WO2007115943A2 - Verfahren zur herstellung eines n-alkyl-lactams mit verbesserter farbqualität - Google Patents
Verfahren zur herstellung eines n-alkyl-lactams mit verbesserter farbqualität Download PDFInfo
- Publication number
- WO2007115943A2 WO2007115943A2 PCT/EP2007/053008 EP2007053008W WO2007115943A2 WO 2007115943 A2 WO2007115943 A2 WO 2007115943A2 EP 2007053008 W EP2007053008 W EP 2007053008W WO 2007115943 A2 WO2007115943 A2 WO 2007115943A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- alcohol
- weight
- ppm
- range
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/18—Stabilisation
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
Definitions
- the present invention relates to a process for the preparation of an N-alkyl-lactam with improved color quality and mixtures containing at least 99.0% by weight of an N-alkyl-lactam and in the range of 100 to 5000 ppm by weight of a Ci-10 Alcohol or an acetal, aminal or an orthoester, which releases in the range of 100 to 5000 ppm by weight of a Ci-10 alcohol.
- N-alkyl-lactams are important products in the chemical industry. Most widely used among them are N-alkyl-pyrrolidones (N-alkyl-5-membered ring lactams).
- N-alkyl-pyrrolidones are e.g. organic solvents that are used in a variety of applications.
- N-alkyl-pyrrolidones are thermally stable, chemically inert, colorless, low viscosity and aprotic solvents of wide applicability.
- NMP N-methylpyrrolidone
- NEP N-ethyl-pyrrolidone
- the higher homologues can be used as solvents, diluents, extractants, cleaning agents, degreasing agents, adsorbents and / or dispersants.
- NMP is used in the extraction of pure hydrocarbons in the petrochemical processing, in the purification and separation of gases such as acetylene 1, 3-butadiene or isoprene, in the aromatics extraction, for example in the Distapex process of LURGI GmbH, in the sour gas scrubbing and in the oil extraction.
- NMP can be used as a solvent for polymer dispersions, for example for polyurethane dispersions.
- NMP is also a good solvent for many plastics such as polyvinyl chloride (PVC), polyurethanes (PU), acrylates or butadiene-acrylonitrile copolymers and is used in their processing.
- PVC polyvinyl chloride
- PU polyurethanes
- acrylates or butadiene-acrylonitrile copolymers are also used in their processing.
- NMP is also used as a cleaning agent in the removal of paint and paint residues, as a paint stripper and as a cleaning agent for metal, ceramic, glass and plastic surfaces.
- NMP is solvent or cosolvent for the formulation of active ingredients in crop protection.
- NEP and other N-alkyl-pyrrolidones can replace NMP in many applications and, in addition, in many cases additionally show advantageous properties (WO-A-2005/090447, BASF AG).
- Other common N-alkyl-lactams are N-alkyl-piperidones and N-alkyl-caprolactams.
- N-alkyl-caprolactams, in particular N-methyl-caprolactam can be used as selective solvents for gas deacidification, as described in Chem. Techn. 29 (1977), pages 445-448 (Wehner et al., VEB Leuna).
- N-alkyl-caprolactams are also used in the extraction of hydrocarbons because of the high achievable selectivities, as described in Chem. Techn. 27 (1975), pages 401-405 (Wehner et al., VEB Leuna). Comp. also WO-A-05/092953 (BASF AG). N-alkylpiperidones, such as N-methyl-piperidone, may also be used in these applications.
- N-alkyl-pyrrolidones may be prepared by reacting gamma-butyrolactone ( ⁇ -BL) with monoalkylamines to release one equivalent of water, e.g. B. analogously to Ullmann 's Encyclopedia of Industrial Chemistry, Volume A22, 5th ed., P. 459 (1993) or analogously to DE-A-19 626 123 (BASF AG).
- ⁇ -BL gamma-butyrolactone
- monoalkylamines to release one equivalent of water
- ⁇ -BL gamma-butyrolactone
- ⁇ -BL gamma-butyrolactone
- N-alkyl-lactams such as N-alkyl-piperidones and N-alkyl-caprolactams
- monoalkylamines such as Yakugaku Zasshi 71 (1951), 1341 (Susagawa et al.). described.
- these lactams can also be obtained by reacting oxynitriles with monomethylamines, as disclosed in DE-A-1 1 92 208 (BASF AG), or also elegantly by reacting lactams with monoalcohols or
- Dialkyl ethers of acidic catalysts such as Al2O3, as described in Chem. Techn. 33 (1981), 193-196 (Wehner et al., VEB Leuna) or RO 137218 (sometimes deticianri] Fiber Chimice), or with other alkylating agents such as dialkyl sulfates or alkyl halides under basic conditions as described, for example, in J. Org. Chem. 29 (1964), pages 2748-2750 (Moriarty).
- N-alkyl-lactams Purification processes for N-alkyl-lactams are known.
- the purification of N-alkylpyrrolidones can be carried out, for example, by fractional distillation (also repeatedly, as described in JP 06 228 088 (Mitsubishi Kasei Corp.)) or by extraction.
- Other or additional purification steps may be treatment with ion exchangers, as described, for example, in EP-A-1 038 867 (BASF AG), or with solid adsorbents such as aluminum oxide analogously to WO-A-2005/092851 (Lyondell LP).
- N-alkylpyrrolidones can also be prepared in the presence of acids such as toluenesulphonic acid (described, for example, JP 1 1071 346 (Tonen Corp.)) or phosphoric acid (described, for example, in JP 2028148 (Ouchi Shinko Chem. )) are purified during the distillation.
- acids such as toluenesulphonic acid (described, for example, JP 1 1071 346 (Tonen Corp.)) or phosphoric acid (described, for example, in JP 2028148 (Ouchi Shinko Chem. )) are purified during the distillation.
- Other advantageous additives during the preparation and / or distillation can alkali, alkaline earth or Ammoniumborhydride such as in No. 4,885,371 (GAF Chemicals Corp.), oxidizing agents such as potassium permanganate, sodium perborate or potassium dichromate, as described in JP 72 22 225 (Teijin Ltd.
- JP-A-2001 089 446 (Mitsubishi Chem. Corp.) teaches that clean NMP can be obtained with low color if, during distillation, the amounts of hydrogen and oxygen have limits of 0.01 ⁇ mol% and 0.002 ⁇ mol%. do not exceed based on the Pyrrolidongehalt.
- JP 62 79 401 (Mitsubishi Kasei Corp.) colorless N-methyl-pyrrolidone can also be obtained by thermal treatment ("annealing" at 150-250 ° C) and subsequent distillation.
- N-alkyl-lactams such as N-alkyl-piperidones and N-alkyl-caprolactams, can be purified by analogous routes.
- N-alkyl-lactams for example the use of N-alkyl-pyrrolidones as solvents in the manufacture of paints and varnishes or adhesives, or in the production of plastics, it is important that these solvents be as colorless as possible, i. not yellowed form are used.
- N-alkylpyrrolidones tend to yellow when stored and then no longer come into question for such applications, since a part of the discoloration in the products such as paints or plastics is retained and is undesirable there.
- additives such as sodium borohydride during the synthesis of N-alkyl-pyrrolidones can lead to improved color properties nen. While many of these methods of improving color properties are described for cleaning and manufacturing processes, there are very few technical solutions to stabilize the product during storage.
- JP-A-2003 081 885 Mitsubishi Chem. Corp.
- JP-A-2003 081 885 Mitsubishi Chem. Corp.
- the thermal stability to decomposition at high temperatures (above 250 ° C.) of N-methylpyrrolidone can also be improved according to US Pat. No. 4,168,226 (Exxon Research & Engineering Co.) by adding up to 0.5% by weight of water , In these cases, the decomposition of NMP proceeds greatly slowed down.
- the present invention has for its object to provide a method for preventing and / or slowing the yellowing of N-alkyl-lactams during processing and storage. It was intended to provide an improved, economical, easy to use process for preparing an N-alkyl lactam of improved color quality, i. Reduction of discoloration and / or improvement in color stability, especially when stored, be found.
- N-alkyl-lactam with improved color quality was found, which is characterized in that the N-alkyl-lactam in the range of 0.01 to 10 wt .-% of a Ci-10-alcohol or a Compound which releases in the range of 0.01 to 10 wt .-% of a Ci-10-alcohol added.
- the process is preferably characterized in that the N-alkyl-lactam in the range of 0.02 to 2 wt .-%, in particular 0.03 to 1 wt .-%, particularly 0.03 to 0.5 wt. %, further particularly 0.03 to 0.2 wt .-%, more particularly 0.03 to 0.1 wt .-%, of a Ci-10-alcohol or a compound which is in the range of 0.02 to 2 wt .-%, in particular 0.03 to 1 Gew. -%, in particular 0,03 to 0,5 Gew. -%, further particularly 0,03 to 0,2 Gew. -%, further particularly 0,03 to 0, 1 wt .-%, a CMO alcohol releases added.
- the process according to the invention is preferably carried out at a temperature in the range from -20 to 400 ° C., in particular in the range from 0 to 350 ° C., more particularly in the range from 10 to 250 ° C.
- the lower limit of a preferred temperature range is 20, 50, 100, or 200 ° C
- the upper limit is 220 or 150 ° C.
- the exact mechanism of action of the alcohol additives is not yet known. According to the invention, all N-alkyl-lactams can be treated in this way.
- the lactam ring of the N-alkyl-lactams may, for. B. four to eight carbon atoms, preferably four (pyrrolidones), five (piperidones) or six (caprolactams), more preferably 2-pyrrolidones and 2-piperidones can be used.
- a linear or branched saturated aliphatic radical preferably Ci-12-alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n -Pentyl, iso-pentyl, sec-pentyl, neo-pentyl, 1, 2-dimethylpropyl, n-hexyl, iso -hexyl, sec-hexyl, cyclopentylmethyl, n-heptyl, iso-heptyl, cyclohexylmethyl, n-octyl , 2-ethylhexyl, n-nonyl, isononyl, n-decyl, isodecyl, n-undecyl, n-dodecyl, isododecyl, n
- n represents an integer of 1 to 5 and wherein the carbon atoms of the heterocyclic ring of the N-substituted lactam have one to two under the conditions inert substituents, for.
- B. alkyl radicals such as. B. Ci-8-alkyl radicals which are independent of one another, preferably a Ci-s-alkyl radical, especially a Ci-4-alkyl radical, can carry.
- Ci-s-alkyl radicals which can carry the carbon atoms of the heterocyclic ring of the N-substituted lactam are:
- 5-dimethyl-2-pyrrolidone and 1-ethyl-5-methyl-2-pyrrolidone iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl and 2-ethyl-hexyl, such as.
- 5-dimethyl-2-pyrrolidone and 1-ethyl-5-methyl-2-pyrrolidone 1-ethyl-5-methyl-2-pyrrolidone.
- N-alkyl-lactams of the formula I are particularly preferably used
- R is Ci-4-alkyl as described above and n is 1, 2 or 3 and wherein the carbon atoms of the heterocyclic ring of the N-substituted lactam can carry a C 1-4 -alkyl radical, especially methyl or ethyl radical.
- the N-alkyl-lactams used may have a purity of> 90 wt .-%, preferably> 95 wt .-%, more preferably> 99 wt .-%.
- N-alkyl-lactams Possible impurities of the N-alkyl-lactams are corresponding lactones (such as, for example, gamma-butyrolactone), corresponding N-unsubstituted lactams (for example pyrrolidone), organic peroxides, corresponding monoalkylamines (such as, for example, monoethylamine ), corresponding cyclic N-alkylimides (for example N-alkylsuccinimides), water, which may preferably be present in each case in amounts of ⁇ 1% by weight, are possible and not interfering.
- lactones such as, for example, gamma-butyrolactone
- N-unsubstituted lactams for example pyrrolidone
- organic peroxides corresponding monoalkylamines (such as, for example, monoethylamine )
- corresponding cyclic N-alkylimides for example N-alkylsuccinimides
- Alcohols which are added or liberated to increase the color stability are all alcohols having one or more hydroxyl function (s), in particular those having 1 to 10, preferably 1 to 8 carbon atoms, more preferably 1 to 3 carbon atoms, very particularly preferably 1 to 2 carbon atoms.
- Preferred monofunctional (monohydric) alcohols are methanol, ethanol, n-propanol, isopropanol, n-butanol, n-pentanol, n-hexanol, n-heptanol and n-octanol.
- Particularly effective polyfunctional (polyhydric) alcohols are 1, 2-ethylene glycol, 1, 2-propanediol, 1, 3-propanediol, glycerol, pentaerythritol and sorbitol.
- Very particularly preferred added or released alcohols are methanol and 1,2-ethylene glycol.
- alcohol sources hereinafter also referred to as alcohol precursors include, for. Dimethoxymethane, diethoxymethane, tetramethoxymethane, tetraethoxymethane, trimethyl orthoformate and triethyl orthoformate, e.g. release by hydrolysis alcohols and esters or alcohols and formaldehyde.
- a mixture of the alcohols and / or alcohol precursors can be used.
- the purity of the added alcohols or alcohol precursors is not critical and impurities such. As water, ether, esters and hydrocarbons are tolerated.
- the alcohol addition or alcohol precursor addition can be done in several ways, for example, the alcohols and / or alcohol precursors can be added to the N-alkyl-lactam directly after its synthesis and after or during the purification of the lactam. Likewise, an addition during filling of the lactam in storable or transportable containers is possible. The addition of the alcohols or alcohol precursors can be carried out either batchwise or continuously.
- the invention also relates to the above statements
- mixtures containing at least 99.0 wt .-%, preferably> 99.2 wt .-%, particularly> 99.5 wt .-%, 1, 5-dimethyl-2-pyrrolidone and in the range of 100 to 5000 wt. ppm, preferably 200 to 2000 ppm by weight, especially 300 to 1000 ppm by weight, of methanol or 1,2-ethylene glycol,
- mixtures containing at least 99.0 wt .-%, preferably> 99.2 wt .-%, particularly> 99.5 wt .-%, 1-ethyl-5-methyl-2-pyrrolidone and in the range of 100 to 5000 Ppm by weight, preferably from 200 to 2000 ppm by weight, especially from 300 to 1000 ppm by weight, of methanol or 1,2-ethylene glycol,
- mixtures containing at least 99.0 wt .-%, preferably> 99.2 wt .-%, particularly> 99.5 wt .-%, 1-methyl-2-piperidone and in the range of 100 to 5000 ppm by weight , preferably 200 to 2000 ppm by weight, especially 300 to 1000 ppm by weight, methanol or 1, 2-ethylene glycol.
- the APHA color numbers were determined according to DIN EN ISO 6271.
- GC method for determining the purity of the N-alkyl-lactams The lactams were injected undiluted into the GC chromatograph (HP, carrier gas: hydrogen) onto a 30 m DB5 column (J + W) and at oven temperatures from 60 ° C to 260 ° C (heating rate 16 Kelvin per minute to 220 ° C, then 20 Kelvin per minute to 260 ° C) with a flame ionization detector (temperature: 290 ° C) analyzed. The purity was determined by integration of the signals of the chromatogram.
- HP carrier gas: hydrogen
- N-ethyl pyrrolidone 250 ml, 99.69% purity by GC, Hazen color number: 12 APHA
- methanol 500 ppm
- methanol 500 ppm
- the purity had decreased (to 97.55% by GC), while the color number had increased to 208 APHA.
- N-ethylpyrrolidone 250 ml, purity 99.69% by GC, Hazen color number: 12 APHA
- 1,2-ethylene glycol 500 ppm
- the purity had decreased (to 97.66% by GC), while the color number had increased to 176 APHA.
- N-ethyl-pyrrolidone 250 ml, purity 99.69% according to GC, Hazen color number: 7 APHA was heated without additives in a 500 ml glass flask with attached reflux condenser and drying tube in the presence of air at 100 ° C. After 72 hours, the purity had decreased (to 97.77% by GC), while the color number had increased to 284 APHA.
- N-ethylpyrrolidone (10 ml, purity 99.59% by GC, Hazen color number: 7 APHA) was added with dimethyoxymethane (500 ppm). The mixture was heated to 100 ° C in a gas-tight sealed 20 ml glass autoclave. After 72 hours (h), the purity had decreased (to 99.37% by GC), while the color number had risen to 22 APHA.
- N-ethyl-pyrrolidone (10 ml, purity 99.59% according to GC, Hazen color number: 7 APHA) was heated to 100 ° C. without additions in a gas-tight 20 ml glass autoclave. After 72 hours (h), the purity had decreased (to 99.27% by GC), while the color number had risen to 32 APHA.
- Example 4 N-ethyl-pyrrolidone (10 ml, purity 99.59% according to GC, Hazen color number: 7 APHA) was heated to 100 ° C. without additions in a gas-tight 20 ml glass autoclave. After 72 hours (h), the purity had decreased (to 99.27% by GC), while the color number had risen to 32 APHA.
- N-methyl-piperidone (10 ml, purity 99.20% by GC, Hazen color number: 18 APHA) was added with methanol (500 ppm). The mixture was heated to 100 ° C in a gas-tight sealed 20 ml glass autoclave. After 72 hours (h), the purity had decreased (to 98.82% by GC) while the color number had increased to 172 APHA.
- N-methyl-piperidone (10 ml, purity 99.20% according to GC, Hazen color number: 18 APHA) was heated to 100 ° C. without additions in a gas-tight 20 ml glass autoclave. After 72 hours (h), the purity had decreased (to 98.73% by GC), while the color number had risen to 197 APHA.
- 1,5-Dimethyl-2-pyrrolidone (10 ml, purity 99.72% according to GC, Hazen color number: 5 APHA) was mixed with methanol (500 ppm). The mixture was heated to 100 ° C in a gas-tight sealed 20 ml glass autoclave. After 72 hours (h), the purity had decreased (to 99.53% by GC) while the color number had increased to 404 APHA.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/296,115 US20090182139A1 (en) | 2006-04-06 | 2007-03-29 | Process for the preparation of an n-alkyl lactam with improved colour quality |
EP07727480A EP2004599B1 (de) | 2006-04-06 | 2007-03-29 | Verfahren zur Herstellung eines Nn-Alkyl-Lactams mit verbesserter Farbqualität |
JP2009503543A JP5264704B2 (ja) | 2006-04-06 | 2007-03-29 | 改善された色品質を有するn−アルキルラクタムの製造方法 |
AT07727480T ATE532767T1 (de) | 2006-04-06 | 2007-03-29 | Verfahren zur herstellung eines nn-alkyl-lactams mit verbesserter farbqualität |
KR1020087027088A KR101431845B1 (ko) | 2006-04-06 | 2007-03-29 | 개선된 색상 품질을 갖는 n-알킬락탐의 제조 방법 |
CN2007800121273A CN101415673B (zh) | 2006-04-06 | 2007-03-29 | 制备具有改进的颜色质量的n-烷基内酰胺的方法 |
US12/842,263 US20100286399A1 (en) | 2006-04-06 | 2010-07-23 | Process for the preparation of an n-alkyl lactam with improved colour quality |
US12/842,228 US20100286411A1 (en) | 2006-04-06 | 2010-07-23 | Process for the preparation of an n-alkyl lactam with improved colour quality |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06112323.8 | 2006-04-06 | ||
EP06112323 | 2006-04-06 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/842,263 Division US20100286399A1 (en) | 2006-04-06 | 2010-07-23 | Process for the preparation of an n-alkyl lactam with improved colour quality |
US12/842,228 Continuation US20100286411A1 (en) | 2006-04-06 | 2010-07-23 | Process for the preparation of an n-alkyl lactam with improved colour quality |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2007115943A2 true WO2007115943A2 (de) | 2007-10-18 |
WO2007115943A3 WO2007115943A3 (de) | 2008-03-27 |
Family
ID=38581447
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/053008 WO2007115943A2 (de) | 2006-04-06 | 2007-03-29 | Verfahren zur herstellung eines n-alkyl-lactams mit verbesserter farbqualität |
Country Status (7)
Country | Link |
---|---|
US (3) | US20090182139A1 (de) |
EP (1) | EP2004599B1 (de) |
JP (1) | JP5264704B2 (de) |
KR (1) | KR101431845B1 (de) |
CN (1) | CN101415673B (de) |
AT (1) | ATE532767T1 (de) |
WO (1) | WO2007115943A2 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010057917A1 (en) * | 2008-11-24 | 2010-05-27 | Basf Se | Process for preparing an n-alkyllactam with improved color quality |
EP2804940A1 (de) | 2012-01-17 | 2014-11-26 | Taminco | Verwendung von n-alkyl-pyrrolidonlösungsmitteln |
WO2021119004A1 (en) * | 2019-12-11 | 2021-06-17 | Advansix Resins & Chemicals Llc | Process for the synthesis of n-substituted lactams and amides |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103069294B (zh) * | 2010-08-11 | 2014-07-09 | 丰田自动车株式会社 | 矫顽力分布磁体的矫顽力性能判定装置 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2964535A (en) * | 1957-07-22 | 1960-12-13 | Monsanto Chemicals | Purification of nu-methyl pyrrolidone |
DE1785124A1 (de) * | 1968-08-13 | 1971-11-11 | Prym Werke William | Reissverschluss |
CH547805A (de) * | 1970-10-01 | 1974-04-11 | Inventa Ag | Verfahren zur reinigung von lactamen. |
US4168226A (en) * | 1977-04-08 | 1979-09-18 | Exxon Research & Engineering Co. | Thermal stabilization of N-methyl-2-pyrrolidone |
JPS61191674A (ja) * | 1985-02-20 | 1986-08-26 | Mitsubishi Chem Ind Ltd | N−メチルピロリドンの分離回収法 |
US4812951A (en) * | 1987-03-20 | 1989-03-14 | Aerovox M, Inc. | Electrolytic capacitor and electrolyte therefor |
US4885371A (en) * | 1989-06-22 | 1989-12-05 | Gaf Chemicals Corporation | Process for the preparation of purified N-alkyl lactams |
US5496491A (en) * | 1991-01-25 | 1996-03-05 | Ashland Oil Company | Organic stripping composition |
JP2936949B2 (ja) * | 1993-03-26 | 1999-08-23 | 三菱化学株式会社 | N−メチル−2−ピロリドンの精製方法 |
JP2701731B2 (ja) * | 1994-01-31 | 1998-01-21 | 日本電気株式会社 | コンピュータ接続対応無線選択呼出受信機 |
FR2734819B1 (fr) * | 1995-05-31 | 1997-07-04 | Adir | Nouveaux composes de la piperazine, de la piperidine et de la 1,2,5,6-tetrahydropyridine, leur procede de preparation et les compositions pharmaceutiques les contenant |
US5663135A (en) * | 1995-08-10 | 1997-09-02 | Corpex Technologies, Inc. | Terpene-based cleaning composition |
US5777131A (en) * | 1995-11-21 | 1998-07-07 | Basf Corporation | Post manufacture process for improving the properties of lactones and substituted lactams |
JP3629831B2 (ja) * | 1996-08-13 | 2005-03-16 | Jsr株式会社 | 液晶配向剤および液晶表示素子 |
US5853794A (en) * | 1997-10-31 | 1998-12-29 | Kemet Electronics Corp. | Doped polyaniline solutions |
US5966804A (en) * | 1997-11-03 | 1999-10-19 | National Center For Manufacturing Sciences | Printed wiring board assemblies |
DE19910504A1 (de) * | 1999-03-10 | 2000-09-14 | Basf Ag | Verfahren zur Reinigung von N-substituierten Lactamen |
AU2001247848A1 (en) * | 2000-03-31 | 2001-10-15 | Michigan State University | Process for the preparation of 1,5-dideoxy-1,5-imino hexitols from oximes or imines |
US20020036158A1 (en) * | 2000-08-08 | 2002-03-28 | Austin Douglas P. | Batch process for refining used oil |
DE10129336A1 (de) * | 2001-06-19 | 2003-01-02 | Basf Ag | Verfahren zur Herstellung von Pyrrolidonen |
EP1727844B1 (de) * | 2004-03-15 | 2009-01-07 | Basf Se | N-ethylpyrrolidon in der herstellung von polyurethandispersionen |
GB0412875D0 (en) * | 2004-06-09 | 2004-07-14 | Davy Process Techn Ltd | Process |
US20060128589A1 (en) * | 2004-12-09 | 2006-06-15 | Bg Products, Inc. | Low VOC air intake system cleaner |
JP3956977B2 (ja) | 2005-03-29 | 2007-08-08 | コニカミノルタビジネステクノロジーズ株式会社 | 画像処理装置、画像処理方法、画像処理プログラム、及び、記録媒体 |
-
2007
- 2007-03-29 KR KR1020087027088A patent/KR101431845B1/ko not_active IP Right Cessation
- 2007-03-29 JP JP2009503543A patent/JP5264704B2/ja not_active Expired - Fee Related
- 2007-03-29 CN CN2007800121273A patent/CN101415673B/zh not_active Expired - Fee Related
- 2007-03-29 WO PCT/EP2007/053008 patent/WO2007115943A2/de active Application Filing
- 2007-03-29 EP EP07727480A patent/EP2004599B1/de active Active
- 2007-03-29 US US12/296,115 patent/US20090182139A1/en not_active Abandoned
- 2007-03-29 AT AT07727480T patent/ATE532767T1/de active
-
2010
- 2010-07-23 US US12/842,263 patent/US20100286399A1/en not_active Abandoned
- 2010-07-23 US US12/842,228 patent/US20100286411A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
None |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010057917A1 (en) * | 2008-11-24 | 2010-05-27 | Basf Se | Process for preparing an n-alkyllactam with improved color quality |
EP2804940A1 (de) | 2012-01-17 | 2014-11-26 | Taminco | Verwendung von n-alkyl-pyrrolidonlösungsmitteln |
WO2021119004A1 (en) * | 2019-12-11 | 2021-06-17 | Advansix Resins & Chemicals Llc | Process for the synthesis of n-substituted lactams and amides |
CN115244032A (zh) * | 2019-12-11 | 2022-10-25 | 艾德凡斯化学公司 | 合成n-取代内酰胺和酰胺的方法 |
US11618732B2 (en) | 2019-12-11 | 2023-04-04 | AdvanSix Resins & Chemical LLC | Process for the synthesis of n-substituted lactams and amides |
Also Published As
Publication number | Publication date |
---|---|
WO2007115943A3 (de) | 2008-03-27 |
KR101431845B1 (ko) | 2014-08-25 |
CN101415673B (zh) | 2011-02-02 |
CN101415673A (zh) | 2009-04-22 |
US20090182139A1 (en) | 2009-07-16 |
US20100286411A1 (en) | 2010-11-11 |
JP5264704B2 (ja) | 2013-08-14 |
JP2009532420A (ja) | 2009-09-10 |
EP2004599A2 (de) | 2008-12-24 |
EP2004599B1 (de) | 2011-11-09 |
US20100286399A1 (en) | 2010-11-11 |
KR20090023557A (ko) | 2009-03-05 |
ATE532767T1 (de) | 2011-11-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1945602B1 (de) | Hydrogen katalysiertes verfahren zur herstellung von (meth)acrylaten von n-hydroxyalkylierten lactamen | |
EP2004599B1 (de) | Verfahren zur Herstellung eines Nn-Alkyl-Lactams mit verbesserter Farbqualität | |
EP3048097A1 (de) | Verfahren zur herstellung einer n-methylsubstituierten triacetonaminverbindung | |
EP2651861A1 (de) | Verfahren zur herstellung eines n,n-dialkyl-ethanolamins mit hoher farbstabilität | |
DE60104398T2 (de) | Verfahren zur herstellung von triethanolamin und nach dem verfahren erhaltenes produkt | |
DE4203527A1 (de) | Verfahren zur herstellung von pyrrolidon und n-alkylpyrrolidonen | |
EP0581115B1 (de) | Verfahren zur Abtrennung von Methanol aus Dimethylcarbonat/Methanol-Gemischen | |
EP2602247B1 (de) | Verfahren zur Reinigung von N-alkyl-substituierten Pyrrolidonen durch Hydrierung | |
EP2373617B1 (de) | Mischungen aus itaconsäure oder itaconsäurederivaten und primären aminen zur herstellung von 1,3- und 1,4-alkylmethylpyrrolidonen | |
EP1240140B1 (de) | Verfahren zur herstellung von n-alkenyl-amiden | |
EP2070912B1 (de) | Verfahren zur Vinylierung von Amiden | |
WO2002102773A1 (de) | Verfahren zur herstellung von pyrrolidonen | |
DE2758391A1 (de) | Verfahren zur verarbeitung eines benzylbenzoathaltigen teeres | |
WO2008098885A1 (de) | Katalytisches verfahren zur herstellung von (meth)acrylsäureestern von n-hydroxyalkylierten lactamen | |
EP2121559B1 (de) | Katalytisches verfahren zur herstellung von (meth)acrylsäureestern von n-hydroxyalkylierten lactamen | |
EP0697399B1 (de) | Verfahren zur Herstellung von N-Alkenylcarbonsäureamiden | |
DE19962405A1 (de) | Verfahren zur Herstellung von N-Alkenyl-amiden | |
EP0838454B1 (de) | Verfahren zur Acetylierung sterisch gehinderter Diamine | |
DE3506473A1 (de) | Verfahren zur herstellung von n,n-verknuepften bis-lactamverbindungen | |
EP2602246A1 (de) | Verfahren zur Reinigung von N-alkyl-substituierten Pyrrolidonen | |
WO2005087711A1 (de) | Verfahren zur herstellung von acetamid-acetalen | |
DE1770351A1 (de) | Neue Lincomycinderivate und Verfahren zu ihrer Herstellung | |
DE2937815A1 (de) | Verfahren zur herstellung von 3,3-dimethyl-pent-4-en-saeureamiden | |
WO1999010336A1 (de) | 2-(1,4-dioxan-2-on-3-yl)-essigsäureester | |
DEF0014057MA (de) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 07727480 Country of ref document: EP Kind code of ref document: A2 |
|
DPE1 | Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 12296115 Country of ref document: US Ref document number: 2009503543 Country of ref document: JP Ref document number: 200780012127.3 Country of ref document: CN Ref document number: 2007727480 Country of ref document: EP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 6000/CHENP/2008 Country of ref document: IN Ref document number: 1020087027088 Country of ref document: KR |