) ##STR00021##

Potassium 3,3-(((((1,2-phenylenebis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(propane-1-sulfonate)

Example 8

(48) Synthesis According to Schemes 1, 2 and 4

(49) MS Spectrum No 9

(50) ##STR00022##

Potassium 1,1-(1,2-phenylenebis(oxy))bis(3,6,9,12-tetraoxapentadecane-15-sulfonate)

Example 9

(51) Synthesis According to Schemes 1, 2 and 4

(52) MS Spectrum No 10

(53) ##STR00023##

Potassium 1,1-((4-methyl-1,2-phenylene)bis(oxy))bis(3,6,9,12-tetraoxapentadecane-15-sulfonate)

Example 10

(54) Synthesis According to Schemes 1, 2 and 4

(55) MS Spectrum No 11

(56) ##STR00024##

Potassium 1,1-((4-methyl-1,2-phenylene)bis(oxy))bis(3,6,9,12-tetraoxahexadecane-16-sulfonate)

Example 11

(57) Synthesis According to Schemes 1 and 3

(58) MS Spectrum No 12

(59) ##STR00025##

4,4-(((((((4-ethyl-1,3-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(methylene))bis(methylbenzene)

Example 12

(60) Synthesis According to Schemes 1 and 3

(61) MS Spectrum No 13

(62) ##STR00026##

13,13-((4-ethyl-1,3-phenylene)bis(oxy))bis(1-(p-tolyl)-2,5,8,11-tetraoxatridecane)

Example 13

(63) Synthesis According to Schemes 1 and 3

(64) MS Spectrum No 14

(65) ##STR00027##

19,19-((4-ethyl-1,3-phenylene)bis(oxy))bis(1-(p-tolyl)-2,5,8,11,14,17-hexaoxanonadecane)

Example 14

(66) Synthesis According to Schemes 1 and 3

(67) MS Spectrum No 15

(68) ##STR00028##

25,25-((4-ethyl-1,3-phenylene)bis(oxy))bis(1-phenyl-2,5,8,11,14,17,20,23-octaoxapentacosane)

Example 15

(69) Synthesis According to Schemes 1 and 3

(70) MS Spectrum No 16

(71) ##STR00029##

13,13-((4-chloro-1,3-phenylene)bis(oxy))bis(1-(p-tolyl)-2,5,8,11-tetraoxatridecane)

Example 16

(72) Synthesis According to Schemes 1, 2 and 4

(73) MS Spectrum No 17

(74) ##STR00030##

Potassium 4,4-((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(1-phenylbutane-2-sulfonate)

Example 17

(75) Synthesis According to Schemes 1, 2 and 4

(76) MS Spectrum No 18

(77) ##STR00031##

Potassium 1,1-((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(pentane-3-sulfonate)

Example 18

(78) Synthesis According to Schemes 1 and 7

(79) MS Spectrum No 19

(80) ##STR00032##

1,2-bis(15-(4-(tert-butyl)phenyl)-2,5,8,11,14-pentaoxapentadecyl)benzene

Example 19

(81) Synthesis According to Schemes 1 and 7

(82) MS Spectrum No 20

(83) ##STR00033##

1,2-bis(15-phenyl-2,5,8,11,14-pentaoxapentadecyl)benzene

Example 20

(84) Synthesis According to Schemes 1 and 7

(85) MS Spectrum No 21

(86) ##STR00034##

1,2-bis(27-phenyl-2,5,8,11,14,17,20,23,26-nonaoxaheptacosyl)benzene

Example 21

(87) Synthesis According to Schemes 1 and 6

(88) MS Spectrum No 22

(89) ##STR00035##

1,33-bis(4-(tert-butyl)phenyl)-15,19-dimethyl-2,5,8,11,14,17,20,23,26,29,32-undecaoxatritriacontane

Example 22

(90) Synthesis According to Schemes 1 and 8

(91) MS Spectrum No 23

(92) ##STR00036##

1,32-diphenyl-2,5,8,11,14,19,22,25,28,31-decaoxadotriacontane

Example 23

(93) Synthesis According to Schemes 1 and 9

(94) MS Spectrum No 24

(95) ##STR00037##

1,3,5-tris(15-phenyl-2,5,8,11,14-pentaoxapentadecyl)benzene

Example 24

(96) Synthesis According to Schemes 1 and 9

(97) MS Spectrum No 25

(98) ##STR00038##

1,3,5-tris(27-phenyl-2,5,8,11,14,17,20,23,26-nonaoxaheptacosyl)benzene

(99) The table below is an overview of synthesized compounds and their main mass peak(s) (m+n*18/n*z), where n=number of ion charges, as a NH.sub.4-M adducts. The observed molecular adducts are used for product identifications in LC-MS analysis. The 24 examples above can be found in the table with reference in the third column and the fourth column refers to the synthetic methods used and described earlier in scheme 1-9.

(100) TABLE-US-00001 Ex. Scheme m/z. as Chemical name No. no. NH.sub.4 adduct 1 1,2-bis(2-(2-(benzyloxy)ethoxy)ethoxy)benzene 5 1.2 484.3 2 1,2-bis(2-(2-(2-(benzyloxy)ethoxy)ethoxy)ethoxy)benzene 1.2 572.3 3 1,2-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13- 1 1.2 660.4 yl)oxy)benzene 4 1,2-bis((1-phenyl-2,5,8,11,14-pentaoxahexadecan-16- 1.2 748.5 yl)oxy)benzene 5 1,2-bis((1-phenyl-2,5,8,11,14,17-hexaoxanonadecan-19- 1.2 836.5 yl)oxy)benzene 6 1,2-bis((1-phenyl-2,5,8,11,14,17,20,23- 1.2 1012.6/ octaoxapentacosan-25-yl)oxy)benzene 515.4 7 1,2-bis(2-(2-((4-methylbenzyl)oxy)ethoxy)ethoxy)benzene 1.2 512.4 8 1,2-bis(2-(2-(2-((4- 1.2 600.4 methylbenzyl)oxy)ethoxy)ethoxy)ethoxy)benzene 9 1,2-bis((1-(p-tolyl)-2,5,8,11-tetraoxatridecan-13- 1.2 688.5 yl)oxy)benzene 10 1,2-bis((1-(p-tolyl)-2,5,8,11,14-pentaoxahexadecan-16- 1.2 776.4 yl)oxy)benzene 11 1,2-bis((1-(p-tolyl)-2,5,8,11,14,17-hexaoxanonadecan-19- 1.2 864.5 yl)oxy)benzene 12 1,2-bis((1-(4-(tert-butyl)phenyl)-2,5,8,11-tetraoxatridecan- 1.2 772.5 13-yl)oxy)benzene 13 1,2-bis((1-(4-(tert-butyl)phenyl)-2,5,8,11,14,17,20,23- 1.2 1124.7/ octaoxapentacosan-25-yl)oxy)benzene 571.5 14 1,2-bis(2-(2-(naphthalen-2- 1.2 584.4 ylmethoxy)ethoxy)ethoxy)benzene 15 1,2-bis((1-(naphthalen-2-yl)-2,5,8,11,14,17- 1.2 936.4 hexaoxanonadecan-19-yl)oxy)benzene 16 1,3-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13- 1.3 660.4 yl)oxy)benzene 17 1,4-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13- 1.3 660.4 yl)oxy)benzene 18 (((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane-2,1- 1.2 498.4 diyl))bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(methylene))dibenzene 19 (((((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane-2,1- 1.2 586.3 diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(methylene))dibenzene 20 13,13-((4-methyl-1,2-phenylene)bis(oxy))bis(1-phenyl- 1.2 674.5 