Cyclic ortho ester fuel additive

Patent metadata

Field	Value
Publication number	US-9802912-B2
Application number	US-201414786647-A
Country	US
Kind code	B2
Filing date	Apr 24, 2014
Priority date	Apr 25, 2013
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

Abstract

The invention relates to liquid hydrocarbons containing cyclic ortho esters as dehydrating dehydrating icing inhibitors and to methods of using the compounds. The liquid hydrocarbons include fuels such aviation fuels, lubricants, hydraulic fluids and hydrocarbon solvents.

First claim

The invention claimed is:

1. A liquid hydrocarbon comprising a dehydrating icing inhibitor selected from Formula I and Formula II, salts thereof or mixtures thereof;

where:
R 1 and R 3 are independently selectable and are selected from a C 1 to C 6 substituted or non-substituted, branched or straight chain, alkyl or ether;
R 2 and R 4 are independently selectable and are selected from a C 1 to C 7 substituted or non-substituted, straight or branched chain, alkyl;
Y is independently selectable and is a substituted or non-substituted alkyl;
y is an integer of 1 to 3;
z is an integer of 2 to 6; and,

wherein liquid hydrocarbon is a hydrocarbon fuel selected from an aviation fuel, gasoline, diesel and heating oil, a lubricant or a hydraulic fluid.

2. A liquid hydrocarbon according to claim 1 , wherein the liquid hydrocarbon is a hydrocarbon fuel, lubricant, hydraulic fluid or hydrocarbon solvent.

3. A liquid hydrocarbon according to claim 2 , wherein the hydrocarbon fuel is an aviation fuel, gasoline, diesel or heating oil.

4. A liquid hydrocarbon according to claim 1 , wherein R 1 and R 3 are independently selected from CH 3 —, CH 3 CH 2 —, CH 3 O(CH 2 ) a —, where a is an integer of 1 to 5, and an alkylene glycol or polyalkylene glycol containing 1 to 6 carbon atoms.

5. A liquid hydrocarbon according to claim 4 , wherein R 1 or R 3 are CH 3 CH 2 —.

6. A liquid hydrocarbon according to claim 1 , wherein R 2 and R 4 are independently selected from —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH 2 CH(CH 3 ) 2 and —CH 2 C(CH 3 ) 3 .

7. A liquid hydrocarbon according to claim 1 , wherein R 3 and R 4 are independently selected and are methyl or ethyl.

8. A liquid hydrocarbon according to claim 1 , wherein y is 2.

9. A liquid hydrocarbon according to claim 1 , wherein Y is independently selected from —CH 2 — and —CH(CH 3 )—.

10. A liquid hydrocarbon comprising a dehydrating icing inhibitor selected from Formula I and Formula II, salts thereof or mixtures thereof;

where:
R 1 and R 3 are independently selectable and are selected from a C 1 to C 6 substituted or non-substituted, branched or straight chain, alkyl or ether;
R 2 and R 4 are independently selectable and are selected from a C 1 to C 7 substituted or non-substituted, straight or branched chain, alkyl;
Y is independently selectable and is a substituted or non-substituted alkyl;
y is an integer of 1 to 3;
z is an integer of 2 to 6; where the dehydrating icing inhibitor has a Formula III or Formula IV or a salt thereof;

wherein R 5 and R 7 are hydrogen; and R 6 and R 8 are methyl, and wherein R 6 and R 8 may be cis or trans relative to each other.

11. A liquid hydrocarbon according to claim 1 , comprising 0.01 to 2% by volume of the dehydrating icing inhibitor.

12. A liquid hydrocarbon according to claim 1 , wherein the compound is formed from a 1,3-dioxolan-2-ylium salt.

13. A method of inhibiting ice crystal formation in a liquid hydrocarbon comprising mixing the liquid hydrocarbon with a compound selected from Formula I and formula II, or mixtures thereof:

where:
R 1 and R 3 are independently selectable and are selected from a C 1 to C 6 substituted or non-substituted, branched or straight chain, alkyl or ether;
R 2 and R 4 are independently selectable and are selected from a C i to C 7 substituted or non-substituted, straight or branched chain, alkyl;
Y is independently selectable and is a substituted or non-substituted alkyl;
y is an integer of 1 to 3;
z is an integer of 2 to 6.

14. A method according to claim 13 , wherein 0.01 to 2% by volume of the dehydrating icing inhibitor(s) is added to the liquid hydrocarbon.

15. A method according to claim 13 , wherein the liquid hydrocarbon is a hydrocarbon fuel, lubricant, or hydrocarbon solvent.

16. A method according to claim 15 , wherein the hydrocarbon fuel is an aviation fuel, gasoline, diesel of heating oil.

17. A method according to claim 13 , wherein R 1 and R 3 are independently selected from CH 3 —, CH 3 CH 2 —, —CH 3 O(CH 2 ) a —, where a is an integer of 1 to 5, and an alkylene glycol or polyalkylene glycol containing 1 to 6 carbon atoms.

18. A method according to claim 17 , wherein R 1 or R 3 are CH 3 CH 2 —.

19. A method according to claim 13 , wherein R 2 and R 4 are independently selected from —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH 2 CH(CH 3 ) 2 and —CH 2 C(CH 3 ) 3 .

20. A method according to claim 13 , wherein R 3 and R 4 are independently selected and are methyl or ethyl.

21. A method according to claim 13 , wherein y is 2.

22. A method according to claim 13 , wherein Y is independently selected from —CH 2 — and —CH(CH 3 )—.

23. A method of inhibiting ice crystal formation in a liquid hydrocarbon comprising mixing the liquid hydrocarbon with a compound selected from Formula I and formula II, or mixtures thereof:

where:
R 1 and R 3 are independently selectable and are selected from a C 1 to C 6 substituted or non-substituted, branched or straight chain, alkyl or ether;
R 2 and R 4 are independently selectable and are selected from a C 1 to C 7 substituted or non-substituted, straight or branched chain, alkyl;
Y is independently selectable and is a substituted or non-substituted alkyl;
y is an integer of 1 to 3;
z is an integer of 2 to 6; wherein in dehydrating icing inhibitor has a Formula III or Formula IV or a salt thereof;

wherein R 5 and R 7 are hydrogen; and R 6 and R 8 are methyl, and wherein R 6 and R 8 may be cis or trans relative to each other.

24. A method of inhibiting ice crystal formation in a liquid hydrocarbon comprising mixing the liquid hydrocarbon with a 1,3-dioxolan-2-ylium salt.

25. A compound of Formula IV or a salt thereof;

where:
R 3 is independently selectable and is selected from a C 1 to C 6 substituted or non-substituted,
branched or straight chain, alkyl or ether;

R 4 is independently selectable and is selected from a C 1 to C 7 substituted or non-substituted,
straight or branched chain, alkyl;

z is an integer of 2 to 6;
R 5 and R 7 are hydrogen;
and R 6 and R 8 are methyl, and wherein R 6 and R 8 may be cis or trans relative to each other as a dehydrating icing inhibitor.

Assignees

• Airbus Operations Ltd

Inventors

• Lam Joseph K-W
• Ratcliffe Norman
• De Lacy Costello Benjamin
• Repetto Sonia
• Costello James
• Parmenter David

Classifications

• C10M105/18

  Ethers, e.g. epoxides · CPC title

• C10G33/04 Primary

  with chemical means · CPC title

• C10G75/00

  Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general (C10G7/10, C10G9/16 take precedence) · CPC title

• C10G29/22

  containing oxygen as the only hetero atom · CPC title

• C10L2290/24

  Mixing, stirring of fuel components · CPC title