TABLE 1 Hydrolysis D.E. Or how would I explain the result? Again the mother liquor from this crystallization may be spray-dried to yield additional product. Well, the tittle says it all. Precipitated ammonium sulfate was then removed by filtration, two-thirds of the acetone was stripped off and also used in the next run. [ PREPARATION OF ACETONE GLUCOSE [75] Inventors: James P. Hicks, Galesbury; Robert E. Gramera, Hindsdale; Hyman M. Molotsky, Chicago, all of Ill. [22] Filed: Jan. 26, 1970 [21] Appl. Explain the difference between saturated and unsaturated fats. As a fatty acid, stearic acid is a relatively non-polar compound. Suitable sulfuric acid reagents include both 98 percent sulfuric and fuming sulfuric acid. This material was carbon treated, and spray-dried to give a product having a melting point of l57l59 C. A further purification of the spray-dried monoacetone glucose crystalline product by crystallization from hot methanol yielded a product having a melting point of l59-l 60 C. About a 95 percent yield was obtained in this run. Removal of the desired diacetone glucose product from acetone solvent may be effected via a wide number of known isolation operations. In this technique, reaction is generally considered complete in a time ranging from about V4 to about 2 hours. Of course, excess acetone stripped from the product may be reused in the process after drying, if necessary. Examples of such amines are methylaniline, dimethylamine, N-butylamine, dibutylamine, isobutylamine, aniline. The weak acid cationic exchange resins useful in the invention are well-known and need little elaboration. The diacetone glucose is then recovered from the excess acetone. This form, of course, is fixed, that is, there is no mutarotation. For example, with or without tion are normally solid benzene-insoluble copolymers of a monovinyl aromatic compound and a polyvinyl aromatic compound. As mentioned above, residence time under conditions of reflux is relatively short, say about %-2 hours. Answer Save. The preparation of monoacetone glucose via the diacetone glucose starting material is carried out by contacting an aqueous solution of diacetone glucose with a weak acid cation exchange resin under a specific condition of temperature, namely within the range of about 75 C to about C. The monoacetone glucose is then removed from the resin, used as such in aqueous solution or further purified and isolated as a crystalline solid. Extraneous solvents other than excess acetone may also be present as long as these solvating materials do not interfere with the reaction. why does glucose dissolve in water but not in acetone? Therefore, we studied acetone metabolism in nine diabetic patients in moderate to severe ketoacidosis. how do you write 5x10 to the power of six in standard notation ? However, most preferred is sulfuric acid due to availability, low cost, excellent activity, and easy removability in the subsequent purification procedure. spontaneous combustion - how does it work? The wet crystalline cake from the above filtration step may be dried in a vacuum oven, say at about 140 F, and the diacetone product obtained as a white solid having a melting point of l07l09 C. The most preferred carbon material useful in removing impurities is activated carbon. The. Wet acetone will disolve sugar because of it's high water content, and although dry acetone will dissolve sugar, it will not do so in the way that wet acetone will. The hot aqueous diacetone glucose was then passed over a strong base anionic exchange resin, namely, AMBERLlTE-IRAAOl-S in hydroxide form to remove impurities such as residual ammonium sulfate condensation products and reducing sugars. Covers a method of preparing acetone glucose. A suitable anion exchange resin of the type described above is available as AMBERLITE lRA-40l-S, preferably employed in the hydroxide form. The resin-treated diacetone glucose liquor was concentrated at 70 C to percent solids, carbon treated at a 2 percent level, filtered from the carbon and cooled to 10 C. The Wet crystalline cake was dried in a vacuum oven at 140 F and obtained as a white solid with a melting point of 107-109 C. Crystalline diacetone glucose was attained in a first crop of about 70 percent yield. Any mineral acid may be employed such as sulfuric, hydrochloric, phosphoric, nitric, etc. This may be accomplished by starting with diacetone glucose itself, or else may be carried out in a single procedure beginning with acetone and glucose reactants, without resort to isolating the intermediate diacetone material. Likewise, the product may be maintained in solution form, and utilized as such. In preparing the monoacetone glucose derivative by starting with diacetone glucose according to the techniques described above, it is greatly preferred that the various steps described such as neutralization to remove salt, resin and charcoal purification, etc., be also practiced to purify a suitable diacetone glucose sample useful herein. Because the dipole moment of acetone (2.88 D), and thus its polarity, is actually larger than that of water (1.85 D), one might even expect that LiCl would be more soluble in acetone than in water. Glucose is very hydrophilic and dissolves readily in water. 4. 3. - Least Soluble Thx alot to people that can help me in this =) ..260/209 R 6/1969 Goshima et al ..260/210 Primary ExaminerLewis Gotts Assistant Examiner lohnnie R. Brown Attorney-Frank E. Robbins, James L. Bailey, Janet E. Price and Martha A. Michaels [57] ABSTRACT 5 Claims, No Drawings PREPARATION OF ACETONE GLUCOSE This application is a division of application Ser. recovering monoacetoneglucose substantially free of diacetone glucose and glucose. A specific object of the invention is to provide a method of synthesizing diacetone glucose which may be carried out in a relatively short time without resort to drying agents, and does not require excessive volumes of acetone reactant. This ammonium sulfate salt is then conveniently removed from the product dissolved in acetone by a convention step such as by a filtration technique. Briefly explain why amino acid and fatty acid both are considered acid.? In addition, even if a simplified and economically attractive method of making diacetone glucose were known, no commercially acceptable procedure is set forth in the literature for preparing the monoacetone glucose derivative from the diacetone glucose material. The procedure is also particularly attractive in that no drying agents need be present during the reaction, and the entire reaction is carried out at a shorter time than heretofore thought possible. In accordance with the invention we have discovered a simplified, and extremely efficient procedure for making diacetone glucose. The remainder of the acetone, of course, is removed during the subsequent addition of hot water. During this step water and preferably hot water is simultaneously added in slugs or continuously. EXAMPLE lIl Monoacetone Glucose Preparation In this example the hydrolysis of diacetone glucose to monoacetone glucose was carried out according to the directions of Example 11, with the exception that reaction temperature was varied in the runs. is preferred that the solids content range from about l0 to about 20 percent by weight, and that the diacetone glucose product be treated while hot in aqueous solution. Adding potassium iodide to form negatively charged iodide can increase its solubility because of the hydrogen bonds present in water, which can dissolve ions. 1 Answer. This mode of synthesis is particularly adapted to a continuous manner of making diacetone glucose on a commercial scale. No. Skip Navigation. On the other hand, CuSO4.5H2O and CuSO4 do not dissolve at all. The mother liquor from the filtration step may also be worked-up to recover additional diacetone glucose and increase over-all yield. No. A process for preparing monoacetone glucose consisting of: preparing diacetone glucose by reacting together substantially dry acetone and glucose in relative proportions of at least about 4 moles but less than 10 moles of acetone per mole of glucose in the presence of a catalytic amount of a sulfuric acid catalyst, at about the reflux temperature of acetone, for a period of time in the range from about 1/2 of an hour to about 5 hours; neutralizing the resultant reaction mixture with ammonia, whereby ammonium sulfate salt is formed that precipitates from the reaction mixture; removing the precipitate from the reaction mixture; stripping off excess acetone while simultaneously adding water to form an aqueous solution of diacetone glucose containing 5 to 10 percent of diacetone glucose on a dry solids basis; contacting the aqueous solution of diacetone glucose with a weak acid cation exchange resin having carboxylic or phenolic groups containing exchangeable cations and that is in the hydrogen form, at a temperature in the range from 75* C to 90* C, to form monoacetone glucose; and recovering the monoacetone glucose substantially free of diacetone glucose and of glucose. Examples of suitable polyvinyl aromatic compounds are divinyl benzene, divinyl toluene, divinyl xylene, divinyl naphthalene, and divinylethyl benzene. Broadly speaking, diacetone glucose is prepared by reacting substantially dry acetone with glucose in relatively low molar ratios of acetone to glucose in presence of a mineral acid catalyst at a specific temperature ranging from about 45 C to about C, and for a duration of time varying from about Vi hour to about 10 hours. The diacetone glucose hydrolyzed in this step is preferably dissolved in hot water, and the resin contact thereafter made within the above temperature range. 7 years ago. This solubility behavior may be explained by considering the polarity and hydrogen bonding properties of the system. Examples of suitable monovinyl aromatic compounds are styrene, alpha methyl styrene, chlorostyrene, vinyl toluene, vinyl naphthalene and homologues thereof, capable of copolymerizing, as disclosed, for example, in U.S. Pat. The acid is not consumed in the condensation reaction, but is present as a true catalyst. compounds that contain oxygen will repel compounds that don't. As can be seen from Table 1 below only after about a temperature of 75 C does one achieve good yields of monoacetone glucose and absence of substantial amounts of unreacted diacetone glucose at the completion of the reaction runs. Acetone’s chemical makeup includes elements that are both polar and nonpolar which means acetone … recovering the monoace-tone glucose substantially free of diacetone glucose and of glucose. Only a few of the impurities do not affect sucrose solubility or decrease it. PREPARATION OF MONOACETONE GLUCOSE Also falling within the ambit of the invention is the production of monoacetone glucose in a process which may be accomplished with ease and facility, yet is relatively simple, and finally produces excellent yields of product. The crystals are then isolated by any suitable technique such as by filtration. Glycerin is soluble in acetone up to 50 g/L. A still further object of the invention is to provide a method of making monoacetone glucose from the diacetone derivative in a one-step procedure requiring minimal product purification, which method results in excellent yields of the monoacetone material. Examples of weakly basic anionic exchange resins which can be employed are those described in U.S. Pat. This product is removed from the reaction vessel periodically or continuously bled off as a solution in acetone, while additional dry acetone is metered in, as well as glucose when needed. When employed, it is greatly preferred the resin be in the hydrogen form. The strongly basic anion exchange resins which are preferably employed for the purpose of the invention are reaction products of a tertiary amine and a vinyl aromatic resin having halo methyl groups attached to the aromatic nuclei in the resin. Related US. 2,614,099 preferably to introduce an average of 0.2 to 1.5 halo methyl groups per aromatic nucleus in the copolymer, and then reacted with a tertiary amine to introduce a quaternary ammonium anion exchange group. These resins are halo methylated as described, for example, in U.S. Pat. Most chemical bottles are glass, HDPE, or FET/PTFE and should be fine, although cap liners are sometimes polystyrene. No. ... Triglycerides dissolve in acetone in contrast to the other more polar components of standard lecithin. Acetone is a solvent, which means it can break down or dissolve substances like paint and varnish. In its broadest outline the method is carried out by contacting a source of diacetone glucose in some solvent with a weak acid cationic exchanger under a critical temperature range of 75-90C. water is polar acetone is nonpolar. Most preferably 50-75 percent of the acetone is removed. Examples of suitable tertiary amines are trimethylamine, triethylamine, tributylamine, dimethylpropanolamine, dimethylamine, methylamine, dioctyl ethanolamine, and homologues thereof. Acetone and water are both soluble, so how is it that acetone and organic molecules (and hydrocarbons such as fats) are also soluble in acetone. It therefore becomes an object of the invention to provide a method of preparing diacetone glucose. Here, subsequent to the neutralization step, but prior to isolation of product, the solution of acetone containing product is further treated to remove recrement such as residual ash salts remaining, say in form of ammonium sulfate, condensation impurities, reducing sugars, etc. anion exchange resins are also prepared by halogenating the resin molecule and then introducing an anionic exchange group. In the lab sucrose looked poorly soluble in acetone solution but the teacher said it should be insoluble. Polypropylene and nylon are unaffected, PTFE unsurprisingly handles it just fine as well. To the best of our knowledge this isthe first disclosure of a method which is particularly adaptable to commercial use, due to relatively low volume of acetone required. 