US3171832A - New esters of isopropylidene glucose and process of preparing the same - Google Patents

New esters of isopropylidene glucose and process of preparing the same Download PDF

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US3171832A
US3171832A US43327A US4332760A US3171832A US 3171832 A US3171832 A US 3171832A US 43327 A US43327 A US 43327A US 4332760 A US4332760 A US 4332760A US 3171832 A US3171832 A US 3171832A
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glucose
isopropylidene
isopropylidene glucose
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Knoevenagel Kurt
Himmelreich Rolf
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CF Spiess and Sohn GmbH and Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
    • C07H9/04—Cyclic acetals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils

Definitions

  • the present invention relates to new esters of isopropylidene glucose and more specifically to esters of isopropylidene glucose and fatty acids. Furthermore, the present invention is directed to a process of preparing these new compounds.
  • the products of the present invention are of interest as emulsifying agents and especially as sweling and gelatinising agents for such compounds, which contain a longer saturated or unsaturated aliphatic hydrocarbon chain with at least 5 carbon atoms.
  • the new compounds are of interest as intermediates for preparing fatty esters of glucose.
  • the new compounds have the general formula:
  • R represents an acyl group of a higher saturated or unsaturated fatty acid having from about 6 to 30 carbon atoms.
  • the new compounds can be prepared by esterification of isopropylidene glucose by a transesterification reaction with esters of fatty acids.
  • esters of isopropylidene glucose which are produced in accordance with the process of the present invention, are suitable for use as emulsifying agents and especially as swelling and gelatinising agents for such compounds Which contain a longer saturated or unsaturated aliphatic hydrocarbon chain with at least 5 carbon atoms such as for instance petroleum ether, paraffin oils, spindle oils, esters of higher saturated or unsaturated fatty acids, esters of oleic acid and salad oil. They can be used in combination with emulsifying agents to prepare pasty or liquid emulsions or suspensions especially of such organic compounds, which contain a longer saturated or unsaturated aliphatic hydrocarbon chain with at least 5 carbon atoms.
  • the quantity of an ester of isopropylidene glucose necessary for obtaining a gel with an aliphatic hydrocarbon is from about 3 to Compounds that contain a longer satuarted or unsaturated aliphatic hydrocarbon group behave similarly. In some cases as for example in the case of salad oil, the effect is favoured by adding a little water.
  • the following table indicates the percentage of some esters of isopropylidene glucose which is necessary to obtain a gel which just does not flow at room temperature 23 (3.), when swollen in the indicated solvents.
  • the following table shows the loss of weight of a mixture of 3 grams of paraffin and 7 grams of test benzine either without any or with difierent amounts of isopropyh idene glucose stearate afterstanding for 24 hours.
  • glucose esters can be obtained from isopropylidene glucose esters by splitting off the isopropylidene group by acidic hydrolysis.
  • the present invention comprises fatty acid esters of isopropylidene glucose in which the fatty acid moiety of the esters contains from about 6 to 30 carbon atoms inclusive and more desirably from about 12 to 22 carbons atoms inclusive.
  • the fatty acids which may constitute the fatty acid moiety of the esters of isopropylidene glucose are the saturated fatty acids including: lauric, myristic, palmitic, stearic acids and the like and the unsaturated fatty acids including: A -dodecylenic, palmitoleic, oleic, 'ricinoleic acids and the like.
  • the present invention further comprises a new process for producing the fatty acid esters of isopropylidene glucose.
  • the process comprises reacting a non-isopropylidene glucose ester of a fatty acid (an ester of a fatty acid with an alcohol other than isopropylidene glucose) with isopropylidene glucose.
  • the reaction is carried out by melting the components together without any solvent.
  • the reaction mixture preferably should contain an alkaline catalyst.
  • the reaction is produced by melting together the reaction components at temperatures of from about 150 C. up to about 220 C.
  • the optimum temperature range is from about 180 C. to 200 C.
  • the reaction time required is usually between about 30 minutes to 6 hours.
  • the esters of the fatty acids employed as starting materials may be simple esters of a monohydric alcohol, such as methyl palmitate, methyl stearate, ethyl laurate, methyl abietate and the like.
  • a monohydric alcohol such as methyl palmitate, methyl stearate, ethyl laurate, methyl abietate and the like.
  • an ester of a fatty acid and readily volatile alcohol such as the lower monohydric alcohols, methanol or ethanol, are employed.
  • the volatile alcohol is preferably stripped from the reaction mixture by bubbling an inert gas therethrough or by distillation, preferably, under reduced pressure, as it is liberated during the formation of the isopropylidene glucose ester.
  • non-isopropylidene glucose esters of the fatty acids employed as starting materials and as a source of fatty acids may also be esters of poly hydroxy alcohols, or polyols, where the hydroxyl groups of the alcohol are on adjacent carbons atoms, such as the diand the tri-esters of glycerol.
  • alkaline catalysts which may be employed are hydroxides and inorganic salts such as potassium, sodium and lithium hydroxides, sodium carbonate or potassium carbonate and the like or such alkaline salts as trisodium phosphate.
  • the quantity of the catalyst to be added is from about 0.1 to 10 mole percent.
  • Example 1 1.2-ISOPROPYLIDENE GLUCOSE-G-STEARATE 16 grams of isopropylidene glucose, 14.9 grams of methyl stearate and 0.1 gram of potassium carbonate dry and well ground were melted by heating the mixture up to 180 C. in an oil bath. During the heating time the mixture was stirred and kept under reduced pressure. After heating the warm liquid mass was poured in ml. of ethyl acetate. After standing for 20 minutes it was filtered and the solvent distilled off under reduced pressure. 18.1 grams of 1.2-isopropylidene glucose-6-stearate were obtained by crystallization of the brown waxy residue from ethyl alcohol.
  • the 1.2-isopropylidene glucose-6-stearate obtained is a colourless crystalline substance which has a melting point of about 46 C. to 48 C. It is only sparingly soluble in cold water, it possesses good swelling and gelatinising properties with aliphatic hydrocarbons or with an aliphatic hydrocarbon chain containing compound.
  • Example 2 LZISOPROPYLIDENE GLUCOSE-GOLEATE 11 grams of isopropylidene glucose, 14.5 grams of methyl oleate and 0.3 gram of potassium carbonate, dry and well ground, were melted together by heating the mixture for one hour up to 180 C. in an oil bath. During the heating time the mixture was stirred and kept under reduced pressure. After heating time the warm liquid mass was poured in 100 ml. of ethylacetate. After standing for 20 minutes it was filtered and the solvent distilled off under reduced pressure. 19 grams of 1.2-isopropylidene glucose-6-oleate were obtained in form of a light yellow coloured waxy mass. The substance can be purified by recrystallization from methyl alcohol. It is only sparingly soluble in cold water and possesses good swelling and gelatinising properties with aliphatic hydrocarbons or with an aliphatic hydrocarbon chain containing compound.
  • Example 3 1.2-ISOPROPYLIDENE GLUCOSE-GTALMITATE 11 grams of isopropylidene glucose, 14.5 grams of methylpalmitate and 0.15 gram of potassium carbonate, dry and well ground, were melted together by heating for 2 hours up to C. in an oil bath. During the melting time the mixture was stirred and kept under reduced pressure. After heating time the melt was poured in 100 ml. of methyl acetate. After standing for 20 minutes it was filtered and the solvent distilled off under reduced pressure. 13.9 grams of 1.2-isopropylidene glucose-6-palmitate were obtained in form of an almost colourless waxy mass. The substance can be purified by recrystallization from methyl alcohol. It possesses good swelling and gelatinising properties with aliphatic hydrocarbons or with an aliphatic hydrocarbon chain containing compound.
  • Example 4 ISOPROPYLIDENE GLUCOSE AND SALAD OIL 11 grams of isopropylidene glucose, 15.7 grams of dried salad oil and 0.8 gram of potassium carbonate, dry and well ground, were melted together by heating for 3 hours up to C. in an oil bath. During the heating time the mixture was stirred and kept under reduced pressure. Following this the melt was poured in 150 ml. of methyl acetate. After boiling with charcoal for a short time the solution was filtered at room temperature. Then the methylacetate was distilled off and the light residue dried under vacuum. 19.2 grams of a waxy, amber coloured mass were obtained. The substance had a saponification number of 66.3 and had good emulsifying properties. It possesses good swelling and gelatimsing properties with aliphatic hydrocarbons or with an aliphatic hydrocarbon chain containing compound.
  • R represents an acyl group of a higher fatty acid having from about 6 to 30 carbon atoms.
  • a process for the production of a fatty acid ester of isopropylidene glucose which comprises melting together isopropylidene glucose with an ester of an alcohol selected from the group consisting of the lower alkanols and the lower poly hydroxy alcohols wherein the hydroxyl groups are on adjacent carbon atoms with a higher fatty acid having from about 6 to 30 carbon atoms in the absence of a solvent.
  • said fatty acid ester is an ester of a fatty acid containing 6 to 30 carbon atoms with glycerol.
  • a process for the production of a fatty acid ester of isopropylidene glucose which comprises melting together isopropylidene glucose with an ester of a fatty acid containing 6 to 30 carbon atoms and a lower alkanol in the absence of a solvent and in the presence of an alkaline catalyst.

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Description

United States Patent 3,171,832 NEW ESTERS 0F HSUPROPYLIDENE GLUEGSE AND PRGQESS OF PREPARING- THE SAME Kurt Knoevenagel, Kleinlsarlhach, Grunstadt, and Roll Himmelreich, Grunstadt, Germany, assignors to C. F. Spiess dz Sohn Chemische-Fabrik, Kleinirarlhach uher Grunstadt, Rheinpfalz, Germany No Drawing. Filed .luly 18, 1960, Ser. No. 43,327 Claims priority, application Germany, Early 24, 1359,
Claims. (Cl. lath-216) The present invention relates to new esters of isopropylidene glucose and more specifically to esters of isopropylidene glucose and fatty acids. Furthermore, the present invention is directed to a process of preparing these new compounds. The products of the present invention are of interest as emulsifying agents and especially as sweling and gelatinising agents for such compounds, which contain a longer saturated or unsaturated aliphatic hydrocarbon chain with at least 5 carbon atoms. The new compounds are of interest as intermediates for preparing fatty esters of glucose.
The new compounds have the general formula:
HC0 CH3 no-o cm in which R represents an acyl group of a higher saturated or unsaturated fatty acid having from about 6 to 30 carbon atoms.
The new compounds can be prepared by esterification of isopropylidene glucose by a transesterification reaction with esters of fatty acids.
The esters of isopropylidene glucose which are produced in accordance with the process of the present invention, are suitable for use as emulsifying agents and especially as swelling and gelatinising agents for such compounds Which contain a longer saturated or unsaturated aliphatic hydrocarbon chain with at least 5 carbon atoms such as for instance petroleum ether, paraffin oils, spindle oils, esters of higher saturated or unsaturated fatty acids, esters of oleic acid and salad oil. They can be used in combination with emulsifying agents to prepare pasty or liquid emulsions or suspensions especially of such organic compounds, which contain a longer saturated or unsaturated aliphatic hydrocarbon chain with at least 5 carbon atoms.
On pouring a said aliphatic hydrocarbon or an aliphatic hydrocarbon chain containing compound on the aforementioned esters of isopropylidene glucose the latter swell within a short period of time and the hydrocarbon or hydrocarbon chain containing compound is completely absorbed. This procedure can be compared with the process of swelling of gelatine in water. On dissolving the esters of isopropylidene glucose in hydrocarbons or hydrocarbon chain containing compounds at raised temperature, the solution solidifies to a gel on cooling.
If a larger quantity of an ester of isopropylidene glucose is used, a more solid gel is obtained on cooling. The solidity or respectively the stillness of the gel depends on the quantity of esters of isopropylidene glucose used.
The quantity of an ester of isopropylidene glucose necessary for obtaining a gel with an aliphatic hydrocarbon is from about 3 to Compounds that contain a longer satuarted or unsaturated aliphatic hydrocarbon group behave similarly. In some cases as for example in the case of salad oil, the effect is favoured by adding a little water.
The following table indicates the percentage of some esters of isopropylidene glucose which is necessary to obtain a gel which just does not flow at room temperature 23 (3.), when swollen in the indicated solvents.
GELATINISING PROPERTIES OF DIFFERENT ESTERS OF ISOPROPYLIDENE GLUCOSE Isopropyli- Isopropyli- Isopropyli- Solvent dene dene deue glucose-figlucose-G- gluc'osefistearate palmitate oleate Gasoline, petrol 0.748 10. 2 13. 2 12. 3 Spindle oils 0.915 3. 5 3. 8 Petroleum ether 0.6 19. 3 24. 2 9. 7 Paraffin oil 0.876 3.7 3.1 29. 0 Methyl oleate 0.872 4.1 6. 2 10. 7 Salad oil 0.925 contain mg abt. 5%
H2O 3. l 4. 3
60.5 paraiiin oil 32.0 Water 4.3 emulsifier techn. (octylphenol with 7-9 ethylene oxide) 3.2 isopropylidene glucose-G-palmitate, or
40.0 water 2.85 sucrose stearate 2.85 isopropylidene glucose-6-palmitate, or
2.16 isopropylidene glucose ester from salad oil 4.32 paraffin oil 21.6 paraiiin solid 71.0 water On account of their properties these new compounds can be used as retention or evaporation retarding agents for products containing alphatic hydrocarbons with a chain of at least 5 carbon atoms or for such compounds which contain an aliphatic hydrocarbon chain with at least 5 carbon atoms.
So, for instance, a mixture of solid parafiin and test benzine (white or mineral spirits) suffers only a fifth to an eighth of the loss of benzine when from 2 to 5 percent of weight of an isopropylidene glucose ester are added.
The following table shows the loss of weight of a mixture of 3 grams of paraffin and 7 grams of test benzine either without any or with difierent amounts of isopropyh idene glucose stearate afterstanding for 24 hours.
Solid Test Isopropyll- Loss of Weight paraffin, benzine, dene glucose after standing grams grams stearate, for 24 hours,
mg. mg.
Furthermore, the new esters of isopropylidene glucose can be used as intermediates. Thus, for example, glucose esters can be obtained from isopropylidene glucose esters by splitting off the isopropylidene group by acidic hydrolysis.
The present invention comprises fatty acid esters of isopropylidene glucose in which the fatty acid moiety of the esters contains from about 6 to 30 carbon atoms inclusive and more desirably from about 12 to 22 carbons atoms inclusive. Among the fatty acids which may constitute the fatty acid moiety of the esters of isopropylidene glucose are the saturated fatty acids including: lauric, myristic, palmitic, stearic acids and the like and the unsaturated fatty acids including: A -dodecylenic, palmitoleic, oleic, 'ricinoleic acids and the like.
The present invention further comprises a new process for producing the fatty acid esters of isopropylidene glucose. The process comprises reacting a non-isopropylidene glucose ester of a fatty acid (an ester of a fatty acid with an alcohol other than isopropylidene glucose) with isopropylidene glucose.
The reaction is carried out by melting the components together without any solvent. The reaction mixture preferably should contain an alkaline catalyst. The reaction is produced by melting together the reaction components at temperatures of from about 150 C. up to about 220 C. The optimum temperature range is from about 180 C. to 200 C. The reaction time required is usually between about 30 minutes to 6 hours.
The esters of the fatty acids employed as starting materials may be simple esters of a monohydric alcohol, such as methyl palmitate, methyl stearate, ethyl laurate, methyl abietate and the like. Preferably, an ester of a fatty acid and readily volatile alcohol, such as the lower monohydric alcohols, methanol or ethanol, are employed.
The volatile alcohol is preferably stripped from the reaction mixture by bubbling an inert gas therethrough or by distillation, preferably, under reduced pressure, as it is liberated during the formation of the isopropylidene glucose ester.
The non-isopropylidene glucose esters of the fatty acids employed as starting materials and as a source of fatty acids may also be esters of poly hydroxy alcohols, or polyols, where the hydroxyl groups of the alcohol are on adjacent carbons atoms, such as the diand the tri-esters of glycerol.
Among the alkaline catalysts which may be employed are hydroxides and inorganic salts such as potassium, sodium and lithium hydroxides, sodium carbonate or potassium carbonate and the like or such alkaline salts as trisodium phosphate. The quantity of the catalyst to be added is from about 0.1 to 10 mole percent.
Generally when trying to melt the various other derivatives of glucose, the products turn brown and decompose, because of their high melting point. In the case of isopropylidene glucose no substantial change of colour becomes evident during the reaction, thus it is possible to obtain pure transesterification products and the separation of the isopropylidene glucose esters does not present any special difliculty.
It is known that when a solvent for a transesterification reaction is used it is very diflicult to get a pure transesterification product which does not contain any residue of the solvent used. Especially, when dimethylformamide or dimethylsulfoxide is used as a solvent it is quite impossible to remove the last traces of either of these solvents from the transesterification products. In contrast to this the transesterification products obtained by melting of isopropylidene glucose and a fatty acid ester cannot contain any traces of a solvent and therefore have a higher grade of purity.
a, Example 1 1.2-ISOPROPYLIDENE GLUCOSE-G-STEARATE 16 grams of isopropylidene glucose, 14.9 grams of methyl stearate and 0.1 gram of potassium carbonate dry and well ground were melted by heating the mixture up to 180 C. in an oil bath. During the heating time the mixture was stirred and kept under reduced pressure. After heating the warm liquid mass was poured in ml. of ethyl acetate. After standing for 20 minutes it was filtered and the solvent distilled off under reduced pressure. 18.1 grams of 1.2-isopropylidene glucose-6-stearate were obtained by crystallization of the brown waxy residue from ethyl alcohol. The 1.2-isopropylidene glucose-6-stearate obtained is a colourless crystalline substance which has a melting point of about 46 C. to 48 C. It is only sparingly soluble in cold water, it possesses good swelling and gelatinising properties with aliphatic hydrocarbons or with an aliphatic hydrocarbon chain containing compound.
Example 2 LZISOPROPYLIDENE GLUCOSE-GOLEATE 11 grams of isopropylidene glucose, 14.5 grams of methyl oleate and 0.3 gram of potassium carbonate, dry and well ground, were melted together by heating the mixture for one hour up to 180 C. in an oil bath. During the heating time the mixture was stirred and kept under reduced pressure. After heating time the warm liquid mass was poured in 100 ml. of ethylacetate. After standing for 20 minutes it was filtered and the solvent distilled off under reduced pressure. 19 grams of 1.2-isopropylidene glucose-6-oleate were obtained in form of a light yellow coloured waxy mass. The substance can be purified by recrystallization from methyl alcohol. It is only sparingly soluble in cold water and possesses good swelling and gelatinising properties with aliphatic hydrocarbons or with an aliphatic hydrocarbon chain containing compound.
Example 3 1.2-ISOPROPYLIDENE GLUCOSE-GTALMITATE 11 grams of isopropylidene glucose, 14.5 grams of methylpalmitate and 0.15 gram of potassium carbonate, dry and well ground, were melted together by heating for 2 hours up to C. in an oil bath. During the melting time the mixture was stirred and kept under reduced pressure. After heating time the melt was poured in 100 ml. of methyl acetate. After standing for 20 minutes it was filtered and the solvent distilled off under reduced pressure. 13.9 grams of 1.2-isopropylidene glucose-6-palmitate were obtained in form of an almost colourless waxy mass. The substance can be purified by recrystallization from methyl alcohol. It possesses good swelling and gelatinising properties with aliphatic hydrocarbons or with an aliphatic hydrocarbon chain containing compound.
Example 4 ISOPROPYLIDENE GLUCOSE AND SALAD OIL 11 grams of isopropylidene glucose, 15.7 grams of dried salad oil and 0.8 gram of potassium carbonate, dry and well ground, were melted together by heating for 3 hours up to C. in an oil bath. During the heating time the mixture was stirred and kept under reduced pressure. Following this the melt was poured in 150 ml. of methyl acetate. After boiling with charcoal for a short time the solution was filtered at room temperature. Then the methylacetate was distilled off and the light residue dried under vacuum. 19.2 grams of a waxy, amber coloured mass were obtained. The substance had a saponification number of 66.3 and had good emulsifying properties. It possesses good swelling and gelatimsing properties with aliphatic hydrocarbons or with an aliphatic hydrocarbon chain containing compound.
We claim: 1. An ester of isopropylidene glucose of the following general formula:
in which R represents an acyl group of a higher fatty acid having from about 6 to 30 carbon atoms.
2. The ester of isopropylidene glucose as set forth in claim 1 in which R is stearoyl.
3. The ester of isopropylidene glucose as set forth in claim 1 in which R is oleyl.
4. The ester of isopropylidene glucose as set forth in claim 1 in which R is palmitoyl.
5. A process for the production of a fatty acid ester of isopropylidene glucose which comprises melting together isopropylidene glucose with an ester of an alcohol selected from the group consisting of the lower alkanols and the lower poly hydroxy alcohols wherein the hydroxyl groups are on adjacent carbon atoms with a higher fatty acid having from about 6 to 30 carbon atoms in the absence of a solvent.
6-. The process of claim 5 in which said fatty acid ester is an ester of a saturated fatty acid containing 6 to 30 carbon atoms.
7. The process of claim 5 in which said fatty acid ester is an ester of an unsaturated fatty acid containing 6 to 30 carbon atoms.
8. The process of claim 5 in which said fatty acid ester is an ester of a fatty acid containing 6 to 30 carbon atoms with glycerol.
9. A process for the production of a fatty acid ester of isopropylidene glucose which comprises melting together isopropylidene glucose with an ester of a fatty acid containing 6 to 30 carbon atoms and a lower alkanol in the absence of a solvent and in the presence of an alkaline catalyst.
10. The process of claim 5 in which said reaction is carried out at a temperature between 150 and 220 C.
References Cited by the Examiner UNITED STATES PATENTS 2,388,887 11/45 Weissberger et al. 252-316 2,402,373 6/46 Cordero 252- 512 2,759,923 8/56 Gibbons 260-210 2,908,681 10/59 Anderson et al. 260-234 2,931,802 4/60 Touey et al. 260-234 2,992,082 7/61 OWnby et al. 260234 OTHER REFERENCES Chem. Abst. (1941 3974 LEWIS GOTTS, Primary Examiner.
J. GREENWALD, A. L. MONACELL, Examiners.

Claims (1)

1. AN ESTER OF ISOPROPYLIDENE GLUCOSE OF THE FOLLOWING GENERAL FORMULA:
US43327A 1959-07-24 1960-07-18 New esters of isopropylidene glucose and process of preparing the same Expired - Lifetime US3171832A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325472A (en) * 1964-06-18 1967-06-13 Mortimer D Sackler Polycyclohexose-polyoxyethyleneglycol suppository bases
WO1988008000A1 (en) * 1987-04-14 1988-10-20 Generale Sucriere Process for specific synthesis of o-alkyl-3 d-glucose and products obtained by such process
WO1988007999A1 (en) * 1987-04-14 1988-10-20 Generale Sucriere O-ISOPROPYLIDEN-1,2-alpha-D-GLUCOFURANNOSE ESTERS AND FATTY ACIDS, SPECIFIC SYNTHESIS AND UTILIZATIONS

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DK157308C (en) * 1985-02-27 1990-05-07 Novo Nordisk As PROCEDURE FOR THE PREPARATION OF ACETAL OR CATAL ESTERS OF POLYOLES OR MONOESTERS OF MONO OR DISACCHARIDES OR MONOGLYCERIDES

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US2388887A (en) * 1942-05-06 1945-11-13 Eastman Kodak Co Gel and gelling agent
US2402373A (en) * 1944-10-28 1946-06-18 United Rexall Drug Company Transparent mixture
US2759923A (en) * 1952-06-21 1956-08-21 Corn Prod Refining Co Catalytic esterification of glucosides with fatty acids
US2908681A (en) * 1957-02-25 1959-10-13 Dow Chemical Co Esters of 2-hydroxypropylsucrose
US2931802A (en) * 1958-04-30 1960-04-05 Eastman Kodak Co Mixed esters of glucose and sucrose
US2992082A (en) * 1958-06-24 1961-07-11 Eastman Kodak Co Anti-sludging hydrocarbon fuel oils

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2388887A (en) * 1942-05-06 1945-11-13 Eastman Kodak Co Gel and gelling agent
US2402373A (en) * 1944-10-28 1946-06-18 United Rexall Drug Company Transparent mixture
US2759923A (en) * 1952-06-21 1956-08-21 Corn Prod Refining Co Catalytic esterification of glucosides with fatty acids
US2908681A (en) * 1957-02-25 1959-10-13 Dow Chemical Co Esters of 2-hydroxypropylsucrose
US2931802A (en) * 1958-04-30 1960-04-05 Eastman Kodak Co Mixed esters of glucose and sucrose
US2992082A (en) * 1958-06-24 1961-07-11 Eastman Kodak Co Anti-sludging hydrocarbon fuel oils

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325472A (en) * 1964-06-18 1967-06-13 Mortimer D Sackler Polycyclohexose-polyoxyethyleneglycol suppository bases
WO1988008000A1 (en) * 1987-04-14 1988-10-20 Generale Sucriere Process for specific synthesis of o-alkyl-3 d-glucose and products obtained by such process
WO1988007999A1 (en) * 1987-04-14 1988-10-20 Generale Sucriere O-ISOPROPYLIDEN-1,2-alpha-D-GLUCOFURANNOSE ESTERS AND FATTY ACIDS, SPECIFIC SYNTHESIS AND UTILIZATIONS
FR2614024A1 (en) * 1987-04-14 1988-10-21 Generale Sucriere Sa PROCESS FOR SPECIFIC SYNTHESIS OF O-ALKYL-3 D-GLUCOSE AND PRODUCTS OBTAINED BY THIS PROCESS
FR2614023A1 (en) * 1987-04-14 1988-10-21 Generale Sucriere Sa PROCESS FOR SPECIFIC MONOESTER SYNTHESIS BETWEEN A FATTY ACID AND O-ISOPROPYLIDENE-1,2 A-D-GLUCOFURANNOSE AND PRODUCTS OBTAINED BY THIS PROCESS

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