EP3707123A1 - Alkoxylated secondary alcohol sulfates - Google Patents

Alkoxylated secondary alcohol sulfates

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Publication number
EP3707123A1
EP3707123A1 EP18821707.9A EP18821707A EP3707123A1 EP 3707123 A1 EP3707123 A1 EP 3707123A1 EP 18821707 A EP18821707 A EP 18821707A EP 3707123 A1 EP3707123 A1 EP 3707123A1
Authority
EP
European Patent Office
Prior art keywords
cation
compound according
formula
agent
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP18821707.9A
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German (de)
French (fr)
Inventor
Jean-Philippe Gillet
Juan Antonio Gonzalez Leon
Carl Bouret
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arkema France SA
Original Assignee
Arkema France SA
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Filing date
Publication date
Application filed by Arkema France SA filed Critical Arkema France SA
Publication of EP3707123A1 publication Critical patent/EP3707123A1/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
    • C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/02—Alkyl sulfonates or sulfuric acid ester salts derived from monohydric alcohols
    • 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

Definitions

  • the present invention relates to the general field of alkoxylated secondary alcohols which are subjected to a sulfation reaction.
  • Fatty alcohol sulfates are known as surfactants in various applications. Indeed, they have a number of intrinsic properties in comparison with other cationic and anionic surfactants.
  • the main intermediate for the synthesis of organic alcohol sulphates is the organic alcohol itself. Different properties for an alcohol sulfate can be obtained, depending on the organic alcohol chosen as raw material.
  • organic alcohols used to synthesize these sulfates can be very different in nature, for example: linear or branched, small or large molar mass, mono or multifunctional, among others.
  • They may also be organic alcohols which have undergone an alkoxylation step, in which one or more units of an alkyl oxide, for example ethylene oxide, propylene oxide, butylene oxide, have been incorporated in said organic alcohol.
  • an alkyl oxide for example ethylene oxide, propylene oxide, butylene oxide
  • Alkoxylates of secondary alcohols represent a family of compounds offering a wide range of properties. Indeed, the applications are multiple. They can especially be used as solvents, as hydrotopes or as nonionic surfactants. They can also act as raw materials for other compounds such as etheramines or anionic surfactants obtained by phosphatation or sulfation. Thus, alkoxylates of secondary alcohols constitute a class of compounds of major industrial interest for many actors. [0009] In a conventional manner, the alkoxylates of secondary alcohols are synthesized using basic catalysis, using, for example, potassium hydroxide. Another type of catalyst may also be employed, the dimethyl cyanide catalyst, commonly known as DMC catalyst. Various documents refer to the alkoxylation of various compounds, including alcohols, by basic catalysis and / or by DMC catalysis.
  • the present invention aims to provide a solution to solve the problems mentioned above.
  • the groups R 1 and F3 ⁇ 4 which are identical or different, represent, independently of one another, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group comprising from 1 to 6 carbon atoms, it being understood that the sum of carbon atoms of the groups R 1 and F3 ⁇ 4 ranges from 2 to 7, R 1 and R 2 may form, together with the carbon atom carrying them, a ring with 6, 7 or 8 vertices,
  • A represents a sequence of one or more units chosen from ethylene oxide, propylene oxide and butylene oxide units and mixtures thereof, and
  • n is an integer between, inclusive, 1 and 100, preferably between 2 and 100, more preferably between 3 and 100, more preferably between 5 and 100, and most preferably between 10 and 100.
  • the present invention also relates to the salts of the compounds of formula (I) above with one or more cationic groups bearing at least one cation selected from ammonium cation, metal cation, nitrogen cation, boron cation, cation phosphorus.
  • these salts can be described by the following formula (II):
  • - M x + represents a cationic group bearing at least one cation selected from ammonium cation, metal cation, nitrogen cation, boron cation, phosphorus cation,
  • x is an integer ranging from 1 to 7, and
  • Ri, R2, A and n being as defined above.
  • the present invention also relates to a mixture of at least one compound of formula (I) and at least one compound of formula (II).
  • compound of formula (I) designates at least one compound of formula (I) or at least one of its salts of formula (II) or a mixture of at least one compound of formula (I) with at least one of its salts of formula (II).
  • Another object of the invention is the use of the compound of formula (I) according to the invention, as a surfactant, surfactant with low foaming surfactant ("low-foaming surfactant" language English), wetting agent, foaming agent, hydrotrope, detergent, solvent, reactive solvent, coalescing agent, compatibilizer, emulsifying agent, dispersant, chemical intermediate, corrosion inhibitor, demulsifier, plasticizer, sequestering agent, inorganic deposit inhibitor, ionic liquid , stabilizer, lubricant, bitumen additive, de-inking additive, gelling agent in oils, flotation collector for ores, processing aid in plastics manufacturing, antistatic agent, additive for fertilizer coatings, for plant protection, textile processing and enhanced oil recovery, for electrode production and electrolytes for batteries.
  • ethylene oxide unit the unit derived from ethylene oxide after opening the oxirane ring.
  • propylene oxide unit the unit derived from propylene oxide after opening the oxirane ring.
  • butylene oxide unit also refers to the unit derived from butylene oxide after opening the oxirane ring.
  • the compound according to the invention is a compound of formula (I) as mentioned above or a salt thereof of formula (II) as mentioned above.
  • the groups R 1 and F3 ⁇ 4 with the carbon atom to which they are attached, denote a secondary radical comprising from 3 to 8 carbon atoms, preferably from 6 to 8 carbon atoms.
  • the moieties Ri and F3 ⁇ 4 identical or different are chosen, independently of each other, from methyl, ethyl, n-propyl, / 'so-propyl, n-butyl, sec -butyl, ie / f-butyl, pentyles, and hexyls.
  • the radical formed by R 1, R 2 and the carbon atom to which they are attached is chosen from the 2-octyl radical and the 4-methyl-2-pentyl radical. More particularly, the radical formed by R 1, R 2 and the carbon atom to which they are attached is the 2-octyl radical.
  • n is between, inclusive, 1 and 75, preferably between 2 and 75, more preferably between 3 and 75, more particularly between 5 and 75, and very preferably between 10 and 75.
  • n is between, inclusive, 1 and 50, preferably between 2 and 50, more preferably between 3 and 50, more particularly between 5 and 50, and very preferably between 10 and 50.
  • n is between, included terminals, 1 and 30, preferably between 2 and 30, more preferably between 3 and 30, more particularly between 5 and 30, and very preferably between 10 and 30.
  • n ranges from 2 to 30.
  • A represents a sequence of one or more units selected from ethylene oxide units, propylene oxide, butylene oxide and mixtures thereof.
  • the compound of formula (I) when the compound of formula (I) comprises a mixture of said different patterns, they may be randomly, alternately or in blocks.
  • A represents a sequence of at least one ethylene oxide unit and at least one propylene oxide unit, distributed alternately, randomly or in blocks.
  • A represents a sequence of at least one ethylene oxide unit and at least one butylene oxide unit, distributed alternately, randomly or in blocks.
  • A represents a sequence of at least one propylene oxide unit and at least one butylene oxide unit, distributed alternately, randomly or in blocks.
  • the group formed by R 1, F3 ⁇ 4 and the carbon atom to which R 1 and F3 ⁇ 4 are attached represents the 2-octyl radical, n ranges from 3 to 15, and A represents a sequence of one or more units selected from ethylene oxide units, propylene oxide, butylene oxide and mixtures thereof.
  • the invention also relates to mixtures of secondary alcohol sulfates according to formula (I) as defined above.
  • the invention also relates to the salts of the compounds of formula (I) as defined above.
  • the subject of the invention is the compound of formula (I) in salt form with an alkaline cation, an alkaline earth cation, a metal cation or with an organic compound, including organic bases.
  • these salts may be addition salts of a compound of formula (I) with a base, organic or inorganic.
  • These salts may be salts of organic amines, said amines may contain one or two or more amine groups.
  • the amines that can be used for salifying the compounds of formula (I) as defined above, are preferably chosen, and non-imitatively, from alkylamines, cycloalkylamines, aromatic amines, and alkanolamines, said amines possibly being primary, secondary or tertiary, and may also be alkoxylated.
  • the compounds of formula (I) may also be salts of heterocyclic amines or urea.
  • the salts of the compounds of formula (I) with the ammonium cation (NH 4 + ) are also part of the invention.
  • These salts may be inorganic salts.
  • these salts are the salts of the compounds of formula (I) with the elements of column 1 of the periodic table of the elements (alkali metals) such as lithium, sodium, potassium, rubidium and cesium.
  • the salts of the compounds of formula (I) are the salts with the elements of column 2 of the periodic table of the (alkaline earth) elements, for example magnesium and calcium.
  • the salts of the compounds of formula (I) are the salts with the elements of columns 3 to 13 of the periodic table of the elements (transition metals), for example vanadium , manganese, cobalt, zirconium, yttrium, iron, cadmium, aluminum and zinc.
  • the salts of the compounds of formula (I) are those with rare earths (lanthanides and actinides), such as, for example, lanthanum, cerium, thorium, uranium and plutonium. .
  • the compound of formula (I) according to the present invention can be obtained advantageously by sulfation of an alkoxylated secondary alcohol, according to methods well known to those skilled in the art.
  • sulfation comprises reacting the secondary alcohol with a sulfated compound selected from sulfur trioxide, sulfuric acid, oleum, sulfur trioxide, sulfur trioxide complexes, sulfamic acid, chlorosulfonic acid, among others.
  • the secondary alcohol used to synthesize the compound of formula (I) is chosen from 2-octanol and methylisobutylcarbinol, preferably the secondary alcohol is 2-octanol.
  • This alcohol has a particular interest in several ways. Indeed, it is a bio-sourced, biodegradable product with a good ecotoxicological profile. In addition, the boiling point of 2-octanol is high and its cost is quite reasonable.
  • the alkoxylation of the secondary alcohol used to synthesize the compound of formula (I) is obtained using a catalyst of dimetallic cyanide type, also called DMC catalyst.
  • the dimetallic cyanide catalyst may be of any type known to those skilled in the art. This catalyst is described in particular in patents US6429342, US6977236 and PL398518. More particularly, the catalyst used is zinc hexacyanocobaltate, for example sold by Bayer under the name Arcol ® or by Mexeo under the name MEO-DMC ® .
  • Another object of the invention is the use of the compound of formula (I) according to the invention defined above, and / or a salt thereof, alone or as a mixture, as surfactant, surfactant at low foaming power, wetting agent, foaming agent, hydrotrope, detergent, solvent, reactive solvent, coalescing agent, compatibilizer, emulsifying agent, dispersant, chemical intermediate, corrosion inhibitor, demulsifier, plasticizer, sequestering agent, mineral deposit inhibitor, liquid ionic, stabilizer, lubricant, bitumen additive, de-inking additive, gelling agent in oils, flotation collector for ores, processing aids in the manufacture of plastic objects, antistatic agent, additive for fertilizer coatings, for plant protection, for the treatment of textiles and for enhanced oil recovery, for the production of electrodes and electrolytes for batteries, to name only some of the most common applications known for this type of compounds.
  • the present invention relates to a composition
  • a composition comprising at least one compound of formula (I) as defined above, and / or one of its salts, alone or as a mixture, with one or more aqueous solvents, organic, hydroorganic, such as for example water, alcohols, glycols, polyols, mineral oils, vegetable oils, and others, alone or in mixtures of two or more of them, in all proportions.
  • composition according to the invention may also contain one or more additives and fillers well known to those skilled in the art, such as, for example, and without limitation, anionic, cationic, amphoteric, nonionic surfactants. , rheology modifiers, de-emulsifiers, anti-deposition agents, defoamers, dispersants, pH control agents, dyes, antioxidants, preservatives, corrosion inhibitors, biocides, and other additives such as, for example, sulfur-containing products , boreas nitrogenous, phosphates, and others.
  • additives and fillers can vary in large proportions depending on the nature of the application envisaged and can easily be adapted by those skilled in the art.
  • the 2-octanol (CAS RN 123-96-6) used is 2 octanol Oleris ® grade "Refined"(purity> 99%), marketed by Arkema France.
  • Step 1 a Propoxylation of 2-octanol
  • the remainder of the propylene oxide is introduced, a total of 792 g (13.62 M) over a period of 60 minutes, at a temperature of 140-150 ° C.
  • the temperature is maintained for 30 minutes and then the residual propylene oxide is stripped off under a stream of nitrogen ("stripping").
  • the reactor is cooled to 60 ° C. and 1381 g of alkoxylated 2-octanol comprising 3 propylene oxide units (3 PO) are withdrawn.
  • Step 1b Sulfation of propoxylated 2-octanol
  • Step 2a ethoxylation of 2-octanol
  • the reaction medium is heated to 120 ° C with stirring. At this temperature of 120 ° C., 40 g of ethylene oxide are introduced. When the initiation of the reaction is noted, the remainder of the ethylene oxide is fed in a total of 628 g (14.27 M) for 60 minutes at a temperature of 140-150 ° C. At the end of the addition, the temperature is kept 30 minutes, then stripped with nitrogen the residual ethylene oxide.
  • the reactor is cooled to 60 ° C. and 1240 g of alkoxylated 2-octanol comprising 3 ethylene oxide units are withdrawn. (IOH: 210 mg KOH / g and 26 Hz staining).
  • Step 2b sulfation of ethoxylated 2-octanol
  • reaction is followed by the amount of hydrochloric acid produced. It is considered that the reaction is complete when the values do not vary. About 340 g of alkoxylated 2-octanol sulphate comprising 3 ethylene oxide units (3 EO) are recovered.

Abstract

The invention relates to the compounds of formula (I), in which R1 and R2 represent a linear, branched or cyclic, saturated or unsaturated hydrocarbon group, comprising 1 to 6 carbon atoms, wherein the sum of the carbon atoms of the groups R1 and R2 is from 2 to 7, A represents a chain of one or a plurality of units of ethylene oxide, propylene oxide, butylene oxide and the mixtures thereof, and n is an integer between 1 and 100 inclusive. The invention also relates to the mineral or organic salts thereof. The invention further relates to the use of the compounds of formula (I) and/or to one of the salts thereof as a surfactant, a wetting agent, a detergent, an emulsifying agent, a dispersant, a corrosion inhibitor, and the like. The invention further relates to the compositions comprising at least one compound of formula (I) and/or to one of the salts thereof.

Description

SULFATES D'ALCOOLS SECONDAIRES ALCOXYLÉS  ALCOHOLIC SECONDARY ALCOHOL SULFATES
[0001] La présente invention concerne le domaine général des alcools secondaires alcoxylés auxquels on fait subir une réaction de sulfatation. The present invention relates to the general field of alkoxylated secondary alcohols which are subjected to a sulfation reaction.
[0002] La sulfatation des alcools organiques est une voie bien connue pour obtenir des sulfates d'alcools organiques. Les sulfates d'alcools gras sont connus en tant que tensioactifs dans différentes applications. En effet, ils sont dotés d'un certain nombre de propriétés intrinsèques en comparaison avec d'autres tensioactifs cationiques et anioniques.  Sulfation of organic alcohols is a well-known way to obtain sulphates of organic alcohols. Fatty alcohol sulfates are known as surfactants in various applications. Indeed, they have a number of intrinsic properties in comparison with other cationic and anionic surfactants.
[0003] L'intermédiaire principal pour la synthèse de sulfates d'alcools organiques est l'alcool organique lui-même. Différentes propriétés pour un sulfate d'alcool peuvent être obtenues, selon l'alcool organique choisi comme matière première.  [0003] The main intermediate for the synthesis of organic alcohol sulphates is the organic alcohol itself. Different properties for an alcohol sulfate can be obtained, depending on the organic alcohol chosen as raw material.
[0004] Les alcools organiques utilisés pour synthétiser ces sulfates peuvent être de nature très différente, par exemple : linéaires ou ramifiés, de petite ou de grande masse molaire, mono ou plurifonctionnel, entre autres. The organic alcohols used to synthesize these sulfates can be very different in nature, for example: linear or branched, small or large molar mass, mono or multifunctional, among others.
[0005] Ils peuvent être aussi des alcools organiques qui ont subi une étape d'alcoxylation, dans laquelle un ou plusieurs motifs d'un oxyde d'alkyle, par exemple d'oxyde d'éthylène, d'oxyde de propylène, d'oxyde de butylène, ont été incorporés audit alcool organique.  They may also be organic alcohols which have undergone an alkoxylation step, in which one or more units of an alkyl oxide, for example ethylene oxide, propylene oxide, butylene oxide, have been incorporated in said organic alcohol.
[0006] La synthèse des sulfates d'alcools organiques présente un réel intérêt industriel, tout particulièrement lorsque cette synthèse est simple à mettre en œuvre et peu onéreuse, notamment à partir de matières premières disponibles et facilement modifiables pour obtenir des propriétés différentes. The synthesis of organic alcohol sulphates is of real industrial interest, especially when this synthesis is simple to implement and inexpensive, especially from raw materials available and easily modifiable to obtain different properties.
[0007] En outre, à l'heure où l'enjeu environnemental est véritablement important, l'utilisation d'un réactif bio-sourcé ou biodégradable et présentant un bon profil écotoxicologique est tout à fait intéressant à envisager.  In addition, at a time when the environmental issue is really important, the use of a bio-sourced or biodegradable reagent and having a good ecotoxicological profile is quite interesting to consider.
[0008] Les alcoxylats d'alcools secondaires représentent une famille de composés offrant un large éventail de propriétés. En effet, les applications sont multiples. Ils peuvent notamment être utilisés en tant que solvants, en tant qu'hydrotopes ou encore en tant que tensioactifs non ioniques. Ils peuvent également jouer le rôle de matière première pour d'autres composés tels que les étheramines ou des tensioactifs anioniques obtenus par phosphatation ou sulfatation. Ainsi, les alcoxylats d'alcools secondaires constituent une classe de composés revêtant un intérêt industriel majeur pour de nombreux acteurs. [0009] De manière classique, les alcoxylats d'alcools secondaires sont synthétisés à l'aide d'une catalyse basique, en utilisant par exemple de l'hydroxyde de potassium. Un autre type de catalyseur peut également être employé, le catalyseur de type cyanure dimétallique, communément appelé catalyseur DMC. Divers documents font référence à l'alcoxylation de divers composés, dont les alcools, par une catalyse basique et/ou par une catalyse DMC. Alkoxylates of secondary alcohols represent a family of compounds offering a wide range of properties. Indeed, the applications are multiple. They can especially be used as solvents, as hydrotopes or as nonionic surfactants. They can also act as raw materials for other compounds such as etheramines or anionic surfactants obtained by phosphatation or sulfation. Thus, alkoxylates of secondary alcohols constitute a class of compounds of major industrial interest for many actors. [0009] In a conventional manner, the alkoxylates of secondary alcohols are synthesized using basic catalysis, using, for example, potassium hydroxide. Another type of catalyst may also be employed, the dimethyl cyanide catalyst, commonly known as DMC catalyst. Various documents refer to the alkoxylation of various compounds, including alcohols, by basic catalysis and / or by DMC catalysis.
[0010] Ainsi, il est recherché un sulfate d'alcool secondaire, ledit alcool étant à chaîne courte et alcoxylé, dont l'alcoxylation est réalisée par un procédé simple et permet un développement industriel et commercial à faible coût. Il serait également avantageux de développer un procédé de préparation de ces sulfates mettant en œuvre des alcools secondaires alcoxylés dont le composé de départ est un réactif bio-sourcé et biodégradable.  Thus, it is sought a secondary alcohol sulfate, said alcohol being short chain and alkoxylated, the alkoxylation is carried out by a simple process and allows industrial and commercial development at low cost. It would also be advantageous to develop a process for the preparation of these sulphates using alkoxylated secondary alcohols, the starting material of which is a bio-sourced and biodegradable reagent.
[0011] La présente invention a pour objet de proposer une solution permettant de résoudre les problèmes mentionnés ci-dessus.  The present invention aims to provide a solution to solve the problems mentioned above.
[0012] L'invention a pour objet les composés de formule (I) suivante :  The subject of the invention is the compounds of formula (I) below:
dans laquelle : in which :
- les groupements Ri et F¾, identiques ou différents, représentent, indépendamment l'un de l'autre, un groupement hydrocarboné linéaire, ramifié ou cyclique, saturé ou insaturé, comprenant de 1 à 6 atomes de carbone, étant entendu que la somme des atomes de carbone des groupements Ri et F¾ va de 2 à 7, Ri et R2 pouvant former ensemble et avec l'atome de carbone qui les porte, un cycle à 6, 7 ou 8 sommets,  the groups R 1 and F¾, which are identical or different, represent, independently of one another, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group comprising from 1 to 6 carbon atoms, it being understood that the sum of carbon atoms of the groups R 1 and F¾ ranges from 2 to 7, R 1 and R 2 may form, together with the carbon atom carrying them, a ring with 6, 7 or 8 vertices,
- A représente un enchaînement d'un ou plusieurs motifs choisis parmi les motifs oxyde d'éthylène, oxyde de propylène, oxyde de butylène et leurs mélanges, et  A represents a sequence of one or more units chosen from ethylene oxide, propylene oxide and butylene oxide units and mixtures thereof, and
- n est un nombre entier compris entre, bornes incluses, 1 et 100, de préférence entre 2 et 100, de préférence encore entre 3 et 100, plus particulièrement entre 5 et 100, et de manière très préférée entre 10 et 100.  n is an integer between, inclusive, 1 and 100, preferably between 2 and 100, more preferably between 3 and 100, more preferably between 5 and 100, and most preferably between 10 and 100.
[0013] La présente invention a également pour objet les sels des composés de formule (I) ci-dessus avec un ou plusieurs groupements cationiques porteurs d'au moins un cation choisi parmi cation ammonium, cation métallique, cation azoté, cation boré, cation phosphoré. [0014] Des exemples de ces sels euvent être décrits par la formule (II) suivante : The present invention also relates to the salts of the compounds of formula (I) above with one or more cationic groups bearing at least one cation selected from ammonium cation, metal cation, nitrogen cation, boron cation, cation phosphorus. Examples of these salts can be described by the following formula (II):
dans laquelle : in which :
- Mx+ représente un groupement cationique porteur d'au moins un cation choisi parmi cation ammonium, cation métallique, cation azoté, cation boré, cation phosphoré,- M x + represents a cationic group bearing at least one cation selected from ammonium cation, metal cation, nitrogen cation, boron cation, phosphorus cation,
- x est un nombre entier allant de 1 à 7, et x is an integer ranging from 1 to 7, and
- Ri, R2, A et n étant tels que définis précédemment.  Ri, R2, A and n being as defined above.
[0015] La présente invention a également pour objet un mélange d'au moins un composé de formule (I) et d'au moins un composé de formule (II). Dans la suite du présent exposé, et sauf indication contraire, l'expression « composé de formule (I) » désigne au moins un composé de formule (I) ou au moins un de ses sels de formule (II) ou un mélange d'au moins un composé de formule (I) avec au moins un de ses sels de formule (II).  The present invention also relates to a mixture of at least one compound of formula (I) and at least one compound of formula (II). In the remainder of the present description, and unless otherwise indicated, the expression "compound of formula (I)" designates at least one compound of formula (I) or at least one of its salts of formula (II) or a mixture of at least one compound of formula (I) with at least one of its salts of formula (II).
