DE1670902B2 - Katalytisches Verfahren zur Lactamherstellung - Google Patents
Katalytisches Verfahren zur LactamherstellungInfo
- Publication number
- DE1670902B2 DE1670902B2 DE1670902A DEF0053186A DE1670902B2 DE 1670902 B2 DE1670902 B2 DE 1670902B2 DE 1670902 A DE1670902 A DE 1670902A DE F0053186 A DEF0053186 A DE F0053186A DE 1670902 B2 DE1670902 B2 DE 1670902B2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- regeneration
- reg
- ester
- 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.)
- Pending
Links
- 150000003951 lactams Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 230000003197 catalytic effect Effects 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims description 29
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 13
- 229910052810 boron oxide Inorganic materials 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 8
- 230000007420 reactivation Effects 0.000 claims description 7
- 230000008707 rearrangement Effects 0.000 claims description 6
- 229960002645 boric acid Drugs 0.000 claims description 5
- 235000010338 boric acid Nutrition 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 230000008929 regeneration Effects 0.000 description 17
- 238000011069 regeneration method Methods 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 9
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 150000002923 oximes Chemical class 0.000 description 5
- 239000004408 titanium dioxide Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- -1 orthoboric acid ester Chemical class 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- YYYRKHGKWOQYRC-UHFFFAOYSA-N methanol;methoxyboronic acid Chemical compound OC.COB(O)O YYYRKHGKWOQYRC-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 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
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1670902A DE1670902B2 (de) | 1967-08-09 | 1967-08-09 | Katalytisches Verfahren zur Lactamherstellung |
| GB33780/68A GB1211156A (en) | 1967-08-09 | 1968-07-16 | Improvement in the process for the production of lactams |
| US748963A US3632575A (en) | 1967-08-09 | 1968-07-31 | Process for the production of lactams |
| NL6811222A NL6811222A (https=) | 1967-08-09 | 1968-08-07 | |
| BE719219D BE719219A (https=) | 1967-08-09 | 1968-08-08 | |
| FR1576903D FR1576903A (https=) | 1967-08-09 | 1968-08-09 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1670902A DE1670902B2 (de) | 1967-08-09 | 1967-08-09 | Katalytisches Verfahren zur Lactamherstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1670902A1 DE1670902A1 (de) | 1971-03-18 |
| DE1670902B2 true DE1670902B2 (de) | 1978-07-20 |
Family
ID=7106075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1670902A Pending DE1670902B2 (de) | 1967-08-09 | 1967-08-09 | Katalytisches Verfahren zur Lactamherstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3632575A (https=) |
| BE (1) | BE719219A (https=) |
| DE (1) | DE1670902B2 (https=) |
| FR (1) | FR1576903A (https=) |
| GB (1) | GB1211156A (https=) |
| NL (1) | NL6811222A (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2844880A1 (de) * | 1978-10-14 | 1980-04-30 | Basf Ag | Verfahren zur herstellung von epsilon -caprolactam durch katalytische umlagerung von cyclohexanonoxim |
| US4298503A (en) * | 1980-03-24 | 1981-11-03 | Batalin Oleg E | Method of preparing calcium boron phosphate catalyst |
-
1967
- 1967-08-09 DE DE1670902A patent/DE1670902B2/de active Pending
-
1968
- 1968-07-16 GB GB33780/68A patent/GB1211156A/en not_active Expired
- 1968-07-31 US US748963A patent/US3632575A/en not_active Expired - Lifetime
- 1968-08-07 NL NL6811222A patent/NL6811222A/xx unknown
- 1968-08-08 BE BE719219D patent/BE719219A/xx unknown
- 1968-08-09 FR FR1576903D patent/FR1576903A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE719219A (https=) | 1969-01-16 |
| US3632575A (en) | 1972-01-04 |
| FR1576903A (https=) | 1969-08-01 |
| GB1211156A (en) | 1970-11-04 |
| DE1670902A1 (de) | 1971-03-18 |
| NL6811222A (https=) | 1969-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |