CS251094B2 - Method of terephthalic acid's dimethyl ester production - Google Patents
Method of terephthalic acid's dimethyl ester production Download PDFInfo
- Publication number
- CS251094B2 CS251094B2 CS851507A CS150785A CS251094B2 CS 251094 B2 CS251094 B2 CS 251094B2 CS 851507 A CS851507 A CS 851507A CS 150785 A CS150785 A CS 150785A CS 251094 B2 CS251094 B2 CS 251094B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methanol
- fraction
- mpa
- esterification
- pressure
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims 4
- 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 title claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 249
- 238000005886 esterification reaction Methods 0.000 claims description 46
- 230000032050 esterification Effects 0.000 claims description 45
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 22
- 230000003647 oxidation Effects 0.000 claims description 21
- 238000007254 oxidation reaction Methods 0.000 claims description 21
- 238000001704 evaporation Methods 0.000 claims description 15
- 230000008020 evaporation Effects 0.000 claims description 13
- 238000001953 recrystallisation Methods 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000706 filtrate Substances 0.000 claims description 10
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- -1 methyl p-toluyl Chemical group 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 7
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 6
- REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 claims description 4
- RYRZSXJVEILFRR-UHFFFAOYSA-N 2,3-dimethylterephthalic acid Chemical compound CC1=C(C)C(C(O)=O)=CC=C1C(O)=O RYRZSXJVEILFRR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002032 methanolic fraction Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 230000005611 electricity Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000004744 fabric Substances 0.000 description 9
- 239000000498 cooling water Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000006835 compression Effects 0.000 description 4
- 238000007906 compression Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3407925A DE3407925C1 (de) | 1984-03-03 | 1984-03-03 | Verfahren zur Herstellung von Terephthalsaeuredimethylester aus p-Xylol und Methanol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS251094B2 true CS251094B2 (en) | 1987-06-11 |
Family
ID=6229536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS851507A CS251094B2 (en) | 1984-03-03 | 1985-03-04 | Method of terephthalic acid's dimethyl ester production |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4642369A (fr) |
| EP (1) | EP0156133B1 (fr) |
| JP (1) | JPS60204747A (fr) |
| AR (1) | AR245686A1 (fr) |
| BG (1) | BG45698A3 (fr) |
| BR (1) | BR8500934A (fr) |
| CS (1) | CS251094B2 (fr) |
| DE (2) | DE3407925C1 (fr) |
| IN (1) | IN163349B (fr) |
| MX (1) | MX161720A (fr) |
| PL (1) | PL145300B1 (fr) |
| RO (1) | RO91101B (fr) |
| SU (1) | SU1545938A3 (fr) |
| TR (1) | TR22471A (fr) |
| YU (1) | YU44491B (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4026732A1 (de) * | 1990-08-24 | 1992-02-27 | Huels Chemische Werke Ag | Verfahren zur reinigung eines oxidationsabgases mit energierueckgewinnung |
| DE19618152C1 (de) * | 1996-05-07 | 1997-08-14 | Huels Chemische Werke Ag | Verfahren zur Trennung von Rohester im DMT-Prozeß |
| DE19750491A1 (de) * | 1997-11-14 | 1999-05-20 | Huels Chemische Werke Ag | Hochsiederkreislauf im DMT-Prozeß |
| US8193402B2 (en) * | 2007-12-03 | 2012-06-05 | Gevo, Inc. | Renewable compositions |
| KR20100095004A (ko) | 2007-12-03 | 2010-08-27 | 게보 인코포레이티드 | 재생 조성물 |
| BRPI1008287A2 (pt) * | 2009-02-24 | 2016-03-15 | Gevo Inc | métodos de preparação de butadieno e isopreno renováveis |
| BR112012009385A2 (pt) * | 2009-10-06 | 2017-09-26 | Gevo Inc | processo integrado para converter seletivamente isobutanol renovável em p-xileno |
| JP2013516487A (ja) | 2010-01-08 | 2013-05-13 | ジーヴォ，インコーポレイテッド | 再生可能な化学物質を調製するための統合的方法 |
| KR20120123742A (ko) * | 2010-01-29 | 2012-11-09 | 게노마티카 인코포레이티드 | Ｐ-톨루에이트 및 테레프탈레이트 생합성 미생물 및 생합성 방법 |
| WO2011140560A1 (fr) | 2010-05-07 | 2011-11-10 | Gevo, Inc. | Carburant d'avion de base à caractère renouvelable issu de l'isobutanol |
| TW201247596A (en) | 2011-04-19 | 2012-12-01 | Gevo Inc | Variations on prins-like chemistry to produce 2,5-dimethylhexadiene from isobutanol |
| DE102012105876A1 (de) | 2012-07-02 | 2014-01-02 | Oxea Gmbh | Verfahren zur Herstellung von Terephthalsäure und ihren Derivaten |
| FI125589B2 (en) * | 2013-04-08 | 2022-03-31 | Stora Enso Oyj | Processes for deoxidation of bio-based materials and production of bio-based terephthalic acid and olefinic monomers |
| CN105985240A (zh) * | 2015-02-04 | 2016-10-05 | 华东理工大学 | 增塑剂生产酯化过程强化新工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2894978A (en) * | 1956-07-02 | 1959-07-14 | Chemische Werke Witten Gmbh | Process of producing esters of phthalic acids by oxidation of xylene and toluic acid ester mixtures |
| DE1071688B (de) * | 1958-06-14 | 1959-12-24 | Basf Ag | Verfahren zur Verbesserung der Oxydationsgeschwindigkeit der bei Luftoxydation von xylol oder von gemischen aus xylol und p-toluylsaeuremethylestern anfallenden gemische |
| NL110864C (fr) * | 1958-11-07 | |||
| US3076019A (en) * | 1959-12-21 | 1963-01-29 | Standard Oil Co | Process for production of dimethyl terephthalate |
| DE2427875C3 (de) * | 1974-06-10 | 1980-03-20 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Gewinnung von Dimethylterephthalat und von Zwischenprodukten der Dimethylterephthalat-Herstellung |
| US4096340A (en) * | 1975-06-03 | 1978-06-20 | Teijin Hercules Chemical Co., Ltd. | Process for the preparation of dimethyl terephthalate |
-
1984
- 1984-03-03 DE DE3407925A patent/DE3407925C1/de not_active Expired
- 1984-12-27 IN IN1038/MAS/84A patent/IN163349B/en unknown
-
1985
- 1985-02-07 DE DE8585101275T patent/DE3560052D1/de not_active Expired
- 1985-02-07 EP EP85101275A patent/EP0156133B1/fr not_active Expired
- 1985-02-18 SU SU853856864A patent/SU1545938A3/ru active
- 1985-02-26 AR AR85299607A patent/AR245686A1/es active
- 1985-02-27 RO RO117778A patent/RO91101B/ro unknown
- 1985-02-27 TR TR8623A patent/TR22471A/xx unknown
- 1985-02-28 YU YU313/85A patent/YU44491B/xx unknown
- 1985-02-28 BG BG069043A patent/BG45698A3/xx unknown
- 1985-02-28 MX MX204464A patent/MX161720A/es unknown
- 1985-03-01 BR BR8500934A patent/BR8500934A/pt not_active IP Right Cessation
- 1985-03-01 PL PL1985252194A patent/PL145300B1/pl unknown
- 1985-03-04 JP JP60041378A patent/JPS60204747A/ja active Granted
- 1985-03-04 CS CS851507A patent/CS251094B2/cs unknown
- 1985-03-04 US US06/707,696 patent/US4642369A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| RO91101A (fr) | 1987-03-30 |
| YU44491B (en) | 1990-08-31 |
| YU31385A (en) | 1987-10-31 |
| IN163349B (fr) | 1988-09-10 |
| AR245686A1 (es) | 1994-02-28 |
| PL145300B1 (en) | 1988-08-31 |
| US4642369A (en) | 1987-02-10 |
| MX161720A (es) | 1990-12-18 |
| JPH0566378B2 (fr) | 1993-09-21 |
| BR8500934A (pt) | 1985-10-22 |
| EP0156133B1 (fr) | 1987-01-14 |
| TR22471A (tr) | 1987-07-22 |
| DE3407925C1 (de) | 1985-09-05 |
| DE3560052D1 (en) | 1987-02-19 |
| EP0156133A1 (fr) | 1985-10-02 |
| RO91101B (ro) | 1987-04-01 |
| SU1545938A3 (ru) | 1990-02-23 |
| BG45698A3 (en) | 1989-07-14 |
| PL252194A1 (en) | 1985-09-24 |
| JPS60204747A (ja) | 1985-10-16 |
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