US3748265A - Oxidation- and low temperature-resistant glycerides of natural fatty acids - Google Patents

Oxidation- and low temperature-resistant glycerides of natural fatty acids Download PDF

Info

Publication number
US3748265A
US3748265A US00119828A US3748265DA US3748265A US 3748265 A US3748265 A US 3748265A US 00119828 A US00119828 A US 00119828A US 3748265D A US3748265D A US 3748265DA US 3748265 A US3748265 A US 3748265A
Authority
US
United States
Prior art keywords
weight
triglyceride
diacetyl
oxidation
fatty acids
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.)
Expired - Lifetime
Application number
US00119828A
Inventor
H Buenger
G Renckhoff
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dynamit Nobel AG
Original Assignee
Dynamit Nobel AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dynamit Nobel AG filed Critical Dynamit Nobel AG
Application granted granted Critical
Publication of US3748265A publication Critical patent/US3748265A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0028—Carboxylic acids; Their derivates

Definitions

  • Liquid glycerides of natural fatty acids are employed in a great variety of fields, for example in the pharmaceutical and cosmetic industries, in [food technology, as well as in the technical sector. In most cases, they must meet the requirements of being physiologically accetpable as well as nonfreezing, capable of readily dissolving fats and waxes, and having a low vapor pressure.
  • Glycerides are employed, for example, which contain bound therein also unsaturated fatty acids, in addition to saturated ones. Such glycerides are prone to autoxidation; they become more or less readily rancid in dependence on the external conditions (Neuwald, F.; Winkler, A.: J. Soc. Cosmetic Chemists 16 (1965), pp. 679-85). This phenomenon can be prevented by antioxidants; however, the addition of such agents is in many cases undesirable.
  • triglycerides of fully saturated fatty acids which are liquid at low temperatures (for example, German Pat. 944,394).
  • the glycerides contain considerable proportions of [fatty acid residues of less than 12 carbon atoms. By minor splitting reactions taking place during use, for example by lipases, a typically soapy odor develops.
  • liquid glycerides containing aceto groups have been described in the literature (The Journal of the American Oil Chemists Society 35 (1958), pp. 122-7). However, these glycerides, due to their composition, like wise exhibit the tendency toward rancidity or toward splitting off fatty acids causing an intensely soapy odor.
  • a triglyceride fulfills all practical requirements and does not exhibit the disadvantages of the triglycerides known heretofore, i.e. a triglyceride which is oxidation-resistant, does not liberate intensely soapy smelling fatty acids upon a splitting reaction, does not exhibit any crystalline deposits after being stored for a longer period of time at 0 C., and is not hydrolyzed upon contact with Water, if the molecule of such triglyceride exhibits two acetyl groups and one dodecanoyl group.
  • the mixture component can be a triglyceride containing, in addition to two acetyl groups, the residue of a fatty acid exhibiting more than 12 carbon atoms. Also in this case, the formation of fatty acids of an intensely soapy odor is avoided during the occurrence of a splitting reaction.
  • a liquid 3,?43,Z05 Patented July 24, 1973 "ice consistency must be present at 0 C., there is, in this case, merely a limitation with respect to the chain length of the acid residue, which latter is to have no more than 16 carbon atoms.
  • Such mixtures can contain, in addition to diacetyl monododecanoyl glycerol, up to 25% by weight of diacetyl monohexadecanoyl glycerol or up to by weight of diacetyl monotetradecanoyl glycerol.
  • the glyceride of this invention can be produced, according to one process, by the esterification of lauric acid with excess glycerol and isolation of the thus-formed mono-glyceride by molecular distillation, whereupon an acetylation of the monoglyceride is connected with acetic anhydride to produce the triglyceride.
  • the triglyceride of this invention can be obtained by the interesterifieation of tridodecanoyl glycerol with triacetin and separation of the reaction product by molecular distillation.
  • the glyceride of this invention can also retain its advantageous properties in a mixture with other glycerides, it is possible to make a suitable selection, during the manufacture thereof, among the technical fatty acid blends commercially available.
  • EXAMPLE 2 A lauric acid partial glyceride fraction obtained during molecular distillation with the following data: melting point, 60 C.; hydroxyl number, 381; saponification number, 214; acid number, 2.2; consisted, in accordance with analysis by gas chromatography, of 90.5% monoglyceride and 9.5% diglyceride. This fraction was acetylated in correspondence with Example 1, thus resulting in a product having a hydroxyl number of 0, a saponification number of 462, and an acid number of 2.35. This product remained completely clear after being stored for one week at 0 C.
  • EXAMPLE 3 Analogously to Example 1, 100 g. of myristic acid monoglyceride (diglyceride content: 8.8% by weight;
  • EXAMPLE 4 78 parts by weight of diacetyl monododecanoyl glycerol was mixed with 22 parts by weight of diacetyl monohexadecanoyl glycerol. The mixture remained completely clear after a longer period of storage at 0 C.
  • EXAMPLE 5 Ten parts by weight of diacetyl monohexadecanoyl glycerol, 40 parts by Weight of diacetyl monotetradecanoyl glycerol, and 50 parts by weight of diacetyl monododecanoyl glycerol were mixed with one another. The mixture remained completely clear after being stored at 0 C. for a longer period of time.
  • An oxidation-resistant glyceride mixture which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of to 99% by weight of diacetyl monododecanoyl triglyceride, up to 90% by weight of diacetyl monotetradecanoyl triglyceride, and up to 25% by weight of diacetyl monohexadecanoyl triglyceride.
  • An oxidation-resistant glyceride mixture which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with Water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride and up to 90% by weight of diacetyl monotetradecanoyl triglyceride.
  • An oxidation-resistant glyceride mixture which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 75 to 99% by weight of diacetyl monododecanoyl triglyceride and 1 to 25% by weight of diacetyl monohexadecanoyl triglyceride.
  • An oxidation-resistant glyceride mixture which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to 25% by weight of diacetyl monohexadecanoyl triglyceride, and up to 10% by weight of an acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms.
  • An oxidation-resistant glyceride mixture which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to 25% by weight of diacetyl monohexadecanoyl triglyceride, up to 10% by weight of an acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms, and up to 90% by weight of diacetyl monotetradecanoyl triglyceride.
  • An oxidation-resistant glyceride mixture which does not exhibit crystalline deposits of 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze'with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to 90% by weight of diacetyl monotetradecanoyl triglyceride, and up to 10% by weight of an acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms.
  • An oxidation-resistant glyceride mixture which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to by weight of diacetyl monotetradecanoyl triglyceride, up to 25% by weight of diacetyl monohexadecanoyl triglyceride, and suflicient diglycerides that the resultant glyceride mixture has a hydroxyl number of up to 20.
  • An oxidation-resistant glyceride mixture which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 75 to 99% by weight of diacetyl monododecanoyl triglyceride, 1 to 25% by weight of diacetyl monohexadecanoyl triglyceride, and sufiicient diglycerides that the resultant glyceride mixture has a hydroxyl number of up to 20.
  • An oxidation-resistant glyceride mixture which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to 25% by weight of diacetyl monohexadecanoyl triglyceride, up to 10% by weight of an acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms, and sufficient diglycerides that the resultant glyceride mixture has a' hydroxyl number of up to 20.
  • An oxidation-resistant glyceride mixture which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to 25 by weight of diacetyl monohexadecanoyl triglyceride, up to 10% by weight of an acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms, up to 90% by weight of diacetyl tetradecanoyl triglyceride, and sufficient diglycerides that the resultant glyceride mixture has a hydroxyl number of up to 20.
  • An oxidation-resistant glyceride mixture which does not exhibit crystalline deposits of 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to 90% by weight of diacetyl monotetradecanoyl triglyceride, up to 10% by weight of an acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms, and sufiicient diglycerides that the resultant glyceride mixture has a hydroxyl number of up to 20.
  • An oxidation-resistant glyceride mixture which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of: (a) 10 to 90% by weight of diacetyl monododecanoyl triglyceride and another triglyceride component selected from the group consisting of (b) up to 25% by weight of diacetyl monohexadecanoyl triglyceride, (c) up to 10% by weight of acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms, (d) up to 90% by weight of diacetyl monotetradecanoyl triglyceride and a combination of (b), (c), and (d); and (e) sufficient diglycerides that the resultant glyc- 3,748,265 5 6 eride mixture has

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (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)
  • Fats And Perfumes (AREA)

Abstract

GLYCERIDE MIXTURES RESISTANT TO OXIDATION AND LOW TEMPERATURES COMPRISING 10-99% BY WEIGHT OF DIACETYL MONOMONOHEXADECANOLY TRIGLCERIDE, AND/OR UP TO 90% BY MONOHEXADECANOYL TRIGLYCERIDE, AND/OR UP TO 90% BY WEIGHT OF DIACETYL MONOTETRADECANOYL TRIGLCERIDE, AS WELL AS OPTIONALLY UP TO 10% BY WEIGHT OF AN ACETYL DIALKANOYL TRIGLYCERIDE WHEREIN THE ALKANOYL GROUPS THEREOF HAVE 1216 CARBON ATOMS.

Description

United States Patent 3,748,265 OXIDATION- AND LOW TEMPERATURE-RESIST- ANT GLYCERIDES OF NATURAL FATTY AClDS Heinrich Biinger, Witten-Bommern, and Gustav Renclrhofi, Witten, Germany, assiguors to Dynamit Nobel Aktiengesellschaft, Troisdorf, Germany N0 Drawing. Filed Mar. 1, 1971, Ser. No. 119,828
lint. Cl. C091; 3/20 US. Cl. 252-]. 13 Claims ABSTRACT OF THE DISCLOSURE Glyceride mixtures resistant to oxidation and low temperatures comprising -99% by weight of diacetyl monododecanoyl triglyceride, up to 25% by weight of diacetyl monohexadecanoyl triglyceride, and/or up to 90% by Weight of diacetyl monotetradecanoyl triglyceride, as well as optionally up to 10% by weight of an acetyl dialkanoyl triglyceride wherein the alkanoyl groups thereof have 12- 16 carbon atoms.
Liquid glycerides of natural fatty acids are employed in a great variety of fields, for example in the pharmaceutical and cosmetic industries, in [food technology, as well as in the technical sector. In most cases, they must meet the requirements of being physiologically accetpable as well as nonfreezing, capable of readily dissolving fats and waxes, and having a low vapor pressure.
Glycerides are employed, for example, which contain bound therein also unsaturated fatty acids, in addition to saturated ones. Such glycerides are prone to autoxidation; they become more or less readily rancid in dependence on the external conditions (Neuwald, F.; Winkler, A.: J. Soc. Cosmetic Chemists 16 (1965), pp. 679-85). This phenomenon can be prevented by antioxidants; however, the addition of such agents is in many cases undesirable.
Furthermore, triglycerides of fully saturated fatty acids are known which are liquid at low temperatures (for example, German Pat. 944,394). However, the glycerides contain considerable proportions of [fatty acid residues of less than 12 carbon atoms. By minor splitting reactions taking place during use, for example by lipases, a typically soapy odor develops.
Also, liquid glycerides containing aceto groups have been described in the literature (The Journal of the American Oil Chemists Society 35 (1958), pp. 122-7). However, these glycerides, due to their composition, like wise exhibit the tendency toward rancidity or toward splitting off fatty acids causing an intensely soapy odor.
It has now been found that a triglyceride fulfills all practical requirements and does not exhibit the disadvantages of the triglycerides known heretofore, i.e. a triglyceride which is oxidation-resistant, does not liberate intensely soapy smelling fatty acids upon a splitting reaction, does not exhibit any crystalline deposits after being stored for a longer period of time at 0 C., and is not hydrolyzed upon contact with Water, if the molecule of such triglyceride exhibits two acetyl groups and one dodecanoyl group.
All of these properties are also retained if this triglyceride is present in a mixture with glycerides of a specific structure modified with respect to the higher fatty acid residue. The mixture component can be a triglyceride containing, in addition to two acetyl groups, the residue of a fatty acid exhibiting more than 12 carbon atoms. Also in this case, the formation of fatty acids of an intensely soapy odor is avoided during the occurrence of a splitting reaction. In view of the requirement that a liquid 3,?43,Z05 Patented July 24, 1973 "ice consistency must be present at 0 C., there is, in this case, merely a limitation with respect to the chain length of the acid residue, which latter is to have no more than 16 carbon atoms. Such mixtures can contain, in addition to diacetyl monododecanoyl glycerol, up to 25% by weight of diacetyl monohexadecanoyl glycerol or up to by weight of diacetyl monotetradecanoyl glycerol.
It is also possible to admix to the triglyceride with two acetyl groups and one dodecanoyl group in the molecule, as well as to the above-mentioned mixtures, up to 10% by weight of acetyl dialkanoyl glycerol, wherein the alkanoyl groups, in turn, can contain l2-16 carbon atoms.
Furthermore, such a number of diglycerides can be contained therein that a hydroxyl number of up to 20 results.
The glyceride of this invention can be produced, according to one process, by the esterification of lauric acid with excess glycerol and isolation of the thus-formed mono-glyceride by molecular distillation, whereupon an acetylation of the monoglyceride is connected with acetic anhydride to produce the triglyceride. Furthermore, the triglyceride of this invention can be obtained by the interesterifieation of tridodecanoyl glycerol with triacetin and separation of the reaction product by molecular distillation.
Since the glyceride of this invention can also retain its advantageous properties in a mixture with other glycerides, it is possible to make a suitable selection, during the manufacture thereof, among the technical fatty acid blends commercially available.
EXAMPLE 1 Lauric acid monoglyceride was enriched by molecular distillation from a lauric acid partial glyceride mixture This monoglyceride was pure, as determined by gas chromatography, and exhibited the following characteristics:
Melting point C 63.0 Acid number 0.88 Saponification number 207 Hydroxyl number 409 Fifty grams of this monoglyceride was refluxed with g. of acetic anhydride under normal pressure for two hours. Then the acetic acid and excess acetic anhydride were distilled off, at last under vacuum. Thereafter, steam was passed through the product for two hours at C. and 20 torr (mm. Hg). The product, after this step, exhibited a hydroxyl number of 0, an acid number of 0.8, and a saponification number of 467 (calculated value: 469). The refractive index at 20 C., measured by dylight, was 1.4475; the substance solidified at 2l.0 C. and boiled at 197 C. and 1.5 torr.
EXAMPLE 2 A lauric acid partial glyceride fraction obtained during molecular distillation with the following data: melting point, 60 C.; hydroxyl number, 381; saponification number, 214; acid number, 2.2; consisted, in accordance with analysis by gas chromatography, of 90.5% monoglyceride and 9.5% diglyceride. This fraction was acetylated in correspondence with Example 1, thus resulting in a product having a hydroxyl number of 0, a saponification number of 462, and an acid number of 2.35. This product remained completely clear after being stored for one week at 0 C.
EXAMPLE 3 Analogously to Example 1, 100 g. of myristic acid monoglyceride (diglyceride content: 8.8% by weight;
melting point: 69 0.; hydroxyl number: 330.0; saponification number: 117.5; acid number: 1.28) was reacted with 100 g. of acetic anhydride and then worked up. A mixture of 85 parts by Weight of the product (hydroxyl number: saponification number: 469; acid number: 0) with 15 parts by weight of diacetyl monododecanoyl glycerol remained completely clear after a longer period of storage at 0 C.
EXAMPLE 4 78 parts by weight of diacetyl monododecanoyl glycerol was mixed with 22 parts by weight of diacetyl monohexadecanoyl glycerol. The mixture remained completely clear after a longer period of storage at 0 C.
EXAMPLE 5 Ten parts by weight of diacetyl monohexadecanoyl glycerol, 40 parts by Weight of diacetyl monotetradecanoyl glycerol, and 50 parts by weight of diacetyl monododecanoyl glycerol were mixed with one another. The mixture remained completely clear after being stored at 0 C. for a longer period of time.
We claim:
1. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of to 99% by weight of diacetyl monododecanoyl triglyceride, up to 90% by weight of diacetyl monotetradecanoyl triglyceride, and up to 25% by weight of diacetyl monohexadecanoyl triglyceride.
2. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with Water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride and up to 90% by weight of diacetyl monotetradecanoyl triglyceride.
3. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 75 to 99% by weight of diacetyl monododecanoyl triglyceride and 1 to 25% by weight of diacetyl monohexadecanoyl triglyceride.
4. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to 25% by weight of diacetyl monohexadecanoyl triglyceride, and up to 10% by weight of an acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms.
5. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to 25% by weight of diacetyl monohexadecanoyl triglyceride, up to 10% by weight of an acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms, and up to 90% by weight of diacetyl monotetradecanoyl triglyceride.
6. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits of 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze'with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to 90% by weight of diacetyl monotetradecanoyl triglyceride, and up to 10% by weight of an acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms.
7. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to by weight of diacetyl monotetradecanoyl triglyceride, up to 25% by weight of diacetyl monohexadecanoyl triglyceride, and suflicient diglycerides that the resultant glyceride mixture has a hydroxyl number of up to 20.
8. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl tri-= glyceride, up to 90% by weight of diacetyl monotetradecanoyl triglyceride, and sufiicient diglycerides that the resultant glyceride mixture has a hydroxyl number of up to 20.
9. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 75 to 99% by weight of diacetyl monododecanoyl triglyceride, 1 to 25% by weight of diacetyl monohexadecanoyl triglyceride, and sufiicient diglycerides that the resultant glyceride mixture has a hydroxyl number of up to 20.
10. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to 25% by weight of diacetyl monohexadecanoyl triglyceride, up to 10% by weight of an acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms, and sufficient diglycerides that the resultant glyceride mixture has a' hydroxyl number of up to 20.
11. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to 25 by weight of diacetyl monohexadecanoyl triglyceride, up to 10% by weight of an acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms, up to 90% by weight of diacetyl tetradecanoyl triglyceride, and sufficient diglycerides that the resultant glyceride mixture has a hydroxyl number of up to 20.
12. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits of 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of 10 to 99% by weight of diacetyl monododecanoyl triglyceride, up to 90% by weight of diacetyl monotetradecanoyl triglyceride, up to 10% by weight of an acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms, and sufiicient diglycerides that the resultant glyceride mixture has a hydroxyl number of up to 20.
13. An oxidation-resistant glyceride mixture, which does not exhibit crystalline deposits at 0 C., does not liberate fatty acids having an intensely soapy odor when cleaved and does not hydrolyze with water, consisting essentially of: (a) 10 to 90% by weight of diacetyl monododecanoyl triglyceride and another triglyceride component selected from the group consisting of (b) up to 25% by weight of diacetyl monohexadecanoyl triglyceride, (c) up to 10% by weight of acetyl dialkanoyl triglyceride, the alkanoyl groups thereof having from 12 to 16 carbon atoms, (d) up to 90% by weight of diacetyl monotetradecanoyl triglyceride and a combination of (b), (c), and (d); and (e) sufficient diglycerides that the resultant glyc- 3,748,265 5 6 eride mixture has a hydroxyl number of up to 20, each OTHER REFERENCES weight percent being based on the total weight of the I. Am Oil Chemists, Soc March 1958 VOL XXXV glyceride mixtufe- No. 3, p. 122-127, Present Status of Acetoglycerides.
References Cited UNITED STATES PATENTS 5 GEORGE F. LESMES, Primary Examiner 2,091,988 9/1937 Hubbuch et al 260-106 W- X J Assistant i er. 3,006,771 10/1961 Babayon 99 11s 2,745,749 5/1956 Peoge 61:31. 99 -11s 2,480,332 8/1949 Little 260--410.8 260-4103
US00119828A 1971-03-01 1971-03-01 Oxidation- and low temperature-resistant glycerides of natural fatty acids Expired - Lifetime US3748265A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US11982871A 1971-03-01 1971-03-01

Publications (1)

Publication Number Publication Date
US3748265A true US3748265A (en) 1973-07-24

Family

ID=22386632

Family Applications (1)

Application Number Title Priority Date Filing Date
US00119828A Expired - Lifetime US3748265A (en) 1971-03-01 1971-03-01 Oxidation- and low temperature-resistant glycerides of natural fatty acids

Country Status (1)

Country Link
US (1) US3748265A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0101046A1 (en) * 1982-08-11 1984-02-22 EASTMAN KODAK COMPANY (a New Jersey corporation) Methods, compositions and elements for the determination of lipase
US4555483A (en) * 1982-08-11 1985-11-26 Eastman Kodak Company Methods, compositions and elements for the determination of lipase
EP1624014A1 (en) * 1999-08-19 2006-02-08 Danisco A/S Specific acylated gylcerol compounds for plasticisers in polymers and process for their preparation
CN108623459A (en) * 2018-06-25 2018-10-09 长沙市如虹医药科技股份有限公司 A kind of preparation method of diacetyl glycerin monostearate

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0101046A1 (en) * 1982-08-11 1984-02-22 EASTMAN KODAK COMPANY (a New Jersey corporation) Methods, compositions and elements for the determination of lipase
US4555483A (en) * 1982-08-11 1985-11-26 Eastman Kodak Company Methods, compositions and elements for the determination of lipase
EP1624014A1 (en) * 1999-08-19 2006-02-08 Danisco A/S Specific acylated gylcerol compounds for plasticisers in polymers and process for their preparation
EP2011819A1 (en) * 1999-08-19 2009-01-07 Danisco A/S Process
CN108623459A (en) * 2018-06-25 2018-10-09 长沙市如虹医药科技股份有限公司 A kind of preparation method of diacetyl glycerin monostearate

Similar Documents

Publication Publication Date Title
Jacobsberg et al. Studies in palm oil crystallization
KR830003571A (en) Preparation of surfactant containing sucrose ester
US5155246A (en) Wool-wax substitutes
US20020144455A1 (en) Non sooting candle composition
JPH025385B2 (en)
US2206168A (en) Process for manufacturing fatty esters
US1558299A (en) Mixed esters of lower and higher fatty acids and process of making same
US3748265A (en) Oxidation- and low temperature-resistant glycerides of natural fatty acids
US3494944A (en) Process for vacuum distilling randomly interesterified triglycerides to produce novel triglyceride fractions
US3145109A (en) Shortening product and method of making thereof
US2874175A (en) Process for making fatty acid diglyceride, diesters of dibasic acids
JPS59106257A (en) Margarine fat mixture
Mattson et al. Esterification of hydroxy compounds by fatty acid anhydrides
US2667418A (en) Hard butter composition
Feuge et al. Modification of vegetable oils. XIV. Properties of aceto‐oleins
Eckey et al. Directed interesterification in glycerides. Reaction in presence of added glycerol
US2914546A (en) Interesterified mixed glyceryl esters
US3360533A (en) Process for the improved winterization of oil
Feuge et al. Modification of vegetable oils. IX. Purification of technical monoglycerides
CA1093974A (en) Perfume compositions containing esters of 3,5,5- trimethylhexanoic acid
US2478354A (en) Preparation of partial esters
US3027260A (en) Mayonnaise
US3766227A (en) Hydrolysis resistant acetoglycerides which are solid at room temperature
US3220924A (en) Process for the preparation of tropicstable suppository masses and the product thereof
GB808634A (en) Preparation of mixed glycerol ester compositions