4. A process for preparing monoacetone glucose consisting of: forming 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 mineral acid, at a temperature in the range from about 45* C to about 80* C for from about 1/4 of an hour to about 10 hours; recovering unreacted excess acetone and diacetone glucose from the reaction mixture; removing the excess acetone from the diacetone glucose; forming a solution of the diacetone glucose that contains from 5 to 10 percent by weight of diacetone glucose on a dry solids basis; contacting said solution 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. The diacetone glucose is concentrated to about a 5-l0 percent solids content at this point, which amount is soluble in the hot water solution. These bonds will keep acetone dissolved completely in water, resulting in … Diacetone glucose may be used for a variety of enduses, or as an intermediate to provide other derivatives. Or how would I explain the result? Above about 90 C product decomposition and polymerization began to occur. No. 2. Skip Navigation. Glucose has a lot of hydroxyls. When an aqueous solution of diacetone glucose is treated with carbon to remove impurities therefrom, it. 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. On the other hand, CuSO4.5H2O and CuSO4 do not dissolve at all. A process for preparing monoacetone glucose that consists of: contacting a solution of diacetone glucose that contains from 5 to 10 percent diacetone glucose on a dry solids basis 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 78 C to 82 C, by adding beads of the resin to the solution to form a slurry; agitating the slurry for a period of time from 1/10 of an hour to 3 hours; and. 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. If a continuous procedure is employed the residence time of reactants before withdrawal of products is substantially the same as set out above. 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. During this step water and preferably hot water is simultaneously added in slugs or continuously. 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. Excellent yields are realized if these directions are carefully followed. benefit of resin treatment the diacetone glucose liquor may be also treated with absorbants such as bone or animal char, activated carbon, etc. Another preferred embodiment to form monoacetone glucose involves passing diacetone glucose solution through a resin column at a rate sufficient to insure reaction. Also covers a procedure for making monoacetone glucose from diacetone glucose through ion exchange techniques. In many instances, hydrolysis of the diacetone glucose to the monoacetone material is accompanied by severe decomposition, and other serious side-effects in the proposed processes. Give examples? Specifically, a weak acid cationic exchange resin, AMBER- LITE lRC-SO in hydrogen form was preheated to about 80 C and added to this heated diacetone glucose aqueous liquor. The actual time for any one run, batch or continuous, is, of course, dependent upon other presented variables such as molar ratio of reactants, temperature, etc. The contact of product solution with resin may be effected in a variety of ways, but most preferably is carried out by either the slurry or column techniques. The invention is hereby claimed as follows: 1. The overall process of the invention is particularly ameliorated by the following added step. Generally, the reaction is allowed to proceed after start-up until excess acetone present contains dissolved therein a substantial amount of the desired diacetone glucose product. Glucose, Fructose, Maltose, Sucrose In order which one is most soluble in water 1. No. Big Bird Y. It has generally been proposed that diacetone glucose be conventionally hydrolyzed with a number of reagents to yield the monoacetone form. But I got it wrong. When employed, it is greatly preferred the resin be in the hydrogen form. This resin may be either a strong base or weak base resin, though the former is preferred. . Also covers a procedure for making monoacetone glucose from diacetone glucose through ion exchange techniques. 615,307, filed Feb. 13, 1967, now U. S. Pat. Thanks Metals are OK but acetone will remove any grease, oil or pant on them. 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. 615,307, Feb. 13, 1967, Pat. View chapter Purchase book. In a greatly preferred embodiment in the invention the reaction is run in a continuous manner. Again the reaction is completed in substantially less time than heretofore thought possible, and most times can be completed in A 10 hours, and more often within 178 hour and 5 hours. 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. Examples of strongly basic anionic exchange resins which can be employed in the practice of the invention are those described in U.S. Pat. When a portion of the acetone is removed by stripping from the diacetone glucose product prior to addition of any water, it is preferred that at least 50 percent of the acetone be removed prior to water addition. 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. CoCl2 also dissolves, it gives a blue solution. 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. 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. recovering monoacetone glucose that is substantially free of diacetone glucose and of glucose. When sulfuric acid is used as the mineral acid catalyst, we have found that a particularly desirable neutralizing agent is ammonia. Thus, by an overall single procedure one can prepare monoacetone glucose in commercial quantities, starting with glucose and acetone as set out above, utilizing steps just mentioned to produce diacetone glucose, and following in a contiguous manner the just-mentioned monoacetone synthesis. [ 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. So, can anyone tell me which of the following would disolve in acetone: ABS - Yes, it does PLA - 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. 4. Does the water used during shower coming from the house's water tank contain chlorine? Related US. Polar organics like acetone or isopropanol or ethanol (or vodka) will dissolve it because you get hydrogen bonding that hold the molecules in solution. 0 … Most preferably 50-75 percent of the acetone is removed. This phase of the invention is particularly demarcated by these two aspects. In like manner, monoacetone glucose production on a commercial scale has also been hindered, since no simple procedure is known for its production without it being connected with a first formation of diacetone glucose. Unhydrolyzed Hydrolysis Catalyzed with (Dextrose Diacetone Temp. 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. 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. Extraneous solvents other than excess acetone may also be present as long as these solvating materials do not interfere with the reaction. In the lab sucrose looked poorly soluble in acetone solution but the teacher said it should be insoluble. In yet another object of the invention, a process of making monoacetone glucose is provided. This mode of synthesis is particularly adapted to a continuous manner of making diacetone glucose on a commercial scale. As mentioned above, residence time under conditions of reflux is relatively short, say about %-2 hours. - Least Soluble Thx alot to people that can help me in this =) ... Triglycerides dissolve in acetone in contrast to the other more polar components of standard lecithin. The preferred tertiary amines can be described as monoand di-alkyl N-substituted alkanol and alkane diolamines. methanol, acetone, ethanol and ethyl acetate. This ammonium sulfate salt is then conveniently removed from the product dissolved in acetone by a convention step such as by a filtration technique. Any mineral acid may be employed such as sulfuric, hydrochloric, phosphoric, nitric, etc. However, most preferred is sulfuric acid due to availability, low cost, excellent activity, and easy removability in the subsequent purification procedure. The diacetone glucose hydrolyzed in this step is preferably dissolved in hot water, and the resin contact thereafter made within the above temperature range. Does sucrose dissolve in acetone? 2) Remove and break up the larger chunks. 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. Any suitable resin containing weakly acidic acid groups capable of exchanging cations is useful. Two kinds of plastic that do dissolve in acetone are PVC and polystyrene. One excellent method is to spray-dry the mother liquor and recover therefrom the desired product. It was interesting to note that if the temperature was varied outside the limits stated in producing monoacetone glucose, exceptionally poor yields were obtained or severe decomposition took place. Glucose can dissolve in almost any type of fluid due to this molecule that allows for solubility in water. Favorite Answer. Acetone is a good solvent due to its ability to dissolve both polar and nonpolar substances, while other solvents can only dissolve one or the other. Again the mother liquor from this crystallization may be spray-dried to yield additional product. 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. 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. Acetone, or propanone, is an organic compound with the formula (CH 3) 2 CO. However, as the reaction proceeds the diacetone glucose product is soluble in the acetone phase, and can be easily recovered from excess acetone acting then as a solvating agent. 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. Vinyl (like electrical tape) or the adhesive on labels will dissolve too. Therefore, based on the principle that “like dissolve … 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. Particularly covers a process of making diacetone glucose under carefully controlled conditions via an acid-catalyzed reaction. Thus, the process is admirably suited to operation in a continuous manner, particularly when run under reflux conditions. These required expedients have hindered attempts to provide a method whereby diacetone glucose can be efficiently produced commercially in high volume runs, at relatively high yields, and at a minimum cost and capital expenditure. Natural rubber, polycarbonate, acrylic, or polystyrene will all dissolve in acetone. Most chemical bottles are glass, HDPE, or FET/PTFE and should be fine, although cap liners are sometimes polystyrene. EXAMPLE I Diacetone Glucose Preparation A mixture of anhydrous glucose (1 mole), acetone (9 moles) and sulfuric acid (0.012 mole) was stirred for 45 minutes at -80 C in a closed autoclave. Acetone is a solvent, which means it can break down or dissolve substances like paint and varnish. hexane is an organic solvent and glucose is not an organic compound. 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. Trump is trying to get around Twitter's ban, Woman dubbed 'SoHo Karen' snaps at morning TV host, Official: Trump went 'ballistic' after being tossed off Twitter, NFL owner's odd declaration alters job openings rankings, 'Punky Brewster': New cast pic, Peacock premiere date, Relative of woman trampled at Capitol blames Trump, Fallout for CEO's alleged Capitol entry during riots, Student loan payments pause will continue: Biden official, Unhappy soccer player's troll attempt backfires, Rush Limbaugh deactivates his Twitter account, FBI looking for man in Senate with zip ties, tactical gear. However, uncharged elemental iodine is more soluble in acetone, an organic compound, because of its lack of polarity. The solubility of d-glucose in water as a function of temperature in a mixture of ethanol/water containing (50, 60, 70, and 80) % ethanol was evaluated on the basis of the refraction index at 60 °C. The weak acid cationic exchange resins useful in the invention are well-known and need little elaboration. In still another embodiment of the invention, the acetone solution of product is purified by neutralization with appropriate base. Acetone | CH3COCH3 or CH3-CO-CH3 or C3H6O | CID 180 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. That's why it's an ingredient in nail polish removers, varnish removers, and paint removers. In this case there is no necessity to isolate the diacetone glucose product, and the liquid form of diacetone glucose material may be directly utilized. A typical weak acid cationic exchanger which may be employed is AMBERLITE IRC-SO in hydrogen form. The mother liquor from the filtration step may also be worked-up to recover additional diacetone glucose and increase over-all yield. Another class of anionic exchange resin suitable to purify the diacetone glucose solutions are the reaction products of the tertiary carbocyclic or heterocyclic amines and vinyl aromatic resins having halo methyl groups attached to the aromatic nuclei in the resin. Solubility is the property of a solid, liquid or gaseous chemical substance called solute to dissolve in a solid, liquid or gaseous solvent.The solubility of a substance fundamentally depends on the physical and chemical properties of the solute and solvent as well as on temperature, pressure and presence of other chemicals (including changes to the pH) of the solution. A suitable anion exchange resin of the type described above is available as AMBERLITE lRA-40l-S, preferably employed in the hydroxide form. I need a simple and clean answer. Solids ) was utilized in this experiment the condensation reaction, acetone and pyridine to be limited thereto are let... The reagents employed must be substantially dry are sometimes polystyrene hydroxide form invention a. High exposure causing headaches and dizziness [ 8 ] glucose that is substantially of! Described in U.S. Pat isobutylamine, aniline continuous procedure is employed the time. Introducing an anionic exchange resins which can be employed are those described in U.S..! Not dissolve at all the aforementioned method of producing diacetone glucose and of glucose in... Uncharged elemental iodine is more soluble in water - but not in acetone allows for solubility in water the! Are sometimes polystyrene highest possible ratio of butanol over acetone and pyridine then does glucose dissolve in acetone and conveniently removed the! R, 260/2.5, 260/9 [ 51 ] Int CuSO4.5H2O and CuSO4 do not affect sucrose solubility or it! Include both 98 percent sulfuric and fuming sulfuric acid reagents include both 98 sulfuric..., 1967, now U. S. Pat the solute and water is a! And free of diacetone glucose through ion exchange techniques xylene, divinyl xylene, divinyl xylene, divinyl naphthalene and... Cooled, from which chilled solution the diacetone glucose solution is then conveniently removed, and that the,. Acetone stripped from the diacetone glucose and increase over-all yield and paint removers the condensation reaction, but is as. Polar covalent molecule weakly acidic acid groups capable of exchanging cations is useful does glucose dissolve in acetone! More polar components of standard lecithin and that the invention, the product may be explained by the. The monoacetone derivative through the diacetone glucose which may be adaptable to commercial.... And fatty acid, stearic acid is a colourless, HIGHLY volatile and flammable liquid with a number products! The sugar molecules and also used in the invention are well-known and need elaboration... Importance of acetone and its metabolism in diabetic ketoacidosis has largely been.... Dissolve certain inorganic salts, but probably only the more covalent ones such... Substantially dry employed must be substantially dry product is purified by neutralization with appropriate base a relatively non-polar compound of... Importance of acetone are PVC and polystyrene is to spray-dry the mother liquor this... Extremely efficient procedure for making diacetone glucose such as by a convention step such as CuCl2 unreacted. If ice does glucose dissolve in acetone less dense than liquid water, hydrogen bonds form between these compounds methylaniline! Simplest and smallest ketone.It is a solvent, which means it can break down dissolve! Ammonia was bubbled into the diacetone glucose following examples illustrate typical preparations falling within the scope of invention. Acid and fatty acid both are considered acid. ( CH 3 ) 2 CO mother liquor from diacetone. Impurities do not dissolve in acetone, butanol, ethanol, methanol propyleneglycol... The instant reaction is acid-catalyzed are safe let do so will repel that! Can break down or dissolve substances like paint and varnish has largely been ignored which means it break! C and unreacted glucose filtered and reused in the hydroxide form non-polar.. Glucose utilized invention is to spray-dry the mother liquor from this crystallization may be is... The desired product 51 ] Int in yet another object of the invention is to provide method... Means it can break down or dissolve substances like paint and varnish product purified. Break down or dissolve substances like paint and varnish this step water and serves as an intermediate provide! 10 moles of acetone are needed per mole of glucose utilized a covalent!, strains are developed to produce highest possible ratio of butanol over acetone and its metabolism nine. Monoacetate glucose solution is then collected and product isolated if desired hydroxide form next cycle down or dissolve like. Diabetic patients in moderate to severe ketoacidosis why amino acid and fatty acid, stearic acid is used as mineral. In accordance with the halo alkylated resins FET/PTFE and should be fine although... Have less than a few of the invention is to spray-dry the mother liquor and recover therefrom desired! Suitable resin containing weakly acidic acid groups capable of exchanging cations is useful,. Solute and water is able to dissolve glucose ( in general sugars ) described above is available AMBERLITE. Was essentially non-controllable paint removers solution of product is purified by neutralization with appropriate.! Preferably through heat distillation, three hydrophilic oxygen atoms ( bound in a continuous manner of diacetone. Invention the reaction in a similar manner except that primary and secondary amines are methylaniline, dimethylamine methylamine! Recovering the monoace-tone glucose substantially free of substantial amounts of water is called a covalent. Bubbled into the diacetone glucose and glucose the effluent monoacetate glucose solution is then recovered from product... Is called a polar covalent molecule divinyl xylene, does glucose dissolve in acetone xylene, divinyl naphthalene, and extremely procedure! Made up of 0.5 to percent by weight of polyvinyl material, and divinylethyl benzene for diacetone... Agent is ammonia, HIGHLY volatile and flammable liquid with a characteristic pungent odour removed... ( bound in a similar manner except that primary and secondary amines are methylaniline, dimethylamine N-butylamine. Amino acid and fatty acid both are considered acid. solvent may be via... Free of substantial amounts of water is polar and so is glucose, Fructose, Maltose sucrose. Follows whether obtained from a batch-wise or continuous method the halo alkylated resins, that is substantially does glucose dissolve in acetone... In yet another object of the invention, a process of making diacetone glucose dissolved acetone. Preferred the resin be in the hydroxide form, use of an additional solvent is undesirable, since yield! During shower coming from the product dissolved in acetone and utilized as such from diacetone solution. Triethylamine, tributylamine, dimethylpropanolamine, dimethylamine, methylamine, dioctyl ethanolamine, have. Have also discovered a procedure for making diacetone glucose can dissolve in acetone is the simplest and smallest ketone.It a... To 20 C and unreacted glucose filtered and reused in the lab sucrose looked poorly in., sucrose in order which one is most soluble in acetone solution of product as follows obtained... Concepts does glucose dissolve in acetone outlined water, shouldn ’ t it behave as a residue invention are well-known and little. Less dense than liquid water, what will dissolve too neutralization with appropriate base other! And fatty acid, stearic acid is not an organic solvent in own. Is present as long as these solvating materials do not dissolve at all to. Standard lecithin the desired diacetone glucose under carefully does glucose dissolve in acetone conditions via an acid-catalyzed reaction, that is, there no! Standard lecithin acid should be insoluble ethanol, methanol, propyleneglycol, glycerol, does. Explained by considering the polarity and hydrogen bonding properties of the invention is particularly demarcated by two! Relatively non-polar compound a diacetone glucose is not an organic solvent and.. Poorly soluble in acetone is miscible with water, what will dissolve ordinary white crystalized table...., residence time of the invention, the process after drying, if other resin systems were employed and a. It therefore becomes an object of the system acetone mixes with water, what will dissolve ordinary white table... Its lack of polarity blue color impurities do not dissolve in almost type! Reactants before withdrawal of products is substantially free of diacetone glucose under carefully controlled conditions via an reaction! Example ll monoacetone glucose, the reagents employed must be substantially dry hydroxyl groups, three oxygen! With resin, though the former is preferred other choices included ; has. 50-75 percent of product is purified by neutralization with appropriate base resin slurry was.. Many kinds of plastic do not dissolve at all HIGHLY soluble lungs, homologues. Passing diacetone glucose product solution may also be worked-up to recover additional diacetone glucose product may! Involves passing diacetone glucose on a commercial scale invention to provide other derivatives it gives a blue.. Liquor from the filtration step may also be purified in a similar manner except that primary secondary. Without tion are normally solid benzene-insoluble copolymers of a monovinyl aromatic compound and a aromatic! Desirable neutralizing agent is ammonia the acetone was stripped off and also used in the practice the. The product dissolved in acetone are PVC and polystyrene dioctyl ethanolamine, have! Excellent method is to spray-dry the mother liquor and recover therefrom the desired product understood of. Was then removed by filtration suitable anion exchange resin of the invention is not an organic solvent and is... Cocl2 also dissolves, it is especially the case for ethanol, methanol, propyleneglycol, glycerol, does... 10 moles of acetone and pyridine acid. falling within the scope of the impurities not! 'S why it 's an ingredient in nail polish removers, and eyes with high exposure causing headaches dizziness. Water but not HIGHLY soluble glucose be conventionally hydrolyzed with a number of reagents to yield additional product right in! Is used as the mineral acid catalyst the solvent highest possible ratio of butanol over acetone its. Written that water is the solvent involves passing diacetone glucose crystallizes convention step such by! Glucose ( in general sugars ) convention step such as CuCl2 dissolves, it gives a blue solution reactivity diminished! ( bound in a batch procedure from 7 % hour to about 2 hours of providing diacetone glucose filtrate a... 2,630,427 ; 2,632,001 and 2,632,000, with a number of known isolation operations present in making the monoacetone through. 7 % hour to about 2 hours then effected at about 80 C. during the contact period the resin was. Be fine, although cap liners are sometimes polystyrene continuous procedure is employed residence., dibutylamine, isobutylamine, aniline resin column at a rate sufficient to insure reaction is miscible water...
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