DE102010031301A1 - Use of 1,3-dimethylpyrrolidone and/or 1,4-dimethylpyrrolidone as solvents, diluents, extractants, cleaning agents, degreasers, absorbents and/or dispersing agents, or a solvent and/or extractant in method for decomposition of gas mixtures - Google Patents

Abstract

Use of 1,3-dimethylpyrrolidone and/or 1,4-dimethylpyrrolidone as: solvents, diluents, extractants, cleaning agents, degreasers, absorbents and/or dispersing agents; a solvent and/or extractant in method for the decomposition of gas mixtures; a solvent for polymers and/or copolymers, resins, cellulose derivatives and dyes; solvents, diluents and/or dispersing agents in chemical reactions; a solvent for the production of electrode slurries for lithium-ion batteries; a partial or complete replacement of N-methyl-2-pyrrolidone; or in inks for inkjet printers, is claimed. Use of 1,3-dimethylpyrrolidone and/or 1,4-dimethylpyrrolidone as: solvents, diluents, extractants, cleaning agents, degreasers, absorbents and/or dispersing agents; a solvent and/or extractant in method for the decomposition of gas mixtures; a solvent for polymers and/or copolymers, resins, cellulose derivatives and dyes; solvents, diluents and/or dispersing agents in chemical reactions; a solvent in process for the production of wire enamels; a solvent and/or absorbent in process for gas scrubbing; solvents, cleaning agents and/or degreasing agents in process for manufacturing integrated circuits; a solvent or cosolvent in the formulation of active substances such as insecticides, fungicides, herbicides, seed treatment products and bioregulators, and pharmaceutical drugs, preferably for the formulation in hard and soft gelatin capsules; a solvent for the production of electrode slurries for lithium-ion batteries; a partial or complete replacement of N-methyl-2-pyrrolidone; or in inks for inkjet printers, is claimed.

Description

The The present invention relates to uses of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone (1,3-dimethyl-2-pyrrolidinone, DMP, CAS no. 2555-04-6; 1,4-dimethyl-2-pyrrolidinone, DMP, CAS no. 19597-07-0) especially in certain procedures.

When a highly polar, aprotic and widely applicable organic Low viscosity solvent with Water and other organic solvents homogeneously miscible N-methylpyrrolidone (NMP) is in research and engineering established.

• W. C. Walsh, M. Waldrop and R. Atkins, ”A process to Vacuum Vapor Degrease Metal Parts with N-Methyl Pyrrolidone”, 1997, CA Abstract Nr. 127:7688 .
• Die Broschüre ”Formulating Paint Strippers with N-Methylpyrrolidone”, BASF Corporation, Chemical Intermediates, 1990, USA ,

sowie die folgenden 17 Publikationen der BASF Corporation, Chemicals Division, USA:

• W. C. Walsh, ”Removal of Rosin and Resin based Solder Flux from electronic assemblies with N-methylpyrrolidone/water mixtures” ,
• W. C. Walsh, ”Degreasing and Solvent Regeneration in Metal Parts, Cleaning using N-Methylpyrrolidone”, z. B.: http://es.epa.gov/p2pubs/oaic/301.html .
• W. C. Walsh, ”Surface Tension Modification of NMP-based Paint Strippers” ,
• W. C. Walsh, ”N-Methyl Pyrrolidone (NMP Technical Tips), Removal of Paints and Coatings from NMP Soluble Plastics” ,
• Walsh, W. C. (1991), ”Surface Tension Modification of NMP-based Paint Strippers”. In: Reducing Risk in Paint Stripping, Washington D. C., 12–13 February 1991, pp. 177–184 . Economics and Technology Division; Office of Toxic Substances; United States Environmental Protection Agency, Washington D. C., 1991 ,
• W. C. Walsh, ”N-Methyl Pyrrolidone (NMP Technical Tips), Maintenance Cleaning of Aircraft Ball Bearing Assemblies” ,
• W. C. Walsh, ”N-Methyl Pyrrolidone (NMP Technical Tips); Cleaning of a Chlorinated Paraffin/Metal Stearate Based Drawing Compound Off of 1000 Ft. Long Coils of 0.25 Inch, 316 Stainless Steel Tubing” ,
• W. C. Walsh, ”N-Methyl Pyrrolidone (NMP Technical Tips), Chemical Warfare Resistant Coatings (CARC), Removal From Metal Surfaces” ,
• W. C. Walsh, W. Monahan and M. Waldrop, ”Reflux Cleaning of Large Reactors with N-Methyl Pyrrolidone (NMP)” ,
• W. C. Walsh, ”Replacement of MEK with N-Methyl Pyrrolidone (NMP) in Coatings Plant Resin Clean Up Operations” ,
• W. C. Walsh, ”N-Methyl Pyrrolidone (NMP) Technical Tips, Removal of POLYURETHANE/POLYUREA RESIDUE from the Interior Surfaces of a Batch Reactor Vessel” ,
• W. C. Walsh, ”N-Methyl Pyrrolidone – Cleaning Applications in the Urethane Manufacturing and Processing Industries” ,
• M. W. Waldrop and W. C. Walsh, ”Modification of a Vapor Degreasing Machine for Immersion Cleaning using N-Methyl Pyrrolidone” ,
• W. C. Walsh, ”Removal of N-Methyl Pyrrolidone From Metal Parts Using A Centrifugal Dryer” ,
• W. C. Walsh, M. Waldrop and R. Atkins, ”A Process to Vacuum Vapor Degrease Metal Parts with N-Methyl Pyrrolidone”, http://es.epa.gov/techpubs/3/15413.html ,
• W. C. Walsh, R. T. Chwalik, K. E. Hinzman and M. Waldrop, ”Removal of N-Methyl Pyrrolidone (NMP) from Industrial Plant Exhaust Air with a Packed Column Scrubber” , und
• W. C. Walsh, ”N-Methyl Pyrrolidone (NMP Technical Tips), Reclaiming or Recycling of NMP” , und weiterhin
• ”Electrical Insulation – From Wire enamel to Enamelled Wire”, 1 Beck Information, July 1992, (Beck Electrical Insulation Systems, Hamburg) .

