DE1543664B2 - Kontinuierliches verfahren zur herstellung von weitgehend reinem trioxan - Google Patents
Kontinuierliches verfahren zur herstellung von weitgehend reinem trioxanInfo
- Publication number
- DE1543664B2 DE1543664B2 DE1966H0060035 DEH0060035A DE1543664B2 DE 1543664 B2 DE1543664 B2 DE 1543664B2 DE 1966H0060035 DE1966H0060035 DE 1966H0060035 DE H0060035 A DEH0060035 A DE H0060035A DE 1543664 B2 DE1543664 B2 DE 1543664B2
- Authority
- DE
- Germany
- Prior art keywords
- benzene
- formic acid
- trioxane
- aqueous
- formaldehyde
- 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
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 title claims description 51
- 238000010924 continuous production Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 162
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 88
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 61
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 44
- 235000019253 formic acid Nutrition 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 239000008098 formaldehyde solution Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 229960004365 benzoic acid Drugs 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000005829 trimerization reaction Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000009469 supplementation Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 239000012071 phase Substances 0.000 description 20
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000004094 preconcentration Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000004901 trioxanes Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
- C07D323/04—Six-membered rings
- C07D323/06—Trioxane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR26366A FR1459000A (fr) | 1965-07-28 | 1965-07-28 | Procédé perfectionné pour la préparation du trioxanne |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1543664A1 DE1543664A1 (de) | 1969-08-21 |
| DE1543664B2 true DE1543664B2 (de) | 1976-07-22 |
Family
ID=8585492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1966H0060035 Granted DE1543664B2 (de) | 1965-07-28 | 1966-07-22 | Kontinuierliches verfahren zur herstellung von weitgehend reinem trioxan |
Country Status (9)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2843468A1 (de) * | 1978-10-05 | 1980-04-24 | Hoechst Ag | Verfahren zur gleichzeitigen herstellung von trioxan und cyclischen formalen |
| DE3421300A1 (de) * | 1984-06-08 | 1985-12-12 | Hoechst Ag, 6230 Frankfurt | Verfahren zur gewinnung von trioxan aus waessrigen loesungen durch hochdruck-extraktion |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR970142A (fr) * | 1948-08-03 | 1950-12-29 | Houilleres Bassin Du Nord | Procédé pour l'obtention du trioxane |
| US3197437A (en) * | 1960-08-17 | 1965-07-27 | Celanese Corp | Trioxane polymerization process |
| DE1272931B (de) * | 1962-05-04 | 1968-07-18 | Knapsack Ag | Verfahren zur Herstellung von Trioxan |
-
1965
- 1965-07-28 FR FR26366A patent/FR1459000A/fr not_active Expired
-
1966
- 1966-07-22 DE DE1966H0060035 patent/DE1543664B2/de active Granted
- 1966-07-26 GB GB33512/66A patent/GB1080950A/en not_active Expired
- 1966-07-26 CH CH1079366A patent/CH456635A/fr unknown
- 1966-07-26 IL IL26220A patent/IL26220A/xx unknown
- 1966-07-26 US US568045A patent/US3522278A/en not_active Expired - Lifetime
- 1966-07-28 NL NL6610651A patent/NL6610651A/xx unknown
- 1966-07-28 BE BE684730D patent/BE684730A/xx unknown
- 1966-07-28 JP JP41049126A patent/JPS495351B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL26220A (en) | 1970-02-19 |
| GB1080950A (en) | 1967-08-31 |
| FR1459000A (fr) | 1966-04-29 |
| CH456635A (fr) | 1968-07-31 |
| US3522278A (en) | 1970-07-28 |
| BE684730A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-01-03 |
| DE1543664A1 (de) | 1969-08-21 |
| NL6610651A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-01-30 |
| JPS495351B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-02-06 |
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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 |