SK278043B6 - Method of production of alkylmetacrylate - Google Patents

Method of production of alkylmetacrylate Download PDF

Info

Publication number: SK278043B6
Authority: SK; Slovakia
Prior art keywords: propyne; propadiene; mixture; catalyst; carbon atoms
Prior art date: 1989-04-11

Application number

SK1779-90A

Other languages

English (en)

Slovak (sk)

Other versions

SK177990A3 (en

Inventor

Michael Doyle

Gogh Johan Van

Ravenswaay Claasen J C Van

Original Assignee

Michael Doyle

Gogh Johan Van

Van Ravenswaay Claasen J. C.

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

1995-11-08

1990-04-09 Application filed by Michael Doyle, Gogh Johan Van, Van Ravenswaay Claasen J. C. filed Critical Michael Doyle

1995-11-08 Publication of SK177990A3 publication Critical patent/SK177990A3/sk

1995-11-08 Publication of SK278043B6 publication Critical patent/SK278043B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 57
238000004519 manufacturing process Methods 0.000 title claims abstract description 6
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims abstract description 108
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims abstract description 82
239000000203 mixture Substances 0.000 claims abstract description 58
239000003054 catalyst Substances 0.000 claims abstract description 48
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 15
239000007788 liquid Substances 0.000 claims abstract description 14
238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 9
229910052799 carbon Inorganic materials 0.000 claims abstract description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 44
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 44
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
-1 alkyl methacrylate Chemical compound 0.000 claims description 26
125000004432 carbon atom Chemical group C* 0.000 claims description 25
239000001294 propane Substances 0.000 claims description 22
238000006473 carboxylation reaction Methods 0.000 claims description 20
239000002904 solvent Substances 0.000 claims description 20
238000006317 isomerization reaction Methods 0.000 claims description 19
230000021523 carboxylation Effects 0.000 claims description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 12
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 11
229910002091 carbon monoxide Inorganic materials 0.000 claims description 11
230000003197 catalytic effect Effects 0.000 claims description 10
239000002737 fuel gas Substances 0.000 claims description 10
229910052751 metal Inorganic materials 0.000 claims description 9
239000002184 metal Substances 0.000 claims description 9
229910052763 palladium Inorganic materials 0.000 claims description 8
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 4
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 4
230000000737 periodic effect Effects 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical group 0.000 claims description 3
229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
238000000895 extractive distillation Methods 0.000 claims description 2
238000005201 scrubbing Methods 0.000 claims description 2
238000005336 cracking Methods 0.000 abstract description 7
238000004523 catalytic cracking Methods 0.000 abstract description 5
150000001875 compounds Chemical class 0.000 abstract description 2
238000010438 heat treatment Methods 0.000 abstract description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
230000015572 biosynthetic process Effects 0.000 abstract 1
239000000047 product Substances 0.000 description 17
229930195733 hydrocarbon Natural products 0.000 description 12
150000002430 hydrocarbons Chemical class 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 10
238000004821 distillation Methods 0.000 description 9
239000007789 gas Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
239000006096 absorbing agent Substances 0.000 description 6
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
239000004215 Carbon black (E152) Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000000926 separation method Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
239000000243 solution Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-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
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 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
238000000605 extraction Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
238000005984 hydrogenation reaction Methods 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
150000002825 nitriles Chemical class 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000003495 polar organic solvent Substances 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000004064 recycling Methods 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
150000003457 sulfones Chemical class 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
HTEJLXYOJZOXKM-UHFFFAOYSA-N 1,1-dibromoprop-1-ene Chemical group CC=C(Br)Br HTEJLXYOJZOXKM-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
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
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
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
125000004423 acyloxy group Chemical group 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
125000002947 alkylene group Chemical group 0.000 description 1
150000001361 allenes Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 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
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000002585 base Substances 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
150000001721 carbon Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000001311 chemical methods and process Methods 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
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
238000006731 degradation reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
230000008021 deposition Effects 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
230000000694 effects Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002148 esters Chemical class 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
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
125000004438 haloalkoxy group Chemical group 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction 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
230000000415 inactivating effect Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
229940035429 isobutyl alcohol Drugs 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
239000012263 liquid product Substances 0.000 description 1
UPKIHOQVIBBESY-UHFFFAOYSA-N magnesium;carbanide Chemical compound [CH3-].[CH3-].[Mg+2] UPKIHOQVIBBESY-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 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
238000002156 mixing Methods 0.000 description 1
SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-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
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002941 palladium compounds Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 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
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
JKQOEJHZBHHOLG-UHFFFAOYSA-N propa-1,2-diene propane Chemical compound CCC.C=C=C JKQOEJHZBHHOLG-UHFFFAOYSA-N 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
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 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
150000003460 sulfonic acids Chemical class 0.000 description 1
239000013589 supplement Substances 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
239000003440 toxic substance Substances 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
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 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
231100000925 very toxic Toxicity 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

Landscapes

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)

SK1779-90A 1989-04-11 1990-04-09 Method of production of alkylmetacrylate SK278043B6 (en)

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 (2)

Publication Number	Publication Date
SK177990A3 SK177990A3 (en)	1995-11-08
SK278043B6 true SK278043B6 (en)	1995-11-08

Family

ID=10654768

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1779-90A SK278043B6 (en)	1989-04-11	1990-04-09	Method of production of alkylmetacrylate

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)	SK278043B6 (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
DE69116149T2 (de) *	1991-10-30	1996-06-27	Shell Int Research	Verfahren zur Herstellung von Acrylestern
EP0724558B1 (fr) *	1993-08-19	1998-04-29	Shell Internationale Researchmaatschappij B.V.	Procede de carbonylation de composes acetyleniquement insatures
KR19990081902A (ko) *	1996-01-24	1999-11-15	앤쥼 쉐이크 바쉬어+마틴 험프리스	프로핀의 제조방법
EP0870753A1 (fr) *	1997-04-04	1998-10-14	Imperial Chemical Industries Plc	Procédé de préparation d'esters méthacryliques
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
EP2256102B1 (fr)	2008-03-25	2018-09-26	Sumitomo Chemical Company, Limited	Procédé de fabrication d'un composé alcoxycarbonyle
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

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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 ES ES90200829T patent/ES2056365T3/es not_active Expired - Lifetime
- 1990-04-05 DE DE69010733T patent/DE69010733T2/de not_active Expired - Lifetime
- 1990-04-05 EP EP90200829A patent/EP0392601B1/fr not_active Expired - Lifetime
- 1990-04-09 DD DD90339561A patent/DD293577A5/de not_active IP Right Cessation
- 1990-04-09 KR KR1019900004842A patent/KR0173121B1/ko not_active Expired - Lifetime
- 1990-04-09 CA CA002014152A patent/CA2014152C/fr not_active Expired - Lifetime
- 1990-04-09 SK SK1779-90A patent/SK278043B6/sk unknown
- 1990-04-09 BR BR909001676A patent/BR9001676A/pt not_active IP Right Cessation
- 1990-04-09 JP JP2092353A patent/JP2914713B2/ja not_active Expired - Lifetime
- 1990-04-09 NZ NZ233254A patent/NZ233254A/en unknown
- 1990-04-09 AU AU53054/90A patent/AU624697B2/en not_active Expired
- 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 PT PT93698A patent/PT93698B/pt not_active IP Right Cessation

Also Published As

Publication number	Publication date
NZ233254A (en)	1991-05-28
KR0173121B1 (ko)	1999-03-30
EP0392601A3 (fr)	1992-01-15
CN1046519A (zh)	1990-10-31
EP0392601A2 (fr)	1990-10-17
JP2914713B2 (ja)	1999-07-05
EP0392601B1 (fr)	1994-07-20
SK177990A3 (en)	1995-11-08
AU624697B2 (en)	1992-06-18
DE69010733T2 (de)	1994-12-01
JPH02290831A (ja)	1990-11-30
DE69010733D1 (de)	1994-08-25
BR9001676A (pt)	1991-05-14
ES2056365T3 (es)	1994-10-01
PT93698B (pt)	1996-08-30
CN1027587C (zh)	1995-02-08
KR900016089A (ko)	1990-11-12
DD293577A5 (de)	1991-09-05
CA2014152A1 (fr)	1990-10-11
CA2014152C (fr)	1999-05-11
PT93698A (pt)	1990-11-20
CZ177990A3 (cs)	1998-05-13
AU5305490A (en)	1990-10-18
GB8908079D0 (en)	1989-05-24
CZ284057B6 (cs)	1998-08-12

Publication	Publication Date	Title
US4307257A (en)	1981-12-22	Process for production of tertiary butyl alcohol
EP0031205B1 (fr)	1984-10-17	Carbonylation d'éthylène ou de propylène
SK177990A3 (en)	1995-11-08	Method of production of alkylmetacrylate
US4256909A (en)	1981-03-17	Preparation of dimethyl butanedicarboxylates
JP2997422B2 (ja)	2000-01-11	イソアミレン中の２−メチル−１−ブテンと２−メチル−２−ブテンの比の制御方法
AU737649B2 (en)	2001-08-23	A process for the preparation of methacrylate esters
US5081286A (en)	1992-01-14	Process for the preparation of an alkyl methacrylate
EP0684939B1 (fr)	1998-11-25	Production d'ether di-isopropylique
EP0539628B1 (fr)	1996-01-03	Procédé de préparation d'esters acryliques
JPH05194320A (ja)	1993-08-03	アセチレンを連続的にカルボニル化する方法
KR20080112348A (ko)	2008-12-24	메타크릴산메틸의 제조방법
AU707322B2 (en)	1999-07-08	Process for the preparation of propyne
RU2177930C1 (ru)	2002-01-10	Способ получения олигомеров алкенов
JPH11228498A (ja)	1999-08-24	メタクリル酸メチルの製造方法
JPS58110524A (ja)	1983-07-01	軽質オレフイン系炭化水素の異性化方法
EP0975576B1 (fr)	2001-09-12	Procede servant a preparer des esters de methacrylate
CA1152534A (fr)	1983-08-23	Procede de production d'un alcool butylique tertiaire
JPH0227979B2 (fr)	1990-06-20
JPH0495033A (ja)	1992-03-27	２，３―ジメチルブテン類の製法
CA2243240A1 (fr)	1997-07-31	Procede de preparation de propyne