JPS5913743A - フエノ−ル類製造用触媒の回収法 - Google Patents
フエノ−ル類製造用触媒の回収法Info
- Publication number
- JPS5913743A JPS5913743A JP57123426A JP12342682A JPS5913743A JP S5913743 A JPS5913743 A JP S5913743A JP 57123426 A JP57123426 A JP 57123426A JP 12342682 A JP12342682 A JP 12342682A JP S5913743 A JPS5913743 A JP S5913743A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- compound
- phenol
- reaction
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 66
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title abstract description 63
- 238000011084 recovery Methods 0.000 title description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 37
- 150000002989 phenols Chemical class 0.000 claims abstract description 26
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 14
- 150000002697 manganese compounds Chemical class 0.000 claims abstract description 9
- 239000007791 liquid phase Substances 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 4
- 238000005895 oxidative decarboxylation reaction Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000005749 Copper compound Substances 0.000 abstract description 8
- 150000001880 copper compounds Chemical class 0.000 abstract description 8
- 150000003839 salts Chemical class 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- 150000002909 rare earth metal compounds Chemical class 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000005711 Benzoic acid Substances 0.000 description 16
- 235000010233 benzoic acid Nutrition 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000002485 combustion reaction Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000002994 raw material Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 4
- ZRVIYEJYXIDATJ-UHFFFAOYSA-N 4-Heptyloxybenzoic acid Chemical compound CCCCCCCOC1=CC=C(C(O)=O)C=C1 ZRVIYEJYXIDATJ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- -1 rare earth compound Chemical class 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NIONDZDPPYHYKY-UHFFFAOYSA-N 2-hexenoic acid Chemical class CCCC=CC(O)=O NIONDZDPPYHYKY-UHFFFAOYSA-N 0.000 description 2
- OUANAAHOQVMJCH-UHFFFAOYSA-N 4-benzoyloxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC(=O)C1=CC=CC=C1 OUANAAHOQVMJCH-UHFFFAOYSA-N 0.000 description 2
- 229910000722 Didymium Inorganic materials 0.000 description 2
- 241000224487 Didymium Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241001122767 Theaceae Species 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009841 combustion method Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920003210 poly(4-hydroxy benzoic acid) Polymers 0.000 description 2
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- QPLAKKKWUXRITA-UHFFFAOYSA-N benzoic acid;phenol Chemical class OC1=CC=CC=C1.OC(=O)C1=CC=CC=C1 QPLAKKKWUXRITA-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- 229910000009 copper(II) carbonate Inorganic materials 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004334 fluoridation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57123426A JPS5913743A (ja) | 1982-07-14 | 1982-07-14 | フエノ−ル類製造用触媒の回収法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57123426A JPS5913743A (ja) | 1982-07-14 | 1982-07-14 | フエノ−ル類製造用触媒の回収法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5913743A true JPS5913743A (ja) | 1984-01-24 |
| JPH0419980B2 JPH0419980B2 (cg-RX-API-DMAC7.html) | 1992-03-31 |
Family
ID=14860263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57123426A Granted JPS5913743A (ja) | 1982-07-14 | 1982-07-14 | フエノ−ル類製造用触媒の回収法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5913743A (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61253473A (ja) * | 1985-05-06 | 1986-11-11 | Yokogawa Hewlett Packard Ltd | デジタルオシロスコープの表示方法及びデジタルオシロスコープ |
-
1982
- 1982-07-14 JP JP57123426A patent/JPS5913743A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61253473A (ja) * | 1985-05-06 | 1986-11-11 | Yokogawa Hewlett Packard Ltd | デジタルオシロスコープの表示方法及びデジタルオシロスコープ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0419980B2 (cg-RX-API-DMAC7.html) | 1992-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI262101B (en) | Promoted multi-metal oxide catalyst | |
| JP5386847B2 (ja) | アクリル酸の製造方法 | |
| US3972949A (en) | Process for preparing glycol dimethyl ethers | |
| CN101678333A (zh) | 制备羟基芳醛的方法 | |
| TW200914414A (en) | Improved process for selective reduction of propionic acid from (meth) acrylic acid product streams | |
| KR20010072614A (ko) | 임의 치환된 ｐ-히드록시만델 화합물의 제조방법 | |
| JPS5913743A (ja) | フエノ−ル類製造用触媒の回収法 | |
| TW533194B (en) | Process for the preparation of a 4-hydroxybenzaldehyde and its derivatives | |
| CN1328991A (zh) | 2－卤甲基苯乙酸酯类的制造方法 | |
| WO2001064616A1 (en) | Process for producing aromatic carbonate | |
| JPS61221139A (ja) | ２，２，２‐トリフルオロエタノールの製造法 | |
| JPH03279336A (ja) | 分枝二量化アルコールの製造方法 | |
| CN107954951B (zh) | 一种用于制造δ-戊内酯的方法 | |
| JPS5929626A (ja) | フェノ−ル類製造用触媒有効成分の回収方法 | |
| JPS5874626A (ja) | モノエチレングリコ−ルモノメチルエ−テル、モノエチレングリコ−ル及びエタノ−ルの水素化分解製造法 | |
| Li et al. | A stereoselective synthesis of (4E, 7S)-(-)-7-methoxydodec-4-enoic acid | |
| JPS58140034A (ja) | ３，５，３′，５′−テトラ−タシヤリ−−ブチルビフエノ−ルの製造方迷 | |
| JPH02196751A (ja) | ポリアルキル芳香族化合物の酸化 | |
| JP3519427B2 (ja) | オルト位アルキル化フェノール化合物の連続製造方法 | |
| GB1564567A (en) | Preparation of mcresol | |
| JPS6332343B2 (cg-RX-API-DMAC7.html) | ||
| JPS58213728A (ja) | フエノ−ル類の製造法 | |
| Babara | Oxidation of p-Anisaldehyde to p-Anisic acid by organic clay as a novel method | |
| JPS59210076A (ja) | ２，３−ビヒドロ−２，２−ジメチル−７−ベンゾフラノ−ルの製法 | |
| JPH0699350B2 (ja) | フエノ−ル類とカテコ−ル類の分離法 |