DE1258858C2 - Verfahren zur herstellung von epsilon-caprolacton und seiner alkylderivate - Google Patents
Verfahren zur herstellung von epsilon-caprolacton und seiner alkylderivateInfo
- Publication number
- DE1258858C2 DE1258858C2 DE1965D0048296 DED0048296A DE1258858C2 DE 1258858 C2 DE1258858 C2 DE 1258858C2 DE 1965D0048296 DE1965D0048296 DE 1965D0048296 DE D0048296 A DED0048296 A DE D0048296A DE 1258858 C2 DE1258858 C2 DE 1258858C2
- Authority
- DE
- Germany
- Prior art keywords
- cyclohexanone
- caprolactone
- reaction
- acid
- aqueous
- 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
- 238000000034 method Methods 0.000 title claims description 22
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- -1 aliphatic peracids Chemical class 0.000 claims description 2
- JHIVVAPYMSGYDF-PTQBSOBMSA-N cyclohexanone Chemical class O=[13C]1CCCCC1 JHIVVAPYMSGYDF-PTQBSOBMSA-N 0.000 claims 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- IYBOGQYZTIIPNI-UHFFFAOYSA-N 2-methylhexano-6-lactone Chemical class CC1CCCCOC1=O IYBOGQYZTIIPNI-UHFFFAOYSA-N 0.000 description 2
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- DQGRFSFYQIYMHB-UHFFFAOYSA-N acetaldehyde;ethaneperoxoic acid Chemical compound CC=O.CC(=O)OO DQGRFSFYQIYMHB-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- ZUYKJZQOPXDNOK-UHFFFAOYSA-N 2-(ethylamino)-2-thiophen-2-ylcyclohexan-1-one;hydrochloride Chemical class Cl.C=1C=CSC=1C1(NCC)CCCCC1=O ZUYKJZQOPXDNOK-UHFFFAOYSA-N 0.000 description 1
- ZDCYWXYPRPCJOY-UHFFFAOYSA-N 3,4-dimethylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1C ZDCYWXYPRPCJOY-UHFFFAOYSA-N 0.000 description 1
- CRDDUKDDRKRCFN-UHFFFAOYSA-N 4,5-dimethyloxepan-2-one Chemical class CC1CC(=O)OCCC1C CRDDUKDDRKRCFN-UHFFFAOYSA-N 0.000 description 1
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003385 ring cleavage reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965D0048296 DE1258858C2 (de) | 1965-09-25 | 1965-09-25 | Verfahren zur herstellung von epsilon-caprolacton und seiner alkylderivate |
| FR73754A FR1490173A (fr) | 1965-09-25 | 1966-08-22 | Procédé de fabrication de la caprolactone-xi et de ses dérivés alkylés |
| FI662212A FI44385C (fi) | 1965-09-25 | 1966-08-24 | Tapa valmistaa E-kaprolaktonia ja sen alkyylijohdannaisia |
| CH1267366A CH475978A (de) | 1965-09-25 | 1966-09-01 | Verfahren zur Herstellung von 8-Caprolacton und seiner Alkylderivate |
| US577584A US3517033A (en) | 1965-09-25 | 1966-09-07 | Process for the production of epsilon-caprolactone and its alkyl derivatives |
| ES0331182A ES331182A1 (es) | 1965-09-25 | 1966-09-14 | Un procedimiento para la preparacion de epsilon-caprolactona y de sus derivados alcohilicos. |
| GB42207/66A GB1096967A (en) | 1965-09-25 | 1966-09-21 | A process for the production of ªŠ-caprolactone and its alkyl derivatives |
| NL6613409A NL6613409A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-09-25 | 1966-09-22 | |
| SE12878/66A SE316461B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-09-25 | 1966-09-23 | |
| BE687360D BE687360A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-09-25 | 1966-09-23 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965D0048296 DE1258858C2 (de) | 1965-09-25 | 1965-09-25 | Verfahren zur herstellung von epsilon-caprolacton und seiner alkylderivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1258858B DE1258858B (de) | 1968-01-18 |
| DE1258858C2 true DE1258858C2 (de) | 1976-08-12 |
Family
ID=7051052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1965D0048296 Expired DE1258858C2 (de) | 1965-09-25 | 1965-09-25 | Verfahren zur herstellung von epsilon-caprolacton und seiner alkylderivate |
Country Status (10)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0026311A1 (de) * | 1979-08-28 | 1981-04-08 | Degussa Aktiengesellschaft | Verfahren zur Herstellung von sehr reinem epsilon-Caprolacton |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2920436A1 (de) * | 1979-05-19 | 1980-12-04 | Bayer Ag | Verfahren zur herstellung von epsilon -caprolacton |
| FR2500453A1 (fr) * | 1981-02-20 | 1982-08-27 | Ugine Kuhlmann | Procede d'obtention de l'epsilon-caprolactone |
| US4870192A (en) * | 1985-08-12 | 1989-09-26 | Mobil Oil Corporation | Production of lactones and omega-hydroxycarboxylic acids |
| US4988825A (en) * | 1986-09-23 | 1991-01-29 | Cooper Union Research Foundation, Inc. | Oxidation of aldehydes and ketones using alkali metal perborates |
| CN115738338B (zh) * | 2022-11-23 | 2025-08-26 | 浙江正益生物科技有限公司 | 一种同时生产ε-己内酯和巴豆酸的方法及其系统 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3064008A (en) * | 1962-11-13 | I i i i i i | ||
| US3056802A (en) * | 1960-10-04 | 1962-10-02 | Union Carbide Corp | Alpha-halo lactones |
-
1965
- 1965-09-25 DE DE1965D0048296 patent/DE1258858C2/de not_active Expired
-
1966
- 1966-08-22 FR FR73754A patent/FR1490173A/fr not_active Expired
- 1966-08-24 FI FI662212A patent/FI44385C/fi active
- 1966-09-01 CH CH1267366A patent/CH475978A/de not_active IP Right Cessation
- 1966-09-07 US US577584A patent/US3517033A/en not_active Expired - Lifetime
- 1966-09-14 ES ES0331182A patent/ES331182A1/es not_active Expired
- 1966-09-21 GB GB42207/66A patent/GB1096967A/en not_active Expired
- 1966-09-22 NL NL6613409A patent/NL6613409A/xx unknown
- 1966-09-23 SE SE12878/66A patent/SE316461B/xx unknown
- 1966-09-23 BE BE687360D patent/BE687360A/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0026311A1 (de) * | 1979-08-28 | 1981-04-08 | Degussa Aktiengesellschaft | Verfahren zur Herstellung von sehr reinem epsilon-Caprolacton |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6613409A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-03-28 |
| FR1490173A (fr) | 1967-07-28 |
| CH475978A (de) | 1969-07-31 |
| FI44385B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-08-02 |
| GB1096967A (en) | 1967-12-29 |
| US3517033A (en) | 1970-06-23 |
| ES331182A1 (es) | 1967-07-01 |
| BE687360A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-03-01 |
| FI44385C (fi) | 1971-11-10 |
| SE316461B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-10-27 |
| DE1258858B (de) | 1968-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |