BE569036A - - Google Patents
Info
- Publication number
- BE569036A BE569036A BE569036DA BE569036A BE 569036 A BE569036 A BE 569036A BE 569036D A BE569036D A BE 569036DA BE 569036 A BE569036 A BE 569036A
- Authority
- BE
- Belgium
- Prior art keywords
- catalyst
- reaction
- oxygen
- ethylene
- gas
- Prior art date
Links
- 239000001301 oxygen Substances 0.000 claims description 194
- 229910052760 oxygen Inorganic materials 0.000 claims description 194
- 239000007789 gas Substances 0.000 claims description 191
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 133
- 150000001336 alkenes Chemical class 0.000 claims description 99
- 239000002253 acid Substances 0.000 claims description 74
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 51
- 150000001299 aldehydes Chemical class 0.000 claims description 28
- 150000007513 acids Chemical class 0.000 claims description 27
- 150000002576 ketones Chemical class 0.000 claims description 13
- 230000001590 oxidative effect Effects 0.000 claims description 11
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims 250
- 239000003054 catalyst Substances 0.000 claims 240
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 189
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 168
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 160
- 239000005977 Ethylene Substances 0.000 claims 160
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 133
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 132
- 229910001868 water Inorganic materials 0.000 claims 121
- 239000000203 mixture Substances 0.000 claims 118
- 239000000243 solution Substances 0.000 claims 117
- 239000007788 liquid Substances 0.000 claims 71
- 150000001875 compounds Chemical class 0.000 claims 56
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 50
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 49
- 239000010949 copper Substances 0.000 claims 46
- 238000006555 catalytic reaction Methods 0.000 claims 45
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 44
- 230000003647 oxidation Effects 0.000 claims 44
- 238000007254 oxidation reaction Methods 0.000 claims 44
- 229960000583 acetic acid Drugs 0.000 claims 43
- 229910052802 copper Inorganic materials 0.000 claims 42
- 235000011054 acetic acid Nutrition 0.000 claims 41
- 230000003197 catalytic effect Effects 0.000 claims 41
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims 41
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 40
- 239000007800 oxidant agent Substances 0.000 claims 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 38
- 150000003839 salts Chemical class 0.000 claims 37
- 229910052736 halogen Inorganic materials 0.000 claims 33
- 239000000047 product Substances 0.000 claims 33
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 32
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 32
- 150000002367 halogens Chemical class 0.000 claims 29
- -1 peroxide compounds Chemical class 0.000 claims 29
- 230000008569 process Effects 0.000 claims 29
- 239000000460 chlorine Substances 0.000 claims 28
- 238000005406 washing Methods 0.000 claims 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 27
- 229910052801 chlorine Inorganic materials 0.000 claims 27
- 101150003085 Pdcl gene Proteins 0.000 claims 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 25
- 229910000510 noble metal Inorganic materials 0.000 claims 25
- 239000002912 waste gas Substances 0.000 claims 25
- 229910052742 iron Inorganic materials 0.000 claims 24
- 229910052763 palladium Inorganic materials 0.000 claims 22
- 238000007792 addition Methods 0.000 claims 21
- 229910052751 metal Inorganic materials 0.000 claims 21
- 239000002184 metal Substances 0.000 claims 21
- 238000001556 precipitation Methods 0.000 claims 21
- 230000008929 regeneration Effects 0.000 claims 21
- 238000011069 regeneration method Methods 0.000 claims 21
- 230000015572 biosynthetic process Effects 0.000 claims 20
- 229910002666 PdCl2 Inorganic materials 0.000 claims 19
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- 238000004519 manufacturing process Methods 0.000 claims 19
- 239000000463 material Substances 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 19
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 18
- 238000010438 heat treatment Methods 0.000 claims 18
- 239000000741 silica gel Substances 0.000 claims 18
- 229910002027 silica gel Inorganic materials 0.000 claims 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 17
- 230000008901 benefit Effects 0.000 claims 17
- 230000000694 effects Effects 0.000 claims 17
- 239000011521 glass Substances 0.000 claims 17
- 239000011949 solid catalyst Substances 0.000 claims 17
- 150000002739 metals Chemical class 0.000 claims 16
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 14
- 229940045803 cuprous chloride Drugs 0.000 claims 14
- 229910017604 nitric acid Inorganic materials 0.000 claims 14
- 239000002002 slurry Substances 0.000 claims 14
- 239000007787 solid Substances 0.000 claims 14
- 239000007795 chemical reaction product Substances 0.000 claims 13
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 13
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 13
- 230000009466 transformation Effects 0.000 claims 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 12
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims 12
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims 12
- 230000009471 action Effects 0.000 claims 12
- 239000002244 precipitate Substances 0.000 claims 12
- 239000000126 substance Substances 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 150000001728 carbonyl compounds Chemical class 0.000 claims 11
- 229960003280 cupric chloride Drugs 0.000 claims 11
- 230000002829 reductive effect Effects 0.000 claims 11
- 239000010802 sludge Substances 0.000 claims 11
- 238000001816 cooling Methods 0.000 claims 10
- 229910052500 inorganic mineral Chemical class 0.000 claims 10
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 10
- 239000011707 mineral Chemical class 0.000 claims 10
- 235000010755 mineral Nutrition 0.000 claims 10
- 150000004053 quinones Chemical class 0.000 claims 10
- 229920006395 saturated elastomer Polymers 0.000 claims 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 9
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 9
- 150000001450 anions Chemical class 0.000 claims 9
- 238000004880 explosion Methods 0.000 claims 9
- 239000011261 inert gas Substances 0.000 claims 9
- 239000007791 liquid phase Substances 0.000 claims 9
- 230000009467 reduction Effects 0.000 claims 9
- 238000000926 separation method Methods 0.000 claims 9
- 239000010936 titanium Substances 0.000 claims 9
- 229910052719 titanium Inorganic materials 0.000 claims 9
- 239000006227 byproduct Substances 0.000 claims 8
- 230000007423 decrease Effects 0.000 claims 8
- 239000006260 foam Substances 0.000 claims 8
- 150000004820 halides Chemical class 0.000 claims 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 8
- 230000005855 radiation Effects 0.000 claims 8
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims 8
- 229960004319 trichloroacetic acid Drugs 0.000 claims 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 7
- 239000007864 aqueous solution Substances 0.000 claims 7
- 150000001735 carboxylic acids Chemical class 0.000 claims 7
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 claims 7
- 238000004821 distillation Methods 0.000 claims 7
- 150000002736 metal compounds Chemical class 0.000 claims 7
- 230000007935 neutral effect Effects 0.000 claims 7
- 230000036961 partial effect Effects 0.000 claims 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 7
- 239000000725 suspension Substances 0.000 claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 6
- 239000001569 carbon dioxide Substances 0.000 claims 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 6
- 229910017052 cobalt Inorganic materials 0.000 claims 6
- 239000010941 cobalt Substances 0.000 claims 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 6
- 238000004090 dissolution Methods 0.000 claims 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 6
- 238000002474 experimental method Methods 0.000 claims 6
- 230000002349 favourable effect Effects 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 6
- 229910052753 mercury Inorganic materials 0.000 claims 6
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 6
- 230000000737 periodic effect Effects 0.000 claims 6
- 239000012071 phase Substances 0.000 claims 6
- 235000011121 sodium hydroxide Nutrition 0.000 claims 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 5
- 230000002378 acidificating effect Effects 0.000 claims 5
- 239000013543 active substance Substances 0.000 claims 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 5
- 238000009835 boiling Methods 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 239000000084 colloidal system Substances 0.000 claims 5
- 150000001879 copper Chemical class 0.000 claims 5
- 239000002270 dispersing agent Substances 0.000 claims 5
- 230000001681 protective effect Effects 0.000 claims 5
- 239000012495 reaction gas Substances 0.000 claims 5
- 239000011541 reaction mixture Substances 0.000 claims 5
- 238000004064 recycling Methods 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 4
- 229910052684 Cerium Inorganic materials 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 4
- 229910021555 Chromium Chloride Inorganic materials 0.000 claims 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 4
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims 4
- 230000008859 change Effects 0.000 claims 4
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 claims 4
- 238000005474 detonation Methods 0.000 claims 4
- 229910001882 dioxygen Inorganic materials 0.000 claims 4
- 238000009826 distribution Methods 0.000 claims 4
- 238000000605 extraction Methods 0.000 claims 4
- 238000001914 filtration Methods 0.000 claims 4
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims 4
- 239000012535 impurity Substances 0.000 claims 4
- 150000002505 iron Chemical class 0.000 claims 4
- 159000000014 iron salts Chemical class 0.000 claims 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 4
- 238000005259 measurement Methods 0.000 claims 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 230000002035 prolonged effect Effects 0.000 claims 4
- 239000010453 quartz Substances 0.000 claims 4
- 239000000376 reactant Substances 0.000 claims 4
- 230000035484 reaction time Effects 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 3
- 229910001069 Ti alloy Inorganic materials 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000000956 alloy Substances 0.000 claims 3
- 229910045601 alloy Inorganic materials 0.000 claims 3
- 230000001174 ascending effect Effects 0.000 claims 3
- 239000003610 charcoal Substances 0.000 claims 3
- 239000012295 chemical reaction liquid Substances 0.000 claims 3
- 239000003638 chemical reducing agent Substances 0.000 claims 3
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims 3
- 229910052804 chromium Inorganic materials 0.000 claims 3
- 239000011651 chromium Substances 0.000 claims 3
- 229910001431 copper ion Inorganic materials 0.000 claims 3
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims 3
- QYCVHILLJSYYBD-UHFFFAOYSA-L copper;oxalate Chemical compound [Cu+2].[O-]C(=O)C([O-])=O QYCVHILLJSYYBD-UHFFFAOYSA-L 0.000 claims 3
- 230000007797 corrosion Effects 0.000 claims 3
- 238000005260 corrosion Methods 0.000 claims 3
- 230000006378 damage Effects 0.000 claims 3
- 230000008030 elimination Effects 0.000 claims 3
- 238000003379 elimination reaction Methods 0.000 claims 3
- 229960003750 ethyl chloride Drugs 0.000 claims 3
- 238000005187 foaming Methods 0.000 claims 3
- 239000013505 freshwater Substances 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- 238000009434 installation Methods 0.000 claims 3
- 235000014413 iron hydroxide Nutrition 0.000 claims 3
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 claims 3
- 229910052748 manganese Inorganic materials 0.000 claims 3
- 239000011572 manganese Substances 0.000 claims 3
- 238000002156 mixing Methods 0.000 claims 3
- 238000006386 neutralization reaction Methods 0.000 claims 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 3
- 150000002894 organic compounds Chemical class 0.000 claims 3
- 229910052762 osmium Inorganic materials 0.000 claims 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 3
- 150000002941 palladium compounds Chemical class 0.000 claims 3
- 239000004033 plastic Substances 0.000 claims 3
- 229920003023 plastic Polymers 0.000 claims 3
- 239000001103 potassium chloride Substances 0.000 claims 3
- 235000011164 potassium chloride Nutrition 0.000 claims 3
- 239000000843 powder Substances 0.000 claims 3
- 239000001294 propane Substances 0.000 claims 3
- 230000001603 reducing effect Effects 0.000 claims 3
- 229910052709 silver Inorganic materials 0.000 claims 3
- 239000004332 silver Substances 0.000 claims 3
- 229910052720 vanadium Inorganic materials 0.000 claims 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims 2
- 239000005749 Copper compound Substances 0.000 claims 2
- 235000016936 Dendrocalamus strictus Nutrition 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 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 claims 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims 2
- 229910021380 Manganese Chloride Inorganic materials 0.000 claims 2
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 claims 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 2
- 229910002651 NO3 Inorganic materials 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
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- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- HQQMWVFTWZBFCU-UHFFFAOYSA-M sodium perchloric acid perchlorate Chemical compound [Na+].OCl(=O)(=O)=O.[O-]Cl(=O)(=O)=O HQQMWVFTWZBFCU-UHFFFAOYSA-M 0.000 claims 1
- 239000011343 solid material Substances 0.000 claims 1
- 239000007790 solid phase Substances 0.000 claims 1
- 239000012265 solid product Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 230000003068 static effect Effects 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 239000006228 supernatant Substances 0.000 claims 1
- 230000009182 swimming Effects 0.000 claims 1
- 229920003002 synthetic resin Polymers 0.000 claims 1
- 239000000057 synthetic resin Substances 0.000 claims 1
- 238000012360 testing method Methods 0.000 claims 1
- 239000011135 tin Substances 0.000 claims 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical class CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 1
- 229960004418 trolamine Drugs 0.000 claims 1
- 229920006305 unsaturated polyester Polymers 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE569036A true BE569036A (enrdf_load_stackoverflow) |
Family
ID=188151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE569036D BE569036A (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE569036A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2170614C1 (ru) * | 2000-04-11 | 2001-07-20 | Открытое акционерное общество "Всероссийский научно-исследовательский институт органического синтеза" | Способ регенерации катализатора жидкофазного окисления олефинов в альдегиды и кетоны |
-
0
- BE BE569036D patent/BE569036A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2170614C1 (ru) * | 2000-04-11 | 2001-07-20 | Открытое акционерное общество "Всероссийский научно-исследовательский институт органического синтеза" | Способ регенерации катализатора жидкофазного окисления олефинов в альдегиды и кетоны |
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