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United States Patent to 11 4,011,057 Sayers 45) Mar

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United States Patent to 11 4,011,057 Sayers 45) Mar United States Patent to 11 4,011,057 Sayers 45) Mar. 8, 1977 54 HINDERED PHENOL ANTIOXIDANT 2,202,877 6, 1940 Stevens et al. ........................ 4.4/78 COMPOSTION CONTAINING AN AMNO 2,459,597 - 1/1949 Stillson et al...................... 44f78 X COMPOUND 2,521,425 9/1950 Thompson ............................. 44f75 . 2,672,408 3/1954 Bonner ........ a- - - - - - - a a a a - - 44f72 (75 Inventor: George Alvin Sayers, Penns Grove, 2,793,943 5/1957 Moore ...... a- a - a a - - - a a - a - 44f72 N.J. 2,908,558 10/1959 Brimer...... - - - - - - 44f75 73) Assignee: E. I. Du Pont de Nemours and 3,166,509 171965 Ecke ...................................... 44,178 Company, Wilmington, Del. Primary Examiner-Daniel E. Wyman 22 Filed: Apr. 16, 1974 Assistant Examiner-Mrs. Y. Harris-Smith (21) Appl. No.:& was 461,391 Attorney, Agent, or Firm-James A. Costello 52 U.S. Cl. ....................................... 44/52; 4.4/72; 57 ABSTRACT 51l Int. Cl”...........................................44/75; coL22 252/403 An improved antioxidant composition. comprising hin 58) Field of Search ........... 44/52, 72, 75; 252/403; dered phenol antioxidant wherein the improvement 260/624 comprises, in combination with the hindered phenol, 8 from about 1% to 10%, by total weight, of at least one 56 References Cited amino compound having a pKb of from 0.3 to 8.0. UNITED STATES PATENTS 1,748,507 111930 Brooks .................................. 44/52 12 Claims, No Drawings 401 1,057 1. 2 Ammonia has a pKa of 4.75 while substituted ammo HINDERED PHENOL ANTIOxIDANT nia compounds such as methylamine (pK 3.37), ethyl COMPOSTON CONTAINING AN AMNO amine (pK, 3.27), isopropylamine (pK 3.37), ethanol COMPOUND amine (pK 4.56) are slightly stronger bases than am monia. Guanidine, a very strong organic base has a pK, BACKGROUND OF THE INVENTION or 0.3. Generally, for an amino compound to have a 1. Field of the Invention pK of 8 or less the substituent on the amino nitrogen This invention concerns antioxidant compositions, will be attached to the nitrogen atom via an aliphatic or especially antioxidant compositions for gasoline. The cycloaliphatic carbon atom, even though such carbon compositions comprise primarily hindered phenols in O combination with a small amount of an amine. The atom can also have aromatic substituents. Thus, ben compositions are characterized by reduced crystalliza zylamine has a pKa of 4.70 while aniline (outside the tion temperature, lighter color, and enhanced antioxi invention) has a pKa of 9.30. The preferred amino dant efficiency, over compositions that are similar ex compound will have a pKa of from about 3 to about 5. cept that they do not have the amine present. 15 The preferred antioxidant compositions of this inven 2. Description of the Prior Art tion contain from about 3 to 6% of the amino com Phenolic antioxidants are preferred for modern gaso pound(s), based on total weight of the antioxidant. The lines which have relatively low olefin content, because amino compound(s) have been found, surprisingly, to of their low cost and increasing relative antioxidant exercise synergistic antioxidant qualities with the hin efficiency with decreasing olefin content of the gaso 20 dered phenols, even in the relatively small amounts of line. Principal commercially employed antioxidants are 10% or less that are contemplated herein. the alkylated phenols, N,N'-dialkylated para The hindered phenol portion of the antioxidant of phenylenediamines and N-alkylated para-amino this invention can be single phenols or mixtures of phenols. phenols. The term “hindered phenol' as employed Alkylated phenol antioxidants usually contain a ter 25 herein, depending on the context, includes mixtures of tiary alkyl group ortho to the hydroxyl group. Included hindered phenols. The preferred hindered phenol is are 2,6-ditert-butyl-4-methylphenol, 2,4-dimethyl-6- tertiary butylated phenol. Especially preferred is ter tert-butylphenol, 2,4-ditert-butylphenol, 2,6-ditert tiary butylated phenol containing at least about 60% of butylphenol, 2-tert.-butylphenol, 4,4'-methylene 2,4-ditert-butylphenol. The most preferred amino bis(2,6-ditert-butylphenol), 4,4'-thiobis(2,6-ditert.- 30 compound is 1,2-diaminopropane. butylphenol) and the like. Such phenols containing the The term hydrocarbyl as employed herein includes bulky tertiary alkyl group at one or both orthopositions aliphatic hydrocarbyl (such as alkyl and alkenyl), cy are often referred to as hindered phenols. cloaliphatic hydrocarbyl (such as cyclopentyl, cyclo Most hindered phenols are solids at ambient temper hexyl and cycloheptyl), and araliphatic hydrocarbyl atures or they are liquids which crystallize when ex 35 (such as benzyl, tolylyl, xylylyl and 2-phenylethyl). The posed to low temperatures such as are encountered total number of carbon atoms is preferably 1 to 20 during the winter months in colder climates. It is gener carbons. ally preferred that a gasoline additive be liquid for ease This invention also concerns a gasoline fuel composi of addition and lower costs. Using solvents to provide 40 tion containing the novel antioxidants of this invention. hindered phenol as concentrated solutions is not com pletely satisfactory since the phenols are still subject to The concentration of the antioxidants will usually be crystallization from solution at low temperatures. Fur from about 1 to 10 lbs. per 1,000 barrels. ther, the increased cost of preparing, handling and DETAELS OF THE INVENTION shipping solutions makes this unattractive. There is, 45 Hindered phenols are usually prepared by alkylation therefore, a need for a practical liquid hindered phenol of a phenol or an alkylphenol containing at least one antioxidant composition which is resistant to solidifica free ortho position with a 1,1-dialkylmonoolefin. More tion (crystallization) at relatively low temperatures. usually the 1,1-dialkylmonoolefin is isobutylene so that Also desirable would be for such composition to have the tertiary alkyl group introduced is the tertiary butyl good light color and good efficiency. 50 group. Methods of alkylating phenols with olefins are SUMMARY OF THE INVENTION well known in the art and the present invention is not This invention concerns an improved antioxidant dependent upon any particular method of preparation composition comprising hindered phenol antioxidant of the hindered phenols. wherein the improvement comprises, in combination 55 Most contemplated hindered phenol antioxidants are with the hindered phenol, from about 1% to 10%, by not single compounds but are mixtures of alkylated weight of the antioxidant composition, of at least one phenols. For example, when phenol is alkylated with amino compound having a pKa of from about 0.3 to isobutylene, the reaction mass generally contains two 8.0. or more of the following: 2-tert-butylphenol, 4-tert.- The amino compound can be ammonia or a hydro 60 butylphenol, 2,4-ditert-butylphenol, 2,6-ditert-butyl carbyl-substituted ammonia compound. The substi phenol and 2,4,6-tritert.-butylphenol. The composition tuted ammonia will contain up to about 49 carbon of the mixed hindered phenol depends, of course, upon atoms. The common characteristic of the contemplated the particular catalyst used, the ratio of isobutylene to amino compounds is that they are nitrogen bases of pK, the phenol used, and the reaction conditions such as 0.3 to 8.0. The smaller the pK the greater the base 65 time and temperature. strength of the amino compound, the term pK mean Most of the tertiary butylated phenols are solids at ing-log K where K is the basic dissociation constant ordinary temperatures as indicated by the melting of the amino compound in water at 25 C. points given below. 401 1,057 4 propyl)ethylamine, N,N-bis(3-hydroxypropyl)propyla nine, N-(2-hydroxypropyl)ethylamine, N,N-bis(2- Meltin 8. Point hydroxypropyl)methylamine, N,N-bis(triethoxylated)- Hindered Phenol O C. butylamine, N,N-bis(tetraethoxylated)oleylamine, 4-tert-butylphenol 98.4 2,4-ditert-butylphenol 56.5 N,N-bis(pentaethoxylated)oleylamine and the like. 2,6-ditert-butylphenol 39 iii. Cyclic amines of the formula, R-NY, where R is a 2,4,6-tritert-butylphenol 131 hydrogen or hydrocarbyl, y is a divalent connecting group such as -(CH2)-, where m = 4 to 6, -CHC H-NHCHCH-, -CHCH-O-CHCH-. Rep Commercial mixtures of tertiary butylphenols ordi O resentative examples are piperidine, N-methylpiperi narily have crystallization temperatures of from about dine, N-ethylpiperidine, piperazine, N-methylpipera 0 to about 30° C. By crystallization temperature is zine, N-ethylpiperazine, morpholine, N-methylmor meant the highest temperature at which a seeded sam pholine, N-ethyl morpholine and the like. ple of the phenol will develop crystals. The crystalliza iv. Amino compounds of the formula, tion temperature is therefore a measure of the ten 15 dency of the composition to solidify or form crystals. NR Since such antioxidant compositions are very often I exposed to temperatures lower than the crystallization RN-C-NR, temperature range of 0 to 30' C., particularly during the winter months in the coldersections of the northern 20 wherein R represents hydrogen or hydrocarbyl. This and southern hemispheres, partially or completely so class includes guanidine and alkylated guanidines such lidified compositions often result. as monomethylguanidine, dimethylguanidine, trimeth The hydrocarbyl-substituted ammonia compounds yiguanidine, tetramethylguanidine, pentamethylguani that are useful together with the antioxidants noted dine and the
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