NO128491B - - Google Patents
Download PDFInfo
- Publication number
- NO128491B NO128491B NO259268A NO259268A NO128491B NO 128491 B NO128491 B NO 128491B NO 259268 A NO259268 A NO 259268A NO 259268 A NO259268 A NO 259268A NO 128491 B NO128491 B NO 128491B
- Authority
- NO
- Norway
- Prior art keywords
- gas
- washing
- monocarboxylic acid
- acetic acid
- reaction
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 116
- 239000007789 gas Substances 0.000 claims description 106
- 238000005406 washing Methods 0.000 claims description 70
- 150000002148 esters Chemical class 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 25
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 23
- 239000007788 liquid Substances 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 239000007795 chemical reaction product Substances 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 18
- 239000003599 detergent Substances 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 11
- -1 monocarboxylic acid ester Chemical class 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 description 39
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 16
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000003795 desorption Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 150000001242 acetic acid derivatives Chemical class 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 150000001243 acetic acids Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003303 reheating Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000000280 densification Methods 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0052915 | 1967-07-11 | ||
| DE19681768078 DE1768078C3 (de) | 1968-03-29 | Verfahren zur Herstellung ungesättigter Ester von Carbonsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128491B true NO128491B (xx) | 1973-11-26 |
Family
ID=25755488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO259268A NO128491B (xx) | 1967-07-11 | 1968-06-28 |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT277955B (xx) |
| BE (1) | BE717957A (xx) |
| CH (1) | CH502982A (xx) |
| CS (1) | CS152298B2 (xx) |
| DK (1) | DK123590B (xx) |
| FR (1) | FR1576672A (xx) |
| GB (1) | GB1235185A (xx) |
| NL (1) | NL6809679A (xx) |
| NO (1) | NO128491B (xx) |
| PL (1) | PL79377B1 (xx) |
| SE (1) | SE354847B (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109942370B (zh) * | 2019-04-03 | 2022-03-25 | 山东理工大学 | 绿色高效合成甲基烯丙醇的工艺 |
-
1968
- 1968-06-04 CH CH828368A patent/CH502982A/de not_active IP Right Cessation
- 1968-06-07 GB GB2721668A patent/GB1235185A/en not_active Expired
- 1968-06-17 AT AT575368A patent/AT277955B/de not_active IP Right Cessation
- 1968-06-19 CS CS453468A patent/CS152298B2/cs unknown
- 1968-06-28 NO NO259268A patent/NO128491B/no unknown
- 1968-07-01 DK DK323068A patent/DK123590B/da unknown
- 1968-07-09 NL NL6809679A patent/NL6809679A/xx unknown
- 1968-07-09 PL PL12801568A patent/PL79377B1/pl unknown
- 1968-07-10 SE SE951968A patent/SE354847B/xx unknown
- 1968-07-11 BE BE717957D patent/BE717957A/xx unknown
- 1968-07-11 FR FR1576672D patent/FR1576672A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE354847B (xx) | 1973-03-26 |
| BE717957A (xx) | 1969-01-13 |
| DE1768078B2 (de) | 1975-04-10 |
| FR1576672A (xx) | 1969-08-01 |
| CS152298B2 (xx) | 1973-12-19 |
| DE1768078A1 (de) | 1971-10-14 |
| NL6809679A (xx) | 1969-01-14 |
| DK123590B (da) | 1972-07-10 |
| AT277955B (de) | 1970-01-12 |
| GB1235185A (en) | 1971-06-09 |
| PL79377B1 (xx) | 1975-06-30 |
| CH502982A (de) | 1971-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2356878C2 (ru) | Способ получения дихлорпропанолов из глицерина | |
| US9643945B2 (en) | Process for the preparation of 2,5-furan-dicarboxylic acid | |
| US3875019A (en) | Recovery of ethylene glycol by plural stage distillation using vapor compression as an energy source | |
| NO159164B (no) | Fremgangsmaate ved fremstilling av etylenglycol. | |
| CN106588667B (zh) | 一种合成气制乙二醇工艺中亚硝酸甲酯的再生工艺和再生装置系统 | |
| TWI308146B (en) | Process for isolating vinyl acetate | |
| NO138358B (no) | Fremgangsmaate til aa sette inn en stort sett skaalformet metallisk bunn i en rotasjonssymmetrisk beholderkropp av metall | |
| NO146709B (no) | Fremgangsmaate til fremstilling av propylenoksyd | |
| CN104649887B (zh) | 一种氯乙酸生产方法及回收其生产过程中催化剂的方法 | |
| CN106699511B (zh) | 一种甘油氯化馏出液中有/无机物的回收利用方法 | |
| KR101929059B1 (ko) | 단열 질화에 의한 니트로벤젠의 생성 방법 | |
| CN109134217B (zh) | 一种环己烷氧化法生产环己酮过程中氧化装置及氧化工艺改进方法 | |
| WO2019019557A1 (zh) | 一种联产低碳发泡剂的方法 | |
| JP2012524757A (ja) | 酢酸ビニルの製造方法 | |
| NO761471L (xx) | ||
| US2771473A (en) | Ethylene oxide recovery | |
| CN114920630A (zh) | 一种乙二醇单乙烯基醚的连续化生产工艺及设备 | |
| US20160052900A1 (en) | Method for producing ethylene oxide | |
| TW201925151A (zh) | 生產環氧乙烷及乙二醇之方法 | |
| CN112479808A (zh) | 一种环己烯直接水合制备环己醇的方法 | |
| NO128491B (xx) | ||
| JP2000297055A (ja) | グリコールの単離 | |
| US10508062B2 (en) | Conversion of butanediol into butadiene, with scrubbing using diesters | |
| US2155625A (en) | Production of organic esters | |
| CN106083586B (zh) | 一种利用甲酸和乙醇合成甲酸乙酯并提纯产品的工艺方法 |