WO2023018326A1 - Synthèse d'alkyltriazoleglycoside (atg) pour application de type huile dans l'eau - Google Patents

Synthèse d'alkyltriazoleglycoside (atg) pour application de type huile dans l'eau Download PDF

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Publication number
WO2023018326A1
WO2023018326A1 PCT/MY2022/050071 MY2022050071W WO2023018326A1 WO 2023018326 A1 WO2023018326 A1 WO 2023018326A1 MY 2022050071 W MY2022050071 W MY 2022050071W WO 2023018326 A1 WO2023018326 A1 WO 2023018326A1
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formula
compound
group
sugar
linear
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PCT/MY2022/050071
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English (en)
Inventor
Navin Sharma KARAM CHAND
Jofry OTHMAN
Normawati SAMSODIN
Thorsten Heidelberg
Su-Han NG
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Petroliam Nasional Berhad (Petronas)
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Publication of WO2023018326A1 publication Critical patent/WO2023018326A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives

Definitions

  • the invention relates to compounds of formula (I) and (II), compositions comprising the compounds, uses of these compounds as surfactants, and to methods for their production.
  • Carbohydrate based surfactants are an important class of surfactant and are useful in a diverse range of industrial applications, such as: enhanced oil recovery; pharmaceutical products; personal care compositions; and household or industrial cleaning.
  • Carbohydrate based surfactants are bio-sourced, inexpensive, green, nontoxic and may be tailored to a specific use by modifying their morphology.
  • carbohydrate based surfactants are the alkyl polyglucosides (APGs), which typically have a degree of polymerisation of about 1.5, with a maximum of about 1.8.
  • APGs alkyl polyglucosides
  • the number of sugar units in an APG never reaches 2.
  • a higher sugar content would enhance the interaction between the surfactant and water, which would help overcome the dominating hydrophobic behaviour of APGs, which would be favourable for applications such as personal care products and household cleaning products.
  • carbohydrate based surfactants that can be tailored to have dominant hydrophilic or hydrophobic behaviour, especially carbohydrate based surfactants that have increased hydrophilicity as compared to alkyl polyglucosides.
  • carbohydrate based surfactants that may be synthesised easily with high yields without solubility or miscibility issues.
  • carbohydrate based surfactants may be quickly and easily prepared from readily available starting materials using an azide-alkyne click chemistry approach.
  • a surfactant comprising two sugar moieties arranged in a side-by-side (Y-shaped) configuration advantageously increases the sugar-water interaction as compared to a surfactant comprising a disaccharide arranged in a linear (series) configuration (Fig. 1(a)).
  • the surfactants of the invention i.e. compounds of formula (I) or (II)
  • the surfactants of the invention comprise a hydrophobic tail connected to the rest of the molecule (e.g. via an ether linkage). This linkage advantageously allows compounds of formula (I) or (II) to be prepared more quickly, efficiently and economically from simple starting materials obtained from renewable resources, and under more environmentally friendly reaction conditions, as compared to similar molecules that do not comprise an ether linkage in this position.
  • the current invention provides compounds that may be synthesised with fewer chemical steps and without using complex and expensive hydride reductions (e.g of malonic esters to alcohols).
  • the invention provides the following numbered clauses. 1.
  • R is selected from the group consisting of a linear or branched C 6-20 alkyl chain, and a linear or branched C 6-20 alkenyl chain that may be mono-, di- or tri-unsaturated;
  • X 1 represents H or –CH 2 -Y;
  • X 2 represents H or –CH 2 -Y; provided that for each triazole moiety, one of X 1 and X 2 is H and the other is -CH 2 -Y; each Y is independently selected from the group consisting of a hexose sugar, a pentose sugar, a hexuronic acid, a 2-amino hexose sugar, a disaccharide and an oligosaccharide, where each Y is bonded to the rest of the molecule via an O- glycosidic bond.
  • each Y is independently selected from the group consisting of a hexose sugar and a pentose sugar, optionally wherein each Y is a hexose sugar.
  • each Y is independently selected from the group consisting of glucose, mannose, galactose, and xylose, optionally wherein each Y is independently selected from the group consisting of glucose, mannose, and galactose.
  • each Y is the same. 5.
  • R is selected from the group consisting of a linear or branched C 8-16 alkyl chain, and a linear or branched C 8-16 alkenyl chain that may be mono- or di-unsaturated. 7. A compound according to any one of the preceding clauses, wherein R is selected from the group consisting of a linear or branched C 10-14 alkyl chain, and a linear or branched C 10-14 alkenyl chain that may be mono- or di-unsaturated, optionally wherein R represents a C 10-12 linear alkyl chain.
