JPS5845436B2 - 無水フタル酸の精製法 - Google Patents
無水フタル酸の精製法Info
- Publication number
- JPS5845436B2 JPS5845436B2 JP52122558A JP12255877A JPS5845436B2 JP S5845436 B2 JPS5845436 B2 JP S5845436B2 JP 52122558 A JP52122558 A JP 52122558A JP 12255877 A JP12255877 A JP 12255877A JP S5845436 B2 JPS5845436 B2 JP S5845436B2
- Authority
- JP
- Japan
- Prior art keywords
- phthalic anhydride
- acetic acid
- crude
- weight
- crystallization
- 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 82
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 title claims description 82
- 238000000034 method Methods 0.000 title claims description 29
- 238000000746 purification Methods 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 69
- 238000010438 heat treatment Methods 0.000 claims description 17
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 16
- 238000004821 distillation Methods 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000012452 mother liquor Substances 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 150000004056 anthraquinones Chemical class 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229930192627 Naphthoquinone Natural products 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 150000002791 naphthoquinones Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 150000002927 oxygen compounds Chemical class 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 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 3
- 238000002845 discoloration Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 229940110728 nitrogen / oxygen Drugs 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000012535 impurity Substances 0.000 description 19
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 6
- -1 thionaphthalene Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- AKRICVNYDOTXCL-UHFFFAOYSA-N 1-but-1-enylnaphthalene Chemical compound C1=CC=C2C(C=CCC)=CC=CC2=C1 AKRICVNYDOTXCL-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
- 238000004458 analytical method Methods 0.000 description 2
- 125000001741 organic sulfur group Chemical group 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- VTLVETAXMKXSCW-UHFFFAOYSA-N acetyl acetate;2-benzofuran-1,3-dione Chemical compound CC(=O)OC(C)=O.C1=CC=C2C(=O)OC(=O)C2=C1 VTLVETAXMKXSCW-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000001514 detection method Methods 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
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 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)
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 (2)
| Publication Number | Publication Date |
|---|---|
| JPS5350132A JPS5350132A (en) | 1978-05-08 |
| JPS5845436B2 true JPS5845436B2 (ja) | 1983-10-08 |
Family
ID=5990635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52122558A Expired JPS5845436B2 (ja) | 1976-10-16 | 1977-10-14 | 無水フタル酸の精製法 |
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
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS * |
Also Published As
| Publication number | Publication date |
|---|---|
| BE859720A (fr) | 1978-04-14 |
| DE2646808C3 (de) | 1979-09-20 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5666429B2 (ja) | エチレン性不飽和酸またはそのエステルの製造 | |
| US5145971A (en) | Process for the preparation of oxydiphthalic acid and purified oxydiphthalic anhydride from crude oxydiphthalic anhydride | |
| DE69124546D1 (de) | Verfahren zur Herstellung von N-Phenylmaleinimid | |
| CA2062142C (en) | Process for the recovery of adipic acid | |
| US4370487A (en) | Process for, respectively, the production and purification of dicarboxylic and polycarboxylic acid anhydrides | |
| JPS6233223B2 (enExample) | ||
| EP0432910B1 (en) | Process for producing highly pure 2, 6 naphthalene dicarboxylic acid | |
| US3637832A (en) | Preparation of straight chain dicarboxylic acids | |
| JPS5845436B2 (ja) | 無水フタル酸の精製法 | |
| US2393352A (en) | Manufacture of fumaric acid | |
| US3105851A (en) | Separation of recoverable materials from oxidation by-products | |
| US3564051A (en) | Production of adipic acid | |
| US3903152A (en) | Process for producing highly pure 1,12-dodecanedioic acid | |
| JP7694577B2 (ja) | フルオレノンの製造方法 | |
| US3290329A (en) | Purification of pyrrolidone | |
| US4165328A (en) | Process for separating 11-cyanoundecanoic acid, cyclohexanone and ε- | |
| EP0132450B1 (en) | Method of purifying methacrylic acid | |
| US4145353A (en) | Process for removing 1,4-naphthoquinone from phthalic anhydride | |
| JPS647064B2 (enExample) | ||
| CN116874398B (zh) | 4,4’-二氯二苯砜的制备方法 | |
| US4463197A (en) | Method for purifying phloroglucin | |
| US3215734A (en) | Process for purification of terephthalic acid | |
| US3391193A (en) | Purification of methacrylaldehyde | |
| JPH01502821A (ja) | コハク酸以外のカルボン酸類とコハク酸の混合物からコハク酸の回収方法 | |
| JPS60202839A (ja) | ジヒドロキシベンゾフエノンの製造方法 |