DE2646808C3 - Verfahren zur Reinigung von im Zuge der Anthrachinonherstellung erhaltenem Phthalsäureanhydrid - Google Patents
Verfahren zur Reinigung von im Zuge der Anthrachinonherstellung erhaltenem PhthalsäureanhydridInfo
- Publication number
- DE2646808C3 DE2646808C3 DE19762646808 DE2646808A DE2646808C3 DE 2646808 C3 DE2646808 C3 DE 2646808C3 DE 19762646808 DE19762646808 DE 19762646808 DE 2646808 A DE2646808 A DE 2646808A DE 2646808 C3 DE2646808 C3 DE 2646808C3
- Authority
- DE
- Germany
- Prior art keywords
- phthalic anhydride
- psa
- phthalic
- crude
- acetic 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
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 title claims description 33
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 17
- 238000000746 purification Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 8
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title description 6
- 150000004056 anthraquinones Chemical class 0.000 title description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 57
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 16
- 238000007669 thermal treatment Methods 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- 229930192627 Naphthoquinone Natural products 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 150000002791 naphthoquinones Chemical class 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 150000002927 oxygen compounds Chemical class 0.000 claims description 6
- OTBHDFWQZHPNPU-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1CCCC2 OTBHDFWQZHPNPU-UHFFFAOYSA-N 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- RMOGNKXSGZNPEZ-UHFFFAOYSA-N [O].C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 Chemical compound [O].C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RMOGNKXSGZNPEZ-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 15
- 239000012535 impurity Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000012452 mother liquor Substances 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- -1 thionaphthalene Chemical class 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- GDJPWWULUNHAAJ-UHFFFAOYSA-N anthracene-9,10-dione naphthalene Chemical compound C1=CC=CC2=CC=CC=C12.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O GDJPWWULUNHAAJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003464 sulfur compounds Chemical class 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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- GOMCKELMLXHYHH-UHFFFAOYSA-L dipotassium;phthalate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=CC=C1C([O-])=O GOMCKELMLXHYHH-UHFFFAOYSA-L 0.000 description 1
- HQWKKEIVHQXCPI-UHFFFAOYSA-L disodium;phthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C([O-])=O HQWKKEIVHQXCPI-UHFFFAOYSA-L 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940110728 nitrogen / oxygen Drugs 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- AEVLXTNMRFEOAG-UHFFFAOYSA-L potassium sodium hydrogen carbonate acetate Chemical compound [Na+].[K+].CC([O-])=O.OC([O-])=O AEVLXTNMRFEOAG-UHFFFAOYSA-L 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009183 running Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 238000005406 washing 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762646808 DE2646808C3 (de) | 1976-10-16 | 1976-10-16 | Verfahren zur Reinigung von im Zuge der Anthrachinonherstellung erhaltenem Phthalsäureanhydrid |
| CH1241677A CH633549A5 (en) | 1976-10-16 | 1977-10-11 | Process for purifying phthalic anhydride |
| GB4245977A GB1549533A (en) | 1976-10-16 | 1977-10-12 | Process for the purification of phthalic anhydride |
| BE2056340A BE859720A (fr) | 1976-10-16 | 1977-10-14 | Procede de purification d'anhydride phtalique |
| JP52122558A JPS5845436B2 (ja) | 1976-10-16 | 1977-10-14 | 無水フタル酸の精製法 |
| FR7731062A FR2367759A1 (fr) | 1976-10-16 | 1977-10-14 | Procede de purification d'anhydride phtalique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762646808 DE2646808C3 (de) | 1976-10-16 | 1976-10-16 | Verfahren zur Reinigung von im Zuge der Anthrachinonherstellung erhaltenem Phthalsäureanhydrid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2646808A1 DE2646808A1 (de) | 1978-04-20 |
| DE2646808B2 DE2646808B2 (de) | 1979-01-25 |
| DE2646808C3 true DE2646808C3 (de) | 1979-09-20 |
Family
ID=5990635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762646808 Expired DE2646808C3 (de) | 1976-10-16 | 1976-10-16 | Verfahren zur Reinigung von im Zuge der Anthrachinonherstellung erhaltenem Phthalsäureanhydrid |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5845436B2 (enExample) |
| BE (1) | BE859720A (enExample) |
| CH (1) | CH633549A5 (enExample) |
| DE (1) | DE2646808C3 (enExample) |
| FR (1) | FR2367759A1 (enExample) |
| GB (1) | GB1549533A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114853705A (zh) * | 2022-04-24 | 2022-08-05 | 河北海力香料股份有限公司 | 一种4-氯代邻苯二甲酸单钠盐反应母液回收制备氯代邻苯二甲酸酐的方法 |
| CN117986217B (zh) * | 2024-04-03 | 2024-06-04 | 南京化学试剂股份有限公司 | 一种苯酐原料处理方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR648163A (fr) * | 1927-05-13 | 1928-12-06 | Cie Nat Matieres Colorantes | Procédé de purification de l'anhydride phtalique brut obtenu par catalyse |
| FR1429745A (fr) * | 1964-04-02 | 1966-02-25 | Basf Ag | Procédé pour la production d'anhydride phtalique pur à partir d'o-xylène |
| RO59914A (enExample) * | 1972-04-15 | 1976-06-15 | ||
| DE2245555C2 (de) * | 1972-09-16 | 1982-06-09 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Anthrachinon |
-
1976
- 1976-10-16 DE DE19762646808 patent/DE2646808C3/de not_active Expired
-
1977
- 1977-10-11 CH CH1241677A patent/CH633549A5/de not_active IP Right Cessation
- 1977-10-12 GB GB4245977A patent/GB1549533A/en not_active Expired
- 1977-10-14 FR FR7731062A patent/FR2367759A1/fr active Granted
- 1977-10-14 BE BE2056340A patent/BE859720A/xx unknown
- 1977-10-14 JP JP52122558A patent/JPS5845436B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE859720A (fr) | 1978-04-14 |
| JPS5845436B2 (ja) | 1983-10-08 |
| DE2646808A1 (de) | 1978-04-20 |
| DE2646808B2 (de) | 1979-01-25 |
| FR2367759B1 (enExample) | 1982-11-12 |
| JPS5350132A (en) | 1978-05-08 |
| CH633549A5 (en) | 1982-12-15 |
| GB1549533A (en) | 1979-08-08 |
| FR2367759A1 (fr) | 1978-05-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |