UNITED STATES PATENT OFFICE. EDWARD C. SPURGE, OF NIAGARA FALLS, NEW YORK, ASSIGNOR TO OZONE WANILLIN COMPANY, A CORPORATION OF NEW YORK, . PROCESS OF MAKING WANLLIN, &c. No. 829,800. specification of Letters Patent. Patented Aug. 2, 1906. Application filed November 21, 1906, 8erial No. 288,373. To all whon, it may concer"70. added to the fluid to be treated the produc 55 Be it known that I, EDWARD CHARLEs tion of the resinous body is very considerably SPURGE, a subject of the King of England, diminished, the thickening of the mass pre residing in Niagara Falls, New York, have vented, and a more fluid condition thereof is 5 invented new and useful Improvements in maintained which is favorable to the oxida Processes of Obtaining Vanillin and Similar tion process and the obtaining of increased Bodies; and in order that others skilled in the ield. For this purpose a bisulfite salt may art to which my invention belongs may un added in the form of a solution and the derstand and practice the same I give the fol mass treated with ozone. .O. lowing specification. The vanillin formed combines with the My invention relates to a process for ob bisulfite, either wholly or partially with the 65 taining vanillin and similarly-constituted formation of a bisulfite compound which goes substances from carbon compounds which are into solution either wholly or partially, ac characterized by a benzene nucleus with a lat cording to the quantity of bisulfite employed. IS eral chain, (C.H.) Such carbon compounds That portion which forms the bisulfite com may have a lateral chain either in the form pound is less thick and more fluid and acts in o CH=CH-CH, or its isomer CH=CH-CH, the manner of an emulsifying medium. The carbon compound to which I particu During the reaction there is liberated an larly refer is isoeugenol. Heretofore it has amount of SO, and a certain amount of neu been proposed to treat such compounds sus tral sulfite and sulfate are formed. The lat pended in water or in the form of a solution ter, particularly the sulfate, being less soluble 75 with ozone or ozonized air, which by its re than E. are precipitated in a state action upon the compound converts the of fine division during the oxidation process same into the corresponding aldeyhde-as and being disseminated throughout the mass for instance, by the treatment of isoeugeno act favorably therein in keeping the same in a 25 in the manner stated the aldehyde EE is state of fine subdivision. It will be under produced. It has been found in practice stood that during the oxidation process the that this process results in a considerable ozonized air is blown through the reaction waste of material and a relatively small yield mass and the same is thereby kept in agita of the vanillin, and, further, that relatively tion. The bisulfite to be employed may be a large masses of material are required to be bisulfite of an alkali. Preferably I employ handled to obtain a relatively small propor bisulfite of soda. tion of the aldehyde. For the purposes of illustration I give the I have discovered that the relatively low following example of my invention as Epic: ield and other unfavorable results obtained to isoeugenol: To one hundred pounds of 35 St. above process, particularly in the case isoeugenol are added three hundred pounds of vanillin, are due in large measure to the of sodium bisulfite of about 36' Baumé. The formation and presence of a resinous body of mass is charged into a suitable receiver to unknown composition which is produced in which is connected a supply of ozone or 40 the reaction. This resinous body causes a ozonized air, and the latter is passed through thickening of the reaction mass and the alde the mass for a length of time sufficient to 95 hyde formed coagulates or agglomerates carry the oxidation to the desired degree. therein until as the reaction progresses this The skilled operator will readily determine thickening and agglomeration reaches a the degree of oxidation suited to the charac 45 point where the oxidizing action is seriously ter of the product he desires, the character of interfered with and impaired ind the further the ozonized air-that is, its proportion of OO production of vanillin materially diminished. ozone, &c. These conditions vary in prac It is the object of the invention to provide tice, and the skilled operator will determine means for preventing, the thickening and the proper length of time required to com So agglomeration referred to, and to maintain plete the process. In the process illustrated the reaction mass in a relatively thin fluid the ViA formed is recovered and sepa IoS condition and most favorable to the thor rated from the mass in any of the well-known ough oxidation of the carbon compound WWS. - have discovered that if certain salts be 8her carbon compounds of the character 2 829,300

like-maydescribed-for be treated instance, according iso-safrol to my and inven s compound in admixture with a solution of an tion with good results. alkali bisulfite with ozone or ozonized air. Having thus described my invention, the 3. The process of producing vanillin, which 2 o following is what I claim as new therein and consists in adding to a quantity of isoeuge desire to secure by Letters Patent: nol a proportion of bisulfite solution, and 1. The process of oxidizing a carbon com subjecting said mixture to the action of ozone pound having a benzene nucleus with a lat or ozonized air. eral chain CH to produce the correspondin 4. The process of producing vanillin, aldehyde, which consists in treating sai which consists in adding to a quantity of compound in admixture with a solution of an isoeugenol a proportion of a solution of so acid salt of sulfurous acid with ozone or dium bisulfite of about 36 Baumé and treat ozonized air. ing the mixture with ozone or ozonized air 2. The process of oxidizing a carbon com EDWARD C. SPURGE. pound having a benzene nucleus with a lat Witnesses: eral chain CHs, to produce the correspond WILLIAM P. HAMMOND, ing aldehyde, which consists in treating said H. C. WORKMAN.