DE1301558B - Verfahren zur Herstellung von Poly-(aethylenglykolterephthalat) - Google Patents
Verfahren zur Herstellung von Poly-(aethylenglykolterephthalat)Info
- Publication number
- DE1301558B DE1301558B DEV23779A DEV0023779A DE1301558B DE 1301558 B DE1301558 B DE 1301558B DE V23779 A DEV23779 A DE V23779A DE V0023779 A DEV0023779 A DE V0023779A DE 1301558 B DE1301558 B DE 1301558B
- Authority
- DE
- Germany
- Prior art keywords
- ethylene glycol
- poly
- polycondensation
- transesterification
- terephthalate
- 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
- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 title claims description 15
- 229920001223 polyethylene glycol Polymers 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 27
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 22
- 238000005809 transesterification reaction Methods 0.000 claims description 17
- 238000006068 polycondensation reaction Methods 0.000 claims description 14
- -1 hexafluorosilicic acid Chemical compound 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 9
- LPDWOEAWNMGOAO-UHFFFAOYSA-N (4,7,8-trimethylquinolin-2-yl)hydrazine Chemical compound CC1=CC(NN)=NC2=C(C)C(C)=CC=C21 LPDWOEAWNMGOAO-UHFFFAOYSA-N 0.000 claims description 7
- 229940074568 calcium hexafluorosilicate Drugs 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 description 19
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
- 239000001639 calcium acetate Substances 0.000 description 2
- 229960005147 calcium acetate Drugs 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- GKEUSXYNGGGCOQ-UHFFFAOYSA-I calcium diacetyloxystibanyl acetate diacetate Chemical compound C(C)(=O)[O-].[Sb+3].[Ca+2].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-] GKEUSXYNGGGCOQ-UHFFFAOYSA-I 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- RXSHXLOMRZJCLB-UHFFFAOYSA-L strontium;diacetate Chemical compound [Sr+2].CC([O-])=O.CC([O-])=O RXSHXLOMRZJCLB-UHFFFAOYSA-L 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- XRBXGZZMKCBTFP-UHFFFAOYSA-N 4-(2,2-dihydroxyethoxycarbonyl)benzoic acid Chemical compound OC(O)COC(=O)C1=CC=C(C(O)=O)C=C1 XRBXGZZMKCBTFP-UHFFFAOYSA-N 0.000 description 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
- 150000001553 barium compounds Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- ONIHPYYWNBVMID-UHFFFAOYSA-N diethyl benzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C=C1 ONIHPYYWNBVMID-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004761 hexafluorosilicates Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, or compounds thereof
-
- 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
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/87—Non-metals or inter-compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV23779A DE1301558B (de) | 1963-03-09 | 1963-03-09 | Verfahren zur Herstellung von Poly-(aethylenglykolterephthalat) |
| CH95664A CH430211A (de) | 1963-03-09 | 1964-01-28 | Verfahren zur Herstellung von Polyäthylenterephthalat unter Verwendung von Erdalkali enthaltenden Umesterungskatalysatoren |
| BE643154D BE643154A (en, 2012) | 1963-03-09 | 1964-01-30 | |
| AT78764A AT248122B (de) | 1963-03-09 | 1964-01-31 | Verfahren zur Herstellung von Polyäthylenterephthalat unter Verwendung von Erdalkali enthaltenden Umesterungskatalysatoren |
| GB7804/64A GB1013107A (en) | 1963-03-09 | 1964-02-25 | A process for the production of polyesters of terephthalic acid |
| US348846A US3346542A (en) | 1963-03-09 | 1964-03-02 | Addition of calcium hexafluorosilicate or hexafluorosilicic acid as haze inhibitor during two-stage catalytic production of polyethylene terephthalate |
| NL6402356A NL6402356A (en, 2012) | 1963-03-09 | 1964-03-06 | |
| FR966474A FR1386763A (fr) | 1963-03-09 | 1964-03-06 | Procédé pour la fabrication de téréphtalate de polyéthylène avec utilisation de catalyseurs de réestérification contenant des composés alcalino-terreux |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV23779A DE1301558B (de) | 1963-03-09 | 1963-03-09 | Verfahren zur Herstellung von Poly-(aethylenglykolterephthalat) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1301558B true DE1301558B (de) | 1969-08-21 |
Family
ID=7580757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEV23779A Pending DE1301558B (de) | 1963-03-09 | 1963-03-09 | Verfahren zur Herstellung von Poly-(aethylenglykolterephthalat) |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3346542A (en, 2012) |
| AT (1) | AT248122B (en, 2012) |
| BE (1) | BE643154A (en, 2012) |
| CH (1) | CH430211A (en, 2012) |
| DE (1) | DE1301558B (en, 2012) |
| FR (1) | FR1386763A (en, 2012) |
| GB (1) | GB1013107A (en, 2012) |
| NL (1) | NL6402356A (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3425998A (en) * | 1966-10-13 | 1969-02-04 | Fmc Corp | Lead silicofluoride as a transesterification catalyst |
| US3506618A (en) * | 1966-11-14 | 1970-04-14 | Fmc Corp | Hexafluorosilicate additives in polyester preparation |
| US3488318A (en) * | 1968-03-25 | 1970-01-06 | Fmc Corp | Polyesters stabilized with hydrocarbyl trialkoxy silanes |
| US3475371A (en) * | 1968-03-25 | 1969-10-28 | Fmc Corp | Polyesters stabilized with aliphatic orthosilicates |
| US5567758A (en) * | 1994-08-26 | 1996-10-22 | Toyo Boseki Kabushiki Kaisha | Thermoplastic polyester resin composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3068204A (en) * | 1958-08-15 | 1962-12-11 | Eastman Kodak Co | Fluotitanate catalysts for preparing linear polyesters |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2577618A (en) * | 1946-12-18 | 1951-12-04 | American Cyanamid Co | Rubberlike cured polyesters containing calcium silicate and process of producing same |
| US3228913A (en) * | 1953-04-20 | 1966-01-11 | Allied Chem | Polyesters of 4, 4'-dicarboxydiphenylsulfone with glycols and fibers thereof |
| US3129178A (en) * | 1961-05-03 | 1964-04-14 | Nopco Chem Co | Process for preparing materials having improved physical characteristics |
| US3201506A (en) * | 1962-08-09 | 1965-08-17 | Du Pont | Addition of magnesium silicate to a polyester in the manufacture of oriented film |
-
1963
- 1963-03-09 DE DEV23779A patent/DE1301558B/de active Pending
-
1964
- 1964-01-28 CH CH95664A patent/CH430211A/de unknown
- 1964-01-30 BE BE643154D patent/BE643154A/xx unknown
- 1964-01-31 AT AT78764A patent/AT248122B/de active
- 1964-02-25 GB GB7804/64A patent/GB1013107A/en not_active Expired
- 1964-03-02 US US348846A patent/US3346542A/en not_active Expired - Lifetime
- 1964-03-06 NL NL6402356A patent/NL6402356A/xx unknown
- 1964-03-06 FR FR966474A patent/FR1386763A/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3068204A (en) * | 1958-08-15 | 1962-12-11 | Eastman Kodak Co | Fluotitanate catalysts for preparing linear polyesters |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1386763A (fr) | 1965-01-22 |
| CH430211A (de) | 1967-02-15 |
| NL6402356A (en, 2012) | 1964-09-10 |
| BE643154A (en, 2012) | 1964-05-15 |
| US3346542A (en) | 1967-10-10 |
| GB1013107A (en) | 1965-12-15 |
| AT248122B (de) | 1966-07-11 |
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