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 polymers

Info

Publication number: CA1081245A
Authority: CA; Canada
Prior art keywords: product; glycol; ester; weight; ethylene glycol
Prior art date: 1975-02-01
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

Application number

CA245,053A

Other languages

English (en)

French (fr)

Inventor

Reinhard Schmidt

Rudolf Burkhardt

Gustav Renckhoff

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dynamit Nobel AG

Original Assignee

Dynamit Nobel AG

Priority date (The priority date 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 date listed.)

1975-02-01

Filing date

1976-02-02

Publication date

1980-07-08

1976-02-02 Application filed by Dynamit Nobel AG filed Critical Dynamit Nobel AG

1980-07-08 Application granted granted Critical

1980-07-08 Publication of CA1081245A publication Critical patent/CA1081245A/en

Status Expired legal-status Critical Current

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)

CA245,053A 1975-02-01 1976-02-02 Terephthalic acid ethylene glycol esters, their production and use in the production of polyester polymers Expired CA1081245A (en)

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 (ro)
BE (1)	BE838080A (ro)
BR (1)	BR7600251A (ro)
CA (1)	CA1081245A (ro)
DD (1)	DD123738A5 (ro)
DE (1)	DE2504156A1 (ro)
FR (1)	FR2299310A1 (ro)
GB (1)	GB1511412A (ro)
IN (1)	IN145144B (ro)
IT (1)	IT1053475B (ro)
MX (1)	MX3016E (ro)
NL (1)	NL7600984A (ro)
PL (1)	PL103014B1 (ro)
RO (1)	RO69845A (ro)
SU (1)	SU625598A3 (ro)
TR (1)	TR18730A (ro)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3590385T1 (de) *	1984-08-14	1986-08-28	Mitsubishi Chemical Industries Ltd., Tokio/Tokyo	Verfahren zur Herstellung von Tetramethylbiphenyltetracarboxylat
US6630601B1 (en) *	1999-08-04	2003-10-07	Aies Company Limited	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 SU SU762317700A patent/SU625598A3/ru active
- 1976-01-29 GB GB3648/76A patent/GB1511412A/en not_active Expired
- 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 BE BE163933A patent/BE838080A/xx unknown
- 1976-01-30 IT IT7647875A patent/IT1053475B/it active
- 1976-01-31 RO RO7684665A patent/RO69845A/ro unknown
- 1976-01-31 PL PL1976186951A patent/PL103014B1/pl unknown
- 1976-02-02 JP JP51010222A patent/JPS51101946A/ja active Pending
- 1976-02-02 CA CA245,053A patent/CA1081245A/en not_active Expired
- 1976-02-13 IN IN262/CAL/1976A patent/IN145144B/en unknown

Also Published As

Publication number	Publication date
SU625598A3 (ru)	1978-09-25
DE2504156A1 (de)	1976-08-05
TR18730A (tr)	1977-07-27
DD123738A5 (ro)	1977-01-12
IT1053475B (it)	1981-08-31
FR2299310B1 (ro)	1979-05-18
RO69845A (ro)	1981-07-30
BR7600251A (pt)	1976-08-31
FR2299310A1 (fr)	1976-08-27
MX3016E (es)	1980-02-04
JPS51101946A (en)	1976-09-08
PL103014B1 (pl)	1979-05-31
GB1511412A (en)	1978-05-17
IN145144B (ro)	1978-09-02
BE838080A (fr)	1976-05-14
NL7600984A (nl)	1976-08-03

Legal Events

Date	Code	Title	Description
1997-07-08	MKEX	Expiry

Publication	Publication Date	Title
KR0173322B1 (ko)	1999-04-01	폴리(부틸렌 테레프탈레이트) 올리고머 또는 폴리(부틸렌 이소프탈레이트) 올리고머를 제조하기 위한 연속법
CA2389800C (en)	2011-12-06	Continuous process for the preparation of polytrimethylene ether glycol
US3050533A (en)	1962-08-21	Manufacture of esters
US5786443A (en)	1998-07-28	Process of making polyester prepolymer
US3723391A (en)	1973-03-27	Continuous manufacture of polyesters
KR102426474B1 (ko)	2022-07-27	생분해성 폴리에스테르를 제조하기 위한 방법 및 장치
PL101877B1 (pl)	1979-02-28	A method of producing oligomeric alkylene terephtalates as well as a device for producing oligomeric alkylene terephthalates
RU2486172C2 (ru)	2013-06-27	Способ получения аллилметакрилата
US4499261A (en)	1985-02-12	Process for the continuous production of polybutylene terephthalate of high molecular weight
NO158309B (no)	1988-05-09	Vindturbin med svingetrimming.
US6887953B2 (en)	2005-05-03	Esterification process
US6812321B1 (en)	2004-11-02	Method for the continuous production of polybutyleneterephthalate from terephthalic acid and butanediol
US6657040B1 (en)	2003-12-02	Method for the continuous production of polybutylene terephthalate from terephthal acid and butane diole
CN112062678A (zh)	2020-12-11	一种丙烯酸叔丁酯生产过程中防止聚合的方法
NO117944B (ro)	1969-10-13
JPH0314535A (ja)	1991-01-23	α置換シンナムアルデヒドを製造する方法、前記製造法により得られるアミル又はヘキシルシンナムアルデヒド及び前記アミル又はヘキシルシンナムアルデヒドを含有する香料基剤
US9527953B2 (en)	2016-12-27	Continuous preparation for polyester
US4180635A (en)	1979-12-25	Continuous manufacture of unsaturated polyesters
CN100362041C (zh)	2008-01-16	四氢呋喃共聚物的制备
Bratić et al.	2025	5-Ethylidene-2-norbornene (ENB) and 5-vinyl-2-norbornene (VNB) based alicyclic polyols for the synthesis of polyesters
KR102814491B1 (ko)	2025-05-29	폴리에틸렌 테레프탈레이트의 해중합에서 분리벽형 증류탑을 이용한 에틸렌글라이콜의 회수방법
RU2854972C2 (ru)	2026-01-22	Реакторы и их специальная конструкция, подходящие для установки получения поликарбоната, обладающей высокой эксплуатационной гибкостью и надёжностью, в частности, с использованием технологии предварительной переэтерификации
US3491143A (en)	1970-01-20	Esterification process
SU625598A3 (ru)	1978-09-25	Способ выделени олигомерного этилентерефталата
KR102847514B1 (ko)	2025-08-20	우레탄 기를 함유하는 폴리이소시아네이트를 제조하는 방법