DE2224869C3 - Verfahren zur Herstellung von Dimethylterephthalat - Google Patents
Verfahren zur Herstellung von DimethylterephthalatInfo
- Publication number
- DE2224869C3 DE2224869C3 DE2224869A DE2224869A DE2224869C3 DE 2224869 C3 DE2224869 C3 DE 2224869C3 DE 2224869 A DE2224869 A DE 2224869A DE 2224869 A DE2224869 A DE 2224869A DE 2224869 C3 DE2224869 C3 DE 2224869C3
- Authority
- DE
- Germany
- Prior art keywords
- terephthalic acid
- methanol
- esterification
- dimethyl terephthalate
- prereactor
- 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
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 147
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 140
- 239000003054 catalyst Substances 0.000 claims description 31
- 230000032050 esterification Effects 0.000 claims description 29
- 238000005886 esterification reaction Methods 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000001704 evaporation Methods 0.000 claims description 9
- 230000008020 evaporation Effects 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- REIDAMBAPLIATC-UHFFFAOYSA-M 4-methoxycarbonylbenzoate Chemical compound COC(=O)C1=CC=C(C([O-])=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-M 0.000 claims description 6
- 239000007789 gas Substances 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 238000010626 work up procedure Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 238000013021 overheating Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012495 reaction gas Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Chemical class 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- -1 Use oxides Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- RSECMQCYQHGSFP-UHFFFAOYSA-N methanol;terephthalic acid Chemical compound OC.OC(=O)C1=CC=C(C(O)=O)C=C1 RSECMQCYQHGSFP-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/28—Moving reactors, e.g. rotary drums
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00168—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles
- B01J2208/00247—Reflux columns
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00265—Part of all of the reactants being heated or cooled outside the reactor while recycling
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00548—Flow
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/18—Details relating to the spatial orientation of the reactor
- B01J2219/182—Details relating to the spatial orientation of the reactor horizontal
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2224869A DE2224869C3 (de) | 1972-05-20 | 1972-05-20 | Verfahren zur Herstellung von Dimethylterephthalat |
| FR7316876A FR2185613B1 (enExample) | 1972-05-20 | 1973-05-10 | |
| NL7307011A NL7307011A (enExample) | 1972-05-20 | 1973-05-18 | |
| GB2372373A GB1425375A (en) | 1972-05-20 | 1973-05-18 | Process for the esterification of terephthalic acid |
| US05/361,597 US3940431A (en) | 1972-05-20 | 1973-05-18 | Dimethyl terephthalate prepared by the esterification of terephthalic acid |
| IT50077/73A IT985095B (it) | 1972-05-20 | 1973-05-18 | Procedimento ed impianto per esterificare acido tereftalico |
| BE131323A BE799780A (fr) | 1972-05-20 | 1973-05-18 | Procede d'esterification de l'acide terephtalique, |
| JP48056646A JPS4948633A (enExample) | 1972-05-20 | 1973-05-21 | |
| US05/616,029 US3980441A (en) | 1972-05-20 | 1975-09-23 | Apparatus for the production of dimethyl terephthalate by the esterification of terephthalic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2224869A DE2224869C3 (de) | 1972-05-20 | 1972-05-20 | Verfahren zur Herstellung von Dimethylterephthalat |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2224869A1 DE2224869A1 (de) | 1973-12-13 |
| DE2224869B2 DE2224869B2 (de) | 1975-04-24 |
| DE2224869C3 true DE2224869C3 (de) | 1975-12-11 |