By way of example, the following publications relating to NMP may be mentioned here:

• WC Walsh, M. Waldrop and R. Atkins, "A Process to Vacuum Vapor Degrease Metal Parts with N-Methyl Pyrrolidone", 1997, CA Abstract No. 127: 7688 ,
• The brochure "Formulating Paint Strippers with N-Methylpyrrolidone", BASF Corporation, Chemical Intermediates, 1990, USA .

and the following 17 publications of BASF Corporation, Chemicals Division, USA:

• WC Walsh, "Removal of Rosin and Resin based Solder Flux from electronic assemblies with N-methylpyrrolidone / water mixtures" .
• WC Walsh, "Degreasing and Solvent Regeneration in Metal Parts, Cleaning using N-Methylpyrrolidone", e.g. B .: http://es.epa.gov/p2pubs/oaic/301.html ,
• WC Walsh, "Surface Tension Modification of NMP-based Paint Strippers" .
• WC Walsh, "N-Methyl Pyrrolidone (NMP Technical Tips), Removal of Paints and Coatings from NMP Soluble Plastics" .
• Walsh, WC (1991), "Surface Tension Modification of NMP-based Paint Strippers". In: Reducing Risk in Paint Stripping, Washington DC, 12-13 February 1991, pp. 177-184 , Economics and Technology Division; Office of Toxic Substances; United States Environmental Protection Agency, Washington DC, 1991 .
• WC Walsh, "N-Methyl Pyrrolidone (NMP Technical Tips), Maintenance Cleaning of Aircraft Ball Bearing Assemblies" .
• WC Walsh, "N-Methyl Pyrrolidone (NMP Technical Tips); Cleaning of a Chlorinated Paraffin / Metal Stearate Based Drawing Compound Off of 1000 Ft. Long Coils of 0.25 ", 316 Stainless Steel Tubing" .
• WC Walsh, "N-Methyl Pyrrolidone (NMP Technical Tips), Chemical Warfare Resistant Coatings (CARC), Removal From Metal Surfaces" .
• WC Walsh, W. Monahan and M. Waldrop, "Reflux Cleaning of Large Reactors with N-Methyl Pyrrolidone (NMP)" .
• WC Walsh, "Replacement of MEK with N-Methyl Pyrrolidone (NMP) in Coatings Plant Resin Clean Up Operations" .
• WC Walsh, "N-Methyl Pyrrolidone (NMP) Technical Tips, Removal of POLYURETHANE / POLYUREA RESIDUE from the Interior Surfaces of a Batch Reactor Vessel" .
• WC Walsh, "N-Methyl Pyrrolidones - Cleaning Applications in the Urethane Manufacturing and Processing Industries" .
• MW Waldrop and WC Walsh, "Modification of a Vapor Degreasing Machine for Immersion Cleaning using N-Methyl Pyrrolidone" .
• WC Walsh, "Removal of N-Methyl Pyrrolidone From Metal Parts Using a Centrifugal Dryer" .
• WC Walsh, M. Waldrop and R. Atkins, "A Process to Vacuum Vapor Degrease Metal Parts with N-Methyl Pyrrolidone", http://es.epa.gov/techpubs/3/15413.html .
• WC Walsh, RT Chwalik, KE Hinzman and M. Waldrop, "Removal of N-Methyl Pyrrolidone (NMP) from Industrial Plant Exhaust Air with a Packed Column Scrubber" , and
• WC Walsh, "N-Methyl Pyrrolidone (NMP Technical Tips), Reclaiming or Recycling of NMP" , and still
• "Electrical Insulation - From Wire Enamel to Enamelled Wire", 1 Beck Information, July 1992, (Beck Electrical Insulation Systems, Hamburg) ,

WO-A-05/090447 . DE-A-10 2004 015 095 . WO-A-05/092953 and DE-A-10 2004 015 092 (all from BASF AG) relate to the use of N-ethylpyrrolidone, N-methylvalerolactam, N-methylcaprolactam or ethyl 3-ethoxypropionate.

Of the present invention is based on the object of a replacement for NMP and also chlorinated hydrocarbons and / or To find ether, at least approximately, preferably the same good, especially improved properties in the applications in which these substances, in particular NMP, are used.

This Replacement for NMP should also be similar physical Properties, e.g. B. concerning viscosity, colorlessness, Polarity, inertness, biodegradability, homogeneous miscibility with other organic solvents and water. The replacement should be even more favorable toxicological Have properties, d. H. be even less toxic than NMP.

According to the invention was recognized that 1,3-dimethylpyrrolidone, 1,4-dimethylpyrrolidone or mixtures from both such a replacement for NMP and also chlorinated Hydrocarbons and / or ethers are.

The invention accordingly provides for the use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as solvent, diluent nungsmittel, extractants, cleaning agents, degreasing agents, absorbents and / or dispersants.

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are slow-evaporating, high polar, aprotic and widely applicable organic solvents (Boiling point 1,4-dimethylpyrrolidone: 216 ° C / 1013 mbar, boiling point 1,3-dimethylpyrrolidone: 203 ° C / 1013 mbar) with favorable ecological and toxicological data. It is colorless, low viscosity Liquids with a weak amine smell. 1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are with water and most organic Solvents completely miscible.

In comparison with conventional solvents, 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are distinguished by a few salient features:
They are recyclable and non-corrosive, have a high flash point of 86 ° C, a high ignition temperature of 266 ° C and a low surface tension of 34.8 Nm / m (20 ° C), dissolve inorganic substances such as inorganic salts, separate aromatic from aliphatic compounds and are very readily biodegradable.

Examples for such inorganic substances are: sulfur, zinc chloride, Sodium nitrite, lithium nitrate, sodium bromide, mercuric chloride, some iron, copper and lead salts.

All The above features make 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a good or a best choice for a wide range of different applications (see below).

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are chemically stable and powerful polar solvents. These properties are different chemical reactions in which an inert medium of importance is, very valuable:

Reaction medium for the organic synthesis

in the Compared to other solvents carry 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone when used as a solvent in chemical reactions often desirable catalytic Effects and results in better sales. This advantageous Property is of great importance.

Alkylation of Acetylidene

The preparation of acetylides under mild conditions succeeds in 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, whereas for these products generally an alkylation of acetylenes in liquefied ammonia is required [vgl. for example: GE 944 311 (BASF, 1956)].

Reppe Chemistry

1,3-Dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are also advantageous as reaction media which offer better processing for ethynylation and vinylation under Reppe conditions [cf. for example: W. Chodkiewicz, Ann. de Chim. (Paris), 2 (13), 819 (1957) ; GE 940 981 (BASF), 1956)].

Synthesis of nitriles

By using 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a solvent in the Rosenmund-von-Braun nitrile synthesis, the yield is improved and the reaction time is shortened; Furthermore, all reactants are dissolved, so that a homogeneous liquid phase results [vgl. for example: MS Newman and DK Philipps, J. Am. Chem. Soc. 81, 3667 (1959) ].

reactions of synthesis gas in 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone Carboxylic acids, carboxylic anhydrides and carboxylic acid esters can by reaction of alcohols with synthesis gas (CO + Hz) using nickel or cobalt complexes in 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone.

Another method is the production of ethylene glycol from synthesis gas. By combining a Rhodiumcarbonyl species and 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone results in a solution with excellent activity and selectivity for the formation of ethylene glycol [comp. for example: Watanabe et al., J. Chem. Soc., Chem. Commun. (3), 227 (1986) ].

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, despite their stability play an active role in certain implementations, namely in the hydrolysis, oxidation, condensation, reaction with chlorinating agents, Polymerization and O-alkylation as well as related reactions.

According to the invention, 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are preferably also used in the following known processes in which they replace NMP (see, for example, the BASF AG brochure , BASF Intermediates', "N-Methylpyrrolidone (NMP)", No. CZ 3307 e-0291-2.0 (circa 1994) and the literature cited therein, which is hereby incorporated by reference):

A) Recovery of pure hydrocarbons in petrochemical processing

A Application for 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone consists in the extraction of hydrocarbons by extractive distillation. Here one uses the high solubility of hydrocarbons in 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and the The fact that differences in volatility in the presence of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone sometimes be increased considerably. Compared to other offer commercial solvents and extraction media 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone the following Advantages: no azeotropes are formed with hydrocarbons; 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are very heat and chemical resistant; and 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone have a favorable toxicological and ecological profile.

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are miscible in all proportions with water. This allows the setting of the method on the desired conditions and stripping the dissolved Hydrocarbons from the solvent. 1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone have a low vapor pressure associated high boiling point, causing losses in separation processes kept to a minimum on an industrial scale can be. The viscosity is the usual Use temperatures low, which favors the mass transfer.

acetylene

1,3-Dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone can be used successfully for the separation and purification of acetylene from cracking gas mixtures resulting from the partial combustion of saturated hydrocarbons [cf. for example: H. Höfermann et al., Chem. Industry 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. At ambient conditions, 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone dissolve many times their own volume of acetylene. Acetylene can be easily separated from the light key component carbon dioxide as well as 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) is converted into an acetylenic gas by the BASF immersion flame process [ Ullmann's Encyclopedia of Industrial Chemistry, 5th Ed., VCH Verlagsgesellschaft, Weinheim, Vol. A1, 107 (1985) ], quenching with water and removing coke deposits or quenching with oil, removing coke deposits and recovering heat. The purification of the resulting cracking gas consists of two stripping steps in which 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone can be used as selective solvents.

1,3-butadiene

In the production of ethylene by the steam cracking process and similar large-scale pyrolysis reactions, a C ₄ fraction is obtained as a by-product in large quantities. The butadiene content of these fractions is usually about 40 to 50 g / 100 g.

1,3-Dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are highly effective because of their excellent selectivity for the separation of butadiene from butene or from C ₄ -acetylenes. In the BASF butadiene process [ U. Wagner and HM Weitz, Ind. Eng. Chem. 62, 43 (1970) ; B. Hausdörfer, U. Wagner and HM Weitz, Chem.-Ing.-Techn. 40 (23), 1147 (1968) ; K. Volkamer et al., Petroleum, Coal, Natural Gas, Petrochem. 34 (8), 343 (1981) ] can be 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, which contains, for example, 5 to 10 g of water / 100 g, in a two-stage countercurrent gas scrubbing. This gives butadiene of SBR quality (SBR = styrene-butadiene rubber) or poly-cis quality. The concentration of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone in the obtained pure butadiene is at most 10 mg / kg (ppm). By the same procedure, one can also separate C ₄ olefins and C ₄ paraffins.

In the BASF extractive distillation process [ Ullmann's Encyclopedia of Industrial Chemistry, 5th Ed., VCH Verlagsgesellschaft, Weinheim, Vol. A4, 437 (1985) ; Linnhoff and W. Lenz, Chem. Ing. Techn. 59 (11), 851 (1987) ; CA Abstract No. 140: 78725, 2004 ; CA Abstract No. 138: 402099, 2003 ] from C ₄ hydrocarbon feeds a butadiene in high purity (99.5 to 99.9 g / 100 g) and high yields (98%). As an essential process step, one can use 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, which contains, for example, about 8 g of water / 100 g, as a selective solvent, for example in a two-stage extractive distillation.

isoprene

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 either by extractive distillation or by liquid-liquid extraction. As a rule, C ₅ cuts from pyrolysis reactions contain 15 to 20 g of isoprene / 100 g. The purity of the final product is high, e.g. Eg 99% [ H. Kröper and HM Weitz, Oil Gas J. 65 (2), 98 (1967 )].

aromatics

According to the LURGI-Arosolvan process, it is possible to extract aromatics from hydrocarbon mixtures, such as reformate or hydrogenated pyrolysis gas [ K. Eisenlohr, Petroleum and Coal 16, 523 (1963) ; E. Müller and G. Höhfeld, Petroleum and Coal 24, 573 (1971) ; E. Müller, chemist newspaper 95, 996 (1971) ; E. Muller, Chem. And Industry 11, 518-22 (1973) ; E. Müller, VT Process Engineering 8 (3), 88 (1974) ]. This gives a high yield of benzene, toluene, xylene and other aromatics with boiling points below 180 ° C. By adding selected additives to 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, a solvent mixture with optimum selectivity and high solubility is guaranteed. The latter term is defined as the ratio of the aromatic concentration in the solvent phase to the aromatic concentration in the hydrocarbon phase.

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone over others Solvents u. a. the advantage that the conditions due to the distillative separation of the extracted aromatics the favorable location of their boiling point are optimal. Advantageous is also that the phases under use the density difference can be separated quite quickly and that 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone at the temperatures used in the process chemically and thermally are stable.

In the Distapex process of LURGI GmbH, 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 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone. The same applies to toluene or xylene from the corresponding distillation phases. This process is particularly advantageous when the crude products are already available as separate B, T or X sections and the concentration of the aromatic compounds is over 70% [ IB Lane et al., Chem. Process Eng. 48 (1), 49 (1967) ; E. Müller, VT Process Engineering 14, 551 (1980) ]. It is also possible to separate mixtures of monocyclic and polycyclic alkyl-substituted or unsubstituted aromatics with a mixture of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and water [compare: Ohio Oil, US 2,943,122 (1960) ]. Furthermore, the separation of aromatic hydrocarbons from naphtha and kerosene with a boiling range of 30 to 300 ° C by selective extraction with 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and reextraction with a cosolvent [see: Metallgesellschaft, EP-A-87 832 (1983) ].

B) desulfurization of gases and separation of acidic compounds in gases

In natural or synthetic gases, high concentrations of acidic compounds are often present. Examples include hydrogen sulfide, carbon dioxide sulfide, carbon dioxide and organic sulfur compounds. Their separation can, apart from the use of a chemical process also preferably be carried out by physical washing in several stages with a mixture of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, alcohol and water [see: Metallgesellschaft, GB 938 392 (1963) and DE 2 250 169 (1974) ; EP-A-13177 ; CA Abstract No. 82: 60774, 1984 ; CA Abstract No. 76: 61312, 1984 ].

The difference between the Bunsen solubility coefficient for hydrogen sulphide and that for carbon dioxide is so great that these gases can easily be separated and recovered in pure form. G. Hochgesand, Ind. Eng. Chem. 62 (7), 32 (1970) ].

C) Lubricating oils

at 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. After that, the components with the best lubrication properties - the Isoparaffins - 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. Advantageous solvents for this purpose are 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone [cf. JD Bushnell and RT Fiocco, Hydrocarbon Proc. 59 (5), 119 (1980) ; A. Sequeira, PB Sherman, TU Donciere and EO McBride, Hydrocarbon Proc. 58 (9), 155 (1979) ].

In the refining process, the feed is fed to the bottom of the extraction column and allowed to flow in countercurrent to the degassed 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone. The column is thus designed as a multi-stage extraction zone. As a result of the equilibrium that arises in all stages, a refined product containing the paraffins is taken off at the top. The extract, the more soluble component th, that contains the aromatics and the other impurities, is withdrawn from the bottom of the column. For recovery of the 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone then both streams, the refined product and the extract, must be distilled at elevated temperature or reduced pressure. Finally, three separate parts are obtained: the practically 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone-free paraffins, the extracted impurities and 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, which in turn is the extractor's head can be returned.

1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are much better than furfural and phenol for the lube oil extraction process [cf. A. Sequeira et al., Hydrocarbon Proc. 58 (9), 155 (1979) ].

When Advantages of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone compared to other solvents are, for example called: 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are thermally and chemically stable, have favorable toxicological and ecological properties and excellent selectivity and are very good solvents in terms of raffinate yields.

D) plastic

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone may be used as solvent for natural and synthetic plastics, waxes, Resins, and various types of paints are used. They dissolve polymers, such as cellulose derivatives, polymethylmethacrylate, Polyamides, polyimides, polyesters, polystyrene, polyacrylonitrile, polyvinyl chloride, Polyvinyl pyrrolidone, polyvinyl acetate, polyurethanes, polycarbonates, Polyethersulfones, polysulfones, polyethers and numerous copolymers.

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are with the corresponding monomers and with conventional organic solvents and water miscible. Therefore, you can get the best possible solvent mixture for a given application.

The The following examples illustrate the advantages of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone with reference to possibilities for Solving problems that occur in the plastics industry can.

moldings

The Production of fibers, foils, ribbons etc. from linear High polymers often pose technological problems. The The difficulty is that it involves solvents or softeners that are not corrosive, physiologically compatible and are not flammable at the processing temperature. In cases of this Type are 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone very useful because it consists of polyamides, polyacrylonitrile, Polyvinyl chloride, polystyrene and cellulose triacetate highly concentrated Solutions or moldable masses can be produced. The same applies at elevated temperature for vinyl fluoride homopolymers and copolymers.

thanks their swelling and solubilizing effect can 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone also for cold welding be used by plastics.

synthetic fibers

aromatic Polyamides are excellent components for the production of films, fibers and yarns used for technical applications needed to provide extremely high strength. That in the industry as starting material preferred poly (p-phenylene terephthalamide) is by reaction of p-phenylenediamine and terephthalic acid dichloride in concentrated 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone solvent systems accessible. Aramid high performance fibers and yarns can from spinning solutions of polyp-phenylene terephthalamide) or other polyamide-based polymer compositions by conventional wet and dry spinning processes.

lithium chloride containing 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are solvents for the production of polymers from aromatic diamines and aromatic acid chlorides, such as isophthalic acid chloride, the fibers and coatings can form and are resistant to high temperatures.

polyacrylonitrile, that is insoluble in most organic solvents is, in 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone be dissolved with small amounts of lower aliphatic ketones. These solutions can be at relatively low Temperatures are spun into uniform fibers.

fibrous Poly (arylene ether) -poly (arylenterephthalat) block copolymers can be prepared using a solution of potassium carbonate and 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone by interfacial method getting produced.

Fibers of poly (arylacetylene) may be in or ganic solvents such as 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone wet spun. Urea can be condensed in 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone at temperatures above 150 ° C with diamines. The linear, uncrosslinked polyureas thus obtained have a high molecular weight and good mechanical properties and can be made into fibers. 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone dissolve both the polymers and the monomers at elevated temperatures, but the polymers precipitate on cooling the solution to room temperature. Therefore, 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are superior to a phenolic solvent because they simplify the process and improve the quality.

at the synthesis of high-melting polyureas from aromatic Diamines and aromatic diisocyanates are 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as non-corrosive, inert solvents for the condensation reaction and the subsequent Spinning.

mixtures of polyacrylonitrile with formylated polyvinyl alcohol in solution in 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and of Polyacrylonitrile with poly (alkyl-alpha-acylaminoacrylates) are stable; they do not separate and can become homogeneous, non-segmented Fibers with a high softening point and good dye affinity be spun.

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and mixtures thereof with tetrahydrofuran or phenol are suitable for the production of spinning solutions of vinyl chloride polymers, vinylidene chloride polymers and synthetic ones linearly condensed polyesters derived from polyethylene terephthalates derived. The solutions obtained are stable, gel not and have a low viscosity at high solids content. They allow the production of fibers and films with superior physical Properties for the production of textiles after wet or dry process.

membranes

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone may be used for the preparation be used by semipermeable membranes. These membranes will be used in separation processes such as ultrafiltration and reverse osmosis.

Polyethersulfone membranes can be prepared from multicomponent mixtures of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, water and the respective polymers [cf. G. Tkacik and L. Zeman, J. Membr. Sci. 31 (2-3), 273 (1987) ].

The Properties of polysulfone membranes are solved by solutions in 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and dimethyl sulfoxide and calcium chloride as a pore-forming agent.

In the preparation of reinforced polysulfone membranes, mixtures of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and polyethylene glycols may be used as the swelling agent [cf. X. Lu, C. Gao and X. Sun, Chem. Abstr. 104 (24) 208436v (1985) ].

Synthesis of polymers

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone allow the synthesis of new polymers and / or the synthesis of polymers under improvement their quality.

at The production of polyurethane foams catalyzes 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone to the foaming reaction highly hydrophilic, soft articles. In foamed polyetherurethanes act 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as Controller for ensuring open-cell structures. The properties of polyester urethane rubber solutions in the presence of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are advantageous.

linear Synthetic polyamides are in 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone at 150 to 200 ° C slightly soluble and at room temperature poorly soluble; The same applies to polycaprolactam and copolymers of caprolactam with, for example, N-vinylcaprolactam. This property allows the removal of impurities, such as unreacted monomers and colored substances Recrystallization.

polycondensation with the participation of aminocarboxylic acids and their lactams or Salts of polycarboxylic acids and polyamides can be carried out in phenol. When replacing this solvent by 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone man fibers or moldings with superior quality and simplifications of the production process.

at the preparation of linear, high-viscosity polyamides from β-lactams are solvents such as 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone very well suited. 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone dissolve the monomer and the activator and swell the precipitated polymer.

Become Acrylates or methacrylates in the presence of dipolar, aprotic Cocatalysts, such as 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, anionically polymerized, the proportion of syndiotactic increases Polymer, so that the products obtained a more regular Structure have. Due to the obtained improvements in heat resistance, Solvent resistance and mechanical Properties are these products as molding compounds and binders for Surface coatings.

The Handling of as a hardener for Epoxyetherharze well-known m-phenylenediamine at room temperature is much easier and less dangerous when in 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone is dissolved. This solution extends the pot life of the resin and affects the curing behavior Not. A solidified at low temperatures melt is when thawed again to a homogeneous liquid.

The Photohardening of acrylic epoxy resins can be achieved with N-vinylpyrrolidone as a reactive diluent and 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as an unreactive diluent be performed.

Amorphous polyacrylether, which are very temperature resistant, can be advantageously prepared using 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone. The use of weak bases avoids side reactions [cf. DK Mohanty et al., Polymer Preprints 25 (2), 19 (1984) ].

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone may be used as the reaction medium in the synthesis of high performance poly (phenylene sulfide) for the polymerization of p-dichlorobenzene and sodium sulfide be used.

The Ring-opening polymerization of poly (aminobenzoyl lactams) can in the solvent system 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and lithium chloride take place.

E) Surface coatings

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are non-corrosive high boilers with excellent solvent power and excellent Chemical resistance. Therefore improve 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone the properties of many surface coating systems. These effects are particularly favorable for stoving coatings, which are cured at relatively high temperatures. 1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone allow the preparation of highly filled paints and varnishes. Since they are the improve rheological properties, one receives paint with superior flow and superior opacity. The coatings are therefore more homogeneous and non-porous and show no cratering and a bigger one Chemical resistance and higher mechanical strength.

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are excellent solvents for most starting materials for coatings, such as acrylates, epoxy resins, polyurethanes, polyvinyl chloride systems, polyamide-imide-based wire enamels, aqueous basecoats and printing inks, z. For inkjet printers, such as water-resistant inkjet inks, optionally containing a UV-curable resin.

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are useful solvents for butadiene-acrylonitrile copolymers (eg, Perbunan N), used for lining tanks. The rubber solutions flow and run better than those obtained with ketones Solutions.

By Dissolving vinyl chloride-vinyl acetate copolymers in one Mixture of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and mononuclear aromatic hydrocarbons a solution used for film casting can be. Due to the synergistic effect between the solvents the solutions have a low viscosity and can be applied easily.

polyisocyanates with imide groups can be used in solvent systems dissolved with 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone become. These solutions can be used for gumming Connected and metal surfaces are used.

Drahtlacke

One important feature of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone in the manufacture of thermosetting paints for electrical insulation are her outstanding Dissolving power for polycarboxylic acids and their anhydrides, such as trimellitic acid and pyromellitic anhydride, and polymers having high aromatic content amide and carboxyl groups.

Thus, polyisocyanates containing amide groups are formed in the condensation reaction between 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone solutions of anhydrides of polybasic carboxylic acids and monomeric polyfunctional isocyanates. The baked enamels obtained give coatings with excellent mechanical and dielectric properties on copper conductors. from From the technical point of view, 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone have the advantage that they have a dual function: they serve as reaction medium in the preparation process and remain in the finished coating as a viscosity modifier. 1,3-Dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are useful as solvents for the resinous copolyesters in the reaction between a diimide (such as that obtained from trimellitic anhydride and 4,4'-diaminodiphenylmethane) and polyhydric alcohols (such as trishydroxyethyl isocyanurate (THEIC) or ethylene glycol). The solutions thus formed can be fired to very heat-resistant wire enamels. 1,3-Dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are also solvents for polyamide / polyimide stoving lacquers derived from the condensation of a tricarboxylic acid with aromatic and aliphatic diamines.

Solvent mixtures from 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and dicarboxylic acid esters are suitable for use in the manufacture of wire enamels Base of polyvinyl formal.

F) paint stripping and cleaning

by virtue of their high solvent power for plastics, Resins, oil and fat can be 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone with success as a component in paint removers, Detergents and degreasers are used. Their miscibility with water and most common organic solvents enables the production of highly effective products, which are targeted to different uses can. The ecological and toxicological data of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone cheap compared to most other solvents. 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are not corrosive. Mixtures containing 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and other solvents often show desirable synergistic effects.

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone may be used alone alone (pure) or in mixtures for the removal of oil, Coal deposits and other tarry polymeric residues Metal chambers, pistons and cylinders as well as for wet cleaning of Internal combustion engines are used.

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone may be part of mixtures which are used in industry for cleaning soiled metal parts and devices are used. Certain difficult to solve Polyurethanes are best made with mixtures of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and dicarboxylic acid esters cleaned.

mixtures of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone with others organic solvents and excipients are used for removal used by printing ink residues.

With Mixtures containing 1,3-dimethylpyrrolidone as a key ingredient and / or 1,4-dimethylpyrrolidone, one removes epoxides and similar chemically resistant coatings of steel surfaces as well as temporary coatings of parts of optical instruments.

Solvent mixtures, the 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as reactive Component included, are suitable for manufacturing a foam type paint remover for use in the removal of various paints, Clearcoats, air-drying lacquers and other coatings or coatings, in particular of relatively large surfaces, suitable is.

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone may be used for the formulation used by paint removers that are easy to handle, are environmentally friendly and reduce the risk of fire.

mixtures of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone for cleaning objects or surfaces, due to substances such as oil, grease, soot, paint and Adhesive are dirty, used by immersion in a bath become. An important field of application is in this context the degreasing of metals before further surface treatment, Coating or galvanization. Cleaning baths to use contain 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, Odor masking agents, surfactants and diluents. By using a water absorption preventing layer can significantly delay the water absorption of the cleaner become.

Products based on 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are suitable for use in the removal of weathered emulsion paints on exterior walls, for the renovation of interiors, for the removal of graffiti and for the ultrasonic cleaning of objects like lenses or dentures.

The following solvents can be used in combination with surfactants, thickeners, and other additives to develop high solvent and swelling systems:
Butanol, butyl acetate, butyl glycol acetate (1-buto xy ethyl acetate), gamma-butyrolactone, 2-ethylhexyl acetate, 1-methoxy-2-propyl acetate, nonanol, pentyl acetate, Solvenon PM (1-methyl-2-propanol) and tridecanol.

G) Plant protection

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone may be used as solvent or cosolvent for the formulation of active ingredients such as Insecticides, fungicides, herbicides, seed treatment products and bioregulators are used where high polar compounds required are. 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone be compared to other highly polar solvents preferred since they are used as solvents or Cosolvens in pesticide formulations, the growing crops exempt from the requirement for tolerance are and a favorable toxicological and ecological Own profile. They are particularly suitable for multicomponent systems.

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone form adducts with bacteriostats, such as substituted ureas, carbanilides, thiocarbamates, guanidines and salicylanilides. These products are bactericidal and allow a better control of the growth of bacterial cultures.

H) Pharmaceuticals

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone may be used as solvent or cosolvent for the formulation of pharmacological agents used because of their high polarity very good solution properties for lipophilic, show poorly permeable active ingredients. 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone become highly polar compared to others Preferred solvents, especially 2-pyrrolidone, because they do not dissolve gelatin and for that reason especially for the formulation of active ingredients in gelatine capsules and both soft and hard gelatin capsules are suitable.

I) Manufacture of electronic devices

For the production of integrated circuits (ICs) products with very high purity are required. 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, with electronics quality, in particular according to the method according to EP-A1-1 038 867 (BASF AG) or US 5,777,131 (BASF Corp.). This makes 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone excellent solvents for the electronics industry and PCB manufacturers. Mixtures of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone with common solvents can be used for the purification and degreasing of single crystal silicon wafers for ICs.

By the use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a diluent in polyamide-imide, urethane and epoxy resins you get a smooth surface. The slow one Evaporation rate of 1,3-dimethylpyrrolidone or 1,4-dimethylpyrrolidone allows the formation of very homogeneous coatings.

In microphotolithography (the key to production of electronic chips) show 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone excellent performance in developers of photohardenable polyimides and in photoresist strippers.

in the last production step, ICs with resins, such as epoxy molding compounds, encapsulated. This remains on the encapsulated IC chip or the terminal comb and on the encapsulation device Resin release ("flash") back. One can Perform a finishing step by removing the resin with 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, softened, so it's easy with compressed air or high pressure water can be washed away (chemical Entflashen). It will recommended this procedure immediately after molding and before to perform the post-curing.

On Printed circuit boards become semiconductors and other electrical components soldered. This must be a flux be used. After soldering must flux residues be removed to prevent corrosion. This can be done with solvent blends done the key ingredient 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone.

One Another field of application is the selective removal of polymer coatings from certain areas on circuit boards.

J) Production of electrodes

1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone can be used as a solvent for the preparation of Elektrodenslurries z. B. be used for lithium-ion batteries. Electrode slurries are highly viscous dispersion which contain, in addition to the solvent, a powdered battery active material (eg MCMB or LiCoO ₂ ), polymer binder (PVdF), graphite and carbon black. The highly viscous slurry is applied to a metal foil (Cu or Al) by means of a doctor blade method and then dried. The thus coated metal foil can be subsequently processed into a battery.

The solvents 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are preferred because they have the property that they can dissolve well in the Elektrodenslurries located (sparingly soluble) PVdF-based binder. This is necessary to achieve a good mechanical stability of the electrode.

K) absorption media

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone can be 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, find wide application.

at the processing of organic solvents containing Adhesives can be some of these solvents by Replace 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone to give to reduce the vapor concentration. PVC or ABS adhesives, mainly from 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and / or gamma-butyrolactone show a reduced risk of fire. Since both products are a relative low vapor pressure, the risk of inhalation becomes significant reduced.

L) colors and pigments

For Colors with azo compounds can diazotizable amine dispersions with 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, the dissolve the diazo and coupling components become. To improve the formation and durability of shades may be 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone in the dyeing of polyamide, acrylic, polyester fibers, fabrics, films and of polyester-cotton blends. In colors, lithographic inks and other protective or decorative Pigment coatings disperse 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone effectively many organic or inorganic Color pigments without increasing the water sensitivity of the film. 1% solvent (based on pigment) facilitates grinding and increases staining power due to pigment refining. 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone improve the stability against aging, resulting in reduced color drift and stabilize the system against flocculation and solidification.

M) Ink jet printing process

1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone can be used as a solvent replacement for NMP in inks for inkjet printing processes. NMP-based inks, for example, in the brochure "Dyes for Inkjet Inks", BASF AG, Technical Information, TI / P 317e, April 2000) described.

in the Inkjet printing is achieved by targeted shooting or distracting small ink droplet produces a printed image.

Inkjet printing distinguishes two methods:
CIJ (Continuous Ink Jet)
DOD (drop on demand, ie devices that shoot single drops.

At the CIJ process, the ink jet passes through a nozzle out of the printhead. This beam is via a piezoelectric Transducer located behind the nozzle modulates, so that a uniform decay (Rayleigh'scher Dropper drop) into individual drops is achieved. about a charging electrode, the drops thus formed are more or less strongly electrostatically charged. The 10 to 40 m / s fast Drops then fly through a larger one Deflection electrode, where - depending on their specific electric charge - be deflected sideways. Depending on Device type now get the loaded or the uncharged Drop on the substrate / product. Not needed drops are caught again on the printhead and again the ink cycle fed.

At the DOD method is usually used between rubble jet printers, piezo printers and pressure-valve printers differentiated.

Bubble jet printer produce tiny drops of ink with the help of a heating element, which the water is heated in the ink. It forms explosively a tiny bubble of steam, the pressure of an ink drop pressed out of the nozzle.

Piezo printer use the piezoelectric effect in piezoelectric ceramic elements, to deform under electrical tension to pressure ink through to press a fine nozzle. There is a drop formation the ink whose drop volume is about the size can be controlled by the applied electrical pulse.

at Pressure valve printers are individual valves on the nozzles attached, which open when a drop the nozzle should leave.

The ink used in ink-jet printers is generally water-based and has added additives. The inks are made high demands. These include: high contrast, heat resistance, light resistance, low viscosity, pH neutrality, high surface tension and short drying times (no Drying in the nozzles). Furthermore, the inks should be non-toxic and non-corrosive.

inks for example, for inkjet printers contain 3% dyes, 53% distilled water, 10% polyethylene glycol, 30% 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, residual additives.

inks For example, Rubble Jet printers contain 3% dye, 87% distilled water, 5-10% 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone and other solvents, such as glycerol or diethylene glycol.

N) NMP replacement

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone find according to the invention as NMP replacement in particular also use in the above-cited methods and operations regarding NMP.

