DE2038120C3 - Verfahren zur Herstellung von Allylacetat - Google Patents
Verfahren zur Herstellung von AllylacetatInfo
- Publication number
- DE2038120C3 DE2038120C3 DE2038120A DE2038120A DE2038120C3 DE 2038120 C3 DE2038120 C3 DE 2038120C3 DE 2038120 A DE2038120 A DE 2038120A DE 2038120 A DE2038120 A DE 2038120A DE 2038120 C3 DE2038120 C3 DE 2038120C3
- Authority
- DE
- Germany
- Prior art keywords
- propylene
- percent
- reaction
- concentration
- allyl acetate
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 38
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 37
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 37
- 239000007789 gas Substances 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000001294 propane Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000012495 reaction gas Substances 0.000 claims description 6
- 229910000510 noble metal Inorganic materials 0.000 claims description 4
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 239000005977 Ethylene Substances 0.000 description 11
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- 239000010970 precious metal Substances 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- -1 Propylene acetic acid oxygen Carbon dioxide Chemical compound 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000002474 experimental method Methods 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 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
- 239000001282 iso-butane Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/0242—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid flow within the bed being predominantly vertical
- B01J8/025—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid flow within the bed being predominantly vertical in a cylindrical shaped bed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00168—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles
- B01J2208/00176—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles outside the reactor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00265—Part of all of the reactants being heated or cooled outside the reactor while recycling
- B01J2208/00274—Part of all of the reactants being heated or cooled outside the reactor while recycling involving reactant vapours
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Fluid Mechanics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2038120A DE2038120C3 (de) | 1970-07-31 | 1970-07-31 | Verfahren zur Herstellung von Allylacetat |
| CS5411A CS161915B2 (enExample) | 1970-07-31 | 1971-07-22 | |
| ZA714936A ZA714936B (en) | 1970-07-31 | 1971-07-23 | Process for the preparation of allyl acetate |
| ES393606A ES393606A1 (es) | 1970-07-31 | 1971-07-24 | Procedimiento de obtencion de acetato de alilo. |
| NL7110265A NL7110265A (enExample) | 1970-07-31 | 1971-07-26 | |
| BG018163A BG19127A3 (bg) | 1970-07-31 | 1971-07-27 | Метод за получаване на алилацетат |
| GB3512671A GB1347858A (en) | 1970-07-31 | 1971-07-27 | Process for the preparation of allyl acetate |
| BE770681A BE770681A (fr) | 1970-07-31 | 1971-07-29 | Procede de preparation de l'acetate d'allyle |
| LU63628A LU63628A1 (enExample) | 1970-07-31 | 1971-07-29 | |
| AT661771A AT321873B (de) | 1970-07-31 | 1971-07-29 | Verfahren zur herstellung von allylacetat |
| BR4836/71A BR7104836D0 (pt) | 1970-07-31 | 1971-07-29 | Processo para a preparacao de acetato de alila |
| AU31761/71A AU456851B2 (en) | 1970-07-31 | 1971-07-29 | PROCESS FORTHE PREPARATION OF ATT. y T ACETATE |
| FR7128070A FR2099396A5 (enExample) | 1970-07-31 | 1971-07-30 | |
| PL1971149765A PL82098B1 (enExample) | 1970-07-31 | 1971-07-30 | |
| SU1688969A SU466652A3 (ru) | 1970-07-31 | 1971-07-30 | Способ получени аллилацетата |
| US05/511,677 US4010198A (en) | 1970-07-31 | 1974-10-03 | Process for the preparation of allyl acetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2038120A DE2038120C3 (de) | 1970-07-31 | 1970-07-31 | Verfahren zur Herstellung von Allylacetat |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2038120A1 DE2038120A1 (de) | 1972-02-10 |
| DE2038120C3 true DE2038120C3 (de) | 1979-11-22 |
Family
ID=5778528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2038120A Expired DE2038120C3 (de) | 1970-07-31 | 1970-07-31 | Verfahren zur Herstellung von Allylacetat |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT321873B (enExample) |
| AU (1) | AU456851B2 (enExample) |
| BE (1) | BE770681A (enExample) |
| BG (1) | BG19127A3 (enExample) |
| BR (1) | BR7104836D0 (enExample) |
| CS (1) | CS161915B2 (enExample) |
| DE (1) | DE2038120C3 (enExample) |
| ES (1) | ES393606A1 (enExample) |
| FR (1) | FR2099396A5 (enExample) |
| GB (1) | GB1347858A (enExample) |
| LU (1) | LU63628A1 (enExample) |
| NL (1) | NL7110265A (enExample) |
| PL (1) | PL82098B1 (enExample) |
| SU (1) | SU466652A3 (enExample) |
| ZA (1) | ZA714936B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855280A (en) * | 1972-12-08 | 1974-12-17 | Celanese Corp | Process for producing an alkenyl alkanoate from an olefin and a carboxylic acid |
-
1970
- 1970-07-31 DE DE2038120A patent/DE2038120C3/de not_active Expired
-
1971
- 1971-07-22 CS CS5411A patent/CS161915B2/cs unknown
- 1971-07-23 ZA ZA714936A patent/ZA714936B/xx unknown
- 1971-07-24 ES ES393606A patent/ES393606A1/es not_active Expired
- 1971-07-26 NL NL7110265A patent/NL7110265A/xx not_active Application Discontinuation
- 1971-07-27 GB GB3512671A patent/GB1347858A/en not_active Expired
- 1971-07-27 BG BG018163A patent/BG19127A3/xx unknown
- 1971-07-29 BE BE770681A patent/BE770681A/xx unknown
- 1971-07-29 LU LU63628A patent/LU63628A1/xx unknown
- 1971-07-29 AU AU31761/71A patent/AU456851B2/en not_active Expired
- 1971-07-29 BR BR4836/71A patent/BR7104836D0/pt unknown
- 1971-07-29 AT AT661771A patent/AT321873B/de not_active IP Right Cessation
- 1971-07-30 SU SU1688969A patent/SU466652A3/ru active
- 1971-07-30 PL PL1971149765A patent/PL82098B1/pl unknown
- 1971-07-30 FR FR7128070A patent/FR2099396A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU466652A3 (ru) | 1975-04-05 |
| LU63628A1 (enExample) | 1973-02-05 |
| BE770681A (fr) | 1972-01-31 |
| AT321873B (de) | 1975-04-25 |
| ES393606A1 (es) | 1973-08-01 |
| CS161915B2 (enExample) | 1975-06-10 |
| PL82098B1 (enExample) | 1975-10-31 |
| FR2099396A5 (enExample) | 1972-03-10 |
| BG19127A3 (bg) | 1975-04-30 |
| ZA714936B (en) | 1972-04-26 |
| AU456851B2 (en) | 1975-01-16 |
| NL7110265A (enExample) | 1972-02-02 |
| BR7104836D0 (pt) | 1973-04-05 |
| GB1347858A (en) | 1974-02-27 |
| DE2038120A1 (de) | 1972-02-10 |
| AU3176171A (en) | 1973-02-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69009393T3 (de) | Verfahren zur Herstellung eines Diesters der Kohlensäure. | |
| DE3821965C2 (de) | Verfahren zur Herstellung eines Essigsäureproduktes durch Umwandlung eines Synthesegases | |
| DE1227023B (de) | Verfahren zur Herstellung von Carbonsaeureestern | |
| DE2832136A1 (de) | Verfahren zur herstellung von synthesegas durch katalysierte zersetzung von methanol | |
| CA1119611A (en) | Process for preparing diesters of dicarboxylic acids | |
| US3725534A (en) | Method of forming complex cobalt carbonyl compounds | |
| DE69936137T2 (de) | Verfahren zur herstellung von essigsäure | |
| DE1283833B (de) | Verfahren zur Herstellung von ª-Pinen durch katalytische Isomerisierung von ª-Pinen | |
| DE68905512T2 (de) | Methode zum reaktivieren eines gruppe-viii-edelmetallkatalysators zur verwendung bei der reinigung roher terephthalsaeure. | |
| DE2038120C3 (de) | Verfahren zur Herstellung von Allylacetat | |
| DE2315037C3 (de) | Verfahren zur Herstellung von ungesättigten Estern von Carbonsäuren | |
| US4010198A (en) | Process for the preparation of allyl acetate | |
| DE69205030T2 (de) | Verfahren zur Herstellung von Diestern der Carbonsäure. | |
| KR100687510B1 (ko) | 이리듐 및 플래티늄의 존재 하의 아세트산 및/또는 메틸아세테이트의 제조 방법 | |
| DE2038120B (de) | Verfahren zur Herstellung von Allyl acetat | |
| DE3229323A1 (de) | Verfahren zur herstellung aliphatischer isocyanate durch oxidative dehydrierung von formamiden | |
| US2694091A (en) | Oxo process using mixture of alkenes and dienes | |
| PL80666B1 (enExample) | ||
| EP0267501B1 (de) | Verfahren zur kontinuierlichen Herstellung von Carbalkoxygruppen enthaltenden aliphatischen Verbindungen | |
| DE2513678C3 (de) | Verfahren zur Herstellung von praktisch ameisensäurefreier Essigsäure | |
| DE1568400C (de) | Verfahren zur Herstellung von Vinylacetat | |
| DE1909964A1 (de) | Verfahren zur Herstellung von 2-Methylen-1,3-diacetoxy-propan | |
| DE1668114B2 (de) | Verfahren zur Herstellung von Vinylacetat | |
| DE2425653A1 (de) | Verfahren zur herstellung von butandiol | |
| US3281462A (en) | Preparation of acetic anhydride by the catalyzed oxidation of acetaldehyde in the presence of amixture of boric acid and oxalic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |