DE3235938A1 - Verfahren zur herstellung von cyanovaleriansaeureestern und caprolactam - Google Patents
Verfahren zur herstellung von cyanovaleriansaeureestern und caprolactamInfo
- Publication number
- DE3235938A1 DE3235938A1 DE19823235938 DE3235938A DE3235938A1 DE 3235938 A1 DE3235938 A1 DE 3235938A1 DE 19823235938 DE19823235938 DE 19823235938 DE 3235938 A DE3235938 A DE 3235938A DE 3235938 A1 DE3235938 A1 DE 3235938A1
- Authority
- DE
- Germany
- Prior art keywords
- caprolactam
- reaction
- alcohol
- adipic acid
- acid ester
- 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.)
- Granted
Links
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims description 213
- 238000000034 method Methods 0.000 title claims description 56
- NICLKHGIKDZZGV-UHFFFAOYSA-N 2-cyanopentanoic acid Chemical class CCCC(C#N)C(O)=O NICLKHGIKDZZGV-UHFFFAOYSA-N 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 26
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 110
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 90
- 238000006243 chemical reaction Methods 0.000 claims description 90
- 238000004821 distillation Methods 0.000 claims description 57
- 239000001361 adipic acid Substances 0.000 claims description 55
- 235000011037 adipic acid Nutrition 0.000 claims description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
- -1 cyanovaleric acid ester Chemical class 0.000 claims description 49
- 239000011541 reaction mixture Substances 0.000 claims description 46
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 42
- 229960002684 aminocaproic acid Drugs 0.000 claims description 33
- 239000007788 liquid Substances 0.000 claims description 31
- 230000008569 process Effects 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- 150000005846 sugar alcohols Polymers 0.000 claims description 18
- 238000009835 boiling Methods 0.000 claims description 16
- 230000032050 esterification Effects 0.000 claims description 15
- 238000005886 esterification reaction Methods 0.000 claims description 15
- FPDYKABXINADKS-UHFFFAOYSA-N 2-(methylazaniumyl)hexanoate Chemical compound CCCCC(NC)C(O)=O FPDYKABXINADKS-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- IIVUKYTTXBEJRB-UHFFFAOYSA-N 2-(ethylamino)hexanoic acid Chemical compound CCCCC(C(O)=O)NCC IIVUKYTTXBEJRB-UHFFFAOYSA-N 0.000 claims description 4
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- WNZKWBYFYOMJRC-UHFFFAOYSA-N methyl 2-cyanopentanoate Chemical compound CCCC(C#N)C(=O)OC WNZKWBYFYOMJRC-UHFFFAOYSA-N 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 239000006227 byproduct Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 13
- 239000010941 cobalt Substances 0.000 description 12
- 229910017052 cobalt Inorganic materials 0.000 description 12
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000006722 reduction reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- MLVRCZPSHCVRHN-UHFFFAOYSA-N ethyl 2-cyanopentanoate Chemical compound CCCC(C#N)C(=O)OCC MLVRCZPSHCVRHN-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000009467 reduction Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 5
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 5
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 5
- 235000011130 ammonium sulphate Nutrition 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000011010 flushing procedure Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- YAXKTBLXMTYWDQ-UHFFFAOYSA-N 1,2,3-butanetriol Chemical compound CC(O)C(O)CO YAXKTBLXMTYWDQ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ODICIKUFABDORO-UHFFFAOYSA-N 2-cyano-2-methylpentanoic acid Chemical compound CCCC(C)(C#N)C(O)=O ODICIKUFABDORO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical compound CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 229940070710 valerate Drugs 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- BOWUOGIPSRVRSJ-UHFFFAOYSA-N 2-aminohexano-6-lactam Chemical compound NC1CCCCNC1=O BOWUOGIPSRVRSJ-UHFFFAOYSA-N 0.000 description 1
- CIQRWLRUNXKNTE-UHFFFAOYSA-N 2-cyanononanoic acid Chemical compound CCCCCCCC(C#N)C(O)=O CIQRWLRUNXKNTE-UHFFFAOYSA-N 0.000 description 1
- SZNILIWUUKKNPE-UHFFFAOYSA-N 2-nitrocyclohexan-1-one Chemical compound [O-][N+](=O)C1CCCCC1=O SZNILIWUUKKNPE-UHFFFAOYSA-N 0.000 description 1
- HTZWBJTVKWGSHY-UHFFFAOYSA-N C=C=O.CC(=O)OC(C)=O Chemical compound C=C=O.CC(=O)OC(C)=O HTZWBJTVKWGSHY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- IWWCATWBROCMCW-UHFFFAOYSA-N batyl alcohol Natural products CCCCCCCCCCCCCCCCCCOC(O)CO IWWCATWBROCMCW-UHFFFAOYSA-N 0.000 description 1
- BXDNFAXUAQVKRQ-UHFFFAOYSA-L cobalt(2+);pentanoate Chemical compound [Co+2].CCCCC([O-])=O.CCCCC([O-])=O BXDNFAXUAQVKRQ-UHFFFAOYSA-L 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- DRJNNZMCOCQJGI-UHFFFAOYSA-N cyclohexen-1-yl acetate Chemical compound CC(=O)OC1=CCCCC1 DRJNNZMCOCQJGI-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- LBSCRRFAOKTHPV-UHFFFAOYSA-N dimethyl hexanedioate;hexanedioic acid Chemical compound OC(=O)CCCCC(O)=O.COC(=O)CCCCC(=O)OC LBSCRRFAOKTHPV-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 1
- JJAIIULJXXEFLV-UHFFFAOYSA-N pentane-2,3,4-triol Chemical compound CC(O)C(O)C(C)O JJAIIULJXXEFLV-UHFFFAOYSA-N 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method 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
- 238000007086 side reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16456781A JPS5867666A (ja) | 1981-10-15 | 1981-10-15 | カプロラクタムの製造方法 |
| JP56194376A JPS6021980B2 (ja) | 1981-12-04 | 1981-12-04 | カプロラクタムの製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3235938A1 true DE3235938A1 (de) | 1983-04-21 |
| DE3235938C2 DE3235938C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-05-11 |
Family
ID=26489612
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823235938 Granted DE3235938A1 (de) | 1981-10-15 | 1982-09-29 | Verfahren zur herstellung von cyanovaleriansaeureestern und caprolactam |
| DE3249485A Expired DE3249485C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-10-15 | 1982-09-29 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3249485A Expired DE3249485C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-10-15 | 1982-09-29 |
Country Status (7)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0271817A1 (de) * | 1986-12-17 | 1988-06-22 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Caprolactam aus 6-Aminocapronsäure, deren Estern und Amiden |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3643010A1 (de) * | 1986-12-17 | 1988-06-30 | Basf Ag | Verfahren zur herstellung von caprolactam |
| FR2781480B1 (fr) * | 1998-07-22 | 2001-06-01 | Rhone Poulenc Fibres | Procede d'hydrolyse cyclisante d'un compose aminonitrile en lactame |
| DE10028950A1 (de) | 2000-06-16 | 2001-12-20 | Basf Ag | Verfahren zur Herstellung von Caprolactam |
| US6372939B1 (en) * | 2000-11-16 | 2002-04-16 | E.I. Du Pont De Nemours And Company | Production of 6-aminocaproic acid |
| US6365770B1 (en) * | 2000-11-16 | 2002-04-02 | E. I. Du Pont De Nemours And Company | Production of alkyl 6-aminocaproate |
| JP2002193927A (ja) * | 2000-12-21 | 2002-07-10 | National Institute Of Advanced Industrial & Technology | ラクタムの合成方法 |
| FR2882360B1 (fr) * | 2005-02-22 | 2008-12-26 | Rhodia Chimie Sa | Procede de fabrication de lactames |
| AU2009244815B2 (en) * | 2008-05-09 | 2015-04-30 | Rhodia Operations | Cleaning compositions incorporating green solvents and methods for use |
| US8222194B2 (en) * | 2008-05-09 | 2012-07-17 | Rhodia Operations | Cleaning compositions incorporating green solvents and methods for use |
| BR112012009201A2 (pt) * | 2009-10-19 | 2016-08-16 | Rhodia Operations | sistemas de limpeza autoemulsionantes e métodos de uso |
| JP2013544947A (ja) | 2010-12-10 | 2013-12-19 | ローディア オペレーションズ | タールサンド／ビチューメン／アスファルテン洗浄適用においてテルペン共溶媒、代替物および／または担体として使用される二塩基酸エステル |
| CA2873685C (en) | 2012-04-17 | 2020-06-02 | Rhodia Operations | Polysaccharide slurries with environmentally friendly activator solvents |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3485821A (en) | 1967-05-29 | 1969-12-23 | Techni Chem Co The | Process for preparing caprolactam and its alkyl substituted derivatives |
| US3919197A (en) | 1972-12-08 | 1975-11-11 | Stamicarbon | Preparation of beta-alkoxy-omega-lactams |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2377795A (en) * | 1945-06-05 | Synthesis of adiponitrile | ||
| US2322273A (en) * | 1940-11-22 | 1943-06-22 | Bell Telephone Labor Inc | Process for manufacture of esters of mononitriles of dicarboxylic acids |
| DE1035139B (de) * | 1953-11-05 | 1958-07-31 | Huels Chemische Werke Ag | Verfahren zur Herstellung von ªŠ-Caprolactam |
| US2970997A (en) * | 1957-02-01 | 1961-02-07 | Hoechst Ag | Process for the manufacture of epsilon-caprolactam |
| US3050547A (en) * | 1959-07-02 | 1962-08-21 | Dow Chemical Co | 1-2 ring cleavage of 2-cyanocyclo-alkanones |
| CH456562A (de) * | 1963-11-22 | 1968-07-31 | Inventa Ag | Verfahren zur Herstellung von w-Cyancarbonsäuren |
| US3341567A (en) * | 1964-02-14 | 1967-09-12 | Kurashiki Rayon Co | Process for the production of benzenedicarboxylic acid and aliphatic dinitrile by exchanging carboxylic group for cyano group |
| IT1043824B (it) * | 1969-09-12 | 1980-02-29 | Daiichi Seiyaku Co | Procedimento per preparare acido 4 ciano cicloesancareossi lico |
| NL7216661A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-12-08 | 1974-06-11 | ||
| JPS5047927A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-08-31 | 1975-04-28 | ||
| US3988319A (en) * | 1974-09-16 | 1976-10-26 | Allied Chemical Corporation | Process for producing caprolactam from 6-aminocaproic acid |
-
1982
- 1982-09-21 US US06/420,883 patent/US4470928A/en not_active Expired - Lifetime
- 1982-09-27 CA CA000412277A patent/CA1181398A/en not_active Expired
- 1982-09-28 AU AU88772/82A patent/AU536959B2/en not_active Ceased
- 1982-09-29 DE DE19823235938 patent/DE3235938A1/de active Granted
- 1982-09-29 GB GB08227770A patent/GB2108119B/en not_active Expired
- 1982-09-29 FR FR8216407A patent/FR2514763B1/fr not_active Expired
- 1982-09-29 DE DE3249485A patent/DE3249485C2/de not_active Expired
- 1982-10-13 SU SU3501768A patent/SU1279527A3/ru active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3485821A (en) | 1967-05-29 | 1969-12-23 | Techni Chem Co The | Process for preparing caprolactam and its alkyl substituted derivatives |
| US3919197A (en) | 1972-12-08 | 1975-11-11 | Stamicarbon | Preparation of beta-alkoxy-omega-lactams |
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0271817A1 (de) * | 1986-12-17 | 1988-06-22 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Caprolactam aus 6-Aminocapronsäure, deren Estern und Amiden |
| US4767856A (en) * | 1986-12-17 | 1988-08-30 | Basf Aktiengesellschaft | Preparation of caprolactam from 6-aminocaproic acid, esters and amides |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2514763B1 (fr) | 1987-06-05 |
| AU536959B2 (en) | 1984-05-31 |
| DE3249485C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-09-15 |
| US4470928A (en) | 1984-09-11 |
| CA1181398A (en) | 1985-01-22 |
| AU8877282A (en) | 1983-05-19 |
| GB2108119B (en) | 1986-01-02 |
| DE3235938C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-05-11 |
| FR2514763A1 (fr) | 1983-04-22 |
| GB2108119A (en) | 1983-05-11 |
| SU1279527A1 (ru) | 1986-12-23 |
| SU1279527A3 (ru) | 1986-12-23 |
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