WO2008012231A2 - Utilisation de 1,5-diméthylpyrrolidone - Google Patents

Utilisation de 1,5-diméthylpyrrolidone Download PDF

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Publication number
WO2008012231A2
WO2008012231A2 PCT/EP2007/057347 EP2007057347W WO2008012231A2 WO 2008012231 A2 WO2008012231 A2 WO 2008012231A2 EP 2007057347 W EP2007057347 W EP 2007057347W WO 2008012231 A2 WO2008012231 A2 WO 2008012231A2
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dimethylpyrrolidone
solvent
containing copolymers
processes
copolymers
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WO2008012231A3 (fr
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Tobias Wabnitz
Rolf Pinkos
Karl Ott
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom

Definitions

  • the present invention relates to uses of 1, 5-dimethylpyrrolidone (1, 5-dimethyl-2-pyrrolidinone, DMP, CAS No. 5075-92-3), especially in certain processes.
  • NMP N-methylpyrrolidone
  • WC Walsh "N-Methyl Pyrrolidone (NMP Technical Tips), Maintenance Cleaning Aircraft Ball Bearing Assemblies", WC Walsh, “N-Methyl Pyrrolidone (NMP Technical Tips); Cleaning of a Chlorinated Paraffin / Metal Stearate Based Compound Drawing Off of 1000 Ft. Long Coils of 0.25", 316 Stainless Steel Tubing ",
  • WO-A-05/090447, DE-A-102004015095, WO-A-05/092953 and DE-A-102004015092 relate to the use of N-ethylpyrrolidone, N-methylvalerolactam, N-methylcaprolactam or 3-Ethoxypropionicklaethylester.
  • the object of the present invention is to find a substitute for NMP and also chlorinated hydrocarbons and / or ethers which has at least approximately, preferably equally good, in particular also improved properties in the applications in which these substances, in particular NMP, are used come.
  • This replacement for NMP should also have similar physical properties, e.g. viscosity, colorlessness, polarity, inertness, biodegradability, homogeneous miscibility with other organic solvents and water.
  • the replacement should in particular have even more favorable toxicological properties, i. be even less toxic than NMP.
  • 1, 5-dimethylpyrrolidone is such a substitute for NMP and also chlorinated hydrocarbons and / or ethers.
  • the invention accordingly provides for the use of 1, 5-dimethylpyrrolidone as solvent, diluent, extractant, cleaning agent, degreasing agent, absorption agent and / or dispersing agent.
  • 5-dimethylpyrrolidone is a slowly evaporating, highly polar, aprotic and widely applicable organic solvent (boiling point: 210 0 C / 1013 mbar) with favorable ecological data (see safety data sheet to 1, 5-dimethylpyrrolidone from Sigma Aldrich Chemie GmbH, Germany , Product No. D184101). It is a colorless, low-viscosity liquid with a weak amine odor. 1, 5-Dimethylpyrrolidone is completely miscible with water and most organic solvents.
  • 1, 5-dimethylpyrrolidone has favorable toxicological data. (See safety data sheet for 1, 5-dimethylpyrrolidone from Sigma Aldrich Chemie GmbH, Germany, Product No. D184101).
  • inorganic substances examples include sulfur, zinc chloride, sodium nitrite, sodium bromide, mercuric chloride, some iron, copper and lead salts. All the above features make 1, 5-dimethylpyrrolidone a good or the best choice for a wide range of different applications (see below).
  • 5-dimethylpyrrolidone is an e.g. levulinic acid-based lactam and a very weak base.
  • 5-dimethylpyrrolidone is a chemically stable and powerful polar solvent. These properties are very valuable in various chemical reactions where an inert medium is important:
  • Carboxylic acids, carboxylic anhydrides and carboxylic acid esters can be prepared by reaction of alcohols with synthesis gas (CO + Hb) using nickel or
  • Cobalt complexes can be prepared in 1, 5-dimethylpyrrolidone.
  • Another method is the production of ethylene glycol from synthesis gas.
  • 1, 5-dimethylpyrrolidone is also preferably used in the following known processes in which it replaces NMP (see, for example, the BASF AG brochure 'BASF Intermediates', 'N-methylpyrrolidone (NMP)', No. CZ 3307). 0291-2.0 (circa 1994) and the literature cited therein, which is hereby incorporated by reference):
  • 1, 5-dimethylpyrrolidone Hydrocarbons by extractive distillation.
  • 1, 5-dimethylpyrrolidone offers the following advantages: no azeotropes are formed with hydrocarbons; 1, 5-dimethylpyrrolidone is very resistant to heat and chemicals; and 1, 5-dimethylpyrrolidone has a favorable toxicological and ecological profile.
  • 5-dimethylpyrrolidone is miscible in all proportions with water. This allows adjustment of the process to the desired conditions and stripping of the dissolved hydrocarbons from the solvent.
  • 5-dimethylpyrrolidone has a high boiling point associated with low vapor pressure, which minimizes losses in industrial scale separation processes. The viscosity is low at the usual operating temperatures, which promotes the transport of substances.
  • 1, 5-dimethylpyrrolidone can be successfully used for the separation and purification of acetylene from cracking gas mixtures resulting from the partial combustion of saturated hydrocarbons [vgl. for example: H. Höfermann et al., Chem. Industrie 21, 860 (1969); H. Friz, Chem. Ing. Techn. 40 (20), 999 (1968)].
  • 8 to 10% of the gas volume obtained in this pyrolysis reaction consists of acetylene, about 4% of carbon dioxide, hydrogen and carbon monoxide.
  • 1, 5-dimethylpyrrolidone dissolves many times its own volume of acetylene. Acetylene can be easily removed from the light Key component carbon dioxide and be separated from higher acetylenes.
  • a particular advantage of this method is that there is no risk of spontaneous decomposition of the acetylene.
  • Natural gas, naphtha or liquefied petroleum gas (LPG) are converted into an acetylenic gas in the BASF immersion flame process [Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, VCH Verlagsgesellschaft, Weinheim, Vol. A1, 107 (1985)], quenching with water and Coke deposits are removed or quenched with oil, coke deposits are removed and heat is recovered.
  • the purification of the resulting cracking gas consists of two stripping steps, in which 1, 5-dimethylpyrrolidone can be used as a selective solvent.
  • a butadiene of high purity (99.5 to 99.9 g / 100 g) and high yields (98%) is obtained from C 4 hydrocarbon feeds.
  • an essential process step can be 1, 5-dimethylpyrrolidone, which contains, for example, about 8 g of water / 100 g, as a selective solvent, for example, in a two-stage extractive distillation.
  • the BASF process for the recovery of isoprene (2-methyl-1,3-butadiene) is a further development of the butadiene process described above.
  • the separation can be carried out either by extractive distillation or by liquid-liquid extraction.
  • Cs sections from pyrolysis reactions contain 15 to 20 g of isoprene / 100 g.
  • the purity of the final product is high, eg 99% [H. Kröper and HM Weitz, OiI Gas J. 65 (2), 98 (1967)].
  • a solvent mixture with an excellent selectivity and a high dissolving power is ensured.
  • the latter term is defined as the ratio of the aromatic concentration in the solvent phase to the aromatic concentration in the hydrocarbon phase.
  • 1, 5-dimethylpyrrolidone offers over other solvents, among others the advantage that the conditions for the separation by distillation of the extracted aromatics are optimal due to the favorable location of its boiling point. It is also advantageous that the phases can be separated quite quickly by utilizing the difference in density and that 1, 5-dimethylpyrrolidone is chemically and thermally stable at the temperatures used in the process.
  • the extraction of pure benzene from the crude product is carried out by extractive distillation with NMP as a selective solvent, which can be replaced by 1, 5-dimethylpyrrolidone. The same applies to toluene or xylene from the corresponding distillation phases.
  • High performance lubricating oils are a mixture of petroleum fractions from which quality reducing aromatics and nitrogen, oxygen or sulfur compounds have been extracted by solvent refining. Then the components with the best lubricating properties - the isoparaffins - are separated from the n-paraffins.
  • the aromatics and other impurities dissolve to varying degrees in organic high boilers. These differences are used in their separation from the paraffins in technical solvent refining.
  • An advantageous solvent for this purpose is 1, 5-dimethylpyrrolidone [See: JD Bushnell and RT Fiocco, Hydrocarbon Proc. 59 (5), 19 (1980); A. Sequeira, PB Sherman, TU Donciere and EO McBride, Hydrocarbon Proc. 58 (9), 155 (1979)].
  • the feed is fed to the bottom of the extraction column and allowed to flow in countercurrent to the degassed 1, 5-dimethylpyrrolidone.
  • the column is thus designed as a multi-stage extraction zone.
  • 1, 5-dimethylpyrrolidone is thermally and chemically stable, has favorable toxicological and ecological properties and excellent selectivity, and is a very good solvent in terms of raffinate yields.
  • 1, 5-dimethylpyrrolidone can be used as a solvent for natural and synthetic plastics, waxes, resins, and various types of paints. It dissolves polymers such as cellulose derivatives, polymethylmethacrylate, polyamides, polyimides, polyesters, polystyrene, polyacrylonitrile, polyvinylchloride, polyvinylpyrrolidone, polyvinylacetate, polyurethanes, polycarbonates, polyethersulfones, polysulfones, polyethers and numerous copolymers.
  • polymers such as cellulose derivatives, polymethylmethacrylate, polyamides, polyimides, polyesters, polystyrene, polyacrylonitrile, polyvinylchloride, polyvinylpyrrolidone, polyvinylacetate, polyurethanes, polycarbonates, polyethersulfones, polysulfones, polyethers and numerous copolymers.
  • 1, 5-dimethylpyrrolidone is very useful because it can be made of polyamides, polyacrylonitrile, polyvinyl chloride, polystyrene and cellulose triacetate highly concentrated solutions or moldable compositions. The same applies at elevated temperature for vinyl fluoride homopolymers and copolymers. Due to its swelling and solubilization effect, 1,5-dimethylpyrrolidone can also be used for cold welding of plastics.
  • Aromatic polyamides are excellent components for the production of films, fibers and yarns, which offer the extremely high strength required for technical applications.
  • the preferred poly (p-phenylene terephthalamide) as starting material in the industry is obtained by reacting p-phenylenediamine and terephthalic acid dichloride in concentrated 1, 5-dimethylpyrrolidone-
  • High performance aramid fibers and yarns can be made from spinning solutions of poly (p-phenylene terephthalamide) or other polyamide-based polymer compositions by conventional wet and dry spinning techniques.
  • Lithium chloride-containing 1, 5-dimethylpyrrolidone is a solvent for the preparation of polymers of aromatic diamines and aromatic acid chlorides, such as isophthalic acid chloride, which can form fibers and coatings and are resistant to high temperatures.
  • Polyacrylonitrile which is insoluble in most organic solvents, can be dissolved in 1,5-dimethylpyrrolidone with small amounts of lower aliphatic ketones. These solutions can be spun into uniform fibers at relatively low temperatures.
  • Fibrous poly (arylene ether sulfone) -poly (arylene terephthalate) block copolymers can be prepared by using a solution of potassium carbonate and 1,5-dimethylpyrrolidone by interfacial method.
  • Fibers of poly (arylacetylene) can be wet spun in organic solvents such as 1,5-dimethylpyrrolidone.
  • Urea can be condensed in 1, 5-dimethylpyrrolidone at temperatures above 150 0 C with diamines.
  • the linear, uncrosslinked polyureas thus obtained have a high molecular weight and good mechanical properties and can be made into fibers.
  • 1,5-Dimethylpyrrolidone dissolves both the polymers and the monomers at elevated temperatures, but the polymers precipitate upon cooling the solution to room temperature. Therefore, 1,5-dimethylpyrrolidone is superior to a phenolic solvent because it simplifies the process and improves the quality.
  • 1, 5-dimethylpyrrolidone is suitable as a non-corrosive, inert solvent for the condensation reaction and subsequent spinning.
  • 1, 5-dimethylpyrrolidone can be used for the production of semipermeable membranes. These membranes are used in separation processes such as ultrafiltration and reverse osmosis.
  • Polyethersulfone membranes can be prepared from multicomponent mixtures from 1, 5
  • polysulfone membranes The properties of polysulfone membranes are determined by solutions in 1, 5
  • 1, 5-dimethylpyrrolidone allows the synthesis of new polymers and / or the synthesis of polymers to improve their quality.
  • 1, 5-dimethylpyrrolidone catalyzes the foaming reaction to highly hydrophilic, soft articles.
  • 1, 5-dimethylpyrrolidone acts as a regulator to ensure open-cell structures.
  • the properties of polyester urethane rubber solutions in the presence of 1, 5-dimethylpyrrolidone are advantageous.
  • Linear synthetic polyamides are readily soluble in 1,5-dimethylpyrrolidone at 150 to 200 ° C. and poorly soluble at room temperature; The same applies to polycaprolactam and copolymers of caprolactam with, for example, N-vinylcaprolactam. This property enables the separation of impurities such as unreacted monomers and colored substances by recrystallization.
  • solvents such as 1,5-dimethylpyrrolidone are very well suited. 1, 5-dimethylpyrrolidone dissolves the monomer and the activator and swells the precipitated polymer.
  • acrylates or methacrylates are anionically polymerized in the presence of dipolar, aprotic cocatalysts, such as 1,5-dimethylpyrrolidone, the proportion of syndiotactic polymer increases, so that the products obtained have a more regular structure. Due to the resulting improvements in heat distortion resistance, solvent resistance and mechanical properties, these products are useful as molding compounds and as binders for surface coatings.
  • dipolar, aprotic cocatalysts such as 1,5-dimethylpyrrolidone
  • the photo-curing of acrylic epoxy resins can be carried out with N-vinylpyrrolidone as a reactive diluent and 1,5-dimethylpyrrolidone as an unreactive diluent.
  • Amorphous polyacrylether which are very temperature resistant, can be advantageously prepared using 1, 5-dimethylpyrrolidone. Side reactions are avoided by the use of weak bases [see: D.K. Mohanty et al., Polymer Preprints 25 (2), 19 (1984)].
  • 1, 5-Dimethylpyrrolidone can be used as a reaction medium in the synthesis of high performance poly (phenylene sulfide) for the polymerization of p-dichlorobenzene and sodium sulfide.
  • the ring-opening polymerization of poly can be carried out in the solvent system 1, 5-dimethylpyrrolidone and lithium chloride.
  • 1, 5-Dimethylpyrrolidone is a non-corrosive high boiler with excellent dissolving power and excellent chemical resistance. Therefore improved 1, 5-dimethylpyrrolidone the properties of many surface coating systems. These effects are particularly favorable for baking coatings which are cured at relatively high temperatures.
  • 1, 5-dimethylpyrrolidone allows the production of highly filled paints and varnishes. As it improves the rheological properties, it gives coatings with superior flow and superior hiding power. The coatings are therefore more homogeneous and non-porous and show no cratering and greater chemical resistance and a higher mechanical strength.
  • Starting materials for coatings such as acrylates, epoxy resins, polyurethanes, polyvinyl chloride systems, polyamide-imide-based wire enamels, waterborne basecoats and printing inks, e.g. for ink jet printers, such as water resistant ink jet inks, optionally containing a UV curable resin.
  • 1, 5-Dimethylpyrrolidone is a useful solvent for butadiene-acrylonitrile copolymers (e.g., Perbunan N) used to coat tanks.
  • the rubber solutions flow and run better than the solutions obtained with ketones.
  • Polyisocyanates with imide groups can be dissolved in solvent systems with 1, 5-dimethylpyrrolidone. These solutions can be used for the gumming of composites and metal surfaces.
  • 1,5-dimethylpyrrolidone in the preparation of thermosetting paints for electrical insulation is its excellent solvent power for polycarboxylic acids and their anhydrides, such as trimellitic acid and pyromellitic anhydride, and polymers with high aromatic content amide and carboxyl groups.
  • 5-dimethylpyrrolidone solutions of anhydrides of polybasic carboxylic acids and monomeric polyfunctional isocyanates amide group-containing polyisocyanates are formed.
  • the baked enamels obtained give coatings with excellent mechanical and dielectric properties on copper conductors.
  • 5-dimethylpyrrolidone has the advantage that it has a dual function: it serves as a reaction medium in the preparation process and remains in the finished coating as a viscosity modifier.
  • 1, 5-Dimethylpyrrolidone is useful as a solvent for the resinous copolyesters in the reaction between a diimide (such as obtained from trimellitic anhydride and 4,4'-diaminodiphenylmethane) and polyhydric alcohols (such as trishydroxyethyl isocyanurate (THEIC) or ethylene glycol).
  • a diimide such as obtained from trimellitic anhydride and 4,4'-diaminodiphenylmethane
  • polyhydric alcohols such as trishydroxyethyl isocyanurate (THEIC) or ethylene glycol.
  • TEEIC trishydroxyethyl isocyanurate
  • 1,5-Dimethylpyrrolidone is also a solvent for polyamide / polyimide stoving lacquers derived from the condensation of a tricarboxylic acid with aromatic and aliphatic diamines.
  • Solvent mixtures of 1, 5-dimethylpyrrolidone and dicarboxylic acid esters are suitable for use in the production of wire coatings based on polyvinyl formal.
  • 1, 5-dimethylpyrrolidone Due to its high dissolving power for plastics, resins, oils and fats, 1, 5-dimethylpyrrolidone can be successfully used as a component in paint removers, cleaners and degreasers. Its miscibility with water and most conventional organic solvents enables the production of highly effective products that can be targeted to different applications.
  • the ecological and toxicological data of 1, 5-dimethylpyrrolidone are favorable compared to most other solvents. 1, 5-dimethylpyrrolidone is not corrosive. Mixtures containing 1,5-dimethylpyrrolidone and other solvents often show desirable synergistic effects.
  • 1, 5-Dimethylpyrrolidone can be used alone or in mixtures for the removal of oil, carbon deposits and other tarry polymeric residues from metal chambers, pistons and cylinders and for wet cleaning of internal combustion engines.
  • 1, 5-dimethylpyrrolidone may be part of mixtures used in industry for cleaning soiled metal parts and equipment. Certain difficult to dissolve polyurethanes are best purified with mixtures of 1, 5-dimethylpyrrolidone and dicarboxylic acid esters. Mixtures of 1, 5-dimethylpyrrolidone with other organic solvents and excipients are used to remove ink residues. Mixtures containing 1, 5-dimethylpyrrolidone as the key ingredient are used to remove epoxies and similar chemically resistant coatings on steel surfaces, as well as temporary coatings of parts of optical instruments.
  • Solvent blends containing 1, 5-dimethylpyrrolidone as a reactive ingredient are useful in preparing a foam-type paint remover suitable for use in the removal of various paints, clearcoats, air-drying paints and other coatings or coatings, particularly relatively large surfaces ,
  • 1, 5-Dimethylpyrrolidone can be used to form paint removers that are easy to handle, environmentally friendly and reduce the risk of fire.
  • Mixtures of 1, 5-dimethylpyrrolidone may be used to clean objects or surfaces soiled by substances such as oil, grease, soot, paint and adhesive by immersion in a bath.
  • An important area of application in this context is the degreasing of metals prior to further surface treatment, coating or electroplating.
  • Cleaning baths to be used include 1, 5-dimethylpyrrolidone, odor masking agents, surfactants and diluents.
  • Products based on 1,5-dimethylpyrrolidone are suitable for use in removing weathered emulsion paints on exterior walls, for interior renovation, graffiti removal and ultrasonic cleaning of items such as lenses or dentures.
  • solvents can be used in combination with surfactants, thickeners, and other additives to develop high solvent and swelling systems:
  • 1, 5-dimethylpyrrolidone can be used as a solvent or co-solvent for the formulation of drugs such as insecticides, fungicides, herbicides, seed treatment products and bioregulators where highly polar compounds are required.
  • drugs such as insecticides, fungicides, herbicides, seed treatment products and bioregulators where highly polar compounds are required.
  • 1, 5-dimethylpyrrolidone is preferred over other highly polar solvents because when used as a solvent or Co-solvent in pesticide formulations applied to growing crops, is exempt from the requirement for tolerance and has a favorable toxicological and environmental profile. It is particularly suitable for multicomponent systems.
  • 1, 5-dimethylpyrrolidone forms adducts with bacteriostats such as substituted ureas, carbanilides, thiocarbamates, guanidines and salicylanilides. These products are more bactericidal and allow better control of the growth of bacterial cultures.
  • Polyamideimide, urethane and epoxy resins give a smooth surface.
  • the slow rate of evaporation of 1, 5-dimethylpyrrolidone allows the formation of very homogeneous coatings.
  • ICs are encapsulated with resins, such as epoxy molding compounds.
  • resin flash (flash) is left on the encapsulated IC package or terminal comb and on the encapsulation device
  • Printed circuit boards are used to solder semiconductors and other electrical components. In this case, a flux must be used. After soldering flux residues must be removed to prevent corrosion. This can be done with solvent mixtures containing as key component 1, 5-dimethylpyrrolidone. Another area of application is the selective removal of polymer coatings from certain areas on printed circuit boards.
  • 1, 5-dimethylpyrrolidone or mixtures thereof can be widely used as absorption media for the removal or separation of organic compounds from waste or flue gases such as sulfur dioxide, hydrogen sulfide and vinyl chloride.
  • diazotizable amine dispersions can be prepared with 1,5-dimethylpyrrolidone which dissolves the diazo and coupling components.
  • 1,5-dimethylpyrrolidone can be used in the dyeing of polyamide, acrylic, polyester fibers, fabrics, films and polyester-cotton blends.
  • Pigment coatings 1, 5-dimethylpyrrolidone effectively disperses many organic or inorganic color pigments without increasing the water sensitivity of the film. 1% solvent (based on pigment) facilitates grinding and increases coloring power due to pigment refining. 1, 5-dimethylpyrrolidone improves stability against aging, gives reduced color drift and stabilizes the system against flocculation and solidification.
  • cyanoacrylate based adhesives for removing contaminants and adhesives, especially cyanoacrylate based adhesives, polymers, plastics (e.g., polymethacrylates), glass, metal, ceramic, stone and fiber surfaces, and also from the skin.
  • DMF Dimethylformamide
  • Solvents e.g., chlorinated hydrocarbons, especially chlorinated C 1 -C 6 hydrocarbons such as tetrachlorethylene and trichlorethylene
  • solvents e.g. in ultrasonic cleaning processes, caustic soda in cleaning reactors e.g. for removing urethane residues, furfural phenol in lubricant extractions and glycol ethers, e.g. in household and industrial cleaners and coatings, ethers such as e.g. THF, diethylene glycol dialkyl ether, 1, 2-diethoxyethane and 1, 2-dimethoxyethane, e.g. in chemical reactions.
  • THF diethylene glycol dialkyl ether
  • 1, 2-diethoxyethane and 1, 2-dimethoxyethane e.g. in chemical reactions.
  • 1, 5-dimethylpyrrolidone is used for the uses according to the invention in particular with a purity of greater than 97 wt .-%, in particular greater than 98 wt .-%, especially greater than 99 wt .-%, e.g. greater than 99.8 or greater than 99.9 wt .-% used.
  • These purities can be achieved by single or multiple distillation or rectification.
  • 1, 5-dimethylpyrrolidone The preparation and purification of 1, 5-dimethylpyrrolidone is known. See, for example: JP-A-1186864, NL-A-71 17842 (US 3,775,431), WO-A-2005 0261 15, US 2005 033062, JP-A-51016657.
  • the preparation of 1, 5-dimethylpyrrolidone by reaction of gamma-methylbutyrolactone with monomethylamine at elevated temperature and elevated pressure to release one molar equivalent of water, for.
  • 1, 5-dimethylpyrrolidone may also be effected by methylation of gamma-methylpyrrolidone, e.g. with methanol; See, for example, Chem. Abstract. 120: 191559 (RO-B1 -102421) and Chem. 118: 233904 (EP-A1-531 673) and DD-A1-267 729.
  • EP-A1-1 038 867 (BASF AG) and US-A-5,777,131 (BASF Corp.) describe processes for the purification of N-substituted lactams such as NMP and 1, 5-dimethylpyrrolidone, wherein the contaminated N-substituted lactams with a treated acidic, especially macroporous, cation exchangers.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Pyrrole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne l'utilisation de 1,5-diméthylpyrrolidone en tant que solvant, diluant, agent d'extraction, agent de purification, agent dégraissant, agent d'absorption et/ou dispersant, notamment en remplacement total ou partiel de la N-méthyl-2-pyrrolidone (NMP), des hydrocarbures chlorés et/ou des éthers.
PCT/EP2007/057347 2006-07-27 2007-07-17 Utilisation de 1,5-diméthylpyrrolidone Ceased WO2008012231A2 (fr)

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US8129577B2 (en) 2008-09-16 2012-03-06 Air Products And Chemicals, Inc. Process and system for providing acetylene
EP3045488A1 (fr) 2015-01-15 2016-07-20 Rohm and Haas Electronic Materials LLC Compositions de polyimide et procédés
EP3872099A1 (fr) * 2020-02-26 2021-09-01 Kraton Polymers Research B.V. Polymère purifié et ses procédés de fabrication
US20230130822A1 (en) * 2020-02-14 2023-04-27 Angus Chemical Company Low toxicity nmp substitutes and uses thereof

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US8129577B2 (en) 2008-09-16 2012-03-06 Air Products And Chemicals, Inc. Process and system for providing acetylene
US8915992B2 (en) 2008-09-16 2014-12-23 Air Products And Chemicals, Inc. Process and system for providing acetylene
WO2010142617A1 (fr) * 2009-06-10 2010-12-16 Basf Se Utilisation de nouveaux solvants pour la préparation de dispersions de polyuréthane
CN102459383A (zh) * 2009-06-10 2012-05-16 巴斯夫欧洲公司 用于生产聚氨酯分散体的新溶剂
JP2012529547A (ja) * 2009-06-10 2012-11-22 ビーエーエスエフ ソシエタス・ヨーロピア ポリウレタン分散液の製造における新規の溶媒
US8575244B2 (en) 2009-06-10 2013-11-05 Basf Se Solvents in the preparation of polyuretherane dispersions
EP3045488A1 (fr) 2015-01-15 2016-07-20 Rohm and Haas Electronic Materials LLC Compositions de polyimide et procédés
US20230130822A1 (en) * 2020-02-14 2023-04-27 Angus Chemical Company Low toxicity nmp substitutes and uses thereof
EP3872099A1 (fr) * 2020-02-26 2021-09-01 Kraton Polymers Research B.V. Polymère purifié et ses procédés de fabrication

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