DE2202483C3 - - Google Patents
Info
- Publication number
- DE2202483C3 DE2202483C3 DE19722202483 DE2202483A DE2202483C3 DE 2202483 C3 DE2202483 C3 DE 2202483C3 DE 19722202483 DE19722202483 DE 19722202483 DE 2202483 A DE2202483 A DE 2202483A DE 2202483 C3 DE2202483 C3 DE 2202483C3
- Authority
- DE
- Germany
- Prior art keywords
- oxidation
- pseudocumene
- trimellitic acid
- trimellitic
- acid
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 40
- 238000007254 oxidation reaction Methods 0.000 claims description 35
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-Trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 claims description 33
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 27
- 230000003647 oxidation Effects 0.000 claims description 26
- 238000006297 dehydration reaction Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 150000007513 acids Chemical class 0.000 claims description 13
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 13
- 230000000977 initiatory Effects 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- 239000012452 mother liquor Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000004508 fractional distillation Methods 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 238000007792 addition Methods 0.000 claims description 2
- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 16
- 150000001299 aldehydes Chemical class 0.000 description 12
- 229960000583 Acetic Acid Drugs 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 7
- 239000012429 reaction media Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002763 monocarboxylic acids Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- QAHREYKOYSIQPH-UHFFFAOYSA-L Cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229910052803 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 231100000078 corrosive Toxicity 0.000 description 2
- 231100001010 corrosive Toxicity 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical class CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 description 1
- HCSDAMGBOVWGEO-UHFFFAOYSA-N 3-oxo-3-phenylpropanal Chemical compound O=CCC(=O)C1=CC=CC=C1 HCSDAMGBOVWGEO-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Incidol Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N Triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 238000004164 analytical calibration Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000005172 methylbenzenes Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005590 trimellitic acid group Chemical group 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL14570471 | 1971-01-19 | ||
| PL14570471A PL72985B2 (fr) | 1971-01-19 | 1971-01-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2202483A1 DE2202483A1 (de) | 1972-08-03 |
| DE2202483B2 DE2202483B2 (de) | 1977-03-31 |
| DE2202483C3 true DE2202483C3 (fr) | 1977-11-10 |
Family
ID=19953236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722202483 Granted DE2202483B2 (de) | 1971-01-19 | 1972-01-19 | Verfahren zur herstellung von trimellithsaeureanhydrid aus pseudocumol |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5320020B1 (fr) |
| DE (1) | DE2202483B2 (fr) |
| FR (1) | FR2122514B1 (fr) |
| GB (1) | GB1348091A (fr) |
| IT (1) | IT968033B (fr) |
| NL (1) | NL7200646A (fr) |
| PL (1) | PL72985B2 (fr) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE573049A (fr) * |
-
1971
- 1971-01-19 PL PL14570471A patent/PL72985B2/pl unknown
- 1971-10-06 IT IT2955671A patent/IT968033B/it active
-
1972
- 1972-01-13 GB GB156872A patent/GB1348091A/en not_active Expired
- 1972-01-17 NL NL7200646A patent/NL7200646A/xx not_active Application Discontinuation
- 1972-01-19 DE DE19722202483 patent/DE2202483B2/de active Granted
- 1972-01-19 JP JP755072A patent/JPS5320020B1/ja active Pending
- 1972-01-19 FR FR7201710A patent/FR2122514B1/fr not_active Expired
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