DE2240317C3 - Verfahren zur Wiedergewinnung erneut einsetzbarer palladiumhaltiger Katalysatoren aus flüssigen Reaktionsgemischen, die bei der Herstellung von Essigsäurearylestern anfallen - Google Patents
Verfahren zur Wiedergewinnung erneut einsetzbarer palladiumhaltiger Katalysatoren aus flüssigen Reaktionsgemischen, die bei der Herstellung von Essigsäurearylestern anfallenInfo
- Publication number
- DE2240317C3 DE2240317C3 DE2240317A DE2240317A DE2240317C3 DE 2240317 C3 DE2240317 C3 DE 2240317C3 DE 2240317 A DE2240317 A DE 2240317A DE 2240317 A DE2240317 A DE 2240317A DE 2240317 C3 DE2240317 C3 DE 2240317C3
- Authority
- DE
- Germany
- Prior art keywords
- acetic acid
- mixture
- catalyst
- palladium
- distillation
- 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.)
- Expired
Links
- 239000003054 catalyst Substances 0.000 title claims description 37
- 239000007788 liquid Substances 0.000 title claims description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims description 18
- 239000011541 reaction mixture Substances 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 13
- 229910052763 palladium Inorganic materials 0.000 title claims description 9
- -1 aryl acetic acid esters Chemical class 0.000 title claims description 7
- 238000011084 recovery Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 108
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 22
- 229910017604 nitric acid Inorganic materials 0.000 claims description 21
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 17
- 238000000605 extraction Methods 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 150000007860 aryl ester derivatives Chemical class 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 4
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 231100000357 carcinogen Toxicity 0.000 claims 1
- 239000003183 carcinogenic agent Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000003610 charcoal Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 150000002828 nitro derivatives Chemical class 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical group [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 10
- 239000012295 chemical reaction liquid Substances 0.000 description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- CDJJKTLOZJAGIZ-UHFFFAOYSA-N Tolylacetate Chemical compound CC(=O)OC1=CC=C(C)C=C1 CDJJKTLOZJAGIZ-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
- 229940071125 manganese acetate Drugs 0.000 description 4
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 4
- 229940049953 phenylacetate Drugs 0.000 description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- FSALNWWFUMHOAU-UHFFFAOYSA-N (4-tert-butylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C(C)(C)C)C=C1 FSALNWWFUMHOAU-UHFFFAOYSA-N 0.000 description 2
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 2
- QZYHIOPPLUPUJF-UHFFFAOYSA-N 3-nitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1 QZYHIOPPLUPUJF-UHFFFAOYSA-N 0.000 description 2
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- OTGAHJPFNKQGAE-UHFFFAOYSA-N cresatin Chemical compound CC(=O)OC1=CC=CC(C)=C1 OTGAHJPFNKQGAE-UHFFFAOYSA-N 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- AMZORBZSQRUXNC-UHFFFAOYSA-N o-Tolyl acetate Chemical compound CC(=O)OC1=CC=CC=C1C AMZORBZSQRUXNC-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- QWAPRPBICJAUPX-UHFFFAOYSA-N (3-tert-butylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C(C)(C)C)=C1 QWAPRPBICJAUPX-UHFFFAOYSA-N 0.000 description 1
- IWTHGPTVKBEURV-UHFFFAOYSA-N 1-tert-butyl-2-nitrobenzene Chemical compound CC(C)(C)C1=CC=CC=C1[N+]([O-])=O IWTHGPTVKBEURV-UHFFFAOYSA-N 0.000 description 1
- NZTWPACKXIQEFV-UHFFFAOYSA-N 2-phenylacetic acid;hydrate Chemical compound O.OC(=O)CC1=CC=CC=C1 NZTWPACKXIQEFV-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride 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
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6385971A JPS5025462B2 (enExample) | 1971-08-21 | 1971-08-21 | |
| JP46068059A JPS5215B2 (enExample) | 1971-09-06 | 1971-09-06 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2240317A1 DE2240317A1 (de) | 1973-03-01 |
| DE2240317B2 DE2240317B2 (enExample) | 1974-11-21 |
| DE2240317C3 true DE2240317C3 (de) | 1975-07-10 |
Family
ID=26404994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2240317A Expired DE2240317C3 (de) | 1971-08-21 | 1972-08-16 | Verfahren zur Wiedergewinnung erneut einsetzbarer palladiumhaltiger Katalysatoren aus flüssigen Reaktionsgemischen, die bei der Herstellung von Essigsäurearylestern anfallen |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3875020A (enExample) |
| DE (1) | DE2240317C3 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4515983A (en) * | 1983-06-30 | 1985-05-07 | Ashland Oil, Inc. | Manufacture of phenyl esters and phenol |
| EP0244841B1 (en) * | 1986-05-07 | 1992-03-18 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Surface active compounds having a polymerizable moiety |
| DE10024239C1 (de) * | 2000-05-15 | 2001-09-20 | Atotech Deutschland Gmbh | Verfahren zum galvanotechnischen Behandeln von Werkstücken mit einer Palladiumkolloidlösung |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2081721A (en) * | 1934-06-22 | 1937-05-25 | Shell Dev | Solvent extraction process |
| US3324156A (en) * | 1961-12-22 | 1967-06-06 | Gulf Research Development Co | Purification of esters |
| US3600429A (en) * | 1966-12-19 | 1971-08-17 | Bayer Ag | Production of organic esters in the presence of palladium on an alumina support in spinel form |
| US3542852A (en) * | 1966-12-19 | 1970-11-24 | Gulf Research Development Co | Process for the preparation of aromatic esters |
| US3394057A (en) * | 1967-09-12 | 1968-07-23 | Nat Distillers Chem Corp | Separation of vinyl acetate from cyclohexane by extractive distillation |
| FR1575909A (enExample) * | 1968-06-12 | 1969-07-25 | ||
| US3616271A (en) * | 1968-10-25 | 1971-10-26 | Du Pont | Separation of chloroform and/or ethyl acetate from vinyl acetate by extractive distillation |
-
1972
- 1972-08-16 DE DE2240317A patent/DE2240317C3/de not_active Expired
- 1972-08-17 US US281452A patent/US3875020A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3875020A (en) | 1975-04-01 |
| DE2240317A1 (de) | 1973-03-01 |
| DE2240317B2 (enExample) | 1974-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH398564A (de) | Verfahren zur Herstellung von Cyclohexanon | |
| DE3201723C2 (enExample) | ||
| DE3417790A1 (de) | Verfahren zur herstellung von ameisensaeure | |
| DE2240317C3 (de) | Verfahren zur Wiedergewinnung erneut einsetzbarer palladiumhaltiger Katalysatoren aus flüssigen Reaktionsgemischen, die bei der Herstellung von Essigsäurearylestern anfallen | |
| DE2427875B2 (de) | Verfahren zur Gewinnung von Dimethylterephthalat und von Zwischenprodukten der Dimethylterephthalat-Herstellung | |
| DE1643256B2 (de) | Verfahren zur herstellung von trioxan. zusatz zu p 15 43 390.6 | |
| DE69204493T2 (de) | Verfahren zur Reinigung von Dimethylcarbonat. | |
| EP0599214B1 (de) | Verfahren zur kontinuierlichen Herstellung von aromatischen Aldehyden | |
| DE3325983C2 (enExample) | ||
| DE4012534A1 (de) | Gemeinsame herstellung eines aromatischen monoamins und eines aromatischen diamins direkt aus benzol oder einem benzolderivat durch gesteuerte nitrierung und reduktion | |
| DE2057001C3 (de) | Verfahren zur Herstellung von tertiären Aminen | |
| DE2049113A1 (de) | Verfahren zur Herstellung von Adipin saure | |
| DE2202204C2 (de) | Verfahren zur Herstellung von 2-Mercaptobenzimidazol | |
| EP1013638B1 (de) | Verfahren zur Herstellung von Duroldiisocyanat | |
| EP0021211B1 (de) | Verfahren zur Herstellung von Dimethylcarbonat | |
| DE2847104A1 (de) | Verfahren zur herstellung von 2,2-bis (4-hydroxyphenyl)-propan aus den destillationsnebenprodukten desselben | |
| DE2205958C3 (de) | Verfahren zur Reinigung tertiärer aliphatischer Amine | |
| DE69002971T2 (de) | Verfahren zur Rückgewinnung eines Katalysators zur Verwendung bei der Herstellung von 1-(4-isobutylphenyl)propionsäure. | |
| DE3632975C2 (enExample) | ||
| EP0292674A2 (de) | Verfahren zur Herstellung von Propinol | |
| DE3049543A1 (de) | Verfahren zur kontinuierlichen hersellung von 3-alkyl-buten-1-alen | |
| DE1643402C3 (de) | Verfahren zur Herstellung von 2,6-Diphenylphenol | |
| EP0564979B1 (de) | Verfahren zur Herstellung von Dixylylpropan | |
| EP0064180B1 (de) | Verfahren zur Herstellung von 2,3-Dimethylbutan-2,3-diol | |
| DE2048575C3 (de) | Verfahren zur Herstellung von e- Caprolactam aus 6-Hydroperoxyhexansäure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |