SU145569A1 - The method of producing vinyl acetate - Google Patents
The method of producing vinyl acetateInfo
- Publication number
- SU145569A1 SU145569A1 SU682550A SU682550A SU145569A1 SU 145569 A1 SU145569 A1 SU 145569A1 SU 682550 A SU682550 A SU 682550A SU 682550 A SU682550 A SU 682550A SU 145569 A1 SU145569 A1 SU 145569A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- vinyl acetate
- producing vinyl
- reaction
- copper
- oxygen
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 title description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- LYVWMIHLNQLWAC-UHFFFAOYSA-N [Cl].[Cu] Chemical compound [Cl].[Cu] LYVWMIHLNQLWAC-UHFFFAOYSA-N 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 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 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Б насто щее врем винилацетат получают из ацетилена и уксусной кислоты в присутствии гетерогенных катализаторов или жидкофазным методом.At present, vinyl acetate is obtained from acetylene and acetic acid in the presence of heterogeneous catalysts or by a liquid phase method.
В авт. св. № 137511 от 19 апрел 1960 г. описан способ получени виниловых эфиров карбоновых кислот из олефинов и кислот в среде карбоновой кислоты в присутствии анионов соответствующих кислот, солей паллади и веществ, способных окисл ть металлический палладий . При использовании в качестве окислител хлорной меди в системе протекает следующа суммарна реакци :In auth. St. No. 137511, dated April 19, 1960, describes a method for preparing vinyl esters of carboxylic acids from olefins and acids in a carboxylic acid medium in the presence of anions of the corresponding acids, palladium salts, and substances capable of oxidizing metallic palladium. When chlorine copper is used as an oxidizing agent in the system, the following total reaction proceeds:
CH2 CH2-i СНзСООН+2СиС12 СН2 СНОСОСНз + 2НС1 + Cu2Cl2CH2 CH2-i CH3COOH + 2CiC12 CH2 SNOSOCN3 + 2HC1 + Cu2Cl2
Образующиес в результате реакции соли одновалентной меди могут быть регенерированы в соли двухвалентной меди действием надкислот , перекиси водорода, кислорода, соединени ми TpexBavieHTHbix золота и ириди и соединени ми четырехвалентных платины, никел , свинца и марганца, а также электрохимическим путем.The salts of monovalent copper formed as a result of the reaction can be regenerated in the salt of divalent copper by the action of peracids, hydrogen peroxide, oxygen, TpexBavieHTHbix compounds of gold and iridium, and compounds of tetravalent platinum, nickel, lead and manganese, as well as electrochemically.
При осуществлении процесса по авт. св. № 137511 нельз организовать ненрерывное производство, так как необходимы остановки дл смены и регенерации медного катализатора и уксусного ангидрида. Предложенный новый свободный от указанного недостатка способ получени винилацетата из этилена и уксусной кислоты в присутствии катализатора по авт. св. № 137511 заключаетс в том, что, с целью регенерации катализатора во врем процесса, одновременно с этиленом в реакционную массу подают кислород или воздух, или уксусный ангидрид.In the process of auth. St. No. 137511 it is not possible to organize continuous production, as stops are necessary for the change and regeneration of the copper catalyst and acetic anhydride. The proposed new method of obtaining vinyl acetate from ethylene and acetic acid, free from the indicated disadvantage, in the presence of a catalyst according to ed. St. No. 137511 is that, in order to regenerate the catalyst during the process, oxygen or air or acetic anhydride is supplied simultaneously with ethylene to the reaction mass.
При окислении солей Си кислородом образуетс вода, котора способствует образованию в услови х реакции уксусного альдегида, причем конкурирующа реакци образовани альдегида по скорости во много раз превосходит реакцию образовани винилацетата. ПоэтомуDuring the oxidation of Cu salts with oxygen, water is formed, which contributes to the formation of acetaldehyde under the reaction conditions, and the competitive aldehyde formation reaction is many times faster than the vinyl acetate formation reaction. therefore
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU682550A SU145569A1 (en) | 1960-10-14 | 1960-10-14 | The method of producing vinyl acetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU682550A SU145569A1 (en) | 1960-10-14 | 1960-10-14 | The method of producing vinyl acetate |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU137511 Addition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU145569A1 true SU145569A1 (en) | 1961-11-30 |
Family
ID=48301118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU682550A SU145569A1 (en) | 1960-10-14 | 1960-10-14 | The method of producing vinyl acetate |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU145569A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3274238A (en) * | 1962-07-26 | 1966-09-20 | Consortium Elektrochem Ind | Production of unsaturated esters by oxidation of olefins |
| US3281457A (en) * | 1962-08-06 | 1966-10-25 | Rhone Poulenc Sa | Process for the production of vinyl esters by the oxidation of ethylene |
| US3700729A (en) * | 1965-12-06 | 1972-10-24 | Union Oil Co | Preparation of aromatic acids |
| US7332453B2 (en) | 2004-07-29 | 2008-02-19 | 3M Innovative Properties Company | Ceramics, and methods of making and using the same |
-
1960
- 1960-10-14 SU SU682550A patent/SU145569A1/en active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3274238A (en) * | 1962-07-26 | 1966-09-20 | Consortium Elektrochem Ind | Production of unsaturated esters by oxidation of olefins |
| US3281457A (en) * | 1962-08-06 | 1966-10-25 | Rhone Poulenc Sa | Process for the production of vinyl esters by the oxidation of ethylene |
| US3700729A (en) * | 1965-12-06 | 1972-10-24 | Union Oil Co | Preparation of aromatic acids |
| US7332453B2 (en) | 2004-07-29 | 2008-02-19 | 3M Innovative Properties Company | Ceramics, and methods of making and using the same |
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