SA519402151B1 - محفز لإنتاج حمض ميث أكريليك, مادة منتجة للمحفز لإنتاج حمض ميث أكريليك, طريقة لإنتاج المحفز المذكور ومادة منتجة للمحفز, طريقة لإنتاج حمض ميث أكريليك, وطريقة لإنتاج إستر ميث أكريلات - Google Patents

محفز لإنتاج حمض ميث أكريليك, مادة منتجة للمحفز لإنتاج حمض ميث أكريليك, طريقة لإنتاج المحفز المذكور ومادة منتجة للمحفز, طريقة لإنتاج حمض ميث أكريليك, وطريقة لإنتاج إستر ميث أكريلات Download PDF

Info

Publication number: SA519402151B1
Authority: SA; Saudi Arabia
Prior art keywords: methacrylic acid; catalyst; producing; production; slurry
Prior art date: 2017-02-17

Application number

SA519402151A

Other languages

Arabic (ar)

English (en)

Inventor

هيراتا جون

Original Assignee

ميتسوبيشي كميكال كوربوريشن

Priority date (The priority date 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 date listed.)

2017-02-17

Filing date

2019-06-13

Publication date

2023-02-15

2019-06-13 Application filed by ميتسوبيشي كميكال كوربوريشن filed Critical ميتسوبيشي كميكال كوربوريشن

2023-02-15 Publication of SA519402151B1 publication Critical patent/SA519402151B1/ar

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CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims abstract description 138
239000003054 catalyst Substances 0.000 title claims abstract description 118
238000004519 manufacturing process Methods 0.000 title claims abstract description 94
239000012018 catalyst precursor Substances 0.000 title description 54
229910052760 oxygen Inorganic materials 0.000 claims abstract description 31
239000001301 oxygen Substances 0.000 claims abstract description 31
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 30
238000007254 oxidation reaction Methods 0.000 claims abstract description 30
239000000203 mixture Substances 0.000 claims abstract description 29
230000003647 oxidation Effects 0.000 claims abstract description 28
230000003197 catalytic effect Effects 0.000 claims abstract description 27
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 24
229910001882 dioxygen Inorganic materials 0.000 claims abstract description 23
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims abstract description 12
229910052787 antimony Inorganic materials 0.000 claims abstract description 10
229910052792 caesium Inorganic materials 0.000 claims abstract description 10
229910052746 lanthanum Inorganic materials 0.000 claims abstract description 10
229910052716 thallium Inorganic materials 0.000 claims abstract description 10
229910052804 chromium Inorganic materials 0.000 claims abstract description 9
229910052732 germanium Inorganic materials 0.000 claims abstract description 8
229910052700 potassium Inorganic materials 0.000 claims abstract description 8
229910052712 strontium Inorganic materials 0.000 claims abstract description 8
229910052785 arsenic Inorganic materials 0.000 claims abstract description 7
229910052749 magnesium Inorganic materials 0.000 claims abstract description 7
229910052759 nickel Inorganic materials 0.000 claims abstract description 7
229910052763 palladium Inorganic materials 0.000 claims abstract description 7
229910052710 silicon Inorganic materials 0.000 claims abstract description 7
229910052718 tin Inorganic materials 0.000 claims abstract description 7
229910052791 calcium Inorganic materials 0.000 claims abstract description 6
229910052742 iron Inorganic materials 0.000 claims abstract description 6
229910052708 sodium Inorganic materials 0.000 claims abstract description 6
229910052715 tantalum Inorganic materials 0.000 claims abstract description 6
229910052719 titanium Inorganic materials 0.000 claims abstract description 6
229910052796 boron Inorganic materials 0.000 claims abstract description 5
229910052744 lithium Inorganic materials 0.000 claims abstract description 5
229910052788 barium Inorganic materials 0.000 claims abstract description 4
229910052725 zinc Inorganic materials 0.000 claims abstract description 4
229910052797 bismuth Inorganic materials 0.000 claims abstract description 3
229910052738 indium Inorganic materials 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
229910052726 zirconium Inorganic materials 0.000 claims abstract description 3
239000002002 slurry Substances 0.000 claims description 88
238000000034 method Methods 0.000 claims description 41
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 30
239000000463 material Substances 0.000 claims description 27
239000007789 gas Substances 0.000 claims description 18
-1 quailt Chemical compound 0.000 claims description 18
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 15
239000002243 precursor Substances 0.000 claims description 15
229910052750 molybdenum Inorganic materials 0.000 claims description 14
239000011733 molybdenum Substances 0.000 claims description 14
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 12
229910052698 phosphorus Inorganic materials 0.000 claims description 12
239000011574 phosphorus Substances 0.000 claims description 12
239000010949 copper Substances 0.000 claims description 11
150000002148 esters Chemical class 0.000 claims description 11
239000010955 niobium Substances 0.000 claims description 11
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 9
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 9
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 9
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 9
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 8
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
239000011651 chromium Substances 0.000 claims description 8
229910052802 copper Inorganic materials 0.000 claims description 8
229910052758 niobium Inorganic materials 0.000 claims description 8
GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 8
229910052720 vanadium Inorganic materials 0.000 claims description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
150000003868 ammonium compounds Chemical class 0.000 claims description 7
150000003863 ammonium salts Chemical class 0.000 claims description 7
238000001035 drying Methods 0.000 claims description 7
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 7
239000011591 potassium Substances 0.000 claims description 7
229910052684 Cerium Inorganic materials 0.000 claims description 6
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 6
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 6
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 6
229910052733 gallium Inorganic materials 0.000 claims description 6
239000011777 magnesium Substances 0.000 claims description 6
239000010703 silicon Substances 0.000 claims description 6
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
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 claims description 5
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
239000011575 calcium Substances 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 5
229910052714 tellurium Inorganic materials 0.000 claims description 5
PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 5
239000010936 titanium Substances 0.000 claims description 5
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 4
239000000470 constituent Substances 0.000 claims description 4
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 claims description 4
229910052711 selenium Inorganic materials 0.000 claims description 4
239000011669 selenium Substances 0.000 claims description 4
GKCNVZWZCYIBPR-UHFFFAOYSA-N sulfanylideneindium Chemical compound [In]=S GKCNVZWZCYIBPR-UHFFFAOYSA-N 0.000 claims description 4
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 3
239000004570 mortar (masonry) Substances 0.000 claims description 3
229910052709 silver Inorganic materials 0.000 claims description 3
239000004332 silver Substances 0.000 claims description 3
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 3
229910052721 tungsten Inorganic materials 0.000 claims description 3
239000010937 tungsten Substances 0.000 claims description 3
239000011701 zinc Substances 0.000 claims description 3
RWHRFHQRVDUPIK-UHFFFAOYSA-N 50867-57-7 Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O RWHRFHQRVDUPIK-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
RFDFPOGXFHHCII-UHFFFAOYSA-N [Cu].[Nb] Chemical compound [Cu].[Nb] RFDFPOGXFHHCII-UHFFFAOYSA-N 0.000 claims description 2
QRSFFHRCBYCWBS-UHFFFAOYSA-N [O].[O] Chemical compound [O].[O] QRSFFHRCBYCWBS-UHFFFAOYSA-N 0.000 claims description 2
WIBOKTQZOPHFAJ-UHFFFAOYSA-N [Zr].[Bi] Chemical compound [Zr].[Bi] WIBOKTQZOPHFAJ-UHFFFAOYSA-N 0.000 claims description 2
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
DQIPXGFHRRCVHY-UHFFFAOYSA-N chromium zinc Chemical compound [Cr].[Zn] DQIPXGFHRRCVHY-UHFFFAOYSA-N 0.000 claims description 2
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
235000015250 liver sausages Nutrition 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 2
241000511343 Chondrostoma nasus Species 0.000 claims 1
241000196324 Embryophyta Species 0.000 claims 1
BMSYAGRCQOYYMZ-UHFFFAOYSA-N [As].[As] Chemical compound [As].[As] BMSYAGRCQOYYMZ-UHFFFAOYSA-N 0.000 claims 1
XBYNNYGGLWJASC-UHFFFAOYSA-N barium titanium Chemical compound [Ti].[Ba] XBYNNYGGLWJASC-UHFFFAOYSA-N 0.000 claims 1
KVXHGSVIPDOLBC-UHFFFAOYSA-N selanylidenetungsten Chemical compound [Se].[W] KVXHGSVIPDOLBC-UHFFFAOYSA-N 0.000 claims 1
239000011800 void material Substances 0.000 claims 1
229910052745 lead Inorganic materials 0.000 abstract 1
229910052748 manganese Inorganic materials 0.000 abstract 1
229910052701 rubidium Inorganic materials 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 30
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
238000002360 preparation method Methods 0.000 description 16
238000010438 heat treatment Methods 0.000 description 15
239000012071 phase Substances 0.000 description 15
238000011156 evaluation Methods 0.000 description 12
JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
150000001875 compounds Chemical class 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000011964 heteropoly acid Substances 0.000 description 8
239000003377 acid catalyst Substances 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
238000001354 calcination Methods 0.000 description 7
238000010790 dilution Methods 0.000 description 7
239000012895 dilution Substances 0.000 description 7
238000004090 dissolution Methods 0.000 description 7
238000002156 mixing Methods 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
239000002904 solvent Substances 0.000 description 7
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
239000001099 ammonium carbonate Substances 0.000 description 6
UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 6
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 6
DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
235000012501 ammonium carbonate Nutrition 0.000 description 5
229940000488 arsenic acid Drugs 0.000 description 5
238000003113 dilution method Methods 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
235000011007 phosphoric acid Nutrition 0.000 description 5
229910052703 rhodium Inorganic materials 0.000 description 5
239000010948 rhodium Substances 0.000 description 5
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 5
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
ZMCUDHNSHCRDBT-UHFFFAOYSA-M caesium bicarbonate Chemical compound [Cs+].OC([O-])=O ZMCUDHNSHCRDBT-UHFFFAOYSA-M 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
230000007423 decrease Effects 0.000 description 4
239000002184 metal Substances 0.000 description 4
229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
235000015497 potassium bicarbonate Nutrition 0.000 description 4
239000011736 potassium bicarbonate Substances 0.000 description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
241000894007 species Species 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
125000005395 methacrylic acid group Chemical group 0.000 description 3
URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
238000001694 spray drying Methods 0.000 description 3
239000012808 vapor phase Substances 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
238000007696 Kjeldahl method Methods 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WCMHZFHLWGFVCQ-UHFFFAOYSA-N [Ba].[Mn] Chemical compound [Ba].[Mn] WCMHZFHLWGFVCQ-UHFFFAOYSA-N 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
238000001636 atomic emission spectroscopy Methods 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
239000003729 cation exchange resin Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
230000002950 deficient Effects 0.000 description 2
GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000005397 methacrylic acid ester group Chemical group 0.000 description 2
ZKATWMILCYLAPD-UHFFFAOYSA-N niobium pentoxide Inorganic materials O=[Nb](=O)O[Nb](=O)=O ZKATWMILCYLAPD-UHFFFAOYSA-N 0.000 description 2
150000002823 nitrates Chemical class 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
ZFYIQPIHXRFFCZ-QMMMGPOBSA-N (2s)-2-(cyclohexylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC1CCCCC1 ZFYIQPIHXRFFCZ-QMMMGPOBSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
240000008415 Lactuca sativa Species 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
101150107869 Sarg gene Proteins 0.000 description 1
244000297179 Syringa vulgaris Species 0.000 description 1
235000004338 Syringa vulgaris Nutrition 0.000 description 1
229910021550 Vanadium Chloride Inorganic materials 0.000 description 1
ASGCFBXFVSPILZ-UHFFFAOYSA-N [B].[Zn].[Fe] Chemical compound [B].[Zn].[Fe] ASGCFBXFVSPILZ-UHFFFAOYSA-N 0.000 description 1
YAHGGFWSDYESSR-UHFFFAOYSA-N [Li].[Li].[Na].[Na] Chemical compound [Li].[Li].[Na].[Na] YAHGGFWSDYESSR-UHFFFAOYSA-N 0.000 description 1
QVMHUALAQYRRBM-UHFFFAOYSA-N [P].[P] Chemical compound [P].[P] QVMHUALAQYRRBM-UHFFFAOYSA-N 0.000 description 1
QBIJEBCHKRVPEF-UHFFFAOYSA-N [Ti].[Ti].[Sn] Chemical compound [Ti].[Ti].[Sn] QBIJEBCHKRVPEF-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000012538 ammonium bicarbonate Nutrition 0.000 description 1
VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000000748 compression moulding Methods 0.000 description 1
229940116318 copper carbonate Drugs 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
SXTLQDJHRPXDSB-UHFFFAOYSA-N copper;dinitrate;trihydrate Chemical compound O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O SXTLQDJHRPXDSB-UHFFFAOYSA-N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
238000004868 gas analysis Methods 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
150000004715 keto acids Chemical class 0.000 description 1
VVNXEADCOVSAER-UHFFFAOYSA-N lithium sodium Chemical compound [Li].[Na] VVNXEADCOVSAER-UHFFFAOYSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
PDKHNCYLMVRIFV-UHFFFAOYSA-H molybdenum;hexachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mo] PDKHNCYLMVRIFV-UHFFFAOYSA-H 0.000 description 1
VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
239000002245 particle Substances 0.000 description 1
RPESBQCJGHJMTK-UHFFFAOYSA-I pentachlorovanadium Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[V+5] RPESBQCJGHJMTK-UHFFFAOYSA-I 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
ZDHURYWHEBEGHO-UHFFFAOYSA-N potassiopotassium Chemical compound [K].[K] ZDHURYWHEBEGHO-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
235000012045 salad Nutrition 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
DFRJXBODDKCODB-UHFFFAOYSA-N strontium tantalum Chemical compound [Sr][Ta] DFRJXBODDKCODB-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
CPWJKGIJFGMVPL-UHFFFAOYSA-K tricesium;phosphate Chemical compound [Cs+].[Cs+].[Cs+].[O-]P([O-])([O-])=O CPWJKGIJFGMVPL-UHFFFAOYSA-K 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
- B01J27/198—Vanadium
- B01J27/199—Vanadium with chromium, molybdenum, tungsten or polonium
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (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)

SA519402151A 2017-02-17 2019-06-13 محفز لإنتاج حمض ميث أكريليك, مادة منتجة للمحفز لإنتاج حمض ميث أكريليك, طريقة لإنتاج المحفز المذكور ومادة منتجة للمحفز, طريقة لإنتاج حمض ميث أكريليك, وطريقة لإنتاج إستر ميث أكريلات SA519402151B1 (ar)

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JP (1)	JP6819699B2 (ja)
KR (1)	KR102310395B1 (ja)
CN (1)	CN110300622B (ja)
MY (1)	MY192057A (ja)
SA (1)	SA519402151B1 (ja)
WO (1)	WO2018150797A1 (ja)

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CN115335147A (zh) *	2020-03-31	2022-11-11	三菱化学株式会社	催化剂、异丁醛和甲基丙烯醛的制造方法、甲基丙烯酸的制造方法和甲基丙烯酸酯的制造方法
US20230234037A1 (en) *	2020-05-08	2023-07-27	Air Company Holdings, Inc.	Molybdenum-based catalysts for carbon dioxide conversion
CN113976179B (zh) *	2021-11-04	2024-02-09	淄博市翔力致高新材料有限责任公司	一种空心结构催化剂及其制备方法和用途

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JP3370589B2 (ja) *	1997-12-25	2003-01-27	三菱レイヨン株式会社	メタクリル酸製造用触媒およびそれを用いたメタクリル酸の製造法
JPH11228487A (ja)	1998-02-18	1999-08-24	Mitsubishi Rayon Co Ltd	メタクリル酸の製造法
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- 2018-01-18 JP JP2018568053A patent/JP6819699B2/ja active Active
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Publication number	Publication date
CN110300622B (zh)	2022-08-26
WO2018150797A1 (ja)	2018-08-23
CN110300622A (zh)	2019-10-01
KR20190095448A (ko)	2019-08-14
KR102310395B1 (ko)	2021-10-07
JPWO2018150797A1 (ja)	2019-12-26
JP6819699B2 (ja)	2021-01-27
MY192057A (en)	2022-07-25

Publication	Publication Date	Title
SA519402151B1 (ar)	2023-02-15	محفز لإنتاج حمض ميث أكريليك, مادة منتجة للمحفز لإنتاج حمض ميث أكريليك, طريقة لإنتاج المحفز المذكور ومادة منتجة للمحفز, طريقة لإنتاج حمض ميث أكريليك, وطريقة لإنتاج إستر ميث أكريلات
KR100191368B1 (ko)	1999-06-15	철-안티몬-몰리브덴함유 산화물 촉매 조성물 및 이의 제조방법
SU1055329A3 (ru)	1983-11-15	Способ получени метакролеина и метакриловой кислоты
CN102892499B (zh)	2015-01-28	制备改良的混合金属氧化物氨氧化催化剂的方法
KR101431293B1 (ko)	2014-08-20	아크릴로니트릴 제조용 유동상 촉매 및 아크릴로니트릴의 제조 방법
US4467113A (en)	1984-08-21	Process for producing methacrylic acid
KR101052455B1 (ko)	2011-07-28	헤테로폴리산 촉매의 재생 방법 및 메트아크릴산의 제조방법
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JP5362370B2 (ja)	2013-12-11	メタクリル酸合成用触媒の製造方法
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JP2002239388A (ja)	2002-08-27	メタクロレインおよび／またはメタクリル酸製造用触媒、その製造方法、および、メタクロレインおよび／またはメタクリル酸の製造方法
JP5199044B2 (ja)	2013-05-15	メタクロレイン及びメタクリル酸製造用触媒の調製方法
JPWO2019208715A1 (ja)	2021-05-20	メタクリル酸製造用触媒の製造方法、並びにメタクリル酸及びメタクリル酸エステルの製造方法
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