Nitrogen-containing Diesel Solidification Point Depressant Composition, and Preparation and Application Thereof

Abstract

The present invention relates to a nitrogen-containing diesel solidification point depressant composition, and preparation and application thereof. The nitrogen-containing diesel solidification point depressant composition includes the following components in percentage by weight: 10-40% of monoisopropanolamine; 10-40% of cyclohexane; 0-20% of polyethylene glycol; and 40-60% of N-tetradecyl methacrylamide-tetradecyl methacrylate. After the prepared diesel solidification point depressant composition is added to commercially available 0 #diesel, a solidification point and a cold filter plugging point of the diesel are respectively depressed by 21-25° C. and 9-13° C.

Claims

1. A nitrogen-containing diesel solidification point depressant composition, characterized by comprising the following components in percentage by weight: TABLE-US-00010 monoisopropanolamine 10-40%; cyclohexane 10-40%; polyethylene glycol 0-20%; and N-tetradecyl methacrylamide-tetradecyl methacrylate 40-60%.

2. The nitrogen-containing diesel solidification point depressant composition according to claim 1, characterized in that the N-tetradecyl methacrylamide-tetradecyl methacrylate is prepared by reacting N-tetradecyl methacrylamide with tetradecyl methacrylate in toluene serving as a solvent in the presence of benzoyl peroxide serving as an initiator.

3. The nitrogen-containing diesel solidification point depressant composition according to claim 2, characterized in that a molar ratio of the N-tetradecyl methacrylamide to the tetradecyl methacrylate is 1:10.

4. The nitrogen-containing diesel solidification point depressant composition according to claim 2, characterized in that the reaction temperature is 120° C., and the reaction time is 8 h.

5. The nitrogen-containing diesel solidification point depressant composition according to claim 1, characterized by comprising the following components in percentage by weight: TABLE-US-00011 monoisopropanolamine 20-40%; cyclohexane 10-30%; polyethylene glycol 5-20%; and N-tetradecyl methacrylamide-tetradecyl methacrylate 40-60%.

6. A preparation method of the nitrogen-containing diesel solidification point depressant composition according to claim 5, characterized by comprising the following steps: weighing stoichiometric N-tetradecyl methacrylamide-tetradecyl methacrylate, monoisopropanolamine, cyclohexane, and polyethylene glycol, stirring until uniform, and ultrasonically dispersing to yield a target product.

7. The preparation method of the nitrogen-containing diesel solidification point depressant composition according to claim 6, characterized in that the stirring temperature is 25-30° C., and the ultrasonic dispersion time is 10-20 min.

8. Application of the nitrogen-containing diesel solidification point depressant composition according to claim 5, characterized in that when used, the nitrogen-containing diesel solidification point depressant composition is added to and mixed with diesel until uniform, and the mixture is ultrasonically dispersed.

9. The application of the nitrogen-containing diesel solidification point depressant composition according to claim 8, characterized in that a mass ratio of the nitrogen-containing diesel solidification point depressant composition to the diesel is 1:(100-1000).

10. The application of the nitrogen-containing diesel solidification point depressant composition according to claim 8, characterized in that the mixing temperature is 30-45° C., and the ultrasonic dispersion time is 30 min.

11. Application of the nitrogen-containing diesel solidification point depressant composition according to claim 4, characterized in that when used, the nitrogen-containing diesel solidification point depressant composition is added to and mixed with diesel until uniform, and the mixture is ultrasonically dispersed.

12. Application of the nitrogen-containing diesel solidification point depressant composition according to claim 3, characterized in that when used, the nitrogen-containing diesel solidification point depressant composition is added to and mixed with diesel until uniform, and the mixture is ultrasonically dispersed.

13. Application of the nitrogen-containing diesel solidification point depressant composition according to claim 2, characterized in that when used, the nitrogen-containing diesel solidification point depressant composition is added to and mixed with diesel until uniform, and the mixture is ultrasonically dispersed.

14. Application of the nitrogen-containing diesel solidification point depressant composition according to claim 1, characterized in that when used, the nitrogen-containing diesel solidification point depressant composition is added to and mixed with diesel until uniform, and the mixture is ultrasonically dispersed.

15. A preparation method of the nitrogen-containing diesel solidification point depressant composition according to claim 4, characterized by comprising the following steps: weighing stoichiometric N-tetradecyl methacrylamide-tetradecyl methacrylate, monoisopropanolamine, cyclohexane, and polyethylene glycol, stirring until uniform, and ultrasonically dispersing to yield a target product.

16. A preparation method of the nitrogen-containing diesel solidification point depressant composition according to claim 3, characterized by comprising the following steps: weighing stoichiometric N-tetradecyl methacrylamide-tetradecyl methacrylate, monoisopropanolamine, cyclohexane, and polyethylene glycol, stirring until uniform, and ultrasonically dispersing to yield a target product.

17. A preparation method of the nitrogen-containing diesel solidification point depressant composition according to claim 2, characterized by comprising the following steps: weighing stoichiometric N-tetradecyl methacrylamide-tetradecyl methacrylate, monoisopropanolamine, cyclohexane, and polyethylene glycol, stirring until uniform, and ultrasonically dispersing to yield a target product.

18. A preparation method of the nitrogen-containing diesel solidification point depressant composition according to claim 1, characterized by comprising the following steps: weighing stoichiometric N-tetradecyl methacrylamide-tetradecyl methacrylate, monoisopropanolamine, cyclohexane, and polyethylene glycol, stirring until uniform, and ultrasonically dispersing to yield a target product.

Description

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0018] The present invention will be described in detail below with reference to specific examples. The examples are implemented on the basis of the technical solutions of the present invention, detailed implementation modes and specific operation processes are given, but the scope of protection of the present invention is not limited to the following examples.

[0019] In the present invention, cold filter plugging points are determined in accordance with SH/T0248-2006 Diesel and Domestic Heating fuels—Determination of cold filter plugging point, and solidification points are determined in accordance with GB510-83 Petroleum Products—Determination of Solidification Point.

[0020] Raw materials used in the present invention:

TABLE-US-00003 Sinopec 0# diesel purchased from Shanghai Songjiang Petrol Station Company Limited; monoisopropanolamine purchased from Titan Science Co., Ltd.; (analytically pure) cyclohexane purchased from Titan Science Co., Ltd.; (analytically pure) polyethylene glycol (200) purchased from Titan Science Co., Ltd.; (analytically pure) tetradecyl methacrylate purchased from Titan Science Co., Ltd.; and polymethacrylate purchased from Haiyan Fine Chemical Co., solidification point Ltd. depressant T1804

[0021] N-tetradecyl methacrylamide is prepared by acylation, that is, an acid-binding agent and tetradecylamine are dissolved by stirring in N,N-dimethylformamide serving as a solvent, methacryloyl chloride is added to and reacts with the solution for 2 h, and the reaction product is washed with water and dried to yield N-tetradecyl methacrylamide. N-tetradecyl methacrylamide-tetradecyl methacrylate is prepared by reacting N-tetradecyl methacrylamide with tetradecyl methacrylate in a monomer molar ratio of 1:10 in toluene serving as a solvent in the presence of benzoyl peroxide serving as an initiator at 120° C. for 8 h.

[0022] Unless otherwise specified, other raw materials or processing techniques are conventional commercially available raw materials or conventional processing techniques in the art.

Example 1

[0023] A diesel solidification point depressant composition that was prepared by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate with monoisopropanolamine, cyclohexane, and polyethylene glycol (200) included the following components in percentage by mass:

TABLE-US-00004 monoisopropanolamine 10%; cyclohexane 20%; polyethylene glycol (200) 10%; and N-tetradecyl methacrylamide-tetradecyl methacrylate 60%.

[0024] The above diesel solidification point depressant composition was applied to the depression of a solidification point of diesel, and a mass ratio of the diesel solidification point depressant composition to the diesel was preferably 1:200. The diesel solidification point depressant composition was added to 60 g of Songjiang 0 #diesel in a mass ratio of 0.1%, and the mixture was stirred at 50° C. until uniform and ultrasonically dispersed for 15 min to obtain diesel containing the diesel solidification point depressant composition.

[0025] By tests, a solidification point and a cold filter plugging point of the above commercially available 0 #diesel containing the above diesel solidification point depressant composition that was prepared in Example 1 were respectively depressed by 25° C. and 13° C.

Example 2

[0026] A diesel solidification point depressant composition that was prepared by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate with monoisopropanolamine, cyclohexane, and polyethylene glycol (200) included the following components in percentage by mass:

TABLE-US-00005 monoisopropanolamine 20%; cyclohexane 20%; polyethylene glycol (200) 5%; and N-tetradecyl methacrylamide-tetradecyl methacrylate 55%.

