SA112330234B1 - عملية لإنتاج ألدهيد غير مشبع و/أو حمض كربوكسلي غير مشبع - Google Patents
عملية لإنتاج ألدهيد غير مشبع و/أو حمض كربوكسلي غير مشبع Download PDFInfo
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- SA112330234B1 SA112330234B1 SA112330234A SA112330234A SA112330234B1 SA 112330234 B1 SA112330234 B1 SA 112330234B1 SA 112330234 A SA112330234 A SA 112330234A SA 112330234 A SA112330234 A SA 112330234A SA 112330234 B1 SA112330234 B1 SA 112330234B1
- Authority
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- Saudi Arabia
- Prior art keywords
- catalyst
- raw material
- temperature
- gas
- reaction
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 31
- 230000008569 process Effects 0.000 title claims abstract description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 159
- 238000006243 chemical reaction Methods 0.000 claims abstract description 108
- 239000002994 raw material Substances 0.000 claims abstract description 64
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims abstract description 36
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 32
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 25
- 230000003647 oxidation Effects 0.000 claims abstract description 19
- 230000009466 transformation Effects 0.000 claims abstract description 15
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 8
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000003197 catalytic effect Effects 0.000 claims abstract description 6
- 239000007789 gas Substances 0.000 claims description 76
- 239000000843 powder Substances 0.000 claims description 27
- 230000000694 effects Effects 0.000 claims description 20
- 150000001253 acrylic acids Chemical class 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
- 229910001882 dioxygen Inorganic materials 0.000 claims description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- 238000012856 packing Methods 0.000 claims description 5
- 239000012495 reaction gas Substances 0.000 claims description 5
- XGRYDJSRYGHYOO-UHFFFAOYSA-N Thesine Natural products C1=CC(O)=CC=C1C1C(C(=O)OCC2C3CCCN3CC2)C(C=2C=CC(O)=CC=2)C1C(=O)OCC1C2CCCN2CC1 XGRYDJSRYGHYOO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- ORSLXQZSKCIHDH-UHFFFAOYSA-N prop-2-enal;prop-2-enoic acid Chemical compound C=CC=O.OC(=O)C=C ORSLXQZSKCIHDH-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000002159 abnormal effect Effects 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 230000008859 change Effects 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000009826 distribution Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000011049 filling Methods 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000005728 strengthening Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 241001136792 Alle Species 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 2
- 239000011609 ammonium molybdate Substances 0.000 description 2
- 229940010552 ammonium molybdate Drugs 0.000 description 2
- 235000018660 ammonium molybdate Nutrition 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 235000008429 bread Nutrition 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 2
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 230000033001 locomotion Effects 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000004323 potassium nitrate Substances 0.000 description 2
- 235000010333 potassium nitrate Nutrition 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ZZGXRPGQPAPARK-UWVGGRQHSA-N 3-[(5r,6r)-1-azabicyclo[3.2.1]octan-6-yl]-4-propylsulfanyl-1,2,5-thiadiazole Chemical compound C1([C@H]2CN3C[C@@]2(CCC3)[H])=NSN=C1SCCC ZZGXRPGQPAPARK-UWVGGRQHSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 101100234002 Drosophila melanogaster Shal gene Proteins 0.000 description 1
- 102100030931 Ladinin-1 Human genes 0.000 description 1
- 101710177601 Ladinin-1 Proteins 0.000 description 1
- 241001103596 Lelia Species 0.000 description 1
- 241000234435 Lilium Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 101710092224 Phosphate propanoyltransferase Proteins 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 235000015076 Shorea robusta Nutrition 0.000 description 1
- 244000166071 Shorea robusta Species 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- -1 carboxylic acid aldehyde Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005094 computer simulation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- BDWFYHUDXIDTIU-UHFFFAOYSA-N ethanol;propane-1,2,3-triol Chemical compound CCO.OCC(O)CO BDWFYHUDXIDTIU-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium 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
- 238000005259 measurement Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011020783 | 2011-02-02 | ||
| JP2011020782 | 2011-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SA112330234B1 true SA112330234B1 (ar) | 2015-01-14 |
Family
ID=46585965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SA112330234A SA112330234B1 (ar) | 2011-02-02 | 2012-01-30 | عملية لإنتاج ألدهيد غير مشبع و/أو حمض كربوكسلي غير مشبع |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8969618B2 (enExample) |
| EP (1) | EP2671862B1 (enExample) |
| JP (4) | JPWO2012105304A1 (enExample) |
| CN (2) | CN103347845B (enExample) |
| SA (1) | SA112330234B1 (enExample) |
| TW (1) | TWI507387B (enExample) |
| WO (1) | WO2012105304A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2012105304A1 (ja) * | 2011-02-02 | 2014-07-03 | 日本化薬株式会社 | 不飽和アルデヒドおよび／または不飽和カルボン酸の製造方法 |
| JP2014019675A (ja) * | 2012-07-20 | 2014-02-03 | Nippon Kayaku Co Ltd | 不飽和アルデヒドおよび／または不飽和カルボン酸の製造方法 |
| CN103772173B (zh) * | 2012-10-23 | 2016-06-08 | 中国石油天然气股份有限公司 | 一种丙烯醛的制备方法 |
| EP2990108A4 (en) * | 2013-04-25 | 2017-03-08 | Nippon Kayaku Kabushiki Kaisha | Catalyst for producing unsaturated aldehyde and/or unsaturated carboxylic acid, method for producing catalyst, and method for producing unsaturated aldehyde and/or unsaturated carboxylic acid using catalyst |
| CN105209168B (zh) * | 2013-05-09 | 2017-12-19 | 日本化药株式会社 | 不饱和醛和/或不饱和羧酸制造用催化剂、其制造方法以及不饱和醛和/或不饱和羧酸的制造方法 |
| KR101819465B1 (ko) * | 2013-07-18 | 2018-01-17 | 닛뽄 가야쿠 가부시키가이샤 | 불포화 알데히드 및/또는 불포화 카본산의 제조 방법 |
| CN104649872B (zh) * | 2013-11-19 | 2016-08-17 | 中国石油天然气股份有限公司 | 一种低碳烯烃选择性氧化的方法 |
| JP6674441B2 (ja) * | 2015-02-27 | 2020-04-01 | 日本化薬株式会社 | 不飽和アルデヒドおよび／または不飽和カルボン酸製造用触媒及びその製造方法並びに不飽和アルデヒドおよび／または不飽和カルボン酸の製造方法 |
| JP2016106082A (ja) * | 2015-11-24 | 2016-06-16 | 日本化薬株式会社 | 不飽和アルデヒドおよび／または不飽和カルボン酸の製造方法 |
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| WO2018181226A1 (ja) | 2017-03-27 | 2018-10-04 | 三菱ケミカル株式会社 | 触媒及び触媒群 |
| RU2735682C1 (ru) | 2017-03-27 | 2020-11-05 | Мицубиси Кемикал Корпорейшн | Катализатор и катализаторная группа |
| CN108325534A (zh) * | 2018-02-02 | 2018-07-27 | 上海东化环境工程有限公司 | 一种丙烯气相氧化制丙烯醛的催化剂及其应用 |
| ES2922381T3 (es) * | 2018-03-30 | 2022-09-14 | Mitsubishi Gas Chemical Co | Método para producir nitrilo aromático mediante una reacción de amoxidación |
| CN113573811B (zh) * | 2019-03-29 | 2023-12-08 | 日本化药株式会社 | 不饱和醛的制造方法 |
| CN112871182B (zh) * | 2019-11-29 | 2022-04-12 | 中国科学院大连化学物理研究所 | 一种用于异丁烯氧化制备甲基丙烯醛催化剂及制备和应用 |
| JP6932293B1 (ja) * | 2020-01-10 | 2021-09-08 | 日本化薬株式会社 | 触媒、それを用いた化合物の製造方法及び化合物 |
| KR102725875B1 (ko) * | 2020-01-14 | 2024-11-01 | 가부시기가이샤 닛뽕쇼꾸바이 | 아크릴산의 제조 방법 |
| CN115327252B (zh) * | 2022-06-27 | 2023-08-08 | 上海轩田工业设备有限公司 | 一种高低温微波性能测试调度优化方法及系统 |
| CN119303588A (zh) * | 2023-07-13 | 2025-01-14 | 中国石油天然气股份有限公司 | 一种多级孔钼铋复合金属氧化物催化剂及其制备方法与应用 |
| WO2025100265A1 (ja) * | 2023-11-09 | 2025-05-15 | 日本化薬株式会社 | 不飽和アルデヒドまたは不飽和カルボン酸の製造方法 |
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| DE2056614C3 (de) * | 1970-11-18 | 1981-04-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Acrylsäure aus Propylen |
| JP2659839B2 (ja) * | 1990-01-26 | 1997-09-30 | 株式会社日本触媒 | メタクロレインおよびメタクリル酸の製造方法 |
| JP3287066B2 (ja) * | 1993-06-28 | 2002-05-27 | 住友化学工業株式会社 | アクリル酸の製造方法 |
| JP3139285B2 (ja) | 1994-06-20 | 2001-02-26 | 住友化学工業株式会社 | アクロレインおよびアクリル酸の製造方法 |
| JP3793317B2 (ja) * | 1996-05-14 | 2006-07-05 | 日本化薬株式会社 | 触媒及び不飽和アルデヒドおよび不飽和酸の製造方法 |
| JP3775872B2 (ja) | 1996-12-03 | 2006-05-17 | 日本化薬株式会社 | アクロレイン及びアクリル酸の製造方法 |
| JP4318367B2 (ja) * | 2000-02-16 | 2009-08-19 | 株式会社日本触媒 | アクロレインおよびアクリル酸の製造方法 |
| JP3943311B2 (ja) | 2000-05-19 | 2007-07-11 | 株式会社日本触媒 | 不飽和アルデヒドおよび不飽和カルボン酸の製造方法 |
| JP3939187B2 (ja) | 2002-03-29 | 2007-07-04 | 株式会社日本触媒 | 不飽和アルデヒドの製造方法 |
| KR100553825B1 (ko) | 2003-09-01 | 2006-02-21 | 주식회사 엘지화학 | 고정층 촉매 부분 산화 반응기에서 개선된 제열 시스템을통한 불포화알데히드 및 불포화산의 제조 방법 |
| JP2005320315A (ja) | 2003-10-22 | 2005-11-17 | Nippon Shokubai Co Ltd | 接触気相酸化反応 |
| JP4867129B2 (ja) * | 2003-12-15 | 2012-02-01 | 三菱化学株式会社 | （メタ）アクリル酸または（メタ）アクロレインの製造方法 |
| CN101842341A (zh) | 2007-11-02 | 2010-09-22 | 日本化药株式会社 | 气相催化氧化反应方法 |
| JP5130562B2 (ja) | 2007-11-06 | 2013-01-30 | 日本化薬株式会社 | メタクロレイン及び／又はメタクリル酸の製造方法 |
| JPWO2012105304A1 (ja) * | 2011-02-02 | 2014-07-03 | 日本化薬株式会社 | 不飽和アルデヒドおよび／または不飽和カルボン酸の製造方法 |
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- 2012-01-16 WO PCT/JP2012/050730 patent/WO2012105304A1/ja not_active Ceased
- 2012-01-16 EP EP12742461.2A patent/EP2671862B1/en not_active Not-in-force
- 2012-01-16 US US13/982,808 patent/US8969618B2/en active Active
- 2012-01-19 TW TW101102078A patent/TWI507387B/zh not_active IP Right Cessation
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| US20130310604A1 (en) | 2013-11-21 |
| TW201233667A (en) | 2012-08-16 |
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| CN103347845A (zh) | 2013-10-09 |
| JP2012176938A (ja) | 2012-09-13 |
| US8969618B2 (en) | 2015-03-03 |
| JP6527499B2 (ja) | 2019-06-05 |
| WO2012105304A1 (ja) | 2012-08-09 |
| JP2017088606A (ja) | 2017-05-25 |
| EP2671862A1 (en) | 2013-12-11 |
| JP2018140993A (ja) | 2018-09-13 |
| CN102627537A (zh) | 2012-08-08 |
| EP2671862B1 (en) | 2018-01-10 |
| CN102627537B (zh) | 2016-03-23 |
| EP2671862A4 (en) | 2014-10-01 |
| CN103347845B (zh) | 2015-04-01 |
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