CA1272481A - Sucrosetricarboxylic acid, process for its preparation, and its use - Google Patents
Sucrosetricarboxylic acid, process for its preparation, and its useInfo
- Publication number
- CA1272481A CA1272481A CA000519880A CA519880A CA1272481A CA 1272481 A CA1272481 A CA 1272481A CA 000519880 A CA000519880 A CA 000519880A CA 519880 A CA519880 A CA 519880A CA 1272481 A CA1272481 A CA 1272481A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- carried out
- oxidation
- sucrosetricarboxylic
- catalyst
- 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 - Fee Related
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/221—Mono, di- or trisaccharides or derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/035—Organic compounds containing oxygen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
- C07H7/033—Uronic acids
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- General Preparation And Processing Of Foods (AREA)
- Steroid Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Abstract of the disclosure:
Sucrosetricarboxylic acid can be prepared by oxidizing sucrose with oxygen, if desired in a mixture with inert gases, by means of a more effective catalyst than platinum/
alumina.
The product can be used in washing agents or as a food additive.
Sucrosetricarboxylic acid can be prepared by oxidizing sucrose with oxygen, if desired in a mixture with inert gases, by means of a more effective catalyst than platinum/
alumina.
The product can be used in washing agents or as a food additive.
Description
HOECHST AKTIENGESELLSCHAFT HOE 85tF 217 Dr.KH/mu Sucrosetricarboxylic acid, process for its preparation, and its use The present invention relates to sucrosetr;carboxylic acid and its sacondary products such as salts, lactones~
esters, amides and the like, to a process for preparing and uslng the same.
It is known that the catalytic ox;dation of carbohydratesl specifically that of the primary hydroxymethyl groups con-tained therein, proceeds slowly and in most cases non-uniformly. For instance, oligomeric carbohydrates such as --branched arabinoxylan from rye flour are oxidized in 4 days at 65C in only 4% to uronic acids. It is true that the oxidation of sucrose has also been mentioned, but state-ments about the ;solation of the reaction products were not mentioned at the time. It was merely stated that it ~as found in a subsequent total hydrolysis that the hydro-lyzate contained only small amounts of glucuronic acid.
The oxidation of sucrose with a platinum-alumina catalyst and oxygen has also been previously described (German Patent 886,305, Example 3 and the corresponding US Patent
esters, amides and the like, to a process for preparing and uslng the same.
It is known that the catalytic ox;dation of carbohydratesl specifically that of the primary hydroxymethyl groups con-tained therein, proceeds slowly and in most cases non-uniformly. For instance, oligomeric carbohydrates such as --branched arabinoxylan from rye flour are oxidized in 4 days at 65C in only 4% to uronic acids. It is true that the oxidation of sucrose has also been mentioned, but state-ments about the ;solation of the reaction products were not mentioned at the time. It was merely stated that it ~as found in a subsequent total hydrolysis that the hydro-lyzate contained only small amounts of glucuronic acid.
The oxidation of sucrose with a platinum-alumina catalyst and oxygen has also been previously described (German Patent 886,305, Example 3 and the corresponding US Patent
2,845,439~ Example 4). After a 6-hour treatment this oxidation gave only 60% of the theoretically expected yield of the corresponding glucuronic acid derivative. However, the isolation of this compound is not described.
The invention provides, then, sucrosetricarboxylic acid (i.e. (~-D-arabinofuranaric-2-hexulosyl)-~-D-glucopyrano-sid~ronic acid) of the formula COOH COOH
,o ~OOH
HO
~ OH
~ '7~
The invention further provides a process for preparing sucrosetricarboxylic acid, ~hich comprises o~idizing suc-rose with oxygen, if desired in a mixture with inert gases, for example in the fsrm of air, by means of a signif;cantly more effect;ve catalyst than plat;num/alumina. Su;table catalysts are those of platinum metals, such as paLladium, but in particular platinum itself, on activated carbon, in part;cular the more active types. These generally contain 5 - 10% by ~eight of metaL, in particular platinum. In addit-ion to a distinct increase in the rate of oxidation, an ;n-creased selectivity of the oxidation bet~een primary and secondary hydroxyl groups of the carbohydrates, in particu-lar of nonreducing carbohydrates, is achieved. Preferably the oxidation is carried out by treating ~he solid catalyst ~n an aqueous reaction medium ~ith gaseous oxygen, i.e. in a three-phase reaction. Th;s three-phase reaction is carried out for example in a bubble column reactor ~hich can be operated not only batch~ise but also continuously. In preferred embodi-ments, highly concentrated oxygen is used and the reaction solution is recycled, ~hich ~acilitates setting, and keeping constant, the pH. It is within the capacity of the skilled ~orker to set the reaction solution to a selected and suit-able reaction temperature and to optimize the concentration ratio of substrate/catalyst or substrate/oxygen.
The process according to the invention is generally carried out at 30C to the boil, preferably at 50 to 95, in particu-lar 60 to 90C. In general, atmospheric pressure is em-ployed, but it is also possible to employ superatmospheric pressure, ~hich is a way of increasing the supply of oxygen and/or the reaction temperature. In the process according to the invention9 maintaining certain sucrose concentrations is part;cularly advantageous; concentrations below 5~ by weight easily give rise to an over-oxidation and above 20~ by weight only to comparatively low conversions under atmospheric pressure. In general, pH values of 5 to 9, preferably 6 to 8, are used. The course of the reaction can be monitored by ~B
`, ~ ..
The invention provides, then, sucrosetricarboxylic acid (i.e. (~-D-arabinofuranaric-2-hexulosyl)-~-D-glucopyrano-sid~ronic acid) of the formula COOH COOH
,o ~OOH
HO
~ OH
~ '7~
The invention further provides a process for preparing sucrosetricarboxylic acid, ~hich comprises o~idizing suc-rose with oxygen, if desired in a mixture with inert gases, for example in the fsrm of air, by means of a signif;cantly more effect;ve catalyst than plat;num/alumina. Su;table catalysts are those of platinum metals, such as paLladium, but in particular platinum itself, on activated carbon, in part;cular the more active types. These generally contain 5 - 10% by ~eight of metaL, in particular platinum. In addit-ion to a distinct increase in the rate of oxidation, an ;n-creased selectivity of the oxidation bet~een primary and secondary hydroxyl groups of the carbohydrates, in particu-lar of nonreducing carbohydrates, is achieved. Preferably the oxidation is carried out by treating ~he solid catalyst ~n an aqueous reaction medium ~ith gaseous oxygen, i.e. in a three-phase reaction. Th;s three-phase reaction is carried out for example in a bubble column reactor ~hich can be operated not only batch~ise but also continuously. In preferred embodi-ments, highly concentrated oxygen is used and the reaction solution is recycled, ~hich ~acilitates setting, and keeping constant, the pH. It is within the capacity of the skilled ~orker to set the reaction solution to a selected and suit-able reaction temperature and to optimize the concentration ratio of substrate/catalyst or substrate/oxygen.
The process according to the invention is generally carried out at 30C to the boil, preferably at 50 to 95, in particu-lar 60 to 90C. In general, atmospheric pressure is em-ployed, but it is also possible to employ superatmospheric pressure, ~hich is a way of increasing the supply of oxygen and/or the reaction temperature. In the process according to the invention9 maintaining certain sucrose concentrations is part;cularly advantageous; concentrations below 5~ by weight easily give rise to an over-oxidation and above 20~ by weight only to comparatively low conversions under atmospheric pressure. In general, pH values of 5 to 9, preferably 6 to 8, are used. The course of the reaction can be monitored by ~B
`, ~ ..
- 3 -sampling~ for example by means of gas chromatography analysis of the derivatized, for example silylated, pro-ducts.
The sucrosetricarbo~ylic acid formed ;s generally obtained in a mixture with less oxidized intermediates, i.e. vari-ous monocarboxylic and/or dicarboxylic acids. The oxida-tion can be discontinued at as early a stage as a tri-carboxylic content of at least 20%. However, the oxid-ation is generally cont;nued until at least 30 or 40 andpreferably more than 60 or 70% o~F sucrosetricarboxylic acid has been Formed. This sucrosetricarboxylic acid can be concentrated and isolated out of the reaction mixture in a convent;onal manner.
The process according to the invention can be carried out, for example, in a jacketed reactor which holds the sus-pension of the catalyst in the aqueous medium and wh;ch conta;ns at the bottom a frit or another correspondingly Z0 suitable porous membrane and through which a gas stream, very finely divided by this separating membrane, flows from the underside. For economic and safety reasons, the oxygen is expediently passed through the reaction medium at such a rate that the catalytically activated oxygen is just con-sumed at the upper end of the bubble column. To improvethe degree oF mixing and to prolong the time of exposure to the oxygen, it can be advantageous to stir the reaction mixture.
On account of its chemical structure or structural ele-ments, the sucrosetricarboxylic acid formed is suitable as such or in the form of its immediately obtainable reac-tion products, i.e. in particular mixtures with the inter-mediates, for applications in the field of complexing agents, for example analogously to gluconic acid and glucaric acid in washing agent formulations, as food additives, for example for the applications customary for citric acid, as a polyfunctional reactant (crosslinking) and also as a starting material for chemical reactions ~hydrophili~ing reagent).
8:~ -The process according to the invention has made it possible to carry out the oxidation of sucrose ;n such a way as to form the h;therto unknown sucrosetr;carboxylic acid.
Examples _ 1) In an externally heated, upright glass tube (dia-meter: 50 mm, length: 80 cm) having a frit bottom and, installed at a point slightly thereabove, a discharge means for the reaction mixture, a stream of oxygen (about 25 liters (S.T.P.)/h) flows upwardly through a solut;on of 1209 of sucrose ;n 1.2 l;ters of ~ater and also 60 9 of added platinum catalyst (5% of Pt/active carbon). The acids formed by the oxidation are wholly or partly converted ;n-to the sodium salts either by feeding in sod;um hydroxidesolut;on, ~ith the attendant Poss;b;l;ty of pH control, or by means of the correspond;ng molar amounts of ;nit;ally introduced sodium hydrogencarbonate. At a eemperature of 80C ;n the ox;dation and neutralizat;on and a pH of 6.5 held constant dur;ng both stages, the products have after s;lylation and according to gas chromatography analysis the follo~ing composit;ons as a function of the reaction time (see Table 1):
5 Table 1 Composition of oxidation products as a function of reaction time t;n percent) 6 h 12 h 1~ h . ~
Sucrose consumed - -Monocarboxylic ac;ds 20.9 5.2 1~5 30 (2 isomers) Dicarboxylic acids 38.9 39.6 2917 t2 isomers) Tricarboxylic acid I 5.1 22.3 35.3 The reaction solution ;s filtered to remove the catalyst, and the filtrate is concentrated in a thin film evaporator and freeze-dried. Y;eld 1û4 9 (86.7% by weight). The total acid content is 7.18 mEqtg (theoretical value for sucrosetricarboxylic acid 7.80 mEq/g).
To characterize the sucrosetricarboxylic acid (STA), the reaction mixture is converted by means of commerc;ally ava;Lable cation exchanger ;nto the free acids and freeze-dried after f;ltration. After complete acetylation w;th an excess of ace~ic anhydride and equimolar amounts of p-toluenesulfonic acid (20C, 20 h), the sirupy residue is chromatographed over silica gel (eluent: methylene chloride/
methanol 10:1 v.v.). The pentaacetylated sucrosetricarb-oxylic acid obtained last with polar eluent in the chromato-graphy is converted with catalytic amounts of sodiummethanolate in methanol into the trisodium salt.
1H-NMR (D20, 400 MHz): ~= 5.45 (d,H-1',J1 ,2 = 3.75 Hz~,
The sucrosetricarbo~ylic acid formed ;s generally obtained in a mixture with less oxidized intermediates, i.e. vari-ous monocarboxylic and/or dicarboxylic acids. The oxida-tion can be discontinued at as early a stage as a tri-carboxylic content of at least 20%. However, the oxid-ation is generally cont;nued until at least 30 or 40 andpreferably more than 60 or 70% o~F sucrosetricarboxylic acid has been Formed. This sucrosetricarboxylic acid can be concentrated and isolated out of the reaction mixture in a convent;onal manner.
The process according to the invention can be carried out, for example, in a jacketed reactor which holds the sus-pension of the catalyst in the aqueous medium and wh;ch conta;ns at the bottom a frit or another correspondingly Z0 suitable porous membrane and through which a gas stream, very finely divided by this separating membrane, flows from the underside. For economic and safety reasons, the oxygen is expediently passed through the reaction medium at such a rate that the catalytically activated oxygen is just con-sumed at the upper end of the bubble column. To improvethe degree oF mixing and to prolong the time of exposure to the oxygen, it can be advantageous to stir the reaction mixture.
On account of its chemical structure or structural ele-ments, the sucrosetricarboxylic acid formed is suitable as such or in the form of its immediately obtainable reac-tion products, i.e. in particular mixtures with the inter-mediates, for applications in the field of complexing agents, for example analogously to gluconic acid and glucaric acid in washing agent formulations, as food additives, for example for the applications customary for citric acid, as a polyfunctional reactant (crosslinking) and also as a starting material for chemical reactions ~hydrophili~ing reagent).
8:~ -The process according to the invention has made it possible to carry out the oxidation of sucrose ;n such a way as to form the h;therto unknown sucrosetr;carboxylic acid.
Examples _ 1) In an externally heated, upright glass tube (dia-meter: 50 mm, length: 80 cm) having a frit bottom and, installed at a point slightly thereabove, a discharge means for the reaction mixture, a stream of oxygen (about 25 liters (S.T.P.)/h) flows upwardly through a solut;on of 1209 of sucrose ;n 1.2 l;ters of ~ater and also 60 9 of added platinum catalyst (5% of Pt/active carbon). The acids formed by the oxidation are wholly or partly converted ;n-to the sodium salts either by feeding in sod;um hydroxidesolut;on, ~ith the attendant Poss;b;l;ty of pH control, or by means of the correspond;ng molar amounts of ;nit;ally introduced sodium hydrogencarbonate. At a eemperature of 80C ;n the ox;dation and neutralizat;on and a pH of 6.5 held constant dur;ng both stages, the products have after s;lylation and according to gas chromatography analysis the follo~ing composit;ons as a function of the reaction time (see Table 1):
5 Table 1 Composition of oxidation products as a function of reaction time t;n percent) 6 h 12 h 1~ h . ~
Sucrose consumed - -Monocarboxylic ac;ds 20.9 5.2 1~5 30 (2 isomers) Dicarboxylic acids 38.9 39.6 2917 t2 isomers) Tricarboxylic acid I 5.1 22.3 35.3 The reaction solution ;s filtered to remove the catalyst, and the filtrate is concentrated in a thin film evaporator and freeze-dried. Y;eld 1û4 9 (86.7% by weight). The total acid content is 7.18 mEqtg (theoretical value for sucrosetricarboxylic acid 7.80 mEq/g).
To characterize the sucrosetricarboxylic acid (STA), the reaction mixture is converted by means of commerc;ally ava;Lable cation exchanger ;nto the free acids and freeze-dried after f;ltration. After complete acetylation w;th an excess of ace~ic anhydride and equimolar amounts of p-toluenesulfonic acid (20C, 20 h), the sirupy residue is chromatographed over silica gel (eluent: methylene chloride/
methanol 10:1 v.v.). The pentaacetylated sucrosetricarb-oxylic acid obtained last with polar eluent in the chromato-graphy is converted with catalytic amounts of sodiummethanolate in methanol into the trisodium salt.
1H-NMR (D20, 400 MHz): ~= 5.45 (d,H-1',J1 ,2 = 3.75 Hz~,
4.23-4.12 (m, H-5',H-3,H-4,H-5), 3.82, (struct. t, H-3'), J3-,4-= 9.5 Hz, J2',3'= 9.8 Hz), 3.54 (dd, H-2', J1' 2~=
3.75 Hz, J2' 3~= 9-8 Hz), 3.4S (struct. t,H-4',13 4-=
J4 ,5~=9.5 Hz).
Z0 GC-MS (gas chromatography/mass spectroscopy) (after s;lyl-ation, chemical ionization ~ith isobutane) m/z = 961 (M~1-fragment of the 8-fold silylated compound, relative inten-sity about 0.1%).
FA~-MS (fast atom bombardment) (sodium salt used, glycerol as matrix) m/z = 451 (MH~, relative intensity 36X).
2) 9y the method of Example 1, 120 9 of sucrose, dis-solved in 1.2 liters of water, are oxidized at 60C and pH 7.5 in a stream of oxygen. Table 2 shows the composi-tions determined by GC analysis.
-- 6 ~
Table 2 Composition of oxidation products as a function of reaction t;me (in percent) 8 h 28 h 52 h 84 h _ _ . . . , .. . . _ _ Sucrose 1.1 - - -S Monocarboxylic acids 28.9 10.3 5.7 4.7 (2 ;somers) Dicarboxylic acids 35.8 36.1 27.3 23.0 (2 isomers) Oxalic acid 5.9 10.8 12.6 10.9 10 Tricarboxylic acid 1 4.6 20.7 32.7 40.9 Filtration to remove the catalyst and freeze-drying the filtrate leaves 93.8 9 (78.0% by weight).
3.75 Hz, J2' 3~= 9-8 Hz), 3.4S (struct. t,H-4',13 4-=
J4 ,5~=9.5 Hz).
Z0 GC-MS (gas chromatography/mass spectroscopy) (after s;lyl-ation, chemical ionization ~ith isobutane) m/z = 961 (M~1-fragment of the 8-fold silylated compound, relative inten-sity about 0.1%).
FA~-MS (fast atom bombardment) (sodium salt used, glycerol as matrix) m/z = 451 (MH~, relative intensity 36X).
2) 9y the method of Example 1, 120 9 of sucrose, dis-solved in 1.2 liters of water, are oxidized at 60C and pH 7.5 in a stream of oxygen. Table 2 shows the composi-tions determined by GC analysis.
-- 6 ~
Table 2 Composition of oxidation products as a function of reaction t;me (in percent) 8 h 28 h 52 h 84 h _ _ . . . , .. . . _ _ Sucrose 1.1 - - -S Monocarboxylic acids 28.9 10.3 5.7 4.7 (2 ;somers) Dicarboxylic acids 35.8 36.1 27.3 23.0 (2 isomers) Oxalic acid 5.9 10.8 12.6 10.9 10 Tricarboxylic acid 1 4.6 20.7 32.7 40.9 Filtration to remove the catalyst and freeze-drying the filtrate leaves 93.8 9 (78.0% by weight).
Claims (25)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. Sucrosetricarboxylic acid of the formula and salts thereof.
2. A sodium salt of the sucrosetricarboxylic acid of the formula
3. A process for preparing sucrosetricarboxylic acid, which comprises oxidizing sucrose with oxygen, if desired in a mixture with inert gases, by means of a more effective catalyst than platinum/alumina.
4. The process as claimed in claim 3, wherein the reaction is carried out by treating solid catalyst in an aqueous reaction medium with gaseous oxygen.
5. The process as claimed in claim 3, wherein the reaction is carried out by treating solid catalyst in an aqueous reaction medium with gaseous highly concentrated oxygen.
6. The process as claimed in claim 3, 4 or 5, wherein the oxidation is carried out at 30°C to the boil.
7. The process as claimed in claim 3, 4 or 5, wherein the oxidation is carried out at 30°C to the boil under atmospheric pressure.
8. The process as claimed in claim 3, 4, or 5, wherein the oxidation is carried out at 50 to 95°C.
9. The process as claimed in claim 3, 4, or 5, wherein the oxidation is carried out at 50 to 95°C under atmospheric pressure.
10. The process as claimed in claim 3, 4, or 5, wherein the oxidation is carried out at 60 to 90°C.
11. The process as claimed in claim 3, 4, or 5, wherein the oxidation is carried out at 60 to 90°C under atmospheric pressure.
12. The process as claimed in claim 3, 4, or 5, wherein the liquid reaction medium contains 5 to 20% by weight of sucrose.
13. The process as claimed in claim 3, 4, or 5, wherein the oxidation is carried out at a pH of 5 to 9.
14. The process as claimed in claim 3, 4, or 5, wherein the oxidation is carried out at a pH of 6 to 8.
15. The process as claimed in claim 3, 4, or 5, wherein the catalyst is a platinum/activated carbon catalyst.
16. The process as claimed in claim 3, 4, or 5, wherein the catalyst contains 5 to 10% by weight of metal.
17. A process for preparing sucrosetricarboxylic acid, which comprises oxidizing sucrose in an aqueous reaction medium with oxygen at a pH in the range of from 6 to 8 and a temperature in the range of from 50°C to 95°C in the presence of a catalyst of a platinum metal on activated carbon, the aqueous reaction medium containing 5 to 20% by weight of sucrose.
18. The process as claimed in claim 17, wherein the catalyst contains 5 to 10% by weight of platinum.
19. The process as claimed in claim 3, 4 or 17, wherein the catalyst is palladium on activated carbon.
20. A method of using sucrosetricarboxylic said or its salts which comprises using an effective amount of said acid or its salts as an essential ingredient in washing agent formulations.
21. A method of using sucrosetricarboxylic acid or its physiologically acceptable salts which comprises using an effective amount of said acid or its salts as a food additive.
22. The use of sucrosetricarboxylic acid or its salts as an essential ingredient in washing agent formulations.
23. The use of sucrosetricarboxylic acid or its physiologically acceptable salts as a food additive.
24. The use of a sodium salt of the sucrosetricarboxylic acid as an essential ingredient in washing agent formulations.
25. The use of a sodium salt of the sucrosetricarboxylic acid as a food additive.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3535720.7 | 1985-10-07 | ||
| DE19853535720 DE3535720A1 (en) | 1985-10-07 | 1985-10-07 | SACCHAROSE TRICARBONIC ACID, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1272481A true CA1272481A (en) | 1990-08-07 |
Family
ID=6282946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000519880A Expired - Fee Related CA1272481A (en) | 1985-10-07 | 1986-10-06 | Sucrosetricarboxylic acid, process for its preparation, and its use |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0218150B1 (en) |
| JP (1) | JPH0778072B2 (en) |
| AT (1) | ATE59392T1 (en) |
| AU (1) | AU598480B2 (en) |
| CA (1) | CA1272481A (en) |
| DE (2) | DE3535720A1 (en) |
| DK (1) | DK165009C (en) |
| FI (1) | FI84073C (en) |
| IL (1) | IL80244A (en) |
| NZ (1) | NZ217806A (en) |
| ZA (1) | ZA867595B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3803465A1 (en) * | 1988-02-05 | 1989-08-17 | Huels Chemische Werke Ag | METHOD FOR PRODUCING OXIDIZED SUBSTITUTED SACCHARIDES |
| DE3900677A1 (en) * | 1989-01-12 | 1990-07-19 | Hoechst Ag | METHOD FOR PRODUCING A MIXTURE OF SACCHAROSE OXIDATION PRODUCTS |
| DE3916206A1 (en) * | 1989-05-18 | 1990-11-22 | Hoechst Ag | METHOD FOR PRODUCING 1-FLUOR-GLYCURONIC ACIDS AND THEIR SALTS, AND SUCH NEW 1-FLOUR-GLYCURONIC ACIDS AND THEIR SALTS |
| US5116961A (en) * | 1990-12-07 | 1992-05-26 | Hawaiian Sugar Planters' Association | 1',6,6'-trimethacryloyl-2,3,3',4,4'-penta-O-methylsucrose |
| DE4304756C1 (en) * | 1993-02-17 | 1994-09-08 | Hoechst Ag | Process for the preparation of salts, chiral, alpha-oxygen-functionalized carboxylic acids |
| DE19542287A1 (en) * | 1995-11-14 | 1997-05-15 | Suedzucker Ag | Process for the preparation of di- and higher-oxidized carboxylic acids of carbohydrates, carbohydrate derivatives or primary alcohols |
| DE10362249B4 (en) * | 2003-05-05 | 2014-05-15 | Südzucker AG Mannheim/Ochsenfurt | C1-selective oxidation of oligosaccharides and the use of a carbon-supported gold catalyst for this oxidation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2845439A (en) * | 1949-08-19 | 1958-07-29 | Corn Prod Refining Co | Preparation of uronic acids and derivatives thereof |
| GB8519416D0 (en) * | 1985-08-01 | 1985-09-04 | Unilever Plc | Oligosaccharides |
-
1985
- 1985-10-07 DE DE19853535720 patent/DE3535720A1/en not_active Withdrawn
-
1986
- 1986-09-25 EP EP86113217A patent/EP0218150B1/en not_active Expired - Lifetime
- 1986-09-25 DE DE8686113217T patent/DE3676617D1/en not_active Expired - Fee Related
- 1986-09-25 AT AT86113217T patent/ATE59392T1/en not_active IP Right Cessation
- 1986-10-03 FI FI864021A patent/FI84073C/en not_active IP Right Cessation
- 1986-10-06 ZA ZA867595A patent/ZA867595B/en unknown
- 1986-10-06 NZ NZ217806A patent/NZ217806A/en unknown
- 1986-10-06 JP JP61236381A patent/JPH0778072B2/en not_active Expired - Lifetime
- 1986-10-06 AU AU63532/86A patent/AU598480B2/en not_active Ceased
- 1986-10-06 DK DK476586A patent/DK165009C/en not_active IP Right Cessation
- 1986-10-06 CA CA000519880A patent/CA1272481A/en not_active Expired - Fee Related
- 1986-10-07 IL IL80244A patent/IL80244A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3535720A1 (en) | 1987-04-09 |
| JPH0778072B2 (en) | 1995-08-23 |
| FI864021A0 (en) | 1986-10-03 |
| EP0218150B1 (en) | 1990-12-27 |
| IL80244A (en) | 1990-08-31 |
| DK165009C (en) | 1993-02-22 |
| FI84073C (en) | 1991-10-10 |
| DE3676617D1 (en) | 1991-02-07 |
| NZ217806A (en) | 1988-10-28 |
| DK165009B (en) | 1992-09-28 |
| ZA867595B (en) | 1987-05-27 |
| ATE59392T1 (en) | 1991-01-15 |
| EP0218150A2 (en) | 1987-04-15 |
| IL80244A0 (en) | 1987-01-30 |
| AU6353286A (en) | 1987-04-09 |
| JPS6293295A (en) | 1987-04-28 |
| DK476586A (en) | 1987-04-08 |
| FI864021A (en) | 1987-04-08 |
| AU598480B2 (en) | 1990-06-28 |
| EP0218150A3 (en) | 1988-09-28 |
| FI84073B (en) | 1991-06-28 |
| DK476586D0 (en) | 1986-10-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |