BE571721A - - Google Patents
Info
- Publication number
- BE571721A BE571721A BE571721DA BE571721A BE 571721 A BE571721 A BE 571721A BE 571721D A BE571721D A BE 571721DA BE 571721 A BE571721 A BE 571721A
- Authority
- BE
- Belgium
- Prior art keywords
- thiolacrylate
- carbon monoxide
- carbonyl
- parts
- acetylene
- Prior art date
Links
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 51
- UGFAIRIUMAVXCW-UHFFFAOYSA-N carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 41
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 41
- AWDHUGLHGCVIEG-UHFFFAOYSA-N Nickel tetracarbonyl Chemical group O#C[Ni](C#O)(C#O)C#O AWDHUGLHGCVIEG-UHFFFAOYSA-N 0.000 claims description 37
- 150000003573 thiols Chemical class 0.000 claims description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 24
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- LSDPWZHWYPCBBB-UHFFFAOYSA-N methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 11
- HKVOGMDMMCLQFJ-UHFFFAOYSA-N methyl 3-thiophen-2-ylprop-2-enoate Chemical group COC(=O)C=CC1=CC=CS1 HKVOGMDMMCLQFJ-UHFFFAOYSA-N 0.000 claims description 8
- WQAQPCDUOCURKW-UHFFFAOYSA-N Butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 claims description 7
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N Ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 5
- GFRCDOMEJDUQGT-UHFFFAOYSA-N ethyl 3-thiophen-2-ylprop-2-enoate Chemical group CCOC(=O)C=CC1=CC=CS1 GFRCDOMEJDUQGT-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- OYMYFHYKODAGPS-UHFFFAOYSA-N butyl 3-thiophen-2-ylprop-2-enoate Chemical group CCCCOC(=O)C=CC1=CC=CS1 OYMYFHYKODAGPS-UHFFFAOYSA-N 0.000 claims description 4
- JVWNNALMZBSIQY-UHFFFAOYSA-N S1C(=CC=C1)C=CC(=O)OCCCCCCCCCCCC Chemical compound S1C(=CC=C1)C=CC(=O)OCCCCCCCCCCCC JVWNNALMZBSIQY-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 34
- 239000002253 acid Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 238000007127 saponification reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- GHKCSRZBNZQHKW-UHFFFAOYSA-N 1-sulfanylethanol Chemical compound CC(O)S GHKCSRZBNZQHKW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000001184 potassium carbonate Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- SUVIGLJNEAMWEG-UHFFFAOYSA-N Propanethiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- -1 methyl methylthiolpropionate Chemical compound 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- ORTRWBYBJVGVQC-UHFFFAOYSA-N hexadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCS ORTRWBYBJVGVQC-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002815 nickel Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- OEJVNBQKBYHXHX-UHFFFAOYSA-N propyl 3-thiophen-2-ylprop-2-enoate Chemical compound CCCOC(=O)C=CC1=CC=CS1 OEJVNBQKBYHXHX-UHFFFAOYSA-N 0.000 description 2
- 239000012521 purified sample Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- GEKDEMKPCKTKEC-UHFFFAOYSA-N tetradecane-1-thiol Chemical group CCCCCCCCCCCCCCS GEKDEMKPCKTKEC-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
- BOTXZBGUFDGISB-UHFFFAOYSA-N 1-methoxyethanethiol Chemical compound COC(C)S BOTXZBGUFDGISB-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N 2-mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
- BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical group CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 description 1
- ZMRFRBHYXOQLDK-UHFFFAOYSA-N 2-phenylethanethiol Chemical compound SCCC1=CC=CC=C1 ZMRFRBHYXOQLDK-UHFFFAOYSA-N 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N 3-Pentanone Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- IUSDGVJFDZRIBR-UHFFFAOYSA-N 3-phenylpropane-1-thiol Chemical compound SCCCC1=CC=CC=C1 IUSDGVJFDZRIBR-UHFFFAOYSA-N 0.000 description 1
- WCIOCWNBVPUNBX-UHFFFAOYSA-N CCOC(C)(S)OCC Chemical compound CCOC(C)(S)OCC WCIOCWNBVPUNBX-UHFFFAOYSA-N 0.000 description 1
- HZOBDOGAMYMMLO-UHFFFAOYSA-M CSC1=C(SC=C1)CCC(=O)[O-] Chemical compound CSC1=C(SC=C1)CCC(=O)[O-] HZOBDOGAMYMMLO-UHFFFAOYSA-M 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- CKFGINPQOCXMAZ-UHFFFAOYSA-N Methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- YYWFULDGUTZMSM-UHFFFAOYSA-N S1C(=CC=C1)C=CC(=O)OC1CCCCC1 Chemical compound S1C(=CC=C1)C=CC(=O)OC1CCCCC1 YYWFULDGUTZMSM-UHFFFAOYSA-N 0.000 description 1
- FDEJSJBWOCAQAD-UHFFFAOYSA-N [Ni].O=C=[Ni] Chemical compound [Ni].O=C=[Ni] FDEJSJBWOCAQAD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- VPIAKHNXCOTPAY-UHFFFAOYSA-N heptane-1-thiol Chemical group CCCCCCCS VPIAKHNXCOTPAY-UHFFFAOYSA-N 0.000 description 1
- PMBXCGGQNSVESQ-UHFFFAOYSA-N hexane-1-thiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- USTRJLXKHMURIF-UHFFFAOYSA-N methyl 3-thiophen-2-ylpropanoate Chemical compound COC(=O)CCC1=CC=CS1 USTRJLXKHMURIF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- ZVHVRQOGCXCNDC-UHFFFAOYSA-N oxomethylidenenickel Chemical compound O=C=[Ni] ZVHVRQOGCXCNDC-UHFFFAOYSA-N 0.000 description 1
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- SMJRBWINMFUUDS-UHFFFAOYSA-M thien-2-ylacetate Chemical compound [O-]C(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE571721A true BE571721A (hu) |
Family
ID=189810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE571721D BE571721A (hu) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE571721A (hu) |
-
0
- BE BE571721D patent/BE571721A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2525212A1 (fr) | Procede de transformation catalytique d'alcanes en aldehydes insatures | |
| CA2032355C (fr) | Procede de preparation de (meth)acrylate d'alkylimidazolidone | |
| FR2727964A1 (fr) | Procede de recuperation des produits nobles legers contenus dans les residus de distillation des procedes de fabrication de l'acide acrylique et de ses esters | |
| WO2011010035A1 (fr) | Procede de fabrication d'acide acrylique bio-ressource a partir de glycerol | |
| EP0461096B1 (fr) | Procédé de fabrication de N-phénylmaléimide | |
| FR2826961A1 (fr) | Procede de preparation d'anhydride (meth) acrylique | |
| EP0946486A1 (fr) | Purification de l'acide acrylique obtenu par oxydation catalytique du propylene | |
| WO2001019769A1 (fr) | Procede de purification de l'acide acrylique obtenu par oxydation du propylene et/ou l'acroleine | |
| EP1976831B1 (fr) | Compositions a base de (meth)acrylates d'alkylimidazolidone | |
| FR2666334A1 (fr) | Procede continu de preparation d'acrylamides et de methacrylamides n-substitues. | |
| WO2013110877A1 (fr) | Procede de production d'acrylate de 2-octyle par transesterification | |
| WO2020136337A1 (fr) | Purification d'hydroperoxyde d'alkyle par distillation extractive | |
| BE571721A (hu) | ||
| FR2669628A1 (fr) | Hydrogenation d'esters gras. | |
| EP3551603A1 (fr) | Procede pour eviter le depot de polymeres dans un procede de purification d'acide (meth)acrylique | |
| FR2710907A1 (fr) | Procédé de production d'éthers tertiaires à partir d'une charge de craquage catalytique comprenant deux étapes de distillation extractive. | |
| EP0829475A1 (fr) | Procédé de fabrication de (méth) acrylates d'alkylimidazolidone | |
| WO1997035828A1 (fr) | Procede de preparation d'acide acetique et/ou d'acetate de methyle par isomerisation et carbonylation | |
| BE641380A (fr) | Procédé de fabrication de l'acide acétique et de l'acétate de butyle | |
| WO2023025999A1 (fr) | Procede perfectionne de fabrication d'acrylate de butyle de purete elevee | |
| BE584446A (hu) | ||
| WO2020136335A1 (fr) | Purification d'hydroperoxyde d'alkyle par distillation en presence de methanol et d'eau | |
| BE434734A (hu) | ||
| BE551524A (hu) | ||
| EP0200621A1 (fr) | Procédé de synthèse du trifluoro-2,2,2 éthanol |