CA1038996A - Continuous manufacture of linear polyesters - Google Patents
Continuous manufacture of linear polyestersInfo
- Publication number
- CA1038996A CA1038996A CA237,205A CA237205A CA1038996A CA 1038996 A CA1038996 A CA 1038996A CA 237205 A CA237205 A CA 237205A CA 1038996 A CA1038996 A CA 1038996A
- Authority
- CA
- Canada
- Prior art keywords
- terephthalic acid
- esterification
- glycols
- weight
- 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
- 229920000728 polyester Polymers 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000002334 glycols Chemical class 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 6
- -1 terephthalic acid glycol esters Chemical class 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 239000011541 reaction mixture Substances 0.000 claims abstract description 3
- 230000032050 esterification Effects 0.000 claims abstract 9
- 238000005886 esterification reaction Methods 0.000 claims abstract 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims 1
- 239000000292 calcium oxide Substances 0.000 claims 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims 1
- AAEHPKIXIIACPQ-UHFFFAOYSA-L calcium;terephthalate Chemical compound [Ca+2].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 AAEHPKIXIIACPQ-UHFFFAOYSA-L 0.000 claims 1
- VIQSRHWJEKERKR-UHFFFAOYSA-L disodium;terephthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 VIQSRHWJEKERKR-UHFFFAOYSA-L 0.000 claims 1
- 150000002290 germanium Chemical class 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- 241000905957 Channa melasoma Species 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
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 235000002908 manganese Nutrition 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002311 subsequent effect Effects 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
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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742449162 DE2449162A1 (de) | 1974-10-16 | 1974-10-16 | Verfahren zur kontinuierlichen herstellung von linearen polyestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1038996A true CA1038996A (en) | 1978-09-19 |
Family
ID=5928397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA237,205A Expired CA1038996A (en) | 1974-10-16 | 1975-10-07 | Continuous manufacture of linear polyesters |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4039515A (enExample) |
| JP (1) | JPS5164595A (enExample) |
| BE (1) | BE833863A (enExample) |
| CA (1) | CA1038996A (enExample) |
| DE (1) | DE2449162A1 (enExample) |
| DK (1) | DK464175A (enExample) |
| FR (1) | FR2288117A1 (enExample) |
| GB (1) | GB1514275A (enExample) |
| IE (1) | IE42166B1 (enExample) |
| IT (1) | IT1042568B (enExample) |
| LU (1) | LU73584A1 (enExample) |
| NL (1) | NL7512020A (enExample) |
| SE (1) | SE415263B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54135894A (en) * | 1978-04-13 | 1979-10-22 | Toray Ind Inc | Batch-wise esterification |
| US4440924A (en) * | 1982-10-05 | 1984-04-03 | Toyo Boseki Kabushiki Kaisha | Process for production of polyester |
| US4435562A (en) | 1983-05-06 | 1984-03-06 | The Goodyear Tire & Rubber Company | Process for the production of polyester copolymers |
| US5162557A (en) * | 1988-07-27 | 1992-11-10 | Synthetic Products Company | Ruthenium aromatic polycarboxylates |
| US5026888A (en) * | 1988-07-27 | 1991-06-25 | Synthetic Products Company | Ruthenium terephthalate |
| US4963127A (en) * | 1988-07-27 | 1990-10-16 | Synthetic Products Company | Stannic terephthalate |
| AU2077601A (en) | 1999-12-10 | 2001-06-18 | Dow Global Technologies Inc. | Catalyst systems for polycondensation reactions |
| US6906164B2 (en) | 2000-12-07 | 2005-06-14 | Eastman Chemical Company | Polyester process using a pipe reactor |
| US6649263B2 (en) | 2001-11-16 | 2003-11-18 | Honeywell International Inc. | Polyester resin and industrial yarn process |
| WO2004014982A2 (en) | 2002-05-09 | 2004-02-19 | Equipolymers Gmbh | Catalyst systems for polycondensation reactions |
| US7943094B2 (en) | 2006-12-07 | 2011-05-17 | Grupo Petrotemex, S.A. De C.V. | Polyester production system employing horizontally elongated esterification vessel |
| US7649109B2 (en) | 2006-12-07 | 2010-01-19 | Eastman Chemical Company | Polyester production system employing recirculation of hot alcohol to esterification zone |
| US7863477B2 (en) | 2007-03-08 | 2011-01-04 | Eastman Chemical Company | Polyester production system employing hot paste to esterification zone |
| US7892498B2 (en) * | 2007-03-08 | 2011-02-22 | Eastman Chemical Company | Polyester production system employing an unagitated esterification reactor |
| US7868130B2 (en) | 2007-07-12 | 2011-01-11 | Eastman Chemical Company | Multi-level tubular reactor with vertically spaced segments |
| US7872089B2 (en) * | 2007-07-12 | 2011-01-18 | Eastman Chemical Company | Multi-level tubular reactor with internal tray |
| US7858730B2 (en) | 2007-07-12 | 2010-12-28 | Eastman Chemical Company | Multi-level tubular reactor with dual headers |
| US7872090B2 (en) | 2007-07-12 | 2011-01-18 | Eastman Chemical Company | Reactor system with optimized heating and phase separation |
| US7847053B2 (en) | 2007-07-12 | 2010-12-07 | Eastman Chemical Company | Multi-level tubular reactor with oppositely extending segments |
| US7829653B2 (en) | 2007-07-12 | 2010-11-09 | Eastman Chemical Company | Horizontal trayed reactor |
| US7868129B2 (en) | 2007-07-12 | 2011-01-11 | Eastman Chemical Company | Sloped tubular reactor with spaced sequential trays |
| US7842777B2 (en) | 2007-07-12 | 2010-11-30 | Eastman Chemical Company | Sloped tubular reactor with divided flow |
| CN114395114A (zh) * | 2022-01-19 | 2022-04-26 | 江苏双江能源科技股份有限公司 | 一种混合酯可降解绝缘材料及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2793235A (en) * | 1954-09-27 | 1957-05-21 | Du Pont | Recovery of glycols from polyester production |
| NL89785C (enExample) * | 1955-02-09 | |||
| GB990642A (en) * | 1961-02-10 | 1965-04-28 | Toyo Rayon Co Ltd | Method of preparing polyesters |
| CH435736A (de) * | 1964-03-19 | 1967-05-15 | Schwarza Chemiefaser | Verfahren zur kurzfristigen Herstellung von linearen Polyestern bzw. Mischpolyestern |
| LU48718A1 (enExample) * | 1964-06-01 | 1965-12-01 | ||
| DE1545167A1 (de) * | 1964-07-09 | 1969-06-26 | Schwarza Chemiefaser | Verfahren zur Herstellung von linearen Polyestern bzw. Mischpolyestern |
| FR1446317A (fr) * | 1965-02-12 | 1966-07-22 | Chemiefaserwerk Schwarza Veb | Procédé de fabrication rapide de polyesters et de polyesters mixtes linéaires, notamment de téréphtalate de polyéthylène glycol |
| US3444140A (en) * | 1966-11-14 | 1969-05-13 | Fmc Corp | Pressurized esterification of terephthalic acid in presence of low concentration of tertiary amine |
| US3590072A (en) * | 1966-11-18 | 1971-06-29 | Monsanto Co | Method for direct esterification of terephthalic acid with ethylene glycol |
| NL6717446A (enExample) * | 1966-12-30 | 1968-07-01 |
-
1974
- 1974-10-16 DE DE19742449162 patent/DE2449162A1/de not_active Withdrawn
-
1975
- 1975-09-15 IT IT27258/75A patent/IT1042568B/it active
- 1975-09-26 BE BE160407A patent/BE833863A/xx unknown
- 1975-10-06 US US05/619,812 patent/US4039515A/en not_active Expired - Lifetime
- 1975-10-07 CA CA237,205A patent/CA1038996A/en not_active Expired
- 1975-10-10 GB GB41585/75A patent/GB1514275A/en not_active Expired
- 1975-10-13 IE IE2224/75A patent/IE42166B1/en unknown
- 1975-10-13 NL NL7512020A patent/NL7512020A/xx not_active Application Discontinuation
- 1975-10-14 FR FR7531418A patent/FR2288117A1/fr active Granted
- 1975-10-14 SE SE7511490A patent/SE415263B/xx unknown
- 1975-10-14 LU LU73584A patent/LU73584A1/xx unknown
- 1975-10-14 JP JP50122963A patent/JPS5164595A/ja active Pending
- 1975-10-15 DK DK464175A patent/DK464175A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2288117B1 (enExample) | 1979-03-23 |
| DE2449162A1 (de) | 1976-04-22 |
| IE42166B1 (en) | 1980-06-18 |
| LU73584A1 (enExample) | 1976-06-11 |
| NL7512020A (nl) | 1976-04-21 |
| SE7511490L (sv) | 1976-04-20 |
| IT1042568B (it) | 1980-01-30 |
| SE415263B (sv) | 1980-09-22 |
| BE833863A (fr) | 1976-03-26 |
| DK464175A (da) | 1976-04-17 |
| JPS5164595A (enExample) | 1976-06-04 |
| IE42166L (en) | 1976-04-16 |
| FR2288117A1 (fr) | 1976-05-14 |
| US4039515A (en) | 1977-08-02 |
| GB1514275A (en) | 1978-06-14 |
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