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United States Patent 0 Patented Nov 2,723,278 United States Patent 0 Patented Nov. 8, 1955 1 2 was cooled to room temperature and ?ltered, then washed 2,723,278 twice with water, and the solvent was removed by dis PREPARATION OF ALPHA-TOCOPHEROL tillation under vacuum. The residue, a-dl-tocopherol, was Joseph Donald Surmatis, Pompton Plains, and Joseph a light-colored, yellow syrup. Weber, Paterson, N. J ., assignors to Holfmann-La Roche To this residual syrup was added 800 cc. of acetic Inc., Roche Park, N. J., a corporation of New Jersey anhydride, and the reaction mixture was re?uxed for 3 No Drawing. Application January 25, 1954, hours. The excess acetic anhydride was removed under Serial No. 406,079 a vacuum of about 20 mm. and the product was then distilled under a high vacuum to produce an almost water 4 Claims. (Cl. 260—345.5) 10 white syrup of dl-a-tocopheryl acetate. This invention relates to an improved process for Example 2 making e-tocopherol. More particularly, it relates to such a process wherein phytyl chloride is condensed with 5.0 kg. of isophytol (about 95% pure) was stirred trimethylhydroquinone in the presence of a boron tri with 15 liters of technical grade 37% aqueous hydro ?uoride catalyst. In the practice of the invention on a 15 chloric acid at room temperature for about 2 hours. The large scale, the process thereof has made it possible to pro acid layer was separated, extracted with petroleum ether duce in excellent yield a vitamin E product characterized and the extract added to the oil layer. The combined by its stable, light color and its comparative lack of odor oils were washed twice with water and dried over cal and taste. cium chloride to yield dry phytyl chloride. A preferred form of catalyst is a boron tri?uoride 20 2.705 kg. of trimethylhydroquinone (technical grade, etherate, and it is desirable to use this in such propor about 95 % pure), 20 liters of petroleum ether and 250 tion as will present a boron tri?uoride content of from cc. of a 40% by weight solution of boron tri?uoride in about 0.03 mol (about 2.0 g.) to about 0.15 mol (about diethyl ether were charged to a kettle. The mixture was 10.2 g.) of boron tri?uoride per mol (about 315.0 g.) heated to about 60°-70° C., and the total amount of of phytyl chloride. A preferred condition is the use of 25 phytyl chloride produced as described in the preceding a boron tri?uoride di(lower alkyl)etherate, and particu paragraph was added over a 2 hour period, keeping the larly boron tri?uoride diethyl etherate, in such amount temperature at about 60°-70° C.; all operations being as to provide about 0.1 mol (about 6.8 g.) of contained conducted under a carbon dioxide atmosphere. After BF3 per mol of phytyl chloride. Boron tri?uoride di addition of the phytyl chloride, the temperature was ethyl etherate is sometimes represented by the formula 30 maintained at about 60°-70° C. for 12 hours under an BFs- (C2H5)2O, but it should be understood that the in atmosphere of carbon dioxide. The reaction mixture was vention is not limited to any speci?ed formula for this then washed twice with water and the solvent ?ashed off or for any other boron tri?uoride complex, since the in vacuo to leave a light-colored syrup of dl-u-tocopherol. active catalytic material is boron tri?uoride itself, the The dl-a-tocopherol produced as described above was etherates being however preferred forms of boron tri 35 re?uxed for 5 hours with 4 liters of acetic anhydride. ?uoride catalyst. The phytyl chloride is advantageously The excess acetic anhydride was then distilled off under a used in approximately equimolar proportion to the tri water vacuum, and ?nally the residue was ?ash distilled methylhydroquinone. The condensation is desirably ef in high vacuo. The dl-a-tocopheryl acetate thus produced fected at a temperature in the range of from about 50° C. was a clear viscous liquid having a very light yellow color to about 85° C., a temperature of from about 60° C. to 40 and having little or no odor, sp. gr. 20°/ 15 °=0.958, and about 70° C. being preferred. "D20: 1.4968. A comprehensive embodiment of the invention is il We claim: lustrated by a process which has been practiced on a com 1. A process of making a-tocopherol which comprises mercial scale in the manufacture of a-tocopheryl acetate, condensing phytyl chloride with trimethylhydroquinone and which comprises a process of reacting isophytol with in the presence of a boron tri?uoride catalyst. commercial concentrated aqueous hydrochloric acid to 45 2. A process of making a-tocopherol which comprises produce phytyl chloride, reacting the latter with trimeth condensing phytyl chloride with trimethylhydroquinone ylhydroquinone in the presence of boron tri?uoride di in the presence of a boron tri?uoride etherate providing ethyl etherate to form dl-u-tocopherol, and acetylating the from about 0.03 mol to about 0.15 mol of contained latter to produce dl-a-tocopheryl acetate. boron tri?uoride per mol of phytyl chloride. The invention is further disclosed in the following ex 50 3. A process of making a-tocopherol which comprises amples, which are illustrative but not limitative thereof: condensing phytyl chloride with trimethylhydroquinone, in the presence of a boron tri?uoride di( lower alkyl)ether Exandzple 1 ate providing from about 0.03 mol to about 0.15 mol 1.0 kg. of isophytol (about 95% pure) was placed in of contained boron tri?uoride per mol of phytyl chloride, a ?ask together with 3.0 liters of 37% aqueous hydro 55 and at a temperature in the range of from about 50° C. chloric acid. The mixture was stirred for 2 hours at room to about 85° C. temperature. The oil layer was separated, the aqueous 4. A process of making u-tocopherol which comprises acid layer was extracted with 500 cc. of petroleum ether, condensing phytyl chloride with trimethylhydroquinone and the extract was added to the oil layer. The combined in approximately equimolar proportion, in the presence oils were washed twice, each time with 500 cc. of water, of an amount of boron tri?uoride diethyl etherate suf? and dried overnight over 200 g. of anhydrous calcium cient to provide about 0.1 mol of boron tri?uoride per chloride to yield dry phytyl chloride. mol of phytyl chloride, and at a temperature in the range In a ?ask were placed 513 g. of trimethylhydroquinone of from about 60° C. to about 70° C. (about 95 % pure) and 3 liters of petroleum ether. The slurry was heated up to 80° C. while stirring. Then 25 65 References Cited in the ?le of this patent cc. of a 45% by weight solution of boron tri?uoride in UNITED STATES PATENTS diethyl ether were added. The total amount of phytyl 2,249,054 Smith et al. __________ __ July 15, 1941 chloride produced as described in the preceding para 2,345,605 John et al _____________ __ Apr. 4, 1944 graph was added dropwise at 80°—85° C. in the course 2,411,942 Smith et al ____________ __ Dec. 3, 1946 of about 4 hours. The stirring was continued for an 70 2,411,967 Karrer ______________ __ Dec. 3, 1946 additional 2 hours at 80°-85° C. The reaction mixture 2,421,811 Smith et al. __________ __ June 10, 1947 .
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