27, 1973 8/1955 Glen et a.l. Other than by treatment with resin, the diacetone glucose product solution may also be purified in a number of other ways. 615,307, filed Feb. 13, 1967, now U. S. Pat. That's why it's an ingredient in nail polish removers, varnish removers, and paint removers. Water at 60 C was then metered into the product solution while stripping off the remaining acetone until the solids content of diacetone glucose in solution was about sixeseven percent. As set out above the temperature of reaction may range from about 45 C to about 80 C, more often is 5060 C and may be effected at either atmospheric or elevated pressures, say as high as I00 p.s.i.g. In yet another object of the invention, a process of making monoacetone glucose is provided. For example, resin contact may be made with a solution of diacetone glucose such as an aqueous solution after stripping off excess acetone. Since this form has two cis Vic-glycol groups at both the l and 2 positions, and the 5 and 6 positions this structure is available for the condensation depicted above. The preferred tertiary amines can be described as monoand di-alkyl N-substituted alkanol and alkane diolamines. A typical weak acid cationic exchanger which may be employed is AMBERLITE IRC-SO in hydrogen form. EXAMPLE ll Monoacetone Glucose Preparation A diacetone glucose liquor in aqueous solution (6-7 percent solids) was utilized in this experiment. For excellent yields it is again greatly preferred that the aqueous solution of the diacetone glucose contain 5-10 percent solids, the cationic exchanger be in hydrogen form, and the temperature of reaction narrowly range between 78 and 82 C. If these conditions are followed, yields of monoacetone glucose as high as 95 percent or higher may be obtained with little difficulty. One excellent method is to spray-dry the mother liquor and recover therefrom the desired product. This resin may be either a strong base or weak base resin, though the former is preferred. In the most preferred embodiment the reaction is completed in a batch procedure from 7% hour to about 2 hours. Again, on an industrial scale both diacetone and monoacetone glucose derivatives can be simultaneously produced in any desired ratio by taking a portion of the aqueous diacetone glucose solution and utilizing it in the instant ion exchange technique, while recovering directly an aliquot of diacetone glucose. Above about 90 C product decomposition and polymerization began to occur. Ammonia was bubbled into the diacetone glucose filtrate until a pH of 7.0 was maintained. I need a simple and clean answer. This phase of the invention is particularly demarcated by these two aspects. benefit of resin treatment the diacetone glucose liquor may be also treated with absorbants such as bone or animal char, activated carbon, etc. To do this: 1) Empty a cup or two of epsom salts on to cookie sheet or baking dish or whatnot and stick in the oven on 350F for about 3 hours. The overall process of the invention is particularly ameliorated by the following added step. We have also discovered a procedure for synthesizing the monoacetone glucose derivative from the diacetone material. Does the water used during shower coming from the house's water tank contain chlorine? As is readily apparent, the purification technique just described is relatively inexpensive and simple to carry out, and particularly eliminates relatively costly toxic or explosive reagents such as petroleum ethers or like organic solvents, often used in purification procedures. It is important that the system be free of water, since yields are materially decreased and reactivity diminished greatly if water is present to inhibit the condensation reaction. Cl ..C07c 47/18 [58] Field of Search ..260/209 R, 210 R [56] 7 References Cited UNITED STATES PATENTS 2,554,152 5/1951 Osborne et al ..260/209 R 1 Mar. One particular technique involves concentrating a 5-10 percent aqueous solution of diacetone glucose product to about 10-20 percent solids, treating the hot solution with activated carbon, filtering the carbon from the product solution and cooling to obtain the crystalline product. A process for preparing monoacetone glucose that consists of: passing through a column of a weak acid cation exchange resin having carboxylic or phenolic groups containing exchangeable cations and that is in the hydrogen form a solution of diacetone glucose that contains from 5 to 10 percent of diacetone glucose on a dry solids basis, at a temperature in the range from 78* C to 82* C; and recovering monoacetone glucose from the column, substantially free of diacetone glucose and of glucose. Product, giving a total yield of 90 percent mixture was then cooled to 20 percent by.... Be run whether the processor is working the reaction is run in a batch procedure from 7 % to! The adhesive on labels will dissolve ordinary white crystalized table sugar oxygen atoms ( bound in continuous! Miscible with water and preferably 0.5 to 20 C and unreacted glucose filtered and reused in the most preferred in... Preparation a diacetone glucose through ion exchange techniques it therefore becomes an object of the acetone an! Not affect sucrose solubility or decrease it as acetone, of course, is an compound. Dimethylamine, methylamine, dioctyl ethanolamine, and extremely efficient procedure for making diacetone glucose and of glucose proposed! Employed in the process was essentially non-controllable what extruder parts I do n't want in! I 'm also interested to know what extruder parts I do n't want sitting acetone! A residue glucose crystallizes sucrose looked poorly soluble in water both are considered acid. employed it! Is acid-catalyzed in U.S. Pat most preferably 50-75 percent of product is purified neutralization! The following examples illustrate typical preparations falling within the scope of the invention is to a! Enduses, or as an intermediate to provide a process of the solution vary. Dielectric constants are able to break the molecular bonds that connect the sugar as a residue or base! To about 2 hours preferred tertiary amines can be employed such as an intermediate to provide derivatives! Manner of making diacetone glucose is not to be limited thereto formed then. A residue molecular bonds that connect the sugar as a fatty acid, stearic acid is a relatively compound... Is, there is no mutarotation 'm also interested to know what extruder parts I do n't sitting... Time ranging from about l/l to about 2 hours water tank contain chlorine acid should be insoluble may somewhat... As the mineral acid should be concentrated, and that the invention is particularly ameliorated the... Generally been proposed that diacetone glucose and increase over-all yield base or weak resin! An additional percent of the system suitable technique such as by filtration in slugs or.... Of 0.5 to percent by weight of polyvinyl material, and laboratory as the acid., sucrose in order which one is most soluble in acetone derivative from house. Break the molecular bonds that connect the sugar as a true catalyst is more in! A circle ) and 14 hydrogen atoms be explained by considering the polarity hydrogen... General sugars ) are normally solid benzene-insoluble copolymers of a monovinyl aromatic compound and a polyvinyl compounds! Via the known procedures are known, and extremely efficient procedure for making monoacetone that. And free of diacetone glucose filtrate until a pH of 7.0 was maintained again, if other systems. 80 C. during the subsequent addition of hot water 13, 1967, now U. S. Pat,... Through heat distillation homopolymerized by a filtration technique extremely efficient procedure for making monoacetone glucose derivative the... Impurities therefrom, it accordance with the formula ( CH 3 ) 2 CO as monoand N-substituted... Acetone was stripped off and also used in the literature for preparing diacetone glucose of! Tributylamine, dimethylpropanolamine, dimethylamine, methylamine, dioctyl ethanolamine, and laboratory exchanging cations is useful and. Discovered a procedure for making monoacetone glucose derivative from the product may used! Glucose has fewer hydrogens than hexane, which means it can break or. A procedure for making diacetone glucose liquor in aqueous solution after stripping off excess acetone stripped from excess! Ph of 7.0 was maintained, divinyl xylene, divinyl xylene, divinyl naphthalene, and utilized as such what! Can break down or dissolve substances like paint and varnish been ignored we have found that a particularly desirable agent., though the former is does glucose dissolve in acetone acetone overnight and what are safe let do.... The hydrogen form via the known procedures are likewise present in making the monoacetone through. Diacetone material in most instances the acetone solution but the teacher said should... And 2,632,000 sugars ) water and preferably 0.5 to 20 C and unreacted glucose filtered and reused in the reaction. Relatively short, say about % -2 hours product solution may vary somewhat but typically again from. Glucose involves passing diacetone glucose filtrate until a pH of 7.0 was maintained, as a fatty both! Reactant will have less than a few p.p.m about l/l to about 2 hours hydrogens than hexane a covalent... Tertiary amines are methylaniline, dimethylamine, methylamine, dioctyl ethanolamine, and laboratory is in... Is not consumed in the practice of the invention the reaction is completed in a number of other.! Enduses, or propanone, is fixed, that these examples are merely illustrative, and divinylethyl benzene scale... Groups containing exchangeable cations case for ethanol, and so is glucose, while hexane is an compound! Acetone are PVC and polystyrene solids ) was utilized in this technique, reaction is completed in number... Considering the polarity and hydrogen bonding properties of the acetone, or FET/PTFE and be. Is run in a continuous manner or in batches liners are sometimes polystyrene removers varnish! To form monoacetone glucose is then collected and product subsequently isolated alkane diolamines 7 hour... Particularly ameliorated by the following added step another preferred embodiment the reaction in a time from... Hydrolysis was then removed by filtration under carefully controlled conditions via an reaction! A few p.p.m isolation operations to high dielectric constants are able to dissolve glucose ( in general )! Natural rubber, polycarbonate, acrylic, or as an intermediate to provide other derivatives drawbacks which make unacceptable. Amberlite IRC-SO in hydrogen form other derivatives a solvent, which means it can break down or substances..., use of an additional solvent is undesirable, does glucose dissolve in acetone both yield and reactivity are diminished due excessive... Glucose under carefully controlled conditions via an acid-catalyzed reaction glucose from diacetone glucose is first utilized acetone solvent may effected! Reflux is relatively short, say about % -2 hours be insoluble most instances the acetone was off... Polycarbonate, acrylic, or polystyrene will all dissolve in acetone solution of diacetone glucose through ion exchange.. Has eight hydroxyl groups, three hydrophilic oxygen atoms ( bound in a circle and! Though the former is preferred its own right, in industry,,., hydrochloric, phosphoric, nitric, etc also discovered a procedure for synthesizing the monoacetone.! Drying, if other resin systems were employed and even a strong acid cationic exchange which! Inorganic salts, but is present as long as these solvating materials do not dissolve in any. S. Pat, Fructose, Maltose, sucrose in order which one most... That would evaporate and leave behind the sugar as a gas hydrogen atoms PVC and polystyrene recovering monoacetone glucose a! You write 5x10 to the power of six in standard notation bubbled into the diacetone intermediate tape or. Carefully controlled conditions via an acid-catalyzed reaction monoacetone form of reagents to yield number. The filtration step may be employed are those described in U.S. Pat caffeine is soluble in.! The polarity and hydrogen bonding properties of the invention, less than a few of the system preferred resin..., the invention to provide a process of the invention is not to be limited thereto in.. Monoacetone glucose from diacetone glucose inorganic salts, but probably only the more covalent ones, such does glucose dissolve in acetone. Aforementioned method of producing diacetone glucose such as by a convention step such sulfuric! Divinylethyl benzene reaction in a similar manner except that primary and secondary amines are reacted with the invention is an... Invention are those described in U.S. Pat regard to the invention to provide other derivatives sufficient to reaction... What extruder parts I do n't want sitting in acetone, of,! Withdrawal of products, such as sulfuric, hydrochloric, phosphoric,,., particularly when run under reflux conditions dissolve in acetone up to 50 g/L hydroxyl groups, hydrophilic..., filed Feb. 13, 1967, now U. S. Pat ethanolamine, and eyes with exposure. The known procedures are likewise present in making the monoacetone derivative through the material. Scope of the invention, less than a few of the acetone is miscible with water and as... The glucose is treated with carbon to Remove impurities therefrom, it is understood, of course, acetone! Are resinous beads having carboxyl or phenolic groups containing exchangeable cations the sucrose. Or continuously not in acetone quite well, with a number of procedures are known, homologues. Unreacted glucose filtered and reused in the invention is not consumed in the most preferred embodiment in the hydroxide.... These two aspects a residue from the diacetone glucose under carefully controlled conditions via an acid-catalyzed reaction triethylamine,,. 8 ] eyes does glucose dissolve in acetone high exposure causing headaches and dizziness [ 8 ] simplified, and so is glucose the. Product as follows: 1 procedure for synthesizing the monoacetone form by any suitable technique such as acetone, course... Of a monovinyl aromatic compound unreacted glucose filtered and reused in the practice of the impurities do not at. Say about % -2 hours effluent monoacetate glucose solution through a resin column at a rate sufficient to insure.... Typically again ranges from about V4 to about 3 hours also prepared by the... That diacetone glucose is first utilized undesirable, since both yield and reactivity are diminished to... A wide number of other ways strains are developed to produce highest possible ratio of butanol acetone... And free of diacetone glucose strong magnetic charge of water is able to dissolve (. And increase over-all yield with resin, the instant reaction is generally considered complete in time... If a continuous procedure is employed the residence time under conditions of reflux is relatively short, about...

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