CS215078B2 - Method of making the lactams - Google Patents

Method of making the lactams Download PDF

Info

Publication number: CS215078B2
Authority: CS; Czechoslovakia
Prior art keywords: solution; sulfuric acid; zone; sulfur dioxide; sulphate
Prior art date: 1971-05-07

Application number

CS723130A

Other languages

Czech (cs)

English (en)

Inventor

Rooij Abraham H De

Original Assignee

Stamicarbon

Priority date (The priority date 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 date listed.)

1971-05-07

Filing date

1972-05-10

Publication date

1982-07-30

1972-05-10 Application filed by Stamicarbon filed Critical Stamicarbon

1982-07-30 Publication of CS215078B2 publication Critical patent/CS215078B2/cs

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)

CS723130A 1971-05-07 1972-05-10 Method of making the lactams CS215078B2 (en)

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 GB GB2113572A patent/GB1342460A/en not_active Expired
- 1972-05-05 BR BR2828/72A patent/BR7202828D0/pt unknown
- 1972-05-05 TR TR17114A patent/TR17114A/xx 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
BR7202828D0 (pt)	1973-05-17
GB1342460A (en)	1974-01-03
HU170331B (pl)	1977-05-28
NL7106341A (pl)	1972-11-09
NL162375C (nl)	1980-05-16
NL162375B (nl)	1979-12-17
PL81746B1 (en)	1975-08-30
TR17114A (tr)	1974-04-25
ZA722936B (en)	1973-02-28

Publication	Publication Date	Title
EP0238575B1 (de)	1989-08-02	Verfahren zur gewinnung von vanillin
US3852273A (en)	1974-12-03	Process for preparing and recovering lactams
US4054562A (en)	1977-10-18	Process for the manufacture of lactams
US3852272A (en)	1974-12-03	Process for removing lactams
DE2110036C3 (de)	1975-10-02	Verfahren zur Spaltung von Ammoniumsulfat
CS215078B2 (en)	1982-07-30	Method of making the lactams
JP2010163319A (ja)	2010-07-29	硫安の製造方法
US4140685A (en)	1979-02-20	Process for recovering ε-caprolactam from an ε-caprolactam/sulfuric acid reaction mixture
CA1066700A (en)	1979-11-20	Process for preparing lactams
US4081442A (en)	1978-03-28	Process for the recovery of ε-caprolactam from a reaction mixture of ε-caprolactam and sulphuric acid
DE1956905C3 (de)	1984-06-20	Kreislaufverfahren zur Herstellung von Ketoximen
US4133810A (en)	1979-01-09	Process for the recovery of ε-caprolactam from a reaction mixture of ε-caprolactam and sulfuric acid
US4153600A (en)	1979-05-08	Process for the recovery of ε-caprolactam from a distillation residue containing ε-caprolactam
US3879380A (en)	1975-04-22	Process for recovery of lactam
US4049646A (en)	1977-09-20	Process for the manufacture of lactams
US2737511A (en)	1956-03-06	Extraction of lactam
DE2046198A1 (de)	1971-04-01	Verbessertes Verfahren zur konti nuierhchen Herstellung einer Hydroxyl ammoniumsalzlösung in Wasser
US3133055A (en)	1964-05-12	Production ofcaprolactam
AU764204B2 (en)	2003-08-14	Method for removing nitrogen oxides from nitrosyl sulphuric acid
DE543555C (de)	1932-02-17	Verfahren zur Darstellung von Thioharnstoff
GB667075A (en)	1952-02-27	An improved process for the manufacture of lactams
DE2541824A1 (de)	1977-03-31	Thermochemische verfahren zur erzeugung von wasserstoff aus wasser
US3185732A (en)	1965-05-25	Method for producing oximes
CH532053A (de)	1972-12-31	Verfahren zur Herstellung von Lactamen
JPS62149665A (ja)	1987-07-03	ラクタムの製造法