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WO2022013278A1 - Procédé de production d'un produit biosourcé, produit correspondant et utilisations - Google Patents

Procédé de production d'un produit biosourcé, produit correspondant et utilisations Download PDF

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Publication number
WO2022013278A1
WO2022013278A1 PCT/EP2021/069583 EP2021069583W WO2022013278A1 WO 2022013278 A1 WO2022013278 A1 WO 2022013278A1 EP 2021069583 W EP2021069583 W EP 2021069583W WO 2022013278 A1 WO2022013278 A1 WO 2022013278A1
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Prior art keywords
fatty alcohol
total mass
weight
decen
alkoxylate
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Ceased
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PCT/EP2021/069583
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German (de)
English (en)
Inventor
Andreas Brakemeier
Vera Gratzl
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Werner and Mertz GmbH
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Werner and Mertz GmbH
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Priority claimed from DE102020119024.7A external-priority patent/DE102020119024A1/de
Application filed by Werner and Mertz GmbH filed Critical Werner and Mertz GmbH
Priority to EP21749121.6A priority Critical patent/EP4182423A1/fr
Publication of WO2022013278A1 publication Critical patent/WO2022013278A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C301/00—Esters of sulfurous acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/02—Preparation of ethers from oxiranes
    • C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/06—Ether- or thioether carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2006—Monohydric alcohols
    • C11D3/2027—Monohydric alcohols unsaturated
    • C11D3/2031—Monohydric alcohols unsaturated fatty or with at least 8 carbon atoms in the alkenyl chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use

Definitions

  • the present invention relates to a method for producing a product comprising one or more bio-based substances selected from the group consisting of fatty alcohols, fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates, fatty alcohol alkoxylate carboxylic acids and their mixtures.
  • the invention also relates to a product which can be produced using a method according to the invention.
  • the invention also relates to the use of a vegetable oil or a fatty acid alkyl ester produced from vegetable oil as a starting material in a process for the production of a product comprising a cross-metathesis reaction.
  • the present invention is in the technical field of surfactants and, as far as products aimed directly at consumers are concerned, in the technical field of detergents, cleaning agents and cosmetic products.
  • the German Patent and Trademark Office has identified the following prior art for the priority application DE 10 2020 119 024.7: DE 199 12 684 A1, EP 1 716 163 B1, WO 02/076920 A1, WO 2003/066567 A1 and
  • bio-based raw materials i.e. raw materials based on plants, animals or microbes
  • surfactants there is a constant need for detergents, cleaning agents and cosmetic products as well as surfactants to be used in them based on sustainable resources.
  • bio-based raw materials i.e. raw materials based on plants, animals or microbes
  • a particularly preferred raw material basis for surfactants and thus for detergents, cleaning agents and cosmetic products that are to be produced and/or consumed in northern latitudes and in particular in Europe are vegetable oils based on plants that are found in precisely these northern latitudes and in particular in Europe be grown in large quantities.
  • the industrially important natural raw materials palm kernel oil and coconut oil are increasingly viewed as problematic by manufacturers and consumers. For this reason, rapeseed, olive and sunflower oil in particular have been used to an increasing extent for the production of surfactants for several years.
  • the average chain length when using rapeseed, olive or sunflower oil is somewhat longer and is in the range of 16-18 in particular carbon atoms. These chain length differences affect the properties of the surfactants produced and thus the cleaning performance that can be achieved. In many cases, the cleaning performance of surfactants based on rapeseed, olive or sunflower oil is not yet found to be optimal.
  • Fatty alcohols and fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates and fatty alcohol alkoxylate carboxylic acids that can be produced from them are surfactant product classes that are manufactured on a large industrial scale worldwide. Fatty alcohols are already predominantly produced from renewable raw materials.
  • fatty alcohol refers to long-chain (from 8 carbon atoms in the chain) aliphatic alcohols that are saturated or unsaturated. To date, however, it has primarily been saturated fatty alcohols (alkanols) that have been used in industry; the chain length is usually in the range of 8-16 carbon atoms.
  • Unsaturated, particularly long-chain fatty alcohols such as oleyl alcohol are produced and sold on a comparatively small scale by individual suppliers.
  • Fatty alcohols are extremely important in the chemical industry. They are used as raw materials for the production of important anionic, nonionic and cationic surfactants.
  • European vegetable oils have so far hardly been used as a basis for the production of fatty alcohols (and their derivatives), because the longer average chain length in the range of 16-18 carbon atoms, as it results from the use of European vegetable oils, leads to product properties that - apart from special products - are perceived as disadvantageous.
  • fatty alcohols are to be used as starting material for the production of fatty alcohol derivatives, in particular for the production of fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates, fatty alcohol alkoxylate carboxylic acids and mixtures thereof
  • fatty alcohols generally have an unpleasant odor of their own (cf. in this respect, for example, the comments in Alkyl polyglycosides, Karlheinz Hill, Wolfgang von Rybinski, Gerhard Stoll, 1996, VCH, page 16). For this reason, residual fatty alcohol levels are common removed from the mixture with its derivatives in order to eliminate odor and other disadvantages.
  • a process for producing a product comprising one or more bio-based, preferably vegetable oil-based substances selected from the group consisting of fatty alcohols, fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol -Alkoxylate sulfates, fatty alcohol alkoxylate carboxylic acids and mixtures thereof, with the following steps:
  • step (S3) To produce a product comprising one or more vegetable oil-based substances selected from the group consisting of fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates, fatty alcohol alkoxylate carboxylic acids and mixtures thereof in step (S3) produced fatty alcohol processed in one step or in several (partial) steps. This applies analogously to the production of other derivatives of the fatty alcohol produced in step (S3).
  • an inventive method for producing a product comprising one or more bio-based, preferably vegetable oil-based substances selected from the group consisting of fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates, fatty alcohol alkoxylate - Carboxylic acids and their mixtures with the following steps:
  • step (S4) Conversion of the fatty alcohol into a fatty alcohol alkoxylate, into a fatty alcohol polyglycoside, into a fatty alcohol sulfate, into a fatty alcohol alkoxylate sulfate or into a fatty alcohol alkoxylate carboxylic acid.
  • the method according to the invention (and its preferred embodiment with step (S4)) is thus based on the use of bio-based oil, preferably vegetable oil, or fatty acid alkyl esters from bio-based oil, preferably vegetable oil; it therefore leads to products comprising bio-based, preferably vegetable oil-based, substances.
  • a first fatty acid alkyl ester is prepared or provided from vegetable oil, whereby according to the invention it is taken into account that this first fatty acid alkyl ester comprises at least one (ie one or more than one) central (ie non-terminal) double bond.
  • the production of fatty acid alkyl esters from vegetable oil has long been known per se and is carried out on an industrial scale, cf. the production of biodiesel (ie fatty acid methyl ester), cf. in particular WO 03/066567 A1.
  • the process according to the invention is particularly suitable for synthesis on an industrial scale, since the starting materials are vegetable oils or fatty acid alkyl esters from vegetable oil, which are available in large quantities.
  • the first fatty acid alkyl ester prepared or provided in step (S1) is used in a step (S2) in a cross-metathesis reaction.
  • the cross-metathesis reaction is carried out in such a way that the first fatty acid alkyl ester and an olefin are reacted in such a way that a second fatty acid alkyl ester results.
  • the implementation of cross-metathesis reactions using a fatty acid alkyl ester and an olefin are already known per se. See “Refining of vegetable oils for chemistry by olefin metathesis", Chikkali, Mecking, Ang. Chemie (2012). In the patent literature see WO 02/076920. See also the activities of the company Elevance, Woodridge, IL, U.S.A.
  • the second fatty acid alkyl ester resulting in step (S2) preferably has a fatty acid chain (typically an unsaturated fatty acid chain) whose chain length is shortened by the cross-metathesis reaction in comparison with the first fatty acid alkyl ester used.
  • a fatty acid chain typically an unsaturated fatty acid chain
  • the second fatty acid alkyl ester is converted into a fatty alcohol of the same chain length in a step (S3).
  • the number of carbon atoms in the fatty alcohol resulting from step (S3) is therefore equal to the number of carbon atoms in the carboxylic acid unit of the second fatty acid alkyl ester, cf. the examples below.
  • the conversion of fatty acid alkyl esters to fatty alcohols is already known, also and in particular for the production of fatty alcohols as a starting material for the production of washing-active substances.
  • step (S3) of the inventive According to the method resulting fatty alcohol is prepared according to the invention from a fatty acid alkyl ester, which in turn is the product of a cross-metathesis reaction.
  • the fatty alcohol produced in step (S3) is therefore produced over several reaction stages from a bio-based oil, preferably vegetable oil, mentioned in step (S1), but has an aliphatic carbon chain (typically an unsaturated carbon chain), as is even the case in the fatty acid alkyl ester is not present, which is produced in step (S1).
  • step (S2) causes the central double bond of the first fatty acid alkyl ester to be cleaved, so that the carbon chain of the fatty acid of the first fatty acid alkyl ester is only incomplete in the fatty alcohol, as is the case in step (S3).
  • Exemplary reaction schemes are detailed below.
  • the fatty alcohol resulting in step (S3) is bio-based, preferably vegetable oil-based; namely, it results as a direct synthetic consequence of vegetable oil or fatty acid alkyl esters from vegetable oil or from corresponding animal oils (including fats) or oils on a microbial basis.
  • Using the radiocarbon method it can be analytically proven that it is not based on fossil, petrochemical materials (petroleum).
  • a product comprising one or more bio-based, preferably vegetable oil-based substances selected from the group consisting of fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates, fatty alcohol alkoxylate carboxylic acids and mixtures thereof preferably the fatty alcohol resulting in step (S3) of the process according to the invention is further reacted in a subsequent step (S4), which can include partial steps (e.g. in the production of fatty alcohol alkoxylate sulfates and fatty alcohol alkoxylate carboxylic acids via the fatty alcohol alkoxylate ).
  • the conversion takes place to an alkoxylate, a polyglycoside, a sulfate, an alkoxylate sulfate (in practice often "ether sulfate”) or an alkoxylate carboxylic acid (in practice often "ether carboxylic acid”) of the fatty alcohol.
  • fatty alcohol alkoxylate (in practice often "fatty alcohol alkoxylate”) includes different compounds with a different number of alkylene oxide units.
  • fatty alcohol alkoxylate refers to and therefore includes - unless otherwise specified in the individual case - all compounds present in a defined mixture (here: the mixture of alkoxylation products of the fatty alcohol used in step (S4)) that have a lipophilic part Fatty alcohol and at least one alkylene oxide unit (as hydrophilic part).
  • the total amount of "fatty alcohol alkoxylate” in such a mixture thus includes the amounts of all individual species, each on its own considered to be fatty alcohol alkoxylate.
  • fatty alcohol ethoxylates are particularly relevant; every general reference to fatty alcohol alkoxylate given in the present text therefore always includes a specific reference to fatty alcohol ethoxylate in individual cases, even without express reference; the above statements on the understanding of the term apply accordingly.
  • Fatty alcohol propoxylates and fatty alcohol butoxylates are also relevant; reference is made to the statements below.
  • 9-decen-1-ol ethoxylate thus specifically encompasses all ethoxylates present in a mixture of the fatty alcohol 9-decen-1-ol which has been subjected to an ethoxylation reaction, regardless of the number of ethylene oxide units contained in an individual compound.
  • fatty alcohol polyglycosides designates reaction products of the fatty alcohol used in step (S4), namely polyglycosides formed by reaction of the fatty alcohol used.
  • the term includes in particular alkyl polyglycosides and alkenyl polyglycosides.
  • a fatty alcohol polyglycoside typically includes various individual compounds with 1, 2, 3, 4 or more saccharide units.
  • fatty alcohol sulfate in connection with step (S4) denotes a reaction product of the fatty alcohol resulting in step (S3), namely a sulfate obtained by reaction.
  • a sulfate is used, for example, in the reaction of the fatty alcohol Sulfur trioxide (or other sulfation agent) and subsequent neutralization with caustic.
  • the reaction of a fatty alcohol with sulfur trioxide to hydrogen sulfate (or sulfuric acid ester) and the subsequent neutralization with lye are already known per se; according to the invention, however, specific fatty alcohols are used.
  • fatty alcohol alkoxylate sulfate (in practice often abbreviated to "fatty alcohol ether sulfate”) in connection with step (S4) denotes a reaction product of the fatty alcohol resulting in step (S3), namely an alkoxylate obtained by reaction (typically in two partial steps).
  • -Sulfate Such an alkoxylate sulphate is obtained, for example, by producing a fatty alcohol alkoxylate in a manner known per se starting from the fatty alcohol in a first step and then reacting this fatty alcohol alkoxylate with sulfur trioxide (or another sulphating agent) in a second step. converted to hydrogen sulfate (or sulfuric acid ester) and then neutralized with lye.
  • the preparation of fatty alcohol alkoxylate sulfates from a fatty alcohol in several steps is already known per se; according to the invention, however, specific fatty alcohols are used.
  • fatty alcohol alkoxylate carboxylic acids in connection with step (S4) denotes a reaction product of the fatty alcohol resulting in step (S3), namely an alkoxylate carboxylic acid obtained by reaction (typically in two partial steps).
  • the terms “fatty alcohol alkoxylate carboxylic acid” or “fatty alcohol ether carboxylic acid” or “ether carboxylic acid” denote the identical compounds and, unless otherwise specified in individual cases, each include the protonated form (carboxylic acid group is present) and the deprotonated form (carboxylate group is present; eg salts of carboxylic acid) of the molecule.
  • Such a fatty alcohol alkoxylate carboxylic acid is obtained, for example, by preparing a fatty alcohol alkoxylate in a manner known per se in a first step starting from the fatty alcohol, then in a second step this fatty alcohol alkoxylate with an alkyl carboxylic acid which is attached to a carbon atom their alkyl chain is halogenated, reacted and then optionally neutralized.
  • a fatty alcohol alkoxylate is produced in a first sub-step starting from the fatty alcohol in a manner known per se, then in a second sub-step this fatty alcohol alkoxylate is mixed with sodium chloroacetate (or monochloroacetic acid) to form the fatty alcohol alkoxylate acetate (i.e. for Sodium salt of fatty alcohol alkoxylate carboxylic acid, ie a "fatty alcohol alkoxylate carboxylic acid" within the meaning of the above definition); if necessary, will then eg neutralized with sulfuric acid (the resulting protonated product (comprising a carboxylic acid group) is also a "fatty alcohol alkoxylate carboxylic acid").
  • sodium chloroacetate or monochloroacetic acid
  • fatty alcohol alkoxylate carboxylic acids from a fatty alcohol in several steps is already known per se; according to the invention, however, specific fatty alcohols are used.
  • sodium chloroacetate i.e. 2-chloroethanoic acid
  • 3-chloropropanoic acid is preferably used in the process of the invention for converting the fatty alcohol alkoxylate to the fatty alcohol alkoxylate carboxylic acid, sodium chloroacetate being particularly preferably used.
  • the use of longer-chain, terminally chlorinated carboxylic acids is preferred only in a few exceptional cases.
  • fatty alcohols For the production of fatty alcohols, fatty alcohol sulfates, fatty alcohol alkoxylates and fatty alcohol alkoxylate sulfates, see, for example, Günter Wagner, Waschsch, 5th edition, 2017, Wiley-VCH, pages 344 to 346.
  • fatty alcohol alkoxylate For carboxylic acids see, for example, US Pat. No. 3,992,443 A.
  • the products resulting from step (S4) are bio-based, preferably vegetable oil-based; they result in a direct synthetic sequence from vegetable oil or fatty acid alkyl esters from vegetable oil or from corresponding animal oils (including fats) or oils on a microbial basis.
  • Using the radiocarbon method it can be analytically proven that they are not based on fossil materials (such as petroleum in particular).
  • the fatty alcohols, fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates, fatty alcohol alkoxylate carboxylic acids and mixtures thereof produced as a preferably vegetable oil-based reaction product of the method according to the invention have a lipophilic carbon chain that is often shorter than that Carbon chain of the fatty acids in the underlying vegetable oil or in the first fatty acid alkyl ester used as starting material in step (S1).
  • step (S1) The exact extent of a chain shortening and the final chain lengths as well as the precise structure of the lipophilic residues results from the specific selection of the first fatty acid alkyl ester (starting material according to step (S1)), the olefin used in step (S2) and the others Reaction conditions in step (S2) and (S3) and optionally step (S4).
  • the resulting fatty alcohols, fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol hol sulfates, fatty alcohol alkoxylate sulfates or fatty alcohol alkoxylate carboxylic acids can be used in an excellent manner as intermediates for the production of surfactants or directly as surfactants, especially for use in Detergents, cleaning products and cosmetic products.
  • the process according to the invention offers flexible access to surfactants with specific properties which can be customized and adapted to the requirements of the individual case through the choice of starting materials and reaction conditions.
  • the fatty alcohols resulting in step (S3) are chemically central, preferably vegetable oil-based intermediates, which themselves already have surfactant properties; they can therefore either be further processed (to form surfactants such as fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates, fatty alcohol alkoxylate carboxylic acids or to form other substances, in particular other nonionic, anionic, cationic or amphoteric surfactants or other substances) or used directly, for example in detergents, cleaning agents and cosmetic products.
  • surfactants such as fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates, fatty alcohol alkoxylate carboxylic acids or to form other substances, in particular other nonionic, anionic, cationic or amphoteric surfactants or other substances
  • step (S2) The by-products obtained in the cross-metathesis reaction in step (S2) from the reaction of the first fatty acid alkyl ester and the olefin are also valuable substances which can be put to further use.
  • the product of the manufacturing process according to the invention is a bio-based product, preferably based on vegetable oil, which - depending also on the type of cleaning measures carried out - consists of individual substances (specific fatty alcohols, specific fatty alcohol alkoxylates, specific fatty alcohol polyglycosides, specific fatty alcohol sulphates, specific fatty alcohol alkoxylate sulfates, specific fatty alcohol alkoxylate carboxylic acids) or mixtures.
  • the mixtures are mixtures comprising one or more specific fatty alcohols, mixtures comprising one or more specific fatty alcohol alkoxylates, mixtures comprising one or more specific fatty alcohol polyglycosides, mixtures comprising one or more specific fatty alcohol sulfates, mixtures comprising one or more specific fatty alcohol alkoxylate sulfates and mixtures comprising one or more specific fatty alcohol alkoxylate carboxylic acids.
  • the process according to the invention can also lead to mixtures in which several of the specific (individual) substances mentioned are present side by side, for example (a) fatty alcohols and fatty alcohol alkoxylates, (b) fatty alcohols and fatty alcohol polyglycosides, (c) fatty alcohols and fatty alcohol sulfates, (d) fatty alcohol alkoxylates and fatty alcohol alkoxylate sulfates, (e) fatty alcohol alkoxylates and fatty alcohol polyglycosides, (f) fatty alcohol alkoxylates and fatty alcohol alkoxylate carboxylic acids, etc.
  • such mixtures include other surfactants, which are preferably likewise bio-based, preferably vegetable oil-based. “Vegetable oil-based” also means that the substance described in this way is produced or can be produced as a direct synthetic sequence from vegetable oil or fatty acid alkyl esters from vegetable oil.
  • the products manufactured using the method according to the invention are particularly suitable as intermediates and components in the manufacture of detergents, cleaning agents and cosmetic products.
  • the invention thus also relates to a method as defined above and in the claims, wherein the fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates or fatty alcohol alkoxylates resulting in step (S4) Carboxylic acids are fed to further processing, the further processing leading to a product which is selected from the group consisting of detergents, cleaning agents and cosmetic products.
  • the product of the production process according to the invention is preferably selected from the group consisting of detergents, cleaning agents and cosmetic products.
  • the method according to the invention is therefore a method for producing a detergent, cleaning agent or cosmetic product.
  • This preferred method according to the invention comprises steps (S1), (S2), (S3) and preferably (S4) (as defined above, preferably as described above as preferred) and in many cases further steps (as they are, for example, in the manufacturing of detergents, cleaning agents and cosmetic products).
  • the method according to the invention is preferably designed in such a way that the first fatty acid alkyl ester (which is relevant for the further steps of the method according to the invention) after production or provision in step (S1) is initially present as a component of a mixture that contains further fatty acid alkyl esters from bio-based oil, preferably vegetable oil, and is preferably present as a component of a mixture that contains fatty acid alkyl esters in a mixing ratio that corresponds to the fatty acid pattern of the bio-based oil used (preferably vegetable oil).
  • This preferred embodiment is realized, for example, by technical processes in which plant triglycerides are subjected to transesterification in the customary manner.
  • Fatty acid alkyl esters are typically obtained as a result of such transesterification, wherein each specific fatty acid alkyl ester (as an individual compound) is contained in a proportion or mixing ratio that corresponds to the fatty acid profile of the vegetable oil (or other bio-based oil) used.
  • the first fatty acid alkyl ester is preferably separated in an intermediate step (pre-S2) from such further fatty acid alkyl esters (which are not to be further processed in the method according to the invention), so that the first fatty acid alkyl ester is used in step (S2) in purified form will.
  • pre-S2 intermediate step
  • oleic acid alkyl ester e.g.
  • oleic acid methyl ester or oleic acid ethyl ester can be prepared or provided in step (S1) and separated in step (pre-S2) from other fatty acid alkyl esters which, after the transesterification of the (vegetable oil) triglycerides together were obtained with the oleic acid alkyl ester.
  • step (S2) It is advantageous to use the first fatty acid alkyl ester in purified form in step (S2), because this reduces the number of side reactions in steps (S2), (S3) and (if it is carried out) (S4) and the number of product compounds (Target products and by-products) limited after step (S4).
  • step (pre-S2) it is technically advantageous or desirable for other reasons to obtain a product mixture after step (S3) or (S4) which comprises a large number of individual compounds with different fatty acid residues. In this way, for example, a surfactant mixture with a very broad spectrum of activity can be achieved. In these cases, step (pre-S2) can be omitted.
  • a first fatty acid alkyl ester which comprises at least one central double bond is used in step (S1).
  • This first fatty acid alkyl ester is preferably an oleic acid alkyl ester, preferably a methyl ester, ethyl ester, propyl ester or butyl ester of oleic acid.
  • Oleic acid i.e. (9Z)-octadec-9-enoic acid (also referred to as c/s-9-octadecenoic acid or as oleic acid) has a single double bond in position 9. This double bond makes the oleic acid alkyl ester (as the first fatty acid alkyl ester) undergo a cross-metathesis reaction accessible, as is carried out in step (S2) of the method according to the invention.
  • a first fatty acid alkyl ester is preferably produced from a bio-based oil or a first fatty acid alkyl ester from provided a bio-based oil, wherein each bio-based oil comprises a vegetable oil or (more preferably) is a vegetable oil.
  • Such a vegetable oil comprises an oil from one plant or several plants or is an oil from one plant or several plants, which is/are preferably selected from the group consisting of cotton, hemp, hazelnut, thistle, peanut, jojoba, camelina , Flaxseed, Almond, Poppy, Olive, Fodder Radish, Rocket, Pecan, Pistachio, Canola, Rice, Rapeseed, Safflower, Mustard, Sunflower, Soy and Walnut. All of the plants mentioned produce a vegetable oil that has a high proportion of oleic acid chemically bound in triglycerides.
  • the vegetable oil comprises an oil from one or more plants or is an oil from one or more plants selected from the group consisting of
  • Sunflower oil preferably high oleic sunflower oil, preferably with a proportion of oleic acid in the triglycerides of the sunflower oil of greater than 85% by weight, - rapeseed oil, preferably 00 rapeseed oil, preferably with a proportion of oleic acid in the sunflower oil of greater than 85% by weight, - rapeseed oil, preferably 00 rapeseed oil, preferably with a proportion of oleic acid in the
  • Triglycerides of rapeseed oil greater than 51% by weight
  • Olive oil preferably with a proportion of oleic acid in the triglycerides of the olive oil of more than 55% by weight, the percentages being based on the total mass of free fatty acids after cleavage of the triglycerides.
  • the olefin which is used in step (S2) preferably has 2 to 6 carbon atoms and is preferably ethene, propene, 1-butene or 2-butene
  • ethene preferably ethene, propene, 1-butene or 2-butene
  • 1-decene which is particularly valuable for use as a solvent
  • 1-decene which is often desired as an intermediate and is used in step (S3 ) preferably provided 9-decenoic acid alkyl ester.
  • a process according to the invention is preferred, in which the second fatty acid alkyl ester formed in step (S2) and used in step (S3) contains a double bond and is preferably an alkyl ester of 9-decenoic acid, 9-undecenoic acid or 9-dodecenoic acid or a mixture of several such alkyl esters, preferably a methyl ester, ethyl ester, propyl ester or butyl ester of 9-decenoic acid, 9-undecenoic acid or 9-dodecenoic acid, particularly preferably a methyl ester, ethyl ester or butyl ester of 9-decenoic acid, very particularly preferably the methyl ester of 9-decenoic acid (9- LADY).
  • a process according to the invention is preferred, wherein the second fatty acid alkyl ester reacted in step (S3) contains a double bond in position 9 and is preferably an alkyl ester of 9-decenoic acid, 9-undecenoic acid or 9-dodecenoic acid or a mixture of several such alkyl esters, and in admixture with further fatty acid alkyl esters which do not have a double bond in the 9-position, the proportion of fatty acid alkyl esters with a double bond in the 9-position being at least 90% by weight, preferably at least 93% by weight, particularly preferably, of the total mass of fatty acid alkyl esters at the start of the reaction at least 95% by weight, very particularly preferably at least 98% by weight, preferably at least 99% by weight and/or the fatty alcohol resulting in step (S3) contains a double bond in position 9 and preferably 9-decen-1-ol , 9-undecen-1-ol or 9-do
  • the second fatty acid alkyl ester which is preferably a product of the cross-metathesis reaction of oleic acid alkyl ester, always contains a double bond if it is not present in the cross-metathesis reaction of step (S2). a (usually undesired) reduction of the double bond of the first fatty acid methyl ester occurs.
  • the person skilled in the art will therefore preferably avoid (undesirable) reducing conditions.
  • step (S2) it is also preferred if a catalyst is used in step (S2) to catalyze the cross-metathesis reaction, in the presence of which isomerization of the double bond is suppressed at least as completely as possible.
  • a catalyst is used in step (S2) to catalyze the cross-metathesis reaction, in the presence of which isomerization of the double bond is suppressed at least as completely as possible.
  • the person skilled in the art will orientate himself on the basis of customary experiments and select the process which is suitable on an industrial scale.
  • undesired isomers preferably undesired isomers with a double bond in a position other than position 9 of the second fatty acid alkyl ester formed in step (S2), can be separated off in a purification step, preferably before converting the second fatty acid alkyl ester to a fatty alcohol of the same chain length in step (S3) takes place.
  • Alkyl esters of 9-decenoic acid result from the reaction of the oleic acid alkyl ester with ethene, propene and 1-butene, with the use of propene and 1-butene as further alkyl esters of the 9-undecenoic acid alkyl ester (when using propene) or 9-dodecenoic acid - Kylester (when using 1-butene) result.
  • the second fatty acid alkyl ester is preferably reduced to a saturated or monounsaturated fatty alcohol of the same carbon chain length, but preferably selectively while retaining a double bond, preferably a double bond in position 9 of the carbon chain.
  • the reaction in step (S3) thus usually includes a reduction reaction.
  • the second fatty acid alkyl ester (preferably containing a double bond) is reduced either to a saturated fatty alcohol or, preferably, to a monounsaturated fatty alcohol (whose double bond is preferably in the 9-position).
  • the person skilled in the art chooses the conditions of the reduction reactions in such a way that he achieves the product he is aiming for.
  • a double bond is to be retained (e.g. the double bond in position 9, as in the above-mentioned alkyl esters of 9-decenoic acid, 9-undecenoic acid or 9-dodecenoic acid)
  • conditions of a selective reduction are chosen in which only or predominantly the ester function of the second fatty acid alkyl ester is converted into an alcohol group, but the double bond is wholly or predominantly retained.
  • the person skilled in the art will choose the reduction conditions in such a way that a terminal double bond is retained. This applies in particular to the preparation of the preferred fatty alcohol 9-decen-1-ol and very particularly to the preparation of 9- Decen-1-ol from 9-DAME.
  • the fatty alcohol resulting in step (S3) is preferably 9-decen-1-ol, 9-undecen-1-ol or 9-dodecen-1-ol.
  • the fatty alcohol 9- decen-1-ol dec-9-en-1-ol; CAS No. 13019-22-2, in practice often simplified 9- called decenol).
  • This compound is a well-known fragrance with a rose note; for fragrance properties see Surburg, Panten, Common Fragrance and Flavor Materials, Wiley-VCH, 5th edition 2006, pages 10-11 and http://www.thegodscentscompany.com/data/rw1009352.html (as accessed on June 16 2020) with the references given there. So far, this compound has not been made from vegetable oil or other bio-based oils. It is a particular achievement of the present invention to provide a new synthetic approach to this compound that can be carried out on an industrial scale and is sustainable. This makes 9-decen-1-ol a key synthetic chemical compound that offers access to other vegetable oil-based surfactants on an industrial scale (in particular when carrying out the preferred step (S4).
  • step (S4) which—as already indicated above—is carried out in preferred embodiments of the method according to the invention. Alkoxylates, polyglycosides, sulfates, alkoxylate sulfates or alkoxylate carboxylic acids of the fatty alcohol resulting in step (S3) are produced.
  • alkoxylate sulfates (“ether sulfates”) of the fatty alcohol resulting in step (S3) are produced, these are referred to here as fatty alcohol alkoxylate sulfates.
  • ether sulfates alkoxylate sulfates
  • fatty alcohol alkoxylate sulfates starting from the fatty alcohol (product of step (S3)), this is usually done in a first sub-step Formed fatty alcohol alkoxylate and from this in a second sub-step the fatty alcohol alkoxylate sulfate.
  • alkoxylate carboxylic acids of the fatty alcohol resulting in step (S3) are produced.
  • the fatty alcohol alkoxylate is usually formed in a first step and the fatty alcohol alkoxylate carboxylic acid from this in a second step.
  • isomerizations and derivatizations during step (S4) and its possible partial steps are not preferred in each case, they are not generally ruled out either.
  • the fatty alcohol 9-decen-1-ol, 9-undecen-1-ol or 9-dodecen-1-ol resulting in step (S3) becomes an alkoxylate or a polyglycoside or a sulfate or converted to an alkoxylate sulfate or to an alkoxylate carboxylic acid of these alcohols in such a way that the respective double bond (in position 9) is retained, preferably without isomerization.
  • step (S4) it is preferred to start in step (S4) from the fatty alcohol 9-decen-1-ol (which is preferred in the context of the present invention) and not completely convert this to the corresponding fatty alcohol alkoxylate, to the corresponding fatty alcohol polyglycoside , to the fatty alcohol sulfate, to the fatty alcohol alkoxylate sulfate or to the corresponding fatty alcohol alkoxylate carboxylic acid.
  • a product mixture results which, in addition to the reaction product fatty alcohol alkoxylate, fatty alcohol polyglycoside, fatty alcohol sulfate, fatty alcohol alkoxylate sulfate or fatty alcohol alkoxylate carboxylic acid, also contains a proportion of 9- decen-1-ol.
  • This product mixture is particularly preferred and combines both excellent surfactant properties and an advantageous odor (caused or at least significantly influenced by 9-decen-1-ol).
  • 9-decen-1-ol itself also has the properties of a nonionic surfactant.
  • the fatty alcohol resulting in step (S3) is 9-decen-1-ol and in step (S4) this 9-decen-1-ol is not completely converted into a fatty alcohol alkoxylate, into a fatty alcohol polyglycoside, to a fatty alcohol sulfate, to a fatty alcohol alkoxylate sulfate or to a fatty alcohol alkoxylate carboxylic acid, so that a product mixture results which includes a proportion of 9-decen-1-ol.
  • the fatty alcohol preferably 9-decen-1-ol, 9-undecen-1-ol and/or 9-dodecen-1-ol, (in whole or in part) with (preferably bio-based ) ethylene oxide and/or propylene oxide and/or Butylene oxide reacted that corresponding fatty alcohol alkoxylates result (in some preferred cases in a mixture with unused fatty alcohol, especially 9- decen-1-ol, see above).
  • the fatty alcohol preferably 9-decen-1-ol, 9-undecen-1-ol and/or 9-dodecen-1-ol, (in whole or in part) with (preferably bio-based ) ethylene oxide and/or propylene oxide and/or Butylene oxide reacted that corresponding fatty alcohol alkoxylates result (in some preferred cases in a mixture with unused fatty alcohol, especially 9- decen-1-ol, see above).
  • the production of fatty alcohol ethoxylates is particularly relevant; the fatty alcohol used, preferably 9-decen-1-ol, 9-undecen-1-ol and/or 9-dodecen-1-ol, is typically reacted with (preferably bio-based) ethylene oxide in practice. Corresponding fatty alcohol propoxylates and fatty alcohol butoxylates are also relevant.
  • the fatty alcohol alkoxylate resulting in step (S4) of a process according to the invention preferably the alkoxylate of 9-decen-1-ol, 9-undecen-1-ol or 9-dodecen-1-ol, comprises an average of 2 to 25 in the hydrophilic residue Alkylene oxide units, preferably 3 to 12 alkylene oxide units, particularly preferably 3 to 8 alkylene oxide units.
  • the fatty alcohol alkoxylate resulting in step (S4) preferably the alkoxylate of 9-decen-1-ol, 9-undecen-1-ol or 9-dodecen-1-ol, preferably has an HLB per se value in the range from 7 to 18, preferably 8 to 16, particularly preferably 9 to 15, determined according to the Griffin method (WC Griffin: Classification of surface active agents by HLB. In J. Soc. Cosmet. Chem. 1,
  • the fatty alcohol alkoxylate resulting from step (S4) preferably the alkoxylate of 9-decen-1-ol, 9-undecen-1-ol or 9-dodecen- 1 -ol, (i) not end-capped or (ii) end-capped in a further step.
  • the resulting fatty alcohol alkoxylate is preferably not end-capped.
  • the person skilled in the art will etherify the resulting fatty alcohol alkoxylate with an alcohol and thus close the end group in particular if he is aiming for a particularly low-foaming surfactant, as is necessary in specific applications. In particular, when the foaming parameters are not particularly important, end group closure is not required.
  • the fatty alcohol preferably 9-decen-1-ol, 9-undecen-1-ol and/or 9-dodecen-1-ol
  • the fatty alcohol polyglucoside ie the product of Reaction of the fatty alcohol with glucose, oligomers of glucose
  • the fatty alcohol used in step (S4) is preferably saturated or monounsaturated.
  • An alkyl polyglucoside (APG) or an alkenyl polyglucoside then results, as is similarly disclosed in EP 1716163 B1, for example.
  • saturated (less preferred) and monounsaturated (preferred) fatty alcohols reference is made to the above statements.
  • step (S4) it is also preferred in a process according to the invention in step (S4) to convert the fatty alcohol, preferably 9-decen-1-ol, 9-undecen-1-ol and/or 9-dodecen-1-ol, to the fatty alcohol pentoside ( ie the product of the reaction of the fatty alcohol with a pentose), the fatty alcohol used in step (S4) preferably being saturated or monounsaturated.
  • alkyl polypentosides like those already known, compare the products from Wheatoleo and the publications from ARD; Biobased Surfactants: Synthesis, Properties, and Applications, Douglas G. Hayes, Daniel K. Solaiman, Richard D. Ashby, Elsevier, 2019, page 371) or the corresponding alkenyl polypentosides.
  • the fatty alcohol polyglycoside resulting in step (S4) preferably fatty alcohol polyglucoside or polypentoside, preferably from 9-decen-1-ol, 9-undecen-1-ol and/or 9-dodecen- 1-ol, comprises an average of 1 to 5 saccharide units in the hydrophilic radical, preferably 1 to 3 saccharide units, particularly preferably 1 to 2 saccharide units and/or the fatty alcohol polyglycoside resulting in step (S4), preferably fatty alcohol polyglucoside, preferably of 9-decen-1-ol, 9-undecen-1-ol and/or 9-dodecen-1-ol, considered one per se HLB value in the range of 10 to 17, preferably 10 to 16, more preferably 10 to 14.5, determined according to the Griffin method.
  • step (S4) leads in step (S4) to the production of an alkoxylate, a polyglycoside, a sulfate, an alkoxylate sulfate or an alkoxylate carboxylic acid of the fatty alcohol.
  • step (S4) the production of a polyglycoside of the fatty alcohol, the production of a polyglucoside (alkylpolyglucoside, alkenylpolyglucoside) or polypentoside is preferred.
  • a method according to the invention is preferred, in which the product is a mixture comprising one or more fatty alcohol alkoxylates or a mixture comprising one or more fatty alcohol polyglycosides or a mixture comprising one or more fatty alcohol sulfates or a mixture comprising one or more fatty alcohol alkoxylates - Sulfates or a mixture comprising one or more fatty alcohol alkoxylate carboxylic acids, with the following steps:
  • step (S4) Mixing the fatty alcohol alkoxylate, fatty alcohol polyglycoside, fatty alcohol sulfate, fatty alcohol alkoxylate sulfate or the fatty alcohol alkoxylate carboxylic acid resulting in step (S4) resulting in step (S4) with the further surfactant or the further surfactant blend.
  • the bio-based oil, preferably vegetable oil, used in step (S5) and the bio-based oil, preferably vegetable oil, used in step (S1) are different or identical, ie preferably oils from the same plant or different plants, preferably the same plant.
  • the process product is a mixture which, in addition to fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates or fatty alcohol alkoxylate carboxylic acids, also contains another surfactant or another surfactant mixture includes.
  • This further surfactant or the further surfactant mixture is also based on a bio-based oil, preferably vegetable oil, so that the mixture that results overall comprises a considerable number of (different) surfactants, each of which is bio-based (preferably based on vegetable oil).
  • bio-based oil preferably vegetable oil
  • the invention makes surfactant mixtures, detergents, cleaning agents and cosmetic products accessible in a new synthetic way, starting from bio-based oils, preferably vegetable oils.
  • the surfactant compounds resulting in step (S3) or (S4) have special properties that the person skilled in the art uses when designing detergents, cleaning agents and cosmetic products is taken into account in a targeted manner.
  • the product preferably selected from the group consisting of surfactant mixtures, detergents, cleaning agents and cosmetic products
  • the proportion of the fatty alcohol alkoxylate resulting in step (S4) in the total mass of the fatty alcohol alkoxylates contained in the product is at least 10% by weight, preferably at least 20% by weight, 50% by weight, 80% by weight, 90% by weight or 99% by weight and/or one or more fatty alcohol polyglycosides, wherein the proportion of in step
  • (S4) resulting fatty alcohol polyglycoside of the total mass of the polyglycosides contained in the product is at least 10% by weight, preferably at least 20% by weight, 50% by weight, 80% by weight, 90% by weight or 99% Wt Fatty alcohol sulfates is at least 10% by weight, preferably at least 20% by weight, 50% by weight, 80% by weight, 90% by weight or 99% by weight and/or one or more fatty alcohol alkoxylate includes sulfates, the proportion of the fatty alcohol alkoxylate sulfate resulting in step (S4) in the total mass of the fatty alcohol alkoxylate sulfates contained in the product being at least 10% by weight, preferably at least 20% by weight, 50% by weight.
  • the proportion of the in step (S4) resulting fatty alcohol alkoxylate carboxylic acid in the Total mass of the fatty alcohol alkoxylate carboxylic acids contained in the product is at least 10% by weight, preferably at least 20% by weight, 50% by weight, 80% by weight, 90% by weight or 99% by weight.
  • step (a) in step (S4) the fatty alcohol, preferably 9-decen-1-ol (with regard to the advantageous fragrance properties, see above), is not fully implemented, so that a proportion of the fatty alcohol used is mixed with the resulting fatty alcohol alkoxylate , Fatty alcohol polyglycoside, fatty alcohol sulfate, fatty alcohol alkoxylate sulfate or the resulting fatty alcohol alkoxylate carboxylic acid remains, with preferably a proportion of the fatty alcohol used in step (S4) not being separated from the fatty alcohol alkoxylate produced at a later point in time in the process , Fatty alcohol polyglycoside, fatty alcohol sulfate, fatty alcohol alkoxylate sulfate or is separated from the produced fatty alcohol alkoxylate carboxylic acid and/or
  • a product results comprising - one or more vegetable oil-based fatty alcohols selected from the group consisting of 9-decen-1-ol, 9-undecen-1-ol and 9-dodecen-1-ol, preferably comprising at least 9-decen-1-ol, and - a or several vegetable oil-based substances selected from the group consisting of alkoxylates of 9-decen-1-ol, 9-undecen-1-ol and 9-dodecen-1-ol, polyglycosides of 9-decen-1-ol, 9-undecen- 1-ol and 9-dodecen-1-ol, sulfates of 9-decen-1-ol, 9-undecen-1-ol and 9-dodecen-1-ol, alkoxylate sulfates of 9-decen-1- ol, 9-undecen-1-ol and 9-dodecen-1-o
  • Customary industrially produced fatty alcohols have an odor that is perceived as unpleasant.
  • the fatty alcohols 9-decen-1-ol, 9-undecen-1-ol and 9-dodecen-1-ol which are preferred according to the invention do not smell unpleasantly, 9-decen-1-ol is even already known as a fragrance with a rose note. While according to the state of the art-particularly in the production of alkyl polyglycosides-particular importance is attached to the fact that residual amounts of fatty alcohol are largely removed, this technically complex procedure is not necessary within the scope of the invention and (as explained above) not even preferred.
  • the invention also relates to new products which can be produced or are produced using a method according to the invention.
  • a product which can be produced according to a method according to the invention as defined above (preferably in an embodiment designated as preferred), comprising or consisting of one or more bio-based, preferably vegetable oil-based substances selected from the group consisting of 9-decene-1- ol, 9-undecen-1-ol, 9-dodecen-1-ol, their respective alkoxylates, their respective polyglycosides, their respective sulfates, their respective alkoxylate sulfates and their respective alkoxylate carboxylic acids.
  • the respective bio-based, preferably vegetable oil-based fatty alcohols 9-decen-1-ol, 9-undecen-1-ol and 9-dodecen-1-ol and consequently also the fatty alcohol alkoxylates (With an unsaturated carbon chain) and the alkenyl polyglycosides (especially the alkenyl polyglucosides), fatty alcohol sulfates, fatty alcohol alkoxylate sulfates and fatty alcohol alkoxylate carboxylic acids (each with an unsaturated carbon chain), as in the reaction that preserves the double bond of (vegetable oil-based) 9-decen-1-ol, 9-undecen-1-ol and 9-dodecen-1-ol in step (S4) of the preferred method according to the invention are not known to date.
  • bio-based, preferably vegetable oil-based compounds according to the invention ie products of the method according to the invention consisting of the corresponding compound
  • the corresponding (previously unknown) products according to the invention such as mixtures and preparations
  • these new bio-based, preferably vegetable oil-based compounds, in particular detergents, Cleaning and cosmetic products comprising one or more of these compounds are a particular aspect of the present invention.
  • the disclosed compound is based on petrochemical raw materials according to expert understanding and can thus be distinguished from the new vegetable oil-based compounds using the radiocarbon method.
  • the fatty alcohol alkoxylates mentioned (with an unsaturated carbon chain), alkenyl polyglycosides (in particular the alkenyl polyglucosides), fatty alcohol sulfates, fatty alcohol alkoxylate sulfates and fatty alcohol alkoxylate carboxylic acids (each with an unsaturated carbon chain) have excellent surfactants -Properties that are superior in some respects to those of common fatty alcohol alkoxylates, alkyl (poly)glycosides, alcohol sulfates, alcohol alkoxylate sulfates and alcohol alkoxylate carboxylic acids.
  • the compounds mentioned are excellent intermediates on the synthetic route to further processed surfactants.
  • the double bonds contained in the compounds mentioned enable a targeted derivatization in a special way.
  • a product according to the invention (as defined above) is preferred, comprising or consisting of two or more than two bio-based substances wherein at least one of the bio-based substances is selected from the group consisting of the respective alkoxylates, the respective polyglycosides, the respective sulfates, the respective alkoxylate sulfates and the respective fatty alcohol alkoxylate carboxylic acids of 9-decen-1-ol, 9 -Undecen-1-ol and 9-dodecen-1-ol and wherein at least one of the bio-based substances is selected from the group consisting of 9-decen-1-ol, 9-undecen-1-ol, 9-dodecen-1- ol and preferably 9-decen-1-ol.
  • a product according to the invention (as defined above) is preferred, wherein the proportion of the total mass of the bio-based substances selected from the group consisting of 9-decen-1-ol, 9-undecen-1-ol, 9-dodecen-1-ol at the combined total mass of the total mass of the bio-based substances selected from the group consisting of the respective alkoxylates, the respective polyglycosides, the respective sulfates, the respective alkoxylate sulfates and the respective fatty alcohol alkoxylate carboxylic acids of 9-decen-1-ol, 9 -Undecen-1-ol and 9-dodecen-1-ol and the total mass of bio-based substances selected from the group consisting of 9-decen-1-ol, 9-undecen-1-ol, 9-dodecen-1-ol im In the range from 1% to 25% by weight, preferably in the range from 2% to 20% by weight, preferably in the range from
  • a product according to the invention (as defined above) is preferred, comprising one or more bio-based, preferably vegetable oil-based substances selected from the group consisting of
  • Alkoxylate carboxylic acids of 9-decen-1-ol, 9-undecen-1-ol and 9-dodecen-1-ol preferably comprising at least one or more substances selected from the group consisting of alkoxylates, polyglycosides, sulfates, alkoxylate sulfates and alkoxylate carboxylic acids of 9-decen-1-ol and additionally one or more bio-based, preferably vegetable oil-based fatty alcohols selected from the group consisting of 9-decen-1-ol, 9-undecen-1-ol and 9-dodecen-1- ol, preferably comprising at least 9-decen-1-ol (see above for the advantageous properties of these fatty alcohols), and/or one or more other surfactants, preferably one or more other nonionic or anionic surfactants.
  • Such a preferred product according to the invention is preferably produced in a preferred method according to the invention in which in step (S4) the fatty alcohol, preferably 9-decen-1-ol, is not fully implemented, so that a proportion of the Fatty alcohol mixed with the resulting fatty alcohol alkoxylate, fatty alcohol polyglycoside, fatty alcohol sulfate, fatty alcohol alkoxylate sulfate or the resulting fatty alcohol hol alkoxylate carboxylic acid remains, with a portion of the fatty alcohol used in step (S4) also remaining is not separated from the produced fatty alcohol alkoxylate, fatty alcohol polyglycoside, fatty alcohol sulfate, fatty alcohol alkoxylate sulfate or from the produced fatty alcohol alkoxylate carboxylic acid at a later stage of the process.
  • the fatty alcohol preferably 9-decen-1-ol
  • products which, in addition to the new fatty alcohol alkoxylates (with an unsaturated carbon chain), alkenyl polyglycosides (especially alkenyl polyglucosides), fatty alcohol sulfates, fatty alcohol alkoxylate sulfates and fatty alcohol alkoxylate -Carbonic acids (each with an unsaturated carbon chain) based on 9-decen-1-ol, 9-undecen-1-ol and 9-dodecen-1-ol each include a portion of the unreacted fatty alcohol. This applies in particular and for the reasons already explained above to 9-decen-1-ol.
  • bio-based preferably vegetable oil-based substances selected from the group consisting of 9-decen-1-ol, 9-undecen-1-ol and 9-dodecen-1-ol to the combined total mass - the total mass of bio-based surfactants present in the product, preferably the total mass of the surfactants present in the product, and the total mass of the bio-based substances selected from the group consisting of 9-decen-1-ol, 9-undecen-1-ol and 9-dodecen-1-ol and/or the part of the
  • Total mass of bio-based, preferably vegetable oil-based 9-dodecen-1-ol to the combined total mass of the total mass of bio-based surfactants present in the product preferably the total mass of surfactants present in the product and the total mass of bio-based 9-dodecen-1-ol in the range from 1% by weight to 25% by weight, preferably in the range from 2% by weight to 20% by weight, preferably in the range from 3% by weight to 15% by weight, particularly preferably im ranges from 5% to 10% by weight.
  • the total mass of alkoxylate carboxylic acids of 9-dodecen-1-ol and - the total mass of 9-dodecen-1-ol optionally in the range of 1% by weight to 25% by weight, preferably in the range of 2 % by weight to 20% by weight, preferably in the range from 3% by weight to 15% by weight, particularly preferably in the range from 5% by weight to 10% by weight.
  • bio-based, preferably vegetable oil-based substances is preferred within the scope of the present invention.
  • Bio-based and in particular vegetable oil-based substances can be distinguished from petrochemical-based substances using the radiocarbon method, see prEN 17035:2018 (Draft of September 2018 of DIN EN 17035).
  • the measured values determined are a suitable indicator for the degree of sustainability achieved.
  • a product according to the invention (as just described) is preferred, where the proportion of the isotope 14 C in the total number of carbon atoms of the 9-decen-1-ol, the 9-unde- cen-1-ol, the 9-dodecen-1 - ols, the total number of carbon atoms in the lipophilic carbon chain or the total number of carbon atoms including the hydrophilic part of the molecule of the respective corresponding alkoxylates, polyglycosides, sulfates, alkoxylate sulfates or alkoxylate carboxylic acids is greater than 0.5 * 10 -12 , preferably greater than 0 , 6 * 10 -12, more preferably greater than 0.7 * 10 ⁇ 12th
  • the radiocarbon method according to EN 16640 shall be used unless otherwise stated; mixtures are separated chromatographically where possible. Appendix B of EN 16640 must be observed.
  • a product according to the invention (as described above) is preferred in particular if in a product comprising one or more fatty alcohols, the proportion of fatty alcohols containing 14 carbon atoms which corresponds to an age of the corresponding carbon atoms of less than 300 years since carbon dioxide fixation, determined using the radiocarbon method, is at least 50% by weight.
  • % is preferably at least 80% by weight, particularly preferably at least 90% by weight, very particularly preferably at least 99% by weight, based on the total mass of the fatty alcohols contained in the product and/or in a product comprising one or several fatty alcohol alkoxylates the proportion of fatty alcohol alkoxylates with a lipophilic carbon chain that has a proportion of 14 carbon atoms which corresponds to an age of the corresponding carbon atoms of less than 300 years since carbon dioxide fixation, determined using the radiocarbon method, is at least 50% by weight, preferably at least 80% by weight, particularly preferably at least 90% by weight, very particularly s preferably at least 99 wt of 14 carbon atoms, which corresponds to an age of the corresponding carbon atoms of less than 300 years since carbon dioxide fixation, determined using the radiocarbon method, is at least 50% by weight, preferably at least 80% by weight, particularly preferably at least 90 Wt Carbon chain that has a portion of 14 C-atoms, which indicates an age of the corresponding carbon
  • a lipophilic residue of a fatty alcohol alkoxylate has a proportion of 14 carbon atoms which corresponds to an age of the corresponding carbon atoms of less than 300 years since carbon dioxide fixation, determined using the radiocarbon method, then this lipophilic residue is not entirely based on fossil raw materials .
  • the total mass of the fatty alcohol alkoxylates present in the product it is preferable if at least 50% by weight of these fatty alcohol alkoxylates comprise such lipophilic residues that are not based exclusively on fossil raw materials.
  • a compound or an organic group with a proportion of 14 C-atoms, which corresponds to an age of the corresponding carbon atoms of less than 300 years since carbon dioxide fixation, determined using the radiocarbon method, is classified by the specialist as "bio-based" and sustainable. It is not or not entirely based on petrochemical raw materials.
  • the proportion of 14 carbon atoms in the total amount of carbon atoms measured using the radiocarbon method is a quantitative measure of the biogenicity of the carbon source and of the sustainability achieved.
  • the proportion of surfactants (total) with a lipophilic carbon chain that has a proportion of 14 carbon atoms, which corresponds to an age of the corresponding carbon atoms of less than 300 years since carbon dioxide fixation, determined using the radiocarbon method is at least 50% by weight, preferably at least 80% by weight, particularly preferably at least 90% by weight, very particularly preferably at least 99% by weight, based on the total mass of surfactants in the product. It is thus particularly preferred that, based on the total mass of surfactants in the product, at least 50% by weight of these surfactants have a lipophilic carbon chain that is not entirely based on fossil/petrochemical raw materials.
  • All nonionic and anionic surfactants contained in a product according to the invention preferably have a proportion of 14 carbon atoms, preferably in the respective lipophilic part of the molecule, which corresponds to an age of the corresponding carbon atoms of less than 300 years since carbon dioxide fixation, determined using the radiocarbon method. All surfactants contained in the product preferably have such a proportion of 14 carbon atoms, preferably in the respective lipophilic part of the molecule. All surfactants contained in the mixture then comprise carbon atoms of non-fossil origin. This is particularly advantageous from the point of view of sustainability.
  • a product according to the invention is preferably selected from the group consisting of detergents, cleaning agents and cosmetic products. The above statements apply accordingly.
  • Products according to the invention consisting of one or more bio-based, preferably vegetable oil-based substances selected from the group consisting of 9-decen-1-ol, 9-undecen-1-ol, 9-dodecen-1-ol, their respective alkoxylates, polyglycosides, Sulfates, alkoxylate sulfates and alkoxylate carboxylic acids are preferred as sustainable base chemicals for use in chemical syntheses and as surfactant components in the manufacture of detergents, cleaning agents and cosmetic products.
  • a reliable differentiation of bio-based substances from non-bio-based substances is possible using the radiocarbon method.
  • the invention also relates to the use of a vegetable oil or a fatty acid alkyl ester produced from vegetable oil as a starting material in a process comprising a cross-metathesis reaction for the production of a product comprising one or more vegetable oil-based substances selected from the group consisting of fatty alcohols, fatty alcohol alkoxylates, fatty alcohol polyglycosides , Fatty alcohol sulfates, fatty alcohol alkoxylate sulfates, fatty alcohol alkoxylate carboxylic acids and mixtures thereof, preferably selected for the production of a product from the group consisting of fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates , Fatty alcohol alkoxylate carboxylic acids, mixtures comprising one or more fatty alcohol alkoxylates and mixtures comprising one or more fatty alcohol polyglycosides and mixtures comprising one or more fatty alcohol sulfates and
  • the invention is based on the finding that vegetable oils or fatty acid alkyl esters produced from vegetable oil are suitable starting materials for the production of fatty alcohols (shortened in terms of chain length), fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates , Fatty alcohol alkoxylate carboxylic acids and corresponding mixtures, provided that the length and structure of the lipophilic carbon chain is modified by means of a cross-metathesis reaction and the specified products are achieved via the intermediate stage of the fatty alcohol.
  • the product is a product according to the invention (in each case preferably in an embodiment indicated above as preferred). It is also preferred if, within the scope of the use according to the invention, the product contains fatty alcohols and/or fatty alcohol alkoxylates and/or fatty alcohol polyglycosides and/or fatty alcohol sulfates and/or fatty alcohol alkoxylate sulfates and/or fatty alcohol alkoxylate carboxylic acids with a lipophilic carbon chain, the chain length of which is shortened by the cross-metathesis reaction compared to the starting material (ie the vegetable oil or the corresponding fatty acid alkyl ester).
  • the invention also relates to the use of a material comprising a vegetable oil-based substance selected from the group consisting of 9-decen-1-ol, 9-undecen-1-ol, 9-dodecen-1-ol and mixtures thereof as a starting material for the production of Fatty alcohol alkoxylates, fatty alcohol polyglycosides, fatty alcohol sulfates, fatty alcohol alkoxylate sulfates or fatty alcohol alkoxylate carboxylic acids, the double bond preferably being retained in the fatty alcohols mentioned.
  • reaction schemes are examples and only indicate selected starting materials and products of individual steps of the process according to the invention. Mass balance requirements and stoichiometric conditions are not consistently observed in the reaction schemes.
  • Fig. 1 shows, as an example of carrying out a cross-metathesis reaction in step (S2), schematically the reaction of oleic acid methyl ester (1) (only as an example of a first fatty acid alkyl ester to be used in step (S2); other unsaturated fatty acid alkyl esters are also possible according to the invention as first Fatty acid alkyl ester replaceable) with ethylene (2) (only as an example for an olefin used in step (S2); other olefins can also be used according to the invention) to form 1-decene (3) and 9-decenoic acid methyl ester (4) (only as an example for an in Step (S2) resulting second fatty acid alkyl ester; if other first fatty acid alkyl esters and/or other olefins are used, correspondingly other or further products result).
  • oleic acid methyl ester (1) only as an example of a first fatty acid alkyl ester to be used in step (S2)
  • Fig. 2 shows, as an example of the reaction in step (S3) of the second fatty acid alkyl ester to a fatty alcohol of the same chain length, schematically the reaction (selective reduction) of 9-decenoic acid methyl ester (4) (only by way of example for other second fatty acid alkyl esters that can be used in the process according to the invention).
  • 9-decen-1-ol (5) (if other second fatty acid alkyl esters are used, correspondingly other fatty alcohols each having the same chain length as the second fatty acid alkyl ester used in each case result).
  • step (S4) conversion of the fatty alcohol resulting in step (S3) to a fatty alcohol sulfate
  • step (S4) conversion of the fatty alcohol resulting in step (S3) to a fatty alcohol sulfate
  • step (S4) conversion of the fatty alcohol resulting in step (S3) to a fatty alcohol sulfate
  • schematically showing the conversion of 9-decen-1-ol (5) with sulfur trioxide (10) to the corresponding one Fatty alcohol hydrogen sulfate ( sulfuric acid ester of the fatty alcohol) (11) and the neutralization of the fatty alcohol hydrogen sulfate (11) with sodium hydroxide solution (12) to the corresponding fatty alcohol sulfate (13) and water (not shown in the scheme) (when using other fatty alcohols result in correspondingly different fatty alcohol sulfates).
  • step (S4) taking place of the fatty alcohol resulting in step (S3) to form a fatty alcohol alkoxylate sulfate
  • step (S3) to form a fatty alcohol alkoxylate sulfate
  • step (S3) to form a fatty alcohol alkoxylate sulfate
  • step (S4) taking place of the fatty alcohol resulting in step (S3) to form a fatty alcohol alkoxylate sulfate
  • step (S3) shows, as an example of the reaction in step (S4) taking place of the fatty alcohol resulting in step (S3) to form a fatty alcohol alkoxylate sulfate
  • step (S4) taking place of the fatty alcohol resulting in step (S3) to form a fatty alcohol alkoxylate carboxylic acid
  • step (S3) to form a fatty alcohol alkoxylate carboxylic acid
  • step (S3) to form a fatty alcohol alkoxylate carboxylic acid
  • step (S3) shows, as an example of the reaction in step (S4) taking place of the fatty alcohol resulting in step (S3) to form a fatty alcohol alkoxylate carboxylic acid
  • step (S3) shows, as an example of the reaction in step (S4) taking place of the fatty alcohol resulting in step (S3) to form a fatty alcohol alkoxylate carboxylic acid
  • step (S3) shows, as an example of the reaction in step (S4) taking place of the fatty alcohol resulting in step (S3) to form a fatty alcohol alkoxylate carboxylic acid
  • step (S3) shows, as an example of the reaction in step (S4) taking place of the fatty alcohol resulting in step (S3) to form
  • Ethenolysis of methyl oleate (methyl oleate) - cross-metathesis (implementation based on WO 02/076920)
  • a catalyst solution of [dichloro(phenylmethylene)bis(tricyclohexylphosphine)ruthenium] (obtained from Sigma-Aldrich as "Grubbs Catalyst M102") at a concentration of 0.01 mol/l in toluene.
  • Methyl oleate (99%, obtained from Sigma-Aldrich) is degassed with nitrogen before use.
  • a reactor in a dry box is charged with 3.5 g of the methyl oleate and catalyst solution (265 microliters of the 0.01 M solution).
  • the reactor is sealed, removed from the dry box and connected to an ethene gas bottle (ethene, 99.9%, from Air Liquide).
  • the reaction is carried out at a pressure of 420 kPa (4.2 bar) and a temperature of 30°C for a period of three hours.
  • the flask is then cooled in an ice water bath and ice water is slowly and carefully added dropwise to the mixture while stirring until hydrogen is evolved is fully completed.
  • a 10% sulfuric acid solution is then added dropwise with stirring until the aluminum hydroxide precipitate that has formed has just dissolved.
  • the two phases are separated in a separating funnel, and the aqueous phase is extracted again with ether. After the ether phases have been combined, they are washed with saturated sodium chloride solution and the ether phase which has been separated off again is then dried over sodium sulfate. After filtering off and then distilling off the solvent, the desired fatty alcohol is obtained.
  • reaction product mixture from step a) (comprising butyl glucoside) present in the flask is slowly and continuously added at a temperature of about 140°C dripped.
  • n-butanol formed is removed from the reaction mixture immediately and continuously by distillation. As soon as the visible formation of n-butanol has ended, the Reaction completed by applying a reduced pressure of 20 mbar with continuous supply of heat and the majority of the excess 9-decen-1-ol separated from the reaction product by distillation.
  • reaction mixture is allowed to cool, and the reaction product is mixed with 150 ml dist. Water and neutralize the mixture with 0.95 g of 5% sodium hydroxide solution.
  • the aqueous solution is then shaken out three times with 150 ml of diethyl ether in order to separate off the remaining 9-decen-1-ol.
  • the desired 9-decen-1-ol glucoside is obtained by removing the water completely, e.g., by freeze drying.
  • Example 4-2 Conversion of the fatty alcohol into a fatty alcohol ethoxylate (*2 mol EO)
  • Example 4-3 Conversion of the fatty alcohol into a fatty alcohol sulfate (fatty alkyl sulfate)
  • the ether is then drawn off on a rotary evaporator.
  • the remaining aqueous solution contains the desired fatty alcohol ether sulfate sodium salt (here: sodium 9-decenol*2EO sulfate).
  • the anhydrous surfactant is obtained by freeze drying.
  • Example 4-5 Conversion of the fatty alcohol ethoxylate into a fatty alcohol ethoxylate carboxylic acid (fatty alcohol ether carboxylic acid)
  • the reaction mixture contains (in addition to approx. 10% residual water) approx. 43 g (approx. 0.14 mol) of the desired 9-decenol*2EO acetic acid (yield of approx. 70% based on the 9-decenol*2EO used) .
  • the anhydrous reaction product can be obtained by freeze drying.

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Abstract

L'invention concerne un procédé de production d'un produit comprenant une ou plusieurs substances biosourcées choisies dans le groupe constitué par des alcools gras, des alcoxylates d'alcool gras, des polyglycosides d'alcool gras, des sulfates d'alcools gras, des sulfates d'alcoxylate d'alcool gras, des acides carboxyliques d'alcoxylate d'alcool gras et leurs mélanges. L'invention concerne en outre un produit pouvant être élaboré selon un procédé de l'invention. Enfin, l'invention concerne également l'utilisation d'une huile végétale ou d'un ester alkylique d'acide gras élaboré à partir d'huile végétale en guise de matière de départ dans un procédé de production d'un produit comprenant une réaction de métathèse croisée. La présente invention a trait au domaine technique des tensioactifs et concerne ainsi des produits qui s'adressent directement aux consommateurs, dans le domaine technique des détergents, des produits de nettoyage et des produits cosmétiques.
PCT/EP2021/069583 2020-07-17 2021-07-14 Procédé de production d'un produit biosourcé, produit correspondant et utilisations Ceased WO2022013278A1 (fr)

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