DE1570973A1 - Verfahren zur kontinuierlichen Umesterung von Dimethylterephthalat mit Glykol - Google Patents
Verfahren zur kontinuierlichen Umesterung von Dimethylterephthalat mit GlykolInfo
- Publication number
- DE1570973A1 DE1570973A1 DE1965M0065382 DEM0065382A DE1570973A1 DE 1570973 A1 DE1570973 A1 DE 1570973A1 DE 1965M0065382 DE1965M0065382 DE 1965M0065382 DE M0065382 A DEM0065382 A DE M0065382A DE 1570973 A1 DE1570973 A1 DE 1570973A1
- Authority
- DE
- Germany
- Prior art keywords
- methanol
- dimethyl terephthalate
- reaction
- glycol
- acid esters
- 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
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 14
- 238000005809 transesterification reaction Methods 0.000 title claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 6
- 238000006068 polycondensation reaction Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- -1 Polyethylene terephthalate Polymers 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 239000004246 zinc acetate 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/785—Preparation processes characterised by the apparatus used
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/245—Stationary reactors without moving elements inside placed in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00076—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements inside the reactor
- B01J2219/00083—Coils
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00101—Reflux columns
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00761—Details of the reactor
- B01J2219/00763—Baffles
- B01J2219/00765—Baffles attached to the reactor wall
- B01J2219/00777—Baffles attached to the reactor wall horizontal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965M0065382 DE1570973A1 (de) | 1965-05-28 | 1965-05-28 | Verfahren zur kontinuierlichen Umesterung von Dimethylterephthalat mit Glykol |
| NL6513493A NL6513493A (enrdf_load_stackoverflow) | 1965-05-28 | 1965-10-19 | |
| AT952765A AT272651B (de) | 1965-05-28 | 1965-10-21 | Verfahren und Vorrichtung zur kontinuierlichen Umesterung von Dicarbonsäureestern mit Alkoholen, vorzugsweise von Dimethylterephthalat mit Äthylenglykol |
| CH1463365A CH466258A (de) | 1965-05-28 | 1965-10-22 | Verfahren zur kontinuierlichen Umesterung von Dicarbonsäureestern mit Alkoholen |
| GB47746/65A GB1108010A (en) | 1965-05-28 | 1965-11-10 | Improvements in or relating to transesterification reactions |
| FR39823A FR1456241A (fr) | 1965-05-28 | 1965-11-25 | Procédé et appareillage pour la transestérification continue de téréphtalate dediméthyle par l'éthylène glycol |
| BE681531D BE681531A (enrdf_load_stackoverflow) | 1965-05-28 | 1966-05-24 | |
| ES0328536A ES328536A1 (es) | 1965-05-28 | 1966-06-30 | Un dispositivo para la transesterificacion continua de esteres de acidos dicarboxilicos con alcoholes. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965M0065382 DE1570973A1 (de) | 1965-05-28 | 1965-05-28 | Verfahren zur kontinuierlichen Umesterung von Dimethylterephthalat mit Glykol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1570973A1 true DE1570973A1 (de) | 1970-02-26 |
Family
ID=7311427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1965M0065382 Pending DE1570973A1 (de) | 1965-05-28 | 1965-05-28 | Verfahren zur kontinuierlichen Umesterung von Dimethylterephthalat mit Glykol |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT272651B (enrdf_load_stackoverflow) |
| BE (1) | BE681531A (enrdf_load_stackoverflow) |
| CH (1) | CH466258A (enrdf_load_stackoverflow) |
| DE (1) | DE1570973A1 (enrdf_load_stackoverflow) |
| ES (1) | ES328536A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1456241A (enrdf_load_stackoverflow) |
| GB (1) | GB1108010A (enrdf_load_stackoverflow) |
| NL (1) | NL6513493A (enrdf_load_stackoverflow) |
-
1965
- 1965-05-28 DE DE1965M0065382 patent/DE1570973A1/de active Pending
- 1965-10-19 NL NL6513493A patent/NL6513493A/xx unknown
- 1965-10-21 AT AT952765A patent/AT272651B/de active
- 1965-10-22 CH CH1463365A patent/CH466258A/de unknown
- 1965-11-10 GB GB47746/65A patent/GB1108010A/en not_active Expired
- 1965-11-25 FR FR39823A patent/FR1456241A/fr not_active Expired
-
1966
- 1966-05-24 BE BE681531D patent/BE681531A/xx unknown
- 1966-06-30 ES ES0328536A patent/ES328536A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES328536A1 (es) | 1967-04-01 |
| CH466258A (de) | 1968-12-15 |
| AT272651B (de) | 1969-07-10 |
| NL6513493A (enrdf_load_stackoverflow) | 1966-11-29 |
| BE681531A (enrdf_load_stackoverflow) | 1966-10-31 |
| GB1108010A (en) | 1968-03-27 |
| FR1456241A (fr) | 1966-10-21 |
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