DE1518251A1 - Process for the production of sucrose esters of fatty acids - Google Patents
Process for the production of sucrose esters of fatty acidsInfo
- Publication number
- DE1518251A1 DE1518251A1 DE19641518251 DE1518251A DE1518251A1 DE 1518251 A1 DE1518251 A1 DE 1518251A1 DE 19641518251 DE19641518251 DE 19641518251 DE 1518251 A DE1518251 A DE 1518251A DE 1518251 A1 DE1518251 A1 DE 1518251A1
- Authority
- DE
- Germany
- Prior art keywords
- sucrose
- fatty acid
- fatty acids
- polar solvent
- esters
- 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
- 238000000034 method Methods 0.000 title claims description 12
- 239000001959 sucrose esters of fatty acids Substances 0.000 title claims description 7
- 235000010965 sucrose esters of fatty acids Nutrition 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 5
- 229930006000 Sucrose Natural products 0.000 claims description 14
- 239000005720 sucrose Substances 0.000 claims description 14
- 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 claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 11
- 239000000194 fatty acid Substances 0.000 claims description 11
- 229930195729 fatty acid Natural products 0.000 claims description 11
- 239000002798 polar solvent Substances 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 238000005809 transesterification reaction Methods 0.000 claims description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 1
- 229960004793 sucrose Drugs 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- 235000000346 sugar Nutrition 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- -1 sucrose ester Chemical class 0.000 description 3
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- RVWOWEQKPMPWMQ-UHFFFAOYSA-N methyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OC RVWOWEQKPMPWMQ-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229940114069 12-hydroxystearate Drugs 0.000 description 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Description
Herstellung yon_ S&ccharose_- estern von FettsäurenManufacture of S & cc harose esters of fatty acids
Saccharoseester von Fettsäuren sind bekannt und finden in der Praxis auch Verwendung als Emulgatoren» In neuerer Zeit sind vor allem die Saccharoseester von Fettsäuren mit 12 bis 22 Kohlenstoffatomen, die mindestens eine schwach hydrophile Gruppe in der Fettsäurekette enthalten., wichtig geworden, weil sie sich durch hervorragende waschaktive Eigenschaften auszeichnen und biologisch leicht zu völlig unschädlichen Substanzen abbaubar sind (deutsche Patentanmeldung Z 10316 IVa/2Je). * -Sucrose esters of fatty acids are known and can be found in practice also used as emulsifiers »In recent times, especially the sucrose esters of Fatty acids with 12 to 22 carbon atoms that have at least one weakly hydrophilic group in the fatty acid chain included., become important because they are characterized by excellent washing properties and are easily biodegradable to completely harmless substances (German patent application Z 10316 IVa / 2Je). * -
Die Herstellung"der Saccharoseester von Fettsäuren erfolgt üblichervreise durch Umesterung von niederen Al- . . ™ kylestern der Fettsäuren mit' Saccharose in einem polaren Lösungsmittel (siehe britische Patentschriften 809 815 und 826 801). Das Molverhältnis von Fettsäurealkylester zu Zucker beträgt hierbei etwa 3 V-I und mehr.. Als Katalysatoren kommen vor allem alkalische Verbindungen, insbesondere Kaliumcarbonat, infr-age, Nach Beendigung der Umesterung wird der überwiegende Teil des Lösungsmittels im Vakuum entfernt. Dann muß ein anderes geeignetes Lösungsmittel zugegebenThe sucrose esters of fatty acids are usually produced by transesterification of lower alkyl and more .. The main catalysts are alkaline compounds, in particular potassium carbonate, infr-age, After the transesterification has ended, most of the solvent is removed in vacuo, and another suitable solvent must then be added
, BAD, BATH
909830/147 1909830/147 1
werden, um eine Zersetzung der Zuckerester durch zu langes Erwärmen zu verhindern und den überschüssigen Zucker auszufällen. Die dann erhaltene Lösung des Zuckeresters muß noch gewaschen werden und nach Abdampfen des Extraktionsmittels bleibt der Zuckerester in reiner Form zurück.to prevent the sugar esters from decomposing to prevent prolonged heating and the excess Precipitate sugar. The solution of the sugar ester then obtained still has to be washed and after evaporation of the extractant, the sugar ester remains in its pure form.
Dieses Verfahren hat vor allem bei seiner großtechnischen Durchführung den Nachteil, daß es außerordentlich kompliziert ist und einen großen Überschuß an Saccharose sowie große Kengen des polaren Lösungsmittels erfordert. Sowohl der überschüssige Zucker als auch das Lösungsmittel müssen zurückgewonnen und wieder eingesetzt werden, wenn das Verfahren wirtschaftlich sein soll. Das wiederum erfordert für beide Substanzen zusätzliche Reinigungsmaßnahrcen mit dem entsprechenden apparativen Aufwand.This procedure has mainly at its large scale Carrying out the disadvantage that it is extremely complicated and a large excess of it Sucrose and large quantities of the polar solvent requires. Both the excess sugar and the solvent need to be recovered and put back again can be used if the process is to be economical. That in turn requires substances for both additional cleaning measures with the corresponding equipment expenditure.
Gegenstand der Erfindung ist ein verbessertes Verfahren zur Herstellung von Saccharoseestern von Fettsäuren mit 12 bis 22 Kohlenstoffatomen, bei"dem die Umesterung der Saccharose mit einem niederen Fettsäurealkylester in einem flüssigen Zweiphasensystem durchgeführt wird, dessen eine Phase zu Eeginn der Reaktion aus einer Lösung des Fettsäurealkylesters in einem aliphatischen oder aromatischen Kohlenwasserstoff besteht und dessen andere Phase die Saccharose und ggf. den Katalysator in einem polaren Lösungsmittel gelöst enthält.The invention relates to an improved method for the production of sucrose esters of fatty acids with 12 to 22 carbon atoms, in which the transesterification of sucrose with a lower fatty acid alkyl ester is carried out in a liquid two-phase system, one phase of which at the beginning of the reaction from a Solution of the fatty acid alkyl ester in an aliphatic or aromatic hydrocarbon and its other phase contains the sucrose and possibly the catalyst dissolved in a polar solvent.
Polare Lösungsmittel, die für die Zwecke der Erfindung infrage kommen, sind N-Methylir.orpholin» Triethylamin. Pyridin, Chinolin, Pyrazin, N-Kethylpyrazin. N3N'-Pirr.e-Polar solvents which are suitable for the purposes of the invention are N-methylir.orpholine »triethylamine. Pyridine, quinoline, pyrazine, N-kethylpyrazine. N 3 N'-Pirr.e-
909830/1471 . BAD ORIGINAL909830/1471. BATH ORIGINAL
thylpiperazin, 2-Pyrrolidon, N-Kethylpyrrolidon sowie N,Il'-Dimethylformamid und Diniethylsulfoxyd, die besonders bevorzugt werden. Als Lösungsmittel für die niederen Alkylester der Fettsäuren eignen sich unpclare Lösungsmittel., die zwischen 100 und 2CO0C sieden., insbesondere werden aromatische und aliphatische Kohlemvasserstcffe. wie Toluol. Ethylbenzol ,Benzin, Cyclchexylbenzol, Ncnylbenzol, Ligroin u. dgl/ vertvendet. Das Gewichtsverhältnis vcn polarem Lösungsmittel zu dem flüssigen Kohlenwasserstoff beträgt zweckmäßig 0,5 '- 1 bis 5 ί !■/- insbesondere 2 : 1 bis 2,5 : 1.thylpiperazine, 2-pyrrolidone, N-methylpyrrolidone and N, II'-dimethylformamide and diniethyl sulfoxide, which are particularly preferred. Suitable solvents for the lower alkyl esters of the fatty acids are non-clear solvents which boil between 100 and 2CO 0 C, in particular aromatic and aliphatic carbons. like toluene. Ethylbenzene, gasoline, cyclchexylbenzene, nylbenzene, ligroin and the like are used. The weight ratio vcn polar solvent to the liquid hydrocarbon is advantageously from 0.5 '- 1 to 5 ί ■ / - in particular from 2: 1 to 2.5: 1st
Das erfindungsgemäße Verfahren ist ganz allgemein zur. Herstellung vcn Saccharoseestern von Fettsäuren brauchbar. Es hat* sich als besonders vorteilhaft zur Herstellung der technisch wichtigen Saccharcse-■"ester vcn Fettsäuren mit mindestens einer schwach hydrophilen Gruppe, wie^ z.B. einer Hydroxyl-^ .Garbo-, fiyl-. OxTm-a. oder Alkoxy gruppe; erwiesen.The inventive method is very general for. Production of sucrose esters of fatty acids useful. It has proven to be particularly advantageous for the production of the industrially important saccharose esters of fatty acids with at least one weakly hydrophilic group, such as a hydroxyl, garbo, fiyl, ox , or alkoxy group.
Das Prinzip des Verfahrens besteht darin,, daß die ,Saccharose und der Katalysator zunächst bei mäßig erhöhter Temperaturj z.B. 70 bis 9OQ. in dem polaren Lösungsmittel gelöst werden. Dann τ/ird der niedere Alkylester der Fetfcsäure. deren Saccharcseester erieügt werden soll, insbescndere der Methyl- oder ftthylester. in dem flüssigen Kohlenwasserstoff gelöst und die beiden Phasen werden unter Bühren im Vakuum bei Temperaturen zwischen ^O und l-SOy, instescndere etim 80 bis 90°. zur Reaktion gebracht. Der Alkylester verbleibt zunächst fast vollständig in der Kohlenwasserstoffphase. Der während der UmesterungThe principle of the method is that the ,,, sucrose and the catalyst initially at moderately elevated Temperaturj eg 70 to 9O Q. be dissolved in the polar solvent. Then τ / ird the lower alkyl ester of fatty acid. whose sucrose ester is to be obtained, especially the methyl or ethyl ester. dissolved in the liquid hydrocarbon, and the two phases are heated under vacuum at temperatures between 0 and 1-SO y , at temperatures between 80 and 90 °. brought to reaction. The alkyl ester initially remains almost completely in the hydrocarbon phase. The one during the transesterification
909830/147 1 BAD ORIGINAL909830/147 1 ORIGINAL BATHROOM
freiuerdende niedere Alkohol'■>.-. destilliert ab und zugleich steigt langsam das Lösungsvermögen des polaren Lösungsmittel für den Kchlenv.'asser- . stoff, Keil der sich bildende Saccharoseester in dem polaren Lösungsmittel besser löslich ist als die Saccharose. Nach einer Reaktionszeit von 5 bis 12 St und en j im allgemeinen etwa 8 bis 9 Stunden., ist die Umesterung beendet und durch Erhöhung der Temperatur im Reaktionsgemisch oder des angelegten Vakuums oder dürcli beide Maßnahmen v/erden dann die beiden Lösungsmittel abdestilliert und der erzeugte Zuckerester verbleibt im Rückstand.Liberating lower alcohol '■> .-. distilled off and at the same time the dissolving power of the polar solvent for the Kchlenv.'asser-. substance , wedge the sucrose ester that is formed is more soluble in the polar solvent than sucrose. After a reaction time of 5 to 12 hours and generally about 8 to 9 hours, the transesterification is complete and, by increasing the temperature in the reaction mixture or the vacuum applied, or by both measures, the two solvents are then distilled off and the solvent produced Sugar ester remains in the residue.
Das neue Verfahren hat verglichen mit den bekannten Darstellungsmöglichkeiten die folgenden verfahrenstechnischen und wirtschaftlichen Vorteile.; Saccharose und der niedere Alkylester der Fettsäure können im Kolverhältnis 1 : 1 eingesetzt werden. Das Verfahren wird also nicht durch überschüssigen Zucker belastet und die Abtrennung und Reinigung des überschüssigen Zuckers entfallt. Die für die Umesterung erforderliche gesamte Lösungsmittelmenge beträgt weniger als die Hälfte der bisher' üblichen Menge., Durch die wesentlich einfachere Aufarbeitung und den Fortfall aller zusätzlichen Reinigungsverfahren wird die Ausbeute an Zuckerester im Durchschnitt um etwa 10 % erhöht.The new method has the following procedural and economic advantages compared to the known display options. Sucrose and the lower alkyl ester of fatty acid can be used in a 1: 1 ratio. The process is therefore not burdened by excess sugar and the separation and purification of the excess sugar is no longer necessary. The total amount of solvent required for the transesterification is less than half of the usual amount. Due to the much simpler work-up and the elimination of all additional purification processes, the yield of sugar esters is increased on average by about 10 % .
51/5 g Saccharose (0/15 KoI) wurden mit-0,5 g Kaliumcarbonat in 120 g Dirneftjylsulfoxyd bei 850C gelöst. Gleichzeitig wurde eine Lösung vcn Ö/15 KcI 12-Hydrcxystearinsäuremethylester in 50 g C^olohexylbenzcl51/5 g sucrose (0/15 koi) were dissolved with 0.5-g of potassium carbonate in 120 g Dirneftjylsulfoxyd at 85 0 C. At the same time a solution of 1/15 KcI of 12-Hydroxystearic acid methyl ester in 50 g of C ^ olohexylbenzcl
909830/1471909830/1471
BADORlQfNALBADORlQfNAL
hergestellt und die beiden Phasen dann bei 85 C unter Vakuum 9 Stunden lang kraftig gerührt. Dann wurden die beiden Lösungsmittel unter Vakuum abdestilliert. Der Rückstand besteht aus dem Saccharoseester der 12-Hydroxystearinsäure. Die Ausbeute liegt über-95 $· Das Produkt ist als solches unmittelbar als waschaktive Komponente von Waschmitteln verwendbar und senkte die Oberflächenspannung von Wasser 10 deutscher Härte auf j8 dyn/cm.and the two phases were then vigorously stirred at 85 C under vacuum for 9 hours. Then the two solvents were distilled off under vacuum. The residue consists of the sucrose ester of 12-hydroxystearic acid. The yield is about 95 $ · The product as such is just as detergent component of detergents used, lowering the surface tension of water 10 German hardness j8 dyn / cm.
Bel spie l_2j_ ■ ( Bel spie l_2j_ ■ (
Ein Gemisch aus 90 g Diirethylsulfoxyd. 50 g Eenzin eines Siedebereichs von 100 bis l40°C, JO g Saccharose, 21,6 g 12-Hydroxystearinsäuremethylester und 0,5 g Kaliumcarbonat als Katalysator wird bei 85 C unter einem Vakuum von 100 mm Hg 9 Stunden lang kräftig gerührt. Nach Abdestillieren der Lösungsmittel bleibt Saccharose-12-Hydroxystearat mit einer Oberflächenspannung von 38 dyn/cm zurück. Die Ausbeute beträgt 96 %. A mixture of 90 g Diirethylsulfoxyd. 50 g of benzine boiling in the range from 100 to 140 ° C., JO g of sucrose, 21.6 g of methyl 12-hydroxystearate and 0.5 g of potassium carbonate as a catalyst are stirred vigorously at 85 ° C. under a vacuum of 100 mm Hg for 9 hours. After the solvent has been distilled off, sucrose-12-hydroxystearate remains with a surface tension of 38 dynes / cm. The yield is 96%.
Entsprechende Ausbeuten werden bei der Urr.es te rungCorresponding yields are given at the time of original restoration
von Myr ist insäur e- oder Laurinsäurerr.ethylester mit i of Myr is insäur e- or Laurinsäurerr.ethylester with i
Saccharose erhalten.Obtain sucrose.
90-98,30/U7190-98.30 / U71
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ0010963 | 1964-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1518251A1 true DE1518251A1 (en) | 1969-07-24 |
Family
ID=7621628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641518251 Pending DE1518251A1 (en) | 1964-07-08 | 1964-07-08 | Process for the production of sucrose esters of fatty acids |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3347848A (en) |
| DE (1) | DE1518251A1 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL158165B (en) * | 1973-05-15 | 1978-10-16 | Amsterdam Chem Comb | PROCESS FOR THE PREPARATION OF CARBONIC ACID ESTERS FROM LINEAR ALIPHATIC SUGAR ALCOHOLS. |
| JPS5821637B2 (en) * | 1973-10-30 | 1983-05-02 | 三菱化学株式会社 | Seizouhouhou |
| JPS5123254A (en) * | 1974-08-14 | 1976-02-24 | Nippon Shinyaku Co Ltd | Suteriru beetaa dd gurukoshidono parumichinsanesuteruno seizohoho |
| US4363763A (en) * | 1980-02-25 | 1982-12-14 | The Procter & Gamble Company | Polyol esters of alpha-hydroxy carboxylic acids |
| US4469635A (en) * | 1980-12-24 | 1984-09-04 | The Procter & Gamble Company | Polyol esters of alpha-hydroxy carboxylic acids |
| US4806632A (en) * | 1986-12-29 | 1989-02-21 | The Procter & Gamble Company | Process for the post-hydrogenation of sucrose polyesters |
| US5550220A (en) * | 1987-05-13 | 1996-08-27 | Curtice-Burns, Inc. | Alkyl glycoside fatty acid polyester fat substitute food compositions and process to produce the same |
| US4942054A (en) * | 1987-05-13 | 1990-07-17 | Curtice-Burns, Inc. | Process for producing low calorie foods from alkyl glycoside fatty acid polyesters |
| JP3002922B2 (en) * | 1992-02-12 | 2000-01-24 | 第一工業製薬株式会社 | Method for producing high monoester-containing sucrose higher fatty acid ester |
| US5945529A (en) * | 1996-07-19 | 1999-08-31 | The Procter & Gamble Company | Synthesis of polyol fatty acid polyesters using column with inert gas stripping |
| US5767257A (en) * | 1996-07-19 | 1998-06-16 | The Procter & Gamble Company | Methods for producing polyol fatty acid polyesters using atmospheric or superatmospheric pressure |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2948716A (en) * | 1956-04-12 | 1960-08-09 | Trevor C M Davis | Purification of sugar esters |
| GB826801A (en) * | 1957-08-29 | 1960-01-20 | Distillers Co Yeast Ltd | Recovery of sucrose esters |
| GB859305A (en) * | 1958-07-01 | 1961-01-18 | Distillers Co Yeast Ltd | Production of sucrose esters |
| US3054789A (en) * | 1959-02-06 | 1962-09-18 | Ledoga Spa | Process for the preparation of pure sucrose esters |
| DE1270021B (en) * | 1963-03-21 | 1968-06-12 | Bayer Ag | Process for separating unreacted sugars from the reaction mixture obtained in the production of sugar fatty acid esters from fatty acid alkyl esters and excess amounts of sugars in dimethylformamide, dimethylacetamide, dialkyl sulfoxide or butyrolactone |
-
1964
- 1964-07-08 DE DE19641518251 patent/DE1518251A1/en active Pending
-
1965
- 1965-07-07 US US470196A patent/US3347848A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3347848A (en) | 1967-10-17 |
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| SH | Request for examination between 03.10.1968 and 22.04.1971 |