Sucrose, acid hydrolysis

Sucrose on hydrolysis with dilute acids, or with the enzyme invertase (or ju-crase p. 514,) gives rise to one molecule of glucose and one molecule of fructose ... 

Sugar is destroyed by pH extremes, and inadequate pH control can cause significant sucrose losses in sugar mills. Sucrose is one of the most acid-labile disaccharides known (27), and its hydrolysis to invert is readily catalyzed by heat and low pH prolonged exposure converts the monosaccharides to hydroxymethyl furfural, which has appHcations for synthesis of glycols, ethers, polymers, and pharmaceuticals (16,30). The molecular mechanism that occurs during acid hydrolysis operates, albeit slowly, as high as pH 8.5 (18). 

Double Polarization. The Clerget double polarization method is a procedure that attempts to account for the presence of interfering optically active compounds. Two polarizations are obtained a direct polarization, followed by acid hydrolysis and a second polarization. The rotation of substances other than sucrose remains constant, and the change in polarization is the result of inversion (hydrolysis) of the sucrose. 

Orthoesters. The value of cycHc orthoesters as intermediates for selective acylation of carbohydrates has been demonstrated (73). Treatment of sucrose with trimethylorthoacetate and DMF in the presence of toluene-/)-sulfonic acid followed by acid hydrolysis gave the 6-0-acetylsucrose as the major and the 4-0-acetylsucrose [63648-80-6] as the minor component. The latter compound underwent acetyl migration from C-4 to C-6 when treated with an organic base, such as / fZ-butylamine, in DMF to give sucrose 6-acetate in >90% yield (74). When the kinetic reagent 2,2-dimethoxyethene was used,... 

Sucrose can, however, degrade to D-glucose and D-fructose in slightly alkaline solution at pH up to 8.3 (sucrose is most stable611 at pH 8.3-8.5, although the reason for this requires some elucidation), but this degradation proceeds by the normal acid-hydrolysis mechanism. In sucrose manufacture, therefore, the main reaction causing sucrose loss, between pH 7 and about 8.3, is the same acid hydrolysis that occurs at lower (acid) pH. 

Sucrose degrades in acid far more easily than in alkali, and invert sugar (the product of acid hydrolysis) is far more reactive in alkali than in acid. 

Because alkali degradation of sucrose does not result in inversion products, in slightly alkaline solution (pH < 8.5), the loss of sucrose to invert sugar (glucose + fructose) is a consequence of the acid hydrolysis mechanism, which provides D-glucose and D-fructose for further alkaline degradation. 

The hexoses that are the initial products of acid hydrolysis of sucrose (1) react at el vated temperature under the influence of acids to yield furfural derivatives (2). Thed condense, for example, with the phenols to yield triarylmethanes (3), these react furthei by oxidizing to yield colored quinoid derivatives (2, 4). Polyhydric phenols, e. g. resorj cinol, on the other hand, yield condensation products of Types 5 and 6 [2],... 

In 1886, Brown11 discovered an organism which formed extremely tough membranes when cultivated m suitable nutrient solutions containing carbohydrates such as D-fructose, D-mannitol or D-glucose ethanol, sucrose or starch did not support membrane formation by this organism which Brown called Bacterium xylinum ) (Acetobacter xylinum). The membranes were readily soluble in cuprammonium hydroxide solution and yielded a dextrorotatory sugar upon acid hydrolysis. These properties and the results of combustion analysis led him to believe that the membrane was cellulose. 

Many plants store carbohydrates in their tubers in the form of polysaccharides which upon acid hydrolysis yield D-fructose as the main product. These polysaccharides differ from one another in the size of the molecule as well as in the position of the linkages between the D-fructose residues. Polyfructosans have also been prepared by enzymic action on sucrose. 

Similarly to the hydrolysis of sucrose, acid exchanged resins can be utilized, in one case to give 75% hydrolysis of triglycerides after six hours at 155 °C. It was shown that the Brondsted acid sites catalyze the hydrolysis reaction, which was performed in the liquid phase with continuous steam injection.The same authors reported that polystyrene sulfonic cation-exchange resin, loaded with 13% of the superacid H3M0, gave 74.5% hydrolysis of palm oil at 155 °C in a batch reactor also operated with steam injection. 

Acid Hydrolysis. Lactose is resistant to acid hydrolysis compared to other disaccharides such as sucrose. In fact, organic acids, such as citric acid, that easily hydrolyze sucrose are unable to hydrolyze lactose under the same conditions. This is useful in analyzing a mixture of these two sugars, because the quantity of sucrose can be measured by the extent of these changes in the optical rotation of reducing power as a result of mild acid hydrolysis. The speed of hydrolysis of lactose varies with time, temperature, and concentration of the reactant, as shown in Table 6.8. 

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