DE1040525B - Process for the preparation of ester salts of sugars - Google Patents
Process for the preparation of ester salts of sugarsInfo
- Publication number
- DE1040525B DE1040525B DEF23598A DEF0023598A DE1040525B DE 1040525 B DE1040525 B DE 1040525B DE F23598 A DEF23598 A DE F23598A DE F0023598 A DEF0023598 A DE F0023598A DE 1040525 B DE1040525 B DE 1040525B
- Authority
- DE
- Germany
- Prior art keywords
- sugars
- ester salts
- preparation
- parts
- salts
- 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.)
- Pending
Links
- -1 ester salts Chemical class 0.000 title claims description 12
- 235000000346 sugar Nutrition 0.000 title claims description 10
- 150000008163 sugars Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- QIZPVNNYFKFJAD-UHFFFAOYSA-N 1-chloro-2-prop-1-ynylbenzene Chemical compound CC#CC1=CC=CC=C1Cl QIZPVNNYFKFJAD-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 229940035023 sucrose monostearate Drugs 0.000 description 3
- GUBGYTABKSRVRQ-PICCSMPSSA-N D-Maltose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose 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[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Saccharide Compounds (AREA)
Description
Verfahren zur Herstellung von Estersalzen von Zuckern Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Estersalzen von Zuckern. Das Verfahren besteht darin, daß man Fettsäureester von Zuckern mit Dicarbonsäureanhydriden umsetzt und die entstandenen sauren Ester, zweckmäßigerweise schon während der Umsetzung, in ihre Salze überführt.Process for the preparation of ester salts of sugars Invention is a process for the preparation of ester salts of sugars. The procedure consists in reacting fatty acid esters of sugars with dicarboxylic acid anhydrides and the acidic esters formed, expediently already during the reaction, converted into their salts.
Geeignete Fettsäureester von Zuckern sind z. B. die Ester aus Rohrzucker, Malzzucker, Milchzucker oder Raffinose mit Fettsäuren, wie Laurin-, Palmitin-, Stearin- oder Ölsäure; derartige Fettsäureester sind z. B. nach dem Verfahren der belgischen Patentschrift 5-1-123-1 durch Umesterung von Fettsäurealkylestern mit Zuckern in Diinethvlformamid unter Zusatz von lialiunicarbonat erhältlich. Als Dicarbonsäureanhydride seinen beispielsweise Maleinsäure-, Bernsteinsäure- und Phthalsäureanhydrid genannt.Suitable fatty acid esters of sugars are e.g. B. the esters from cane sugar, Malt sugar, milk sugar or raffinose with fatty acids such as lauric, palmitic, stearic or oleic acid; such fatty acid esters are e.g. B. according to the procedure of the Belgian Patent 5-1-123-1 by transesterification of fatty acid alkyl esters with sugars in Diinethylformamide available with the addition of sodium carbonate. As dicarboxylic anhydrides its called, for example, maleic, succinic and phthalic anhydride.
Die erfindungsgemäße Umsetzung erfolgt zweckmäßig unter Erwärmen in einem geeigneten Lösungsmittel, wie z. B. Diniethy lformamid, wobei die Dicarhonsäurekomponente in äquimolaren Mengen oder im Überschub eingesetzt wird.The reaction according to the invention is expediently carried out with heating in a suitable solvent, such as. B. Diniethy lformamide, the dicarhonic acid component is used in equimolar amounts or in excess.
Zur Überführung der sauren Ester in ihre Salze kann man sich der üblichen Mittel bedienen.To convert the acidic esters into their salts, one can use the usual Serve means.
Die nach dem Verfahren der Erfindung erhaltenen Estersalze von Zuckern besitzen hervorragende oberflächenaktive Eigenschaften; sie lassen sich mit besonderem Erfolg als Waschmittel verwenden. Vor den als Ausgangsmaterialien dienenden Fettsäureestern der Zucker, die ebenfalls oberflächenaktive Eigenschaften besitzen, zeichnen sie sich durch stärkere Wirksamkeit und bessere Löslichkeit aus.The ester salts of sugars obtained by the process of the invention have excellent surface-active properties; they can be special Use success as a laundry detergent. Before the fatty acid esters used as starting materials the sugars, which also have surface-active properties, draw them are characterized by greater effectiveness and better solubility.
Die in den nachfolgenden Beispielen angegebenen Teile sind Gewichtsteile. Beispiel 1 60 Teile Saccharosemonostearat und 15 Teile Phthalsäureanhydrid werden in 500 Teilen Dimethylformarnid unter Zusatz von 7 Teilen Kaliumcarbonat etwa 6 Stunden auf 90 bis 100° C erhitzt. Dann wird das Diinethylformamid aus dem Reaktionsgemisch im Vakuum abdestilliert. Das erhaltene Kaliumsalz des sauren Phthalsäureesters des Saccharosemonostearats löst sich klar in Wasser. Beispiel 2 Man verfährt, wie im Beispiel l angegeben, mit dem Unterschied, daß man an Stelle von 15 Teilen Phthalsäureanhydrid 10 Teile Maleinsäureanhydrid einsetzt. Das hierbei erhaltene Kaliumsalz des sauren Maleinsäureesters des Saccharosemonostearats löst sich ebenfalls klar in Wasser.The parts given in the following examples are parts by weight. Example 1 60 parts of sucrose monostearate and 15 parts of phthalic anhydride are used about 6 in 500 parts of dimethylformamide with the addition of 7 parts of potassium carbonate Heated to 90 to 100 ° C for hours. Then the diethylformamide is removed from the reaction mixture distilled off in vacuo. The obtained potassium salt of the acidic phthalic acid ester of Sucrose monostearate dissolves clearly in water. Example 2 Proceed as in Example 1 given, with the difference that instead of 15 parts of phthalic anhydride 10 parts of maleic anhydride are used. The resulting potassium salt of the acidic Maleic acid ester of sucrose monostearate also dissolves clearly in water.
Claims (1)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF23598A DE1040525B (en) | 1957-07-26 | 1957-07-26 | Process for the preparation of ester salts of sugars |
| CH6165058A CH373367A (en) | 1957-07-26 | 1958-07-11 | Process for the preparation of ester salts of sugars |
| NL229888D NL229888A (en) | 1957-07-26 | 1958-07-24 | |
| NL229888A NL110818C (en) | 1957-07-26 | 1958-07-24 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF23598A DE1040525B (en) | 1957-07-26 | 1957-07-26 | Process for the preparation of ester salts of sugars |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1040525B true DE1040525B (en) | 1958-10-09 |
Family
ID=7090909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF23598A Pending DE1040525B (en) | 1957-07-26 | 1957-07-26 | Process for the preparation of ester salts of sugars |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH373367A (en) |
| DE (1) | DE1040525B (en) |
| NL (2) | NL229888A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1080090B (en) * | 1958-11-27 | 1960-04-21 | Bayer Ag | Process for the production of sugar derivatives |
| US3063983A (en) * | 1958-11-27 | 1962-11-13 | Bayer Ag | Alkali metal salts of dicarboxylic acid mono-esters of carbamide esters of sugars |
-
1957
- 1957-07-26 DE DEF23598A patent/DE1040525B/en active Pending
-
1958
- 1958-07-11 CH CH6165058A patent/CH373367A/en unknown
- 1958-07-24 NL NL229888D patent/NL229888A/xx unknown
- 1958-07-24 NL NL229888A patent/NL110818C/xx active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1080090B (en) * | 1958-11-27 | 1960-04-21 | Bayer Ag | Process for the production of sugar derivatives |
| US3063983A (en) * | 1958-11-27 | 1962-11-13 | Bayer Ag | Alkali metal salts of dicarboxylic acid mono-esters of carbamide esters of sugars |
Also Published As
| Publication number | Publication date |
|---|---|
| NL229888A (en) | 1964-10-15 |
| CH373367A (en) | 1963-11-30 |
| NL110818C (en) | 1965-02-16 |
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