DE1670860C3 - Verfahren zur Herstellung von Lactamen - Google Patents
Verfahren zur Herstellung von LactamenInfo
- Publication number
- DE1670860C3 DE1670860C3 DE1670860A DE1670860A DE1670860C3 DE 1670860 C3 DE1670860 C3 DE 1670860C3 DE 1670860 A DE1670860 A DE 1670860A DE 1670860 A DE1670860 A DE 1670860A DE 1670860 C3 DE1670860 C3 DE 1670860C3
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- catalyst
- oxime
- boric acid
- 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
- 150000003951 lactams Chemical class 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000003054 catalyst Substances 0.000 claims description 41
- 230000008707 rearrangement Effects 0.000 claims description 16
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 14
- 239000004327 boric acid Substances 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 40
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000006229 carbon black Substances 0.000 description 12
- 150000002923 oximes Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 6
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241000872198 Serjania polyphylla Species 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- 229910010413 TiO 2 Inorganic materials 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 description 2
- 229910000149 boron phosphate Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- BEZKJRKXUMFDHZ-UHFFFAOYSA-N [O-2].[Al+3].B(O)(O)O.[O-2].[O-2].[Al+3] Chemical compound [O-2].[Al+3].B(O)(O)O.[O-2].[O-2].[Al+3] BEZKJRKXUMFDHZ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 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
- MDIFHVYPHRHKLB-UHFFFAOYSA-N n-(2-methylcyclohexylidene)hydroxylamine Chemical compound CC1CCCCC1=NO MDIFHVYPHRHKLB-UHFFFAOYSA-N 0.000 description 1
- KUVPEPZUXRFFOD-UHFFFAOYSA-N n-cyclodecylidenehydroxylamine Chemical compound ON=C1CCCCCCCCC1 KUVPEPZUXRFFOD-UHFFFAOYSA-N 0.000 description 1
- OENGSNXUALAIFP-UHFFFAOYSA-N n-cycloheptylidenehydroxylamine Chemical compound ON=C1CCCCCC1 OENGSNXUALAIFP-UHFFFAOYSA-N 0.000 description 1
- KTPUHSVFNHULJH-UHFFFAOYSA-N n-cyclooctylidenehydroxylamine Chemical compound ON=C1CCCCCCC1 KTPUHSVFNHULJH-UHFFFAOYSA-N 0.000 description 1
- YGNXYFLJZILPEK-UHFFFAOYSA-N n-cyclopentylidenehydroxylamine Chemical compound ON=C1CCCC1 YGNXYFLJZILPEK-UHFFFAOYSA-N 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0052235 | 1967-04-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1670860A1 DE1670860A1 (de) | 1971-03-11 |
| DE1670860B2 DE1670860B2 (de) | 1973-11-08 |
| DE1670860C3 true DE1670860C3 (de) | 1974-06-06 |
Family
ID=7105295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1670860A Expired DE1670860C3 (de) | 1967-04-25 | 1967-04-25 | Verfahren zur Herstellung von Lactamen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3592809A (esLanguage) |
| BE (1) | BE714133A (esLanguage) |
| CH (1) | CH491922A (esLanguage) |
| DE (1) | DE1670860C3 (esLanguage) |
| FR (1) | FR1561742A (esLanguage) |
| GB (1) | GB1160847A (esLanguage) |
| NL (1) | NL159964C (esLanguage) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2641381A1 (de) * | 1976-09-15 | 1978-03-16 | Bayer Ag | Verwendung von rueckstaenden der cyclohexanonoximdestillation zur herstellung von epsilon-caprolactam |
-
1967
- 1967-04-25 DE DE1670860A patent/DE1670860C3/de not_active Expired
-
1968
- 1968-02-22 CH CH256868A patent/CH491922A/de not_active IP Right Cessation
- 1968-03-08 GB GB11369/68A patent/GB1160847A/en not_active Expired
- 1968-04-16 US US721580A patent/US3592809A/en not_active Expired - Lifetime
- 1968-04-18 NL NL6805499.A patent/NL159964C/xx not_active IP Right Cessation
- 1968-04-24 BE BE714133D patent/BE714133A/xx not_active IP Right Cessation
- 1968-04-25 FR FR1561742D patent/FR1561742A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1670860B2 (de) | 1973-11-08 |
| DE1670860A1 (de) | 1971-03-11 |
| NL159964B (nl) | 1979-04-17 |
| NL159964C (nl) | 1979-09-17 |
| NL6805499A (esLanguage) | 1968-10-28 |
| BE714133A (esLanguage) | 1968-09-16 |
| FR1561742A (esLanguage) | 1969-03-28 |
| US3592809A (en) | 1971-07-13 |
| CH491922A (de) | 1970-06-15 |
| GB1160847A (en) | 1969-08-06 |
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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 |