Dsm IP Assets B.v.

Roche Vitamins Inc.

Dsm Assets B.v.

Dsm IP Assets B.v. a Netherlands Corporation

Angela Wildermann

Werner Bonrath

Werner Pietzonka

Juan Ramon Herguijuela

Thomas Wolf

Thomas Netscher

Raphael Beumer

Silke Dorn

Yann Foricher

Peter Ruckstuhl

Christine Mendrok-Edinger

René Tobias Stemmler

Peter Riebel

Nadine Greiner

Gunther Hellmann

The present invention relates to propanediol monoacetate mononitrate as well as the use thereof as antimicrobial agent, in particular for cosmetic applications.

Propanediol monoacetate mononitrate

The present invention is directed to a process for the manufacture of methyl limonitrile comprising a mixture of 3,7-dimethyl-2,6-nonadiene nitrile, 3,7-dimethyl-3,6-nonadiene nitrile and 7-methyl-3-methylene-6-nonene nitrile comprising the following steps: a) reacting 6-methyl-5-octen-2-one with cyano acetic acid and removing carbon dioxide and water, wherein the reaction and the removal of carbon dioxide and water are performed in the presence of a base and a co-base 1 in an organic solvent, and wherein the organic solvent is a solvent which forms a heteroazeotrop with water; b) removing the solvent and the base of the reaction mixture obtained after having performed step a) or step c) by distillation to obtain a reaction mixture, whereby this step may optionally be performed in the presence of a co-base 2; c) isomerizing the reaction mixture obtained after having performed step a) or step b) to obtain an isomerized reaction mixture in the presence of a co-base 2; whereby step b) can be performed before or after step c).

Process for the manufacture of methyl limonitrile

The present invention relates to a process of a cis/trans isomerization of an unsaturated compound A being selected from the group consisting of unsaturated ketones, unsaturated ketals, unsaturated aldehydes, unsaturated acetals, unsaturated carboxylic acids, esters of an unsaturated carboxylic acid and amides of an unsaturated carboxylic acid using nitrogen monoxide as cis/trans isomerization catalyst. It has been observed that the isomerization is very efficient and fast.

Nitrogen monoxide as cis/trans isomerization catalysts for unsaturated compounds

The present invention is directed to a process for the manufacture of methyl limonitrile comprising a mixture of 3,7-dimethyl-2,6-nonadiene nitrile, 3,7-dimethyl-3,6-nonadiene nitrile and 7-methyl-3-methylene-6-nonene nitrile comprising the following steps: a) reacting 6-methyl-5-octen-2-one with cyano acetic acid and removing carbon dioxide and water, wherein the reaction and the removal of carbon dioxide and water are performed in the presence of a base and a co-base in an organic solvent, wherein the base is pyridine, wherein the co-base is 1,4-diamino butane, and wherein the organic solvent is a solvent which forms a heteroazeotrop with water; b) removing the solvent and pyridine of the reaction mixture obtained after having performed step a) or step c) by distillation to obtain a reaction mixture; c) isomerizing the reaction mixture obtained after having performed step a) or step b) to obtain an isomerized reaction mixture; whereby step b) can be performed before or after step c).

A process for the rectification of mixtures of high-boiling air- and/or temperature-sensitive substances which require a high separation efficiency is proposed, in particular a process for the working-up of a VE- or VEA-containing product stream. The process includes a first purification stage to separate low-boiling products and unspecified isomers of the useful product from the product stream virtually without loss of useful product and a second purification stage for removing the useful product in a stream having a purity of &#x3e;97% by weight and a further stream having a purity of &#x3e;92% by weight.

Process for the rectification of mixtures of high-boiling air- and/or temperature-sensitive useful products

The present invention relates to novel processes for the manufacture of chroman derivatives such as &#x3b1;-tocopherol (TCP) and alkanoates thereof, especially &#x3b1;-tocopheryl acetate (TCPA), whereby at least one step of the processes is carried out in the presence of a Lewis acid or a mixture of a Lewis acid with a Bronsted acid as the catalyst under pressure, preferably at an absolute pressure of at least 1.1 bar. As starting materials for the manufacture of TCP and its alkanoates either a mixture of 2,3,5-trimethylhydroquinone (TMHQ) or 2,3,6-trimethylhydroquinone-1-alkanoate (TMHQA) and a compound selected from the group consisting of phytol (PH), isophytol (IP) and (iso)phytol derivatives or 2-phytyl-3,5,6-trimethyl-hydroquinone (PTMHQ)/3-phytyl-2,5,6-trimethylhydroquinone-1-alkanoate (PTMHQA) and/or an isomer thereof are used. Suitable Lewis acids are indium(III) salts and scandium(III) salts. Suitable acid mixtures are iron/iron(II) chloride/hydrogen chloride and zinc(II) chloride/hydrogen chloride.

Process for the manufacture of chroman derivatives, especially &#x3b1;-tocopherol and alka-noates thereof

According to the invention, a process for the rectification of mixtures of high-boiling air- and/or temperature-sensitive substances which require a high separation efficiency is proposed, in particular a process for the working-up of a VE- or VEA-containing product stream. The process is characterized in particular in that, in a first purification stage, low-boiling products and unspecified isomers of the useful product are separated from the product stream virtually without loss of useful product and that, in a second purification stage, the useful product is removed in a stream having a purity of &#x3e;97% by weight and a further stream having a purity of &#x3e;92% by weight. A preferred embodiment of the process serves for working up VEA, in which the loss of useful product in the first purification stage is less than 5%, based on that amount of VEA in the feed which is added to the purification stage per unit time. Furthermore, the first purification stage may comprise a rectification column (), from the top () of which the low-boiling products and the unspecified isomers of VEA are taken off, a stream containing the useful product in purified form being taken off at the side () and/or at the bottom () of the column ().

A rectification column and system for the working-up of a vitamin E (VE)- and/or vitamin E acetate (VEA)-containing product stream includes purification of a vitamin E-containing product stream, acetylation of at least a part of the purified vitamin E and purification of at least a part of the acetylated vitamin E, the purification of vitamin E and vitamin E acetate preferably being effected by distillation, for example rectification.

Process for the working-up of a vitamin E- and vitamin E-acetate-containing mixture or product stream

The invention relates to a process for the working-up of a vitamin E (VE)- and/or vitamin E acetate (VEA)-containing product stream, which is substantially characterized by purification of a vitamin E-containing product stream, acetylation of at least a part of the purified vitamin E and purification of at least a part of the acetylated vitamin E, the purification of vitamin E and vitamin E acetate preferably being effected by distillation, for example rectification. A preferred process according to the invention is characterized in that a vitamin E-containing product stream is fed to a first rectification column (), low-boiling products and unspecified isomers of vitamin E being taken off at the top () of this first rectification column virtually without loss of useful substance, and a purified, vitamin E-containing stream being taken off at the side () and/or at the bottom () of the rectification column (), at least a part of the side take-off or of the bottom take-off or at least a part of the side and bottom take-off is passed, for acetylation of vitamin E, into an acetylation stage (), at least a part of the product stream emerging from the acetylation stage is passed into a second rectification column () or is taken off as useful product having a purity of &#x2267;92% by weight, and in a second rectification column, the VEA useful product is obtained as a side take-off having a purity of &#x2267;97% by weight.

Process for the working-up of a vitamin E- and vitamin E-acetate- containing mixture or products stream

The present invention relates to a new method for a safe transport of ethyne in form of &#x3b1;-alkynols as precursors for ethyne. The new method comprises three steps. In a first step the synthesis of the &#x3b1;-alkynol(s) is performed by reacting ethyne with (a) carbonyl compound(s). The second step comprises the transport of the resulting &#x3b1;-alkynol(s) in a safe manner, whereas the safety requirements for this transport are not as high as for ethyne because &#x3b1;-alkynol(s) are normally classified for transportation as hazardous class 3. In the third step the &#x3b1;-alkynol(s) can be cleaved and the ethyne and the carbonyl compound(s) can be obtained in the cleavage reaction and can be separated to yield pure products for further applications.

Transport of ethyne in form of &#x3b1;-alkynols as ethyne precursors

According to the invention, a process for the rectification of mixtures of high-boiling air- and/or temperature-sensitive substances which require a high separation efficiency is proposed, in particular a process for the working-up of a VE- or VEA-containing product stream. The process is characterized in particular in that, in a first purification stage, low-boiling products and unspecified isomers of the useful product are separated from the product stream virtually without loss of useful product and that, in a second purification stage, the useful product is removed in a stream having a purity of &#x3e;97% by weight and a further stream having a purity of &#x3e;92% by weight. A preferred embodiment of the process serves for working up VEA, in which the loss of useful product in the first purification stage is less than 5%, based on that amount of VEA in the feed which is added to the purification stage per unit time. Furthermore, the first purification stage may comprise a rectification column (), from the top (Ia) of which the low-boiling products and the unspecified isomers of VEA are taken off, a stream containing the useful product in purified form being taken off at the side () and/or at the bottom (Ib) of the column ().

Process for the rectification of mixtures of high-boiling air-and/or temperature-sensitive useful products

The present invention relates to a process for the manufacture of alkenylated aromatic compounds featuring at least one hydroxy group, their ring-closure reactions to 5 chroman derivatives, as well as the acylation of the latter and the aromatic compounds featuring at least one hydroxy group themselves. The present invention relates especially to a process for the manufacture of tocol, tocopherols and their alkanoates such as (x-tocopherol (TCP) and alkanoates (TCPA) thereof, preferably (x-toeopheryl acetate (TCPAc). The processes of the present invention are characterized in that at least one step of the processes is carried out in the presence of an indium salt as the catalyst.

Process for the manufacture of alkenylated hydroxylated aromatic compounds, of chroman compounds and of their acylated derivatives

A process is disclosed for the catalyzed isomerization of a Z-isomer of a vitamin A compound or of a mixture of several of such isomers into a mixture of the corresponding all-E- and 13-Z-isomers of this vitamin A compound. The process utilizes nitrogen monoxide or a gas mixture containing nitrogen monoxide as the isomerization catalyst. Vitamin A acetate or vitamin A acid is preferably used as the vitamin A compound. The thus-produced all-E vitamin A and its alkanoyl esters have of all isomers by far the highest biological activity and are accordingly almost exclusively used in human and animal nutrition. The 13-Z-vitamin A compounds in turn play an important role as pharmaceutically active substances.

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Bad Säckingen, Germany

Angela Wildermann