Patented Nov. 2 82 1939 UNITED STATES PATENT OFFICE 2,181,47,6 @ALIPHATIC HYDROXY-ETHEP. KETONES Albert Frank Bowles, Jersey City, and Saul Kaplan, Teaneck, N. J., assignors to The Richards Chemical Works, Incorporate@d, 'Jersey City, N. J., a corporation of New Jersey No Drawing. Application June 12, 1936, Serial No. 84,896 7 Claims. (Cl. 260-458) T'his invention relates to the production of assistants for use in the processing and treatmert of pelts, furs, leather and textiles, and intermediates for the manufactvre of such assfstants anci other uses. Many of the compounds I bo'bh the final products and al@o the iritermediates, are new per se, apart fr6m any u@e, to which they may be put. We have dise6vered that an alkylene oxide -,vill react with an allphatic or aromatic aldehyde to form an hydroxy ketone of the following structure: Ri-0--@-R2-OH 11 0 where R, signifies the aromatic or aliphatic nucleus and R2 Signifies the radicdl of the alkylene oxide. The reaction involves the breaking of the heterocyclic ring of the alkylene oxide at the oxygen atom, so that the latter has a free bond to unite with the hydrogen of the aldehyde grou]@.. T'he free carbon bond of the oxide links itself to the carbon of the aldehyde group. This is illus25, trated below: Acetaldehyde + Ethylene oxide CH3.C!H, + Hsc =CH3.CO.CH2.CH2.01f 0 30 0 E2c---T The reaction may be typified as follows: Ri-CHO+R20@Ri-C-Rr--OH 35 11 0 We have discovered that if two molecular eq v Ul _ alents of the alkylene oxide are used to each inolecular equivalent of the aldehyde, the addi40 tional equivalent of the alkylene oxide adds itself to the first alkylene oxide group, which in turn is attached to the aliphatic or aromatic aldehyde nucleus, as indicated below: 45 Ri-C-Rr-O-R2-OH 0 More generally: Ri-c-(R2--O)@H 50 wher,e n may be any number from 1 to 2, 4, 10 or more. Practically any conipound containing an alde.5,r) hyde group may be used, such as the following: (1) Aliphatic aldehydes, saturated or unsaturatedi straight or branched chain, containing from 31 or pr6ferably 5, to 20 carbon atoms. (2) Aliphatic hydroxy aldeh des with the above 5@ number of carbon atoms, such as glyceric aidehyde@an,d the aldoses. (3) Aliphatic aldehyde acids with the above number of carbon atoms, such as 1, carboxyoctanal. (4) Aromatic aldehydes, such as benzaldehyde, cimamic@ aldehyde. (5) Arornatic hydroky aldehydes,, such as hydroxy benzaldehyde, salicyl aldehyde, anisic aldehyde and vanillin or its homologues. The reactions noted above require a tempera-, ture of around 120 to 200' C. to bring them to completion. This involves the use of eithe-r an autoclave or a refiux condenser for the reason that the lower members of the alkylene oxide series 20 are, read@ly volatil6. For exalnple, propylene@ oxide boils at 35' C. and butylene oxide at 51' C. The products of the reaction between su oxides and the hkdroxy or aldehyde compo 25 are, however, substantially nonvolatile. @Using dn autoclave, the reacting substances are ititroduced cold, the autoclave is closed and then heated to between 1201 and 200' C. The volatiliz8@tion of the oxide raises the pressure, but owing 1 30 to the non-volatile character of the reaction prpduct, as soon as the reaction is complete, the pressure drops substantially to zero. TTiis fact provides a convenient method for deterrnining the end point of the process. 1 35 Usi,ng a reflux condenser, the oxide vaporizecl at the beginning of the reaction is returned to the reaction vessel. As the reaction proceeds, t4e ternperature is raised until refluxing ceases at around 180- C. 40 The reactions noted above may be aided by means of a suitabie catalyst, such as an alkali hydroxide, acetate or borate, a mineral acid, or aluminum, calcium, ferric or zinc P-hloride., The use of such a catalyst enables the reaction to be carried 6ut at a considerably lower temperature (arid hence pressure) than is possible where no catalyst is used. The use of a cata;lyst also reduced side reactions to a minimum. The properties of the foregoing compounds 50 which make them valuable in the processing or treatment df leathers, pelts, furs and textiles may be enhanced by their sulfatiop, or both sul ation and sulfonation in the case of products having an, aromatic group or nucleus. This is 55

2@ 2@181,476 especially true of properties requiring water solubility for their action, such as penetrating, detergent and wetting properties. The temperature of the reacting mixture should be kept down by suitable cooling means to belo* 80' C., and prefembly below 30' C. The mixture is stirred until it becomes water-soluble. This usually requires three hours or more. If the hydroxy ketone or like product contains 10 an aromatic group or nucleus, like phenyl, then such group will be sulfonated at the 8@me time that sulfation occurs at the hydroxyl group. In such cases the quantity of sulfuric acid added should be two equivalents, or more, instead of 15 only one. While the sulfated compounds may be made by first reacting the alkylene oxide and the aldehyde compound and then, as a separate step, sulfating the product, such procedure is not essdntial. 20 The process may be made a one-step process by adding the sulfuric acid to the initial reacting materials. Alternatively, the hydroxy material m ay be sulfated and then treated with alkylerie hydroxide. 25 What is