Family
ID=5845543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2224869A Expired DE2224869C3 (de) | 1972-05-20 | 1972-05-20 | Verfahren zur Herstellung von Dimethylterephthalat |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3940431A (enExample) |
| JP (1) | JPS4948633A (enExample) |
| BE (1) | BE799780A (enExample) |
| DE (1) | DE2224869C3 (enExample) |
| FR (1) | FR2185613B1 (enExample) |
| GB (1) | GB1425375A (enExample) |
| IT (1) | IT985095B (enExample) |
| NL (1) | NL7307011A (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3907709A (en) * | 1972-09-02 | 1975-09-23 | Huels Chemische Werke Ag | Esterification catalysts |
| US4365078A (en) * | 1977-12-16 | 1982-12-21 | The Goodyear Tire & Rubber Company | Process for charging dry terephthalic acid into a reactor |
| US6245727B1 (en) | 1989-03-20 | 2001-06-12 | Henkel Kommanditgesellschaft Auf Aktien | Discontinuous process for conducting a heterogeneously catalyzed reaction and installation for heterogeneously catalyzed manufacture of products |
| DE3909128A1 (de) * | 1989-03-20 | 1990-09-27 | Henkel Kgaa | Diskontinuierliches verfahren zum fuehren einer heterogen katalysierten reaktion und anlage zum heterogen katalysierten herstellen von produkten |
| US8367859B2 (en) | 2009-06-16 | 2013-02-05 | Amyris, Inc. | Cyclohexane 1,4 carboxylates |
| WO2010148081A2 (en) | 2009-06-16 | 2010-12-23 | Draths Corporation | Novel terephthalic and trimellitic based acids and carboxylate derivatives thereof |
| WO2010148070A2 (en) | 2009-06-16 | 2010-12-23 | Draths Corporation | Biobased polyesters |
| US8426639B2 (en) * | 2009-06-16 | 2013-04-23 | Amyris, Inc. | Preparation of trans, trans muconic acid and trans, trans muconates |
| MX2012007944A (es) | 2010-01-08 | 2012-08-15 | Amyris Inc | Metodos para producir isomeros de acido muconico y sales de muconato. |
| US20170001946A1 (en) * | 2015-07-02 | 2017-01-05 | Sadesh Sookraj | Terephthalate derivatives and compositions thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1088474B (de) * | 1958-11-17 | 1960-09-08 | Bergwerksverband Gmbh | Verfahren zur Veresterung von Terephthalsaeure |
| NL282032A (enExample) * | 1961-08-17 | |||
| DE1212063B (de) * | 1964-04-20 | 1966-03-10 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Dimethylterephthalat |
| FR1496079A (fr) * | 1965-03-11 | 1967-09-29 | Mobil Oil Corp | Procédé perfectionné d'estérification |
| US3377376A (en) * | 1966-02-07 | 1968-04-09 | Mobil Oil Corp | Vapor phase esterification of terephthalic acid in the presence of alkali metal impregnated catalyst |
| US3617226A (en) * | 1968-04-26 | 1971-11-02 | Huels Chemische Werke Ag | Apparatus for the continuous preparation of esters |
| 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 |
-
1972
- 1972-05-20 DE DE2224869A patent/DE2224869C3/de not_active Expired
-
1973
- 1973-05-10 FR FR7316876A patent/FR2185613B1/fr not_active Expired
- 1973-05-18 BE BE131323A patent/BE799780A/xx unknown
- 1973-05-18 US US05/361,597 patent/US3940431A/en not_active Expired - Lifetime
- 1973-05-18 NL NL7307011A patent/NL7307011A/xx not_active Application Discontinuation
- 1973-05-18 IT IT50077/73A patent/IT985095B/it active
- 1973-05-18 GB GB2372373A patent/GB1425375A/en not_active Expired
- 1973-05-21 JP JP48056646A patent/JPS4948633A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2224869A1 (de) | 1973-12-13 |
| IT985095B (it) | 1974-11-30 |
| US3940431A (en) | 1976-02-24 |
| BE799780A (fr) | 1973-09-17 |
| FR2185613B1 (enExample) | 1977-04-29 |
| DE2224869B2 (de) | 1975-04-24 |
| JPS4948633A (enExample) | 1974-05-11 |
| GB1425375A (en) | 1976-02-18 |
| FR2185613A1 (enExample) | 1974-01-04 |
| NL7307011A (enExample) | 1973-11-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |