US1895414A - Separation of ketoses from mixtures - Google Patents
Separation of ketoses from mixtures Download PDFInfo
- Publication number
- US1895414A US1895414A US526569A US52656931A US1895414A US 1895414 A US1895414 A US 1895414A US 526569 A US526569 A US 526569A US 52656931 A US52656931 A US 52656931A US 1895414 A US1895414 A US 1895414A
- Authority
- US
- United States
- Prior art keywords
- ketoses
- separation
- mixtures
- grams
- filtrate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 208000007976 Ketosis Diseases 0.000 title description 15
- 150000002584 ketoses Chemical class 0.000 title description 15
- 239000000203 mixture Substances 0.000 title description 14
- 238000000926 separation method Methods 0.000 title description 8
- 238000000034 method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 10
- 150000001323 aldoses Chemical class 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 8
- 235000011941 Tilia x europaea Nutrition 0.000 description 8
- 239000004571 lime Substances 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 230000003472 neutralizing effect Effects 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 229960005069 calcium Drugs 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000003792 electrolyte Substances 0.000 description 4
- 150000004679 hydroxides Chemical class 0.000 description 4
- 229960004903 invert sugar Drugs 0.000 description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- 239000005715 Fructose Substances 0.000 description 3
- 229930091371 Fructose Natural products 0.000 description 3
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000005868 electrolysis reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000004227 calcium gluconate Substances 0.000 description 1
- 229960004494 calcium gluconate Drugs 0.000 description 1
- 235000013927 calcium gluconate Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- NEEHYRZPVYRGPP-UHFFFAOYSA-L calcium;2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Ca+2].OCC(O)C(O)C(O)C(O)C([O-])=O.OCC(O)C(O)C(O)C(O)C([O-])=O NEEHYRZPVYRGPP-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical class BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- GEOVEUCEIQCBKH-UHFFFAOYSA-N hypoiodous acid Chemical class IO GEOVEUCEIQCBKH-UHFFFAOYSA-N 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K3/00—Invert sugar; Separation of glucose or fructose from invert sugar
Definitions
- This application relates to an electrolytic process for the separation of ketoses from mixtures of aldoses and ketoses, and is a continuation in part of U. S. Serial No. 515,648,
- this oxidation can also be accomplished with a" hypobromites or hypoiodites, but it is then pensive reagent, and the recovery of the ketose is rendered diiiicult by the large amount of bromide or iodide produced in the reaction.
- the oxidation can also be accomplished with hypochlorite to which iodides or bromides have been added(U. 5. Patents Nos. 1,648,368 and 1,70S,755Arthur Stoll and Walter Kussmahl). This method, however, yields the desired products mixed with great quantities of alkali or alkaline earth salts,
- Naturally occurring mixtures such as honey, plant juices and the like can be used as can also inverted sucrose and any synthetically pre ared mixture.
- the example below inclu es as a preliminary step the preparation of an invert sugar but it should be understood that the invention is not confined to a sugar mixture thus prepared.
- a soluble bromide or iodide is added to the sugar mixture and a substance capable of neutralizing the mono carboxylic acid as it is formed, is added. ll have found that the hydroxides, carbonates and bicarbonates of the alkalies and alkaline earth metals are satisfactory for their purpose. It is then electrolyzed, using insoluble anodes.
- the cathode may be of iron, copper, lead, aluminum, nickel or almost any of the common metals. Enough agitation is necessary to m keep some of the base in suspension.
- electrolysis I is stopped, excess base is removed by neutralization, the solution is concentrated, if necessary, and the sparingly soluble salt of the monocarboxylic acid crystallizes out.
- Ezmmple 1 ams of sucrose were dis solved in 170 cc. 0 water; 10 grams of sulphuric acid in 50 cc. of water were added and heated to C. for 30 minutes. lit was then neutralized with lime, filtered and washed. Analysis showed that the filtrate contains 54 grams of invert sugar. To this were added 2 grams of potassium iodide and 5.5 grams of lime. This electrolyte was placed in an iron cup, which s rved as a cathode, and a rotating graphite anode was placed in the center of it.
- the electrolyte was evaporated to 100 cc. and allowed to stand for forty-eight hours. A dense precipitate of calcium gluconate was formed, which was centrifuged off and washed. The filtrate and washings were concentrated to cc., and this was added slowly to 6 grams of lime in 40 cc. of water, the temperature being kept at 2 C. during the addition. The sparingly soluble calcium fructosate crystallized out. This was filtered ofiand washed. It was then suspended in water and decomposed with carbon dioxide. The calcium carbonate was filtered oif, and the filtrate concentrated and precipitated with alcohol, the fructosebeing removed by filtration. The filtrate was then evaporated for recovery of the alcohol.
- separation of ketoses from mixtures of aldoses and ketoses thostep which comprises electrolyzing the mixture in the presence'of a substance capable of neutralizing the monocarboxylic acid formed and in the presence of a. soluble salt
- This electrolyte was containing a halogen of higher molecular weight than chlorine.
- a step as described in claim 3'in which the neutralizing substance is one of the group consisting of hydroxides, carbonates and bicarbonates of the alkalies and alkaline earth metals.
- step 7 comprising electrolyzing the mixture in the presence of one of the group consisting of hydroxides, carbonates and bicarbonates of the alkalies and alkaline earth metals and in the presence of a salt containing a halogen of higherhiolecular weight than chlorine.
Description
Patented Jan. 24, 1933 UNITED STATES PATENT? oFFica EDWARD L HELWIG, F BRISTOL, PENNSYLVANIA, ASSIGNOR T0 36H!!! & HAAS COMPANY, OF PHILADELPHIA, PENNSYLVANIA snranarron or xnrosas rnom mrxronus lo Drawing.
This application relates to an electrolytic process for the separation of ketoses from mixtures of aldoses and ketoses, and is a continuation in part of U. S. Serial No. 515,648,
February 13th, 1931.
The separation of mixtures of aldoses and ketos'es has always been a diflicult problem from a technical standpoint, due to the similarity of the properties of these sugars. A
13 number of recrystallizations have been necessary in order to get a clean separation. The new method which 1 herein describe has overcome this cumbersome separation of these two classes of sugars. The electric current 15 oxidizes the aldoses almost quantitatively to their corresponding monocarboxylic acids without affecting the ketoses. (See my copending application #427,065 filed February 8th, 1930, Electrolytic oxidation of aldoses 29 etc) The monocarboxylic acids, being entirely difi'erent from the unoxidized ketosesugars, are easily separated. It is true that this oxidation can also be accomplished with a" hypobromites or hypoiodites, but it is then pensive reagent, and the recovery of the ketose is rendered diiiicult by the large amount of bromide or iodide produced in the reaction. The oxidation can also be accomplished with hypochlorite to which iodides or bromides have been added(U. 5. Patents Nos. 1,648,368 and 1,70S,755Arthur Stoll and Walter Kussmahl). This method, however, yields the desired products mixed with great quantities of alkali or alkaline earth salts,
which not onl render the isolationtof the ketose diiiicult hut greatly complicate the recovery of the expensive bromide or iodine. The electrolytic process, herein described, si-
multaneously produces the monocarhoxylic acids of the aldoses in such a form that they are easily recoverable, and yields the ketose associate with a small amount of bromide or iodide, from which it can be readily separated. After the ketose is removed from the solution, the residual liquor is evaporated, ignited and the expensive halogen is recovered almost quantitatively by leaching the ash.
The source of the sugar mixturesis imma- J necessary to use a large quantity of an ex Application filed March 30, 1931. Serial No. 526,569.
terial for the purposes of this invention. Naturally occurring mixtures such as honey, plant juices and the like can be used as can also inverted sucrose and any synthetically pre ared mixture. The example below inclu es as a preliminary step the preparation of an invert sugar but it should be understood that the invention is not confined to a sugar mixture thus prepared. A soluble bromide or iodide is added to the sugar mixture and a substance capable of neutralizing the mono carboxylic acid as it is formed, is added. ll have found that the hydroxides, carbonates and bicarbonates of the alkalies and alkaline earth metals are satisfactory for their purpose. It is then electrolyzed, using insoluble anodes. No diaphragm is required, and the cathode may be of iron, copper, lead, aluminum, nickel or almost any of the common metals. Enough agitation is necessary to m keep some of the base in suspension. When suihcient current has passed through the cell 7 to oxidize all the aldose present, electrolysis I is stopped, excess base is removed by neutralization, the solution is concentrated, if necessary, and the sparingly soluble salt of the monocarboxylic acid crystallizes out.
The following examples will serve to illustrate the nature of my invention, but it is not limited to these special cases, nor as to temperature, concentration, sequence of operations or other conditions.
Ezmmple 1. ams of sucrose were dis solved in 170 cc. 0 water; 10 grams of sulphuric acid in 50 cc. of water were added and heated to C. for 30 minutes. lit was then neutralized with lime, filtered and washed. Analysis showed that the filtrate contains 54 grams of invert sugar. To this were added 2 grams of potassium iodide and 5.5 grams of lime. This electrolyte was placed in an iron cup, which s rved as a cathode, and a rotating graphite anode was placed in the center of it.
It was electrolyzed at a temperature of 10 C. with a current density of 15 amperes per square foot. When 7.9 ampere hours had passed through the cell, electrolysis was stopped. The excess lime was neutralized with sulphuric acid, and the electrolyte was evaporatedat cc. and allowed to stand for no grams of invert sugar.
- 1. Inthe process for the forty-eight hours. A dense precipitate of calcium g'luconate was formed, which was centrifuged off and washed. The filtrate and washin s were concentrated to 60 cc., and this was added slowing to 6 grams of lime in 40 cc. of water, the temperature being kept at 2 C. during the addition. The sparingly soluble calcium fructosate crystallized out. This was filtered OE and washed. It was then suspended in water and decomposed with carbon dioxide. The calcium carbonate was filtered off, and the filtrate concentrated and precipitated with alcohol, the fructose be-. ing removed by filtration. The filtrate was then evaporated for recovery of-the alcohol. The filtrate from the calcium fructosate was evaporated, ignited and leached with water for recovery of the sodium bromide.
Ewwmple Q.60 rams of sucrose were dissolved in 170 cc. 0? water; 10 grams of sulhuric acid in cc. of water were added and eated to 70 C. for 30 minutes. It was then neutralized with lime, filtered and washed. Analysis showed that the filtrate contained 54 To this were added 2 grams of potassium iodide and 6.5 grams of calcium carbonate. placed in an iron cup, which served as a cathode, and a rotating graphite anode was placed in the center of it. It was electrolyzed at a temperature of 10 C. with a current density of 15 amperes per square foot. When 7 .9 ampere hours had passed through the cell, electrolysis was stopped. The electrolyte was evaporated to 100 cc. and allowed to stand for forty-eight hours. A dense precipitate of calcium gluconate was formed, which was centrifuged off and washed. The filtrate and washings were concentrated to cc., and this was added slowly to 6 grams of lime in 40 cc. of water, the temperature being kept at 2 C. during the addition. The sparingly soluble calcium fructosate crystallized out. This was filtered ofiand washed. It was then suspended in water and decomposed with carbon dioxide. The calcium carbonate was filtered oif, and the filtrate concentrated and precipitated with alcohol, the fructosebeing removed by filtration. The filtrate was then evaporated for recovery of the alcohol. The filtrate from the calcium fructosate was evaporated, ignited and leached with water for recovery of the sodium bromide. It will be recognized by one versed in the art that wide variations may be made in the above 8 ifications within the irit of the invention, the sec of which is 'mited only. by the claims whic follow.
What I claim as new is:
separation of ketoses from mixtures of aldoses and ketoses thostep which comprises electrolyzing the mixture in the presence'of a substance capable of neutralizing the monocarboxylic acid formed and in the presence of a. soluble salt This electrolyte was containing a halogen of higher molecular weight than chlorine.
2. Process as in claim 1 in whichthe rocess is carried out with an insoluble anod ei.
3. In the process of separating ketoses from mixtures of aldoses and ketoses the step of electrolyzing the mixture with an insoluble anode in the presence of a substance capable of neutralizing the monocarboxylic acid formed and in the resence of a salt containing a halogen of higher molecular weight than chlorine.
4. A step as described in claim 3 in which v lime is the neutralizing substance.
5. A step as described in claim 3 in which calcium carbonate is the neutralizing substance.
. 6. A step as described in claim 3'in which the neutralizing substance is one of the group consisting of hydroxides, carbonates and bicarbonates of the alkalies and alkaline earth metals.
7. In the process for the separation of fructose from the constituents of invert sugar the step comprising electrolyzing the mixture in the presence of one of the group consisting of hydroxides, carbonates and bicarbonates of the alkalies and alkaline earth metals and in the presence of a salt containing a halogen of higherhiolecular weight than chlorine.
8. The process for the separation of ketose H ing lime and filtering off the calcium salt thus formed, suspending it in water and treating it with carbon dioxide for liberation of the ketose and then working it up by known methods.
. 9. In the process for the simultaneous 1S0- lation of ketoses and oxidation of aldoses,
the step which comprises electrolyzing the mixture in the presence of one of the group consisting of hydroxides, carbonates, andbicarbonates of the alkalies and alkali earth metals and in the presence of a salt containing a halogen of higher molecular weight than chlorine.
10. In the proces for the simultaneous isolation of fructose and oxidation of glucose to gluconic acid, the step which comprises In testimony whereof I aflix my EDWARD L. HELWIG.
electrolyzing the mixture in the presence of .1
ydroxides,
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US526569A US1895414A (en) | 1931-03-30 | 1931-03-30 | Separation of ketoses from mixtures |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US526569A US1895414A (en) | 1931-03-30 | 1931-03-30 | Separation of ketoses from mixtures |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1895414A true US1895414A (en) | 1933-01-24 |
Family
ID=24097866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US526569A Expired - Lifetime US1895414A (en) | 1931-03-30 | 1931-03-30 | Separation of ketoses from mixtures |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1895414A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2563884A (en) * | 1947-05-24 | 1951-08-14 | Sugar Res Foundation Inc | Mercaptalation of sugar |
-
1931
- 1931-03-30 US US526569A patent/US1895414A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2563884A (en) * | 1947-05-24 | 1951-08-14 | Sugar Res Foundation Inc | Mercaptalation of sugar |
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