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United States Patent [191 [11] Patent Number: 4,639,533 Finnan [45] Date of Patent: Jan

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United States Patent [191 [11] Patent Number: 4,639,533 Finnan [45] Date of Patent: Jan United States Patent [191 [11] Patent Number: 4,639,533 Finnan [45] Date of Patent: Jan. 27, 1987 [54] ALPHA TOCOPHEROL PROCESS [56] References Cited U.S. PATENT DOCUMENTS [75] Inventon Jeffrey L- Finn?n, Southgate, Mich- 4,191,692 3/1980 Grafen et a1. ..................... .. 549/411 4,208,334 6/1980 Fitton et a1. 549/411 [73] Assignee: BASF Corporation, Wyandotte, 4,217,2 8 5 8 / 1980 Y 05 h’mo et a 1. ................... .. 549 / 411 Mich. Primary Examiner-Nicky Chan Attorney, Agent, or Firm-Rupert B. Hurley, Jr.; Joseph [21] Appl. No.: 403,085 D. Michaels [57] ABSTRACT . _ D,1-a1pha-toc0phero1 can be prepared by reacting [22] Flled' Jul’ 29’ 1982 trimethylhydroquinone and a phytyl derivative such as phytol or isophytol in the presence of a Lewis acid, a [51] Int. Cl.4 .......................................... .. C07D 311/72 strong acid and an amine. [52] US. Cl. ............................. .. [58] Field of Search .............................. .. 549/411, 410 19 Claims, No Drawings 4,639,533 1 2 halogen-leaving groups are preferably chlorine and ALPHA TOCOPHEROL PROCESS bromine. The preferred lower alkylsulfonyloxy leaving group is mesyloxy. The preferred arylsulfonyloxy leav BACKGROUND OF THE INVENTION ing group is tosyloxy. The preferred lower alkanoyloxy 1. Field of the Invention group is acetoxy. The preferred lower alkoxy leaving This invention relates to an improved process for groups are n-butoxy, methoxy, isobutoxy, and ethoxy. manufacturing d,l-alpha-tocopherol. As used throughout the speci?cation, the term “halo 2. Description of the Prior Art gen” includes all four halogens such as bromine, chlo The preparation of d,l-alpha-tocopherol by the con rine, ?uorine and iodine. densation of trimethylhydroquinone and a phytol deriv The term “lower alkyl” includes saturated aliphatic ative in the presence of an inert solvent and acid con hydrocarbon groups containing 1 to 7 carbon atoms densing agents is well known in the art. The acid cata such as methyl, ethyl, propyl, isopropyl, isobutyl, etc. lyst can be either or both a Lewis acid such as zinc The term “lower alkoxy” includes lower alkoxy chloride or a strong inorganic acid such as hydrochloric groups containing from 1 to 7 carbon atoms such as acid, sodium bisulfate or para-toluenesulfonic acid. In 15 methoxy, ethoxy, n-butoxy, isobutoxy, etc. addition, it is known from US. Pat. No. 4,191,692 to The term “lower alkanoyl” includes lower alkanoyl pre-react isophytol with a small amount of ammonia or groups containing from 1 to 7 carbon atoms, preferably an amine prior to reaction with trimethylhydroquinone. from 2 to 7 carbon atoms such as acetyl, propionyl, etc. The use of zinc chloride, an inert solvent and gaseous The term “aryl” denotes monocyclic aromatic hydro hydrochloric acid in the process of producing d,l-alpha 20 carbons such as phenyl and polycyclic aromatic hydro tocopherol is disclosed by Karrer in US. Pat. Nos. carbons such as naphthyl which can be unsubstituted or 2,411,967; 2,411,968; and 2,411,969. Greenbaum et al in substituted in one or more positions with a lower alkyl US. Pat. No. 3,708,505 also disclose the use of a combi or nitro group. nation of a Lewis acid and a strong acid in a process for the preparation of d,l-alpha-tocopherol. 25 Speci?c examples of phytol derivatives useful in the Improved process catalysts or combinations thereof preparation of the alpha-tocopherols of the invention are also disclosed in Us. Pat. Nos. 4,208,334; 2,723,278; include phytol, isophytol, phytadiene, phytol chloride, phytol bromide, phytol acetate and phytol methyl 3,789.086; 3,459,773; 3,444,213; and 4,217,285. ether. The preferred phytol is isophytol. SUMMARY OF THE INVENTION The inert organic solvents which can be employed as It has been unexpectedly discovered that by includ a reaction medium in the process of the invention are ing a small amount of an amine in the reaction mixture those aromatic and aliphatic hydrocarbon solvents hav for the preparation of d,l-alpha-tocopherol that an im ing a boiling point below the boiling points of the reac proved product is obtained, speci?cally a product hav tants and the desired product. Preferred solvents in ing greater purity. Additionally, the percent yield is also 35 clude aliphatic hydrocarbon solvents having about 5 to increased. In the process of the invention, trimethylhy about 12 carbon atoms. Representative aromatic hydro droquinone and an inert organic solvent are charged carbon solvents include xylene, benzene, and toluene. into a reaction vessel together with a combination of at Miscellaneous inert organic solvents also can be used. least one aprotic Lewis acid, at least one protonic Representative aliphatic hydrocarbon solvents include strong organic acid, and at least one amine. A phytol pentane, hexane, heptane, octane, nonane, decane, un derivative such as isophytol is then_ slowly added to the decane, and dodecane. Preferably, n-heptane is utilized. reaction mixture and when addition has been com Other inert organic solvents can be used such as an pleted, the reaction mass is re?uxed for a suf?cient time aliphatic ether such as isopropyl ether.‘ to produce d,l-alpha-tocopherol. Optionally, acetic an The aprotic acids useful as catalysts in the process of hydride can be added to produce d,l-alpha-tocopherol 45 the invention include boron tri?uoride, boron tribro acetate. It is a particular advantage of the present pro mide, aluminum chloride, aluminum bromide, zinc chlo cess that the synthesis is essentially a one-step process ride, boron tri?uodiphosphoric acid complex, and the which produces a higher yield as well as a higher qual like. The preferred Lewis acid is zinc chloride. ity d,l-alpha-tocopherol. ' Protonic strong acid catalysts useful in the process of 50 the invention include hydrogen chloride gas, sulfuric DESCRIPTION OF THE PREFERRED acid, hydrochloric acid, nitric acid, para-toluene sul EMBODIMENTS fonic acid, sodium bisulfate, and mixtures thereof. Pref The phytyl derivative useful as a reactant in the pro erably, strong acids such as sulfuric acid, para-toluene cess of the invention has the formulas: sulfonic acid, and sodium bisulfate are used. Especially 55 preferred is anhydrous hydrogen chloride gas present in CH3 CH3 CH3 CH3 (1) the reaction mixture in an amount sufficient to saturate said reaction mixture. CH2: CH_C—(CH2)3- CH—(CH2)3-CH—(CH2)3- CPI-CH3 The amines which are useful in the process of the i invention can be arylaliphatic amines having about 7 to about 24 carbon atoms or aliphatic and cycloaliphatic and amines having about 7 to about 24 carbon atoms, prefer CH3 CH3 CH3 CH3 (II) ably about 18 to about 22 carbon atoms, in the aliphatic chain. The amines can be primary, secondary or tertiary amines. The alkyl primary monoamines which can have 65 straight or branched chains are preferred. Representa wherein X is a leaving group. Useful leaving groups tive examples of useful alkyl amines are tridecylamine, include hydroxy, halogen, lower alkylsulfonyloxy, aryl l-docosanamine, l-eicosanamine, pentadecylmethyla sulfonyloxy, lower alkoxy, and lower alkanoyloxy. The mine, octadecyldimethylamine, dioctyldecylamine, and 4,639,533 3 4 octadecylamine. A representative example of a useful cycloaliphatic amine is cyclohexylamine. A representa EXAMPLE 1 tive example of a useful arylaliphatic amine is benzyl (Control, forming no part of this invention) amine. Amines useful in the process of the invention can In this example, and in Example 2, the process of the be further substituted with groups such as hydroxy, prior art is shown in which isophytol is mixed and pre lower alkoxy, or lower alkylamino groups. reacted with an amine prior to reaction with trimethyl The general reaction of the phytol derivative with hydroquinone. trimethylhydroquinone is known in the art as indicated Crude isophytol (97.5 percent by weight purity) in by the procedures provided'in U.S. Pat. No. 3,708,505, the amount of 100 parts by weight was mixed with 0.3 incorporated herein by reference. The process of the part by weight of tridecylamine and thereafter heated at invention is performed by charging trimethylhydroqui 80° C. for two hours. After cooling, the product of the none into a reaction ?ask together with the Lewis acid, isophytylamine reaction was used directly in the con strong acid, amine, and inert organic solvent. The com densation reaction with trimethylhydroquinone as de bination is then heated at a temperature of 50° C. to scribed below. about 150° C. and the phytol derivative is added slowly The amine-isophytol reaction product was added to said combination of ingredients over a period of dropwise to a mixture of trimethylhydroquinone (76.1 about 2 to about 6 hours. The reaction mass is then grams, 0.495 mole), zinc chloride 95 percent by weight further heated at about 50° C. to about 150° C. for about aqueous (20.7 grams, 0.150 mole) in technical grade 6 to about 24 hours. When the reaction is completed, the 20 n-heptane (380 ml). The mixture was heated to constant mass can be puri?ed by distillation if so desired. re?ux with a continuous hydrogen chloride sparge and One of the useful and unexpected results of using the the amine-isophytol reaction product (181 ml, 0.50 amine in combination with the Lewis acid and strong mole) was added dropwise over a period of 90 minutes. acid in accordance with the process of the invention is After completion of the addition of the amine-treated that the d,l-alpha-tocopherol produced has a purity of 25 isophytol, the hydrogen chloride sparge was continued about 90 to about 95 percent by weight, which meets for an additional 15 minutes, and ?ve minutes later the feed grade standards.
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