DE2407155A1 - Herstellung von polyestern - Google Patents
Herstellung von polyesternInfo
- Publication number
- DE2407155A1 DE2407155A1 DE19742407155 DE2407155A DE2407155A1 DE 2407155 A1 DE2407155 A1 DE 2407155A1 DE 19742407155 DE19742407155 DE 19742407155 DE 2407155 A DE2407155 A DE 2407155A DE 2407155 A1 DE2407155 A1 DE 2407155A1
- Authority
- DE
- Germany
- Prior art keywords
- butanediol
- terephthalic acid
- mixture
- mol
- poly
- 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- Withdrawn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
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 229920000728 polyester Polymers 0.000 title description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 74
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 10
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 claims description 8
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical group [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 16
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 14
- 150000002009 diols Chemical class 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- -1 poly (alkylene terephthalates Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 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 2
- IHEDBVUTTQXGSJ-UHFFFAOYSA-M 2-[bis(2-oxidoethyl)amino]ethanolate;titanium(4+);hydroxide Chemical compound [OH-].[Ti+4].[O-]CCN(CC[O-])CC[O-] IHEDBVUTTQXGSJ-UHFFFAOYSA-M 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001463 antimony compounds Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 239000012262 resinous product Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- SFHBJXIEBWOOFA-UHFFFAOYSA-N 5-methyl-3,6-dioxabicyclo[6.2.2]dodeca-1(10),8,11-triene-2,7-dione Chemical compound O=C1OC(C)COC(=O)C2=CC=C1C=C2 SFHBJXIEBWOOFA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000009757 thermoplastic moulding Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 239000002023 wood 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33544173A | 1973-02-26 | 1973-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2407155A1 true DE2407155A1 (de) | 1974-08-29 |
Family
ID=23311789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742407155 Withdrawn DE2407155A1 (de) | 1973-02-26 | 1974-02-15 | Herstellung von polyestern |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5024389A (enrdf_load_stackoverflow) |
| DE (1) | DE2407155A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2219186B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1438250A (enrdf_load_stackoverflow) |
| IT (1) | IT1007610B (enrdf_load_stackoverflow) |
| NL (1) | NL7402560A (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2539249A1 (de) * | 1974-09-03 | 1976-03-11 | Mitsubishi Chem Ind | Verfahren zur herstellung eines polyesters |
| DE2621099A1 (de) * | 1975-05-12 | 1976-11-25 | Standard Oil Co | Verfahren zur herstellung von polybutylenterephthalat |
| EP0953796A1 (de) | 1998-04-30 | 1999-11-03 | Ems-Inventa Ag | Antistatische und peroxidstabile Formmassen |
| US6680093B1 (en) | 1997-05-15 | 2004-01-20 | Degussa Ag | Multilayer composites |
| EP2489494A1 (de) | 2011-02-17 | 2012-08-22 | Evonik Degussa GmbH | Verfahren zur Herstellung von Stäben und ihre Verwendung als Implantate |
| EP2581947A1 (de) | 2011-10-14 | 2013-04-17 | Evonik Industries AG | Verwendung einer Mehrschichtfolie mit Polyamid- und Polyesterschichten für die Herstellung photovoltaischer Module |
| EP2581222A1 (de) | 2011-10-14 | 2013-04-17 | Evonik Industries AG | Verwendung einer Mehrschichtfolie mit Sauerstoffpermeationssperre für die Herstellung photovoltaischer Module |
| CN113201805A (zh) * | 2021-03-30 | 2021-08-03 | 新疆蓝山屯河化工股份有限公司 | 一种pbat纤维的制备方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140018468A (ko) * | 2012-07-30 | 2014-02-13 | 삼성정밀화학 주식회사 | 방향족 디카르복실산 화합물의 분할 투입에 의한 생분해성 폴리에스테르 공중합체의 제조방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE545091A (enrdf_load_stackoverflow) * | 1955-02-09 |
-
1974
- 1974-02-15 DE DE19742407155 patent/DE2407155A1/de not_active Withdrawn
- 1974-02-20 JP JP1957174A patent/JPS5024389A/ja active Pending
- 1974-02-25 NL NL7402560A patent/NL7402560A/xx not_active Application Discontinuation
- 1974-02-25 GB GB835674A patent/GB1438250A/en not_active Expired
- 1974-02-26 FR FR7406494A patent/FR2219186B1/fr not_active Expired
- 1974-04-08 IT IT2051874A patent/IT1007610B/it active
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2539249A1 (de) * | 1974-09-03 | 1976-03-11 | Mitsubishi Chem Ind | Verfahren zur herstellung eines polyesters |
| DE2621099A1 (de) * | 1975-05-12 | 1976-11-25 | Standard Oil Co | Verfahren zur herstellung von polybutylenterephthalat |
| US6680093B1 (en) | 1997-05-15 | 2004-01-20 | Degussa Ag | Multilayer composites |
| EP0953796A1 (de) | 1998-04-30 | 1999-11-03 | Ems-Inventa Ag | Antistatische und peroxidstabile Formmassen |
| US6469092B1 (en) | 1998-04-30 | 2002-10-22 | Ens-Inventa Ag | Anti-static and peroxide-stable molding compounds |
| USRE39207E1 (en) | 1998-04-30 | 2006-07-25 | Ems-Inventa Ag | Anti-static and peroxide-stable molding compounds |
| EP2489494A1 (de) | 2011-02-17 | 2012-08-22 | Evonik Degussa GmbH | Verfahren zur Herstellung von Stäben und ihre Verwendung als Implantate |
| EP2581947A1 (de) | 2011-10-14 | 2013-04-17 | Evonik Industries AG | Verwendung einer Mehrschichtfolie mit Polyamid- und Polyesterschichten für die Herstellung photovoltaischer Module |
| EP2581222A1 (de) | 2011-10-14 | 2013-04-17 | Evonik Industries AG | Verwendung einer Mehrschichtfolie mit Sauerstoffpermeationssperre für die Herstellung photovoltaischer Module |
| DE102011084518A1 (de) | 2011-10-14 | 2013-04-18 | Evonik Industries Ag | Verwendung einer Mehrschichtfolie mit Polyamid- und Polyesterschichten fürdie Herstellung photovoltaischer Module |
| DE102011084523A1 (de) | 2011-10-14 | 2013-04-18 | Evonik Industries Ag | Verwendung einer Mehrschichtfolie mit Sauerstoffpermeationssperre für die Herstellung photovoltaischer Module |
| CN113201805A (zh) * | 2021-03-30 | 2021-08-03 | 新疆蓝山屯河化工股份有限公司 | 一种pbat纤维的制备方法 |
| CN113201805B (zh) * | 2021-03-30 | 2022-07-15 | 新疆蓝山屯河科技股份有限公司 | 一种pbat纤维的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1007610B (it) | 1976-10-30 |
| FR2219186A1 (enrdf_load_stackoverflow) | 1974-09-20 |
| NL7402560A (enrdf_load_stackoverflow) | 1974-08-28 |
| GB1438250A (en) | 1976-06-03 |
| JPS5024389A (enrdf_load_stackoverflow) | 1975-03-15 |
| FR2219186B1 (enrdf_load_stackoverflow) | 1979-07-27 |
| AU6586074A (en) | 1975-08-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee | ||
| 8141 | Disposal/no request for examination |