2,5,8,11-tetraoxatridecane) 21 16,16-((4-methyl-1,2-phenylene)bis(oxy))bis(1-phenyl- 1.2 762.5 2,5,8,11,14-pentaoxahexadecane) 22 19,19-((4-methyl-1,2-phenylene)bis(oxy))bis(1-phenyl- 1.2 850.6 2,5,8,11,14,17-hexaoxanonadecane) 23 25,25-((4-methyl-1,2-phenylene)bis(oxy))bis(1-phenyl- 1.2 1026.5/ 2,5,8,11,14,17,20,23-octaoxapentacosane) 522.4 24 4,4-(((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane- 1.2 526.4 2,1-diyl))bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(methylene))bis(methylbenzene) 25 4,4-(((((((((4-methyl-1,2-phenylene)bis(oxy))bis(ethane- 1.2 614.4 2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane- 2,1-diyl))bis(oxy))bis(methylene))bis(methylbenzene) 26 13,13-((4-methyl-1,2-phenylene)bis(oxy))bis(1-(p-tolyl)- 1.2 702.5 2,5,8,11-tetraoxatridecane) 27 16,16-((4-methyl-1,2-phenylene)bis(oxy))bis(1-(p-tolyl)- 1.2 790.5 2,5,8,11,14-pentaoxahexadecane) 28 19,19-((4-methyl-1,2-phenylene)bis(oxy))bis(1-(p-tolyl)- 1.2 878.6 2,5,8,11,14,17-hexaoxanonadecane) 29 4,4-(((((((4-ethyl-1,3-phenylene)bis(oxy))bis(ethane-2,1- 11 1.3 540.5 diyl))bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(methylene))bis(methylbenzene) 30 13,13-((4-ethyl-1,3-phenylene)bis(oxy))bis(1-(p-tolyl)- 12 1.3 716.4 2,5,8,11-tetraoxatridecane) 31 19,19-((4-ethyl-1,3-phenylene)bis(oxy))bis(1-(p-tolyl)- 13 1.3 892.5/ 2,5,8,11,14,17-hexaoxanonadecane) 455.4 32 (((((((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(ethane-2,1- 1.2 540.3 diyl))bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(methylene))dibenzene 33 (((((((((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(ethane- 1.2 628.5 2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane- 2,1-diyl))bis(oxy))bis(methylene))dibenzene 34 13,13-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1- 1.2 416.5 phenyl-2,5,8,11-tetraoxatridecane) 35 16,16-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1- 1.2 804.5 phenyl-2,5,8,11,14-pentaoxahexadecane) 36 19,19-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1- 1.2 892.6 phenyl-2,5,8,11,14,17-hexaoxanonadecane) 37 25,25-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1- 1.2 1068.5/ phenyl-2,5,8,11,14,17,20,23-octaoxapentacosane) 543.5 38 4,4-(((((((4-(tert-butyl)-1,2- 1.2 568.4 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(methylene))bis(methylbenzene) 39 4,4-(((((((((4-(tert-butyl)-1,2- 1.2 656.6 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(methylene))bis(methylbenzene) 40 13,13-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1-(p- 1.2 744.5 tolyl)-2,5,8,11-tetraoxatridecane) 41 16,16-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1-(p- 1.2 832.5 tolyl)-2,5,8,11,14-pentaoxahexadecane) 42 19,19-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1-(p- 1.2 920.6 tolyl)-2,5,8,11,14,17-hexaoxanonadecane) 43 25,25-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1-(4- 1.2 1180.8/ (tert-butyl)phenyl)-2,5,8,11,14,17,20,23- 599.5 octaoxapentacosane) 44 19,19-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1- 1.2 992.5 (naphthalen-2-yl)-2,5,8,11,14,17-hexaoxanonadecane) 45 (((((((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))bis(ethane- 1.2 596.5 2,1-diyl))bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(methylene))dibenzene 46 13,13-((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))bis(1- 1.2 772.6 phenyl-2,5,8,11-tetraoxatridecane) 47 19,19-((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))bis(1- 1.2 948.6 phenyl-2,5,8,11,14,17-hexaoxanonadecane) 48 25,25-((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))bis(1- 1.2 1124.7/ phenyl-2,5,8,11,14,17,20,23-octaoxapentacosane) 571.5 49 13,13-((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))bis(1-(4- 1.2 884.6 (tert-butyl)phenyl)-2,5,8,11-tetraoxatridecane) 50 25,25-((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))bis(1-(4- 1.2 1236.8/ (tert-butyl)phenyl)-2,5,8,11,14,17,20,23- 627.5 octaoxapentacosane) 51 1,2-bis(15-phenyl-2,5,8,11,14- 1.7 688.2 pentaoxapentadecyl)benzene 52 1,2-bis(27-phenyl-2,5,8,11,14,17,20,23,26- 1.7 1040.6 nonaoxaheptacosyl)benzene 53 1,2-bis(15-(4-(tert-butyl)phenyl)-2,5,8,11,14- 18 1.7 800.5 pentaoxapentadecyl)benzene 54 4,4-(((((((4-chloro-1,3-phenylene)bis(oxy))bis(ethane-2,1- 1.3 546.2 diyl))bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(methylene))bis(methylbenzene) 55 13,13-((4-chloro-1,3-phenylene)bis(oxy))bis(1-(p-tolyl)- 15 1.3 722.4 2,5,8,11-tetraoxatridecane) 56 1,5-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13- 1.2 710.4 yl)oxy)naphthalene 57 2,3-bis(2-(2-(benzyloxy)ethoxy)ethoxy)naphthalene 1.2 534.3 58 2,3-bis(2-(2-(2- 1.2 622.5 (benzyloxy)ethoxy)ethoxy)ethoxy)naphthalene 59 2,3-bis((1-phenyl-2,5,8,11-tetraoxatridecan-13- 6 1.2 710.4 yl)oxy)naphthalene 60 2,3-bis((1-phenyl-2,5,8,11,14-pentaoxahexadecan-16- 1.2 798.4 yl)oxy)naphthalene 61 2,3-bis((1-phenyl-2,5,8,11,14,17-hexaoxanonadecan-19- 1.2 886.4 yl)oxy)naphthalene 62 2,3-bis((1-phenyl-2,5,8,11,14,17,20,23- 1.2 1062.5/ octaoxapentacosan-25-yl)oxy)naphthalene 540.4 63 2,3-bis(2-(2-((4- 1.2 562.4 methylbenzyl)oxy)ethoxy)ethoxy)naphthalene 64 2,3-bis(2-(2-(2-((4- 1.2 650.4 methylbenzyl)oxy)ethoxy)ethoxy)ethoxy)naphthalene 65 2,3-bis((1-(p-tolyl)-2,5,8,11-tetraoxatridecan-13- 1.2 738.4 yl)oxy)naphthalene 66 2,3-bis((1-(p-tolyl)-2,5,8,11,14-pentaoxahexadecan-16- 1.2 826.4 yl)oxy)naphthalene 67 2,3-bis((1-(p-tolyl)-2,5,8,11,14,17-hexaoxanonadecan-19- 1.2 914.6 yl)oxy)naphthalene 68 13,13-((propane-2,2-diylbis(4,1- 1.2 806.4 phenylene))bis(oxy))bis(1-(p-tolyl)-2,5,8,11- tetraoxatridecane) 69 19,19-((propane-2,2-diylbis(4,1- 1.2 982.5/ phenylene))bis(oxy))bis(1-(p-tolyl)-2,5,8,11,14,17- 500.5 hexaoxanonadecane) 70 1,33-bis(4-(tert-butyl)phenyl)-15,19-dimethyl- 21 1.6 796.6 2,5,8,11,14,17,20,23,26,29,32-undecaoxatritriacontane 71 1,32-diphenyl-2,5,8,11,14,19,22,25,28,31- 22 1.8 640.5 decaoxadotriacontane 72 1,56-diphenyl- 1.8 992.6 2,5,8,11,14,17,20,23,26,31,34,37,40,43,46,49,52,55- octadecaoxahexapentacontane 73 bis(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) succinate 5 668.4 74 bis(1-(4-(tert-butyl)phenyl)-2,5,8,11-tetraoxatridecan-13- 5 780.5 yl) succinate 75 bis(1-(4-(tert-butyl)phenyl)-2,5,8,11,14,17,20,23- 5 1132.6/ octaoxapentacosan-25-yl) succinate 575.5 76 bis(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) glutarate 2 5 682.4 77 bis(1-phenyl-2,5,8,11,14,17,20,23-octaoxapentacosan- 5 1034.5/ 25-yl) glutarate 526.4 78 bis(1-(4-(tert-butyl)phenyl)-2,5,8,11-tetraoxatridecan-13- 5 794.5 yl) glutarate 79 bis(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) adipate 5 696.4 80 1,3,5-tris((1-(4-(tert-butyl)phenyl)-2,5,8,11- 1.2 1110.7 tetraoxatridecan-13-yl)oxy)benzene 81 1,3,5-tris(15-phenyl-2,5,8,11,14- 24 1.9 984.5 pentaoxapentadecyl)benzene 82 1,3,5-tris(27-phenyl-2,5,8,11,14,17,20,23,26- 25 1.9 765.6 nonaoxaheptacosyl)benzene 83 tris(1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) benzene- 3 5 1026.4 1,3,5-tricarboxylate 84 potassium 3,3-(((((1,2-phenylenebis(oxy))bis(ethane-2,1- 7 1.2.4 548.2 diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(propane-1- sulfonate) 85 potassium 3,3-(((((((1,2-phenylenebis(oxy))bis(ethane- 1.2.4 636.3 2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane- 2,1-diyl))bis(oxy))bis(propane-1-sulfonate) 86 potassium 1,1-(1,2-phenylenebis(oxy))bis(3,6,9,12- 8 1.2.4 724.3 tetraoxapentadecane-15-sulfonate) 87 potassium 1,1-(1,2- 1.2.4 900.3/ phenylenebis(oxy))bis(3,6,9,12,15,18- 459.2 hexaoxahenicosane-21-sulfonate) 88 potassium 1,1-(1,2- 1.2.4 1076.8/ phenylenebis(oxy))bis(3,6,9,12,15,18,21,24- 547.4 octaoxaheptacosane-27-sulfonate) 89 potassium 4,4-(((((1,2-phenylenebis(oxy))bis(ethane-2,1- 1.2.4 567.0 diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(butane-1- sulfonate) 90 potassium 1,1-(1,2-phenylenebis(oxy))bis(3,6,9,12- 1.2.4 752.3 tetraoxahexadecane-16-sulfonate) 91 potassium 1,1-(1,2- 1.2.4 928.3/ phenylenebis(oxy))bis(3,6,9,12,15,18-hexaoxadocosane- 473.3 22-sulfonate) 92 potassium 1,1-(1,2- 1.2.4 1104.4/ phenylenebis(oxy))bis(3,6,9,12,15,18,21,24- 561.2 octaoxaoctacosane-28-sulfonate) 93 potassium 3,3-((((((4-methyl-1,2- 1.2.4 562.3 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(propane-1- sulfonate) 94 potassium 1,1-((4-methyl-1,2- 9 1.2.4 738.1/ phenylene)bis(oxy))bis(3,6,9,12-tetraoxapentadecane- 378.3 15-sulfonate) 95 potassium 1,1-((4-methyl-1,2- 1.2.4 914.3/ phenylene)bis(oxy))bis(3,6,9,12,15,18- 466.3 hexaoxahenicosane-21-sulfonate) 96 potassium 1,1-((4-methyl-1,2- 1.2.4 1090.8/ phenylene)bis(oxy))bis(3,6,9,12,15,18,21,24- 554.4 octaoxaheptacosane-27-sulfonate) 97 potassium 4,4-((((((4-methyl-1,2- 1.2.4 590.0 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(butane-1- sulfonate) 98 potassium 1,1-((4-methyl-1,2- 10 1.2.4 766.4 phenylene)bis(oxy))bis(3,6,9,12-tetraoxahexadecane-16- sulfonate) 99 potassium 1,1-((4-methyl-1,2- 1.2.4 942.0/ phenylene)bis(oxy))bis(3,6,9,12,15,18- 480.3 hexaoxadocosane-22-sulfonate) 100 potassium 1,1-((4-methyl-1,2- 1.2.4 1118/ phenylene)bis(oxy))bis(3,6,9,12,15,18,21,24- 568 octaoxaoctacosane-28-sulfonate) 101 potassium 1,1-((((((4-methyl-1,2- 17 1.2.4 618.3 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(pentane-3- sulfonate) 102 potassium 4,4-((((((4-methyl-1,2- 16 1.2.4 742.3 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(1- phenylbutane-2-sulfonate) 103 potassium 1,1-((4-methyl-1,2-phenylene)bis(oxy))bis(28- 1.2.4 644.5 phenyl-3,6,9,12,15,18,21,24-octaoxaoctacosane-27- sulfonate) 104 potassium 3,3-((((((4-ethyl-1,3- 1.2.4 576.3 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(propane-1- sulfonate) 105 potassium 1,1-((4-ethyl-1,3- 1.2.4 752.3 phenylene)bis(oxy))bis(3,6,9,12-tetraoxapentadecane- 15-sulfonate) 106 potassium 1,1-((4-ethyl-1,3- 1.2.4 928.3/ phenylene)bis(oxy))bis(3,6,9,12,15,18- 473.3 hexaoxahenicosane-21-sulfonate) 107 potassium 1,1-((4-ethyl-1,3- 1.2.4 1104.4/ phenylene)bis(oxy))bis(3,6,9,12,15,18,21,24- 561.2 octaoxaheptacosane-27-sulfonate) 108 potassium 4,4-((((((4-ethyl-1,3- 1.2.4 604.3 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(butane-1- sulfonate) 109 potassium 1,1-((4-ethyl-1,3- 1.2.4 780.3 phenylene)bis(oxy))bis(3,6,9,12-tetraoxahexadecane-16- sulfonate) 110 potassium 1,1-((4-ethyl-1,3- 1.2.4 956.4/ phenylene)bis(oxy))bis(3,6,9,12,15,18- 487.3 hexaoxadocosane-22-sulfonate) 111 potassium 1,1-((4-ethyl-1,3- 1.2.4 1132.2/ phenylene)bis(oxy))bis(3,6,9,12,15,18,21,24- 575.1 octaoxaoctacosane-28-sulfonate) 112 potassium 3,3-((((((4-(tert-butyl)-1,2- 1.2.4 604.3 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(propane-1- sulfonate) 113 potassium 1,1-((4-(tert-butyl)-1,2- 1.2.4 780.4/ phenylene)bis(oxy))bis(3,6,9,12-tetraoxapentadecane- 399.4 15-sulfonate) 114 potassium 1,1-((4-(tert-butyl)-1,2- 1.2.4 956.5/ phenylene)bis(oxy))bis(3,6,9,12,15,18- 487.4 hexaoxahenicosane-21-sulfonate) 115 potassium 1,1-((4-(tert-butyl)-1,2- 1.2.4 1132.8/ phenylene)bis(oxy))bis(3,6,9,12,15,18,21,24- 575.4 octaoxaheptacosane-27-sulfonate) 116 potassium 4,4-((((((4-(tert-butyl)-1,2- 1.2.4 632.3 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(butane-1- sulfonate) 117 potassium 1,1-((4-(tert-butyl)-1,2- 1.2.4 808.5/ phenylene)bis(oxy))bis(3,6,9,12-tetraoxahexadecane-16- 413.4 sulfonate) 118 potassium 1,1-((4-(tert-butyl)-1,2- 1.2.4 984.5/ phenylene)bis(oxy))bis(3,6,9,12,15,18- 501.4 hexaoxadocosane-22-sulfonate) 119 potassium 1,1-((4-(tert-butyl)-1,2- 1.2.4 1160/ phenylene)bis(oxy))bis(3,6,9,12,15,18,21,24- 589.4 octaoxaoctacosane-28-sulfonate) 120 potassium 1,1-((3,5-di-tert-butyl-1,2- 1.2.4 836.4/ phenylene)bis(oxy))bis(3,6,9,12-tetraoxapentadecane- 427.4 15-sulfonate) 121 potassium 1,1-((3,5-di-tert-butyl-1,2- 1.2.4 1012.5/ phenylene)bis(oxy))bis(3,6,9,12,15,18- 515.4 hexaoxahenicosane-21-sulfonate) 122 potassium 1,1-((3,5-di-tert-butyl-1,2- 1.2.4 864.5/ phenylene)bis(oxy))bis(3,6,9,12-tetraoxahexadecane-16- 441.4 sulfonate) 123 potassium 3,3-((((((4-chloro-1,3- 1.2.4 582.2 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(propane-1- sulfonate) 124 potassium 1,1-((4-chloro-1,3- 1.2.4 758.2 phenylene)bis(oxy))bis(3,6,9,12-tetraoxapentadecane- 15-sulfonate) 125 potassium 4,4-((((((4-chloro-1,3- 1.2.4 610.2 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(butane-1- sulfonate) 126 potassium 1,1-((4-chloro-1,3- 1.2.4 786.3 phenylene)bis(oxy))bis(3,6,9,12-tetraoxahexadecane-16- sulfonate) 127 potassium 3,3-(((((naphthalene-2,3- 1.2.4 598.3 diylbis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(propane-1-sulfonate) 128 potassium 1,1-(naphthalene-2,3- 1.2.4 774.3/ diylbis(oxy))bis(3,6,9,12-tetraoxapentadecane-15- 396.3 sulfonate) 129 potassium 1,1-(naphthalene-2,3- 1.2.4 950.3/ diylbis(oxy))bis(3,6,9,12,15,18-hexaoxahenicosane-21- 484.3 sulfonate) 130 potassium 1,1-(naphthalene-2,3- 1.2.4 1126.8/ diylbis(oxy))bis(3,6,9,12,15,18,21,24- 572.4 octaoxaheptacosane-27-sulfonate) 131 potassium 4,4-(((((naphthalene-2,3- 1.2.4 626.3 diylbis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(butane-1-sulfonate) 132 potassium 1,1-(naphthalene-2,3- 1.2.4 802 diylbis(oxy))bis(3,6,9,12-tetraoxahexadecane-16- sulfonate) 133 potassium 1,1-(naphthalene-2,3- 1.2.4 978.3/ diylbis(oxy))bis(3,6,9,12,15,18-hexaoxadocosane-22- 498.4 sulfonate) 134 potassium 1,1-(naphthalene-2,3- 1.2.4 1154.6/ diylbis(oxy))bis(3,6,9,12,15,18,21,24-octaoxaoctacosane- 586.3 28-sulfonate) 135 1,1-(1,2-phenylenebis(oxy))bis(3,6,9,12,15,18,21,24- 4 1.2.4 1104.4/ octaoxaoctacosane-28-sulfonic acid) 561.2 136 25,25-((4-ethyl-1,3-phenylene)bis(oxy))bis(1-phenyl- 14 1.2 1104.4/ 2,5,8,11,14,17,20,23-octaoxapentacosane) 561.4 137 potassium 1,1-((4-methyl-1,2- 1.2.4 794.4/ phenylene)bis(oxy))bis(3,6,9,12-tetraoxaheptadecane- 406.3 15-sulfonate) 138 1,2-bis((1-(naphthalen-2-yl)-2,5,8,11-tetraoxatridecan-13- 1.2 760.4 yl)oxy)benzene 139 2,2-(((((((4-(tert-butyl)-1,2- 1.2 640.4 phenylene)bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(ethane-2,1- diyl))bis(oxy))bis(methylene))dinaphthalene 140 13,13-((4-(tert-butyl)-1,2-phenylene)bis(oxy))bis(1- 1.2 816.4 (naphthalen-2-yl)-2,5,8,11-tetraoxatridecane)