[0016] Un autre objet de l'invention est l'utilisation du composé de formule (I) selon l'invention, en tant qu'agent tensioactif, agent tensio-actif à faible pouvoir moussant (« low- foaming surfactant » en langue anglaise), agent de mouillage, agent moussant, hydrotrope, détergent, solvant, solvant réactif, agent de coalescence, compatibilisant, agent émulsifiant, dispersant, intermédiaire chimique, inhibiteur de corrosion, désémulsionnant, plastifiant, séquestrant, inhibiteur de dépôts minéraux, liquide ionique, stabilisant, lubrifiant, additif pour bitumes, additif pour désencrage, agent gélifiant dans les huiles, collecteur de flottation pour les minerais, adjuvant de fabrication (« processing aid » en langue anglaise) dans la manufacture des objets plastiques, agent antistatique, additif pour les revêtements d'engrais, pour la protection des plantes, pour le traitement des textiles et pour la récupération assistée du pétrole, pour la production d'électrodes et d'électrolytes pour batteries. Another object of the invention is the use of the compound of formula (I) according to the invention, as a surfactant, surfactant with low foaming surfactant ("low-foaming surfactant" language English), wetting agent, foaming agent, hydrotrope, detergent, solvent, reactive solvent, coalescing agent, compatibilizer, emulsifying agent, dispersant, chemical intermediate, corrosion inhibitor, demulsifier, plasticizer, sequestering agent, inorganic deposit inhibitor, ionic liquid , stabilizer, lubricant, bitumen additive, de-inking additive, gelling agent in oils, flotation collector for ores, processing aid in plastics manufacturing, antistatic agent, additive for fertilizer coatings, for plant protection, textile processing and enhanced oil recovery, for electrode production and electrolytes for batteries.
[0017] D'autres avantages et caractéristiques de l'invention apparaîtront plus clairement à l'examen de la description détaillée. Il est précisé que les expressions « de... à... » utilisées dans la présente description doivent s'entendre comme incluant chacune des bornes mentionnées. Other advantages and features of the invention will appear more clearly on examination of the detailed description. It is specified that the expressions "from ... to ..." used in the present description must be understood as including each of the mentioned terminals.
[0018] Au sens de la présente invention, on entend par « motif oxyde d'éthylène » le motif issu de l'oxyde d'éthylène après ouverture du cycle oxirane. De même on entend par « motif oxyde de propylène » le motif issu de l'oxyde de propylène après ouverture du cycle oxirane. De manière similaire également, on entend par « motif oxyde de butylène » le motif issu de l'oxyde de butylène après ouverture du cycle oxirane. [0019] Le composé selon l'invention est un composé de formule (I) telle que mentionnée ci-dessus ou un de ses sels de formule (II) telle que mentionnée ci-dessus. For the purposes of the present invention, the term "ethylene oxide unit" the unit derived from ethylene oxide after opening the oxirane ring. Similarly, the term "propylene oxide unit" the unit derived from propylene oxide after opening the oxirane ring. Similarly, the term "butylene oxide unit" also refers to the unit derived from butylene oxide after opening the oxirane ring. The compound according to the invention is a compound of formula (I) as mentioned above or a salt thereof of formula (II) as mentioned above.
[0020] En d'autres termes, les groupements Ri et F¾, avec l'atome de carbone auquel ils sont rattachés, désignent un radical secondaire comprenant de 3 à 8 atomes de carbone, de préférence de 6 à 8 atomes de carbone. In other words, the groups R 1 and F¾, with the carbon atom to which they are attached, denote a secondary radical comprising from 3 to 8 carbon atoms, preferably from 6 to 8 carbon atoms.
[0021] De préférence, les groupements Ri et F¾, identiques ou différents, sont choisis, indépendamment l'un de l'autre, parmi les radicaux méthyle, éthyle, n-propyle, /'so-propyle, n-butyle, sec-butyle, ie/f-butyle, pentyles, et hexyles. [0021] Preferably, the moieties Ri and F¾ identical or different, are chosen, independently of each other, from methyl, ethyl, n-propyl, / 'so-propyl, n-butyl, sec -butyl, ie / f-butyl, pentyles, and hexyls.
[0022] De préférence, le radical formé par Ri, R2 et l'atome de carbone auquel ils sont rattachés, est choisi parmi le radical 2-octyle et le radical 4-méthyl-2-pentyle. Plus particulièrement, le radical formé par Ri, R2 et l'atome de carbone auquel ils sont rattachés est le radical 2-octyle.  Preferably, the radical formed by R 1, R 2 and the carbon atom to which they are attached, is chosen from the 2-octyl radical and the 4-methyl-2-pentyl radical. More particularly, the radical formed by R 1, R 2 and the carbon atom to which they are attached is the 2-octyl radical.
[0023] Avantageusement, n est compris entre, bornes incluses, 1 et 75, de préférence entre 2 et 75, de préférence encore entre 3 et 75, plus particulièrement entre 5 et 75, et de manière très préférée entre 10 et 75.  Advantageously, n is between, inclusive, 1 and 75, preferably between 2 and 75, more preferably between 3 and 75, more particularly between 5 and 75, and very preferably between 10 and 75.
[0024] Avantageusement, n est compris entre, bornes incluses, 1 et 50, de préférence entre 2 et 50, de préférence encore entre 3 et 50, plus particulièrement entre 5 et 50, et de manière très préférée entre 10 et 50.  [0024] Advantageously, n is between, inclusive, 1 and 50, preferably between 2 and 50, more preferably between 3 and 50, more particularly between 5 and 50, and very preferably between 10 and 50.
[0025] Avantageusement, n est compris entre, bornes incluses, 1 et 30, de préférence entre 2 et 30, de préférence encore entre 3 et 30, plus particulièrement entre 5 et 30, et de manière très préférée entre 10 et 30.  Advantageously, n is between, included terminals, 1 and 30, preferably between 2 and 30, more preferably between 3 and 30, more particularly between 5 and 30, and very preferably between 10 and 30.
[0026] De préférence, n va de 2 à 30. Preferably, n ranges from 2 to 30.
[0027] Comme indiqué précédemment, A représente un enchaînement d'un ou plusieurs motifs choisis parmi les motifs oxyde d'éthylène, oxyde de propylène, oxyde de butylène et leurs mélanges. Selon un mode de réalisation particulier, lorsque le composé de formule (I) comporte un mélange desdits motifs différents, ils peuvent être répartis de manière aléatoire, alternée ou par blocs.  As indicated above, A represents a sequence of one or more units selected from ethylene oxide units, propylene oxide, butylene oxide and mixtures thereof. According to a particular embodiment, when the compound of formula (I) comprises a mixture of said different patterns, they may be randomly, alternately or in blocks.
[0028] Selon un mode de réalisation préféré, A représente un enchaînement d'au moins un motif oxyde d'éthylène et d'au moins un motif oxyde de propylène, répartis de manière alternée, aléatoire ou par blocs.  According to a preferred embodiment, A represents a sequence of at least one ethylene oxide unit and at least one propylene oxide unit, distributed alternately, randomly or in blocks.
[0029] Selon encore un autre mode de réalisation préféré, A représente un enchaînement d'au moins un motif oxyde d'éthylène et d'au moins un motif oxyde de butylène, répartis de manière alternée, aléatoire ou par blocs. [0030] Selon encore un autre mode de réalisation préféré, A représente un enchaînement d'au moins un motif oxyde de propylène et d'au moins un motif oxyde de butylène, répartis de manière alternée, aléatoire ou par blocs. According to yet another preferred embodiment, A represents a sequence of at least one ethylene oxide unit and at least one butylene oxide unit, distributed alternately, randomly or in blocks. According to yet another preferred embodiment, A represents a sequence of at least one propylene oxide unit and at least one butylene oxide unit, distributed alternately, randomly or in blocks.
[0031] Selon un mode de réalisation préféré de l'invention, le groupe formé par Ri, F¾ et l'atome de carbone auquel Ri et F¾ sont attachés représente le radical 2-octyle, n va de 3 à 15, et A représente un enchaînement d'un ou plusieurs motifs choisis parmi les motifs oxyde d'éthylène, oxyde de propylène, oxyde de butylène et leurs mélanges.  According to a preferred embodiment of the invention, the group formed by R 1, F¾ and the carbon atom to which R 1 and F¾ are attached represents the 2-octyl radical, n ranges from 3 to 15, and A represents a sequence of one or more units selected from ethylene oxide units, propylene oxide, butylene oxide and mixtures thereof.
[0032] L'invention porte également sur les mélanges des sulfates d'alcool secondaire selon la formule (I) tels que définis ci-dessus. The invention also relates to mixtures of secondary alcohol sulfates according to formula (I) as defined above.
[0033] L'invention a également pour objet les sels des composés de formule (I) telle que définie ci-dessus.  The invention also relates to the salts of the compounds of formula (I) as defined above.
[0034] Plus précisément l'invention a pour objet le composé de formule (I) sous forme de sel avec un cation alcalin, un cation alcalino-terreux, un cation métallique ou avec un composé organique, incluant les bases organiques.  More specifically, the subject of the invention is the compound of formula (I) in salt form with an alkaline cation, an alkaline earth cation, a metal cation or with an organic compound, including organic bases.
[0035] Comme indiqué précédemment, ces sels peuvent être des sels d'addition d'un composé de formule (I) avec une base, organique ou minérale.  As indicated above, these salts may be addition salts of a compound of formula (I) with a base, organic or inorganic.
[0036] Ces sels peuvent être des sels d'amines organiques, lesdites aminés pouvant contenir un ou deux ou plusieurs groupements amine. Les aminés utilisables pour salifier les composés de formule (I) telle que définie précédemment, sont choisies de préférence, et à titre non imitatif, parmi les alkylamines, les cycloalkylamines, les aminés aromatiques, et les alcanolamines, lesdites aminés pouvant être primaires, secondaires ou tertiaires, et pouvant être également alcoxylées.  These salts may be salts of organic amines, said amines may contain one or two or more amine groups. The amines that can be used for salifying the compounds of formula (I) as defined above, are preferably chosen, and non-imitatively, from alkylamines, cycloalkylamines, aromatic amines, and alkanolamines, said amines possibly being primary, secondary or tertiary, and may also be alkoxylated.
[0037] Les composés de formule (I) peuvent également être des sels d'amines hétérocycliques ou d'urée. Les sels des composés de formule (I) avec le cation ammonium (NH4+) font également partie de l'invention. The compounds of formula (I) may also be salts of heterocyclic amines or urea. The salts of the compounds of formula (I) with the ammonium cation (NH 4 + ) are also part of the invention.
[0038] Ces sels peuvent être des sels inorganiques. Avantageusement, ce sont les sels des composés de la formule (I) avec les éléments de la colonne 1 du tableau périodique des éléments (métaux alcalins) comme par exemple le lithium, le sodium, le potassium, le rubidium et le césium.  These salts may be inorganic salts. Advantageously, these are the salts of the compounds of formula (I) with the elements of column 1 of the periodic table of the elements (alkali metals) such as lithium, sodium, potassium, rubidium and cesium.
[0039] Selon un autre mode de réalisation avantageux de la présente invention, les sels des composés de formule (I) sont les sels avec les éléments de la colonne 2 du tableau périodique des éléments (alcalino-terreux), par exemple le magnésium et le calcium.  According to another advantageous embodiment of the present invention, the salts of the compounds of formula (I) are the salts with the elements of column 2 of the periodic table of the (alkaline earth) elements, for example magnesium and calcium.
[0040] Selon encore un autre mode de réalisation avantageux de la présente invention, les sels des composés de formule (I) sont les sels avec les éléments des colonnes 3 à 13 du tableau périodique des éléments (métaux de transition), par exemple vanadium, manganèse, cobalt, zirconium, yttrium, fer, cadmium, aluminium et zinc. [0041] Encore selon un autre mode de réalisation avantageux de la présente invention, les sels des composes de la formule (I) sont ceux avec les terre rares (lanthanides et actinides), comme par exemple lanthane, cérium, thorium, uranium et plutonium. According to yet another advantageous embodiment of the present invention, the salts of the compounds of formula (I) are the salts with the elements of columns 3 to 13 of the periodic table of the elements (transition metals), for example vanadium , manganese, cobalt, zirconium, yttrium, iron, cadmium, aluminum and zinc. According to another advantageous embodiment of the present invention, the salts of the compounds of formula (I) are those with rare earths (lanthanides and actinides), such as, for example, lanthanum, cerium, thorium, uranium and plutonium. .
[0042] Le composé de formule (I) selon la présente invention peut être obtenu avantageusement par sulfatation d'un alcool secondaire alcoxylé, selon les méthodes bien connues de l'homme du métier. Par exemple, la sulfatation consiste à faire réagir l'alcool secondaire avec un composé sulfaté choisi parmi le trioxyde de soufre, l'acide sulfurique, l'oléum, le trioxyde de soufre, les complexes des trioxydes du soufre, l'acide sulfamique, l'acide chlorosulfonique, entre autres. The compound of formula (I) according to the present invention can be obtained advantageously by sulfation of an alkoxylated secondary alcohol, according to methods well known to those skilled in the art. For example, sulfation comprises reacting the secondary alcohol with a sulfated compound selected from sulfur trioxide, sulfuric acid, oleum, sulfur trioxide, sulfur trioxide complexes, sulfamic acid, chlorosulfonic acid, among others.
[0043] Comme indiqué précédemment, la synthèse de ces sulfates et les caractéristiques de leurs procédés de préparation sont connus de l'homme du métier et sont par exemple décrits par X. Domingo dans « Anionic Surfactants », vol. 5, H. W. Stache, (1996), pages 224-279, « Encyclopedia of Chemical Technology », Kirk Othmer, 4e édition, (1997), vol. 23, pp. 146-175 ; « Ullmann's Encyclopedia oflndustrial Chemistry », 5e édition, Elvers, B., Hawkins, S., Schulz, G., (1994), vol. A25, pp. 778-783. As indicated above, the synthesis of these sulfates and the characteristics of their preparation processes are known to those skilled in the art and are for example described by X. Domingo in "Anionic Surfactants", vol. 5 HW Stache (1996), 224-279 pages, "Encyclopedia of Chemical Technology", Kirk Othmer, 4th edition (1997), vol. 23, pp. 146-175; "Ullmann's Encyclopedia oflndustrial Chemistry", 5th edition, Elvers, B., Hawkins, S. Schulz, G., (1994), vol. A25, pp. 778-783.
[0044] De manière préférée, l'alcool secondaire utilisé pour synthétiser le composé de formule (I) est choisi parmi le 2-octanol et le méthylisobutylcarbinol, de préférence l'alcool secondaire est le 2-octanol.  Preferably, the secondary alcohol used to synthesize the compound of formula (I) is chosen from 2-octanol and methylisobutylcarbinol, preferably the secondary alcohol is 2-octanol.
[0045] Cet alcool présente un intérêt particulier à plusieurs titres. En effet, il s'agit d'un produit bio-sourcé, biodégradable et présentant un bon profil écotoxicologique. En outre, le point d'ébullition du 2-octanol est élevé et son prix de revient est tout à fait raisonnable.  This alcohol has a particular interest in several ways. Indeed, it is a bio-sourced, biodegradable product with a good ecotoxicological profile. In addition, the boiling point of 2-octanol is high and its cost is quite reasonable.
[0046] Selon un mode de réalisation préféré, l'alcoxylation de l'alcool secondaire utilisé pour synthétiser le composé de formule (I) est obtenu à l'aide d'un catalyseur de type cyanure dimétallique, encore appelé catalyseur DMC. De manière préférée, le catalyseur de type cyanure dimétallique peut être de toute nature connue de l'homme du métier. Ce catalyseur est notamment décrit dans les brevets US6429342, US6977236 et PL398518. Plus particulièrement, le catalyseur utilisé est l'hexacyanocobaltate de zinc, par exemple commercialisé par la Société Bayer sous le nom Arcol® ou encore par la société Mexeo sous la dénomination MEO-DMC®. According to a preferred embodiment, the alkoxylation of the secondary alcohol used to synthesize the compound of formula (I) is obtained using a catalyst of dimetallic cyanide type, also called DMC catalyst. Preferably, the dimetallic cyanide catalyst may be of any type known to those skilled in the art. This catalyst is described in particular in patents US6429342, US6977236 and PL398518. More particularly, the catalyst used is zinc hexacyanocobaltate, for example sold by Bayer under the name Arcol ® or by Mexeo under the name MEO-DMC ® .
[0047] Un autre objet de l'invention est l'utilisation du composé de formule (I) selon l'invention définie précédemment, et/ou un de ses sels, seul ou en mélange, comme agent tensioactif, agent tensio-actif à faible pouvoir moussant, agent de mouillage, agent moussant, hydrotrope, détergent, solvant, solvant réactif, agent de coalescence, compatibilisant, agent émulsifiant, dispersant, intermédiaire chimique, inhibiteur de corrosion, désémulsionnant, plastifiant, séquestrant, inhibiteur de dépôts minéraux, liquide ionique, stabilisant, lubrifiant, additif pour bitumes, additif pour désencrage, agent gélifiant dans les huiles, collecteur de flottation pour les minerais, adjuvant de fabrication dans la manufacture des objets plastiques, agent antistatique, additif pour les revêtements d'engrais, pour la protection des plantes, pour le traitement des textiles et pour la récupération assistée du pétrole, pour la production d'électrodes et d'électrolytes pour batteries, pour ne citer que certaines applications parmi les plus courantes connues pour ce type de composés. Another object of the invention is the use of the compound of formula (I) according to the invention defined above, and / or a salt thereof, alone or as a mixture, as surfactant, surfactant at low foaming power, wetting agent, foaming agent, hydrotrope, detergent, solvent, reactive solvent, coalescing agent, compatibilizer, emulsifying agent, dispersant, chemical intermediate, corrosion inhibitor, demulsifier, plasticizer, sequestering agent, mineral deposit inhibitor, liquid ionic, stabilizer, lubricant, bitumen additive, de-inking additive, gelling agent in oils, flotation collector for ores, processing aids in the manufacture of plastic objects, antistatic agent, additive for fertilizer coatings, for plant protection, for the treatment of textiles and for enhanced oil recovery, for the production of electrodes and electrolytes for batteries, to name only some of the most common applications known for this type of compounds.
[0048] Selon encore un autre objet, la présente invention concerne une composition comprenant au moins un composé de formule (I) tel que défini précédemment, et/ou un de ses sels, seul ou en mélange, avec un ou plusieurs solvants aqueux, organiques, hydroorganiques, tels que par exemple eau, alcools, glycols, polyols, huiles minérales, huiles végétales, et autres, seuls ou en mélanges de deux pu plusieurs d'entre eux, en toutes proportions.  According to yet another object, the present invention relates to a composition comprising at least one compound of formula (I) as defined above, and / or one of its salts, alone or as a mixture, with one or more aqueous solvents, organic, hydroorganic, such as for example water, alcohols, glycols, polyols, mineral oils, vegetable oils, and others, alone or in mixtures of two or more of them, in all proportions.
[0049] La composition selon l'invention peut également contenir un ou plusieurs additifs et charges bien connus de l'homme du métier, tels que par exemple, et à titre non limitatif, tensio-actifs anioniques, cationiques, amphotères, non-ioniques, modificateurs de rhéologie, dés-émulsionnants, agents anti-dépôt, agents anti-mousse, dispersants, agents de contrôle du pH, colorants, anti-oxydants, conservateurs, inhibiteurs de corrosion, biocides, et autres additifs tels que par exemple produits soufrés, borés azotés, phosphatés, et autres. Les natures et quantités des additifs et charges peuvent varier dans de grandes proportions selon la nature de l'application envisagée et pourront facilement être adaptées par l'homme du métier.  The composition according to the invention may also contain one or more additives and fillers well known to those skilled in the art, such as, for example, and without limitation, anionic, cationic, amphoteric, nonionic surfactants. , rheology modifiers, de-emulsifiers, anti-deposition agents, defoamers, dispersants, pH control agents, dyes, antioxidants, preservatives, corrosion inhibitors, biocides, and other additives such as, for example, sulfur-containing products , boreas nitrogenous, phosphates, and others. The nature and amounts of the additives and fillers can vary in large proportions depending on the nature of the application envisaged and can easily be adapted by those skilled in the art.
[0050] L'invention est à présent illustrée par les exemples suivants, qui ne sont nullement limitatifs.  The invention is now illustrated by the following examples, which are in no way limiting.
EXEMPLES EXAMPLES
[0051] Le 2-octanol (CAS RN 123-96-6) utilisé est le 2 octanol Oleris® de grade « Refined » (pureté > 99%), commercialisé par Arkema France. The 2-octanol (CAS RN 123-96-6) used is 2 octanol Oleris ® grade "Refined"(purity> 99%), marketed by Arkema France.
Exemple 1 : Synthèse du sulfate de 2-octanol propoxylé. Example 1 Synthesis of Propoxylated 2-Octanol Sulfate
Étape 1 a : Propoxylation du 2-octanol  Step 1 a: Propoxylation of 2-octanol
[0052] Dans un autoclave de 4 L, propre et sec, on charge 591 g (4,54 mol) de 2-octanol séché à moins de 200 ppm d'eau et 0,06 g (100 ppm) de catalyseur DMC Arcol®. Le réacteur est refermé, purgé à l'azote et l'étanchéité sous pression est vérifiée. On pressurise le réacteur à l'azote sous 0,225 MPa à 27°C. [0053] Le milieu réactionnel est porté à 90°C sous agitation, puis la température est augmentée jusqu'à 120°C. À cette température de 120°C, on introduit 40 g d'oxyde de propylène. Lorsque l'amorçage de la réaction est constaté, on introduit le reste de l'oxyde de propylène, soit en tout 792 g (13,62 M) sur une durée de 60 minutes, à une température de 140-150°C. En fin d'addition, on maintient la température pendant 30 minutes puis on élimine par balayage sous courant d'azote (« stripping ») l'oxyde de propylène résiduel. On refroidit le réacteur à 60°C et on soutire 1381 g de 2-octanol alcoxylé comprenant 3 motifs oxyde de propylène (3 OP). In a clean and dry 4 L autoclave, 591 g (4.54 mol) of dried 2-octanol at less than 200 ppm of water and 0.06 g (100 ppm) of DMC Arcol catalyst are charged. ® . The reactor is closed, purged with nitrogen and the pressure tightness is checked. The reactor is pressurized with nitrogen at 0.225 MPa at 27 ° C. The reaction medium is heated to 90 ° C with stirring, and the temperature is increased to 120 ° C. At this temperature of 120 ° C., 40 g of propylene oxide are introduced. When the initiation of the reaction is observed, the remainder of the propylene oxide is introduced, a total of 792 g (13.62 M) over a period of 60 minutes, at a temperature of 140-150 ° C. At the end of the addition, the temperature is maintained for 30 minutes and then the residual propylene oxide is stripped off under a stream of nitrogen ("stripping"). The reactor is cooled to 60 ° C. and 1381 g of alkoxylated 2-octanol comprising 3 propylene oxide units (3 PO) are withdrawn.
Étape 1 b : Sulfatation du 2-octanol propoxylé Step 1b: Sulfation of propoxylated 2-octanol
[0054] Dans un réacteur agité de 500 cm3 muni d'une agitation, d'une ampoule de coulée à solide et d'un inertage à l'azote, on charge le 2-octanol propoxylé à 3 OP (304 g ; 1 M) obtenu à l'Étape 1 a ci-dessus. On porte à 1 10°C sous agitation et barbotage d'azote. On vérifie par dosage la teneur en eau qui doit être inférieure à 2500 ppm. On porte ensuite la température à 130°C et on commence à introduire l'acide sulfamique (101 ,5 g ; 1 ,05 M). La vitesse d'introduction est gérée pour maintenir une température de 130°C. On laisse ensuite sous agitation pendant 1 heure à 130°C. In a stirred reactor of 500 cm 3 provided with stirring, a solid casting funnel and a nitrogen inerting, the propoxylated 2-octanol is charged with 3 OP (304 g; M) obtained in Step 1a above. It is heated to 110 ° C. with stirring and bubbling with nitrogen. The water content, which must be less than 2500 ppm, is tested by metering. The temperature is then raised to 130 ° C. and the sulphamic acid (101.5 g; 1.05 M) is introduced. The feed rate is managed to maintain a temperature of 130 ° C. It is then left stirring for 1 hour at 130 ° C.
[0055] On refroidit ensuite à 70°C. On ajoute ensuite goutte à goutte une solution aqueuse ammoniacale 0,05 M, de façon à neutraliser l'excès d'acide sulfamique. On vidange ensuite en flacon. On récupère 390 g de produit.  Then cooled to 70 ° C. A 0.05 M aqueous ammonia solution is then added dropwise so as to neutralize the excess of sulfamic acid. We then empty in a bottle. 390 g of product are recovered.
Exemple 2 : sulfate de 2-octanol éthoxylé Example 2: Ethoxylated 2-octanol sulphate
Étape 2a : éthoxylation du 2-octanol  Step 2a: ethoxylation of 2-octanol
[0057] Dans un autoclave de 4L, propre et sec, on charge 619 g (4,76 M) de 2-octanol séché à moins de 200 ppm d'eau et 0,06 g (100 ppm) de catalyseur DMC Arcol®. Le réacteur est refermé, purgé à l'azote et l'étanchéité sous pression est vérifiée. On pressurise le réacteur à l'azote sous 0,269 MPa à 20°C. In a 4L autoclave, clean and dry, 619 g (4.76M) of dried 2-octanol are charged to less than 200 ppm of water and 0.06 g (100 ppm) of Arcol ® DMC catalyst. . The reactor is closed, purged with nitrogen and the pressure tightness is checked. The reactor is pressurized with nitrogen at 0.269 MPa at 20 ° C.
[0058] Le milieu réactionnel est porté à 120°C sous agitation. À cette température de 120°C, on introduit 40 g d'oxyde d'éthylène. Lorsque l'amorçage de la réaction est constaté, on introduit le reste de l'oxyde d'éthylène soit en tout 628 g (14,27 M) pendant 60 minutes à une température de 140-150°C. En fin d'addition, on maintient la température pendant 30 minutes, puis on strippe à l'azote l'oxyde d'éthylène résiduel. On refroidit le réacteur à 60°C et on soutire 1240 g de 2-octanol alcoxylé comprenant 3 motifs oxyde d'éthylène. (IOH : 210 mg de KOH/g et coloration de 26 Hz). The reaction medium is heated to 120 ° C with stirring. At this temperature of 120 ° C., 40 g of ethylene oxide are introduced. When the initiation of the reaction is noted, the remainder of the ethylene oxide is fed in a total of 628 g (14.27 M) for 60 minutes at a temperature of 140-150 ° C. At the end of the addition, the temperature is kept 30 minutes, then stripped with nitrogen the residual ethylene oxide. The reactor is cooled to 60 ° C. and 1240 g of alkoxylated 2-octanol comprising 3 ethylene oxide units are withdrawn. (IOH: 210 mg KOH / g and 26 Hz staining).
Étape 2b : sulfatation du 2-octanol éthoxylé Step 2b: sulfation of ethoxylated 2-octanol
[0059] Dans un réacteur de 500 cm3, sous atmosphère d'azote, on charge 262 g (1 M) de 2-octanol éthoxylé obtenu à l'Étape 2a, puis 1 16 g (1 M) d'acide chlorosulfonique sont alors ajoutés goutte à goutte sous agitation. L'addition d'acide chlorosulfonique est réalisée tout en contrôlant la température qui ne doit pas dépasser 30°C. À la fin de l'addition, la température du réacteur est maintenue à 30°C pendant 20 minutes sous agitation. L'acide chlorhydrique est éliminé en continu par un barbotage d'azote dans le milieu réactionnel. In a 500 cm 3 reactor, under a nitrogen atmosphere, 262 g (1 M) of ethoxylated 2-octanol obtained in Step 2a are charged and then 16 g (1 M) of chlorosulphonic acid are added. then added dropwise with stirring. The addition of chlorosulfonic acid is carried out while controlling the temperature which should not exceed 30 ° C. At the end of the addition, the temperature of the reactor is maintained at 30 ° C for 20 minutes with stirring. Hydrochloric acid is removed continuously by sparging nitrogen into the reaction medium.
[0060] La réaction est suivie par la quantité d'acide chlorhydrique produit. Il est considéré que la réaction est terminée lorsque les valeurs ne varient pas. On récupère environ 340 g de sulfate de 2-octanol alcoxylé comprenant 3 motifs oxyde d'éthylène (3 OE). The reaction is followed by the amount of hydrochloric acid produced. It is considered that the reaction is complete when the values do not vary. About 340 g of alkoxylated 2-octanol sulphate comprising 3 ethylene oxide units (3 EO) are recovered.
Exemple 3 : Salification avec l'hydroxyde de sodium Example 3 Salification with Sodium Hydroxide
[0062] Dans un réacteur de 1 L, on charge 342 g (1 M) du sulfate de 2-octanol éthoxylé obtenu comme décrit précédemment (exemple 4). Sont ajoutés ensuite 80 g (2 M) d'hydroxyde de sodium sous agitation. À la fin de l'addition, la température du réacteur est maintenue à 60°C pendant 15 minutes sous agitation. Le réacteur est ensuite refroidi et le produit est isolé.  In a 1 L reactor, 342 g (1 M) of ethoxylated 2-octanol sulfate obtained as described above (Example 4). 80 g (2 M) of sodium hydroxide are then added with stirring. At the end of the addition, the reactor temperature is maintained at 60 ° C for 15 minutes with stirring. The reactor is then cooled and the product is isolated.
[0063] On récupère environ 380 g du sel de sodium du sulfate de 2-octanol alcoxylé comprenant 3 motifs oxyde d'éthylène.  About 380 g of the sodium salt of alkoxylated 2-octanol sulphate comprising 3 ethylene oxide units are recovered.
Exemple 4 : Salification avec une amine grasse Example 4 Salification with a fatty amine
[0064] Dans un réacteur de 1 L, on charge 342 g (1 M) du sulfate de 2-octanol éthoxylé obtenu à l'exemple 2 comme décrit précédemment. Le réacteur est chauffé à 80°C, puis 259 g (1 M) d'une amine grasse comportant une chaîne d'environ 18 atomes de carbone commercialisée par Arkema France sous le nom de NORAM SH® sont alors ajoutés sous agitation, tout en contrôlant la température qui ne doit pas dépasser 80°C. À la fin de l'addition, la température du réacteur est maintenue à 80°C pendant 15 minutes sous agitation. Le réacteur est ensuite refroidi et le produit synthétisé est récupéré. In a 1 L reactor, 342 g (1 M) of 2-octanol sulfate ethoxylated obtained in Example 2 as described above. The reactor was heated to 80 ° C, then 259 g (1 M) of a fatty amine having a chain of about 18 carbon atoms sold by Arkema France under the name of Noram ® SH are then added with stirring, while controlling the temperature which should not exceed 80 ° C. At the end of the addition, the temperature of the reactor is maintained at 80 ° C for 15 minutes with stirring. The reactor is then cooled and the synthesized product is recovered.
[0065] On récupère ainsi environ 600 g du sel d'amine grasse du sulfate de 2-octanol alcoxylé comprenant 3 motifs oxyde d'éthylène. About 600 g of the fatty amine salt of the alkoxylated 2-octanol sulphate comprising 3 ethylene oxide units are thus recovered.

Claims

REVENDICATIONS
1. Composé de formule (I) suivante : dans laquelle : 1. Compound of formula (I) below: in which :
- les groupements Ri et R2, identiques ou différents, représentent, indépendamment l'un de l'autre, un groupement hydrocarboné linéaire, ramifié ou cyclique, saturé ou insaturé, comprenant de 1 à 6 atomes de carbone, étant entendu que la somme des atomes de carbone des groupements Ri et R2 va de 2 à 7, Ri et R2 pouvant former ensemble et avec l'atome de carbone qui les porte, un cycle à 6, 7 ou 8 sommets,  the groups R 1 and R 2, which are identical or different, represent, independently of one another, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group comprising from 1 to 6 carbon atoms, it being understood that the sum of carbon atoms of the groups R 1 and R 2 is from 2 to 7, R 1 and R 2 may form, together with the carbon atom carrying them, a ring with 6, 7 or 8 vertices,
- A représente un enchaînement d'un ou plusieurs motifs choisis parmi les motifs oxyde d'éthylène, oxyde de propylène, oxyde de butylène et leurs mélanges, et  A represents a sequence of one or more units chosen from ethylene oxide, propylene oxide and butylene oxide units and mixtures thereof, and
- n est un nombre entier compris entre, bornes incluses, 1 et 100, de préférence entre 2 et 100, de préférence encore entre 3 et 100, plus particulièrement entre 5 et 100, et de manière très préférée entre 10 et 100.  n is an integer between, inclusive, 1 and 100, preferably between 2 and 100, more preferably between 3 and 100, more preferably between 5 and 100, and most preferably between 10 and 100.
2. Composé selon la revendication 1 , sous forme de sel avec un cation alcalin, un cation alcalino-terreux, un cation métallique ou avec un composé organique, incluant les bases organiques. 2. A compound according to claim 1, in salt form with an alkaline cation, an alkaline earth cation, a metal cation or with an organic compound, including organic bases.
3. Composé selon la revendication 1 ou la revendication 2, dans lequel les groupements Ri et R2, identiques ou différents, sont choisis, indépendamment l'un de l'autre, parmi les radicaux méthyle, éthyle, n-propyle, /'so-propyle, n-butyle, sec-butyle, ie/f-butyle, pentyles, et hexyles. 3. A compound according to claim 1 or claim 2, wherein Ri and R2, identical or different, are chosen, independently of each other, from methyl, ethyl, n-propyl, / 'so propyl, n-butyl, sec-butyl, β-butyl, pentyles, and hexyls.
4. Composé selon l'une quelconque des revendications 1 à 3, dans lequel le radical formé par Ri, R2 et l'atome de carbone auquel ils sont rattachés, est choisi parmi le radical 2-octyle et le radical 4-méthyl-2-pentyle, de préférence le radical formé par Ri, R2 et l'atome de carbone auquel ils sont rattachés est le radical 2-octyle. 4. Compound according to any one of claims 1 to 3, wherein the radical formed by R 1, R 2 and the carbon atom to which they are attached is chosen from the 2-octyl radical and the 4-methyl-2 radical. -pentyl, preferably the radical formed by R 1, R 2 and the carbon atom to which they are attached is the 2-octyl radical.
5. Composé selon l'une quelconque des revendications 1 à 4, dans lequel n est compris entre, bornes incluses, 1 et 75, de préférence entre 2 et 75, de préférence encore entre 3 et 75, plus particulièrement entre 5 et 75, et de manière très préférée entre 10 et 75. 5. Compound according to any one of claims 1 to 4, wherein n is between, inclusive, 1 and 75, preferably between 2 and 75, more preferably between 3 and 75, more particularly between 5 and 75, and very preferably between 10 and 75.
6. Composé selon l'une quelconque des revendications 1 à 5, dans lequel n est compris entre, bornes incluses, 1 et 50, de préférence entre 2 et 50, de préférence encore entre 3 et 50, plus particulièrement entre 5 et 50, et de manière très préférée entre 10 et 50. 6. Compound according to any one of claims 1 to 5, wherein n is between, inclusive, 1 and 50, preferably between 2 and 50, more preferably between 3 and 50, more particularly between 5 and 50, and very preferably between 10 and 50.
7. Composé selon l'une quelconque des revendications 1 à 5, dans lequel le groupe formé par Ri, F¾ et l'atome de carbone auquel ils sont rattachés représente le radical 2-octyle, n va de 3 à 15, et A représente un enchaînement d'un ou plusieurs motifs choisis parmi les motifs oxyde d'éthylène, oxyde de propylène, oxyde de butylène et leurs mélanges. A compound according to any one of claims 1 to 5, wherein the group formed by R 1, F¾ and the carbon atom to which they are attached represents the 2-octyl radical, n is from 3 to 15, and A represents a sequence of one or more units selected from ethylene oxide units, propylene oxide, butylene oxide and mixtures thereof.
8. Sel du composé selon l'une quelconque des revendications 1 à 7, répondant à la formule (II) suivante : 8. Salt of the compound according to any one of claims 1 to 7, corresponding to the following formula (II):
dans laquelle ; in which ;
- Mx+ représente un groupement cationique porteur d'au moins un cation choisi parmi cation ammonium, cation métallique, cation azoté, cation boré, cation phosphoré,- M x + represents a cationic group bearing at least one cation selected from ammonium cation, metal cation, nitrogen cation, boron cation, phosphorus cation,
- x est un nombre entier allant de 1 à 7, et x is an integer ranging from 1 to 7, and
- Ri, R2, A et n étant tels que définis dans l'une quelconque des revendications 1 à 7.  R 1, R 2, A and n being as defined in any one of claims 1 to 7.
9. Utilisation d'un composé selon l'une quelconque des revendications précédentes, comme agent tensioactif, agent tensio-actif à faible pouvoir moussant, agent de mouillage, agent moussant, hydrotrope, détergent, solvant, solvant réactif, agent de coalescence, compatibilisant, agent émulsifiant, dispersant, intermédiaire chimique, inhibiteur de corrosion, désémulsionnant, plastifiant, séquestrant, inhibiteur de dépôts minéraux, liquide ionique, stabilisant, lubrifiant, additif pour bitumes, additif pour désencrage, agent gélifiant dans les huiles, collecteur de flottation pour les minerais, adjuvant de fabrication dans la manufacture des objets plastiques, agent antistatique, additif pour les revêtements d'engrais, pour la protection des plantes, pour le traitement des textiles et pour la récupération assistée du pétrole, pour la production d'électrodes et d'électrolytes pour batteries. 9. Use of a compound according to any one of the preceding claims, as surfactant, low foaming surfactant, wetting agent, foaming agent, hydrotrope, detergent, solvent, reactive solvent, coalescing agent, compatibilizer , emulsifying agent, dispersant, chemical intermediate, corrosion inhibitor, demulsifier, plasticizer, sequestering agent, mineral deposit inhibitor, ionic liquid, stabilizer, lubricant, bitumen additive, deinking additive, gelling agent in oils, flotation collector for minerals, processing aids in the manufacture of plastic objects, anti-static agent, additive for fertilizer coatings, plant protection, textile treatment and enhanced oil recovery , for the production of electrodes and electrolytes for batteries.
10. Composition comprenant au moins un composé de formule (I) et/ou un de ses sels, seul ou en mélange, tel que défini à l'une quelconque des revendications 1 à 8, avec un ou plusieurs solvants aqueux, organiques, hydro-organiques, et éventuellement un ou plusieurs additifs et charges. 10. Composition comprising at least one compound of formula (I) and / or a salt thereof, alone or as a mixture, as defined in any one of claims 1 to 8, with one or more aqueous, organic, hydro-organic solvents. -organics, and optionally one or more additives and fillers.
EP18821707.9A 2017-11-10 2018-11-08 Alkoxylated secondary alcohol sulfates Pending EP3707123A1 (en)

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