EP1945689A1 - Procede de fabrication de trioxane et d au moins un comonomere - Google Patents
Procede de fabrication de trioxane et d au moins un comonomereInfo
- Publication number
- EP1945689A1 EP1945689A1 EP06807603A EP06807603A EP1945689A1 EP 1945689 A1 EP1945689 A1 EP 1945689A1 EP 06807603 A EP06807603 A EP 06807603A EP 06807603 A EP06807603 A EP 06807603A EP 1945689 A1 EP1945689 A1 EP 1945689A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- stream
- comonomer
- formaldehyde
- trioxane
- water
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 title claims description 90
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 310
- 238000004821 distillation Methods 0.000 claims abstract description 130
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 83
- 239000007858 starting material Substances 0.000 claims abstract description 41
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 20
- 239000011541 reaction mixture Substances 0.000 claims abstract description 16
- -1 comonomer Chemical compound 0.000 claims abstract description 15
- 229920001577 copolymer Polymers 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 26
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 25
- 238000000066 reactive distillation Methods 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 11
- 239000008098 formaldehyde solution Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 239000011552 falling film Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 238000011144 upstream manufacturing Methods 0.000 claims description 2
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 abstract 6
- 238000012856 packing Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229920006324 polyoxymethylene Polymers 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- CZLMRJZAHXYRIX-UHFFFAOYSA-N 1,3-dioxepane Chemical compound C1CCOCOC1 CZLMRJZAHXYRIX-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FZIIBDOXPQOKBP-UHFFFAOYSA-N 2-methyloxetane Chemical compound CC1CCO1 FZIIBDOXPQOKBP-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- STENYDAIMALDKF-UHFFFAOYSA-N cyclobutane-1,3-diol Chemical class OC1CC(O)C1 STENYDAIMALDKF-UHFFFAOYSA-N 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical class OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001570 methylene group Chemical class [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
- 238000005373 pervaporation Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/10—Polymerisation of cyclic oligomers of formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/18—Copolymerisation of aldehydes or ketones
- C08G2/20—Copolymerisation of aldehydes or ketones with other aldehydes or ketones
-
- 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
- Y02P20/10—Process efficiency
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Definitions
- Comonomers prepared by the process according to the invention are, for example, cyclic ethers of the formula (I)
- the at least one comonomer starting material is selected in each case such that the desired comonomer is produced by reaction with formaldehyde under the conditions prevailing in the reactor.
- the stream B1 enriched in trioxane and comonomer generally contains 25 to 80% by weight of trioxane, 10 to 65% by weight of comonomer, 1 to 20% by weight of formaldehyde and 5 to 25% by weight of water.
- the stream B1 preferably contains from 30 to 60% by weight of trioxane, from 15 to 60% by weight of comonomer, from 1 to 15% by weight of formaldehyde and from 5 to 20% by weight of water.
- the stream B2 generally contains 40 to 75% by weight of formaldehyde, 15 to 50% by weight of water and 5 to 50% by weight of the at least one comonomer starting material.
- the stream B2 preferably contains from 40 to 75% by weight of formaldehyde, from 15 to 50% by weight of water and from 10 to 40% by weight of the at least one comonomer starting material.
- stream B2 may contain at most 5% by weight, preferably not more than 3% by weight, and in particular not more than 2% by weight, of trioxane and comonomer.
- the reaction mixture A1 containing the trioxane, comonomer, formaldehyde, water and optionally comonomer starting material of the distillation column, in which the first distillation stage b) is carried out preferably added gaseous or liquid as side feed.
- the stream B1 enriched in trioxane and comonomer is preferably taken off as top draw stream and stream B2 containing essentially water, formaldehyde and optionally comonomer starting material as bottom draw stream.
- the aqueous formaldehyde solution E1 fed to the concentration unit generally contains from 25 to 65% by weight of formaldehyde and from 35 to 75% by weight of water, preferably from 30 to 60% by weight of formaldehyde and from 40 to 70% by weight of water.
- the formaldehyde-rich stream E3 obtained in the concentration generally contains at least 50% by weight of formaldehyde, preferably at least 55% by weight of formaldehyde.
- the low-formaldehyde stream E2 generally contains at most 35% by weight of formaldehyde, preferably at most 30% by weight of formaldehyde.
- the formaldehyde-rich stream E3 obtained during the concentration preferably accumulates as the bottom draw stream and the formaldehyde-lean stream E2 as top or bottom draw stream.
- the low-formaldehyde stream E2 is preferably fed to the third distillation stage.
- This stream is fed to a second distillation column and in this at a bottom temperature of 167 ° C and a pressure of 5 bar in a withdrawn at the top of the second distillation column stream of 15.6 kg / h, the 48.1 wt .-% Trioxane, 23.9 wt .-% water, 22.4 wt .-% dioxolane and 5.6 wt .-% formaldehyde, and a withdrawn at the bottom product stream of 3.4 kg / h, the 99.4 wt.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
L'invention concerne un procédé de fabrication de trioxane et d'au moins un comonomère pour la fabrication de (co)polymères à base de trioxane, selon lequel dans une première étape du formaldéhyde et au moins un réactif comonomère sont transformés en solution aqueuse en du trioxane et en un comonomère, un mélange réactionnel A1 contenant du trioxane, un comonomère, du formaldéhyde, de l'eau et éventuellement un réactif comonomère étant obtenu. Dans une deuxième étape, le mélange réactionnel A1 est distillé lors d'une première étape de distillation à une première pression, un flux B1 enrichi en trioxane et en comonomère et un flux B2 contenant essentiellement de l'eau, du formaldéhyde et l'éventuel réactif monomère étant obtenus. Dans une troisième étape, le flux B1 est distillé lors d'une seconde étape de distillation à une pression supérieure à la pression utilisée lors de la première étape de distillation, un flux C1 contenant du trioxane, un comonomère et de l'eau et un flux C2 constituant le produit final contenant essentiellement un comonomère et du trioxane étant obtenus.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005051974A DE102005051974A1 (de) | 2005-10-31 | 2005-10-31 | Verfahren zur Herstellung von Trioxan und mindestens einem Comonomer |
| PCT/EP2006/067851 WO2007051762A1 (fr) | 2005-10-31 | 2006-10-27 | Procede de fabrication de trioxane et d’au moins un comonomere |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1945689A1 true EP1945689A1 (fr) | 2008-07-23 |
Family
ID=37478874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP06807603A Withdrawn EP1945689A1 (fr) | 2005-10-31 | 2006-10-27 | Procede de fabrication de trioxane et d au moins un comonomere |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20080283384A1 (fr) |
| EP (1) | EP1945689A1 (fr) |
| JP (1) | JP2009513687A (fr) |
| KR (1) | KR20080075126A (fr) |
| CN (1) | CN101321789A (fr) |
| AU (1) | AU2006310554A1 (fr) |
| BR (1) | BRPI0618065A2 (fr) |
| CA (1) | CA2627080A1 (fr) |
| DE (1) | DE102005051974A1 (fr) |
| NO (1) | NO20081897L (fr) |
| WO (1) | WO2007051762A1 (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2010256520B2 (en) * | 2009-06-04 | 2016-02-25 | Genomatica, Inc. | Process of separating components of a fermentation broth |
| US8829207B2 (en) * | 2011-06-24 | 2014-09-09 | Eastman Chemical Company | Production of cyclic acetals by reactive distillation |
| US8969598B2 (en) | 2011-06-24 | 2015-03-03 | Eastman Chemical Company | Production of cyclic acetals or ketals using liquid-phase acid catalysts |
| US9388105B2 (en) | 2011-06-24 | 2016-07-12 | Eastman Chemical Company | Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals |
| US8829206B2 (en) | 2011-06-24 | 2014-09-09 | Eastman Chemical Company | Production of cyclic acetals or ketals using solid acid catalysts |
| US9056313B2 (en) | 2011-06-24 | 2015-06-16 | Eastman Chemical Company | Catalysts for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals |
| US9000229B2 (en) | 2011-06-24 | 2015-04-07 | Eastman Chemical Company | Production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals |
| US8785697B2 (en) | 2011-06-24 | 2014-07-22 | Eastman Chemical Company | Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals |
| CN108031132A (zh) * | 2018-01-12 | 2018-05-15 | 无锡宝南机器制造有限公司 | 双塔降膜蒸发器组 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1668687B2 (de) * | 1968-02-24 | 1976-06-24 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue 18-methyl-5alpha-h-androstane, verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel |
| DE2843468A1 (de) * | 1978-10-05 | 1980-04-24 | Hoechst Ag | Verfahren zur gleichzeitigen herstellung von trioxan und cyclischen formalen |
| DE2853091A1 (de) * | 1978-12-08 | 1980-06-26 | Hoechst Ag | Verfahren zur kontinuierlichen herstellung von trioxan |
| DE2912767A1 (de) * | 1979-03-30 | 1980-10-09 | Hoechst Ag | Verfahren zur kontinuierlichen herstellung von trioxan |
| 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 |
| DE19630670A1 (de) * | 1996-07-30 | 1998-02-05 | Basf Ag | Verfahren zur Herstellung von Aminen aus Olefinen an Zeolithen mit NES-Struktur |
| DE19732291A1 (de) * | 1997-07-26 | 1999-01-28 | Basf Ag | Verfahren zur Abtrennung von Trioxan |
| DE10215976A1 (de) * | 2002-04-11 | 2003-10-23 | Basf Ag | Herstellung von Polyoxymethylen und dafür geeignete Katalysatoren III |
| DE10361516A1 (de) * | 2003-12-23 | 2005-07-28 | Basf Ag | Verfahren zur Abtrennung von Trioxan aus einem Trioxan/Formaldehyd/Wasser-Gemisch mittels Druckwechsel-Rektifikation |
-
2005
- 2005-10-31 DE DE102005051974A patent/DE102005051974A1/de not_active Withdrawn
-
2006
- 2006-10-27 BR BRPI0618065A patent/BRPI0618065A2/pt not_active IP Right Cessation
- 2006-10-27 JP JP2008538342A patent/JP2009513687A/ja not_active Withdrawn
- 2006-10-27 EP EP06807603A patent/EP1945689A1/fr not_active Withdrawn
- 2006-10-27 CN CNA2006800451230A patent/CN101321789A/zh active Pending
- 2006-10-27 US US12/091,976 patent/US20080283384A1/en not_active Abandoned
- 2006-10-27 AU AU2006310554A patent/AU2006310554A1/en not_active Abandoned
- 2006-10-27 WO PCT/EP2006/067851 patent/WO2007051762A1/fr not_active Ceased
- 2006-10-27 CA CA002627080A patent/CA2627080A1/fr not_active Abandoned
- 2006-10-27 KR KR1020087013040A patent/KR20080075126A/ko not_active Withdrawn
-
2008
- 2008-04-22 NO NO20081897A patent/NO20081897L/no not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2007051762A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0618065A2 (pt) | 2016-09-13 |
| KR20080075126A (ko) | 2008-08-14 |
| CN101321789A (zh) | 2008-12-10 |
| WO2007051762A1 (fr) | 2007-05-10 |
| JP2009513687A (ja) | 2009-04-02 |
| DE102005051974A1 (de) | 2007-05-03 |
| NO20081897L (no) | 2008-05-27 |
| US20080283384A1 (en) | 2008-11-20 |
| CA2627080A1 (fr) | 2007-05-10 |
| AU2006310554A1 (en) | 2007-05-10 |
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