EP0442924A1

EP0442924A1 - New mixtures of fatty alcohols and their ethoxylates with improved low-temperature behaviour

Info

Publication number: EP0442924A1
Application number: EP89912442A
Authority: EP
Inventors: Karl-Heinz Schmid; Hans Peter Kubersky; Günter DEMMERING; Alfred Meffert
Original assignee: Henkel AG and Co KGaA
Current assignee: Henkel AG and Co KGaA
Priority date: 1988-11-09
Filing date: 1989-10-31
Publication date: 1991-08-28
Also published as: ES2053910T3; WO1990005127A1; DK86691A; JPH04501561A; BR8907762A; EP0370273B1; DE3837947A1; EP0370273A1; DK86691D0; EP0370273B2; ATE87292T1; DE58903884D1; KR900701710A

Abstract

Mixtures of fatty alcohols, Rmix-OH, of natural origin, in particular of purely vegetable origin, and of their ethoxylates with improved low-temperature behaviour and of general formula Rmix-O-(CH2CH2O)x-H, where x is a number from 2 to 10 and Rmix- denotes selected mixtures of saturated and olefinically unsaturated fatty-alcohol hydrocarbon residues in the range C 6 to C 20 or C 12 to C 20, which correspond, for the range of chain lengths Rmix = C 6 to C 20, to specification (I) and, for the range of chain lengths Rmix = C 12 to C 20, to specification (II).

Description

"New fatty alcohol mixtures and their ethoxylates with improved cold behavior"

In the past decade, alkyl or alkylaryl polyglycol ethers as nonionic surfactants have become increasingly important as formulation constituents of detergents and cleaning agents and as constituents of emulsifiers in cosmetic or technical preparations. The basis for the synthesis of such non-ionic surfactants are alkylphenols, oxo alcohols according to the high-pressure (Roelen process) or low-pressure (shop process) hydroformulation processes, alcohols according to the Ziegler process and fatty alcohols, such as those used for. B. can be obtained by hydrogenating natural oils and fats or from the native fatty acids or their methyl esters produced therefrom.

Alkyl polyglycol ethers based on oxo alcohols as well as Ziegler and fatty alcohols are becoming increasingly important due to their more favorable ecotoxic properties compared to alkyl phenol polyglycol ethers. Since most technical emulsifiers are used in liquid formulations, one of the most important requirements for nonionic surfactants has always been the lowest possible pour point. This demand for non-ionic surfactants with sufficiently good cold behavior has increased in recent years in particular by the fact that liquid formulations have found their way into product areas where previously only powder formulations were known. The area of detergents and cleaning agents, especially textile detergents, should be mentioned here in particular. With regard to the desired good low-temperature behavior in the field of alkyl polyglycol ethers, the ethoxylates of oxoalcohols branched in their basic structure are superior to those based on linear alcohols - in particular Ziegler alcohols and fatty alcohols - with the same carbon chain length of the alkyl part and the same number of ethylene oxide units in the molecule. As is known, the pour point of an alcohol, as well as the ethoxylate produced from it, the lower the branched the structure of the alcohol.

Particularly important in terms of application technology is alkyl ethoxylates with an average of about 5 to 10 moles of ethylene oxide, based on 1 mole of alcohol, where the alcohol in particular has a carbon chain length of about 12 to 15. Compounds of this type are distinguished by particularly good washing, wetting, emulsifying and cleaning properties. Compounds of this type based on currently available fatty alcohols of native origin of comparable carbon chain lengths and the same proportion of ethylene oxide in the molecule are inferior to the corresponding compounds based on oxo alcohols in terms of low-temperature behavior. The invention seeks a technically better solution compared to dealing with this problem today.

Coconut oil, Paimkernό in particular come as natural raw material sources for a fatty alcohol which has the carbon chain length C 12 to C 14 described above in terms of application technology. and babassu oil in question. A disadvantage of these oils is, however, that the fatty alcohols obtained therefrom - particularly in the case of palm kernel oil and babassu oil - still contain considerable amounts of undesired C 16 / C 18 components, which lead to unsatisfactory low-temperature behavior in the ethoxylates prepared therefrom. If, according to previous technical practice, one wants to produce, for example, an alkyl ethoxylate with an average of 7 moles of ethylene oxide per mole of alcohol based on a coconut alcohol, which has a similar cold behavior to the corresponding ethoxylate based on an oxo alcohol of carbon chain length C 12 to C 15, so Previously, one had to remove the proportion of C 16/18 from the alcohol extracted from coconut oil by fractional distillation. This is expensive not only because of the associated costs for the distillation, the C 16 / C 18 alcohol separated from the coconut fatty alcohol is identical to the fatty alcohol fractions that can be obtained from the much cheaper tallow and is therefore significantly devalued compared to coconut alcohol. The corresponding loss of material due to removal of the C 16 / - C 18 content is approx. 20% by weight with a fatty alcohol mixture ex coconut oil and approx. 25% by weight with a fatty alcohol mixture ex palm kernel oil.

It was an object of the invention to show a way in which fatty alcohol mixtures and their ethoxylates can be obtained from preferably purely vegetable oils or fats and their ethoxylates without the material loss just described, which, with regard to their cold behavior, can be obtained with the corresponding materials based on oxo alcohols are comparable and nevertheless have the carbon chain length required for technical reasons.

When fatty alcohols or fatty alcohol fractions are obtained from fats and / or oils of vegetable origin, the fatty ureat mixtures obtained from the vegetable raw materials are reduced as the fatty acid methyl ester under process conditions to the corresponding alcohols under hydrogenation conditions, in which not only the reduction the carboxyl function, but also the extensive saturation of chain olefinic double bonds takes place. Typical - H -

Examples of the previous production process of such fatty alcohol fractions are the treatment of fatty acid methyl esters ex coconut, palm kernel and babassu oil at 200 to 250 ° C. and hydrogen pressures of 250 to 300 bar over a catalyst consisting of copper and chromium oxide, cf. ¬ wise H. Baumann, Angew. Chem. 100 (1988) 50 and U. R. Kreutzer, J. Amer. Oil Chem. Soc. 61: 343 (1984).

The teaching of the invention is based on the finding that fatty alcohols and ethoxylates produced from these fatty alcohols can be produced with significantly better low-temperature behavior from the same vegetable raw materials, if the chain-linked, partially olefinic structure of these starting materials is changed as little as possible and instead is changed limited to a selective reduction of the carboxy function. The fatty alcohol fractions obtained in this way, which in their composition of the hydrocarbon residues are as similar as possible to the type of vegetable oils used or the fatty acid mixtures present therein, are distinguished by a significantly improved cold behavior. It is more important, however, that the previously mentioned ethoxylates of the average degree of ethoxylation required for, for example, washing and cleaning reasons, have, in terms of cold behavior, product properties which at least correspond to those of the previously superior oxo alcohol derivatives.

It is known per se to carry out the hydrogenating reduction of unsaturated fatty acids by selecting suitable process conditions and in particular suitable catalysts with largely selective conversion of the carboxyl function and while maintaining the chain double bonds of the starting compounds to unsaturated alcohols. For example oleyl alcohol can be obtained starting from oleic acid or oleic acid methyl ester when using special zinc-containing catalysts, see, for example, the literature H already cited. Baumann loc. Cit. and U. R. Kreutzer a. A. O. In addition, reference is made to the German patent specification 25 13 377 and the older German patent specifications 865 741 and 965 236 cited therein. The essence of the teaching according to the invention, however, lies in the previously unknown finding that - starting from the vegetable oils or - fats preferably of purely natural origin - reaction products of the type described can be obtained which, in terms of their performance level, at least correspond to products based on oxo alcohols. The chemistry based on natural renewable raw materials thus opens up an important extension in the partial aspect discussed here In terms of the requirement profiles made by practice today.

The invention accordingly relates to a first

Embodiment new fatty alcohol mixtures R. OH of natural, in particular purely vegetable origin and their ethoxylates with improved low-temperature behavior and the general formula in which x is a number from 2 to 10, zuq ⁼ t from 3 to 9, and R m .ix - stands for selected mixtures of saturated and olefinically unsaturated fatty alcohol carbons hydrogen radicals in the ranges C 6 to 20 or C 12 to 20, which stands for the chain length range R. - = C 6 to 20 of the following specification I and for the chain length range C 12 to 20 of the following specification II speak : specification

structurally analogous to% by weight

0.1 - 0.6 2.5 - 10 2.5 - 14 37 - 52 10 - 20 6 - 10 1 - 5 5 - 23 1 - 4 0.1 - 1 0.1 - 1

structurally analogous to% by weight

39-69

10-27

6 - 14

1 - 7

6 - 31

1 - 6

0.1-2 0.1-2

In a preferred embodiment of the invention, the fatty alcohol mixtures of specification I can be of particular importance if the ratio of the simple olefinically unsaturated hydrocarbon radical having 18 carbon atoms to the sum of the single and double olefinically unsaturated hydrocarbon residues, each with 18 carbon atoms, is greater than 78%.

Preferred fatty alcohol mixtures of the previously specified specifications are preferably of purely vegetable origin or, respectively, by selective hydrogenation of corresponding mixtures of fatty acids of natural origin. accessible by the selective hydrogenation of corresponding ester mixtures of such fatty acids. Particularly suitable esters for this selective hydrogenation are corresponding esters with monofunctional alcohols, in particular lower monohydric alcohols with 1 to 5 carbon atoms. As is well known, the methyl ester and, to a certain extent, the butyl ester are of particular importance. The selective hydrogenation is carried out while maintaining the natural distribution of the saturated and the mono- and poly-olefinically unsaturated hydrocarbon residues in the feed material as far as possible. Particularly suitable feedstocks of purely vegetable origin are coconut oil, palm kernel oil, babassu oil and rocca fat or the fatty acid mixtures obtained therefrom and in particular the corresponding fatty acid methyl ester mixtures.

Fatty alcohol mixtures of the aforementioned Specification I still contain the lower fractions from C 6 to C 10, which can be odorlessly undesirable in certain areas of application. The invention accordingly comprises the alcohol mixtures of the aforementioned Specification II, which can be easily obtained from the substance mixtures of the aforementioned Specification I by removing the C 6 to C 10 fraction. However, both fatty alcohol mixtures and in particular the ethoxylates described according to the invention obtained therefrom are notable for their considerable content, in particular of C 16 / C 18 components. The content according to the invention of this fraction of mono- and poly-olefinically unsaturated components nevertheless, the desired goal of cold stability comparable to the oxo alcohols or their derivatives is certain, without substantial material losses of the renewable feed material having to be accepted. The ethoxylates of particular interest here are also completely satisfactory in the other technical properties.

In a further embodiment, the invention relates to the use of fatty alcohol mixtures R. -OH where the

Rest level specifications I or II speaks for the production of ethoxylates with improved flowability at low temperatures, especially in the room temperature range. These ethoxylates correspond to the all-e has the given meaning and x is a number from 2 to 10, preferably from 3 to 9.

The ethoxylates are prepared from the fatty alcohol mixtures defined according to the invention in a manner known per se by reacting the alcohol mixtures with ethylene oxide, either with alkaline or acidic catalysis. There is extensive literature on this known method of producing, in particular, corresponding nonionic surfactants. Alkaline catalysis is widespread in the industrial process, although sodium methylate, but also sodium hydroxide, sodium, sodium ethylate, potassium hydroxide, etc. are generally used as catalysts. The reaction is exothermic through the ring opening. The reaction temperature is for example in the range of about 135 to 150 C. The reaction product is then mixed with inorganic or organic acids, for. B. neutralized with acetic acid anhydride, phosphoric acid or carbon dioxide. The resulting ethoxylation product is not uniform, rather polymer homologs are obtained. The distribution curve differs depending on the type of catalysis. In addition to the In addition to the usual batch ethoxylation, there are also continuous processes. The reaction conditions can be chosen much more drastically. For example, you can work at 50 to 70 atm and 250 to 350 C. For the relevant literature, reference is made, for example, to the publication by Dr. W. Wirth "Tenside, Detergents" 12 (1975) 245 to 254 and the literature cited therein.

Finally, in a further embodiment, the invention relates to the use of ethoxylates of selected fatty alcohol mixtures of natural, preferably purely vegetable, origin with the an -H, in the R. - The specifications I or II given above and x means on average a number from 2 to 10, preferably from 3 to 9, as a surfactant component with improved low-temperature behavior. Ethoxylates of the type described here are distinguished, in particular in the area of room temperature, by their presence as a homogeneous liquid phase, also with good flow properties. Even if surfactant mixtures of the type in question are solidified by supercooling, such materials melt again in a short time when the room temperature is adjusted to the easily pourable homogeneous liquid phase. For the use of these materials as a nonionic surfactant component, there are considerable advantages in everyday use in many fields of application. Not only is it easier to handle. The hitherto customary nonionic surfactants of the type concerned, based on vegetable fats, were at risk, in particular at higher EO contents within the range described, in that a partial solidification of the reaction product can be observed in the case of prolonged storage below room temperature. Such reaction products can still be flowable, but their batch processing from a storage container is understandably difficult. It is required before removal a portion of the material carefully homogenized the contents of the container in order to reliably rule out any shifts in the composition of the complex reaction product. The ethoxylates preferred according to the invention are present in the region of the room temperature as a homogeneous liquid phase in which segregation processes are eliminated from the outset. This ensures a quantity that is not restricted in terms of quantity and, in some cases, material removal with constant product properties.

In a particular embodiment, the teaching of the invention combines the new measures for improving the cold resistance of fatty alcohol ethoxylates of the type described with the teaching of the earlier application P 3802027.0 (D 8083) by the applicant. This earlier application describes a process for the preparation of alkyl polyglycol ethers with improved cold behavior by reacting saturated and / or unsaturated, in particular straight-chain alcohols with ethylene oxide at elevated temperatures in the presence of basic alkali metal compounds as catalysts and subsequent neutralization of the alkaline Catalyst with organic and / or inorganic acids. The characteristic of the teaching from this earlier protective right is that one works with such increased catafyzator concentrations that salt precipitation occurs as an undissolved solid phase in the neutralization step and that the neutralization step is carried out in such a way that the salt phase is precipitated in the presence of im Reaction product disperses finely divided solids.

This teaching of the earlier application is based on the task of making fatty alcohol ethylene oxide adducts with improved low-temperature stability accessible without a deterioration in the other application properties in a technically simple process. The technical solution to this task works based on the knowledge that a substantial increase in the amount of basic alkali metal catalysts in the ethoxylation step can result in substantial improvements in the material parameters characterizing the cold stability without undesirably increasing the application properties such as washing or wetting properties, emulsifying properties and the like affect. However, the amount of the basic catalyst must be increased beyond the limit which characterizes the solubility of the salt obtained by neutralization in the ethoxylation product. To solve this difficulty, it is accordingly proposed in the earlier application to carry out the catalyst neutralization in the presence of finely divided solids which are distributed as homogeneously as possible in the reaction mixture. Surprisingly, it has been shown that incrustations on the parts of the apparatus and / or line can be completely prevented by this measure and that filtration of the reaction product in conventional processes is still possible without difficulty.

The result of working with increased amounts of catalyst in the polyethoxylation step is the production of alkyl polyglycosylation reaction products with a narrow homolog distribution. Such narrow homolog distributions lead, in particular, by restricting the proportion of higher homologs - in general to lowering the cold-characteristic product values. In the particular embodiment of the present invention described here, this measure of the earlier application according to P 3802027.0 (D 8083) is additionally used. The result of the action according to the invention are then fatty alcohol ethoxylates with further improved and thus overall optimized cooling properties. For details of this work with a preferably limited increased amount of alkaline catalysts in the fatty alcohol ethoxylation step, reference is made to the information in the earlier application mentioned P 3802027.0 (D 8083). In order to complete the disclosure of the invention also in the context of the present description, the essential elements of this older proposal are summarized below.

As finely divided solids for precipitating the salt phase in the reaction product, preference is given to using organic and / or inorganic filter aids which are dispersed in the alkyl polyglycol ether reaction product before the salt phase crystallizes out. The finely divided filter aids are preferably used in amounts of about 0.3 to 2% by weight, in particular in amounts of about 0.5 to 1% by weight, based in each case on the alkyl polyglycol ether formed. Mixtures of inorganic and organic material, preferably in the range of about 3: 1 to 1: 3, can in particular be used as filter aids. A suitable inorganic filter aid is, for example, diatomaceous earth, organic filter aids are, for example, wood flour and / or finely powdered cellulose.

After completion of the ethoxylation, partial neutralization, for example up to about pH 8, is carried out in the presence of the filter aids, and then bleaching is carried out by adding, in particular, hydrogen peroxide, whereupon the full neutralization of the reaction product to pH values in the range of about 6, 5 to 7.5 is made. The neutralization stage and precipitation of the salt phase on the surface of the dispersed filter aid are preferably carried out in the temperature range from about 50 to 110.degree. The amounts of basic catalyst used for the ethoxylation of the sterically unhindered alcohols in this process are generally at least about 0.5% by weight, calculated as sodium methylate and based on the total mixture of alcohol and ethylene oxide, with amounts in the range from about 0.5 to 1.5% by weight, and in particular those in the range from about 0.8 to 1.1% by weight, can be particularly preferred. The technical teaching is not restricted to working with sodium methylate. Other known basic alkali metal catalysts can also be used in equivalent proportions. The neutralization of the catalyst in the reaction product is carried out with organic and / or inorganic acids. Examples include gluconic acid, glycolic acid, acetic acid, formic acid, benzoic acid, lactic acid, oxalic acid, citric acid, propionic acid, phosphoric acid, methanesulfonic acid and / or diglykoic acid. Strongly corrosive acids, for example sulfuric acid or hydrochloric acid, are of no importance in practice.

After the neutralization is complete, the ethoxylate, in which the filter aid and the salt formed are homogeneously distributed, is pumped to the filtration stage. The filtration can take place both through flow filters and through filter presses and through rotary filters. Particularly low-salt ethoxylates are obtained if the filtration under nitrogen is carried out at temperatures higher than 80 ° C.

B e i s p i e l e

For the preparation of the fatty alcohol ethoxylates described in the examples and comparative examples below, the amounts of fatty alcohol, ethylene oxide and catalyst given in the examples are approx. 3 to 4 in an autoclave at 170 to 180 ° C. with a reaction pressure of 2 to a maximum of 5 bar Hours implemented.

After the alkoxylation reaction has ended, the fatty alcohol ethoxylate is transferred to a neutralization container equipped with a stirrer and the product is neutralized at 90 ° C. with lactic acid, so that the reaction product finally has a pH (1% of the product in 99% deionized water ) from 6.5 to 7.5. In the examples in which the amount of sodium methylate used for the alkoxylation reaction (based on the total amount of alcohol and ethylene oxide) exceeds 0.5% by weight, the alkoxylation product becomes after addition of a maximum of 1% by weight of filter aid and subsequent neutralization filtered with lactic acid.

The determination of the hydrophilicity (cloud point,

Turbidity temperature, turbidity titration number) of the ethoxylate takes place according to D IN 53917.

Comparative Example 1

A from palm kernel oil by transesterification with. Methanol and fractionation of the reaction product of fatty acid methyl esters obtained in the chain length range C 12 to C 18 were mixed with hydrogen in a continuously operating hydrogenation system over a fixed bed catalyst containing copper at a pressure of 250 bar and a temperature of 240 C with hydrogen Fatty alcohol of the C chain length range mentioned and methanol implemented. After distilling off the methanol, the fatty alcohol had the following key figures:

Freezing point: 23 C

example 1

In a second experiment, the same methylated palm kernel fatty acid was hydrogenated in a continuously operating hydrogenation system over a fixed bed catalyst containing chromium / zinc. The pressure was 250 bar and the temperature 300 C. Under these conditions, the double bonds present in the carbon chain of the methyl ester were retained, and a fatty alcohol was formed which, after the methanol formed had been distilled off, had the following characteristic numbers:

Freezing point: 17 C

The four coconut alcohols "Type I to Type IV" are used for the examples below. Types I and III correspond to the definition according to the invention, while types II and IV are largely free of olefinically unsaturated C 18 alcohols. Coconut alcohol (type 1)

Hydroxyl number: 267 Iodine number: 12

C chain distribution:

C chain distribution: C 12 52.0

C 14 21.3

C 16 9.0

C 18 2.1

C 18 '15.6 Coconut alcohol (type IV)

Hydroxyl number: 265 Iodine number: 0.3

C chain distribution:

569.9 g of coconut alcohol (type I) were reacted with 830.1 g of ethylene oxide and 12.6 g of sodium methylate (30% in methanol, corresponds to 0.27% by weight of sodium methylate based on the total amount of alcohol and ethylene oxide). An ethoxylate with the following characteristics was obtained:

t a molecular weight of 400

The product, which corresponds to a fatty alcohol 7EO adduct, was cooled to -10 ° C. until it was solid. The product was then stored at 22 ° C. for 24 hours. After this time the product was liquid. Comparative Example 2

565.5 g of coconut alcohol (type I I) were reacted with 834.5 g of ethylene oxide and 12.6 g of sodium methylate (30% in methanol, corresponding to 0.27% by weight of sodium methylate based on the total amount of alcohol and ethylene oxide). An ethoxylate with the following characteristics was obtained:

a molecular weight of 800

The product, which corresponds to a fat-alcohol-7EO adduct, was cooled to -10 ° C. until it was solid. The product was then stored at 22 ° C. for 1 week. After that time the product was still solid.

Example 3

483.8 g of coconut alcohol type I) were reacted with 916.2 g of ethylene oxide and 7.0 g of sodium methylate (30% ϊg, in methanol, corresponding to 0.15% by weight of sodium methylate, based on the total amount of alcohol and ethylene oxide). An ethoxylate with the following characteristics was obtained:

a molecular weight of 1000 The product, which corresponds to a fatty alcohol 9EO adduct, was cooled to -10 ° C. until it was solid. The product was then stored at 25 ° C. for 24 hours. After this time the product was already liquid.

Comparative Example 3

483.8 g of coconut alcohol (type II) were reacted with 916.2 g of ethylene oxide and 7.0 g of sodium methylate (30% in methanol, corresponds to 0.15% by weight of sodium methylate based on the total amount of alcohol and ethylene oxide) . An ethoxylate with the following characteristics was obtained:

a molecular weight of 1100

The product, which corresponds to a fatty alcohol 9EO adduct, was cooled to -10 ° C until solid. The product was then stored at 25 ° C. for 1 week. After that time the product was still solid.

Example 4

567.5 g of coconut alcohol (type III) were reacted with 832.5 g of ethylene oxide and 12.6 g of sodium methylate (30% in methanol, corresponds to 0.27% by weight of sodium methylate based on the total amount of alcohol and ethylene oxide). An ethoxylate with the following characteristics was obtained: t a molecular weight of 500

The product, which corresponds to a fatty alcohol koho-7EO adduct, was cooled to -10 ° C until solid. The product was then stored at 22 ° C. for 24 hours. After this time the product was liquid.

Comparative example! 4

567.5 g of coconut alcohol (type IV) were reacted with 832.5 g of ethylene oxide and 12.6 g of sodium methylate (30% in methanol, corresponding to 0.27% by weight of sodium methylate, based on the total amount of alcohol and ethylene oxide). An ethoxylate with the following characteristics was obtained:

OHZ 109

% H ₂ 0 0.25

Density (70 ° C) 0.9464

Turbidity temperature 81 C.

(5 g in 25 g 25-

% butyl diglycol)

% Polyethylene glycol 2.1 with a molecular weight of 700

The product, which corresponds to a FettaIkoho! -7EO adduct, was cooled to -10 ° C until solid. The product was then stored at 22 ° C. for 24 hours. After that time the product was still solid. Comparative Example 5

An oxo alcohol of carbon chain length C 14 / C 15 with 7 moles of ethylene oxide per mole of alcohol was cooled to -10 ° C until it was solid. The product was then stored at 22 ° C. for 4 weeks. The product was still solid after this time.

Comparative Example 6

An oxo alcohol of carbon chain length C 12 / C 13 with 7 moles of ethylene oxide per mole of alcohol was cooled to -10 ° C until it was solid. The product was then stored at 22 C for 24 hours. The product was liquid after this time.

Claims

P a t e n t a n s r u c h e

New fatty alcohol mixtures R. OH natural, in particular purely vegetable origin and their ethoxylates with improved cold behavior and the general formula

R m -ix -0- (CH 2_CH -.2O) x -H, in which x is a number from 2 to 10, preferably from 3 to 9, and R. - For selected mixtures of saturated and olefinically unsaturated fatty alcohol hydrocarbon residues in the ranges C 6 to 20 or

C 12 to 20 stands for the chain length ³ en range R m .ix =

C 6 to 20 of the following specification I and for the chain length range R. = C 12 to 20 correspond to specification II below:

Specification I

structurally analogous to% by weight

0.1 - 0.6 2.5 - 10

-, 0 - l4

37-52

10-20

6-10

1 - 5

5-23

1 - 4

0.1 - 1 0.1 - 1 specification

structurally analogous to% by weight

Fatty alcohol mixtures and their ethoxylates according to Claim 1, characterized in that they are obtained by selective hydrogenation of vegetable fats and oils or corresponding mixtures of fatty acids, preferably of purely vegetable origin and / or their esters with lower alcohols while maintaining the natural distribution of the saturated as well as possible the mono- and poly-olefinically unsaturated hydrocarbon residues and optionally subsequent ethoxylation - preferably in the presence of alkaline catalysts - have been prepared.

Fatty alcohol mixtures and their ethoxylates according to Claims 1 and 2, characterized in that in the fatty alcohol mixtures of specification I the ratio of

^{C 1 8} 'is 78%.

C 18 '+ C 18 "

Fatty alcohol ethoxylates according to Claims 1 to 3, characterized in that they are obtained by reacting the fatty alcohol mixtures R. -OH with ethyl oxide at elevated temperatures and in the presence of such increased amounts of basic alkali metal compounds as catalysts are that in the neutralization stage salt precipitation occurs as an undissolved solid phase, the neutralization step being carried out in such a way that the salt phase was precipitated in the presence of finely divided solids dispersed in the reaction product.

5. Use of fatty alcohol mixtures R. -OH where the

The rest R m .ix - corresponds to the specifications I or II given in claim 1 for the production of ethoxylates with improved flowability at low temperatures, in particular in the range above room temperature and in general

Formula R m .ix -0- (CH_ 2CH_ 20) x -H, in which R m .ix - the anσ -eg ^a plane

Has meaning and x is a number from 2 to 10, preferably from 3 to 9.

6. Use natural of ethoxylates of selected fatty alcohol mixtures, preferably purely vegetable origin with the alig ⁼ emeinen Forme! R m .ix -O-CCH 2-CH-iO) x -H, in which R m.ix - corresponds to the specifications I or II specified in claim 1 and x averages from 2 to 10, preferably from 3 to 9 means as a surfactant component with improved low-temperature behavior, in particular in the area of the room temperature.

7. Use according to claim 6, characterized in that the ethoxylates of the specified general formula are used as non-ionic surfactant components in liquid formulations.