[0027] The above diesel solidification point depressant composition was applied to the depression of a solidification point of diesel, and a mass ratio of the diesel solidification point depressant composition to the diesel was preferably 1:200. The diesel solidification point depressant composition was added to 60 g of Songjiang 0 #diesel in a mass ratio of 0.1%, and the mixture was stirred at 50° C. until uniform and ultrasonically dispersed for 15 min to obtain diesel containing the diesel solidification point depressant composition.

[0028] By tests, a solidification point and a cold filter plugging point of the above commercially available 0 #diesel containing the above diesel solidification point depressant composition that was prepared in Example 2 were respectively depressed by 24° C. and 12° C.

Example 3

[0029] A diesel solidification point depressant composition that was prepared by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate with monoisopropanolamine, cyclohexane, and polyethylene glycol (200) included the following components in percentage by mass:

TABLE-US-00006 monoisopropanolamine 30%; cyclohexane 10%; polyethylene glycol (200) 20%; and N-tetradecyl methacrylamide-tetradecyl methacrylate 40%.

[0030] The above diesel solidification point depressant composition was applied to the depression of a solidification point of diesel, and a mass ratio of the diesel solidification point depressant composition to the diesel was preferably 1:200. The diesel solidification point depressant composition was added to 60 g of Songjiang 0 #diesel in a mass ratio of 0.1%, and the mixture was stirred at 50° C. until uniform and ultrasonically dispersed for 15 min to obtain diesel containing the diesel solidification point depressant composition.

[0031] By tests, a solidification point and a cold filter plugging point of the above commercially available 0 #diesel containing the above diesel solidification point depressant composition that was prepared in Example 3 were respectively depressed by 23° C. and 11° C.

Example 4

[0032] A diesel solidification point depressant composition that was prepared by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate with monoisopropanolamine, cyclohexane, and polyethylene glycol (200) included the following components in percentage by mass:

TABLE-US-00007 monoisopropanolamine 10%; cyclohexane 30%; polyethylene glycol (200) 10%; and N-tetradecyl methacrylamide-tetradecyl methacrylate 50%.

[0033] The above diesel solidification point depressant composition was applied to the depression of a solidification point of diesel, and a mass ratio of the diesel solidification point depressant composition to the diesel was preferably 1:200. The diesel solidification point depressant composition was added to 60 g of Songjiang 0 #diesel in a mass ratio of 0.1%, and the mixture was stirred at 50° C. until uniform and ultrasonically dispersed for 15 min to obtain diesel containing the diesel solidification point depressant composition.

[0034] By tests, a solidification point and a cold filter plugging point of the above commercially available 0 #diesel containing the above diesel solidification point depressant composition that was prepared in Example 4 were respectively depressed by 22° C. and 10° C.

Example 5

[0035] A diesel solidification point depressant composition that was prepared by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate with monoisopropanolamine, cyclohexane, and polyethylene glycol (200) included the following components in percentage by mass:

TABLE-US-00008 monoisopropanolamine 20%; cyclohexane 30%; polyethylene glycol (200) 10%; and N-tetradecyl methacrylamide-tetradecyl methacrylate 40%.

[0036] The above diesel solidification point depressant composition was applied to the depression of a solidification point of diesel, and a mass ratio of the diesel solidification point depressant composition to the diesel was preferably 1:200. The diesel solidification point depressant composition was added to 60 g of Songjiang 0 #diesel in a mass ratio of 0.1%, and the mixture was stirred at 50° C. until uniform and ultrasonically dispersed for 15 min to obtain diesel containing the diesel solidification point depressant composition.

[0037] By tests, a solidification point and a cold filter plugging point of the above commercially available 0 #diesel containing the above diesel solidification point depressant composition that was prepared in Example 5 were respectively depressed by 21° C. and 10° C.

Example 6

[0038] A diesel solidification point depressant composition that was prepared by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate with monoisopropanolamine, cyclohexane, and polyethylene glycol (200) included the following components in percentage by mass:

TABLE-US-00009 monoisopropanolamine 20%; cyclohexane 20%; polyethylene glycol (200) 20%; and N-tetradecyl methacrylamide-tetradecylmethacrylate 40%.

[0039] The above diesel solidification point depressant composition was applied to the depression of a solidification point of diesel, and a mass ratio of the diesel solidification point depressant composition to the diesel was preferably 1:200. The diesel solidification point depressant composition was added to 60 g of Songjiang 0 #diesel in a mass ratio of 0.1%, and the mixture was stirred at 50° C. until uniform and ultrasonically dispersed for 15 min to obtain diesel containing the diesel solidification point depressant composition.

[0040] By tests, a solidification point and a cold filter plugging point of the above commercially available 0 #diesel containing the above diesel solidification point depressant composition that was prepared in Example 5 were respectively depressed by 21° C. and 9° C.

[0041] Contrast 1

[0042] The N-tetradecyl methacrylamide-tetradecyl methacrylate solidification point depressant used in Example 1 was not mixed with monoisopropanolamine, cyclohexane, and polyethylene glycol (200), and directly added to 60 g of Songjiang 0 #diesel in a mass ratio of 0.1%, and the mixture was stirred at 50° C. until uniform and ultrasonically dispersed for 15 min. By tests, a solidification point and a cold filter plugging point of the Songjiang 0 #diesel added with the solidification point depressant were respectively depressed by 19° C. and 7° C.

[0043] By comparing the above examples with Contrast 1, it can be seen that the solubility and the dispersibility of the diesel solidification point depressant composition that was prepared by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate with monoisopropanolamine, cyclohexane, and polyethylene glycol (200) in diesel are improved by the solvents, a solidification point depression effect of the solidification point depressant composition is improved by the synergistic action of the solidification point depressants, and the low-temperature fluidity of diesel is improved.

[0044] Contrast 2

[0045] A preferred commercially available polymethacrylate solidification point depressant T1804 was applied to the depression of a solidification point of diesel, and a mass ratio of the solidification point depressant to the diesel was preferably 1:200. The diesel solidification point depressant was added to 60 g of Songjiang 0 #diesel in a mass ratio of 0.1%, and the mixture was stirred at 50° C. until uniform and ultrasonically dispersed for 15 min to obtain diesel containing the diesel solidification point depressant.

[0046] By tests, a solidification point and a cold filter plugging point of the above commercially available 0 #diesel containing the above diesel solidification point depressant that was prepared in Contrast 2 were respectively depressed by 19° C. and 6° C.

[0047] By comparing the above examples with Application Example 2, it can be seen that the diesel solidification point depressant composition prepared by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate with monoisopropanolamine, cyclohexane, and polyethylene glycol (200) has higher sensitivity to diesel, and achieves a better solidification point depression effect.

[0048] Contrast 3

[0049] This contrast was basically the same as Example 1, and a difference was that monoisopropanolamine was replaced with an equal mass of N-tetradecyl methacrylamide-tetradecyl methacrylate.

[0050] By tests, a solidification point and a cold filter plugging point of the above commercially available 0 #diesel containing the above diesel solidification point depressant composition that was prepared in Contrast 3 were respectively depressed by 20° C. and 9° C.

[0051] By comparing the above examples with Application Example 1, it can be seen that the diesel solidification point depressant composition prepared by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate with monoisopropanolamine, cyclohexane, and polyethylene glycol (200) has higher sensitivity to diesel, and achieves a better solidification point depression effect.

[0052] Contrast 4

[0053] This contrast was basically the same as Example 1, and a difference was that polyethylene glycol was replaced with an equal mass of cyclohexane.

[0054] By tests, a solidification point and a cold filter plugging point of the above commercially available 0 #diesel containing the above diesel solidification point depressant composition that was prepared in Contrast 4 were respectively depressed by 19° C. and 8° C.

[0055] By comparing the above examples with Application Example 1, it can be seen that the diesel solidification point depressant composition prepared by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate with monoisopropanolamine, cyclohexane, and polyethylene glycol (200) has higher sensitivity to diesel, and achieves a better solidification point depression effect.

[0056] Contrast 5

[0057] This contrast was basically the same as Example 1, and a difference was that cyclohexane was replaced with an equal mass of polyethylene glycol.

[0058] By tests, a solidification point and a cold filter plugging point of the above commercially available 0 #diesel containing the above diesel solidification point depressant composition that was prepared in Contrast 5 were respectively depressed by 20° C. and 7° C.

[0059] By comparing the above examples with Application Example 1, it can be seen that the diesel solidification point depressant composition prepared by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate with monoisopropanolamine, cyclohexane, and polyethylene glycol (200) has higher sensitivity to diesel, and achieves a better solidification point depression effect.

[0060] The above description of the examples is for those of ordinary skill in the art to understand and implement the present invention. It is obvious that those skilled in the art may easily make various modifications to these examples, and apply the general principles described here to other examples without involving any creative effort. Therefore, the present invention is not limited to the above examples, and improvements and modifications made by those skilled in the art based on the disclosure of the present invention without departing from the scope of the present invention shall fall within the scope of protection of the present invention.