DE1468176A1 - Process for the preparation of non-cyclic xylitol esters - Google Patents
Process for the preparation of non-cyclic xylitol estersInfo
- Publication number
- DE1468176A1 DE1468176A1 DE19631468176 DE1468176A DE1468176A1 DE 1468176 A1 DE1468176 A1 DE 1468176A1 DE 19631468176 DE19631468176 DE 19631468176 DE 1468176 A DE1468176 A DE 1468176A DE 1468176 A1 DE1468176 A1 DE 1468176A1
- Authority
- DE
- Germany
- Prior art keywords
- xylitol
- solvent
- fatty acid
- carbon atoms
- lower alkyl
- 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 10
- -1 cyclic xylitol esters Chemical class 0.000 title claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 14
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 14
- 239000000811 xylitol Substances 0.000 claims description 14
- 235000010447 xylitol Nutrition 0.000 claims description 14
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 14
- 229960002675 xylitol Drugs 0.000 claims description 14
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 13
- 239000000194 fatty acid Substances 0.000 claims description 13
- 229930195729 fatty acid Natural products 0.000 claims description 13
- 150000004665 fatty acids Chemical class 0.000 claims description 12
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 claims 2
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 claims 1
- 229940073769 methyl oleate Drugs 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- KZVAAIRBJJYZOW-VPENINKCSA-N (2r,3r,4s)-2-(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@H]1OC[C@H](O)[C@H]1O KZVAAIRBJJYZOW-VPENINKCSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 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
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940083987 anhydroxylitol Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 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
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 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
- 239000003921 oil Substances 0.000 description 1
- 235000014593 oils and fats Nutrition 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
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Frankfisrt a. M.-H6chstFrankfisrt a. M.-H6chst
, 7, Jan. 1954, Jan. 7, 1954
LEDOGA S.p.A. Mailand/ Italien Tia Sob«rto Lepetitj, 8LEDOGA S.p.A. Milan / Italy Tia Sob «rto Lepetitj, 8
Unsere Sr. 9565Our Sr. 9565
stellung von nicht-sykllschen Xylit-lstern nach Patent production of non-Sykllschen xylitol oil according to patent
(Patentanmeldung L 43 166 H b/12o), eingereicht am 10« Oktober 1962.(Patent application L 43 166 H b / 12o), filed on October 10th 1962.
Ss ist bekannt, daS Ister von höheren Fettsäuren mit Polyalkoholen nichtionische, oberflächenaktive Produkte bilden. Sie werden insbesondere als Emulgatoren für öle und Fette ver wendet. Zu dieser Gruppe von Verbindungen gehören beispielsweise Mono- und Polyester von Laurin-, Palmitin-, Stearin-, ölsäure und anderen Säuren mit Ithylenglykol, Glycerin, Sorbit, Mannit und Pentaerythrit. In den Fällen, in denen auf Grund der Ansah! der Kohlenstoffatome des mehrwertigen Alkohols und seiner molekularen Konfiguration dl« Sliminierung von einem oder swei Wasser molekülen unter Bildung von SauerstoffbrUöken möglich ist» erhält man al· Endprodukte der Veresterung teilweise mit den Mono- und Bianhydroderivaten der mehrwertigen Alkohole verestert· Fettsäuren. Infolge ihrer «ehr geringen Löslichkeit in Wasaer sind die An wendungemöglichkeiten 4er ob·» beschriebenen Produkt· begrenet. Augerde« weleea die·· Produkt· ein« «eviese foxisitfct auf, so ÄaflIt is known that higher fatty acids are present Polyalcohols form nonionic, surface-active products. They are used in particular as emulsifiers for oils and fats. This group of compounds includes, for example, mono- and polyesters of lauric, palmitic, stearic and oleic acid and other acids with ethylene glycol, glycerin, sorbitol, mannitol and pentaerythritol. In those cases where the Ansah! of the carbon atoms of the polyhydric alcohol and its molecular ones Configuration of the elimination of one or two water molecules is possible with the formation of oxygen bridges one al · end products of the esterification partly with the mono- and Bianhydro derivatives of polyhydric alcohols esterified · fatty acids. The possible applications are due to their rather low solubility in water 4 whether · »described product · limited. Augerde «weleea the ·· product · a« «eviese foxisitfct, so Äafl
BADBATH
U68176U68176
ihre Verwendung als Zusätze bei Lebensmitteln, besonders in hohen Dosierungen, nicht ratsam ist.their use as additives in food, especially in high doses, is not advisable.
Es wurde gefunden, daß besondere Ester von Fettsäuren mit 6 bis 30 Kohlenstoffatomen mit Xylit hergestellt werden können, einem Polyalkohol, der eine gerade Kette mit 5 Kohlenstoffatomen enthält und infolge seiner molekularen Konfiguration und der Anzahl von Hydroxylgruppen swei Anhydroderivate ergibt, d.h. Anhydroxylit und 1,4 : 2,5-Dianhydroxylit. Nach dem erfindungsgemäßen Verfahren erhält man die Mono- und Diester von Fettsäuren mit Xylit, wobei letzterer in nicht-zyklischer Form vorliegt, d.h. alle Hydroxylgruppen außer denjenigen, die mit der Fettsäure verestert sind, frei sind. Die auf diese Welse erhaltenen Produkte besitzen einen sehr hohen Grad von Oberfläehenspannunge-, Dispergierungs- und Emulgierungsaktivität und sie weisen Überraschenderweise eine sehr niedrige Toxlzität auf, so daß sie sogar in hohen Dosierungen als Zusätze zu Lebensmitteln verwendet werden können.It has been found that particular esters of fatty acids having 6 to 30 carbon atoms are made with xylitol can, a polyalcohol that contains a straight chain with 5 carbon atoms and due to its molecular configuration and the number of hydroxyl groups gives two anhydrous derivatives, i.e., anhydroxylitol and 1,4: 2,5-dianhydroxylitol. According to the invention Method one obtains the mono- and diesters of fatty acids with xylitol, the latter in non-cyclic form is present, i.e. all hydroxyl groups except those which are esterified with the fatty acid are free. The products obtained in this way have a very high degree of surface tension, Dispersing and emulsifying activity and them Surprisingly, they have a very low toxicity, so that they can be used as additives to foods even in high doses can be used.
Bei dem Verfahren der vorliegenden Erfindung wird ein Mol eines niederen Alkylesterβ einer Fettsäure mit 6-30 Kohlenstoffatomen mit drei oder mehr Mol Xylit unter Verwendung von Dimethylformamid oder Dimethylsulfoxyd als Lösungsmittel in einer Stickst off atmosphäre bei einer Temperatur zwischen 90 und XOO0C und einem Druck von 250-300 mm Hg während 12 bis 24 Stunden In Gegenwart eines alkalischen Katalysators umgesetzt. Nach Abkühlung wird das Gemisch mit Hexan geschüttelt, wobei das nicht umgesetzte Xylit ausfällt. Es wird abfiltriert und das Piltrat wird zur Trockne eingedampft, wonach der Rückstand aus einem geeigneten Lösungsmittel* beispielsweise Dichlotäthan, umkrletallisiert wird.In the process of the present invention, one mole of a lower alkyl ester of a fatty acid having 6-30 carbon atoms with three or more moles of xylitol using dimethylformamide or dimethyl sulfoxide as a solvent in a nitrogen atmosphere at a temperature between 90 and XOO 0 C and a pressure of 250-300 mm Hg reacted for 12 to 24 hours in the presence of an alkaline catalyst. After cooling, the mixture is shaken with hexane, the unreacted xylitol precipitating out. It is filtered off and the piltrate is evaporated to dryness, after which the residue is crystallized from a suitable solvent * for example dichloroethane.
Bin Gemisch aus 912 g Xylit (6MoI), 540 g Methylpalmitat ( 2 Mol), 3 000 g Dimethylformamid und 27 g Kaliumcarbonat wird 12 Stunden lang unter Stickstoff und einem Druck ▼on 250 mm Hg auf 92-95°C erhitzt. Nach Abdestillieren des Dimethylformamid Im Vakuum wird der Rückstand In Butanol undA mixture of 912 g xylitol (6MoI), 540 g methyl palmitate (2 moles), 3,000 g of dimethylformamide and 27 g of potassium carbonate is added for 12 hours under nitrogen and a pressure ▼ on 250 mm Hg heated to 92-95 ° C. After distilling off the Dimethylformamide In vacuo, the residue in butanol and
809812/UA6
BAD809812 / UA6
BATH
Cyolohexan gelöst and die Lösung mit Wasser gewaschen, um das überschüssige Xylit su entfernen. Die Lösungsmittel werden entfernt und der Rückstand wird aus A'thylacetat oder Dichloräthan kristallisiert. Als Ausbeute erhält man 540 g eines Produktes alt folgenden Eigenschaften:Cyolohexane dissolved and the solution washed with water remove the excess xylitol see below. The solvents are removed and the residue is made from ethyl acetate or dichloroethane crystallized. The yield is 540 g of a product with the following properties:
Die hohe Hydroxylzahl ist ein Zeichen dafür, daß das Produkt nicht in zyklischer Form vorliegt.The high hydroxyl number is a sign that the Product is not in cyclic form.
Ein Gemisch aus 456 g Xylit (3 Mol), 270 g Methylpalmitat (1 Mol), 912 g Dimethyl8Ulfoxyd und 13,5 g Kaliumcarbonat wird 12 stunden lang unter Stickstoff und einem Druck von 250 am Hg auf 92-940C erhitzt. Bach Abdestillieren des Di methylsulfoxyd im Vakuum wird der Rückstand in Butanol und Cyclohexan gelöst. Die Lösung wird mit Wasser gewaschen, um das überschüssige Xylit eu entfernen und dann zur Trockne verdampft. Der Rückstand wird aus Äthylacetat oder Diehloräthan kristallisiert. Es werden 300 g eines Produktes ge wonnen« das folgende Eigenschaften aufweist:A mixture of 456 g of xylitol (3 moles), 270 g of methyl palmitate (1 mole), 912 g Dimethyl8Ulfoxyd and 13.5 g of potassium carbonate is heated for 12 hours under nitrogen and at a pressure of 250 Hg at 92-94 0 C. Bach distilling off the dimethyl sulfoxide in vacuo, the residue is dissolved in butanol and cyclohexane. The solution is washed with water to remove the excess xylitol and then evaporated to dryness. The residue is crystallized from ethyl acetate or diehlorethane. 300 g of a product are obtained «which has the following properties:
809812/1^46809812/1 ^ 46
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEL0043837 | 1963-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1468176A1 true DE1468176A1 (en) | 1968-12-12 |
Family
ID=7270440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631468176 Pending DE1468176A1 (en) | 1963-01-08 | 1963-01-08 | Process for the preparation of non-cyclic xylitol esters |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1468176A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0255443A1 (en) * | 1986-07-29 | 1988-02-03 | Atta | New polyhydroxylated and highly fluorinated compounds, their preparation and their use as surfactants |
| EP0252250A3 (en) * | 1986-07-11 | 1989-06-14 | Hüls Aktiengesellschaft | Fatty acid esters of carbohydrates and a method for their preparation |
-
1963
- 1963-01-08 DE DE19631468176 patent/DE1468176A1/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0252250A3 (en) * | 1986-07-11 | 1989-06-14 | Hüls Aktiengesellschaft | Fatty acid esters of carbohydrates and a method for their preparation |
| EP0255443A1 (en) * | 1986-07-29 | 1988-02-03 | Atta | New polyhydroxylated and highly fluorinated compounds, their preparation and their use as surfactants |
| FR2602774A1 (en) * | 1986-07-29 | 1988-02-19 | Atta | NOVEL POLYHYDROXYL AND PERFLUOROALKYLATED AMPHIPHILIC MOLECULES HAVING SURFACTANT PROPERTIES |
| US4985550A (en) * | 1986-07-29 | 1991-01-15 | Alliance Pharmaceutical Corp. | Polyhydroxylated and highly fluorinated compounds, their preparation and their use as surfactants |
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