EP3707123A1 - Sulfates d'alcools secondaires alcoxylés - Google Patents

Sulfates d'alcools secondaires alcoxylés

Info

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
Other languages
German (de)
English (en)
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
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Arkema France SA filed Critical Arkema France SA
Publication of EP3707123A1 publication Critical patent/EP3707123A1/fr
Pending legal-status Critical Current

Links

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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Detergent Compositions (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
EP18821707.9A 2017-11-10 2018-11-08 Sulfates d'alcools secondaires alcoxylés Pending EP3707123A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1760597A FR3073517A1 (fr) 2017-11-10 2017-11-10 Sulfates d'alcools secondaires alcoxyles
PCT/FR2018/052763 WO2019092368A1 (fr) 2017-11-10 2018-11-08 Sulfates d'alcools secondaires alcoxylés

Publications (1)

Publication Number Publication Date
EP3707123A1 true EP3707123A1 (fr) 2020-09-16

Family

ID=62091941

Family Applications (1)

Application Number Title Priority Date Filing Date
EP18821707.9A Pending EP3707123A1 (fr) 2017-11-10 2018-11-08 Sulfates d'alcools secondaires alcoxylés

Country Status (11)

Country Link
US (2) US11339123B2 (zh)
EP (1) EP3707123A1 (zh)
JP (1) JP7042339B2 (zh)
KR (1) KR102339199B1 (zh)
CN (1) CN111263748A (zh)
BR (1) BR112020008411A2 (zh)
CA (1) CA3079986C (zh)
FR (1) FR3073517A1 (zh)
MX (1) MX2020004267A (zh)
SG (1) SG11202003897PA (zh)
WO (1) WO2019092368A1 (zh)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3073517A1 (fr) * 2017-11-10 2019-05-17 Arkema France Sulfates d'alcools secondaires alcoxyles
FR3102177B1 (fr) * 2019-10-18 2023-05-19 Arkema France Alcools alcoxylés et coiffés
CN115010916B (zh) * 2020-12-31 2024-02-09 山东金智瑞新材料发展有限公司 一种脂肪醇聚氧丙烯醚含氧酸及其盐、制备方法和应用
WO2024088716A1 (en) * 2022-10-25 2024-05-02 Unilever Ip Holdings B.V. Composition

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Publication number Publication date
BR112020008411A2 (pt) 2020-10-06
JP2021502369A (ja) 2021-01-28
KR20200061404A (ko) 2020-06-02
MX2020004267A (es) 2020-08-06
FR3073517A1 (fr) 2019-05-17
SG11202003897PA (en) 2020-05-28
WO2019092368A1 (fr) 2019-05-16
CA3079986C (fr) 2023-01-17
CN111263748A (zh) 2020-06-09
US20210403422A1 (en) 2021-12-30
CA3079986A1 (fr) 2019-05-16
US20200361862A1 (en) 2020-11-19
US11718581B2 (en) 2023-08-08
JP7042339B2 (ja) 2022-03-25
KR102339199B1 (ko) 2021-12-13
US11339123B2 (en) 2022-05-24

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