EP3215593A1

EP3215593A1 - Use of 3,3'-dimethoxy-4,4'-dihydroxystilbenes as a flavoring substance

Info

Publication number: EP3215593A1
Application number: EP15790939.1A
Authority: EP
Inventors: Ralf Pelzer; Carolin REGENBRECHT
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 2014-11-07
Filing date: 2015-11-06
Publication date: 2017-09-13
Also published as: CN107074705A; WO2016071475A1; JP2017538807A; US20170334820A1; MX2017005877A

Abstract

The invention relates to the use of 3,3'-dimethoxy-4,4'-dihydroxystilbenes as an odorous substance, in particular for developing a vanillin aroma under the effect of light. The invention further relates to compositions which contain the 3,3'-dimethoxy-4,4'-dihydroxystilbenes and additionally a carrier material, to fragrance compositions and/or an odorant material which contains the aforementioned compound, and to a method for providing or changing the aroma of compositions by adding the aforementioned compound to said compositions. The invention additionally relates to a method for obtaining 3,3'-dimethoxy-4,4'-dihydroxystilbenes from lignin-containing compositions.

Description

Use of 3,3'-dimethoxy-4,4'-dihydroxystilbene as a flavoring agent

The present invention relates to the use of 3,3'-dimethoxy-4,4'-dihydroxystilbene as an odorant, in particular for the development of a vannilin odor under the action of light. Furthermore, the invention relates to a composition containing 3,3'-dimethoxy-4,4'-dihydroxystilbene and additionally a carrier material, fragrance compositions and / or a fragrance material containing said compound and a method for imparting or changing a smell of compositions by the addition of said compound to these compositions. In addition, the invention relates to a process for the recovery of 3,3'-dimethoxy-4,4'-dihydroxystilbene from ligninhaltigen

Compositions.

BACKGROUND OF THE INVENTION

Odor substances are of great commercial interest, in particular in the field of cosmetics and as an additive in detergents and cleaners. However, that is

Extraction of fragrances from natural sources usually expensive and the amounts available limited. In addition, the purity or production of these fragrances often varies due to changing environmental conditions in the production of the raw materials from which they are isolated. There is therefore great interest in new ones

To find odors that can be obtained from readily available natural sources, which are available in large quantities. Often in the odor search chemical compounds of interest, which can be used on the basis of their characteristic odor as a substitute for natural substances, where substitute and natural substance not

necessarily have to have a chemical-structural similarity. Since even small changes in the chemical structure cause massive changes in the sensory properties such as smell and taste, the targeted search for substances with certain sensory properties, such as a certain smell, is extremely difficult. The search for new ones

Odors is therefore usually tedious without knowing whether a substance with the desired smell is actually found.

Hydroxystilbene derivatives such as (E) -3,3'-dimethoxy-4,4'-dihydroxystilbene are

basically known. For example, Dhyani et al., Applied Radiation and Isotopes, 201 1, Vol. 69, pp. 996-1001, describe the stereoselective synthesis of (Ε) -3,3'-dimethoxy-4,4'-dihydroxystilbene by a McMurry cross-coupling reaction. Reaction starting from vanillin. In addition to the synthetic methods, it is also known that (E) -3,3'-dimethoxy-4,4'-dihydroxystilbene can be obtained from natural sources, as this occurs naturally in plants. Hajdü et al., J. Nat. Prod., 1998, Vol. 61, pp. 1298-1299, describe the extraction, isolation and characterization of (E) -3,3'-dimethoxy-4,4'-dihydroxystilbene from Leuzea carthamoides (Asteraceae).

Furthermore, (E) -3,3'-dimethoxy-4,4'-dihydroxystilbene is contained, for example, in extracts and the syrup of maple trees, in particular the sugar maple - see WO 2012/021981, WO 2012/021983 A1 and WO 2012/055010 A1. These documents describe u. A. the potential use of these extracts and syrups, which in addition to (E) -3,3'-dimethoxy-4,4'-dihydroxystilbene contain many other phytochemicals, in the cosmetic and pharmaceutical field as well as in foodstuffs.

SUMMARY OF THE INVENTION

The present invention has for its object to provide new odors, which can be obtained from readily available natural sources or can be synthesized from readily available educts on a large scale. We are looking for compounds which have advantageous sensory properties, ie. H. have an intense, pleasant smell, especially a vanilla-like odor. The new odors should also be toxicologically safe.

Surprisingly, it has been found that the compound 3,3'-dimethoxy-4,4'-dihydroxystilbene (I)

has a vanilla-like odor and has the desired beneficial sensory properties. Furthermore, it has surprisingly been found that the typical vanilla-like odor of 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) intensified under the action of sunlight. 3,3'-Dimethoxy-4,4'-dihydroxystilbene (I) can also be obtained in large quantities from lignin-containing compositions.

The present invention thus relates to the use of 3,3'-dimethoxy-4,4'-dihydroxystilbene as an odorant. Furthermore, the present invention relates to the use of 3,3'-dimethoxy-4,4'-dihydroxystilben for the development of a vanillin odor under the action of light.

Furthermore, the present invention relates to the use of 3,3'-dimethoxy-4,4'-dihydroxystilbene as a constituent of a composition which additionally contains a carrier material, wherein the composition is selected from

Detergents, laundry preparations, cleaning preparations, perfume-containing

Toiletries, fragrance dispensers and perfumes. Furthermore, the present invention relates to a fragrance composition and / or a fragrance material containing 3,3'-dimethoxy-4,4'-dihydroxystilbene and a carrier material, wherein the fragrance composition and / or the

Fragrance material containing the respective 3,3'-dimethoxy-4,4'-dihydroxystilbene in an amount which gives the fragrance composition and / or the fragrance material a smell or alters the odor of the fragrance composition and / or the fragrance material.

Furthermore, the present invention relates to a method for imparting or changing a smell of a composition in which the

Composition 3,3'-dimethoxy-4,4'-dihydroxystilben in an amount that gives the composition a smell or changes the odor of the composition.

Furthermore, the present invention relates to a process for the recovery of 3,3'-dimethoxy-4,4'-dihydroxystilbene from aqueous, alkaline ligninhaltigen

Compositions comprising the aqueous, alkaline lignin-containing

Composition, optionally treated with alkalis or oxidatively, treated with a solid adsorbent which separates adsorbent from the aqueous, alkaline lignin-containing composition and then the adsorbent to obtain the 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) with an organic

Solvents to give a 3,3'-dimethoxy-4,4'-dihydroxystilbene-containing eluate.

3,3'-Dimethoxy-4,4'-dihydroxystilbene is characterized by its advantageous

organoleptic properties, in particular by a pleasant vanilla-like odor. Therefore, 3,3'-dimethoxy-4,4'-dihydroxystilbene can be used advantageously as an odorant or as part of a fragrance composition and / or a fragrance material. 3,3'-dimethoxy-4,4'-dihydroxystilbene is characterized in particular by the fact that intensified the typical vanilla-like odor under the influence of sunlight. 3,3'-Dimethoxy-4,4'-dihydroxystilbene can also be very well applied to textiles or textile fibers and remains on this long stick.

Due to its physical properties, 3,3'-dimethoxy-4,4'-dihydroxystilbene has very good, practically universal dissolution properties for other odorants or other commercially available ingredients, as described in US Pat

Perfume compositions, especially in perfumes, are used.

3,3'-Dimethoxy-4,4'-dihydroxystilbene can be obtained from readily available natural sources as well as synthesized from inexpensive and readily available starting materials.

3,3'-Dimethoxy-4,4'-dihydroxystilbene is expected to be of very low toxicity, since this compound belongs to a group of phytochemicals that have no appreciable toxicity. This group includes, for example, the structurally very similar compound resveratrol, which has been extensively studied pharmacologically and is classified as toxicologically harmless (Cottart et al., Mol. Nutr. Food Res., 2010, Vol. 54 (1), pp. 7). 16). DETAILED DESCRIPTION OF THE INVENTION

The compound 3,3'-dimethoxy-4,4'-dihydroxystilbene (I)

may due to the double bond as E-isomer (E) -3,3'-dimethoxy-4,4'-dihydroxystilbene (IE) or as Z-isomer (Z) -3,3'-dimethoxy-4,4'-dihydroxystilben (lZ)

(IE) (LC) or as an E / Z isomer mixture. The present invention thus relates to both the use of the E isomer and the use of the Z isomer, as well as the use of mixtures thereof. The term "3,3'-dimethoxy-4,4'-dihydroxystilbene" includes both the pure E or pure Z isomer and mixtures in which the isomers are present in equal amounts or contain one of the isomers in excess ,

In a preferred embodiment of the invention, the compound (I) is in the form of a pure E isomer or as an E / Z isomer mixture which predominantly contains the E isomer (I-E). To be more specific, the compound (I) is present as a pure E isomer or as an E / Z isomer mixture containing the E isomer (IE) at least 60 wt .-%, in particular at least 80 wt .-% and especially to at least 90 wt .-%, based on the total amount of isomers IE and LC, contains.

The compound (I) is suitable in various degrees of purity for

Use as an odorant. For the use according to the invention as an odorant, the purity of the compound (1) is therefore not particularly limited. The compound (I) preferably has a purity of at least 50%, in particular of at least 80% and especially of at least 90%. The above-mentioned preferred embodiments may be arbitrarily combined with each other.

Accordingly, in a preferred embodiment of the invention, the compound (I) has a purity of at least 90%, this being present as a pure E isomer or as an E / Z isomer mixture containing at least 90% of the E isomer (IE). - contains%.

As already mentioned, 3,3'-dimethoxy-4,4'-dihydroxystilbene has advantageous sensory properties, in particular a pleasant odor. Concretely, 3,3'-dimethoxy-4,4'-dihydroxystilbene has a pungent vanilla-like odor comparable to that of vanillin or ethyl vanillin.

Surprisingly, it has been found that the pungent vanilla-like odor of 3,3'-dimethoxy-4,4'-dihydroxystilbene is intensified by the action of light. For this reason, the invention also relates to the use of the compound (I), as defined above, for the development of a vanilla-like odor under the action of light.

In the context of the present invention, the term "exposure to light" is understood to mean a process in which the compound (I) is exposed to the light of an artificial light

Light source or exposed to sunlight. In general, an intensification of the vanilla-like odor occurs after a brief exposure to light, with a

Duration of exposure in the range of 1 to 60 minutes or 1 to 30 minutes is sufficient to achieve a significant intensification of the vanilla-like odor. Of course For example, longer exposure times can lead to a significant intensification of the vanilla-like odor.

Suitable artificial light sources may be light sources whose emitted light is the spectral range of the visible light and the adjacent thereto

Spectral ranges includes, or light sources that emit light of a specific range of visible light and the adjacent thereto spectral ranges. Suitable artificial light sources are for example heat radiators, such as incandescent lamps, gas discharge lamps, such as high-pressure mercury vapor lamps, high-pressure sodium vapor lamps, xenon gas discharge lamps or metal halide lamps, and light-emitting diodes. In a preferred embodiment of the invention, for the development of a vanilla-like odor, the compound (I) is exposed to sunlight for a certain period of time, for example 1 to 60 minutes, in particular 1 to 30 minutes.

Intensive olfactory impressions are to be understood as meaning those properties of aroma chemicals which enable a succinct perception even in very small gas chamber concentrations. The intensity can be determined via a threshold determination. A threshold value is that concentration of a substance in the relevant gas space, in which a representative sample panel just barely perceives an odor impression, although this no longer needs to be defined. A class of substances that is probably one of the most odor-intensive classes of substances known, ie has very low odor thresholds, are thiols whose threshold is often in the ppb / m ³ range. The aim of the search for new aroma chemicals is to find substances with the lowest odor threshold possible in order to allow the lowest possible application concentration. The closer one gets to this goal, the more one speaks of "intensive" odorants or aroma chemicals.

"Beneficial sensory properties," or "pleasant odor," are hedonistic expressions that describe the beauty and conciseness of an aroma impression mediated by an aroma chemical.

"Beauty" and "Prägnanz" are terms that are familiar to the expert, a perfumer. Beauty usually refers to a spontaneously evoked, positively felt, pleasant sensory impression. "Nice" does not have to be synonymous with "sweet". "Beautiful" may also be the smell of musk or sandalwood. "Prägnanz" usually refers to a spontaneously evoked Sensory impression, which - in the same sample panel - produces a reproducible same memory of something specific.

For example, a substance may have a smell that spontaneously resembles that of an "apple": the smell would then be concise after "apple". If this smell of apple would be very pleasant, because the smell is reminiscent of a sweet, solid apple, for example, the smell would be "nice." But the smell of a typical sour apple can also be very succinct In the example, therefore, a beautiful and pungent smell of apple, so this substance has a particularly advantageous sensor.

Furthermore, the present invention relates to the use of 3,3'-dimethoxy-4,4'-dihydroxystilbene, as defined above, as part of a composition which typically has at least one flavor, i. Odor and additionally contain a carrier material. Such compositions are selected, for example, from detergents, laundry detergents, cleaners, fragrance-containing

Hygiene articles, such as diapers, sanitary napkins, underarm pads, paper towels,

Wet wipes, toilet paper, handkerchiefs and the like, fragrance dispensers, such as room fresheners and perfumes.

For the formulation of these compositions is usually 3,3'-dimethoxy-4,4'-dihydroxystilbene, as defined above, optionally together with one or more other flavoring agents, to an existing preparation which has previously no flavorings or one or more of the compounds ( I) different

Flavorings, added. Usually, these compositions additionally contain a carrier material consisting of a compound, a mixture of

Compounds or other additives may have, which have no or no appreciable sensory properties. The carrier material may also be a compound or an additive, the one or more noticeable

having sensory properties, or being a mixture of compounds containing at least one flavor other than the compounds (I), and optionally at least one further compound having no appreciable sensory properties. The carrier material may be a compound, a mixture of compounds or other additives having the above-mentioned properties.

Suitable carrier materials include liquid or oily carrier materials and waxy or solid carrier materials. Suitable liquid or oily carrier materials are, for example, selected from alcohols, such as ethanol, water, aliphatic diols and polyols having a melting point below 20 ° C., such as ethylene glycol, glycerol, diglycerol, propylene glycol or dipropylene glycol, cyclic siloxanes such as hexamethylcyclotrisiloxane or

Decamethylcyclopentasiloxane, vegetable oils, such as fractionated coconut oil or esters of fatty alcohols with melting temperatures below 20 ° C, such as tetradecyl acetate or tetradecyllactate, and Alyklester of fatty acids with melting temperatures below 20 ° C, such as isopropyl myristate.

Suitable waxy or solid support materials are, for example, selected from fatty alcohols with melting temperatures above 20 ° C., such as myristyl alcohol, stearyl alcohol or cetyl alcohol, polyols having melting temperatures above 20 ° C., fatty acid esters with fatty alcohols which have a melting temperature above 20 ° C., such as wool wax, beeswax, Carnauba wax, candelilla wax or Japan wax, waxes produced from petroleum, such as hard paraffin, water-insoluble porous minerals, such as silica gel, silicates, for example talc, microporous crystalline aluminosilicates (zeolites), clay minerals, for example bentonite, or phosphates, for example sodium tripolyphosphate, paper, cardboard, wood, Textile composite or nonwovens made from natural and / or artificial fibers.

Suitable support materials are, for example, also selected from water-soluble polymers, such as polyacrylic acid esters or quaternized polyvinylpyrrolidones, or water-alcohol-soluble polymers, such as special thermoplastic polyesters and polyamides. The polymeric carrier material may be in various forms, e.g. B in the form of a gel, a paste, as solid particles, such as microcapsules, or brittle coatings. As a rule, the amounts of 3,3'-dimethoxy-4,4'-dihydroxystilbene, as defined above, in these compositions correspond to the customary customary market amounts of fragrances in formulations. To be more specific lies the

Use amount of 3,3'-dimethoxy-4,4'-dihydroxystilbene, as defined above, in the range of 0.001 to 50 wt .-%, in particular in the range of 0.01 to 20 wt .-% and especially, in the range of 0.1 to 10 wt .-%, based on the total weight of the composition.

In a particularly preferred embodiment of the present invention, 3,3'-dimethoxy-4,4'-dihydroxystilbene, as defined above, as an ingredient in

Compositions that are at least partially exposed to sunlight due to their intended use, such as in

Detergents, laundry detergents, cleaners or perfume-containing

Hygiene articles. In a particularly preferred embodiment of the present invention, 3,3'-dimethoxy-4,4'-dihydroxystilbene, as defined above, is used as an ingredient in laundry detergents and laundry detergents. The advantage of this is particularly advantageous By virtue of the fact that compound (I) adheres very well to natural, synthetic or semi-synthetic fiber materials commonly used in the manufacture of textiles. These fiber materials can in principle all

Natural fibers and / or man-made fibers, which can be processed in textile production processes, contain or consist of these.

The natural fibers suitable for textile production are, for example, vegetable fibers, such as cotton fibers, flax fibers or hemp fibers, animal fibers, such as wool, cashmere or silk.

The synthetic fibers suitable for textile production are, for example, fibers of natural polymers, such as viscose, lyocell or rubber, or fibers of synthetic polymers, such as polyester, polyacrylonitrile, polypropylene or

Polyamide.

Detergents and laundry detergents in the context of the present invention are understood to mean those agents which are used for cleaning flexible materials with high absorbency, e.g. of materials with a textile

Character.

Examples of flexible, high absorbency materials are those which contain or consist of natural, synthetic or semi-synthetic fiber materials as previously defined and which consequently generally have, at least in part, a textile character. The fibrous or made of fibers

In principle, materials can be used by anyone in the use or manufacture and

Processing occurring form present. For example, fibers may be present randomly in the form of flakes or debris, ordered in the form of threads, yarns, threads, or in the form of fabrics such as nonwovens, loden fabrics or felt, fabrics, knitted fabrics in all conceivable weave types. The fibers may be raw fibers or fibers at any stage of processing.

Due to the fact that the compound (I) adheres very well to natural, synthetic or semi-synthetic fiber materials, the amount of 3,3'-dimethoxy-4,4'-dihydroxystilbene used as the odoriferous ingredient in detergents and laundry detergents is necessary to achieve the desired odor effects, usually relatively low. To be more specific, the amount of 3,3'-dimethoxy-4,4'-dihydroxystilbene as defined above in laundry detergents and laundry detergents is usually in the range of 0.0001 to 20% by weight, more preferably in the range of 0.001 to 3% 10% by weight and especially, in the range of 0.01 to 5% by weight, based on the total weight of the composition. Depending on their intended use, the compositions in which 3,3'-dimethoxy-4,4'-dihydroxystilbene, as defined above, is used as an odiferous ingredient, may contain other auxiliaries and / or additives, such as detergents or mixtures of Detergents, thickeners, like

Polyethylene glycols having a number average molecular weight of 400 to 20,000 Da, lubricants, binding or agglomerating agents, such as sodium silicates, dispersants, builder salts, water softeners, fillers, pigments, colorants, optical

Brightener, dirt carrier and the like. In particular, laundry detergents and laundry care compositions generally contain a plurality of specific additives, for example surfactants, water softeners, builders, wash alkalis, enzymes, soil carriers, defoamers, adjusters, bleaching agents or optical brighteners. Furthermore, the present invention relates to a fragrance composition and / or a fragrance material containing 3,3'-dimethoxy-4,4'-dihydroxystilbene or an E / Z isomer mixture thereof as defined above, and a carrier material, wherein the fragrance composition and / or the fragrance material contains the respective 3,3'-dimethoxy-4,4'-dihydroxystilbene as defined above in an amount which gives the fragrance composition and / or fragrance material an odor or alters the odor of the fragrance composition and / or fragrance material.

The amounts of 3,3'-dimethoxy-4,4'-dihydroxystilbene required for this purpose depend on the nature and intended use of the fragrance composition and / or the fragrance material and can therefore vary widely.

Apart from that, the total concentration of 3,3'-dimethoxy-4,4'-dihydroxystilbene in the fragrance composition of the invention and / or the

fragrance material according to the invention is not particularly limited and can be adapted in a wide range of the respective intended use. As a rule, the customary market amounts of fragrance are used. Usually, the total amount of 3,3'-dimethoxy-4,4'-dihydroxystilbene in the

Fragrance composition according to the invention and / or the fragrance material according to the invention in the range of 0.0001 to 20 wt .-% and in particular in the range of 0.001 to 10 wt .-%.

Typical fields of application of the fragrance compositions and / or perfume materials according to the invention are detergents, fabric care products, cleaning compositions, preparations of fragrances for the human or animal body, for rooms such as kitchens, wet rooms, cars or trucks, for real or artificial plants, for Clothing, footwear and shoe inserts, furniture, carpets, room humidifiers, air fresheners or perfumes.

In particular, the fragrance compositions and / or fragrance materials of the invention find application in detergents, fabric care products as well as in fragrance preparations for clothes, shoes, furniture or carpets.

The invention also includes odorant combinations which comprise 3,3'-dimethoxy-4,4'-dihydroxystilbene, as defined above, as component A and at least one further compound known as odorant or flavoring agent as component B, for example one or more the following compounds B1 to B1 1:

B1: methyl dihydrojasmonate (e.g., hedione),

B2: 4,6,6,7,8,8-hexamethyl-1, 3,4,6,7,8-hexahydrocyclopenta [g] benzopyran (e.g.

Galaxolide ™)

B3: 2-methyl-3- (4-tert-butylphenyl) propanal (Lysmeral ™),

B4: 2-methyl-3- (4-iso-propylphenyl) propanal (cyclamenaldehyde),

B5: 2,6-dimethyl-7-octene-2-ol (dihydromyrcenol),

B6: 3,7-dimethyl-1,6-octadien-3-ol (linalool),

B7: 3,7-dimethyl-trans-2,6-octadiene-1-ol (geraniol),

B8: 2,3,8,8-Tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone (Iso E

Super ™)

B9: alpha-hexylcinnamaldehyde,

B10: 3,7-dimethyl-6-octene-1-ol (citronellol),

B1 1: alpha, or beta-, or delta-damascone.

As formulations of odorous substances, for example, the formulations disclosed in JP 1 1 -071312 A, paragraphs [0090] to [0092] are suitable. Also suitable are the formulations from JP 1 1 -0 35969 A, paragraphs [0039] to [0043]. Furthermore, the present invention relates to a method for imparting or changing a smell of a composition in which the

Composition 3,3'-dimethoxy-4,4'-dihydroxystilbene, as defined above, in an amount which gives the composition a smell or alters the odor of the composition. The required amounts of 3,3'-dimethoxy-4,4'-dihydroxystilbene depend on the nature and intended use of the composition and therefore can vary widely. As a rule, the amounts of 3,3'-dimethoxy-4,4'-dihydroxystilbene, as defined above, are

usually in the range of 0.0001 to 50 wt .-%, in particular in the range of 0.001 to 20 wt .-%, based on the total weight of the composition.

The present invention also relates to a process for the recovery of 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) from aqueous, alkaline ligninhaltigen Compositions. The process according to the invention is characterized in that the aqueous, alkaline lignin-containing composition, which has optionally been treated with alkalis or oxidatively, is treated with a solid adsorbent which separates the adsorbent from the aqueous, alkaline lignin-containing composition and then the adsorbent for obtaining the 3, 3'-dimethoxy-4,4'-dihydroxystilbene (I) treated with an organic solvent. In this case, an eluate is obtained which contains the 3,3'-dimethoxy-4,4'-dihydroxystilbene (I).

For the treatment of the aqueous, alkaline lignin-containing composition, which was optionally treated with alkalis or oxidatively, with a solid

Adsorbent, you can, for example, the solid adsorbent to the aqueous, alkaline lignin-containing composition. After a certain residence time, the solid adsorbent of the aqueous, alkaline ligninhaltigen

Separate composition. The separation may be carried out by conventional solid-liquid separation methods, e.g. by filtration, sedimentation or centrifugation.

Preferably, the aqueous alkaline lignin-containing composition is passed one or more times through a bed of the solid adsorbent, for example, a column packed with the adsorbent.

Preferably, to obtain 3,3'-dimethoxy-4,4'-dihydroxystilbene (I), an aqueous alkaline lignin-containing composition is selected from the solid

Adsorbent existing fixed bed, in particular passed through a packed with the solid adsorbent column.

Following adsorption, release of the 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) bound to the solid adsorbent is carried out by treatment with an organic solvent. Before the release of the 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) bound to the solid adsorbent, the adsorbent can be treated with an aqueous solution of an acid, in particular a mineral acid or an organic sulfonic acid. Suitable mineral acids are, for example, hydrochloric acid, nitric acid, perchloric acid, phosphoric acid, or sulfuric acid. Suitable organic sulfonic acids are especially methanesulfonic acid. A particularly preferred mineral acid is sulfuric acid. Preferably, the aqueous solution of the acid has an acid concentration in the

Range of 0.01 to 10 mol kg- ¹ , preferably in the range of 0.1 to 5 mol kg- ^1, in particular 0.1 to 2 mol kg- ¹ . Optionally, the solid adsorbent is washed with water before and / or after treatment with the aqueous dilute mineral acid. In principle, any aqueous

ligninhaltige compositions are used, which have an alkaline pH, wherein the pH is usually at least pH 8, in particular at least pH 9 or pH 10 and especially at least pH 1 1 or pH 12 and may also be pH 14.

In general, an aqueous alkaline lignin-containing composition, which has been previously treated with alkalis or oxidatively, can also be used in the process according to the invention. In the context of the present invention, this is an aqueous, alkaline lignin-containing composition which has been obtained by dissolving a lignin or lignin derivative in aqueous alkali and / or by partial oxidation, especially by electrolysis, of an aqueous, alkaline lignin-containing composition.

The lignin or lignin derivative used to prepare the aqueous, alkaline lignin-containing composition is selected, for example, from lignin from black liquor, kraft lignin, lignin sulphate, lignosulphonate, alkali lignin, sodalignin, organosolv lignin or corresponding residues obtained by a technical process such as pulp, Pulp or cellulose production incurred, eg Lignin from black liquor, from the sulfite process, from the sulfate process, from the

Organocell or Organosolv process, from the ASAM method, from the force method or from the natural-pulping method.

Accordingly, it is used in the aqueous, alkaline

lignin-containing composition to an aqueous solution or suspension obtained as a by-product in a technical process such as pulp, pulp or cellulose production, e.g. Black liquor, as well as the ligninhaltigen

Wastewater streams from the sulphite process, from the sulphate process, from the

The alkali or oxidatively treated aqueous, alkaline lignin-containing

As a rule, the composition has a pH of at least pH 8, frequently at least pH 9 or pH 10, in particular at least pH 1 1 or pH 12. The aqueous, lignin-containing composition, which has optionally been treated with alkalis or oxidatively, generally contains 0.5 to 30 wt .-%, preferably 1 to 15 wt .-%, in particular 1 to 10 wt .-% lignin, based on the

Total weight of the aqueous, lignin-containing composition.

The concentration of 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) in the aqueous lignin-containing compositions is typically in the range of 1 to 1500 mg / kg, more preferably in the range of 10 to 1000 mg / kg and especially in the Range from 50 to 750 mg / kg.

In a preferred embodiment of the process according to the invention, an aqueous lignin-containing wastewater stream from pulp, pulp or cellulose production is used as the aqueous, alkaline lignin-containing composition. In a particularly preferred embodiment of the process according to the invention, black liquor from the paper industry, pulp or cellulose production is used to prepare the aqueous, alkaline lignin-containing composition.

As alkalis or bases for the preparation of the aqueous, alkaline lignin-containing compositions or for adjusting the pH of the aqueous, alkaline lignin-containing compositions, especially inorganic bases can be used, e.g. Alkali metal hydroxides such as NaOH or KOH, ammonium salts such as ammonium hydroxide and alkali metal carbonates such as sodium carbonate, e.g. in the form of soda. Preference is given to alkali metal hydroxides, in particular NaOH and KOH. The concentration of inorganic bases in the aqueous, lignin-containing suspension or solution should not exceed 5 mol / L, in particular 4 mol / L, and is typically in the range from 0.01 to 5 mol / L, in particular in the range from 0.1 to 4 mol / L. Suitable solid adsorbents are, for example, basic aluminas,

Clays, cross-linked organic polymer resins, e.g. crosslinked basic polymer resins or crosslinked cationic polymer resins, activated carbon, especially non-chemically activated carbon or chemically pretreated activated carbon, e.g. basic impregnated or washed activated carbon.

Preferably, the solid adsorbent is selected from crosslinked organic

Polymer resins, in particular among crosslinked basic organic polymer resins and crosslinked cationic polymer resins, and in particular under activated carbon, in particular steam-activated activated carbon. The crosslinked basic or cationic organic polymer resins are preferably anion exchangers or anion exchanger resins. The preferred anion exchangers or anion exchange resins generally have functional

Groups which are selected from tertiary amino groups, quaternary ammonium groups and quaternary phosphonium groups. The anion exchangers used are particularly preferably crosslinked, organic polymer resins which contain cationic groups, for example quaternary ammonium groups, quaternary phosphonium groups, imidazolium groups or guanidinium groups,

especially quaternary ammonium groups or imidazolium groups. Suitable anion exchange resins are the anion exchange resins described in WO2014 / 006108, to which reference is made in their entirety.

The basic impregnated activated carbon is activated carbon pretreated with bases as defined above. Preferably, the base-impregnated activated carbon is activated carbon, which has been pretreated with NaOH. For impregnation, the activated carbon is usually washed several times with an aqueous solution of the base.

In a particularly preferred embodiment of the process according to the invention, the solid adsorbent is selected from non-chemically activated or basic impregnated or washed activated carbons.

The non-chemically activated carbon preferably is activated steam activated with water vapor. When activated with steam activated carbon is usually to commercial activated carbons such as recordable as CAL ^® or Aquacarb ^® 207C of the company Chemviron Carbon, Norit ^® ROY 0.8 and Norit ^® GAC 1240 Norit or Epibon ^® A 8x30 or Hydraffin ^® 30N of Company Donau Carbon. The treatment of the lignin-containing suspension or solution with the solid adsorbent, in particular the anion exchange resin or the untreated or the basic impregnated activated carbon, is usually carried out at a temperature in the range of 10 to 100 ° C, preferably in the range of 10 to 70 ° C. , in particular in the range of 15 to 50 ° C.

In a preferred embodiment of the process according to the invention, the aqueous, basic lignin-containing material is charged to load the solid adsorbent

A composition which has optionally been treated with alkalis or oxidatively, in the usual way by an adsorbent arrangement, i. by one or more

Fixed beds of the adsorbent, e.g. by one or more columns, which coincide with the

Adsorbent (eg an untreated or basic impregnated activated carbon) packed are, guided. The transmission can be done both descending and ascending. The passage is preferably carried out at a specific flow rate (specific load) in the range of 0.2 to 35 bed volumes per hour (BV / h), in particular in the range of 0.5 to 10 BV / h, especially in the range of 1 to 5 BV /H. The passage is preferably carried out at a linear velocity in the range of 0.1 to 50 m / h.

The relative amount of lignin-containing suspension or solution and solid adsorbent is usually selected so that at least 35% and in particular at least 50% of the contained in the aqueous alkaline composition 3,3'-dimethoxy-4,4'-dihydroxystilbens (I) from Adsorbent be adsorbed. The amount of aqueous, alkaline composition is usually from 1 to 100 times the amount, in particular from 2 to 50 times the amount of the bed volume. Depending on the degree of adsorption, the at the outlet of the adsorbent arrangement, e.g. the column packed with adsorbent, effluent still containing 3,3'-dimethoxy-4,4'-dihydroxystilbene (I), so that the effluent may optionally be applied to a further adsorbent arrangement, e.g. a column packed with adsorbent, can be passed.

The loading process may be followed by a washing step. Usually, an aqueous liquid is used to wash the loaded adsorbent. By an aqueous liquid is meant water or a mixture of water with a water-miscible organic solvent, wherein water

Main component of the mixture and in particular 90 vol .-% of the mixture. The pH of the aqueous liquid is usually in the neutral range, i. in the range of pH 6 to pH 8. The washing step is usually carried out at a temperature and at a pressure as defined above for the loading of the adsorbent.

If the loading of the adsorbent takes place in an adsorbent arrangement, the aqueous liquid, in particular water, will ascend or descend through the

Lead adsorbent arrangement. The amount of aqueous liquid, hereinafter also wash water, is usually 1 to 20 times that at this stage

Bed volume, in particular 2 to 10 times the bed volume. The washing water is usually passed through at a specific flow rate (specific load) in the range of 0.5 to 10 BV / h, in particular in the range of 1 to 8 BV / h or a linear velocity in the range of 0.1 to 50 m / h. The resulting wash water can contain small amounts of 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) and can then be combined with the incurred during loading 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) ,

Optionally, following the loading step or, in particular following the washing step and before the desorption, the adsorbent with an aqueous solution of an acid, in particular a mineral acid or a organic sulfonic acid, to protonate or neutralize the bound anionic 3,3'-dimethoxy-4,4'-dihydroxystilbene. Suitable mineral acids are, for example, hydrochloric acid, nitric acid, perchloric acid,

Phosphoric acid, or sulfuric acid. Suitable organic sulfonic acids are especially methanesulfonic acid. Particularly preferred mineral acid is sulfuric acid. The aqueous solution of the acid preferably has an acid concentration in the range from 0.01 to 10 mol kg ^-1 , preferably in the range from 0.1 to 5 mol kg ^-1, in particular from 0.1 to 2 mol kg ^-1 . If the loading of the adsorbent takes place in an adsorbent arrangement, the aqueous dilute acid, if appropriate after a washing step, will be passed through the adsorbent arrangement in ascending or descending order in order to protonate at most bound 3,3'-dimethoxy-4,4'-dihydroxystilbene or to neutralize. The amount of aqueous dilute acid is usually 0.1 to 10 times that

Bed volume, in particular 0.5 to 5 times the bed volume. The passage of the aqueous dilute mineral acid is usually carried out at a specific flow rate (specific load) in the range of 0.5 to 10 BV / h, in particular in the range of 1 to 8 BV / h. The treatment with the aqueous dilute aqueous acid may be followed by another washing step with water. With regard to the amount of water and the flow rate, what has been said in the above-described washing step applies.

Subsequently, the adsorbent is eluted in a conventional manner to obtain the 3,3'-dimethoxy-4,4'-dihydroxystilbene (I). Suitable eluents are, above all, organic solvents, solutions of acids, in particular mineral acids, in organic solvents and solutions of acids, in particular

Mineral acids, in organic-aqueous solvent mixtures. The nature of the eluent naturally depends on the adsorbent used. In the case of ion exchangers, reference is made to WO 2014/006108 for elution. In general, it is done so that you have a suitable eluent, such as an organic

Solvent or a solution of an acid in an organic solvent or a solution of an acid in an organic-aqueous solvent mixture, passes through the adsorbent assembly, wherein the bound 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) is desorbed and eluted , If the loading of the adsorbent takes place in an adsorbent arrangement, after the loading and optionally the washing step and / or the treatment with the aqueous acid, an organic solvent or a solution of an acid in an organic solvent or a solution of an acid in an organic-aqueous Solvent mixture by the

Led adsorbent, wherein the bound, optionally neutralized or protonated 3,3'-dimethoxy-4,4'-dihydroxystilbene is desorbed and eluted. The amount of organic solvent is generally from 0.1 to 20 times the amount, in particular from 0.5 to 15 times the amount, for example, 1 to 10 times the amount of the bed volume. The eluent is generally passed through at a specific flow rate (specific load) in the range from 0.5 to 20 BV / h, preferably in the range from 0.5 to 10 BV / h, in particular in the range from 1 to 8 BV / H. If one

Anion exchange resin is used as a solid adsorbent, this usually has to be converted back to the OH-form before the next loading, e.g. by treating with an aqueous solution of an alkali metal hydroxide, e.g. with aqueous NaOH.

The organic solvents used for the elution may be water-miscible organic solvents, water-immiscible organic solvents, and mixtures thereof.

The water-miscible organic solvents are generally organic solvents that are immiscible with water at 22 ° C indefinitely or at least dissolve at 22 ° C in an amount of at least 200 g / L in water. These include, in particular, dimethyl sulfoxide, acetone, C 1 -C 4 -alkanols, such as methanol, ethanol, isopropanol, n-propanol, 1-butanol, 2-butanol or tert-butanol, alkanediols, such as glycol or 1,4-butanediol, alkylnitriles such as acetonitrile, but also cyclic ethers such as dioxane, methyltetrahydrofuran or tetrahydrofuran, nitrogen heterocycles such as pyridine or N-methylpyrrolidine and mixtures thereof. The water-miscible organic solvent is preferably C 1 -C 4 -alkanols and especially methanol.

The poorly water-miscible organic solvents are usually organic solvents which dissolve in water at 22 ° C in an amount of at most 50 g / L. These include especially aliphatic

Hydrocarbons, such as pentane, hexane, heptane, ligroin, petroleum ether or cyclohexane, halogenated hydrocarbons, such as dichloromethane, trichloromethane or

Carbon tetrachloride, aromatic hydrocarbons such as benzene, toluene or xylenes, halogenated aromatic hydrocarbons such as chlorobenzene or dichlorobenzenes, dialkyl ethers such as diethyl ether, methyl tert-butyl ether or dibutyl ether and

Mixtures thereof. The water-immiscible organic solvent is preferably aromatic hydrocarbons, in particular toluene or xylenes, and mixtures thereof.

With regard to the temperatures and the pressure during the elution, what has been said for the loading applies. The elution can be performed both ascending and descending become. The elution can be in the same direction as the loading or

opposite to this.

Optionally, prior to the elution step, the water present in the pores and between the adsorbent particles or, if a water-insoluble organic solvent was used for elution, the water-insoluble organic solvent remaining in the pores and between the adsorbent particles with a water-miscible organic solvent such as methanol or ethanol , away. For this purpose, the water-miscible organic solvent is passed ascending through the absorbent assembly. The amount of water-miscible organic solvent is usually 0.5 to 10 times, more preferably 1 to 5 times the bed volume. The passage of the water-miscible organic solvent is preferably carried out at a specific flow rate (specific load) in the range of 0.5 to 10, in particular 1 to 8 bed volumes per hour

Elution may be followed by another wash step to remove any impurities present. The adsorbent assembly may be operated intermittently and then has one or more, e.g. 2, 3 or 4 in-line, stationary packed with adsorbent fixed beds. It can also be operated continuously and then usually has from 5 to 50 and in particular 15 to 40 adsorbent beds, which are e.g. Part of a "True Moving Bed" arrangement (see K. Tekeuchi J. Chem. Eng. Jpn., 1978, 1 1 pp. 216-220), a "Continuous Circulating Annular" arrangement (see J.P.

Discuss. Farraday Soc. 1949, p. 7) or a simulated moving bed arrangement, as described for example in US Pat. No. 2,985,589 and WO 01/72689 and by G. J. Rossiter et al. Proceedings of AIChE Conference, Los Angeles, CA, Nov. 1991 or H.J. Van Walsem et al., J. Biochtechnol. 1997, 59, p. 127.

The eluent obtained in the elution contains 3,3'-dimethoxy-4,4'-dihydroxystilbene (I), which can be obtained in this way in enriched form.

The eluate obtained during the elution is worked up in the customary manner to obtain the 3,3'-dimethoxy-4,4'-dihydroxystilbene. If the eluate contains acid, it is generally first removed, for example by an aqueous-extractive work-up, or neutralized by the addition of base and the resulting salts are separated off. If necessary, you can before the eluate

concentrate, for example by removing the solvent in a conventional Evaporator assembly. The resulting condensate can be reused, for example, in a subsequent elution.

In this way, a 3,3'-dimethoxy-4,4'-dihydroxystilbene-containing

Crude product which optionally contains other low molecular weight constituents and optionally other constituents of the aqueous composition used, for example guaiacol, vanillin, acetovanillon or lignin.

In a preferred embodiment of the process according to the invention, the 3,3'-dimethoxy-4,4'-dihydroxystilbene-containing eluate or crude product obtained after the desorption or elution is subjected to a further purification step. The purification step may include, for example, fine distillation, crystallization, or liquid chromatographic separation. Preferably, the 3,3'-dimethoxy-4,4'-dihydroxystilbene-containing eluate or crude product is purified by distillation or crystallized.

The invention will be explained in more detail with reference to the examples described below. The examples should not be construed as limiting the invention.

The following abbreviations are used in the following examples: BV stands for bed volume;

VE water stands for demineralised water.

EXAMPLES I) Analysis The determination of the content of 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) and other organic constituents of the aqueous lignin-containing

Compositions were by high performance liquid chromatography (HPLC). The stationary phase used was the column Chromolith® High Resolution RP18e from Merck (length: 100 mm, diameter 4.6 mm). The

Analysis temperature was 25 ° C. Two mobile phases were used: HPLC water with 0.1% by weight of perchloric acid as mobile phase A; Acetonitrile as mobile phase B.

II) Adsorption and desorption of 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) under

Use of activated carbon and ion exchanger resins Example 11.1: Adsorption and desorption of 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) using the Norit® ROY 0.8 activated carbon from Norit

Used activated carbon:

In the experiment, the activated carbon Norit® ROY 0.8 from Norit was used. This activated carbon is a hard coal based extrudate and is made after a

Water vapor activation washed several times with brine (aqueous NaOH). The bulk density of the activated carbon is 400 g / L. The activated carbon has one

Moisture content of max. 5% up.

Used lignin-containing composition:

As the lignin-containing composition, black liquor (thin liquor) from pulp production was used. To try the black liquor with a

Metal filter (filter pore size = 90 microns) filtered. The HPLC analysis of the filtered black liquor gave a content of 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) of 490 mg / kg. Experimental procedure:

A glass column with an internal diameter of 15 mm and a height of 255 mm was constructed and filled with the activated carbon Norit® ROY 0.8 to about 95% degree of filling. The bed volume (BV) was about 43 ml. The activated carbon was washed with about 10 BV of deionized water at a rate of about 5 BV / h in the outflow.

For absorption of the organic components about 12 BV were filtered

Black liquor passed at a rate of about 2 BV / h in the outflow through the column. The column effluent was fractionally collected. The fractions were analyzed for organic components. The achieved loading of 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) was 0.04 mol / L. Thereafter, the activated carbon was washed with about 5 BV of deionized water at a rate of about 2 BV / h in the effluent.

After the washing step, an acid wash was performed to protonate the absorbed 3,3'-dimethoxy-4,4'-dihydroxystilbene (I). For this purpose, about 1 BV 5 percent sulfuric acid was passed at a rate of about 2 BV / h in the effluent through the column. Thereafter, the activated carbon with about 5 BV VE water with a

Speed of about 2 BV / h washed in the effluent. In order to eliminate the water between the activated carbon particles and in the pores therein, after the washing step, about 2 BV of pure methanol was passed through the column at a rate of about 2 BV / h. For desorption of the adsorbed 3,3'-dimethoxy-4,4'-dihydroxystilbene initially about 2 BV of a mixture of methanol and toluene in a mass ratio of 9: 1 were passed at a rate of 2 BV / h in an upward flow through the column. For further desorption was then about 3 BV of pure toluene with a

Speed of 2 BV / h passed in an upward flow through the column. in the

Desorption step, the column effluent was collected in a fraction. This fraction was analyzed for its content of 3,3'-dimethoxy-4,4'-dihydroxystilbene. The achieved degree of desorption of 3,3'-dimethoxy-4,4'-dihydroxystilbene was about 3 to 4%.

After the desorption step, about 1 BV of pure methanol with a

Speed of about 2 BV / h passed in an upward flow through the column. After the methanol wash, the activated carbon was washed with about 10 BV of VE water at a rate of about 5 BV / h in an upflow.

All experimental steps were carried out at room temperature. Example II.2: Adsorption and desorption of 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) using the activated carbon Aquacarb ™ 207C from Chemviron Carbon

Activated carbon used: In the experiment, the activated carbon Aquacarb ™ 207C from Chemviron Carbon was used. This activated carbon is a steam-activated granulated activated carbon based on coconut. The bulk density of the activated carbon is 450 g / L. The activated carbon has a moisture content of max. 10% up. Used lignin-containing composition:

As the lignin-containing composition, black liquor (thin liquor) from pulp production was used. For the experiment, the black liquor was filtered with a metal filter (filter pore size = 90 micrometers). The HPLC analysis of the filtered black liquor gave the following concentrations of the organic components: 457 mg / kg vanillin, 349 mg / kg acetovanillon, 506 mg / kg guaiacol and 308 mg / kg 3,3'-D in et hoxy-4,4 'di hyd roxyst i I n n.

Experimental procedure:

A glass column with an internal diameter of 15 mm and a height of 255 mm was set up and filled with the activated carbon Aquacarb ™ 207C to about 95% degree of filling. The bed volume (BV) was about 43 ml. The activated carbon was first washed with about 10 BV of deionized water at a rate of about 5 BV / h in the outflow.

For adsorption of the organic components about 12 BV were filtered

Black liquor passed at a rate of about 2 BV / h in the outflow through the column. The column outlet was collected fractionally. The fractions were analyzed for organic components. The achieved loading of the individual organic components on the activated carbon was: 0.02 mol / L vanillin, 0.01 mol / L acetovanillon, 0.03 mol / L guaiacol and 0.01 mol / L 3,3'-dimethoxy-4 4'-dihydroxystilbene. Thereafter, the activated carbon was washed with about 5 BV of deionized water at a rate of about 2 BV / h in the effluent.

After the washing step, an acid wash was performed to protonate the adsorbed organic anions. For this purpose, about 1 BV 5 percent sulfuric acid was passed at a rate of about 2 BV / h in the effluent through the column. Thereafter, the activated carbon was washed with about 5 BV of deionized water at a rate of about 2 BV / h in the effluent.

In order to eliminate the water between the activated carbon particles and in the pores therein, after the washing step, about 2 BV of pure methanol was passed through the column at a rate of about 2 BV / h.

For desorption of the adsorbed organic components, initially about 2 BV of a mixture of methanol and toluene in a mass ratio of 1: 1 were passed through the column at a rate of 2 BV / h in an upflow stream. To further

Desorption was then passed approximately 3 BV of pure toluene at a rate of 2 BV / h in an upward flow through the column. In the desorption step was the

Column outlet collected in a fraction. This fraction was analyzed for the content of the organic components. The achieved degree of desorption of the individual organic components was: 89% for vanillin, 95% for acetovanillon, 89% for guaiacol and 8% for 3,3'-dimethoxy-4,4'-dihydroxystilbene.

After the desorption step, about 1 BV of pure methanol with a

Speed of about 2 BV / h passed in an upward flow through the column.

After the methanol wash, the activated carbon was washed with about 10 BV of VE water at a rate of about 5 BV / h in an upflow.

All experimental steps were carried out at room temperature.

Examples II.3 to II.6: Adsorption and Desorption of 3,3'-Dimethoxy-4,4'-dihydroxystilbene (I) Using Various Anion Exchange Resins Used anion exchange resins:

The following anion exchange resins were used:

Used lignin-containing composition:

Metal filter (filter pore size = 90 microns) filtered. The HPLC analysis of the filtered black liquor gave the following concentrations of the organic components: 447 mg / kg vanillin, 268 mg / kg acetovanillon, 460 mg / kg guaiacol and 490 mg / kg 3,3'-D in et hoxy-4,4 '-di hydroxystaline (I).

Experimental procedure:

A glass column having an inner diameter of 15 mm and a height of 255 mm was constructed and filled with the respective Anionentasucher resins to about 90% degree of filling. The bed volume (BV) was about 40 ml. To convert the anion exchange resins into the OH form, these were, with the exception of the anion exchange resin Dowex Monosphere 550A OH, first with a 4 percent NaOH solution and then with about 10 BV of deionized water at a rate of about 5 BV / h washed in the effluent.

For the adsorption of the organic components about 6 BV filtered black liquor were passed at a rate of 2 to 4 BV / h in the effluent through the column. The column outlet was collected fractionally. The fractions were analyzed for organic components. The achieved loading of organic components on the respective anion exchanger resins was for: Dowex Monosphere 550A OH: 0.07 mol / L _H arz,

Amberlite IRA 410 CI: 0.07 mol / L _H arz,

Lewatit lonac SR7: 0.05 mol / L resin,

Lewatit lonac SR6: 0.05 mol / L resin.

Thereafter, the activated carbon was washed with about 5 BV of deionized water at a rate of about 2 BV / h in the effluent.

For desorption of the adsorbed organic components, about 5 BV of a mixture of 5% sulfuric acid, 45% methanol and 50% DI water was passed through the column at a rate of 2 to 4 BV / h. in the

Desorption step, the column effluent was collected in a fraction. This fraction was analyzed for the content of the organic components. The reached

Degree of desaturation of the individual organic components is listed below:

After the desorption step, the activated carbon was washed with about 10 BV of deionized water at a rate of about 2 BV / h in the outflow.

For the regeneration of the anion exchange resin, about 5 BV of a 4 to 10 percent NaOH solution was passed through the column at a rate of about 2 to 4 BV / h in an upflow and then with about 10 BV of VE water

Speed of about 4 BV / h washed in the outflow.

All experimental steps were carried out at room temperature.

III) Odor strip test:

To check the quality and intensity of the odor of 3,3'-dimethoxy-4,4'-dihydroxystilbene or (E) -3,3'-dimethoxy-4,4'-dihydroxystilbene

Odor strip tests performed.

These show that the compound (E) -3,3'-dimethoxy-4,4'-dihydroxystilbene, after storage in the dark as well as after exposure to light, has a sweet (flavored) Odor impression, in particular a typical vanilla-like odor impression that reminds of sweetened milk.

This typical vanilla-like odor impression intensifies significantly when (Ε) -3,3'-dimethoxy-4,4'-dihydroxystilbene is exposed to sunlight. The intensification of the vanilla-like odor impression can not be quantified in the odor laboratory, but can be determined for everyone.

Claims

claims:

1 . Use of the compound 3,3'-dimethoxy-4,4'-dihydroxystilbene (I)

as an odorant.

Use according to claim 1, wherein the compound (I) is an E-isomer

or is present as an E / Z isomer mixture, which contains predominantly the E-isomer (IE).

Use of the compound (I) as defined in any one of claims 1 and 2 for unfolding a vanillin odor under the action of light.

Use according to any one of claims 1 to 3, wherein the compound (I) is part of a composition which additionally contains a carrier material.

Use according to claim 4, wherein the composition is selected from detergents, laundry detergents, cleaners, fragrance-containing hygiene articles, fragrance dispensers and perfumes.

Use according to one of claims 4 and 5, wherein the compound (I) is part of a detergent and / or laundry care product.

A fragrance composition and / or a fragrance material containing the compound (I) as defined in claims 1 to 2 and a carrier material, wherein the fragrance composition and / or the fragrance material contains the compound (I) in an amount corresponding to the fragrance composition and / or gives the fragrance material a smell or alters the odor of the fragrance composition and / or fragrance material.

A method of imparting or changing a smell of a composition, comprising adding to the composition the compound (I) as defined in claims 1 to 2 in an amount which is

Composition gives a smell or the smell of

Composition changed.

9. A process for obtaining 3,3'-dimethoxy-4,4'-dihydroxystilbene (I)

aqueous, alkaline lignin-containing compositions thereby

characterized in that the aqueous, basic ligninhaltige

A composition which has optionally been treated with alkalis or oxidatively treated with a solid adsorbent which separates the adsorbent from the aqueous, alkaline lignin-containing composition and then the adsorbent to obtain the 3,3'-dimethoxy-4,4'-dihydroxystilbene (I) treated with an eluent, taking a 3,3'-

Dimethoxy-4,4'-dihydroxystilbene-containing eluate.

10. The method of claim 9, wherein the eluent is selected from organic solvents.

1 1. A process according to any one of claims 9 or 10, wherein the eluent is selected from C 1 -C 4 alkanols, aromatic hydrocarbons, and mixtures thereof.

12. The method according to any one of claims 9 to 1 1, wherein the 3,3'-dimethoxy-4,4'- dihydroxystilbene-containing eluate is subjected to a further purification step.

13. The method according to any one of claims 9 to 12, wherein the aqueous, alkaline lignin-containing composition is black liquor from the paper industry, pulp or cellulose production.

14. The method according to any one of claims 9 to 13, wherein the solid adsorbent

is selected from crosslinked basic or cationic, organic polymer resins and activated carbon.

15. The method according to any one of claims 9 to 14, wherein the solid adsorbent

is selected under activated carbon.

Form PCT / ISA / 210 (continuation of first sheet (2)) (January} '2015)