CA1125774A - Process for the continuous manufacture of trioxan - Google Patents
Process for the continuous manufacture of trioxanInfo
- Publication number
- CA1125774A CA1125774A CA341,491A CA341491A CA1125774A CA 1125774 A CA1125774 A CA 1125774A CA 341491 A CA341491 A CA 341491A CA 1125774 A CA1125774 A CA 1125774A
- Authority
- CA
- Canada
- Prior art keywords
- trioxan
- evaporator
- reactor
- vapor
- 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.)
- Expired
Links
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 48
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 150000002924 oxiranes Chemical class 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 235000019256 formaldehyde Nutrition 0.000 description 12
- 229960004279 formaldehyde Drugs 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000008098 formaldehyde solution Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229940093476 ethylene glycol Drugs 0.000 description 3
- 239000007792 gaseous phase Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 150000000180 1,2-diols Chemical class 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- WVYIZGMCLSGZGG-UHFFFAOYSA-N 10-hydroxy-cis-12-octadecenoic acid Natural products CCCCCC=CCC(O)CCCCCCCCC(O)=O WVYIZGMCLSGZGG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000004288 Sodium dehydroacetate Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000003455 independent Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 238000010626 work up procedure 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2853091.8 | 1978-12-08 | ||
| DE19782853091 DE2853091A1 (de) | 1978-12-08 | 1978-12-08 | Verfahren zur kontinuierlichen herstellung von trioxan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1125774A true CA1125774A (en) | 1982-06-15 |
Family
ID=6056660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA341,491A Expired CA1125774A (en) | 1978-12-08 | 1979-12-07 | Process for the continuous manufacture of trioxan |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0012304B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS5581876A (enrdf_load_stackoverflow) |
| AT (1) | ATE644T1 (enrdf_load_stackoverflow) |
| CA (1) | CA1125774A (enrdf_load_stackoverflow) |
| DE (2) | DE2853091A1 (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2943984A1 (de) * | 1979-10-31 | 1981-05-14 | Hoechst Ag, 6000 Frankfurt | Verfahren und vorrichtung zur kontinuierlichen herstellung von trioxan |
| DE3445921A1 (de) * | 1984-12-17 | 1986-06-19 | Hoechst Ag, 6230 Frankfurt | Verfahren zur kontinuierlichen herstellung von trioxan |
| DE59510758D1 (de) * | 1994-09-29 | 2003-09-11 | Ticona Gmbh | Naturumlaufreaktor und Verwendung |
| DE4434845A1 (de) | 1994-09-29 | 1996-04-04 | Hoechst Ag | Naturumlaufreaktor und Verwendung |
| DE102005051974A1 (de) * | 2005-10-31 | 2007-05-03 | Basf Ag | Verfahren zur Herstellung von Trioxan und mindestens einem Comonomer |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE656705A (enrdf_load_stackoverflow) * | 1963-12-05 | |||
| FR1429161A (fr) * | 1964-05-02 | 1966-02-18 | Joseph Meissner Kommanditgesel | Procédé pour la préparation d'une solution de trioxanne |
| IT998150B (it) * | 1973-06-15 | 1976-01-20 | Sir Soc Italiana Resine Spa | Procedimento per la produzione di triossano |
-
1978
- 1978-12-08 DE DE19782853091 patent/DE2853091A1/de not_active Withdrawn
-
1979
- 1979-12-01 DE DE7979104818T patent/DE2962070D1/de not_active Expired
- 1979-12-01 AT AT79104818T patent/ATE644T1/de not_active IP Right Cessation
- 1979-12-01 EP EP79104818A patent/EP0012304B1/de not_active Expired
- 1979-12-07 CA CA341,491A patent/CA1125774A/en not_active Expired
- 1979-12-07 JP JP15825879A patent/JPS5581876A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2853091A1 (de) | 1980-06-26 |
| ATE644T1 (de) | 1982-02-15 |
| DE2962070D1 (en) | 1982-03-11 |
| EP0012304B1 (de) | 1982-02-03 |
| JPS5581876A (en) | 1980-06-20 |
| JPH0147474B2 (enrdf_load_stackoverflow) | 1989-10-13 |
| EP0012304A1 (de) | 1980-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |