Fuel and related compositions – Liquid fuels – Organic nitrogen compound containing
Reexamination Certificate
2001-07-06
2004-09-28
Toomer, Cephia D. (Department: 1714)
Fuel and related compositions
Liquid fuels
Organic nitrogen compound containing
C508S542000, C564S336000
Reexamination Certificate
active
06797021
ABSTRACT:
The present invention relates to a process of preparation of novel Mannich Bases from hydrogenated and distilled Cashew Nut Shell Liquid (CNSL) for use as additive in liquid hydrocarbon fuels for removing and protecting build up of deposits on carburetor surfaces and intake valve systems in a gasoline powered engine system.
BACKGROUND OF THE INVENTION
Typical middle distillate hydrocarbon fuels, boiling in the gasoline range and used in spark-ignition internal combustion (IC) engines often contain components, which possess low volatility or solubility in the fuels. In practice such components tend to form deposits in the fuel carburetion system where fuel vaporization occurs. Deposit accumulations on carburetor throttle body & plates and intake valves lead to progressively poorer engine performance such as improper or rough idling of the engine, excessive consumption of fuel and the increased level of hydrocarbons and partially burned fuel components in the exhaust gas. Chemicals, which prevent or eliminate deposits in carburetor and intake valve systems, contribute significantly not only to automotive efficiency and economy of operation but also to minimizing pollution of the environment.
Deposits thus accumulated may be removed periodically by physical cleaning during engine overhaul or tune-up. A more preferred option to the deposit problem requires no interruption of engine usage and this is usually accomplished in practice by inclusion of a chemical composition known as carburetor detergent additive in the gasoline fuel.
There is a growing need for a chemical or chemical composition possessing detergency properties such that carburetor deposits may be completely eliminated. The importance of this need is now emphasized by the widespread awareness of pollution problems and the desire to minimize the emission of pollutants from automotive exhaust systems.
As a thumb rule, carburetor detergent additives must be soluble in the hydrocarbon fuel composition and possess a suitable balance of lyophilize and hydrophilic properties. Addition of carburetor detergents usually result in alleviating the deposits problem, however, they may exhibit hydrophilic surface-active properties to such a degree that water suspension (haze) and emulsion formation may occur. Therefore, there is a need for a suitable carburetor detergent additive for automotive systems, which should be effective in removing and preventing deposits on carburetor surfaces while exhibiting no undesirable effects upon other properties of the gasoline.
Newer generation designs for automotive power units make provision for recycle of gases which contain some partially oxidized hydrocarbons having a tendency to form deposits at or near the intake valves. Accordingly, suitable detergent additives for use in automotive fuels must be capable of keeping intake valves clean. There is, therefore, also a need for a suitable intake valve detergent additive for automotive systems effective in removing and preventing deposits in the intake system while exhibiting no undesirable effects upon other properties of the hydrocarbon fuel. Ideally, a suitable detergent additive for use in gasoline range hydrocarbon fuel will provide and maintain a high degree of cleanliness in both carburetor and intake systems.
Polar grouping suitable for inclusion in oil-soluble surface-active agents is the basic amine grouping and a non-polar grouping for such agents is the alkylaryl group usually provided by alkylation of phenols. Such polar and non-polar groups may be conveniently brought together in one molecular by the well-known Mannich condensation reaction involving an alkyl phenol, a low molecular weight aldehyde and an amine.
The alkyl phenol used in the process is hydrogenated and distilled Cashew Nut Shell Liquid (popularly known as CNSL) obtained after the hydrogenation of naturally occurring, biodegradable, vegetable based Cashew Nut Shell Liquid. CNSL occurs as a reddish brown viscous liquid in the soft honeycomb structure of the shell of cashewnut. CNSL, extracted with low boiling petroleum ether, contains about 90% anacardic acid and about 10% cardol. CNSL, on distillation, gives the pale yellow phenolic derivatives, which are a mixture of biodegradable unsaturated m-alkylphenols, including cardanol. Catalytic hydrogenation of these phenols gives a white waxy material, predominantly rich in tetrahydroanacardol which is also known as hydrogenated CNSL.
CNSL and its derivatives have been known for producing high temperature phenolic resins and friction elements, as exemplified in U.S. Pat. Nos. 4,395,498 and 5,218,038. Friction lining production from CNSL is also reported in U.S. Pat. No. 5,433,774. Likewise, it is also known to form different types of friction materials, mainly for use in brake lining system of automobiles and coating resins from CNSL.
Mannich condensation reactions usually proceed with the formation of high molecular weight products, by linear growth due to the use of mono-substituted phenols and an amine groups. Excess aldehyde may also react with amine groups to form imines or hydroxymethylamines.
Accordingly, the properties of such polymeric compositions have principally been utilized in heavier fuels such as heating and furnace oils, as described in US. Pat. No. 2,962,442, and in lubricating oils, as disclosed in U.S. Pat. Nos. 3,036,003 and 3,539,633. None of these uses involves a sensitive carburetion system as is found in the gasoline-powered spark-ignition internal combustion system.
Mannich condensation products have often been employed as stabilizers, or antioxidants, as well as dispersants, or detergents, in heavy hydrocarbon stocks. Use in lighter hydrocarbon stocks such as gasolines, has been disclosed in U.S. Pat. Nos. 3,269,810 and 3,649,229. U.S. Pat. No. 3,235,484 (Now U.S. Pat. No. Re. 26,330) describes the addition of certain disclosed compositions to refinery hydrocarbon fuel stocks for the purpose of inhibiting the accumulation of carbonaceous deposits in refinery cracking units. The primary inhibitors disclosed are mixtures of amides, imides and amine salts formed by reacting an ethylene polyamine with hydrocarbon substituted succinic acids or anhydride, whose hydrocarbon substituaent has at least about 50 carbon atoms. As an adjunct for such primary carbonaceous deposit inhibitors there is disclosed in said patent Mannich condensation products formed by reacting (1) alkylphenol, (2) an amine and (3) formaldehyde in the ratio of one mole alkylphenol and from 0.1-10 mole each of formaldehyde and amine reactant.
U.S. Pat. No. 3,368,972 describes dispersant-detergent additive for lubricating oils as high molecular weight Mannich condensation products from (1) high molecular weight alkyl-substituted hydroxyaromatic compounds whose alkyl-substituent has a molecular weight in the range of 600-3000, (2) a compound containing at least one HN< group and (3) an aldehyde in the respective molar ratio of 1.0:0.1-10:1.0-10.
The high molecular weight Mannich condensation products of either U.S. Pat. No. 3,235,484 or U.S. Pat. No. 3,368,972 have a drawback in their large-scale preparation and in their extended service used as lubricant addition agents used under high temperature conditions such as encountered in diesel engines. In the large-scale or plant preparation of such high molecular weight condensation products, especially in light mineral oil solvents, the resulting oil concentrate solution of the condensation product either has or develops during storage a haze which is believed to be caused by undissolved or borderline soluble by-products which not only are not substantially incapable of removal by filtration but also severely resurrect product filtration rate. When used in diesel engine crankcase lubricant oils and subject to high temperature in service use, piston ring groove carbonaceous deposits and skirt varnish tend to build up sufficiently rapidly and prevent desirable long in-service use of such lubricant oils.
A combination of diamine and higher polyamine Mannich condensation products useful
Bhatnagar Akhilesh
Gupta Anurag Ateet
Misra A. K.
Prasad Rameshwar
Puri Suresh Kumar
Indian Oil Corporation Limited
Needle & Rosenberg P.C.
Toomer Cephia D.
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