DD293577A5 - Verfahren zur herstellung von alkylmethacrylat - Google Patents

Verfahren zur herstellung von alkylmethacrylat Download PDF

Info

Publication number: DD293577A5
Authority: DD; German Democratic Republic
Prior art keywords: propadiene; mixture; propyn; propyne; catalyst
Prior art date: 1989-04-11

Application number

DD90339561A

Other languages

German (de)

English (en)

Inventor

Michael J Doyle

Johan Van Gogh

Claasen Johan Ch Ravenswaay

Original Assignee

Shell Internationale Research Maatschappij B. V.,Nl

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.)

1989-04-11

Filing date

1990-04-09

Publication date

1991-09-05

1990-04-09 Application filed by Shell Internationale Research Maatschappij B. V.,Nl filed Critical Shell Internationale Research Maatschappij B. V.,Nl

1991-09-05 Publication of DD293577A5 publication Critical patent/DD293577A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 56
238000002360 preparation method Methods 0.000 title claims abstract description 8
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 title description 5
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims abstract description 81
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims abstract description 81
239000000203 mixture Substances 0.000 claims abstract description 55
239000003054 catalyst Substances 0.000 claims abstract description 40
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 39
238000005336 cracking Methods 0.000 claims abstract description 23
-1 alkyl methacrylate Chemical compound 0.000 claims abstract description 22
238000006473 carboxylation reaction Methods 0.000 claims abstract description 17
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 16
230000021523 carboxylation Effects 0.000 claims abstract description 16
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 15
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 11
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 11
238000004523 catalytic cracking Methods 0.000 claims abstract description 10
238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 31
239000002904 solvent Substances 0.000 claims description 19
238000006317 isomerization reaction Methods 0.000 claims description 17
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
229910052751 metal Inorganic materials 0.000 claims description 9
239000002184 metal Substances 0.000 claims description 9
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
229910052763 palladium Inorganic materials 0.000 claims description 6
JTXAHXNXKFGXIT-UHFFFAOYSA-N propane;prop-1-ene Chemical compound CCC.CC=C JTXAHXNXKFGXIT-UHFFFAOYSA-N 0.000 claims description 6
238000005406 washing Methods 0.000 claims description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
238000000895 extractive distillation Methods 0.000 claims description 3
229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
239000003915 liquefied petroleum gas Substances 0.000 abstract description 11
125000000217 alkyl group Chemical group 0.000 abstract description 3
238000004519 manufacturing process Methods 0.000 abstract description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 21
239000000047 product Substances 0.000 description 15
239000001294 propane Substances 0.000 description 15
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 12
229930195733 hydrocarbon Natural products 0.000 description 12
150000002430 hydrocarbons Chemical class 0.000 description 10
239000007789 gas Substances 0.000 description 8
230000003197 catalytic effect Effects 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
238000004821 distillation Methods 0.000 description 6
239000000463 material Substances 0.000 description 6
238000000926 separation method Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
125000001183 hydrocarbyl group Chemical group 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000243 solution Substances 0.000 description 4
230000000052 comparative effect Effects 0.000 description 3
NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
229910000073 phosphorus hydride Inorganic materials 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001030 gas--liquid chromatography Methods 0.000 description 2
125000005843 halogen 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
230000000607 poisoning effect Effects 0.000 description 2
239000003495 polar organic solvent Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
125000001174 sulfone group Chemical group 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
239000002699 waste material Substances 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical class C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
XFNJYAKDBJUJAJ-UHFFFAOYSA-N 1,2-dibromopropane Chemical compound CC(Br)CBr XFNJYAKDBJUJAJ-UHFFFAOYSA-N 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000007848 Bronsted acid Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005250 alkyl acrylate group Chemical group 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
125000003277 amino group Chemical group 0.000 description 1
BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229910000074 antimony hydride Inorganic materials 0.000 description 1
RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
YLMCNWCSNZMQAK-UHFFFAOYSA-N bis(6-methylpyridin-2-yl)-phenylphosphane Chemical compound CC1=CC=CC(P(C=2C=CC=CC=2)C=2N=C(C)C=CC=2)=N1 YLMCNWCSNZMQAK-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
244000309464 bull Species 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000006315 carbonylation Effects 0.000 description 1
238000005810 carbonylation reaction Methods 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
SVABQOITNJTVNJ-UHFFFAOYSA-N diphenyl-2-pyridylphosphine Chemical compound C1=CC=CC=C1P(C=1N=CC=CC=1)C1=CC=CC=C1 SVABQOITNJTVNJ-UHFFFAOYSA-N 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000000374 eutectic mixture Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
239000000446 fuel Substances 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
UPKIHOQVIBBESY-UHFFFAOYSA-N magnesium;carbanide Chemical compound [CH3-].[CH3-].[Mg+2] UPKIHOQVIBBESY-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
ZMVHTLOQSTVDFE-UHFFFAOYSA-N methanol;methyl 2-methylprop-2-enoate Chemical compound OC.COC(=O)C(C)=C ZMVHTLOQSTVDFE-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
VBUBYMVULIMEHR-UHFFFAOYSA-N propa-1,2-diene;prop-1-yne Chemical compound CC#C.C=C=C VBUBYMVULIMEHR-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
229940005657 pyrophosphoric acid Drugs 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical compound [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000005156 substituted alkylene group Chemical group 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000004227 thermal cracking Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
PXYCJKZSCDFXLR-UHFFFAOYSA-N tris[4-(trifluoromethyl)phenyl]phosphane Chemical compound C1=CC(C(F)(F)F)=CC=C1P(C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 PXYCJKZSCDFXLR-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Processing Of Solid Wastes (AREA)

DD90339561A 1989-04-11 1990-04-09 Verfahren zur herstellung von alkylmethacrylat DD293577A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB898908079A GB8908079D0 (en)	1989-04-11	1989-04-11	Process for the preparation of an alkyl methacrylate

Publications (1)

Publication Number	Publication Date
DD293577A5 true DD293577A5 (de)	1991-09-05

Family

ID=10654768

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90339561A DD293577A5 (de)	1989-04-11	1990-04-09	Verfahren zur herstellung von alkylmethacrylat

Country Status (15)

Country	Link
EP (1)	EP0392601B1 (fr)
JP (1)	JP2914713B2 (fr)
KR (1)	KR0173121B1 (fr)
CN (1)	CN1027587C (fr)
AU (1)	AU624697B2 (fr)
BR (1)	BR9001676A (fr)
CA (1)	CA2014152C (fr)
CZ (1)	CZ284057B6 (fr)
DD (1)	DD293577A5 (fr)
DE (1)	DE69010733T2 (fr)
ES (1)	ES2056365T3 (fr)
GB (1)	GB8908079D0 (fr)
NZ (1)	NZ233254A (fr)
PT (1)	PT93698B (fr)
SK (1)	SK177990A3 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2205820C2 (ru) *	1997-04-04	2003-06-10	ЛУСАЙТ ИНТЕРНЕЙШНЛ Ю Кей ЛИМИТЕД	Способ получения эфиров метакриловой кислоты

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US5295405A (en) *	1990-04-10	1994-03-22	U.S. Philips Corporation	Device having a plate with multiple cooperating moving parts injection molded thereon
GB9114327D0 (en) *	1991-07-03	1991-08-21	Shell Int Research	Continuous process for the carbonylation of acetylenes
GB9120122D0 (en) *	1991-09-20	1991-11-06	Shell Int Research	Process for the preparation of methacrylate esters
EP0539628B1 (fr) *	1991-10-30	1996-01-03	Shell Internationale Researchmaatschappij B.V.	Procédé de préparation d'esters acryliques
SG52409A1 (en) *	1993-08-19	1998-09-28	Shell Int Research	Process for the carbonylation of acetylenically unsaturated compounds
JP2000510818A (ja) *	1996-01-24	2000-08-22	インペリアルケミカルインダストリーズパブリックリミティドカンパニー	プロピンの製造方法
CN1305835C (zh) *	2005-04-12	2007-03-21	天津市天骄化工有限公司	多元醇丙烯酸酯的制备方法
FR2884513B1 (fr) *	2005-04-19	2009-07-03	Inst Francais Du Petrole	Procede de purification d'une coupe olefinique
JP4539599B2 (ja) *	2006-03-31	2010-09-08	住友化学株式会社	メタクリル酸メチルの製造方法
US8399699B2 (en)	2008-03-25	2013-03-19	Sumitomo Chemical Company, Limited	Process for production of alkoxycarbonyl compound
JP2013184924A (ja) *	2012-03-08	2013-09-19	Sumitomo Chemical Co Ltd	メチルアセチレンの製造方法及び触媒
JP6085206B2 (ja)	2013-03-26	2017-02-22	住友化学株式会社	メタクリル酸エステルの製造方法
JP6176965B2 (ja) *	2013-03-28	2017-08-09	住友化学株式会社	アセチレン化合物の製造方法
CN115991721B (zh) *	2021-10-18	2025-02-18	中化学科学技术研究有限公司	一种含膦化合物及其制备方法和作为乙烯齐聚催化剂组合物配体的应用

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NL257287A (fr) *	1959-10-26
US3671605A (en)	1970-12-14	1972-06-20	Foote Mineral Co	Isomerization of allenes into their corresponding terminal acetylenic isomers
BE789438A (fr)	1971-10-01	1973-01-15	Linde Ag	Procede et dispositif pour la separation de methylacetylene et/ou de propadiene d'un melange avec du propylene et/ou du propane
CA1331173C (fr) *	1986-12-05	1994-08-02	Eit Drent	Procede pour la carboxylation de composes acetyleniquement insatures
JP4941163B2 (ja)	2007-08-06	2012-05-30	パルステック工業株式会社	ホログラム記録装置及びホログラム記録装置のレーザ光の光路長調整方法

1989
- 1989-04-11 GB GB898908079A patent/GB8908079D0/en active Pending
1990
- 1990-04-05 DE DE69010733T patent/DE69010733T2/de not_active Expired - Lifetime
- 1990-04-05 EP EP90200829A patent/EP0392601B1/fr not_active Expired - Lifetime
- 1990-04-05 ES ES90200829T patent/ES2056365T3/es not_active Expired - Lifetime
- 1990-04-09 JP JP2092353A patent/JP2914713B2/ja not_active Expired - Lifetime
- 1990-04-09 NZ NZ233254A patent/NZ233254A/en unknown
- 1990-04-09 CZ CS901779A patent/CZ284057B6/cs not_active IP Right Cessation
- 1990-04-09 CN CN90101990A patent/CN1027587C/zh not_active Expired - Lifetime
- 1990-04-09 SK SK1779-90A patent/SK177990A3/sk unknown
- 1990-04-09 CA CA002014152A patent/CA2014152C/fr not_active Expired - Lifetime
- 1990-04-09 KR KR1019900004842A patent/KR0173121B1/ko not_active Expired - Lifetime
- 1990-04-09 PT PT93698A patent/PT93698B/pt not_active IP Right Cessation
- 1990-04-09 BR BR909001676A patent/BR9001676A/pt not_active IP Right Cessation
- 1990-04-09 DD DD90339561A patent/DD293577A5/de not_active IP Right Cessation
- 1990-04-09 AU AU53054/90A patent/AU624697B2/en not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2205820C2 (ru) *	1997-04-04	2003-06-10	ЛУСАЙТ ИНТЕРНЕЙШНЛ Ю Кей ЛИМИТЕД	Способ получения эфиров метакриловой кислоты

Also Published As

Publication number	Publication date
EP0392601A3 (fr)	1992-01-15
DE69010733D1 (de)	1994-08-25
GB8908079D0 (en)	1989-05-24
ES2056365T3 (es)	1994-10-01
SK278043B6 (en)	1995-11-08
CA2014152A1 (fr)	1990-10-11
DE69010733T2 (de)	1994-12-01
JP2914713B2 (ja)	1999-07-05
CZ284057B6 (cs)	1998-08-12
NZ233254A (en)	1991-05-28
AU624697B2 (en)	1992-06-18
CN1027587C (zh)	1995-02-08
JPH02290831A (ja)	1990-11-30
CN1046519A (zh)	1990-10-31
EP0392601B1 (fr)	1994-07-20
CZ177990A3 (cs)	1998-05-13
PT93698B (pt)	1996-08-30
SK177990A3 (en)	1995-11-08
KR900016089A (ko)	1990-11-12
AU5305490A (en)	1990-10-18
CA2014152C (fr)	1999-05-11
EP0392601A2 (fr)	1990-10-17
PT93698A (pt)	1990-11-20
KR0173121B1 (ko)	1999-03-30
BR9001676A (pt)	1991-05-14

Legal Events

Date	Code	Title	Description
1995-08-31	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD293577A5 (de)	1991-09-05	Verfahren zur herstellung von alkylmethacrylat
DE69711918T2 (de)	2002-08-22	Herstellung von organischen carbonsäureestern
DD297802A5 (de)	1992-01-23	Verfahren zur darstellung von phenol
DE2713195C3 (de)	1980-01-10	Verfahren zur Herstellung von Butandicarbonsäureestern
EP0973718A1 (fr)	2000-01-26	Procede d'extraction d'acide (meth)acrylique
DE69503739T2 (de)	1998-12-03	Veresterungsverfahren
DE1957167C3 (de)	1982-04-01	Verfahren zur Herstellung von Carbonsäuren durch Umsetzung von Olefinen mit Kohlenmonoxid und Wasser in Gegenwart eines Katalysators, der aus Orthophosphorsäure, Bortrifluorid und Wasser erhältlich ist
DE2400260C3 (de)	1979-10-18	Verfahren zur Abtrennung von Methacrolein aus einer Gasreaktionsmischung
EP0001242A1 (fr)	1979-04-04	Procédé de préparation d'esters d'acide adipique
DE69516098T2 (de)	2000-09-14	Verfahren zur Herstellung von Isopropylalkohol durch Hydratisierung von Propylen
EP1025076A1 (fr)	2000-08-09	Procede de production d'acide (meth)acrylique
DE69219022T2 (de)	1998-02-05	Kontinuierverfahren zur Carbonylierung von Acetylenen
DE3787849T2 (de)	1994-02-10	Verfahren zur katalytischen Transhalogenierung eines Polyiodobenzols.
DE69507414T2 (de)	1999-09-02	Verfahren zur Herstellung von Octadienen
DE3877646T2 (de)	1993-06-24	Verfahren zur herstellung von p-alkylstyrolen.
EP0657406A1 (fr)	1995-06-14	Procédé pour la séparation de mélanges propylène-propane
US5081286A (en)	1992-01-14	Process for the preparation of an alkyl methacrylate
DE2658191C2 (de)	1985-01-31	Verfahren zur Herstellung von Maleinsäureanhydrid
DE68915918T2 (de)	1994-09-29	Verfahren zur Zerlegung einer aromatischen acylierten Verbindung.HF-BF3 Komplex.
DE69604765T2 (de)	2000-11-16	Bf3-promoter-verfahren
DE69504133T2 (de)	1998-12-24	Verfahren zur Rückgewinnung eines benutzten sauren Katalysators
DE19836367A1 (de)	2000-02-17	Isolierung von Carbonsäuren durch Aminkomplexe
DE809553C (de)	1951-07-30	Verfahren zur Herstellung von p-tert. Butylphenol
DE4445825A1 (de)	1995-06-29	Monoalkylphosphin und Verfahren zur Herstellung desselben
DD153825A5 (de)	1982-02-03	Verfahren zur herstellung von gamma-chloracetessigsaeurechlorid

DD293577A5 - Verfahren zur herstellung von alkylmethacrylat - Google Patents

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Publications (1)

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ID=10654768

Family Applications (1)

Country Status (15)

Cited By (1)

Families Citing this family (14)

Family Cites Families (5)

Cited By (1)

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