DE1618204B1 - Verfahren zum Entfernen von Phthalid aus Phtalsäureanhydrid - Google Patents
Verfahren zum Entfernen von Phthalid aus PhtalsäureanhydridInfo
- Publication number
- DE1618204B1 DE1618204B1 DE1967C0041427 DEC0041427A DE1618204B1 DE 1618204 B1 DE1618204 B1 DE 1618204B1 DE 1967C0041427 DE1967C0041427 DE 1967C0041427 DE C0041427 A DEC0041427 A DE C0041427A DE 1618204 B1 DE1618204 B1 DE 1618204B1
- Authority
- DE
- Germany
- Prior art keywords
- phthalic anhydride
- phthalide
- oxidation
- water
- 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.)
- Pending
Links
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 title claims description 90
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 title claims description 46
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 title claims description 45
- 238000000034 method Methods 0.000 title claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 38
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 34
- 238000007254 oxidation reaction Methods 0.000 claims description 33
- 230000003647 oxidation Effects 0.000 claims description 32
- 229940078552 o-xylene Drugs 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000012808 vapor phase Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 230000003197 catalytic effect Effects 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- -1 phthalic anhydride Phthalide Chemical compound 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 241000158147 Sator Species 0.000 claims 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000001627 detrimental effect Effects 0.000 claims 1
- RJYMRRJVDRJMJW-UHFFFAOYSA-L dibromomanganese Chemical compound Br[Mn]Br RJYMRRJVDRJMJW-UHFFFAOYSA-L 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 1
- 230000009965 odorless effect Effects 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 150000004053 quinones Chemical class 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 235000012239 silicon dioxide Nutrition 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 229910001935 vanadium oxide Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 238000010306 acid treatment Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 125000005506 phthalide group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JEPDBWHGNKPOHW-UHFFFAOYSA-N 2-benzofuran-1,3-dione;phthalic acid Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1.OC(=O)C1=CC=CC=C1C(O)=O JEPDBWHGNKPOHW-UHFFFAOYSA-N 0.000 description 1
- GVDRVTQHGGOZTO-UHFFFAOYSA-N CC1=CC=CC=C1C.OC(=O)C1=CC=CC=C1C(O)=O Chemical group CC1=CC=CC=C1C.OC(=O)C1=CC=CC=C1C(O)=O GVDRVTQHGGOZTO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/573—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US525344A US3407216A (en) | 1966-02-07 | 1966-02-07 | Method for reducing phthalide content of phthalic anhydride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618204B1 true DE1618204B1 (de) | 1972-05-04 |
Family
ID=24092851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967C0041427 Pending DE1618204B1 (de) | 1966-02-07 | 1967-02-06 | Verfahren zum Entfernen von Phthalid aus Phtalsäureanhydrid |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3407216A (en, 2012) |
| BE (1) | BE693711A (en, 2012) |
| DE (1) | DE1618204B1 (en, 2012) |
| ES (1) | ES337046A1 (en, 2012) |
| FR (1) | FR1510451A (en, 2012) |
| GB (1) | GB1154124A (en, 2012) |
| NL (1) | NL6701396A (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5885944A (en) * | 1996-05-21 | 1999-03-23 | The Lubrizol Corporation | Low chlorine polyalkylene substituted carboxylic acylating agent compositions and compounds derived therefrom |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2511861A (en) * | 1950-06-20 | Purification of phthalic anhydride | ||
| US3201423A (en) * | 1961-12-08 | 1965-08-17 | Mid Century Corp | Process for oxidizing alkyl benzenes to phthalic anhydride |
-
1966
- 1966-02-07 US US525344A patent/US3407216A/en not_active Expired - Lifetime
-
1967
- 1967-01-23 GB GB3340/67A patent/GB1154124A/en not_active Expired
- 1967-01-27 NL NL6701396A patent/NL6701396A/xx unknown
- 1967-02-06 BE BE693711D patent/BE693711A/xx unknown
- 1967-02-06 DE DE1967C0041427 patent/DE1618204B1/de active Pending
- 1967-02-06 ES ES337046A patent/ES337046A1/es not_active Expired
- 1967-02-06 FR FR93770A patent/FR1510451A/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2511861A (en) * | 1950-06-20 | Purification of phthalic anhydride | ||
| US3201423A (en) * | 1961-12-08 | 1965-08-17 | Mid Century Corp | Process for oxidizing alkyl benzenes to phthalic anhydride |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1510451A (fr) | 1968-01-19 |
| ES337046A1 (es) | 1968-01-16 |
| BE693711A (en, 2012) | 1967-08-07 |
| US3407216A (en) | 1968-10-22 |
| GB1154124A (en) | 1969-06-04 |
| NL6701396A (en, 2012) | 1967-08-08 |
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