Process for manufacturing gasoline additives of ester-free...

Details Process for manufacturing gasoline additives of ester-free... Process for manufacturing gasoline additives of ester-free...

2002-01-28

2003-09-30

Kumar, Shailendra (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C564S136000, C564S159000, C564S215000, C044S418000, C044S419000

Reexamination Certificate

active

06627775

ABSTRACT:

FIELD OF INVENTION
This invention relates to a method of a gasoline additive producing and more particularly a process for manufacturing gasoline additives of ester-free polyoxyalkylene-amide which is advantageous for decreasing intake valve deposits, decreasing octane requirements, controlling internal combustion chamber deposits and improving fuel efficiency.
BACKGROUND OF THE INVENTION
Many additives are known to be added in gasoline in order to prevent or reduce deposit formation. Recent related prior art is cited below:
Polyoxyalkylene amide:
U.S. Pat. No. 5,352,251 (Oct. 4, 1994) to Shell Oil Company, “Ring polyoxyalkylene amide as gasoline additives”.
U.S. Pat. No. 5,693,107 (Dec. 2, 1997) to Shell Oil Company, “Hydantoin polyoxyalkylene amide as gasoline additives”.
U.S. Pat. No. 5,492,546 (Feb. 20, 1996) to Shell Oil Company, “Fuel composition”.
U.S. Pat. No. 5,507,843 (1996) to Shell Oil Company, “Fuel composition”.
U.S. Pat. No. 5,489,315 (1996) to of Shell Oil Company, “Hydantoin polyether polyol as gasoline additives”.
U.S. Pat. No. 5,458,661 (1995) to Shell Oil Company, “Fuel composition”.
U.S. Pat. No. 5,458,660 (1995) to Shell Oil Company, “Fuel composition”.
Polyoxyalkylene amines:
U.S. Pat. No. 5,057,122 (Oct. 15, 1991) to Mobil Oil Company, “A dilsocyanate derivatives composition as fuel additives and lubricants”.
Other documents include U.S. Pat. No. 4,604,103 (1986) to Chevron, U.S. Pat. No. 5,112,364 (1992) to BASF, U.S. Pat. Nos. 5,286,266 & 5,286,267 (1994) to Texaco, U.S. Pat. Nos. 5,286,478 (1993) & 5,203,879 (1993) & 4,810,261 (1989) & 4,747,851 (1988) to Texaco.
Polyoxyalkylene amine carbamates:
U.S. Pat. No. 5,321,460 (1994) to Chevron, “Linear propylene oxide of polyoxyalkylene amine carbamates as a fuel composition”.
And also U.S. Pat. No. 5,322,539 (1994), 5,321,460 (1994), 5,192,335 (1993) to Chevron, U.S. Pat. No. 423,321 (1980) to Chevron, U.S. Pat. No. 5,103,041 (1992) to British Petroleum U.S. Pat. No. 4,568,358 (1986) to Chevron.
Others
U.S. Pat. No. 5,296,003 (Mar. 22, 1994) to Chevron, U.S. Pat. No. 5,298.039 (Mar. 29, 1994) to BASF, disclosing a gasoline fuel composition comprised a nitro-detergent and polyester as a carried oil compound, wherein polyester compound starter is dialkyl phenol.
U.S. Pat. No. 5,246,006 (1993) to Exxon and 5,089,029 (1992) to Kao Corporation, regarding acrylonitrile reaction to form a Guerbet alkyletheramino-alchohol by addition process and reducing process.
However, the above prior arts never mention the formation of a byproduct, polyoxyalkylene amide-ester as follows:
Which may reduce the performance of the other gasoline additives in lessening intake valve deposits or increasing the octane requirement.
SUMMARY OF THE INVENTION
The object of the present invention is to provide a process for manufacturing gasoline additives of ester-free polyoxyalkylene amides which are advantageous for decreasing intake valve deposits, octane requirements, controlling combustion chamber deposits and improving fuel efficiency.
The present invention is directed to manufacturing gasoline additives of ester-free polyoxyalkylene amide from a three-step process, as in FIG.
1
:
A. Amidation of low-molecular-weight polyoxyalkylene amine with ethyl acetate to form the corresponding amides.
B. Alkoxylation of the amide with 1,2-epoxybutane to form polyoxyalkylene amide and unavoidable byproducts as below:
C. Selective hydrolysis of the above mixtures to remove the amide-ester byproducts and recover the desired amide alkoxylates.
The essential analytical method is to use FT-infrared to identify the presence of the byproducts, hence the ester-free amides should be free of the following indicative 1735 cm
−1
absorption:
Those ester-amide byproducts are proven to be harmful to the engine. Therefore, in step(c), the removal of the esters is important to manufacture the effective gasoline additives. The hydrolysis must be selective to remove only the ester byproducts but remaining the following desired amide alkyoxylate with the indicative infra-red absorption at 1650 cm
−1
.
The selective hydrolysis process is one of essential part of this invention. For example, the amidation and alkoxylation to made diethylenetriamine-triamide-butoxylate (DETA triamide-BO) and its contaminated esters should be subjected to the selective hydrolysis step to remove the ester functional group. The process required the treatment of the product mixtures with 8 to 12 wt % HCl, preferably 10% at 90 to 100° C. under the refluxing condition. The process is carefully monitored by analyzing the disappearance of ester C═O Absorption peak (1735 cm
−1
) by IR. The ester functionalities are removed and a polyalkylene amide or amine-amide is generated. The desired composition is further analyzed by a gel permeation chromatography showing a narrow molecular weight distribution.
The tests of intake valve coking simulator (IVCS), and thermal decomposition test and octane requirement reduction (ORR) showed excellent results for the ester-free products.


REFERENCES:
patent: 6312481 (2001-11-01), Lin et al.
patent: 6454818 (2002-09-01), Lin et al.

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