CS215078B2 - Method of making the lactams - Google Patents
Method of making the lactams Download PDFInfo
- Publication number
- CS215078B2 CS215078B2 CS723130A CS313072A CS215078B2 CS 215078 B2 CS215078 B2 CS 215078B2 CS 723130 A CS723130 A CS 723130A CS 313072 A CS313072 A CS 313072A CS 215078 B2 CS215078 B2 CS 215078B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- solution
- sulfuric acid
- zone
- sulfur dioxide
- sulphate
- Prior art date
Links
- 150000003951 lactams Chemical class 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000000243 solution Substances 0.000 claims abstract description 54
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims abstract description 27
- 235000011130 ammonium sulphate Nutrition 0.000 claims abstract description 27
- 239000001166 ammonium sulphate Substances 0.000 claims abstract description 10
- 239000006227 byproduct Substances 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 48
- 238000003786 synthesis reaction Methods 0.000 claims description 19
- 230000015572 biosynthetic process Effects 0.000 claims description 18
- 238000000605 extraction Methods 0.000 claims description 17
- -1 oxyl Chemical group 0.000 claims description 6
- NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- CAMXVZOXBADHNJ-UHFFFAOYSA-N ammonium nitrite Chemical compound [NH4+].[O-]N=O CAMXVZOXBADHNJ-UHFFFAOYSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 238000000034 method Methods 0.000 description 30
- 229940032330 sulfuric acid Drugs 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000007789 gas Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 12
- 150000002923 oximes Chemical class 0.000 description 11
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 10
- 238000006146 oximation reaction Methods 0.000 description 9
- 230000008707 rearrangement Effects 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 7
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000795633 Olea <sea slug> Species 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000002485 combustion reaction Methods 0.000 description 6
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 5
- 101150047356 dec-1 gene Proteins 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000005979 thermal decomposition reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- COTCLZIUSPWWJJ-UHFFFAOYSA-M [Na+].[O-]S(=O)=S Chemical compound [Na+].[O-]S(=O)=S COTCLZIUSPWWJJ-UHFFFAOYSA-M 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003345 natural gas Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 102000007469 Actins Human genes 0.000 description 1
- 108010085238 Actins Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FNGLQNMQHOAIJQ-UHFFFAOYSA-N Cl[S](Cl)Cl Chemical compound Cl[S](Cl)Cl FNGLQNMQHOAIJQ-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- YCAWQMGAYOBYAN-UHFFFAOYSA-N NO.OS(O)(=O)=O.N Chemical compound NO.OS(O)(=O)=O.N YCAWQMGAYOBYAN-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FHHJDRFHHWUPDG-UHFFFAOYSA-N peroxysulfuric acid Chemical compound OOS(O)(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-N 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000013138 pruning Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/04—Preparation of lactams from or via oximes by Beckmann rearrangement
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7106341.A NL162375C (nl) | 1971-05-07 | 1971-05-07 | Verbeterde werkwijze voor de bereiding en winning van lactamen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS215078B2 true CS215078B2 (en) | 1982-07-30 |
Family
ID=19813109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS723130A CS215078B2 (en) | 1971-05-07 | 1972-05-10 | Method of making the lactams |
Country Status (8)
| Country | Link |
|---|---|
| BR (1) | BR7202828D0 (pl) |
| CS (1) | CS215078B2 (pl) |
| GB (1) | GB1342460A (pl) |
| HU (1) | HU170331B (pl) |
| NL (1) | NL162375C (pl) |
| PL (1) | PL81746B1 (pl) |
| TR (1) | TR17114A (pl) |
| ZA (1) | ZA722936B (pl) |
-
1971
- 1971-05-07 NL NL7106341.A patent/NL162375C/xx not_active IP Right Cessation
-
1972
- 1972-05-01 ZA ZA722936A patent/ZA722936B/xx unknown
- 1972-05-04 HU HUSA2352A patent/HU170331B/hu unknown
- 1972-05-05 TR TR17114A patent/TR17114A/xx unknown
- 1972-05-05 GB GB2113572A patent/GB1342460A/en not_active Expired
- 1972-05-05 BR BR2828/72A patent/BR7202828D0/pt unknown
- 1972-05-08 PL PL1972155238A patent/PL81746B1/pl unknown
- 1972-05-10 CS CS723130A patent/CS215078B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL162375B (nl) | 1979-12-17 |
| BR7202828D0 (pt) | 1973-05-17 |
| NL7106341A (pl) | 1972-11-09 |
| TR17114A (tr) | 1974-04-25 |
| ZA722936B (en) | 1973-02-28 |
| PL81746B1 (en) | 1975-08-30 |
| NL162375C (nl) | 1980-05-16 |
| HU170331B (pl) | 1977-05-28 |
| GB1342460A (en) | 1974-01-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ITMI20130847A1 (it) | Metodo e sistema per il recupero di solfato di ammonio da un flusso gassoso di un impianto urea | |
| EP0238575B1 (de) | Verfahren zur gewinnung von vanillin | |
| JPH02303591A (ja) | 排出液から硝酸塩及び／又は有機汚染物質の除去法 | |
| US3852273A (en) | Process for preparing and recovering lactams | |
| US4054562A (en) | Process for the manufacture of lactams | |
| US3852272A (en) | Process for removing lactams | |
| DE2110036C3 (de) | Verfahren zur Spaltung von Ammoniumsulfat | |
| JP2010163319A (ja) | 硫安の製造方法 | |
| SU814272A3 (ru) | Способ получени фосфорнойКиСлОТы | |
| US4140685A (en) | Process for recovering ε-caprolactam from an ε-caprolactam/sulfuric acid reaction mixture | |
| CA1066700A (en) | Process for preparing lactams | |
| US4081442A (en) | Process for the recovery of ε-caprolactam from a reaction mixture of ε-caprolactam and sulphuric acid | |
| DE1956905C3 (de) | Kreislaufverfahren zur Herstellung von Ketoximen | |
| US4133810A (en) | Process for the recovery of ε-caprolactam from a reaction mixture of ε-caprolactam and sulfuric acid | |
| US4153600A (en) | Process for the recovery of ε-caprolactam from a distillation residue containing ε-caprolactam | |
| US3879380A (en) | Process for recovery of lactam | |
| DE2508247A1 (de) | Verfahren zur herstellung von cyclohexanonoxim | |
| US2737511A (en) | Extraction of lactam | |
| US3133055A (en) | Production ofcaprolactam | |
| PL81746B1 (en) | Process for preparing and recovering lactams[gb1342460a] | |
| DE543555C (de) | Verfahren zur Darstellung von Thioharnstoff | |
| US3002996A (en) | Process for the preparation of dry oximes | |
| DE69902864T2 (de) | Methode zur Herstellung von Hydroxylaminsulfat in dem konventionellen Verfahren zur Synthese von Kaprolactam | |
| GB667075A (en) | An improved process for the manufacture of lactams | |
| DE2541824A1 (de) | Thermochemische verfahren zur erzeugung von wasserstoff aus wasser |