DE2332973A1 - Verfahren zur gewinnung von lactamen aus sauren reaktionsgemischen - Google Patents
Verfahren zur gewinnung von lactamen aus sauren reaktionsgemischenInfo
- Publication number
- DE2332973A1 DE2332973A1 DE2332973A DE2332973A DE2332973A1 DE 2332973 A1 DE2332973 A1 DE 2332973A1 DE 2332973 A DE2332973 A DE 2332973A DE 2332973 A DE2332973 A DE 2332973A DE 2332973 A1 DE2332973 A1 DE 2332973A1
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- amylphenol
- substituted
- sulfuric acid
- lactam
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 23
- 239000011541 reaction mixture Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000002253 acid Substances 0.000 title description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 34
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 34
- 150000003951 lactams Chemical class 0.000 claims description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000002989 phenols Chemical class 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 239000003929 acidic solution Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 108010032039 (rat secretin-27)-Gly-rhodamine Proteins 0.000 claims 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- -1 di-substituted phenols Chemical class 0.000 claims 1
- 238000011084 recovery Methods 0.000 description 10
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- ROMXEVFSCNLHAB-UHFFFAOYSA-N 2-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC=CC=C1O ROMXEVFSCNLHAB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001896 cresols Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- GJYCVCVHRSWLNY-UHFFFAOYSA-N ortho-butylphenol Natural products CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/16—Separation or purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Extraction Or Liquid Replacement (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicines Containing Plant Substances (AREA)
- Separation By Low-Temperature Treatments (AREA)
- Pyrrole Compounds (AREA)
- Polyamides (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT26384/72A IT956940B (it) | 1972-06-28 | 1972-06-28 | Procedimento per l estrazione di lattami da miscele acide di rea zione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2332973A1 true DE2332973A1 (de) | 1974-01-10 |
Family
ID=11219370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2332973A Ceased DE2332973A1 (de) | 1972-06-28 | 1973-06-28 | Verfahren zur gewinnung von lactamen aus sauren reaktionsgemischen |
Country Status (23)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0363894A3 (de) * | 1988-10-13 | 1991-10-09 | Hoechst Aktiengesellschaft | Verfahren zur Extraktion von N-Methyl-Pyrrolidon-(2) |
| NL1000781C2 (nl) * | 1995-07-12 | 1997-01-14 | Dsm Nv | Werkwijze voor het winnen van caprolactam uit nylon-6 bevattende afval. |
| WO1997030028A3 (en) * | 1996-02-17 | 1997-09-25 | Dsm Nv | Recovery of epsilon-caprolactam from aqueous mixtures |
| EP0826665A1 (en) * | 1996-09-02 | 1998-03-04 | Dsm N.V. | Recovery of epsilon-caprolactam from aqueous mixtures |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4013640A (en) * | 1974-04-11 | 1977-03-22 | Union Carbide Corporation | Process for the recovery of amides |
| DE2926279A1 (de) * | 1979-06-29 | 1981-01-08 | Basf Ag | Verfahren zur reinigung von caprolactam |
| US4328154A (en) * | 1980-11-03 | 1982-05-04 | Snia Viscosa Societa' Nazionale Industria Applicazioni Viscosa S.P.A. | Process for the purification of raw caprolactam |
| BE1011047A3 (nl) * | 1997-03-17 | 1999-04-06 | Dsm Nv | Werkwijze voor het zuiveren van caprolactam. |
| TW201114740A (en) * | 2009-10-30 | 2011-05-01 | China Petrochemical Dev Corp Taipei Taiwan | Method of separating amide from amino acid ionic solution |
| CN102335573B (zh) * | 2010-07-23 | 2013-09-11 | 中国石油化工股份有限公司 | 一种己内酰胺苛化装置 |
| TWI414508B (zh) | 2011-01-17 | 2013-11-11 | China Petrochemical Dev Corp Taipei Taiwan | A catalyst composition and a method for preparing an amide using the composition |
| BR112016007654A2 (pt) * | 2013-10-07 | 2017-11-14 | Gfbiochemicals Ltd | processo para preparar ácido levulínico |
| CN104387322A (zh) * | 2014-10-21 | 2015-03-04 | 湖南百利工程科技股份有限公司 | 一种低副产硫酸铵的己内酰胺的制备方法 |
| CN104262252A (zh) * | 2014-10-21 | 2015-01-07 | 湖南百利工程科技股份有限公司 | 一种从己内酰胺硫酸酯中分离己内酰胺和硫酸的方法 |
| CN104910071A (zh) * | 2015-05-08 | 2015-09-16 | 河北美邦工程科技股份有限公司 | 一种制备己内酰胺的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH78A (de) * | 1889-01-18 | August Graemiger Anton | Apparat zum Färben, Waschen, Bleichen u. s. w., von Garn in aufgewickeltem Zustande | |
| CH446342A (de) * | 1963-11-29 | 1967-11-15 | Bayer Ag | Verfahren zum Herstellen reiner Lactame |
-
1972
- 1972-06-28 IT IT26384/72A patent/IT956940B/it active
-
1973
- 1973-06-25 NO NO2630/73A patent/NO143220C/no unknown
- 1973-06-26 ZA ZA734342A patent/ZA734342B/xx unknown
- 1973-06-26 US US373799A patent/US3912721A/en not_active Expired - Lifetime
- 1973-06-27 DK DK356573*A patent/DK133150C/da active
- 1973-06-27 CH CH940773A patent/CH602632A5/xx not_active IP Right Cessation
- 1973-06-27 SU SU1937628A patent/SU557754A3/ru active
- 1973-06-27 IE IE1074/73A patent/IE37857B1/xx unknown
- 1973-06-27 GB GB3045773A patent/GB1430006A/en not_active Expired
- 1973-06-28 TR TR17560A patent/TR17560A/xx unknown
- 1973-06-28 JP JP7235473A patent/JPS5544067B2/ja not_active Expired
- 1973-06-28 ES ES416415A patent/ES416415A1/es not_active Expired
- 1973-06-28 IN IN1513/CAL/1973A patent/IN139738B/en unknown
- 1973-06-28 AR AR248801A patent/AR197617A1/es active
- 1973-06-28 FR FR7323688A patent/FR2190821B1/fr not_active Expired
- 1973-06-28 NL NL7309031A patent/NL7309031A/xx not_active Application Discontinuation
- 1973-06-28 CA CA175,181A patent/CA1018524A/en not_active Expired
- 1973-06-28 BR BR4800/73A patent/BR7304800D0/pt unknown
- 1973-06-28 BE BE132858A patent/BE801610A/xx unknown
- 1973-06-28 AT AT569973A patent/AT326676B/de active
- 1973-06-28 AU AU57449/73A patent/AU475133B2/en not_active Expired
- 1973-06-28 DE DE2332973A patent/DE2332973A1/de not_active Ceased
- 1973-07-06 IL IL42677A patent/IL42677A/en unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0363894A3 (de) * | 1988-10-13 | 1991-10-09 | Hoechst Aktiengesellschaft | Verfahren zur Extraktion von N-Methyl-Pyrrolidon-(2) |
| NL1000781C2 (nl) * | 1995-07-12 | 1997-01-14 | Dsm Nv | Werkwijze voor het winnen van caprolactam uit nylon-6 bevattende afval. |
| WO1997003048A1 (en) * | 1995-07-12 | 1997-01-30 | Dsm N.V. | Process for the recovery of caprolactam from waste containing nylon by extraction with alkyl phenols |
| US6111099A (en) * | 1995-07-12 | 2000-08-29 | Dsm N.V. | Process for the recovery of caprolactam from waste containing nylon |
| WO1997030028A3 (en) * | 1996-02-17 | 1997-09-25 | Dsm Nv | Recovery of epsilon-caprolactam from aqueous mixtures |
| US6191274B1 (en) | 1996-02-17 | 2001-02-20 | Dsm N.V. | Recovery of ε-caprolactam |
| EP0826665A1 (en) * | 1996-09-02 | 1998-03-04 | Dsm N.V. | Recovery of epsilon-caprolactam from aqueous mixtures |
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |