EP2061741A1

EP2061741A1 - Method for producing 1,2-propaniol

Info

Publication number: EP2061741A1
Application number: EP07802687A
Authority: EP
Inventors: Alfred Westfechtel; Norbert Klein; Elke Grundt; Teresa Alexandre
Original assignee: Cognis Oleochemicals GmbH
Current assignee: Emery Oleochemicals GmbH
Priority date: 2006-08-17
Filing date: 2007-08-17
Publication date: 2009-05-27
Also published as: WO2008020077A1

Abstract

The invention relates to a method for producing 1,2-propandion with a purity of at least 98%, wherein as a first step, glycerin in the presence of a heterogeneous copper containing catalyst, particularly a heterogeneous copper-chrome containing catalyst, is continually hydrogenated, wherein the glycerin reacts to 95% at the most, the reactive mixture obtained in the first step is subjected to a distillation. The invention further relates to a method for producing a compound containing at least one ether group, at least one ester group, at least one amino group or at least one urethane group or at least two thereof, the obtained compound by this method containing at least one ether group, at least one ester group, at least one amino group or at least one urethane group or at least two thereof, a method for producing a compound, the compound obtainable by this method, the use of a hydrogenation process and the use of a compound.

Description

Process for the preparation of 1,2-propanediol

The invention relates to a process for the preparation of 1,2-propanediol. Also proposed is a process for preparing a compound comprising at least one ether group, at least one ester group, at least one amino group or at least one urethane group or at least two thereof, the compound obtainable by this process comprising at least one Ether group, at least one ester group, at least one amino group or at least one urethane group or at least two thereof, a process for preparing a process for preparing a composition, the composition obtainable by this process, the use of a hydrogenation process and the Use of a connection.

The glycerol, which is abundantly available as an industrial raw material due to fats and oils, can serve as the basis for various syntheses. Mention should be made in this context, on the one hand dehydration (elimination of water) to acetol (see, for example, DE-A-41 28 692 / Henkel, Fleckenstein et al.) And on the other hand, the dehydration proceeds to 1,2-propanediol with elimination of water.

1,2-Propanediol is an industrially interesting raw material. It is used in a variety of applications, namely in the food industry, as a solvent for dyes and flavors, as humectants for tobacco, in cosmetics, as a component of brake and hydraulic fluids, antifreezes, lubricants in refrigerators, as a solvent for greases , Oils, resins, waxes, dyes, etc. It also serves as a starting material for the manufacture of other products. By esterification and / or etherification, it is possible to obtain numerous products which can be used as solvents, for syntheses, as plasticizers, thickeners, emulsifiers and the like. In the majority of the applications mentioned, the purity of the 1,2-propanediol plays a role. 1,2- Propanediol is usually produced industrially by hydration of propylene oxide. Although the abovementioned production of 1,2-propanediol by hydrogenation of glycerol has been described several times, it has not yet been able to establish itself in industrial practice.

The oldest patent document known to the Applicant, which describes the hydrogenation of glycerol to 1,2-propanediol, is German Patent DE-C-524 101 to IG Farben. According to Example 1 of this document, a hydrogen stream containing 1 to 1.5 vol .-% glycerol, passed at 200 to 210 ⁰ C over a catalyst which is applied to glass beads. In this case, a liquid is obtained, which is fractionally distilled after removal of the water formed in the hydrogenation. The reaction of glycerol was almost complete. In the distillation, a mixture of 1,2-propanediol and propyl alcohol was obtained. The yield of 1,2-propanediol was reported as 70%.

DE-C-541 362 discloses the hydrogenation of polyoxy compounds. In this case, liquid or solid polyoxy compounds in aqueous solution or suspension are treated with hydrogen in the presence of catalysts. In Example 1, glycerin and a nickel catalyst are treated in a bomb at 200 to 240 ⁰ C and a pressure of 100 atm with hydrogen. Thus, it is a batch process, ie a discontinuous hydrogenation, wherein the catalyst is slurried in powder form in the liquid glycerol. From the statement that the calculated amount of hydrogen was taken up after 4 hours, it will be clear to the person skilled in the art that glycerol was evidently quantitatively reacted.

For a long time, the subject of glycerol hydrogenation to 1,2-propanediol was apparently broke. Only about 50 years later, it was taken up again:

Montassier et al. report in Heterogeneous Catalysis and Fine Chemicals (1988, Elsevier, Amsterdam, pages 165-170) that the hydrogenation of glycerol in present of Ru, Ni, Rh or Ir-based catalysts to hydrocarbons, especially methane leads. With Raney copper as catalyst, however, a mixture of 1,2-propanediol, ethylene glycol and carbon dioxide is obtained.

EP-AO 523 014 and EP-AO 523 015 (Novamont) address the problem of the lack of selectivity of glycerol hydrogenation to 1,2-propanediol in that they are based on ruthenium or zinc-copper based catalysts in very dilute aqueous medium deploy. Nevertheless, the selectivity leaves much to be desired. Namely, according to the examples of EP-A-0 523 015 (use of a zinc-copper catalyst) in the hydrogenation of glycerol in addition to propylene glycol, large amounts of ethylene glycol and also significant amounts of lactic acid are formed. According to the examples of EP-A-0 523 014 (use of a sulfide-modified ruthenium catalyst), in addition to propylene glycol, very large amounts of ethylene glycol are formed in the hydrogenation of glycerol. In addition, a dilution of the raw material to be used (glycerol) with water is technically unsatisfactory because this water must then be removed from the reaction mixture.

DE-A-43 02 464 of 1993 (Henkel, Fleckenstein et al.) Describes the continuous hydrogenation of glycerol in the presence of a specific heterogeneous catalyst. Preferably, a copper-containing catalyst is used, in particular copper chromite. According to the embodiments, glycerol was substantially quantitatively reacted (glycerol content in the reaction mixture below 0.1%), only 3 of the total of 10 examples operated with a partial conversion of glycerol (Examples 1, 3 and 9). Although analytical data were given for all the reaction mixtures of the examples, the mixtures were not worked up. Thus, the technical teaching of DE-A-43 02 464 can be seen in the fact that it shows the basic suitability of copper-containing heterogeneous catalysts for the hydrogenation of glycerol to 1,2-propanediol. It does not include the teaching that a partial hydrogenation of glycerol followed by distillation to give a 1,2-propanediol with very particular intrinsic professional profile. The document noted on page 3, lines 16/17 only that would be deducted for working up the reaction mixture obtained in the hydrogenation; the purely optional possibility of "further processing steps" is mentioned only marginally, without discussing in any way how such a work-up would look like and whether there are processing steps that would be of particular relevance.

According to US Pat. No. 5,616,817 (BASF, Schuster and Eggersdorfer) of 1995, the glycerol hydrogenation is carried out such that on the one hand glycerol having a water content of up to 20% by weight and on the other hand special catalysts (containing 40-70%) Co, 10-20% Mn, 0-10% Mo and 0-10% Cu). Glycerol is completely converted. However, even with the specific catalyst disclosed here, the limits of selectivity are still encountered. This will become immediately clear to the person skilled in the art if he considers the two exemplary embodiments. In Example 1, the reaction mixture contains 95.8% 1,2-propanediol and 3.2% n-propanol, in Example 2 the reaction mixture contains 92% 1,2-propanediol and 4.3% n-propanol.

In US-A-6,479,713 (Battelle Memorial Institute) from 2002 describes the hydrogenation of sugars or sugar alcohols, wherein special rhenium-containing multimetal catalysts are used. As a possible raw material that can be used for hydrogenation, glycerol is mentioned in the description. Tables 2-4 summarize experimental results where glycerol is hydrogenated in the presence of such catalysts. It is striking that although 1,2-propanediol is the main product of the hydrogenation, but very large amounts of ethylene glycol and lactate are formed. If a base was not added to the glycerol used, 1,3-propanediol was added as an additional undesired by-product (column 11, lines 49-51). The results of glycerol hydrogenation according to US-A-6,479,713 are therefore considered to be rather unsatisfactory.

- A - Suppes et al. in WO-A-2005/095536 and in Applied Catalysis A: General 281 (2005), pages 225-231, deal with the hydrogenation of glycerol in "mild" conditions by 200 ⁰ C and with the production of 1,2- Propanediol in two steps, namely the production of acetol from glycerol, followed by hydrogenation of the acetol to 1,2-propanediol.

The object of the present invention was to provide a novel process for the preparation of 1,2-propanediol by hydrogenation of glycerol.

The 1,2-propanediol thus prepared should be distinguished by a high purity, in particular a purity of at least 98% and preferably of at least 99%.

In addition, the 1,2-propanediol thus prepared should be of the highest possible quality, which means that it should in no case have an unpleasant and / or strong odor but at most a slight odor and should preferably be odorless.

It was also an object of the present invention to provide 1,2-propanediol-based ester or ether compounds which likewise do not have an unpleasant and / or strong odor, but at most have a slight odor and should preferably be odorless.

The aforementioned complex object has been solved in an excellent manner by the method according to the invention described below.

The invention relates to a process for the preparation of 1,2-propanediol having a purity of at least 98%, wherein

In a first step, glycerol in the presence of a heterogeneous copper-containing catalyst, in particular a heterogeneous copper-chromium -containing catalyst - continuously hydrogenated, glycerol being at most 95 wt .-%, preferably at most 90 wt .-%, even more preferably at most 85 wt .-%, more preferably at most 80 wt .-%, moreover even more preferred to at most 75% by weight, and most preferably to at most 70% by weight, and that in the first

Step obtained reaction mixture

In a second step, subjected to a distillation in which preferably the 1,2-propanediol formed in the first step is obtained as distillate.

The weight percentages used in the present invention are determined by gas chromatographic determinations by integrating the areas of the signals. For calibration and verification of the measurements, the weight percentages were confirmed by distillation and weighing of the individual components from a sample measured by gas chromatography.

A purity of at least 98% is understood to mean that after the process according to the invention has been carried out after passing through both steps (ie hydrogenation and distillation), a product is obtained whose content of 1,2-propanediol is at least 98%. The purity is determined by gas chromatography (area percent).

In a preferred embodiment, the two steps of the process according to the invention are carried out in such a way that the purity of the target product 1,2-propanediol is at least 99%.

It should be expressly stated that the overall process for the preparation of 1,2-propanediol according to the inventive method comprises two steps, namely • the hydrogenation of glycerol under the specified conditions and The distillation of the hydrogenation effluent obtained in the first step for the separation of water and the reduction of the by-products formed in the hydrogenation.

That with this combination of steps, such a success is achieved and the above complex task can be solved is not trivial and was not foreseeable for the expert.

In this context, the following is informative: if one carries out the hydrogenation of glycerol in a quantitative manner, one obtains hydrogenation processes that almost stink. If subsequently such hydrogenation processes (ie, glycerine obtained with complete hydrogenation) are distilled, it is found that the fractions of 1,2-propanediol thus obtained still have an unpleasant odor. However, if the hydrogenation is carried out in accordance with the invention such that the glycerol used is only partially hydrogenated and then the hydrogenation processes thus obtained are distilled, fractions are obtained which have no or at least a significantly low unpleasant odor.

The Applicant's investigations indicate that those odor carriers which are formed in the process according to the invention with the partial conversion of glycerol as indicated above and those odor carriers which are obtained with complete conversion of glycerol, although partly identical, but partly different, and Moreover, they are formed to varying degrees, with the result that they can be removed to varying degrees by distillation. And here is the inventive method of a procedure in which glycerol is quantitatively hydrogenated and then distilled, far superior. This surprising finding constitutes the essence of the teaching of the present invention and could not be inferred by the skilled person from the prior art nor was it suggested by prior art documents. Incidentally, it has been found that in the process according to the invention with the partial hydrogenation mentioned in step 1, a lower content of the by-product ethylene glycol which is difficult to remove by distillation and is undesirable.

Preferably, the first step of the process according to the invention (hydrogenation) is carried out in the presence of less than 20% by weight, more preferably less than 10% by weight, even more preferably less than 5% by weight, based on the amount by weight of used Glycerol, an organic solvent, wherein the implementation of the method in the complete absence of an organic solvent is most preferred.

The process according to the invention is carried out in the presence of a heterogeneous copper-containing catalyst. It is particularly preferred to use a heterogeneous copper-chromium-containing catalyst. It is particularly preferred to use a copper chromite catalyst containing preferably 30 to 40 wt .-% copper, 23 to 30 wt .-% chromium, based in each case on the oxidic catalyst composition, and, if desired, further transition metals in the form of their oxides. In one embodiment, such a copper chromite catalyst may contain from 1 to 7% by weight, in particular from 1.5 to 3% by weight, of barium, based on the oxidic catalyst mass. In one embodiment, the catalyst contains from 32 to 38% by weight of copper, based on the oxidic catalyst composition, of from 26 to 30% by weight of chromium, from 1.5 to 3% by weight of barium, from 0.5 to 2% by weight. Silicon and additionally 1 to 5, preferably 2 to 3 wt .-%, manganese, zirconium and / or cerium, based on the oxidic catalyst composition. In yet another embodiment, the catalyst is a copper chromite catalyst containing 35 to 55 wt%, preferably 40 to 50 wt% copper, 35 to 55 wt%, preferably 40 to 50 wt% chromium, in each case based on the oxidic catalyst mass, and optionally further Erdalkali- or transition metals, in particular barium and manganese, in the form of their oxides. These catalysts and their production processes are described in detail in EP-AO 254 189. As a concrete example of a suitable catalyst, mention may be made of a catalyst which contains about 47% by weight of CuO, 46% by weight of Cr ₂ O ₃ , 4% by weight of MnO ₂ and 2% by weight of BaO. This catalyst and its production process are also described in detail in EP 254 189 A2. The disclosure contained therein, in particular with regard to the catalysts and the preferred manner of their preparation is hereby incorporated by reference, and the information given there should also be part of the present application.

It is further preferred that the catalyst has a high surface area and porosity, so that a high activity and selectivity as well as a particularly long useful life for technical applications is achieved. Thus, it is advantageous if the catalyst used has a specific surface area in the range from 20 to 100 m ² / g, preferably 70 to 80 m ² / g.

The first step of the process according to the invention is preferably carried out by using hydrogen diluted or undiluted for hydrogenation, preferably at pressures in the range from 20 to 300 bar, in particular at 100 to 250 bar, and at temperatures in the range of 150 ⁰ C to 280 ⁰ C, in particular 180 to 220 ⁰ C, works. In the continuous mode of operation, glycerol is passed in vapor or liquid form over a fixed catalyst bed. Preferably, a molar ratio of hydrogen to glycerol in the range of 2 to 500 is set, wherein excess hydrogen is optionally circulated. This means that the flow rate of hydrogen gas, measured in moles H ₂ / hour, 2- to 500 times higher than the flow rate of glycerol, measured in moles of glycerol / hour. A preferred range of the conversion ratio is 30: 1 to 200: 1.

The first step of the process according to the invention (hydrogenation) can be carried out in similar reactors used for the preparation of fatty alcohols by hydrogenation of fatty acid methyl ester or directly from triglycerides and are known and which are preferably fixed bed reactors. The first step of the process according to the invention (hydrogenation) is preferably carried out in isothermally operated tubular reactors or tube bundle reactors. It is also conceivable to use reactors which have thermoplates as components. Both in the tube bundle reactors and in the reactors, which have thermoplates, the catalyst may be introduced in the form of a fixed catalyst bed or be applied as a coating on the inside of the tubes or thermoplates. The reaction parameters temperature and pressure can be adapted to the respective catalyst activity. The heat of reaction is largely dissipated via the reactor wall (in the case of use of tube bundle reactors via the walls of the reaction tubes used and in the case of use of reactors with thermoplates on the thermal sheets), so that a virtually isothermal driving is possible. If cooling of the reactor via air is not possible, then the reactor can optionally be cooled by using a suitable coolant, wherein with the use of tube bundle reactors this coolant flows along the reaction tube and when using reactors with thermoplates through the flow paths within the thermoplates , As coolant are for example water, Wärmeträ- gerflüssigkeiten as ^® Marlothem and salt melts. Furthermore, it is particularly preferred for the hydrogenation to be carried out by passing liquid glycerol in trickle bed in cocurrent or countercurrent with hydrogen over a catalyst fixed bed. In another embodiment, the reaction tubes are used Glycerol is fed under a back-mixing at least partially inhibiting measures with an LHSV (Liquid Hourly Space Velocity) expressed in m ³ / h glycerol per m ³ catalyst volume) in a range of 0.1 to 5 h ^-1 more preferably in a range of 0.2 to 3 h ^"1 and beyond Favor in a range of 0.3 to 2 ^{h" 1} through the catalyst bed in the reaction or to the pipes. When the back-mixing is at least partially preventing measures are in principle all measures known to the person skilled in the art and suitable for this purpose, such as suitable tube cross sections or tube cross-sectional length ratios, which are usually selected as a function of the flow conditions usually prevailing during operation of the reactor.

Further details of an advantageous embodiment of the catalyst used for the hydrogenation can be found, inter alia, EP-AO 334 118, whose disclosure content is hereby introduced as a reference, in particular with regard to avoiding backmixing in the reactor, the advantageous volume loading of the reactor and the advantageous surface loading of the reactor and forms part of the disclosure of the present invention.

In addition to the use of a single fixed bed reactor as the hydrogenation reactor and at least two interconnected fixed bed reactors can be used, in which case the hydrogen is passed through the at least two fixed bed reactors in succession, without the emerging from the reactors and entering the subsequent reactors gas cooled becomes. Such a process is described, for example, in EP-A-0 515 485, the disclosure of which is hereby incorporated by reference as a reference with regard to the exact performance of the hydrogenation process when using two interconnected fixed bed reactors and forming part of the disclosure of the present invention.

The glycerol used for the hydrogenation may be hydrous. Preferably, however, the water content should be below 15% by weight, more preferably below 10% by weight and most preferably below 5% by weight, based in each case on the total weight of water and glycerol. This has procedural economic reasons, because in the course of hydrogenation water is formed anyway, which is removed in the second process step in the course of distillation. In a further embodiment, the water content of the glycerol used is less than 2% by weight. It may also be desired anhydrous Use glycerol or a glycerol whose water content is only in the trace range.

In the second step of the process according to the invention, the reaction mixture obtained in the first step is subjected to a distillation in a second step, in which preferably the 1,2-propanediol formed in the first step is obtained as distillate. The term "distillation" as used herein is understood to mean its broadest meaning, comprising the evaporation of a liquid mixture, the subsequent condensation of the effluent vapor and the removal of the condensate (distillate).

This distillation can be a single-phase distillation (simple distillation) or a two-phase distillation (rectification), the latter usually being able to be carried out in countercurrent. The single-phase or two-phase distillation can also be carried out batchwise, semicontinuously or continuously.

In a batch process, a once used still bottling feed whose composition continuously changes during distillation is separated into a distillate and a residue. In the case of the present distillation of 1,2-propanediol, the residue increasingly depleted of 1,2-propanediol as the distillation progresses. Preferably, in such a discontinuous distillation, the distillate is successively removed in parts separated by boiling limits (so-called "fractional distillation"), so that the feed mixture is present at the end separated into a residue and several distillate fractions.

In the semicontinuous procedure, the bubbler feed is continuously supplemented with preheated, to be separated still. In the continuous procedure, which succeeds with the counter or DC distillation, the to be separated, preheated liquid mixture is continuously introduced into the apparatus, wherein the mixture is decomposed into a head and a bottom product of substantially constant composition.

Details of the individual distillation methods and the distillation apparatuses suitable for this purpose are in particular chapters 10.4.1, 10.4.2 and 10.4.3 of the specialist book "Basic Operations in Chemical Process Engineering", Wilhelm RA Vauck and Hermann A. Müller, 11th revised and expanded edition, WiI - ley- VCH- Verlag, 2000. The disclosure of this textbook with regard to the manner of carrying out single-phase or two-phase distillations and the distillation temperatures suitable for this purpose is hereby incorporated by reference and forms part of the disclosure of the present application.

The formulation "in which preferably the 1,2-propanediol formed in the first step is obtained as distillate" according to the invention comprises both processes in which the 1,2-propanediol is obtained as the top product of a distillation step (such as in a batchwise, fractional distillation ) as well as processes in which the 1,2-propanediol is withdrawn, for example, as a side draw (such as in a continuous rectification).

If desired, the 1,2-propanediol obtained in the process according to the invention may be subjected to further purification steps known to those skilled in the art in order to further increase the purity of the product. As an example of such a further purification process, for example, the filtration or the extraction may be mentioned. If desired, a portion of the hydrogenation effluent (that is, the reaction mixture obtained after passing through the first step of the process of the present invention) can be used as a diluent for the continuous hydrogenation in the first process step. For example, 25% of the hydrogenation process can be added to the raw material (glycerol) used in the first step of the process according to the invention in order to achieve a gentle reaction without temperature peaks on the hydrogenation catalyst in this way. However, glycerol is preferably fed without backmixing with a defined residence time through the catalyst bed in the reaction tube (s).

Furthermore, it may prove advantageous according to the invention, at least a portion, preferably at least 20 wt .-%, more preferably at least 30 wt .-%, more preferably at least 40 wt .-% and most preferably at least 50 wt .-% of attributed to distillation in the bottoms product glycerol in the first step. In this context, it may prove to be particularly advantageous if at least one part, preferably at least 20 wt .-%, particularly preferably at least 30 wt .-%, more preferably at least 40 wt .-% and most preferably at least 50 wt. -% of the bottom product is recycled without prior purification in the first step. Since the bottoms product obtained in the distillation of the hydrogenation processes is comparatively rich in glycerol, the total yield of 1,2-propanediol from glycite can be reduced by recycling the glycerol from the bottom product or by directly recycling the bottom product itself into the first step of the process according to the invention - rin be further increased.

In addition to the immediate recycling of at least a portion of the bottom product obtained in the distillation in the first process step, it may also be advantageous to first at least a portion of the retained in the bottom product in the distillation glycerol purified by distillation or filtration of the bottom product and only then in the first step to lead back. In this way, an entry of larger amounts of by-products into the hydrogenation reactor can be prevented. To purify the glycerol from the bottom product, it is possible in principle to use those distillation processes which have already been described above in connection with the second step of the process according to the invention.

According to a particular embodiment of the inventive method, both a part of the hydrogenation processes, which were obtained in the first process step, as well as a part of the glycerol from the bottom product, which was retained in the second process step, are recycled to the first process step.

A contribution to achieving the abovementioned objects is also achieved by a process for preparing a compound comprising ether group, at least one ester group, at least one amino group or at least one urethane group or at least two thereof, preferably comprising at least one ester Group or function, including the process steps

al) Preparation of 1,2-propanediol by the process of the invention, and bl) reaction of the 1,2-propanediol with a compound having at least one active hydrogen atom, at least one epoxy group, at least one ester group or at least one isocyanate group ..

The compound having at least one active hydrogen atom may be a compound having at least one hydroxyl group, so that after reaction of this compound with the 1,2-propanediol phase, a compound having at least one ether group is obtained. Depending on the molar ratio in which the compound having at least one hydroxyl group is reacted with 1,2-propanediol contained in the 1,2-propanediol phase, a polyether compound can also be obtained. The compound having at least one active hydrogen atom may also be a compound having at least one carboxylic acid group, so that after reaction of this compound with the 1,2-propanediol phase, a compound having at least one ester group is obtained. Depending on the molar ratio in which the compound having at least one carboxy group is reacted with the 1,2-propanediol contained in the 1,2-propanediol phase, an ester polyether compound can also be obtained.

The compound having at least one active hydrogen atom may also be a compound having at least one amino group, so that after reaction of this compound with the 1,2-propanediol phase, a compound having at least one amino group and at least one hydroxyl group is obtained. Depending on the molar ratio in which the compound having at least one amino group is reacted with 1,2-propanediol contained in the 1,2-propanediol phase, an aminopolyether compound can also be obtained.

If a compound having at least one epoxide group is used in process step b1), ether or polyether can likewise be obtained by reacting this compound with the 1,2-propanediol phase.

If a compound having at least one isocyanate group is used in process step b1), then by reacting this compound with the 1,2-propanediol phase, urethanes or polyurethanes can be obtained.

According to the invention, the use of a compound having at least one carboxylic acid group in process step b1) is particularly preferred. In this case, the compound having at least one carboxylic acid group may be a monocarboxylic acid, a dicarboxylic acid or a tricarboxylic acid, mono- and dicarboxylic acids being particularly preferred and monocarboxylic acids, especially fatty acids, are most preferred. Further, it is preferred that the compound having at least one carboxylic acid has 5 to 30, more preferably 10 to 25, and most preferably 15 to 20 carbon atoms per molecule. In this connection, it is particularly preferred that the compounds having at least one carboxylic acid group is a C ₅ to C 30 monocarboxylic acid, moreover preferably a C ₁₀ to C 25 monocarboxylic acid, and most preferably a C ₁₅ to C 20 monocarboxylic acid in which the abovementioned monocarboxylic acids are saturated monocarboxylic acids, such as, for example, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, fish oil, palmitic acid, margaric acid, stearic acid, arachidic acid, behenic acid, lignoceric acid or cerotic acid, monounsaturated monocarboxylic acids such as undecylenic acid, oleic acid, elaidic acid, vaccenic acid, icosenoic acid, cetoleic acid, erucic acid or neuronic acid, or polyunsaturated monocarboxylic acids, such as, for example, linoleic acid, linolenic acid, arachidonic acid, timnodonic acid, clupanodonic acid or cervonic acid.

According to a preferred embodiment of the process according to the invention for preparing a compound containing at least one ester function, this compound is a fatty acid ester, in particular a fatty acid monoester, a polyester or a polyester resin or a 1,2-propanediol-based alkyd resin , Such alkyd resins are synthetic, strongly hydrophobic polymers obtained by condensation of 1,2-propanediol with polybasic acids with the addition of organic oils or fatty acids (to modify the properties of the resin) and other polyhydric alcohols, in particular glycerol or pentaerythritol. to be obtained. In this case, it is particularly preferred that the compound having at least one carboxylic acid group is a dibasic acid which is preferably selected from the group consisting of phthalic anhydride, isophthalic acid, terephthalic acid, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, naphthalenedicarboxylic acid, 4,4 'Biphenyldicarboxylic acid, diphenylmethane-4,4'-dicarboxylic acid acid, succinic acid, fumaric acid, adipic acid, sebacic acid, azelaic acid and maleic anhydride, with adipic acid, azelaic acid and terephthalic acid being particularly preferred and terephthalic acid being most preferred.

As organic oils, oils or oil derivatives of vegetable and animal origin are suitable in each case individually or as a mixture. As oils and oil derivatives of animal origin tallow as well as from tallow, in particular by fractionation, oil acids to be mentioned. As organic oil or fatty acids are particularly tallow, canola oil, rapeseed oil, sunflower oil, palm oil, which may optionally be present in cured or cured version, rapeseed oil, soybean oil, safflower oil, linseed oil, tall oil, coconut oil, palm kernel oil, castor oil, dehydrated castor oil, fish oil and Tungöl into consideration. In particular, dry oils or semi-dry oils having iodine numbers of at least 100 are preferred, among others, soybean oil and tall oil are advantageous. Suitable fatty acids which are used both to prepare the alkyd resins and to prepare the fatty acid esters are in particular those of soybean oil, thistle oil, linseed oil, tall oil, coconut oil, palm kernel oil, castor oil, dehydrated castor oil, fish oil and tung oil. Of these fatty acids, those of drying oils or semi-drying oils having iodine numbers of at least 100, including those of soybean oil and tall oil, are preferable.

The preparation of alkyd resins can be found, for example, in WO-A-01/62823, the disclosure content of which with respect to the preparation of alkyd resins is hereby introduced as a reference and which forms part of the disclosure of the present invention.

A contribution to the solution of the abovementioned objects is also provided by a compound comprising at least one ester function obtained by the process described above. A further contribution to the solution of the abovementioned objects is afforded by a method for producing a compound comprising at least one ether function, comprising the method steps

a2) Preparation of 1,2-propanediol by the inventive method for

Preparation of 1,2-propanediol, and b2) reaction of the 1,2-propanediol with a compound having at least one epoxy or hydroxyl group or both, to obtain an ethers.

The compound containing at least one ether function is preferably a polyether, more preferably a polytheric polyalcohol. The preparation of polyethers and polyether polyalcohols is known from the prior art, for example from DE 197 26 508 A1.

A contribution to the solution of the abovementioned objects is also provided by a method for producing a hydraulic fluid comprising at least one mineral oil component and 1,2-propanediol, comprising the method steps:

a3) Preparation of 1,2-propanediol or its ethers, often as ethoxylation and / or propoxylation products, or both, preferably 1,2-

Propanediol, by the erfmdungsgemäße process for the preparation of

1,2-propanediol, and b3) bringing the 1,2-propanediol into contact with the at least one mineral oil component.

Hydraulic fluids which are preferred according to the invention are hydraulic oils which fulfill the requirements of ISO 6743/4 and are designated by the designations HL, HM, HV or, in Germany, by the designations HL, HLP, HVLP according to DIN 51524. The hydraulic fluids may in particular be water-in-oil or oil-in-water emulsions which If necessary, other additives such as corrosion inhibitors, agents for improving the aging resistance, to reduce the Fressverschleißes mixed friction region and to improve the viscosity-temperature behavior may contain.

A further contribution to the solution of the abovementioned objects is provided by a process for the production of a cosmetic product comprising at least one skin and / or hair care product and 1,2-propanediol, comprising the process steps:

a4) Preparation of 1,2-propanediol by the process according to the invention for

Preparation of 1,2-propanediol, and b4) contacting the 1,2-propanediol with the at least one skin and / or hair care product.

The cosmetic product is preferably a skin cream, a lotion, a hair care product, a shampoo or a sunscreen. Furthermore, it is preferred according to the invention that the cosmetic product in addition to the 1,2-propanediol and the skin or hair care contains other additives that are commonly used for the production of cosmetic products, such as preservatives, perfumes, emulsifiers, other solvents, such as water and / or ethanol, antioxidants, oils, fats and the like.

A further contribution to the solution of the abovementioned objects is provided by a method for producing a feed comprising at least one nutrient and 1,2-propanediol, comprising the method steps:

a5) Preparation of 1,2-propanediol by the process according to the invention for preparing 1,2-propanediol, and b5) contacting the 1,2-propanediol with the at least one nutrient tel.

The foodstuff may be a starch-containing foodstuff such as high-starch grains, seeds, tubers, cereals, potato, cassava or millet, for example, an oily food made from, for example, rapeseed, soy, sunflower, linseed , Peanut and the like, or a green feed mainly based on carbohydrates.

A further contribution to the solution of the abovementioned objects is afforded by a process for the preparation of a coloring agent comprising at least one pigment or dye and 1,2-propanediol, comprising the process steps:

a6) Preparation of 1,2-propanediol by the process according to the invention for the preparation of 1,2-propanediol, and b6) contacting the 1,2-propanediol with the at least one pigment or dye.

The colorant is preferably a printing ink, this colorant, in addition to the pigment or the dye and the 1,2-propanediol, further additives known to the person skilled in the art, such as further solvents, binders, fillers and special additives, such as thixotropic agents , may contain.

A further contribution to the solution of the abovementioned objects is made by a process for producing a detergent comprising at least one surfactant and 1,2-propanediol, comprising the process steps:

a7) Preparation of 1,2-propanediol by the process according to the invention for the preparation of 1,2-propanediol, and b7) contacting the 1,2-propanediol with the at least one surfactant. In particular, liquid heavy-duty detergents are preferred as detergents which, in addition to the 1,2-propanediol and the at least one surfactant, are preferably further additives, such as water softeners, for example zeolite A and also phyllosilicates, wash alkalis, enzymes, for example amylases, lipases, proteases or cellulases, Dirt carriers, such as carboxymethyl cellulose coated cotton fibers, core soaps, defoamers, such as silicones, fragrances, stabilizers and preservatives may contain.

In particular, a process for the preparation of an emulsion in which an aqueous phase and an organic phase in the presence of a compound according to the invention have at least one ester group, preferably in the presence of a monofatty acid ester according to the invention, with formation of an emulsion, contributes to the solution of the abovementioned objects be brought into contact with each other.

In principle, all water-immiscible organic solvents are suitable as the organic phase. However, organic phases are particularly preferably based on synthetic, vegetable or animal oils. As oils here come, for example liquid at room temperature fatty acid triglycerides, especially vegetable oils such as rapeseed oil, sunflower oil, thistle oil, olive oil, linseed oil, pumpkin seed oil, hemp oil or mustard oil, or animal oils such as tallow, fish oil or claw oil. are used less frequently as food. However, they are used in the chemical industry (eg lubricating oils, soap) or in mechanical engineering (lubricants). Suitable synthetic oils are, for example, silicone oils. Hydrocarbon-based organic phases may also be included in the emulsions. Here in particular paraffins come into consideration. Furthermore, the emulsion according to the invention may be a water-in-oil or an oil-in-water emulsion.

The amount of the compound according to the invention having at least one ester group, preferably the amount of a monofatty acid ester according to the invention, in the emulsion according to the invention is preferably in a range from 50 to 0.1% by weight, more preferably in a range from 20 to

0.5% by weight and most preferably in a range of 5 to 1% by weight, based in each case on the total weight of the emulsion. The volume ratio of aqueous phase and organic phase can vary widely and is particularly dependent on whether a water-in-oil or a

Oil-in-water emulsion should be obtained.

The preparation of the emulsion according to the invention is preferably carried out by the methods known in the art for the preparation of emulsions. Preferably, the individual components of the emulsion according to the invention are combined and converted into an emulsion by means of a suitable homogenizer, for example by means of a rapid stirrer, a high-pressure homogenizer, a shaker, a vibration mixer, an ultrasonic generator, an emulsifying centrifuge, a colloid mill or an atomizer.

A contribution to the solution of the abovementioned objects is further provided by an emulsion obtainable by the process described above. In comparison to the emulsions known from the prior art, this emulsion is characterized by a noticeably better storage stability.

In another embodiment, the invention relates to a cosmetic composition comprising an emulsion according to the invention. Cosmetic composition according to the invention, an emulsion being prepared by a process according to the invention and having at least one cosmetic composition component is brought into contact. Suitable cosmetic components are all those skilled in the art for various cosmetic products such as ointments, pases, creams, lotions, powders, waxes or gels and shampoos, soaps, scrubs, sunscreen or make-up known ingredients. Of these, one or more of these emulsions will be present in amounts ranging from 0.01% to 15% by weight, preferably in the range of from 0.1% to 15% by weight, and most preferably in the range of 0.15 to 5 wt .-%, each based on the cosmetic composition used.

In a further embodiment, the invention relates to a plastic composition comprising at least one plastic and a compound comprising at least one ether group according to the invention, at least one ester group according to the invention, at least one amino group according to the invention or at least one urethane group according to the invention, preferably including at least one ester group according to the invention. Often, one or more of these compounds will be present in amounts ranging from 0.01% to 15% by weight, preferably in the range of from 0.1% to 15% by weight, and more preferably in the range of from 0.15 to 5 Wt .-%, each based on the plastic, used. A contribution to the present invention is also made by a process for producing a plastic composition, wherein a compound comprising at least one ether group according to the invention, at least one ester group according to the invention, at least one amino group according to the invention or at least one urethane group according to the invention, preferably comprising at least one Inventive ester group, which is prepared in each case by a process according to the invention and brought into contact with at least one plastic. In principle, all plastics which are familiar to the person skilled in the art may be considered as plastics, thermoplastics being preferred whose workability, in particular their demoldability and wall adhesion, can be improved (Gächter / Müller, Kunststoff-Additive, Carl Hanser Verlag 1989). Of these, preferred are polyesters and polyolefins. Before- ferred polyesters are PET, PBT, PLA or PHB. Preferred polyolefins are PE, PP, PVC, SAN, with PVC being particularly preferred.

In another embodiment, the invention relates to a drilling composition comprising at least one liquid rinsing component and a compound comprising at least one ether group obtainable according to the invention, at least one ester group obtainable according to the invention, at least one amino group obtainable according to the invention or at least one urethane available according to the invention. Group, preferably comprising at least one ester group obtainable according to the invention. Often, one or more of these compounds will be present in amounts ranging from 0.01% to 15% by weight, preferably in the range of from 0.1% to 15% by weight, and more preferably in the range of from 0.15 to 5 % By weight, based in each case on the flushing component.

A further embodiment of the present invention relates to a method for producing a drilling composition, wherein a compound comprising at least one ether group, at least one ester group, at least one amino group or at least one urethane group, preferably containing at least one ester group, or else at least two thereof are prepared by a process according to the invention and are brought into contact with at least one liquid rinsing component.

In principle, all known to those skilled in the art for the drilling of rock wells, in particular liquid rinsing systems, closed oil drilling fluids and Bohrspülflüssigkeiten based on water-based OAV emulsion systems come into consideration as drilling compositions.

Liquid flushing systems for drilling rock drilled holes while applying the detached drill cuttings are known to be limited to thickened, flowable systems which can be assigned to one of the following three classes: Purely aqueous drilling fluids, oil drilling fluids commonly used as invert emulsion slurries, and water based O / W emulsions containing a heterogeneous finely dispersed oil phase in the closed aqueous phase.

Closed-oil drilling fluids are generally constructed as a three-phase or multi-phase system: oil, water and finely divided solids. The aqueous phase is distributed heterogeneously finely dispersed in the closed oil phase. A plurality of additives are provided, in particular emulsifiers, fluid loss additives, alkali reserves, viscosity regulators and the like. For details reference is made, for example, to the publication P. A. Boyd et al. Journal of Petroleum Technology, 1985, 137-42, and RB Bennett, "New Drilling Fluid Technology - Mineral OiI Mud" Journal of Petroleum Technology, 1984, 975-981, and the literature cited therein ,

Drilling fluids based on water-based O / W emulsion systems occupy an intermediate position in their performance properties between the purely aqueous systems and the oil-based invert fluids. Detailed factual information can be found here in the relevant specialist literature, reference is made, for example, to the specialist book George R. Gray and HCH Darley, "Composition in Properties of Oil Well Drilling Fluids", 4th edition, 1980/81, Guild Publishing Company , Houston and the extensive technical and patent literature cited therein, and the handbook "Applied Drilling Engineering", Adam T. Bourgoyne, Jr. et al., First Printing Society of Petroleum Engineers, Richardson, Texas (USA).

The use of the hydrogenation processes obtained in the first step of the process according to the invention and / or the 1,2-propanediol obtained after passing through both steps of the process according to the invention also contributes to the solution of the abovementioned processes as a refrigerant, for producing a compound comprising at least one Ester function, preferably for Preparation of a polyester or of an alkyd resin, for producing a compound comprising at least one ether function, preferably for producing a polyether, as heat transfer medium, as hydraulic fluid or as component for a hydraulic fluid, for lowering the freezing point of aqueous phases, as solvent or plasticizer Coloring agents, in particular in printing inks, as a solvent or as an excipient in preferably liquid detergents, as an additive in feeds, as humectants in food and tobacco products, as a formulation component in cosmetic products, as an additive or base or both in pumping agents or lubricants or both, especially in the Exploration of oil deposits, or as a formulation component of corrosion inhibitors.

In particular, the use of the compound obtained by the erfmdungsgemäße method for producing a compound containing at least one ester function containing at least one ester function, in particular the use of a fatty acid monoester obtained by this method, as an emulsifier or as a formulation component for PVC extrusions contributes to solve the problems mentioned above.

In particular, the present invention relates to a process for the preparation of a compound comprising at least one ether group, at least one ester group, at least one amino group or at least one urethane group or at least two thereof, including the process steps,

al) Preparation of 1,2-propanediol by a process according to any one of claims 1 to 12, and bl) reaction of the 1,2-propanediol with a compound having at least one active hydrogen atom, at least one epoxy group, at least one ester group or at least one isocyanate group, the method comprising the further step of contacting an aqueous phase and an organic phase in the presence of the compound comprising at least one ester group to form an emulsion. In addition to this process step, the process may further comprise the process step of contacting the emulsion with at least one cosmetic component to form a cosmetic composition.

Furthermore, the present invention relates to a process for preparing a compound comprising at least one ether group, at least one ester group, at least one amino group or at least one urethane group or at least two thereof, comprising the process steps al) and bl), wherein the method comprises the further step of contacting the compound comprising at least one ether group, at least one ester group, at least one amino group or at least one urethane group, preferably containing at least one ester group, with at least one plastic to form a Kunsstoffzusammensetzung.

Furthermore, the present invention relates to a process for preparing a compound comprising at least one ether group, at least one ester group, at least one amino group or at least one urethane group or at least two thereof, comprising the process steps al) and bl), wherein the method comprises the further step of contacting the compound comprising at least one ether group, at least one ester group, at least one amino group or at least one urethane group, preferably containing at least one ester group with at least one liquid rinse component to form a drilling composition.

The invention also relates to an emulsion obtainable by the process described above, a cosmetic composition obtainable by the process described above, a Kunsstoffzusammensetzung available by the method described above and a drilling composition obtainable by the method described above.

In particular, the present invention also relates to a process for the preparation of a composition comprising the process steps:

Al) Preparation of 1,2-propanediol by the process of the invention described in the introduction, and

B1) contacting the 1,2-propanediol with the at least one component selected from the group consisting of a mineral oil component, a skin and / or hair care agent, a nutrient, a pigment, a dye or a surfactant.

According to a particular embodiment of this process, the composition is a hydraulic fluid containing at least one mineral oil component and 1,2-propanediol, wherein in process step B2) the 1,2-propanediol is brought into contact with at least one mineral oil component.

According to another particular embodiment of this method, the composition is a cosmetic product comprising at least one skin and / or hair care product and 1,2-propanediol, wherein in process step B2) the 1,2-propanediol with at least one skin and / or hair care product is brought into contact.

According to another particular embodiment of this method, the composition is a feed comprising at least one nutrient and 1,2-propanediol, wherein in process step B2) the 1,2-propanediol is brought into contact with at least one nutrient. According to another particular embodiment of this process, the composition is a pigment or dye and 1,2-propanediol, and in process step B2) the 1,2-propanediol is brought into contact with at least one pigment or dye.

According to another particular embodiment of this method, the composition is a detergent comprising at least one surfactant and 1,2-propanediol, wherein in process step B2) the 1,2-propanediol is brought into contact with at least one surfactant.

The invention also relates to the composition obtainable by the methods described above.

The invention will now be explained in more detail by way of non-limiting examples:

EXAMPLES

Example 1 :

A 2 m long reaction tube with an internal diameter of 25 mm (continuous hydrogenation) was filled with a copper-chromium type catalyst (type G99 BO 3 x 3 from Südchemie). Pure glycerol was hydrogenated continuously under the following conditions: temperature = 220 ^° C.; 250 bar; 13 Nm ³ / h of hydrogen; Throughput = 882 g / h.

To monitor the degree of conversion of the glycerol, the hydrogenation effluent was analyzed by GC, but not completely, but only in terms of its content of glycerol, 1,2-propanediol and ethylene glycol. Result: 34.2% glycerol, 65.3% 1,2-propanediol, 0.5% ethylene glycol. By-products could only be observed as small impurities in the GC. The hydrogenation effluent had a faint odor and was almost clear. The hydrogenation effluent was distilled in the laboratory: fractionation with attached 20 cm Vigreux column, distillation at atmospheric pressure, amount used: 1000 g.

Upon fractionation, the four fractions I to IV were obtained. The associated data are shown in Table 1. In this table, in column 1, "Fr" means the respective fraction and "R" the distillation residue. Columns 2 and 3 show the sump and broth temperatures of the respective fractions. Column 4 gives the amount (in grams) of fractions obtained. Column 5 indicates the fractions closer.

Table 1

For the purposes of the inventive method is fraction IV (505.4g colorless, clear liquid). This fraction is the target product.

Comparative Example 1

Example 1 was repeated but glycerol was hydrogenated almost completely (and not partially as in Example 1). This was done by raising the temperature to 230 ⁰ C and reducing the throughput to 441 g / h. To monitor the degree of conversion of glycerol, the hydrogenation sequence was analyzed, but not completely, but only with respect to its content of glycerol, 1, 2-propanediol and ethylene glycol. Result: 0.5% glycerol, 98.7% 1,2-propanediol, 0.8% ethylene glycol. The hydrogenation effluent had an extremely strong odor and was cloudy. Several small peaks could be detected in the GC, but these could not be qualified.

The hydrogenation effluent was distilled in the laboratory: fractionation with attached 20 cm Vigreux column, distillation at atmospheric pressure, amount used: 1000 g In fractionation, the four fractions I to IV were obtained. The associated data are shown in Table 2.

Table 2

Final product of the comparative experiment is fraction IV (705.4 g colorless liquid, odor of ether).

Example 2:

Example 1 was repeated except that the glycerol used in a ratio of 4: 1 was mixed with the hydrogenation procedure obtained in Example 1 (4 parts by weight of pure glycerol and 1 part by weight of the hydrogenation procedure from Example 1).

To monitor the degree of conversion of the glycerol, the hydrogenation sequence was analyzed, but not completely, but only with respect to its content of glycerol, 1,2-propanediol and ethylene glycol. Result: 13.8% glycerol, 85.6% 1,2-propanediol, 0.6% ethylene glycol. The hydrogenation effluent had a faint odor and was almost clear.

The hydrogenation effluent was distilled in the laboratory: fractionation with attached 20 cm Vigreux column, distillation at atmospheric pressure, amount used: 1000 g.

Upon fractionation, the four fractions I to IV were obtained. The associated data are shown in Table 3.

Table 3

For the purposes of the process according to the invention, fraction IV (630.7 g colorless, clear liquid, odorless) is the decisive fraction. This is the target product product. In this fraction could be identified by gas chromatography no further by-products.

Comparative Example 2:

Example 1 was repeated but glycerol was fully hydrogenated (and not partially as in Example 1). This was done on the one hand by increasing the temperature to 250 ⁰ C, using a copper silicate (Cu-SiO ₂ / Kata Leuna) and choice of a throughput of 441 g / h.

The hydrogenation effluent (yellow, floating droplets, very unpleasant odor) was distilled: fractionation with attached column as in Table 1, distillation at atmospheric pressure, amount used: 1000 g.

In the fractionation, the five fractions I to V were obtained. The associated data are shown in Table 4. Table 4

Fractions III to V were combined to give 730.6 g of a clear liquid with a slight odor. GC composition: 93.5% 1,2-propanediol, 4.0% ethylene glycol, 2.5% unknown by-products.

In fact, this total fraction had the same Broth temperature as fraction IV described in Tables 1 to 3, d. H. the distillation behavior was identical.

As a comparison product here is the total fraction (fractions III to V) to address. It is clear that the quality of the total fraction is classified as very poor (purity only 93.5%, with 4% very much ethylene glycol and further 2.5% of other by-products). The total fraction also had an inherent odor and showed a slight haze upon the addition of water.

Claims

claims

1. A process for the preparation of 1,2-propanediol having a purity of at least 98%, characterized in that in a first

Step glycerol continuously hydrogenated in the presence of a heterogeneous copper-containing catalyst, wherein glycerol is reacted to at most 95%, and subjected to the reaction mixture obtained in the first step in a second step of a distillation.

2. The method of claim 1, wherein one uses a heterogeneous copper-chromium-containing catalyst.

3. The method of claim 1, wherein one uses a heterogeneous Kupferchro- with catalyst.

4. The method of claim 1 to 3, wherein the hydrogenation is carried out in isothermally operated tubular reactors or tube bundle reactors.

5. The method according to claim 4, wherein the hydrogenation is carried out by passing liquid glycerol in trickle bed in cocurrent or countercurrent with hydrogen over a fixed catalyst bed.

6. The method of claim 5, wherein glycerol leads without backmixing with a defined residence time through the catalyst bed in the or the reaction tubes.

7. The method according to any one of claims 1 to 6, wherein the hydrogenation is carried out at a temperature in the range of 180 to 220 ⁰ C.

8. The method according to any one of claims 1 to 7, wherein the water content of the glycerol used is below 2%.

9. The method according to any one of claims 1 to 8 wherein glycerol is reacted in the first step to at most 90%.

10. The method according to any one of claims 1 to 9, wherein at least a portion of the retained in the distillation in the bottom product glycerol is returned to the first step.

11. The method of claim 10, wherein at least a portion of the bottom product is recycled without prior purification in the first step.

12. The method of claim 10, wherein at least a portion of the glycerol obtained in the bottom product in the distillation is first purified by distillation or filtration of the bottom product and only then returned to the first step.

13. A process for the preparation of a compound comprising at least one ether group, at least one ester group, at least one amino group or at least one urethane group or at least two thereof, including the process steps comprising the process steps

al) Preparation of 1,2-propanediol by a process according to any one of claims 1 to 12, and bl) reacting the 1, 2-propanediol with a compound having at least one active hydrogen atom, at least one epoxy group, at least one ester group or at least one isocyanate group.

14. The method of claim 13, wherein the compound includes at least one ester group.

15. The method of claim 14, wherein the compound containing at least one ester function is a fatty acid monoester, a polyester resin or a polyalkyd resin.

16. The method of claim 14 or 15, comprising the further process step of contacting an aqueous phase and an organic phase in the presence of the compound comprising at least one ester group to form an emulsion.

17. The method of claim 16, comprising the further step of contacting the emulsion with at least one cosmetic

Component to form a cosmetic composition.

18. The method according to claim 13, comprising the further method step of bringing the compound into contact containing at least one ether group, at least one ester group, at least one amino group

A group or at least one urethane group, preferably containing at least one ester group, with at least one plastic to form a Kunsstoffzusammensetzung.

19. The method according to claim 13, comprising the further method step of bringing the compound into contact containing at least one ether group, at least one ester group, at least one amino group or at least one urethane group, preferably containing at least one ester group A group comprising at least one liquid rinse component to form a drilling composition.

20. A process for preparing a compound comprising at least one ether function according to claim 13, wherein the 1,2-propanediol prepared in process step al) in process step bl) with a compound auffweisend at least one hydroxyl group as a compound having at least one active hydrogen atom or with a compound having at least one epoxy group, or both, is reacted.

21. A compound comprising at least one ether group, at least one ester group, at least one amino group or at least one urethane group or at least two thereof, obtainable by a process according to any one of claims 13 to 15 and 17, an emulsion obtainable by the process of claim 16, a cosmetic composition obtainable by the process of claim 17, a plastic composition obtainable by the process of claim 18 or a drilling composition obtainable by the process of claim 19.

22. A method of making a composition comprising the steps of:

Al) Preparation of 1,2-propanediol by a process according to any one of claims 1 to 12, as well as

B2) bringing the 1,2-propanediol into contact with the at least one component selected from the group consisting of a mineral oil component, a skin and / or hair care product, a

Nutrient, a pigment, a dye or a surfactant.

23. The method of claim 22, wherein the composition is a hydraulic fluid containing at least one mineral oil component and 1,2-propanediol and wherein in step B2) the 1,2- Propandiol is contacted with at least one mineral oil component.

24. The method according to claim 22, wherein the composition is a cosmetic product comprising at least one skin and / or hair care agent and 1,2-propanediol and wherein in process step B2) the 1,2-propanediol with at least one skin and / or hair care product is brought into contact.

25. The method of claim 22 wherein the composition is a feed comprising at least one nutrient and 1,2-propanediol and wherein in step B2) the 1,2-propanediol is contacted with at least one nutrient.

26. The method of claim 22, wherein the composition is a colorant containing at least one pigment or dye and 1,2-propanediol, and wherein in step B2) the 1,2-propanediol is contacted with at least one pigment or dye.

27. The method of claim 22, wherein the composition is a detergent comprising at least one surfactant and 1,2-propanediol and wherein in step B2) the 1,2-propanediol is brought into contact with at least one surfactant.

28. A composition obtainable by a process according to any one of claims 22 to 27.

29. Use of the hydrogenation processes obtained in the first step of the process according to any one of claims 1 to 12 and / or of the two steps of the process according to any one of claims 1 to 12 1,2-propanediol obtained as a refrigerant, for producing a compound containing at least one ester function, for producing a compound containing at least one ether function, as a heat transfer medium, as a hydraulic fluid or as a component for a ne hydraulic fluid, to reduce the freezing point aqueous

Phases, as solvents or plasticizers in colorants, especially in printing inks, as a solvent or as an excipient in preferably liquid detergents, as an additive in feeds, as humectants in food and tobacco products, as a formulation component in cosmetic products, as an additive or base or both

Pumping agents or lubricants or both or as a formulation component of corrosion inhibitors.

30. Use of the compound comprising at least one ester group according to claim 21 as an emulsifier or as a formulation component for

PVC extrusions.