O) Substitute for solvents

1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone can successfully and advantageously replace:
Dimethylformamide (DMF), in particular in aqueous coatings, methylene chloride, in particular during stripping of memory chips, perchlorethylene and trichlorethylene, in particular in vapor degreasing processes, chlorine-containing solvents (eg chlorinated hydrocarbons, in particular chlorinated C 1 -C 6 hydrocarbons, such as tetrachlorethylene and trichlorethylene) z. B. in ultrasonic cleaning method, sodium hydroxide solution when cleaning reactors z. To remove urethane residues, furfural phenol in lubricant extractions and glycol ethers, e.g. As in household and industrial cleaners and coatings, ethers such. For example, THF, diethylene glycol dialkyl ether, 1,2-diethoxyethane and 1,2-dimethoxyethane, e.g. B. in chemical reactions.

P) Miscellaneous

In addition, 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone find application
as a solvent for developers (photo / reproduction technology),
for the production of high-performance adhesives and technical adhesive removers,
as a solvent for slime control agents used in papermaking and paperboard production,
as a reaction medium or solvent in the synthesis of organic intermediates and pharmaceuticals,
as a solvent for coal extraction and oil refining,
as a component in fluids for the production of printing plates,
for the removal of impurities and adhesives, in particular on cyanoacrylate-based adhesives, of polymers, plastics (eg polymethacrylates), glass, metal, ceramic, stone and fiber surfaces and also of the skin.

1.3 dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone are used for the above, uses according to the invention in particular with a purity greater than 97 wt .-%, in particular of greater than 98% by weight, especially larger 99 wt .-%, z. B. greater than 99.8 or greater 99.9 wt .-%, used. These purities can be through single or multiple distillation or rectification can be achieved.

1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone with high purity for use according to the invention is in particular with the method according to EP-A-1 038 867 (BASF AG) and US-A-5,777,131 (BASF Corp.) (see below).

1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone with high purity for use in accordance with the invention is in particular with the method according to the EP patent application 08170701.0 (BASF AG) prepared from dicarboxylic acid and monomethylamine under hydrogenating conditions. Homogeneously catalyzed with Ru or Os compounds in WO-A-2005051907 described method for the preparation of dicarboxylic acids and monomethylamine are applied.

The preparation of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone can by reacting alpha- or beta-methylbutyrolactone with monomethylamine at elevated temperature and elevated pressure to release one molar equivalent of water, for. B. analog Ullmann's Encyclopedia of Industrial Chemistry, Vol. A22, 5th Ed., Page 459 (1993) , respectively.

The preparation of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone can also by methylation of alpha- or beta-methylpyrrolidone, z. B. with methanol, take place; see for example Chem. Abstract. 120: 191559 (RO-B1-102421) and Chem. Abstract. 118: 233,904 ( EP-A1-531 673 ) and DD-A1-267 729 ,

The preparation of 1,3-DMP from butadiene, monomethylamine and carbon monoxide is known. In NO-A-131545 (Sentralinstitutt for industrial Forskning) are described homogeneous catalytic variants with Ru or Os compounds as homogeneous catalysts and alkali metal or alkaline earth metal hydrides as additives.

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 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone, by treating the contaminated N-substituted lactams with an acidic, in particular macroporous, cation exchanger.

QUOTES INCLUDE IN THE DESCRIPTION

This list The documents listed by the applicant have been automated generated and is solely for better information recorded by the reader. The list is not part of the German Patent or utility model application. The DPMA takes over no liability for any errors or omissions.

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• - Chem. 120: 191559 (RO-B1-102421) [0118]

Claims (21)

Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a solvent, diluent, Extractants, detergents, degreasers, absorbents and / or dispersing agent. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as solvent and / or extractant in process for the decomposition of gas mixtures. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone according to the preceding claim, wherein the gas mixtures in cracking processes obtained from hydrocarbons. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone according to one of the two preceding claims for the separation of acetylene, 1,3-butadiene and / or aromatics. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a solvent for polymers and / or copolymers. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone according to the preceding claim, wherein it is the polymers and / or Copolymers to polymethylmethacrylate, polyester, polyacrylonitrile, Acrylonitrile-containing copolymers, butadiene-containing copolymers, styrene-containing copolymers, N-vinylpyrrolidone-containing copolymers, vinyl chloride-containing copolymers, Vinyl acetate-containing copolymers, methyl methacrylate-containing copolymers, terephthalic acid polyesters, Polyvinyl chloride, polyvinylpyrrolidone, polyvinyl acetates, polycarbonates, Polyethers, polyethersulfones, polystyrene, polyamides, polyimides and / or Polyurethanes act. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a solvent for resins, cellulose derivatives and dyes. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a solvent, diluent and / or Dispersants in chemical reactions. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone according to the preceding claim, wherein it is in the chemical reactions for C-C linking reactions and / or polymerizations is. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a solvent in processes for the production of wire enamels. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as solvent and / or absorbent in process for gas scrubbing. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone according to the preceding claim for the separation of SO ₂ , H ₂ S and / or vinyl chloride. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a solvent, cleaning agent and / or degreasing agent in methods of manufacturing integrated circuits (ICs). Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a solvent or co-solvent for the formulation of active substances such as insecticides, fungicides, herbicides, seed treatment products and bioregulators. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a solvent or co-solvent for the formulation of active pharmaceutical ingredients, especially for the formulation in Hard and soft gelatine capsules. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a solvent for the production of Elektrodenslurries for lithium-ion batteries. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone as a partial or complete replacement for N-methyl-2-pyrrolidone (NMP). Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone according to one of claims 1 to 13 as a partial or complete Replacement for chlorinated hydrocarbons and / or ethers. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone in inks for inkjet printers. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone according to any one of the preceding claims, wherein 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone in a purity of> 99 wt .-% used becomes. Use of 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone according to any one of the preceding claims, wherein 1,3-dimethylpyrrolidone and / or 1,4-dimethylpyrrolidone previously used with a acidic cation exchanger was treated.