Production of caprolactam by thermal depolymerization of polyamide 6
Applications of Thermal Depolymerization. Thermal depolymerization is an industrial process of breaking down various waste materials into crude oil products. The materials are subjected to high temperatures and pressure in the presence of water, thereby initiating hydrous pyrolysis. Thermal depolymerization of biomass with emphasis on gasifier design and best. The BFB reactor chamber generally has a cylindrical configuration in which.
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- US5233037A US5233037AUS07/930,365US93036592AUS5233037AUS 5233037 AUS5233037 AUS 5233037AUS 93036592 AUS93036592 AUS 93036592AUS 5233037 AUS5233037 AUS 5233037A
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- Werner Nielinger
- Karsten-Josef Idel
- Hans-Josef Buysch
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- abstractdescription229930012949CaprolactamNatural products0claimstitle20
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- claims150000003951lactamsChemical class0239000002609mediaSubstances0239000000155meltsSubstances0238000000034methodsMethods0claims239000000203mixturesSubstances0229910052757nitrogenInorganic materials0description3
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- C--CHEMISTRY; METALLURGY
- C07D--HETEROCYCLIC COMPOUNDS
- C07D201/02--Preparation of lactams
- It has now been found that a caprolactam can be obtained in a high yield when depolymerization of the polyamide is carried out with potassium carbonate as catalyst and the caprolactam is distilled off in vacuo.Accordingly, the present invention relates to a process for the product of ε-caprolactam from polyamide 6 by depolymerization, in which the polyamide is heated in an inert gas atmosphere, preferably of nitrogen, to temperatures of 250° to 320° C. and preferably to temperatures of 270° to 300° C. in the presence of 0.5 to 2.5% by weight potassium carbonate and the caprolactam eliminated is distilled off under a reduced pressure of ≦100 mbar, preferably 15 to 100 mbar and, more preferably, 20 to 90 mbar and the caprolactam distilled off is fractionated once more, optionally in the presence of additives.Surprisingly, the use of potassium carbonate instead of sodium carbonate considerably increases the depolymerization rate of polyamide 6 and the yield of caprolactam. It is thus possible to reduce the temperature for the same throughput which results in a lighter colored and less contaminated product. After fractionation, this product may be reused for the production of high molecular weight polyamides without oxidation with potassium permanganate. Since neither water nor steam is added during the depolymerization process, there is no need for the removal of water before or during fractionation of the caprolactam.The process can also be applied to polyamide 6 containing glass fibers and fillers and also to products containing impact modifiers.In the context of the invention, polyamide 6 is understood to be pure polyamide 6 and also polyamides of which more than 50% by weight and preferably more than 80% by weight are based on polyamide 6.In the process according to the invention ε-caprolactam is obtained in a high yield, although it may require further purification for reaction to form high molecular weight polyamides. Purification processes for lactams are known, such as for example oxidation of aqueous lactams are known, such as for example oxidation of aqueous lactam solutions with potassium permanganate (JA 52108-991) or fractional distillation using acids or bases (DE 745224). These processes are costly and complicated and do not always produce satisfactory results. For example, in the polymerization of ε-caprolactam obtained by thermal depolymerization of non-modified polyamide 6 a relative viscosity of only 2.3 is obtained which may increase to 3.5 after the distillation of the lactam using phosphoric acid. These products are not suitable for the production of very high molecular weight polyamides.It has been found that it is possible to obtain ε-caprolactam which can be reacted to form high molecular weight polyamides with a relative viscosity of >3.5 without any further purification steps if the eliminated ε-caprolactam is distilled out of the reaction mixture in vacuo immediately after its formation until the distillate contains no more than 0.2, and preferably no more than 0.03 mmol, of basic constituents in one gramme of distillate. The determination of the basic constituents is carried out by acid-base titration of the lactam distillate with HCl.The invention thus also relates to a process for the production of highly pure ε-caprolactam from polyamide 6, characterized in that the ε-caprolactam obtained in the above-described depolymerization process is distilled off immediately after its formation at a reduced pressure of ≦100 mbar, and preferably 15 to 100 mbar, and particularly preferably at 20-90 mbar, until the distillate contains no more than 0.2, and preferably no more than 0.03 mmol, of basic constituents in one gramme of distillate.This result is also surprising and was not predictable since the fractional distillation of ε-caprolactam obtained by thermal depolymerization results in a polyamide with a relative viscosity of no more than 2.5, which is thus not suitable for many practical applications.The determination of the basic constituents is carried out by acid-base titration of an approximately 2% aqueous solution of the ε-caprolactam distillate with 1N hydrochloric acid using a Mettler titrator DL 25.The invention also relates to the use of the highly pure ε-caprolactam produced by the process according to the invention for the production of polyamides with a high molecular weight and a relative viscosity of >3.5, characterized in that the ε-caprolactam obtainable from the process is polymerized directly without any further purification stages.
