CA1081245A - Terephthalic acid ethylene glycol esters, their production and use in the production of polyester polymers - Google Patents
Terephthalic acid ethylene glycol esters, their production and use in the production of polyester polymersInfo
- Publication number
- CA1081245A CA1081245A CA245,053A CA245053A CA1081245A CA 1081245 A CA1081245 A CA 1081245A CA 245053 A CA245053 A CA 245053A CA 1081245 A CA1081245 A CA 1081245A
- Authority
- CA
- Canada
- Prior art keywords
- product
- glycol
- ester
- weight
- ethylene glycol
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 229920000728 polyester Polymers 0.000 title abstract description 8
- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical class OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 title abstract 2
- 229920000642 polymer Polymers 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 147
- 239000000047 product Substances 0.000 claims abstract description 73
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 26
- 150000002148 esters Chemical class 0.000 claims abstract description 25
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 22
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000009833 condensation Methods 0.000 claims abstract description 13
- 230000005494 condensation Effects 0.000 claims abstract description 13
- 238000007711 solidification Methods 0.000 claims abstract description 12
- 230000008023 solidification Effects 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 10
- 239000012263 liquid product Substances 0.000 claims abstract description 9
- 239000000155 melt Substances 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- 239000008188 pellet Substances 0.000 claims abstract description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 31
- -1 terephthalic acid ethylene glycol ester Chemical class 0.000 claims description 16
- 238000006068 polycondensation reaction Methods 0.000 claims description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 239000003426 co-catalyst Substances 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims 2
- 239000012265 solid product Substances 0.000 claims 2
- 239000003381 stabilizer Substances 0.000 claims 2
- 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 claims 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 11
- 229940093476 ethylene glycol Drugs 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 238000005755 formation reaction Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000005020 polyethylene terephthalate Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000002844 continuous effect Effects 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 229940093470 ethylene Drugs 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical group [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 3
- MMINFSMURORWKH-UHFFFAOYSA-N 3,6-dioxabicyclo[6.2.2]dodeca-1(10),8,11-triene-2,7-dione Chemical group O=C1OCCOC(=O)C2=CC=C1C=C2 MMINFSMURORWKH-UHFFFAOYSA-N 0.000 description 2
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical group C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 101100386518 Caenorhabditis elegans dbl-1 gene Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 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 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 241001080526 Vertica Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- CUZMQPZYCDIHQL-VCTVXEGHSA-L calcium;(2s)-1-[(2s)-3-[(2r)-2-(cyclohexanecarbonylamino)propanoyl]sulfanyl-2-methylpropanoyl]pyrrolidine-2-carboxylate Chemical compound [Ca+2].N([C@H](C)C(=O)SC[C@@H](C)C(=O)N1[C@@H](CCC1)C([O-])=O)C(=O)C1CCCCC1.N([C@H](C)C(=O)SC[C@@H](C)C(=O)N1[C@@H](CCC1)C([O-])=O)C(=O)C1CCCCC1 CUZMQPZYCDIHQL-VCTVXEGHSA-L 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000727 fraction Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000009991 pite Nutrition 0.000 description 1
- 244000293655 pite Species 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 150000003673 urethanes Chemical class 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
- C07C69/82—Terephthalic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752504156 DE2504156A1 (de) | 1975-02-01 | 1975-02-01 | Niedermolekulare terephthalsaeure- aethylenglykolester, ihre herstellung und verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1081245A true CA1081245A (en) | 1980-07-08 |
Family
ID=5937840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA245,053A Expired CA1081245A (en) | 1975-02-01 | 1976-02-02 | Terephthalic acid ethylene glycol esters, their production and use in the production of polyester polymers |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS51101946A (OSRAM) |
| BE (1) | BE838080A (OSRAM) |
| BR (1) | BR7600251A (OSRAM) |
| CA (1) | CA1081245A (OSRAM) |
| DD (1) | DD123738A5 (OSRAM) |
| DE (1) | DE2504156A1 (OSRAM) |
| FR (1) | FR2299310A1 (OSRAM) |
| GB (1) | GB1511412A (OSRAM) |
| IN (1) | IN145144B (OSRAM) |
| IT (1) | IT1053475B (OSRAM) |
| MX (1) | MX3016E (OSRAM) |
| NL (1) | NL7600984A (OSRAM) |
| PL (1) | PL103014B1 (OSRAM) |
| RO (1) | RO69845A (OSRAM) |
| SU (1) | SU625598A3 (OSRAM) |
| TR (1) | TR18730A (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986001200A1 (fr) * | 1984-08-14 | 1986-02-27 | Mitsubishi Chemical Industries Limited | Procede de preparation de biphenyltetracarboxylate de tetramethyle |
| WO2001010812A1 (en) | 1999-08-04 | 2001-02-15 | Aies Co., Ltd. | METHODS FOR THE PREPARATION OR PURIFICATION OF BIS-β-HYDROXYETHYL TEREPHTHALATE |
| US6380352B1 (en) * | 2000-08-29 | 2002-04-30 | Eastman Chemical Company | Polyester precursor purification process |
-
1975
- 1975-02-01 DE DE19752504156 patent/DE2504156A1/de not_active Withdrawn
- 1975-11-24 MX MX100139U patent/MX3016E/es unknown
- 1975-12-15 DD DD190149A patent/DD123738A5/xx unknown
-
1976
- 1976-01-16 BR BR7600251A patent/BR7600251A/pt unknown
- 1976-01-27 TR TR18730A patent/TR18730A/xx unknown
- 1976-01-29 GB GB3648/76A patent/GB1511412A/en not_active Expired
- 1976-01-29 SU SU762317700A patent/SU625598A3/ru active
- 1976-01-30 BE BE163933A patent/BE838080A/xx unknown
- 1976-01-30 FR FR7602570A patent/FR2299310A1/fr active Granted
- 1976-01-30 NL NL7600984A patent/NL7600984A/xx not_active Application Discontinuation
- 1976-01-30 IT IT7647875A patent/IT1053475B/it active
- 1976-01-31 PL PL1976186951A patent/PL103014B1/pl unknown
- 1976-01-31 RO RO7684665A patent/RO69845A/ro unknown
- 1976-02-02 CA CA245,053A patent/CA1081245A/en not_active Expired
- 1976-02-02 JP JP51010222A patent/JPS51101946A/ja active Pending
- 1976-02-13 IN IN262/CAL/1976A patent/IN145144B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7600984A (nl) | 1976-08-03 |
| RO69845A (ro) | 1981-07-30 |
| GB1511412A (en) | 1978-05-17 |
| FR2299310A1 (fr) | 1976-08-27 |
| IN145144B (OSRAM) | 1978-09-02 |
| FR2299310B1 (OSRAM) | 1979-05-18 |
| BE838080A (fr) | 1976-05-14 |
| DD123738A5 (OSRAM) | 1977-01-12 |
| IT1053475B (it) | 1981-08-31 |
| SU625598A3 (ru) | 1978-09-25 |
| BR7600251A (pt) | 1976-08-31 |
| TR18730A (tr) | 1977-07-27 |
| PL103014B1 (pl) | 1979-05-31 |
| DE2504156A1 (de) | 1976-08-05 |
| MX3016E (es) | 1980-02-04 |
| JPS51101946A (en) | 1976-09-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |