DE3302127C2 - - Google Patents
Info
- Publication number
- DE3302127C2 DE3302127C2 DE3302127A DE3302127A DE3302127C2 DE 3302127 C2 DE3302127 C2 DE 3302127C2 DE 3302127 A DE3302127 A DE 3302127A DE 3302127 A DE3302127 A DE 3302127A DE 3302127 C2 DE3302127 C2 DE 3302127C2
- Authority
- DE
- Germany
- Prior art keywords
- terephthalaldehyde
- distillation
- tae
- taea
- dmt
- 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 - Lifetime
Links
- 239000000047 product Substances 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 12
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- -1 terephthalaldehyde acid methyl ester Chemical class 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 5
- PRWZYSMBJYICGO-UHFFFAOYSA-N CC1=C(C=CC(=C1)C=O)C(OC)OC Chemical compound CC1=C(C=CC(=C1)C=O)C(OC)OC PRWZYSMBJYICGO-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- MNHWRUCVFATHDL-UHFFFAOYSA-N 2-methylterephthalaldehyde Chemical compound CC1=CC(C=O)=CC=C1C=O MNHWRUCVFATHDL-UHFFFAOYSA-N 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 36
- REIDAMBAPLIATC-UHFFFAOYSA-M 4-methoxycarbonylbenzoate Chemical compound COC(=O)C1=CC=C(C([O-])=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-M 0.000 description 6
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000007669 thermal treatment Methods 0.000 description 3
- REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- POCRBRBXWBJRLE-UHFFFAOYSA-N 1,3-dimethylcyclohexa-3,5-diene-1,2-dicarboxylic acid Chemical compound CC1=CC=CC(C)(C(O)=O)C1C(O)=O POCRBRBXWBJRLE-UHFFFAOYSA-N 0.000 description 1
- OSNIIMCBVLBNGS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-(dimethylamino)propan-1-one Chemical compound CN(C)C(C)C(=O)C1=CC=C2OCOC2=C1 OSNIIMCBVLBNGS-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000006705 deacetalization reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833302127 DE3302127A1 (de) | 1983-01-22 | 1983-01-22 | Verfahren zur gewinnung einer mit terephthalaldehydsaeuremethylester angereicherten fraktion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833302127 DE3302127A1 (de) | 1983-01-22 | 1983-01-22 | Verfahren zur gewinnung einer mit terephthalaldehydsaeuremethylester angereicherten fraktion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3302127A1 DE3302127A1 (de) | 1984-07-26 |
| DE3302127C2 true DE3302127C2 (en, 2012) | 1991-02-14 |
Family
ID=6188978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833302127 Granted DE3302127A1 (de) | 1983-01-22 | 1983-01-22 | Verfahren zur gewinnung einer mit terephthalaldehydsaeuremethylester angereicherten fraktion |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3302127A1 (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391263A (en) * | 1994-01-26 | 1995-02-21 | E. I. Du Pont De Nemours And Company | Process for the separation of glycols from dimethyl terephthalate |
| CN1067978C (zh) * | 1996-06-21 | 2001-07-04 | 青岛化工研究所 | 一种对甲酰基苯甲酸甲酯的制备方法 |
-
1983
- 1983-01-22 DE DE19833302127 patent/DE3302127A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3302127A1 (de) | 1984-07-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2834140C2 (en, 2012) | ||
| DE2853991A1 (de) | Verfahren zur gewinnung von wasserfreier oder weitgehend wasserfreier ameisensaeure | |
| DE19825254C1 (de) | Verfahren zur Aufarbeitung von rohem, flüssigem Vinylacetat | |
| EP0072484B1 (de) | Verfahren zur Aufarbeitung von rohem, flüssigem Vinylacetat | |
| DE1951299A1 (de) | Veresterungs- und Extraktionsverfahren | |
| EP0127836B1 (de) | Verfahren zur destillativen Gewinnung von Ameisensäure | |
| DE2430520A1 (de) | Verfahren zur reinigung von rohem maleinsaeureanhydrid | |
| DE3302127C2 (en, 2012) | ||
| DE2405730C3 (de) | Verfahren zur Gewinnung von praktisch wasserfreiem Aceton mittels Extraktivdestillation | |
| DE3879399T2 (de) | Herstellung von trisubstituierten hydroxyalkylalkanoaten aus aldehyden. | |
| DE1927554C3 (en, 2012) | ||
| EP0053245B1 (de) | Verfahren zur Abtrennung organischer Jod-Verbindungen von Acetaldehyd | |
| DE4101879A1 (de) | Verfahren zur gewinnung von acrylsaeure aus destillationsrueckstaenden der acrylsaeuresynthese | |
| DE2253930A1 (de) | Verfahren zur herstellung von dicarbonsaeuren | |
| DE4241448C2 (de) | Verfahren zur Herstellung von schwefelfreien Dicarbonsäuredimethylestern | |
| DE3149021C1 (de) | Verfahren zur Reinigung von Terephthalaldehydsäureester | |
| DE2406401C3 (de) | Verfahren zur Herstellung einer cycloaliphatischen Dicarbonsäure | |
| DE3245544C2 (en, 2012) | ||
| DE2310824C3 (de) | Verfahren zur Gewinnung von Dimethylterephthalat und dessen Zwischenprodukten | |
| DE3011175C2 (de) | Verfahren zur Gewinnung von Dimethylterephthalat und Zwischenprodukten der DMT-Herstellung | |
| DE10117065A1 (de) | Verfahren zur Herstellung von C5-Acetat | |
| DE1103320B (de) | Verfahren zur Gewinnung von Dimethylterephthalat ausserordentlich hoher Reinheit | |
| DE2942859C2 (de) | Verfahren zur Herstellung von Terephthalsäure aus Dimethylterephthalat als Zwischenprodukt | |
| DE951809C (de) | Verfahren zur Herstellung von Carbonsaeureanhydriden aus den entsprechenden Carbonsaeuren | |
| DE1227885B (de) | Verfahren zur Gewinnung von reiner konzentrierter Essigsaeure aus waessrigen Gemischen der Paraffinoxydation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: HUELS TROISDORF AG, 5210 TROISDORF, DE |
|
| 8127 | New person/name/address of the applicant |
Owner name: HUELS AG, 4370 MARL, DE |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |