DE1593309B1 - Verfahren zur kontinuierlichen Herstellung von Benzoldicarbonsaeure-bis-glycolestern - Google Patents
Verfahren zur kontinuierlichen Herstellung von Benzoldicarbonsaeure-bis-glycolesternInfo
- Publication number
- DE1593309B1 DE1593309B1 DE19661593309 DE1593309A DE1593309B1 DE 1593309 B1 DE1593309 B1 DE 1593309B1 DE 19661593309 DE19661593309 DE 19661593309 DE 1593309 A DE1593309 A DE 1593309A DE 1593309 B1 DE1593309 B1 DE 1593309B1
- Authority
- DE
- Germany
- Prior art keywords
- transesterification
- reaction
- bis
- dicarboxylic acid
- reaction vessel
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 8
- 238000010924 continuous production Methods 0.000 title claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 61
- 238000005809 transesterification reaction Methods 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 150000002334 glycols Chemical class 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 63
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 8
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 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
- 229960005147 calcium acetate Drugs 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- 239000001639 calcium acetate Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- -1 Ethylene- Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
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 |
|---|---|---|---|
| FR20074A FR1449727A (fr) | 1965-06-09 | 1965-06-09 | Préparation en continu d'esters phtaliques de glycols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1593309B1 true DE1593309B1 (de) | 1970-08-20 |
Family
ID=8581324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593309 Withdrawn DE1593309B1 (de) | 1965-06-09 | 1966-06-08 | Verfahren zur kontinuierlichen Herstellung von Benzoldicarbonsaeure-bis-glycolestern |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3507905A (OSRAM) |
| BE (1) | BE682284A (OSRAM) |
| CH (1) | CH454827A (OSRAM) |
| DE (1) | DE1593309B1 (OSRAM) |
| ES (1) | ES327703A1 (OSRAM) |
| FR (1) | FR1449727A (OSRAM) |
| GB (1) | GB1115593A (OSRAM) |
| LU (1) | LU51273A1 (OSRAM) |
| NL (2) | NL6607676A (OSRAM) |
| SE (1) | SE346535B (OSRAM) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3676485A (en) * | 1968-08-12 | 1972-07-11 | Eastman Kodak Co | Method for use in a continuous flow reaction for producing a monomer and or a protopolymer |
| DE2504258A1 (de) * | 1975-02-01 | 1976-08-05 | Dynamit Nobel Ag | Verfahren und apparatur zur herstellung von oligomeren alkylenterephthalaten |
| US6906164B2 (en) * | 2000-12-07 | 2005-06-14 | Eastman Chemical Company | Polyester process using a pipe reactor |
| CN1900139B (zh) * | 2000-12-07 | 2012-11-14 | 奇派特石化有限公司 | 制造缩聚物的方法 |
| US7074879B2 (en) * | 2003-06-06 | 2006-07-11 | Eastman Chemical Company | Polyester process using a pipe reactor |
| US7135541B2 (en) | 2003-06-06 | 2006-11-14 | Eastman Chemical Company | Polyester process using a pipe reactor |
| US7332548B2 (en) * | 2004-03-04 | 2008-02-19 | Eastman Chemical Company | Process for production of a polyester product from alkylene oxide and carboxylic acid |
| US20080139780A1 (en) * | 2006-12-07 | 2008-06-12 | Debruin Bruce Roger | Polyester production system employing short residence time esterification |
| 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 |
| US7842777B2 (en) * | 2007-07-12 | 2010-11-30 | Eastman Chemical Company | Sloped tubular reactor with divided flow |
| US7868129B2 (en) * | 2007-07-12 | 2011-01-11 | Eastman Chemical Company | Sloped tubular reactor with spaced sequential trays |
| US7868130B2 (en) * | 2007-07-12 | 2011-01-11 | Eastman Chemical Company | Multi-level tubular reactor with vertically spaced segments |
| 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 |
| 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 |
| US7829653B2 (en) * | 2007-07-12 | 2010-11-09 | Eastman Chemical Company | Horizontal trayed reactor |
| CN108976116B (zh) * | 2017-06-02 | 2021-02-02 | 中国科学院大连化学物理研究所 | 一种钛螯合物催化酯交换制备邻苯二甲酸高碳醇酯的方法 |
| CN108976117B (zh) * | 2017-06-02 | 2021-01-26 | 中国科学院大连化学物理研究所 | 一种酯交换连续反应制备邻苯二甲酸高碳醇酯的方法 |
| CN113617311A (zh) * | 2021-09-10 | 2021-11-09 | 中国科学院电工研究所 | 一种电热催化反应器 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE977308C (de) * | 1952-11-26 | 1965-12-02 | Du Pont | Verfahren zur kontinuierlichen Umesterung von Estern leicht fluechtiger Alkohole |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2829153A (en) * | 1957-03-04 | 1958-04-01 | Du Pont | Continuous ester interchange process |
| NL294427A (OSRAM) * | 1962-06-23 | |||
| BE633878A (OSRAM) * | 1963-06-20 |
-
0
- NL NL131998D patent/NL131998C/xx active
-
1965
- 1965-06-09 FR FR20074A patent/FR1449727A/fr not_active Expired
-
1966
- 1966-06-02 NL NL6607676A patent/NL6607676A/xx unknown
- 1966-06-03 US US555208A patent/US3507905A/en not_active Expired - Lifetime
- 1966-06-08 LU LU51273A patent/LU51273A1/xx unknown
- 1966-06-08 ES ES0327703A patent/ES327703A1/es not_active Expired
- 1966-06-08 BE BE682284D patent/BE682284A/xx unknown
- 1966-06-08 DE DE19661593309 patent/DE1593309B1/de not_active Withdrawn
- 1966-06-08 SE SE07860/66A patent/SE346535B/xx unknown
- 1966-06-09 CH CH833166A patent/CH454827A/fr unknown
- 1966-06-09 GB GB25784/66A patent/GB1115593A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE977308C (de) * | 1952-11-26 | 1965-12-02 | Du Pont | Verfahren zur kontinuierlichen Umesterung von Estern leicht fluechtiger Alkohole |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1449727A (fr) | 1966-05-06 |
| NL131998C (OSRAM) | |
| NL6607676A (OSRAM) | 1966-12-12 |
| BE682284A (OSRAM) | 1966-12-08 |
| GB1115593A (en) | 1968-05-29 |
| LU51273A1 (OSRAM) | 1966-08-08 |
| ES327703A1 (es) | 1967-03-16 |
| SE346535B (OSRAM) | 1972-07-10 |
| CH454827A (fr) | 1968-04-30 |
| US3507905A (en) | 1970-04-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |