Colloid systems and wetting agents; subcombinations thereof; pro – Continuous liquid or supercritical phase: colloid systems;... – Aqueous continuous liquid phase and discontinuous phase...
Patent
1997-11-12
2000-10-10
Lovering, Richard D.
Colloid systems and wetting agents; subcombinations thereof; pro
Continuous liquid or supercritical phase: colloid systems;...
Aqueous continuous liquid phase and discontinuous phase...
549253, 549233, 562888, B01F 1736, C07D30756
Patent
active
061302570
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to compositions comprising mixtures of two enantiomeric forms of diacyl tartaric anhydride and mixtures obtainable by reacting an organic compound with a mixture comprising two enantiomeric forms of diacyl tartaric anhydride. The invention also relates to a method for the preparation of such enantiomeric mixtures, starting from a mixture comprising D-tartaric acid and L-tartaric acid.
DESCRIPTION OF RELATED ART
Diacyl tartaric anhydride compounds (such as diacetyl tartaric anhydride, herein after referred to as "DATA"), are versatile chemical intermediates. Such compounds can be used, inter alia, for the manufacture of a large group of emulsifiers for food use, for example by reacting DATA with a fatty acid monoglyceride ester or the corresponding diester or any mixture thereof.
Diacyl tartaric anhydride compounds are generally prepared by reacting tartaric acid with a fatty acid anhydride (having preferably between 1 to 4 carbon atoms). Tartaric acid exists in three basic structures: L-(+)-tartaric acid (natural tartaric acid) and D-(-)-tartaric acid, which are both optical active, and the meso-form, which is not optical active. Mixtures of these forms also exist, e.g. the racemic mixture D,L-tartaric acid. Tartaric acid is a white solid material (at ambient conditions).
At present, diacetyl tartaric anhydride (DATA) is prepared by reacting tartaric acid with acetic anhydride. Both L-tartaric acid, D-tartaric acid as well as D,L-tartaric acid are not well soluble in acetic anhydride. However, once L-tartaric acid starts to react, it is solubilized in acetic anhydride very quickly. On the other hand, D-tartaric acid and D,L-tartaric acid are not well solubilized. For this reason, DATA is prepared up till now starting from L-(+)-tartaric acid, and consequently, diacetyl-L-tartaric anhydride (L-DATA) is obtained.
SUMMARY OF THE INVENTION
Thus, in the conventional reactions for the preparation of diacyl tartaric anhydride starting from tartaric acid and a fatty acid anhydride (having preferably between 1 to 4 carbon atoms), D-tartaric acid and D,L-tartaric acid (the racemic mixture) cannot be used. This is a disadvantage, since it limits the choice of starting materials. Additionally, when L-DATA is used in the preparation of emulsifiers for application of foodstuffs (as set out above), such emulsifiers can generally not be used in applications where all food products and ingredients need to be kosher. Therefore, there is a need for a process in which it would be possible to prepare diacyl tartaric anhydrides by reacting tartaric acid with fatty acid anhydrides (having preferably between 1 to 4 carbon atoms), and wherein it is possible to use equally well L-tartaric acid, D-tartaric acid as well as all mixtures thereof, such as racemic mixtures.
It has now been found that such a process is possible, when at least a part of the reaction between tartaric acid and a fatty acid anhydride (having preferably between 1 and 4 carbon atoms) is carried out under dielectric heating conditions. Preferably, at least the first part of the reaction should be carried out under dielectric heating conditions, and more preferably dielectric heating conditions should be employed during the entire reaction time. As an alternative, the dielectric heating may be employed intermittently.
In Synthetic Communications, 23(4), 419-424 (1993), it is reported that organic reactions can be carried out under dielectric heating (by a microwave). However, its use in connection to the preparation of diacyl tartaric anhydrides is neither mentioned nor suggested, and additionally, its use in connection to reactions involving stereo isomers is also not reported therein.
DESCRIPTION OF PREFERRED EMBODIMENTS
A preferred fatty acid anhydride for the above purpose is acetic anhydride, yielding upon reaction with tartaric acid diacetyl tartaric anhydride (DATA).
It is possible to prepare compositions comprising diacyl tartaric anhydride, which diacyl tartaric anhydride is a mixture of L-di
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Villemin et al., "Clay Catalysis: a Convenient and Rapid Formation of Anhydride from Carboxylic Acid and Isopropenyl Acetate under Microwave Irradiation" Synthetic Communications, 23(4), 419-424 (1993).
Coenders Peter Joannes
Galema Saskia Alexandra
Gombert Johannes Durk
Meer Anna Sophie E ter
Lovering Richard D.
Metzmaier Daniel S.
Quest International B.V.
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