DE1934431A1 - Diacetyl monododecanoyl glycerin - Google Patents

Abstract

Diacetyl monododecanoyl glycerin, which can be used in pharmacology cosmetics, foodstuffs, and other products, has valuable properties; in particular it does not crystallise at 0 degree C., does not evolve on decomposition wapy smelling fatty acids, is resistant against oxidation and hydrolysis with water. Similar properties are possessed by mixtures of 10-99% by wt. of this compound with up to 25% of diacetyl hexadecanoyl glycerin and/or up to 90% of diacetyl tetradecanoyl glycerin, and up to 10% of an acetyl dialkanoyl glycerin, in which the alkanoyl group contains 12-16C atoms. The mixture may also contain diglycerides in such an amount that they hydroxyl number of the mixture does not exceed 20. These compounds can be produced by esterifying the compounding acid with excess glycerin, separating the monoglyceride and esterifying it with acetic acid, or by transesterification of a higher triglyceride with triacetin.

Description

Liquid glycerides of natural fatty acids are used on the various fields, for example in pharmaceutical and cosmetic Industry, food technology and the technical sector. she mostly have to meet the requirement, physiologically harmless and cold-resistant to be easy to dissolve fats and waxes and to have a low vapor pressure Glycerides, for example, are used, which are not only saturated but also unsaturated fatty acids bound included. Such glycerides are subject to auto-oxidation, they are in Depending on the external conditions, more or less easily rancid (Neuwald, Q: Winkler, A: J.Soc. Cosmetic Chemists 16 (1965) pp. 679-85). This appearance can be prevented by antioxidants, but their addition is often undesirable is.

Furthermore, liquid triglycerides are complete at low temperatures saturated fatty acids known (e.g. DBP 944 394).

However, the glycerides contain considerable amounts of fatty acid residues with less than 12 carbon atoms. With minor splitting during application, for example through lipase, a typically soapy odor develops.

Liquid glycerides containing aceto groups are also in the literature (The Journal of the American Oil Chemists' Society 35 (1958) Page 122-7). However, due to their composition, these also have the tendency to become rancid or to split off fatty acids with an intense soapy smell.

It has now been found that a triglyceride is all of the practice Fulfilled demands made and the disadvantages of the previously known triglycerides does not show that it is therefore resistant to oxidation, in the event of a split it is not intensive Soapy-smelling fatty acids are released, after prolonged storage at 0 ° C no crystalline ones Deposits shows as well as in contact with water not hydrolyzed if its molecule Has 2 acetyl groups and 1 dodecanoyl group.

All properties are also retained when this triglyceride in a mixture with glycerides certain, modified with regard to the higher fatty acid residue Structure is present. The elimination component can be a triglyceride, which in addition to 2 acetyl groups contains the remainder of a fatty acid having more than 12 carbon atoms. In this case, too, the formation of intensely soapy-smelling fatty acids is involved a split avoided. With regard to the requirement that a liquid Consistency must be present, is only a limitation with regard to the Chain length of the acid residue required, which do not have more than 16 carbon atoms target. Such mixtures can in addition to the diaetyl-monododecanoyl-glycerin up to 25 Gew Üiactyl-monohexadecanoylglycerin or up to 90 Gew.-k diacetyl-monotetradecanoylglycerin contain.

The one containing 2 acetyl groups and 1 dodecanoyl group in the molecule Triglyceride, as well as the mixtures described above, can also contain up to 10% by weight of acetyl-di-alkanoyl-glycerin be added, the alkanoyl groups in turn may contain 12 carbon atoms.

Furthermore, as much diglycerides can contain rope; that one Hydroxyl number up to 20 results.

The glyceride according to the invention can be produced by once Esterification of lauric acid with excess glycerine and isolation of the resulting Monoglyceride by molecular distillation, followed by acetylation of the monoglyceride takes place with acetic anhydride to the triglyceride. Furthermore, the inventive Triglyceride can be obtained by transesterifying tridodecanoylglycerol with triacetin and separating the reaction product by molecular distillation.

Since the glyceride according to the invention is also mixed with other glycerides can retain its advantageous properties, it is possible at the technical level Production among the commercially available technical fatty acid cuts one make appropriate choices.

Example 1 A lauric acid partial glyceride mixture was obtained by molecular distillation Enriched with lauric acid monoglyceride. It was pure by gas chromatography and had following data: melting point: 63.0 ° C acid number: 0.88 saponification number: 207 hydroxyl number: 409 50 grams of this monoglyceride were mixed with 100 grams of acetic anhydride at normal pressure Refluxed for 2 hours, after which acetic acid and excess acetic anhydride were added distilled off, finally under vacuum. Then 2 hours at 150 ° C and 20 Torr water vapor passed through the product. This then had the hydroxyl number 0, the acid number 0.8 and the saponification number 467 (calculated value: 469). The index of refraction at 200C, measured with daylight, was 1.4475; the substance solidified at - 21.00C and boiled at 19700 and 1.5 torr.

Example 2 A lauric acid partial glyceride fraction obtained by molecular distillation with the following data: melting point 50 C, flydroxyl number 381, saponification number 214, According to the gas chromatographic analysis, the acid number 2.2 consisted of 90.5 * monoglyceride and 9.5% diglyceride. It was acetylated analogously to Example 1 and gave a product with the hydroxyl number 0, the saponification number 462 and the acid number 2.35. This product remained completely clear after one week of storage at OOG.

Example 3 Analogously to Example 1, 100 g of myristic acid monoglyceride were added (Diglyceride content 8.8% by weight, melting point 69 ° C., hydroxyl number 330.0, saponification number 117.5, acid number 1.28) reacted with 100 g of acetic anhydride and worked up A mixture of 85 parts by weight of the product (hydroxyl number 0, saponification factor 469, acid number 0) with 15 parts by weight of diacetyl-dodecanoylglycerol remained longer Storage-at 0 ° C completely clear.

Example 4 78 parts by weight of diacetyl-dodecanoyl-glycerin were mixed with 22 parts by weight of diacetyl-hexadecanoyl-glycerin mixed. The mixture persisted longer storage at 0 ° C completely clear.

Example 5 10 parts by weight of diacetyl-hexadecanoyl-glycerol, 40 parts by weight Diacetyl-tetradecanoyl-glycerin and 50 parts by weight of diacetyl-dodecanoyl-glycerin were mixed. The mixture remained completely clear on prolonged storage at 0 ° C.

Claims (1)

Claims 8) diacetyl monododecanoyl glycerin. 9 moisture-resistant, with OOC still no crystalline deposits exhibiting, no intensely soapy-smelling fatty acids in a cleavage Freedom-setting glyceride mixture that does not hydrolyze with water from 10 - 99 percent by weight of diacetyl monododecanoyl glycerine and up to 25 percent by weight Diacetyl-tetradecanoyl-glycerine and / or up to 90 percent by weight of diacetyl-tetradecanoyl-glycerine and optionally up to 10 percent by weight of an acetyl-dialkanoyl-glycerin, wherein the alkanoyl group has 12-16 carbon atoms. 3.) glyceride mixture, characterized in that in addition to the triglyceride according to claim 1 or the glyceride mixtures according to claim 2 as much diglycerides are included so that a hydroxyl number of up to 20 results.