DE1934431B2 - GLYCERIDE MIXTURES CONTAINING DIACETYL-MONODODECANOYL-GLYCERIN - Google Patents

Description

Liquid glycerides of natural fatty acids are used in a wide variety of fields, for example in the pharmaceutical and cosmetic industry, in food technology as well as on the technical sector. They mostly have to meet the requirement that they are physiologically harmless and resistant to cold to be easy to dissolve fats and waxes and to have a low vapor pressure.

Are used e.g. B. glycerides, which contain bound unsaturated fatty acids in addition to saturated cloth. Such glycerides are subject to auto-oxidation, they become depending on the external conditions more or less slightly rancid (N e u w a 1 d, F: W i η k 1 er, A: J. Soc. Cosmetic Chemists 16 [1965], p. (679-85). This phenomenon can be prevented by using antioxidants, but adding them often is undesirable.

Furthermore, triglycerides of fully saturated fatty acids which are liquid at low temperatures are known (e.g. DBP 9 44 394). However, the glycerides contain significant proportions of fatty acid residues with less than 12 carbon atoms. In the event of minor cleavage during use, for example by lipases, a typical soapy odor develops.

Liquid glycerides containing acetone groups have also been described in the literature (The Journal of the American Oil Chemists' Society 35 [1958], pp. 122-7). However, these are due to their amalgamation also the tendency to become rancid or just split off fatty acids with an intense soapy smell ■ uf.

It has now been found that a triglyceride meets all of the requirements made in practice and the Disadvantages of the previously known triglycerides does not have that it is therefore resistant to oxidation, at one Cleavage does not release any fatty acids with an intensely soapy smell, and no crystalline ones after prolonged storage at 0 ° C Deposits show as well as hydrolyzed in contact with water, if its molecule has 2 acetyl groups and has 1 dodecanoyl group. All properties are retained even when this triglyceride is im Mixture with glycerides of a certain structure that has been modified in terms of the higher fatty acid residue. The mixture component can be a triglyceride which, in addition to 2 acetyl groups, contains the remainder of one more than 12 Contains fatty acid having carbon atoms. In this case, too, the development becomes intensely soapy odorous fatty acids avoided in the event of a split. With regard to the requirement that at 0 ° C a liquid Consistency must be present, is only a limitation with regard to the chain length of the acid residue required, which should not have more than 16 carbon atoms. Such mixtures can in addition to Diacetyl-monododecanoyl-glycerin up to 25 wt .-% diactyl-monohexadecanoylglycerin or up to 90 % By weight of diacetyl-monotetradecanoylglycerin

Your glyceride mixture can also contain up to 10% by weight Acetyl-di-alkanoyl-glycerin be admixed, the Alkanoy! Groups in turn can contain 12-16 carbon atoms.

The invention therefore relates to mixtures of glycerides consisting of 10-99 percent by weight diacetylmonododecanoyl glycerin and up to 25 percent by weight of diacetyl monohexadecanoyl glycerol or up to 90 percent by weight of diacetyl monohexadecanoyl glycerol and optionally up to 10 percent by weight of an acetyl-dialkanoyl-glycerol, the alkanoyl group Has 12-16 carbon atoms.

Furthermore, enough diglycerides can be contained that a hydroxyl number of up to 20 results.

Diacetyl-monododecanoyl-glycerin can be produced once by esterifying lauric acid with excess glycerol and isolation of the resulting monoglyceride by molecular distillation, after which the monoglyceride is acetylated with acetic anhydride to form the triglyceride. Furthermore can this triglyceride can be obtained by transesterification of Tridodecanoylglycerol with triacetin and separation of the reaction product by molecular distillation.

Since diacetyl-monododecanoyl-glycerin is also advantageous in a mixture with other glycerides Retains properties, it is possible in the technical manufacture among the technical ones on the market Make an appropriate selection of fatty acid cuts.

example 1

Molecular distillation turned a lauric acid partial glyceride mixture Enriched with lauric acid monoglyceride. It was pure by gas chromatography and had the following data:

Melting point: 63.0 ° C
Acid number: 0.88
Saponification number: 207
Hydroxyl number: 409

50 grams of this monoglyceride was refluxed with 100 grams of acetic anhydride at normal pressure for 2 hours, after which acetic acid and excess acetic anhydride were distilled off, finally under vacuum. Then for 2 hours at 15O ⁰ C and 20 Torr water vapor was 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 refractive index at 20 ° C., measured with daylight, was 1.4475; the substance solidified at -21.0 ⁰ C and boiling at 197 ⁰ C and 1.5 Torr.

Example 2

A obtained by the molecular distillation Laurinsäurepartialglyceridfraktion with the following data: Melting point 6O ⁰ C, hydroxyl value 381, saponification value 214, acid number 2.2 was shown by gas chromatographic analysis of 90.5% of monoglyceride and 9.5% diglyceride. It was acetylated analogously to Example 1 and

produced a product with a hydroxyl number of 0, a saponification number of 462 and an acid number of 2.35. This product remained completely after storage at 0 ^° C. for one week

Example 3

Analogously to Example 1, 100 g of myristic acid monoglyceride (digiyceride 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 number 469, acid number 0) with 15 parts by weight of diacetyldodecanoylglycerol remained completely clear on prolonged storage at 0 ° C.

Example 4

78 parts by weight of diacetyl-dodecanoyl-glycerin were with 22 parts by weight of diacetyl-hexariecanoyl-glycerin mixed The mixture remained completely clear after prolonged storage at 0 ° C.

Example 5

10 parts by weight of diacetyl-hexadecanoyl-glycerin, 40 parts by weight of 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 (2)

Patent claims: 1. Glyceride mixtures consisting of 10-99 percent by weight of diacetyl-monododecanoyi-glycerin and up to 25 percent by weight of diacetyl monohexadecanoyl glycerol or up to 90 percent by weight Diacetyl-monotetradecanoyl-glycerin and optionally up to 10 percent by weight of an acetyldialkanoyl-glycerin, the alkanoyl group having 12-16 carbon atoms 2. Glyceride mixtures according to claim 1, which contain so much diglycerides that there is a hydroxyl number results in up to 20. 15th