  • R represents a linear or branched alkyl chain, optionally wherein R represents a linear alkyl chain.
  • R represents: (a) a moiety formed by removing a hydrogen atom from an acyclic monoterpene; or (b) a moiety formed by removing a hydroxyl group from an acyclic monoterpene alcohol.
  • each X 1 is the same and each X 2 is the same.
  • each X 1 is -CH 2 -Y and each X 2 is H. 12.
  • a compound according to any one of the preceding clauses which is of formula (I). 13. A compound according to any one of Clauses 1 to 11, which is of formula (II). 14. A compound according to any one of Clauses 1 to 12, which is a compound of formula (I) having the formula (Ia) or (Ib):
  • a surfactant composition comprising: (i) a compound of formula (I); and/or (ii) a compound of formula (II), wherein the compound of formula (I) and compound of formula (II) are each as defined in any one of the preceding clauses. 17. Use of a compound according to any one of Clauses 1 to 15, or a composition according to Clause 14, as a surfactant. 18.
  • a method of stabilising an oil-in-water emulsion comprising the steps: (a) providing an oil-in-water emulsion; and (b) contacting the oil-in-water emulsion with an effective amount of a compound according to any one of Clauses 1 to 15, or a composition according to Clause 16, so as to stabilise the emulsion. 19.
  • step (iii) when Z represents a protected sugar moiety, performing a deprotecting step to provide a compound of formula (I) or (II) in which Y is not a protected sugar, optionally wherein in step (ii), Z represents an unprotected sugar moiety as defined for moiety Y in Clause 1. 20.
  • the metal catalyst is selected from the group consisting of a Cu(I) catalyst, a Ru(II) catalyst and a Ag(I) catalyst, optionally wherein the metal catalyst is selected from the group consisting of a Cu(I) catalyst, and a Ru(II) catalyst, more optionally wherein the metal catalyst is a Cu(I) catalyst. 21.
  • BRIEF DESCRIPTION OF THE FIGURES Fig.1 shows two possible configurations for a surfactant comprising two sugar moieties and a hydrophobic tail.
  • Fig.2 shows a synthetic route for formation of a compound of formula (Ia).
  • Fig.3 shows a synthetic route for formation of a compound of formula (IIa).
  • Fig. 4 shows the general structure of alkyl polyglucoside (APG) and alkyl triazole glycoside (ATG).
  • APG alkyl polyglucoside
  • AGT alkyl triazole glycoside
  • DETAILED DESCRIPTION As explained above, the carbohydrate based surfactants of the invention may be quickly and easily prepared from readily available starting materials using an azide-alkyne click chemistry approach.
  • the surfactants of the invention comprise two sugar moieties arranged in a side- by-side (Y-shaped) configuration as shown in Fig.1(b), which advantageously increases the sugar-water interaction, and may be associated with lower skin irritation.
  • the surfactants of the invention i.e. compounds of formula (I) or (II)
  • a compound of formula (I) or (II) wherein R is selected from the group consisting of a linear or branched C 6-20 alkyl chain, and a linear or branched C 6-20 alkenyl chain that may be mono-, di- or tri-unsaturated;
  • X 1 represents H or –CH 2 -Y;
  • X 2 represents H or –CH 2 -Y; provided that for each triazole moiety, one of X 1 and X 2 is H and the other is -CH 2 -Y;
  • each Y is independently selected from the group consisting of a hexose sugar, a pentose sugar, a hexuronic acid, a 2-amino hexose sugar, a disaccharide and an oligosaccharide, where each Y is bonded to the rest of the molecule via an O-glycosidic bond.
  • the word “comprising” refers herein may be interpreted as requiring the features mentioned, but not limiting the presence of other features. Alternatively, the word “comprising” may also relate to the situation where only the components/features listed are intended to be present (e.g. the word “comprising” may be replaced by the phrases “consists of” or “consists essentially of”). It is explicitly contemplated that both the broader and narrower interpretations can be applied to all aspects and embodiments of the present invention. In other words, the word “comprising” and synonyms thereof may be replaced by the phrase “consisting of” or the phrase “consists essentially of” or synonyms thereof and vice versa.
  • the phrase, “consists essentially of” and its pseudonyms may be interpreted herein to refer to a material where minor impurities may be present.
  • the material may be greater than or equal to 90% pure, such as greater than 95% pure, such as greater than 97% pure, such as greater than 99% pure, such as greater than 99.9% pure, such as greater than 99.99% pure, such as greater than 99.999% pure, such as 100% pure.
  • 90% pure such as greater than 95% pure, such as greater than 97% pure, such as greater than 99% pure, such as greater than 99.9% pure, such as greater than 99.99% pure, such as greater than 99.999% pure, such as 100% pure.
  • R may be selected from the group consisting of a linear or branched C 6-20 alkyl chain, and a linear or branched C 6-20 alkenyl chain that may be mono-, di- or tri-unsaturated.
  • R may be a linear or branched C 6-20 alkyl chain, and may optionally be a linear or branched C 8-16 alkyl chain, for example a linear or branched C 10-14 alkyl chain, such as a linear C 10-12 alkyl chain.
  • R may be a linear alkyl chain, e.g. R may be a linear C 6-20 alkyl chain, a linear C 8-16 alkyl chain, a linear C 10-14 alkyl chain or a linear C 10-12 alkyl chain.
  • R may be a linear or branched C 6-20 alkenyl chain that may be mono-, di- or tri-unsaturated.
  • R may be a linear or branched C 8-16 alkenyl chain that may be mono- or di-unsaturated, for example a linear or branched C 10-14 alkenyl chain that may be mono- or di-unsaturated.
  • R may be a moiety formed by removing a hydrogen atom from an acyclic monoterpene, or R may be a moiety formed by removing a hydroxyl group from an acyclic monoterpene alcohol.
  • R may be a moiety formed by removing a hydroxyl group from an acyclic monoterpene alcohol, such as a moiety formed by removing a hydroxyl group from nerol or geraniol.
  • Nerol Geraniol In some embodiments of the invention, R may be a branched alkyl chain that corresponds to a hydrogenated version of the alkenyl groups mentioned above.
  • R may be a chain formed by the hydrogenation of an acyclic monoterpene, for example a 3,7-dimeythyloctyl group formed by hydrogenating the carbon chain of nerol or geraniol.
  • X 1 and X 2 each represent H or –CH 2 -Y, provided that for each triazole moiety, one of X 1 and X 2 is H and the other is -CH 2 -Y.
  • said “triazole moiety” refers to the two moieties having the formula: within each of formulae (I) and (II).
  • each X 1 may be the same, and each X 2 may be the same.
  • each X 1 will generally be the same, and each X 2 will generally be the same.
  • the reaction to form the triazole ring is, depending on the catalyst used, generally selective for either a 1,4-triazole or a 1,5-triazole.
  • the formation of the triazole rings in the compounds of formula (I) and (II) will usually result in predominantly the 1,4-triazole or predominantly the 1,5-triazole.
  • the compounds of formula (I) or (II) are prepared from a single Azide-alkyne Huisgen cycloaddition, the product will typically have each X 1 being the same, and each X 2 being the same.
  • a Cu(I) or Ag(I) catalyst will provide predominantly the 1,4-triazole (i.e.
  • each X 1 is -CH 2 -Y and each X 2 is H
  • Ru(II) catalyst will provide predominantly the 1,5-triazole (i.e. where each X 1 is H and each X 2 is -CH 2 -Y).
  • each X 1 may be -CH 2 -Y and each X 2 may be H.
  • each X 1 may be H and each X 2 may be -CH 2 -Y.
  • each Y may be independently selected from the group consisting of a hexose sugar, a pentose sugar, a hexuronic acid, a 2-amino hexose sugar, a disaccharide and an oligosaccharide, where each Y may be bonded to the rest of the molecule (i.e. the -CH 2 - moiety within X 1 and X 2 ) via an O-glycosidic bond.
  • hexose sugars that may be mentioned herein include glucose, mannose, and galactose.
  • An example of a pentose sugar that may be mentioned herein is xylose.
  • each Y may be independently selected from the group consisting of a hexose sugar and a pentose sugar, optionally wherein each Y may be a hexose sugar.
  • each Y may be independently selected from the group consisting of glucose, mannose, galactose, and xylose, optionally wherein each Y may be independently selected from the group consisting of glucose, mannose, and galactose.
  • each Y may be the same.
  • each Y represents glucose.
  • the compound of formula (I) or (II) may be a compound of formula (I).
  • the compound of formula (I) or (II) may be a compound of formula (II).
  • Specific compounds according to the invention include compounds of formula (Ia), (Ib), (IIa) and (IIb) below.
  • references to compounds of formula (I) and/or (II) herein include, where permitted by context, references to compounds of formula (Ia), (Ib), (IIa) and (IIb).
  • the invention provides a surfactant composition comprising a compound of formula (I) and/or a compound of formula (II), as described herein.
  • the compounds of formula (I) and/or (II) disclosed herein, and compositions comprising them, may be used as surfactants.
  • the invention also provides the use of a compound of formula (I) and/or (II) disclosed herein, or the use of compositions comprising a compound of formula (I) and/or (II) disclosed herein, as a surfactant.
  • the invention provides a method of stabilising an oil-in-water emulsion comprising the steps: (a) providing an oil-in-water emulsion; and (b) contacting the oil-in-water emulsion with an effective amount of a compound of formula (I) and/or (II), or a composition comprising a compound of formula (I) and/or (II), so as to stabilise the emulsion.
  • the invention also provides methods for making a compound of formula (I) and/or (II).
  • the invention provides a method of making a compound of formula (I) or (II), comprising the steps: (i) providing a compound of formula (Ip) or (IIp) (Ip) (IIp); (ii) reacting the compound of formula (Ip) or (IIp) with a compound of formula (III) in the presence of a metal catalyst (III) wherein in formula (III), Z represents a sugar moiety as defined for moiety Y above, or a protected version thereof (e.g.
  • the metal catalyst in this reaction may be selected from the group consisting of a Cu(I) catalyst, a Ru(II) catalyst and a Ag(I) catalyst.
  • the metal catalyst may be selected from the group consisting of a Cu(I) catalyst, and a Ru(II) catalyst.
  • the metal catalyst may be a Cu(I) catalyst.
  • the method of making a compound of formula (I) and/or (II) may further comprise steps of making the precursor compounds.
  • the method further comprises forming the compound of formula (Ip) by the steps: (a) reacting a compound of formula (IV) with NaN 3 to form a compound of formula (Ipp) (IV) (Ipp); and (b) reacting the compound of formula (Ipp) with a with a compound of formula R-X, where X is a leaving group (such as a halide, e.g. Br), to form a compound of formula (Ip).
  • X is a leaving group (such as a halide, e.g. Br)
  • the method may further comprise forming the compound of formula (IIp) by the steps: (a) reacting a compound of formula (V) with a compound of formula R-OH to form a compound of formula (VI) (V) (VI); (b) reacting the compound of formula (VI) with Cl 2 to form a compound of formula (IIpp) (IIpp); and (c) reacting the compound of formula (IIpp) with NaN3 to form the compound of formula (IIp).
  • This synthetic route to form a compound of formula (II) is shown in Fig.3. Also disclosed herein are compounds of Formula (X) and (XI).
  • X 1 and X 2 are the same as in embodiments disclosed herein, and R 0 represents a linear or branched C5-20 alkyl chain.
  • Compounds of formula (X) and (XI) may be made by analogous methods to compounds of formula (I) and (II), from precursors of formula (Xp) and (XIp), respectively: (Xp) (XIp)
  • Compounds of formula (Xp) and (XIp) may be prepared from compounds of the formula: where X represents a leaving group, such as a halogen (e.g. chlorine).
  • the invention provides a compound of formula (X).
  • the invention provides a compound of formula (XI). In some embodiments, the invention provides a method of preparing a compound of formula (X), as disclosed above. In some embodiments, the invention provides a method of preparing a compound of formula (XI), as disclosed above.
  • the invention is illustrated by the below Examples, which are not to be construed as limitative. EXAMPLES Example 1: Preparation of the surfactant compounds Compounds of formula (I) and (II) may be made by different synthetic routes. Formula (I)
  • the compounds of the invention may be prepared from sugar moieties that do not comprise protecting groups (i.e when R in the above schemes represents H), such as from sugar moieties prepared using the Fischer glycosidation.
  • protecting groups i.e when R in the above schemes represents H
  • a skilled person would appreciate that avoiding the use of protecting groups may provide a more economical production method, since fewer steps are involved.
  • Precursor (3) 0.5 g, 1.61 mmol
  • peracetylated propargyl glucose (0.92 g, 3.22 mmol) were coupled with copper (II) salt (Cu(OAc)2) (0.04 g, 0.24 mmol) and Na- ascorbate (0.14 g, 0.72 mmol) in MeOH (50 mL) according to the general procedure I.
  • Chromatographic purification was applied using EtOAc – Hexane mixture at a ratio of 2:3 and final product of light yellow appearance was obtained with a yield of 73.21%.
  • reaction mixture was filtered to remove the used resin and concentrated in vacuo to remove unreacted propargyl alcohol.
  • the residue was co- evaporated with water to remove traces of propargyl alcohol.
  • the residue was dissolved in methanol, to which 2.0 g charcoal powder was added and placed in a sonication bath briefly to remove dark coloured impurities.
  • the mixture was filtered and concentrated in vacuo to dryness. Drying over P2O5 in a vacuum desiccator furnished 10.16 g (46.56 mmol, 83.9%) of a clear amber gel.
  • Example 2 Comparison of surfactant properties Surfactant properties for various surfactants are shown in Table 1 below. General structures of APG and ATG are shown in Fig.4, where the circle represents a sugar moiety and pentagon represents a triazole moiety. These differ from compounds of formula (I) and (II) at least in that they comprise only a single sugar moiety. NP-9 and NP-10 are commercially available surfactant compositions based on nonylphenol ethoxylate.
  • the surfactants of the invention have an advantageously low surface tension.
  • the molecular surface area is also advantageously low, which is believed to be advantageous for applications such as templating (e.g. cavities in porous materials or 2-phase synthesis of nanoparticles).
  • Example 3 Stability test Oil-in-water emulsions were prepared using a 19:1 ratio of water and oil containing 0.5% (wt/vol) of a surfactant. Three types of oil were used for the emulsion stability test: ethyl laurate, methyl laurate and paraffin oil. The formulation was mixed with a homogenizer for 2 mins at room temperature at a speed of 14,450 rpm.
  • Reference compound 17 Reference compound 25: Reference compound 26: Reference compound 27: The results show the surfactant of formula (Ia) provided stable emulsions that required several days to phase separate. This emulsion stability substantially exceeded that for the single head C12-ATG surfactant (compound 27). This confirms the improved emulsion performance obtained by introducing a second sugar head group to the surfactant.
  • the surfactants of the invention have comparable activity to reference compound 25, whilst being much cheaper and easier to synthesise.

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  • Health & Medical Sciences (AREA)
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Abstract

L'invention concerne des composés de formule (I) et (II), qui sont utiles en tant que tensioactifs. L'invention concerne également des procédés de préparation de composés de formule (I) et (II).
PCT/MY2022/050071 2021-08-13 2022-08-12 Synthèse d'alkyltriazoleglycoside (atg) pour application de type huile dans l'eau WO2023018326A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6664399B1 (en) * 1999-09-02 2003-12-16 E. I. Du Pont De Nemours & Company Triazole linked carbohydrates
CN102335568A (zh) * 2011-07-22 2012-02-01 浙江大学 一种含三唑环的季铵盐型阳离子表面活性剂及其合成方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6664399B1 (en) * 1999-09-02 2003-12-16 E. I. Du Pont De Nemours & Company Triazole linked carbohydrates
CN102335568A (zh) * 2011-07-22 2012-02-01 浙江大学 一种含三唑环的季铵盐型阳离子表面活性剂及其合成方法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
FARAMARZ ALIASGHARI SANI; THORSTEN HEIDELBERG; RAUZAH HASHIM; FARHANULLAH;: "Alkyl triazole glycosides (ATGs)A new class of bio-related surfactants", COLLOIDS AND SURFACES B: BIOINTERFACES, ELSEVIER AMSTERDAM, NL, vol. 97, 21 March 2012 (2012-03-21), NL , pages 196 - 200, XP028519973, ISSN: 0927-7765, DOI: 10.1016/j.colsurfb.2012.03.030 *
NG SU HAN, MAZLEE MUHAMMAD TAUFIQ FIRDAUSI BIN, HEIDELBERG THORSTEN: "Biantennary Alkyl Triazole Glycosides by Double‐ click ‐Coupling for Water‐in‐Oil‐Emulsification", JOURNAL SURFACTDETERG, vol. 24, no. 3, 1 May 2021 (2021-05-01), pages 473 - 482, XP093035390, ISSN: 1097-3958, DOI: 10.1002/jsde.12511 *
SALMAN SALIH MADHI: "Moroccan Journal of Chemistry Synthesis and physical properties of methyl glycoside linked to triazole surfactants", MOROCCAN JOURNAL OF CHEMSTRY, vol. 8, no. 2, 1 January 2020 (2020-01-01), pages 466 - 473, XP093035422, ISSN: 2351-812x *

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