Alkyl diols for crude oil treatment

1. A method for reducing paraffin or wax deposition in crude oil during processing, storage, or transportation, the method comprising contacting the crude oil with a composition in an amount effective to reduce paraffin or wax deposition, wherein the composition comprises a compound of Formula (I):

wherein

n is an integer from 0 to 3;

m is an integer from 0 to 20;

R 1 is hydrogen, C 1 -C 20 substituted or unsubstituted alkyl, or C 1 to C 20 substituted or unsubstituted alkoxy;

R 2 is hydrogen, or C 1 -C 20 substituted or unsubstituted alkyl; and

R 3 is hydrogen, or C 1 -C 20 substituted or unsubstituted alkyl.

2. The method of claim 1 , wherein n is 0.

3. The method of claim 2 , wherein m is 0.

4. The method of claim 3 , wherein R 1 is C 6 to C 20 unsubstituted alkyl.

5. The method of claim 3 , wherein R 1 is C 6 to C 20 unsubstituted alkoxy.

6. The method of claim 4 , wherein R 2 is hydrogen or C 1 to C 3 alkyl.

7. The method of claim 1 , wherein m is from 1 to 20.

8. The method of claim 7 , wherein R 1 is hydrogen or C 1 to C 15 unsubstituted alkyl.

9. The method of claim 8 , wherein R 1 is hydrogen or methyl.

10. The method of claim 9 , wherein R 2 is hydrogen or C 1 to C 15 alkyl.

11. The method of claim 1 , wherein the compound of Formula I is 1,2-dihydroxydodecane, 1,2-dihydroxynonane, 1,2-dihdroxyundecane, 1,2-dihydroxydodecane, 1,2-dihydroxytridecane, 1,2-dihydroxypentadecane, 1,2-dihydroxyheptadecane, 1,2-dihydroxyoctadecane, 1,10-dihydroxydecane, 1,2-dihydroxyhexane, 3-dodecyloxy-1,2-dihydroxypropane, 2-ethyl-1,3-hexanediol, 1,2-dihydroxyoctane, 1,2-dihydroxydecane, 1,2-dihydroxytetradecane, 1,2-dihydroxyhexadecane, 1,2-dihydroxyocatdecane, 1,2-dihydroxyeicosane, 1,2-dihydroxy-10-methylundecane, 2,3-dihydroxynonane, 2,3-dihydroxydecane, 2,3-dihydroxyundecane, 2,3-dihydroxytridecane, 2,3-dihydroxytetradecane, 2,3-dihydroxyheptadecane, 2,3-dihydroxyoctadecane, 2,3-dihydroxydodecane, 1,3-dihydroxyhexane, 1,3-dihydroxyheptane, 1,3-dihydroxyoctane, 1,3-dihydroxynonane; 1,3-dihydroxydecane, 1,3-dihydroxyundecane, 1,3-dihydroxydodecane, 1,3-dihydroxytridecane, 1,3-dihydroxytetradecane, 1,3-dihydroxypentadecane, 1,3-dihydroxyhexadecane, 1,3-dihydroxyheptadecane, 1,3-dihydroxyoctadecane, 1,4-dihydroxyheptane, 1,4-dihydroxyoctane, 1,4-dihydroxynonane, 1,4-dihydroxydecane, 1 ,4-dihydroxyundecane, 1,4-dihydroxydodecane, 1,4-dihydroxytridecane, 1,4-dihydroxytetradecane, 1,4-dihydroxypentadecane, 1,4-dihydroxyhexadecane, 1,4-dihydroxyheptadecane, 1,4-dihydroxyoctadecane, 1,5-dihydroxyoctane, 1,5-dihydroxynonane, 1,5-dihydroxydecane, 1,5-dihydroxyundecane, 1,5-dihydroxydodecane, 1,5-dihydroxytridecane, 1,5-dihydroxytetradecane, 1,5-dihydroxypentadecane, 1,5-dihydroxyhexadecane, 1,5-dihydroxyheptadecane, 1,5-dihydroxyoctadecane, 1,6-dihydroxyhexane, 1,6-dihydroxynonane, 1,6-dihydroxydecane, 1,6-dihydroxyundecane, 1,6-dihydroxydodecane, 1,6-dihydroxytridecane, 1,6-dihydroxytetradecane, 1,6-dihydroxypentadecane, 1,6-dihydroxyhexadecane, 1,6-dihydroxyheptadecane, 1,6-dihydroxyoctadecane, 1,7-dihydroxydecane, 1,7-dihydroxyundecane, 1,7-dihydroxydodecane, 1,7-dihydroxytridecane, 1,7-dihydroxytetradecane, 1,7-dihydroxypentadecane, 1,7-dihydroxyhexadecane, 1,7-dihydroxyheptadecane, 1,7-dihydroxyoctadecane, 1,7-dihydroxyheptane, 1,8-dihydroxyoctane, 1,8-dihydroxyundecane, 1,8-dihydroxydodecane, 1,8-dihydroxytridecane, 1,8-dihydroxytetradecane, 1,8-dihydroxypentadecane, 1,8-dihydroxyhexadecane, 1,8-dihydroxyheptadecane, 1,8-dihydroxyoctadecane, 1,9-dihydroxynonane, 1,9-dihydroxydodecane, 1,9-dihydroxytridecane, 1,9-dihydroxytetradecane, 1,9-dihydroxypentadecane, 1,9-dihydroxyhexadecane, 1,9-dihydroxyheptadecane, 1,9-dihydroxyoctadecane, 1,10-dihydroxytridecane, 1,10-dihydroxytetradecane, 1,10-dihydroxypentadecane, 1,10-dihydroxyhexadecane, 1,10-dihydroxyheptadecane, 1,10-dihydroxyoctadecane, 1,11-dihydroxytetradecane, 1,11-dihydroxypentadecane, 1,11-dihydroxyhexadecane, 1,11-dihydroxyheptadecane, 1,11 -dihydroxyoctadecane, 1,12-dihydroxypentadecane, 1,12-dihydroxyhexadecane, 1,12-dihydroxyheptadecane, 1,12-dihydroxyoctadecane, 1,13-dihydroxyhexadecane, 1,13-dihydroxyheptadecane, 1,13-dihydroxyoctadecane, 1,14-dihydroxyheptadecane, 1,14-dihydroxyoctadecane, 1,15-dihydroxyoctadecane, 1,10-dihydroxydecane, 1,11-dihydroxyundecane, 1,12-dihydroxydodecane, 11-methyl-1,12-dihydroxydodecane, 1,14-dihydroxytetradecane, 1,15-dihydroxypentadecane, 1,16-dihydroxyhexadecane, 1,18-dihydroxyoctadecane, 1,20-dihydroxyeicosane, 1-methyl-1,3-dihydroxyhexane, 1-methyl-1,3-dihydroxyheptane, 1-methyl-1,3-dihydroxyoctane, 1-methyl-1,3-dihydroxynonane, 1-methyl-1,3-dihydroxydecane, 1-methyl-1,3-dihydroxyundecane, 1-methyl-1,3-dihydroxydodecane, 1-methyl-1,3-dihydroxytridecane, 1-methyl-1,3-dihydroxytetradecane, 1-methyl-1,3-dihydroxypentadecane, 1-methyl-1,3-dihydroxyhexadecane, 1-methyl-1,3-dihydroxyheptadecane, 1-methyl-1,3-dihydroxyoctadecane, 2-ethyl-1,3-dihydroxyhexane, 1,6-dihydroxyhexane, 1,7-dihydroxyheptane, 1,8-dihydroxyoctane, 1,9-dihydroxynonane, 1,10-dihydroxydecane, 1,11-dihydroxyundecane, 1,12-dihydroxydodecane, 1,13-dihydroxytridecane, 1,14-dihydroxytetradecane, 1,15-dihydroxypentadecane, 1,16-dihydroxyhexadecane, 1,17-dihydroxyheptadecane, 1,18-dihydroxyoctadecane, or a combination thereof.

12. The method of claim 11 , wherein the compounds of Formula I is 1,2-dihydroxydodecane, 1,10-dihydroxydecane, 3-dodecyloxy-1,2-dihydroxypropane, or a combination thereof.

13. The method of claim 1 , wherein the crude oil has a wax appearance temperature of about 30° C. to about 50° C.

14. The method of claim 1 , wherein the composition further comprises a surfactant, a solvent, or a combination thereof.

15. The method of claim 14 , wherein the solvent comprises xylene, light naphtha, kerosene, liquid alkanes, diesel, lubricating oils, bitumen, or a combination thereof.

16. The method of claim 1 , wherein the composition contains from about 65 wt. % to about 85 wt. % of a compound of Formula I.

17. The method of claim 1 , wherein the composition is contacted with the crude oil at a concentration from about 1 ppm to about 10,000 ppm based on the total weight of the crude oil.

18. The method of claim 17 , wherein the composition is contacted with the crude oil at a concentration from about 5 ppm to about 5,000 ppm.

19. The method of claim 18 , wherein the composition is contacted to the crude oil at a concentration from about 10 ppm to about 1,000 ppm.

20. A method for reducing paraffin or wax deposition in crude oil during processing, storage, or transportation, the method comprising contacting the crude oil with a composition in an amount effective to reduce paraffin or wax deposition, wherein the composition comprises a compound of Formula (I) and a polymeric paraffin control agent, the compound of Formula (I) having the structure:

wherein

n is an integer from 0 to 3;

m is an integer from 0 to 20;

R 1 is hydrogen, C 1 -C 20 substituted or unsubstituted alkyl, or C 1 to C 20 substituted or unsubstituted alkoxy;

R 2 is hydrogen, or C 1 -C 20 substituted or unsubstituted alkyl; and

R 3 is hydrogen, or C 1 -C 20 substituted or unsubstituted alky; and

wherein the polymeric paraffin control agent comprises ethylene and small olefin copolymers, ethylene-vinyl copolymers, ethylene-acrylonitrile copolymers, methacrylate ester copolymers, maleic-olefinic ester copolymers, maleic-olefinic amide copolymers, alkylphenol-formaldehyde copolymers, polyethyleneimine copolymers, or a combination thereof.