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United States Patent Office Patented Apr 2,931,802 United States Patent Office Patented Apr. 5, 1960 1. 2 solved. Any unreacted anhydride and acid by-product are removed by distillation under reduced pressure. To re 2931,802 move traces of acid and the salt catalyst, the residue is dis solved in a water-immiscible inert solvent and the result MXED ESTERS OF GLUCOSE AND SUCROSE ing solution is washed with dilute NaOH or Na2CO3, George P. Touey and Herman E. Davis, Kingsport, Tenn., following which the aqueous layer is removed and the assignors to Eastman Kodak Company, Rochester, N.Y., inert solvent is distilled off under reduced pressure. Ordi a corporation of New Jersey narily, 2-3 hours gives sufficient time to run the reaction No Drawing. Application April 30, 1958 to completion although longer times. may be employed. Serial No. 731,890 10 If desired, an inert diluent may be employed in the esteri fication bath such as a ketonelike diethyl ketone, a hydro 7 Claims. (CI. 260-234) carbon such as toluene, or a chlorinated hydrocarbon such as propylene chloride. If a solvent is used its boil ing point should be within the range of 90-140 C. This invention relates to organic solvent soluble short 5 Acid diluents are preferably avoided since they may react chain fatty acid esters of sucrose and of glucose and with the anhydrides used, thereby altering the anhydride their method of preparation. In particular it relates to ratio employed. ... completely esterified or highly esterified mixed fatty acid To obtain non-crystallizing esters in accordance with esters of sucrose and glucose containing a combination of our invention the proportions of the combinations acetic acetyl and propionyl groups, or acetyl (or propionyl) and 20 anhydride-propionic anhydride, acetic anhydride-isobutyric isobutyryl groups as acyl substituents. anhydride, or propionic anhydride-isobutyric anhydride Sucrose octaacetate has been previously referred to as must be controlled within definite limits. In the case of being useful in the preparation of adhesives, paper finishes, glucose the total molar quantity of anhydride must not lacquers, resins, and plastics. This material is a white be less than 5 or more than 8 for each mole of the glu crystalline solid, its crystalline nature limiting its use as 25 cose. In the case of sucrose, the total molar quantity of a plasticizing material. When this material is incorpo anhydride must be not less than 8 nor more than 12. In rated into cellulose ester film base materials at normal the case of glucose, the acetic anhydride should not be plasticizer concentrations such as 10-50%, the films cast above 2 moles or below 0.25 mole per mole of glucose. therefrom become opaque and brittle due to crystallization The preferred ratio of reactants are 0.5-1.25 moles of of the sucrose octaacetate in the film. Also, sucrose octa 30 acetic anhydride and 5.25-5.75 moles of isobutyric or acetate has relatively high solubility in water and poor propionic anhydride per mole of glucose. This gives resistance to hydrolysis. Other fatty acid esters of sucrose (when using isobutyric anhydride), a substantially com have disadvantages of one kind or another when used as pletely esterified glucose acetate isobutyrate having an a cellulose ester plasticizer. For instance, sucrose octa acetyl content within the range of 4.3-23% and an iso propionate is also a crystalline solid very similar in 35 butyryl content between 39.5 and 63%. In the case of the properties to the octaacetate. The normal butyrate ester sucrose esters, the acetic anhydride should not be above 4 of sucrose develops disagreeable odor when subjected to mcles or below 1 mole per mole of sucrose being esterified. high humidities. The incorporation of considerable The most desirable ratio of reactants are within the range amounts of this material into cellulose ester films may of i-3 moles of acetic anhydride and 7-9 moles of iso result in soft, tacky surfaces. The simple esters of glu 40 butyric anhydride or propionic anhydride per mole of su cose possess similar characteristics when used as additives crose. There is thus obtained (when isobutyric anhydride in cellulose ester compositions. is used a substantially completely esterified sucrose acetate One object of our invention is to provide as new chemi isobutyrate with an acetyl content within the range of cal compounds substantially completely esterified odor 5.0-25% and an isobutyryl content between 31.7 and less sucrose or glucose acetate isobutyrates or acetate. 45 59%. When the amounts of the lower anhydrides are propionates characterized by non-crystallizing character higher or lower than the limits specified, the products istics. Another object of our invention is to provide as have a pronounced tendency to crystallize. Also, higher new chemical compounds a substantially completely amounts of acetyl than specified gave products which esterified odcrless sucrose or glucose propionate iso are less resistant to hydrolysis. - - - butyrate which is noncrystallizing. A further object of 50. The catalyst concentration may range from 1 to 20% our invention is to provide substantially completely esteri based on the weight of the sugar. Ordinarily, a concentra fied, organic solvent soluble sugar esters which due to their tion of 8% catalyst is sufficient. The catalyst may be a non-crystallizing pronerty, lack of odor, and excellent heat sodium, potassium, lithium, or calcium salt of a weak and hydrolysis stability, are ideally suited as plasticizers organic acid. The preferred catalyst is a salt whose anion or plastirizer extenders in cellulose ester compositions. A 55 corresponds to the anhydride being used. For instance, still further object of our invention is to provide a practi in making sucrose or glucose acetate isobutyrate the pre cal procedure for producing these non-crystallizing sugar ferred catalyst is sodium isobutyrate or a mixture of esters. Other objects of our invention will appear herein. Sodium acetate and sodium isobutyrate. It is most con It has been found that if a sucrose or glucose mixed venient to form the catalyst in situ by adding sodium hy ester is prepared containing at least 20% isobutyryl or 60 droxide to the mixture of the two anhydrides in forming propionyl based on the acyl content, the remainder being the esterification mass. The following examples illustrate acetyl or propionyl, those esters when incorporated in our invention. cellulose ester compositions, do not crystallize or other wise interfere with the clarity of products prepared there Example 1.-PREPARATION OF SUCROSE from, do not develop odor at high humidities and are 65 ACETATE ISOBUTYRATES resistant to heat and hydrolysis. - 1 mole (342 grams) of sucrose and 0.69 mole (27.6 The esters in accordance with our invention are pre grams) of sodium hydroxide were added to a mixture pared by heating sucrose or glucose such as at 90-140 C. of 8 moles of isobutyric anhydride and 2 moles of acetic with a mixture of (1) isobutyric anhydride, and acetic or anhydride. The mixture was rapidly stirred and was propionic anhydride or (2) acetic and propionic heated to 130 C. and maintained at that temperature anhydride in the presence of a salt of a weak 70 for 2 hours. The faintly amber colored solution ob organic acid until the product has been completely dis tained was concentrated by removing the acids and ex 2,981,802 3 4. cess anhydride under reduced pressure (2-5 mm. Hg.) at washes. The water layer was discarded and the toluene 90-100° C. The syrupy residue was dissolved in toluene was removed by vacuum distillation. There was ob and the resulting solution was thoroughly washed with tained 460 grams of a viscous, light colored, free-flowing aqueous 5% NaOH followed by several water washes. liquid which was glucose acetate isobutyrate. The glucose * The toluene was removed by distillation yielding a clear, acetate isobutyrate thus obtained was stable at 190° C. almost colorless highly viscous liquid which is sucrose for 2 hours and had excellent hydrolysis stability in boil acetate isobutyrate. ing water treated for 96 hours. The above procedure was The procedure was repeated varying the amounts of repeated several times varying the amounts of acetic and acetic anhydride and isobutyric anhydride in the esterify isobutyric anhydride within the limits specified in the ing mixture as shown in the table. 0. description. In every case, a non-crystallizing, light Mnles Moles Percent Hydrolysis Run Moles Isnbutyr- A cetic Percent Iso- Stability, Sucrose ic Anhy. Anhy- Acetyl butyryl Percent Physical Forn dride dride 0.01 HSEays. syrup crystallized within 0.02 Heavy syrup had not crystallized after 6 Inonths' storage. 0. Do. 0.32 Do. 0,9 Do. 1 The hydrolysis stahility is expressed as percent acid formed (calculated as acctic acid) after the sample had been boiled in water for 96 hours. Yields in all the above runs were in excess of 90%. The colored, viscous liquid was obtained in a yield of at least heat stability of each product was excellent when held 90%. The products obtained had excellent heat and at 190° C. for 2 hours. Analysis indicated each of the hydrolysis stability. products were substantially the octa substituted esters. Example 4.-PREPARATION OF GLUCOSE Example 2--PREPARATION OF SUCROSE 30 ACETATE ISOBUTYRATE PROPIONATE ISOBUTYRATE A slurry was prepared by heating at 130° C. for 2 hours A slurry was obtained by rapidly stirring together i with rapidly stirring a mixture of 1 mole (180 grams) of mole (342 grams) of sucrose, 0.69 mole (27.6 grams) of glucose, 0.25 mole (10 grams) of sodium hydroxide, 1.0 sodium hydroxide, 8 moles of isobutyric anhydride and 35 mole (130 grams) of propionic anhydride, and 5.5 moles 2 moles of propionic anhydride and slowly heating to (869 grams) of isobutyric anhydride.
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