FI115906B - Menetelmä syklisten laktaamien valmistamiseksi - Google Patents

Menetelmä syklisten laktaamien valmistamiseksi Download PDF

Info

Publication number: FI115906B
Authority: FI; Finland
Prior art keywords: reaction; aminocaproic acid; water; alkyl; caprolactam
Prior art date: 1994-06-28

Application number

FI965229A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI965229L (fi

FI965229A0 (fi

Inventor

Eberhard Fuchs

Tom Witzel

Original Assignee

Basf Ag

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.)

1994-06-28

Filing date

1996-12-27

Publication date

2005-08-15

1996-12-27 Application filed by Basf Ag filed Critical Basf Ag

1996-12-27 Publication of FI965229A0 publication Critical patent/FI965229A0/fi

1997-02-27 Publication of FI965229L publication Critical patent/FI965229L/fi

2005-08-15 Application granted granted Critical

2005-08-15 Publication of FI115906B publication Critical patent/FI115906B/fi

Links

238000000034 method Methods 0.000 title claims abstract description 19
-1 cyclic lactams Chemical class 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title description 6
238000006243 chemical reaction Methods 0.000 claims abstract description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
239000001257 hydrogen Substances 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
239000002638 heterogeneous catalyst Substances 0.000 claims abstract description 5
239000007791 liquid phase Substances 0.000 claims abstract description 5
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 6
101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
ZLHYDRXTDZFRDZ-UHFFFAOYSA-N epsilon-aminocaproamide Chemical compound NCCCCCC(N)=O ZLHYDRXTDZFRDZ-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
OOYRLFIIUVBZSY-UHFFFAOYSA-N n,n-diethyldecanamide Chemical compound CCCCCCCCCC(=O)N(CC)CC OOYRLFIIUVBZSY-UHFFFAOYSA-N 0.000 claims 1
238000000746 purification Methods 0.000 claims 1
125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 38
SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
229960002684 aminocaproic acid Drugs 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 8
230000035484 reaction time Effects 0.000 description 6
239000000243 solution Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
150000003951 lactams Chemical class 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
NJNQDCIAOXIFTB-UHFFFAOYSA-N ethyl 6-aminohexanoate Chemical compound CCOC(=O)CCCCCN NJNQDCIAOXIFTB-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
230000000737 periodic effect Effects 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
PLDDOISOJJCEMH-UHFFFAOYSA-N neodymium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Nd+3].[Nd+3] PLDDOISOJJCEMH-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000004408 titanium dioxide Substances 0.000 description 2
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
JYYXVDYYEXMEJU-UHFFFAOYSA-N 6-amino-n,n-dimethylhexanamide Chemical compound CN(C)C(=O)CCCCCN JYYXVDYYEXMEJU-UHFFFAOYSA-N 0.000 description 1
GXQFDPRUJPBDFB-UHFFFAOYSA-N 6-amino-n-ethylhexanamide Chemical compound CCNC(=O)CCCCCN GXQFDPRUJPBDFB-UHFFFAOYSA-N 0.000 description 1
BUSHYIBZUMHUEU-UHFFFAOYSA-N 6-amino-n-methylhexanamide Chemical compound CNC(=O)CCCCCN BUSHYIBZUMHUEU-UHFFFAOYSA-N 0.000 description 1
241001214176 Capros Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
YTIHIRCOUAPRCS-UHFFFAOYSA-N Dl-norleucinamide Chemical compound CCCCC(N)C(N)=O YTIHIRCOUAPRCS-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052768 actinide Inorganic materials 0.000 description 1
150000001255 actinides Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
239000000956 alloy Substances 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052810 boron oxide Inorganic materials 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
229910000420 cerium oxide Inorganic materials 0.000 description 1
229910000423 chromium oxide Inorganic materials 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
235000004879 dioscorea Nutrition 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
TZJVWRXHKAXSEA-UHFFFAOYSA-N methyl 6-aminohexanoate Chemical compound COC(=O)CCCCCN TZJVWRXHKAXSEA-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
229910000476 molybdenum oxide Inorganic materials 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910000484 niobium oxide Inorganic materials 0.000 description 1
URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
229940078552 o-xylene Drugs 0.000 description 1
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
MMKQUGHLEMYQSG-UHFFFAOYSA-N oxygen(2-);praseodymium(3+) Chemical compound [O-2].[O-2].[O-2].[Pr+3].[Pr+3] MMKQUGHLEMYQSG-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229910003447 praseodymium oxide Inorganic materials 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
229910003452 thorium oxide Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- C07D201/08—Preparation of lactams from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyrrole Compounds (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyamides (AREA)
Catalysts (AREA)
Cephalosporin Compounds (AREA)

FI965229A 1994-06-28 1996-12-27 Menetelmä syklisten laktaamien valmistamiseksi FI115906B (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE4422610		1994-06-28
DE4422610A DE4422610A1 (de)	1994-06-28	1994-06-28	Verfahren zur Herstellung von cyclischen Lactamen
PCT/EP1995/002338 WO1996000722A1 (de)	1994-06-28	1995-06-16	Verfahren zur herstellung von cyclischen lactamen
EP9502338		1995-06-16

Publications (3)

Publication Number	Publication Date
FI965229A0 FI965229A0 (fi)	1996-12-27
FI965229L FI965229L (fi)	1997-02-27
FI115906B true FI115906B (fi)	2005-08-15

Family

ID=6521721

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI965229A FI115906B (fi)	1994-06-28	1996-12-27	Menetelmä syklisten laktaamien valmistamiseksi

Country Status (20)

Country	Link
US (1)	US5502185A (pt)
EP (1)	EP0769004B1 (pt)
JP (1)	JPH10502064A (pt)
KR (1)	KR100379798B1 (pt)
CN (1)	CN1068310C (pt)
AT (1)	ATE236875T1 (pt)
AU (1)	AU694532B2 (pt)
BG (1)	BG62288B1 (pt)
BR (1)	BR9508147A (pt)
DE (2)	DE4422610A1 (pt)
ES (1)	ES2196065T3 (pt)
FI (1)	FI115906B (pt)
HU (1)	HU220970B1 (pt)
MY (1)	MY112291A (pt)
NO (1)	NO314259B1 (pt)
NZ (1)	NZ289098A (pt)
PL (1)	PL185462B1 (pt)
RU (1)	RU2167861C2 (pt)
UA (1)	UA45346C2 (pt)
WO (1)	WO1996000722A1 (pt)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MY113899A (en) *	1995-03-01	2002-06-29	Dsm Ip Assets Bv	Process for the preparation of (permittivy)-caprolactam and (permittivy)-caprolactam precursors
US5780623A (en) *	1996-02-23	1998-07-14	Dsm N.V.	Process to prepare ε-caprolactam from 6-aminocaproic acid
US5652362A (en) *	1996-05-06	1997-07-29	Industrial Technology Research Institute	Preparation of caprolactam
EP0882710A1 (en) *	1997-06-03	1998-12-09	Industrial Technology Research Institute	Method for the preparation of caprolactam and preparation of catalysts for this method
KR20010023544A (ko) *	1997-09-03	2001-03-26	스타르크, 카르크	촉매로 사용될 수 있는 성형 재료

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2956051A (en) *		1960-10-11		Process for preparing cyclic amides
US2301964A (en) *	1941-09-12	1942-11-17	Du Pont	Method of preparing lactams
US2357484A (en) *	1941-09-12	1944-09-05	Du Pont	Process for producing compounds containing an n-substituted amide group
FR1184282A (fr) *	1956-10-12	1959-07-20	Ici Ltd	Fabrication d'amides cycliques
US3485821A (en) *	1967-05-29	1969-12-23	Techni Chem Co The	Process for preparing caprolactam and its alkyl substituted derivatives
GB1268869A (en) *	1968-09-04	1972-03-29	Teijin Ltd	PROCESS FOR THE PREPARATION OF epsilon-CAPROLACTAM
US3888845A (en) *	1970-03-09	1975-06-10	Teijin Ltd	Process for producing epsilon-caprolactam
US3988319A (en) *	1974-09-16	1976-10-26	Allied Chemical Corporation	Process for producing caprolactam from 6-aminocaproic acid
DE3403574A1 (de) *	1984-02-02	1985-08-08	Basf Ag, 6700 Ludwigshafen	Verfahren zur gewinnung von caprolactam aus (epsilon)-aminocapronsaeure
US4628085A (en) *	1985-09-03	1986-12-09	Allied Corporation	Use of silica catalyst for selective production of lactams
DE3643010A1 (de) *	1986-12-17	1988-06-30	Basf Ag	Verfahren zur herstellung von caprolactam
DE3843793A1 (de) *	1988-12-24	1990-07-05	Basf Ag	Verfahren zur herstellung von caprolactam

1994
- 1994-06-28 DE DE4422610A patent/DE4422610A1/de not_active Withdrawn
- 1994-12-19 US US08/358,413 patent/US5502185A/en not_active Expired - Fee Related
1995
- 1995-06-16 AU AU28839/95A patent/AU694532B2/en not_active Ceased
- 1995-06-16 EP EP95924256A patent/EP0769004B1/de not_active Expired - Lifetime
- 1995-06-16 KR KR1019960707527A patent/KR100379798B1/ko not_active Expired - Fee Related
- 1995-06-16 CN CN95194326A patent/CN1068310C/zh not_active Expired - Fee Related
- 1995-06-16 RU RU97101178/04A patent/RU2167861C2/ru not_active IP Right Cessation
- 1995-06-16 JP JP8502763A patent/JPH10502064A/ja not_active Ceased
- 1995-06-16 PL PL95318113A patent/PL185462B1/pl not_active IP Right Cessation
- 1995-06-16 BR BR9508147A patent/BR9508147A/pt not_active IP Right Cessation
- 1995-06-16 AT AT95924256T patent/ATE236875T1/de not_active IP Right Cessation
- 1995-06-16 DE DE59510633T patent/DE59510633D1/de not_active Expired - Fee Related
- 1995-06-16 ES ES95924256T patent/ES2196065T3/es not_active Expired - Lifetime
- 1995-06-16 NZ NZ289098A patent/NZ289098A/xx unknown
- 1995-06-16 WO PCT/EP1995/002338 patent/WO1996000722A1/de not_active Ceased
- 1995-06-16 UA UA97010350A patent/UA45346C2/uk unknown
- 1995-06-16 HU HU9603620A patent/HU220970B1/hu not_active IP Right Cessation
- 1995-06-28 MY MYPI95001775A patent/MY112291A/en unknown
1996
- 1996-12-27 NO NO19965611A patent/NO314259B1/no unknown
- 1996-12-27 FI FI965229A patent/FI115906B/fi not_active IP Right Cessation
1997
- 1997-01-06 BG BG101111A patent/BG62288B1/bg unknown

Also Published As

Publication number	Publication date
FI965229L (fi)	1997-02-27
EP0769004B1 (de)	2003-04-09
AU694532B2 (en)	1998-07-23
DE59510633D1 (de)	2003-05-15
AU2883995A (en)	1996-01-25
BR9508147A (pt)	1997-11-04
US5502185A (en)	1996-03-26
ATE236875T1 (de)	2003-04-15
RU2167861C2 (ru)	2001-05-27
DE4422610A1 (de)	1996-01-04
WO1996000722A1 (de)	1996-01-11
HU220970B1 (hu)	2002-07-29
FI965229A0 (fi)	1996-12-27
MY112291A (en)	2001-05-31
BG101111A (en)	1997-08-29
ES2196065T3 (es)	2003-12-16
KR100379798B1 (ko)	2003-08-21
NO965611D0 (no)	1996-12-27
JPH10502064A (ja)	1998-02-24
NO965611L (no)	1997-02-24
PL185462B1 (pl)	2003-05-30
BG62288B1 (bg)	1999-07-30
NO314259B1 (no)	2003-02-24
EP0769004A1 (de)	1997-04-23
CN1068310C (zh)	2001-07-11
UA45346C2 (uk)	2002-04-15
PL318113A1 (en)	1997-05-12
NZ289098A (en)	1999-01-28
CN1154104A (zh)	1997-07-09
HUT77180A (hu)	1998-03-02
HU9603620D0 (en)	1997-02-28

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