Methods for preparing and purifying environmentally compatible detergents
AssigneeTakeda Pharmaceutical Company Limited
InventorsJean-Baptiste FARCET, Otto KOSTNER
Life of this patent
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Abstract
The invention provides methods for preparing and purifying compounds which can be used as environmentally compatible detergents, and compounds obtainable by such methods.
Claims74
A method for preparing and purifying a compound of the following general Formula (XIX)
- wherein m=1, R represents a hydrocarbon group having a linear chain of 2 to 12 carbon atoms and one or more methyl groups as substituents on said linear chain, and A represents a polyoxyethylene residue,
- the method comprising the steps of
- (3) Reacting a compound of the following general Formula (XII)
- wherein m and R are as defined above and X represents a halogen atom or a hydroxyl group,
- with a polyethylene glycol (PEG) of the general formula HO(CH2CH2O)nH, wherein n is an integer of n≥2, to produce a compound of said general formula (XIX) and a side product of the following general Formula (XIII)
- wherein R is as defined above and n is an integer of n≥2;
- and
- (4) Purifying the compound of said general Formula (XIX) by removing therefrom unreacted polyethylene glycol (PEG) and said side product.
The method of any one of the preceding claims, wherein in step (3), said polyethylene glycol (PEG) is used both as a reactant and as a solvent.
The method of any one of the preceding claims, wherein said step (4) comprises subjecting a solution of the compound of said general Formula (XIX) in a solvent selected from alkanes, ethers and esters and mixtures thereof to one or more aqueous washes to remove said unreacted polyethylene glycol (PEG) from the compound of said general Formula (XIX).
The method of any one of the preceding claims, wherein the purifying of said compound of said general Formula (XIX) by removing therefrom said side product in step (4) comprises subjecting a solution of said compound of said general Formula (XIX) in a mixture comprising water and a water-miscible organic solvent to one or more washes with a non-polar solvent.
The method of any one of the preceding claims, wherein step (3) is performed without employing a solvent or diluent other than said polyethylene glycol (PEG).
The method of any one of the preceding claims, wherein no halogenated solvent is used.
The method of any one of the preceding claims, which does not include the use of any preparative chromatographic methods after step (3).
The method of any one of the preceding claims, which does not include the use of any preparative chromatographic methods.
The method of any one of the preceding claims, wherein the reacting in step (3) takes place for at least 10 minutes and for not more than 1 hour.
The method of any one of the preceding claims, wherein the reacting in step (3) takes place for at least 20 minutes and for not more than 45 minutes.
The method of any one of the preceding claims, wherein the reacting in step (3) takes place for 30 minutes.
The method of any one of the preceding claims, wherein the reacting in step (3) takes place at a temperature of between 55° C. and 65° C.
The method of any one of the preceding claims, wherein the reacting in step (3) takes place at a temperature of 60° C.
The method of any one of the preceding claims, wherein in step (3), each molar equivalent (eq.) of said compound of said general Formula (XII) is reacted with at least 1.0, at least 2.0, at least 3.0 or at least 4.0 molar equivalents (eq.) of said polyethylene glycol (PEG).
The method of any one of the preceding claims, wherein in step (3), each molar equivalent (eq.) of said compound of said general Formula (XII) is reacted with at least 4.5 molar equivalents (eq.) of said polyethylene glycol (PEG).
The method of any one of the preceding claims, wherein in step (3), each molar equivalent (eq.) of said compound of said general Formula (XII) is reacted with at least 5.0 molar equivalents (eq.) of said polyethylene glycol (PEG).
The method of any one of the preceding claims, wherein said polyethylene glycol (PEG) used in step (3) is characterized in that it is liquid at the reaction temperature of said step (3).
The method of any one of the preceding claims, wherein the method is carried out at a scale which yields at least 100 g, at least 1 kg, at least 10 kg, at least 100 kg or at least 1000 kg of said compound of said Formula (XIX).
The method of any one of the preceding claims, wherein at least 1, at least 2, at least 3 or at least 4 aqueous washes are carried out after step 3.
The method of any one of the preceding claims, wherein 4 to 6 aqueous washes are carried out after step 3.
A method of purifying a compound of formula (XIX),
- wherein m=1, R represents a hydrocarbon group having a linear chain of 2 to 12 carbon atoms and one or more methyl groups as substituents on said linear chain, and A represents a polyoxyethylene residue,
- from a composition comprising the compound of formula (XIX), the method comprising subjecting a solution of said composition in a solvent selected from alkanes, ethers and esters and mixtures thereof to one or more aqueous washes.
The method of any one of the preceding claims, further comprising a step of identifying a compound of the following general Formula (XIII):
- wherein R represents a hydrocarbon group having a linear chain of 2 to 12 carbon atoms and one or more methyl groups as substituents on said linear chain, and n is an integer of n≥2.
The method of any one of the preceding claims, further comprising a step of quantifying a compound of the following general Formula (XIII):
- wherein R represents a hydrocarbon group having a linear chain of 2 to 12 carbon atoms and one or more methyl groups as substituents on said linear chain, and n is an integer of n≥2.
The method of any one of the preceding claims, wherein A represents a polyoxyethylene residue comprising 4 to 16 oxyethylene units.
The method of any one of the preceding claims, wherein A represents a polyoxyethylene residue comprising 8 to 10 oxyethylene units.
The method of any one of the preceding claims, wherein A represents a polyoxyethylene residue comprising 9 or 10 oxyethylene units.
The method of any one of the preceding claims, wherein R represents a hydrocarbon group having a linear chain of 2 to 6 carbon atoms and one or more methyl groups as substituents on said linear chain.
The method of any one of the preceding claims, wherein R represents a hydrocarbon group having a linear chain of 2 to 6 carbon atoms and 2 to 4 methyl groups as substituents on said linear chain.
The method of any one of the preceding claims, wherein R represents a hydrocarbon group having a linear chain of 4 carbon atoms and 4 methyl groups as substituents on said linear chain.
The method of any one of the preceding claims, wherein R represents a 2,4,4-trimethyl-pent-2-yl group.
The method of any one of the preceding claims, wherein the compound of Formula (XIX) is the following compound:
- wherein m equals 1 and z is an integer selected from:
- z=1 to 5.
The method of any one of the preceding claims, wherein the compound of Formula (XIX) is the following compound:
- wherein n is an integer between 4 and 16, preferably wherein n is equal to 8, 9 or 10.
A compound of the following general Formula (XIX)
- wherein m=1, R represents a hydrocarbon group having a linear chain of 2 to 12 carbon atoms and one or more methyl groups as substituents on said linear chain, and A represents a polyoxyethylene residue,
- and wherein said compound is obtainable by the method of any one of the preceding claims.
Use of a non-polar solvent for extracting and removing a compound of the following general Formula (XIII):
- wherein R represents a hydrocarbon group having a linear chain of 2 to 12 carbon atoms and one or more methyl groups as substituents on said linear chain and n is an integer of n≥2,
- from a composition comprising said compound of Formula (XIII) and a compound of formula (XIX),
- wherein m=1, R represents a hydrocarbon group having a linear chain of 2 to 12 carbon atoms and one or more methyl groups as substituents on said linear chain, and A represents a polyoxyethylene residue.
Dependencies are inferred from the claim text.