EXAMPLE 1 In a round-bottomed flask, 40 g polyamide 6 having a relative viscosity of 3.1 (as measured on a 1% solution in m-cresol at 25° C. in an Ubbelohde viscosimeter) and 0.86 g potassium carbonate (2.15%) are heated under nitrogen to 320° C. (bath temperature). The melt is stirred and, after reaching the bath temperature, the pressure is reduced in steps to 25 mbar. The caprolactam begins to distill off at around 60 mbar and distillation is terminated after about 30 minutes. A colorless distillate is obtained in a yield of 92%. If 0.43 g potassium carbonate (1.08%) is used, a time of about 55 minutes is required for distillation.EXAMPLE 2 In a stirred tank reactor of stainless steel, a mixture of 2.1 kg polyamide 6 having a relative viscosity of 3.1 and 36.3 g potassium carbonate are heated by means of a heat-transfer medium having a temperature of 320° C. After the temperature of the polyamide melt has reached 290° C., the caprolactam formed is distilled off in vacuo.A colorless, 97-98% pure distillate, which is fractionated once more, is obtained in a yield of 95%.EXAMPLE 3 150 g of polyamide 6 having a relative viscosity of 3.1 (measured in an Ubbelohde viscosimeter at 25° C. using a 1% solution in m-cresol) and 2.59 g of potassium carbonate are heated to 300° C. (bath temperature). 5 minutes after this temperature is reached the vessel is carefully evacuated while intensively stirring the melt. In the course of 80 to 90 minutes a colorless distillate is obtained at 18 mbar in a yield of 93%. The distillate contains 0.17 mmol of base per gramme of distillate.Hydrolytic polymerization of the distillate produces an almost colorless polyamide with a relative viscosity of 2.4.EXAMPLE 4 Example 4 demonstrates the dependence of the formation of basic products on time. If the depolymerization of polyamide 6 is carried out as described in example 3, but with the difference that the melt is kept at 300° C. for one hour until the vacuum is applied, a content of basic constituents of 0.24 mmol/g is obtained. The relative viscosity of a polyamide obtained therefrom is 2.2.EXAMPLE 5 Example 3 is repeated with the distinction that the distillate is subjected once again to fractional distillation prior to hydrolytic polymerization. The content of basic constituents in the distillate is only slightly less after fractionation. The relative viscosity of the polyamide produced from the fractionated ε-caprolactam is 2.5.EXAMPLES OF HIGHLY PURE ε-CAPROLACTAM EXAMPLE 6 Example 3 is repeated with the distinction that during the depolymerization process the first distillate quantity of 40 g is removed and hydrolytic polymerization is carried out without any further purification of the ε-caprolactam, as described in comparative example 1. Using hydrochloric acid, 0.0086 mmol of base was detected in 1 g of distillate. The polyamide produced therefrom is a colorless product having a relative viscosity of 4.5. In the hydrolytic polymerization of commercially available ε-caprolactam a polyamide with a relative viscosity of 4.5 is also obtained under comparable conditions.EXAMPLE 7 Example 6 is repeated, except that the ε-caprolactam is collected until the distillate consumes 0.016 mmol of hydrochloric acid per g of distillate in the titration.After hydrolytic polymerization of the lactam a colorless polyamide with a relative viscosity of 4.0 is obtained.Claims (5)
We claim: 1. A process for the production of ε-caprolactam by depolymerization of polyamide 6 by alkali-catalyzed depolymerization, characterized in that the polyamide 6 is heated with 0.5 to 2.5% by weight potassium carbonate to 250° to 320° C. in an inert gas atmosphere and the ε-caprolactam eliminated is distilled off under a reduced pressure of ≦100 mbar and the distillate is fractionated.2. A process for the production of caprolactam as claimed in claim 1, characterized in that glass-fiber-containing or filler-containing polyamide 6 or impact-modified polyamide 6 is used.3. A process as claimed in claim 1, characterized in that 0.5 to 2.15% by weight potassium carbonate is used and/or the polyamide 6 is heated to 265°-300° C. and/or the ε-caprolactam eliminated is distilled off at 12 to 100 mbar.4. A process as claimed in claim 1, characterized in that the polyamide 6 is heated with 0.5 to 2.0% by weight potassium carbonate to 265°-300° C. in a nitrogen atmosphere and the -caprolactam eliminated is distilled off at 20-80 mbar and the distillate is fractionated.5. A process for the production of ε- caprolactam by depolymerization of polyamide 6 by heating the polyamide with 0.3 to 10% by weight potassium carbonate to 250°-300° C. under reduced pressure, characterized in that the ε-caprolactam is distilled off immediately after it is formed so that its content of bases is no more than 0.2, and preferably no more than 0.03 mmol/g distillate.US07/930,3651991-08-301992-08-17Production of caprolactam by thermal depolymerization of polyamide 6 Expired - Fee RelatedUS5233037A (en) Priority Applications (4)
Application Number Priority Date Filing Date Title DE4128788 1991-08-30 DE4211609 1992-04-07 Publications (1)
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Country Link EP (1) EP0529470A1 (en) DE (1) DE4211609A1 (en) Cited By (9)
* Cited by examiner, † Cited by third party Publication number Priority date Publication date Assignee Title US5504267A (en) * 1992-04-06 1996-04-02 S-P Reclamation, Inc. Resource recovery by catalytic conversion of polymers US5656757A (en) * 1995-08-10 1997-08-12 Alliedsignal Inc. Monomer recovery from multi-component materials US5869654A (en) * 1996-03-18 1999-02-09 Alliedsignal Inc. Process for depolymerizing polycaprolactam processing waste to form caprolactam US6087494A (en) * 1997-05-01 2000-07-11 Dsm N.V. Depolymerization of polyamides DE4421239A1 (en) * 1993-06-17 1994-12-22 Inventa Ag Process for the recycling of high-molecular-weight nylon 6, and repolymer prepared by this process US5455346B1 (en) * 1994-12-12 1999-02-09 Basf Corp Obtaining caprolactam by cleavage of molten polycaprolactam DE19718706A1 (en) 1997-05-02 1998-11-05 Basf Ag A process for preparing cyclic lactams Citations (6)
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* Cited by examiner, † Cited by third party Publication number Priority date Publication date Assignee Title DE851194C (en) * 1944-09-14 1952-10-02 Basf Ag A process for the production of monomer-caprolactam ªŠ JPS52108991A (en) * 1976-03-09 1977-09-12 Toyobo Co Ltd Purification of lactam EP0209021A2 (en) * 1985-07-09 1987-01-21 BASF Aktiengesellschaft Process for the recovery of caprolactam by decomposition of caprolactam oligomers Chem. Abstr. 84:18020a (1976).* Chem. Ing. Technik, Bd. 45, Nr. 24, pp. 1509 1524, (1973).* Chemical Abstracts, 71:49329, (1969).* Dmitrieva et al. 'Translated from Khimicheskie Volokna', vol. 17, No. 7 pp. 5-12 (1985). US5369215A (en) * 1992-04-06 1994-11-29 S-P Reclamation, Inc. Depolymerization method for resource recovery from polymeric wastes US5536831A (en) * 1994-12-12 1996-07-16 Basf Aktiengesellschaft Obtaining caprolactam by cleavage of molten polycaprolactam US5681952A (en) * 1995-12-08 1997-10-28 Alliedsignal Inc. Process for depolymerizing nylon-containing waste to form caprolactam US5929234A (en) * 1995-12-08 1999-07-27 Alliedsignal Inc. Process for depolymerizing nylon-containing whole carpet to form caprolactam US5948908A (en) * 1996-03-18 1999-09-07 Alliedsignal Inc. Process for depolymerizing polycaprolactam processing waste to form caprolactam US6087494A (en) * 1997-05-01 2000-07-11 Dsm N.V. Depolymerization of polyamides US6187917B1 (en) 1997-09-03 2001-02-13 Alliedsignal Inc. Process for the purification of caprolactam obtained from the depolymerization of polyamide-containing carpet US8080506B2 (en) 2009-07-14 2011-12-20 MSI Technology LLC. Reactive purge compound for polymer purging Also Published As
Publication number Publication date DE4211609A1 (en) 1993-03-04 US2241322A (en) Process for preparing polyamides from cyclic amides RU2144048C1 (en) Continuous polyamide production process, method of preparing high- molecular polycaproamide, and polycaproamide with molecular weight 3000-14000 KR100539338B1 (en) Process for Producing Polyamides from Aminonitriles EP0479306B1 (en) Preparation of polyamides from omega-aminonitriles US5053522A (en) Process for the preparation of lactide EP0552226B1 (en) Lactide production from dehydration of aqueous lactic acid feed CA1302000C (en) Removal of caprolactam and oligomers thereof from nylon granules containing same CA2128509A1 (en) Continuous process for manufacture of lactide polymers with improved purification methods US5043458A (en) One-step continuous process for preparing cyclic esters RU2153492C2 (en) Caprolactam production process JP4207574B2 (en) A process for producing laurolactam from cyclododecanone US5336754A (en) Preparation of amorphous/semicrystalline semi-aromatic (co)polyamides US5543494A (en) Process for the production of poly(lactic acid) Legal Events
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