CA1145354A - Light ends recovery in ethyl acrylate process - Google Patents
Light ends recovery in ethyl acrylate processInfo
- Publication number
- CA1145354A CA1145354A CA000378084A CA378084A CA1145354A CA 1145354 A CA1145354 A CA 1145354A CA 000378084 A CA000378084 A CA 000378084A CA 378084 A CA378084 A CA 378084A CA 1145354 A CA1145354 A CA 1145354A
- Authority
- CA
- Canada
- Prior art keywords
- liquid
- stream
- light ends
- vacuum pump
- ethyl acrylate
- 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
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 title claims abstract description 36
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000011084 recovery Methods 0.000 title description 6
- 239000007788 liquid Substances 0.000 claims abstract description 115
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 34
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 31
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 29
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000005977 Ethylene Substances 0.000 claims abstract description 12
- 238000009835 boiling Methods 0.000 claims abstract description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 34
- 239000012530 fluid Substances 0.000 claims description 31
- 238000004821 distillation Methods 0.000 claims description 24
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 238000005292 vacuum distillation Methods 0.000 claims description 14
- 239000003112 inhibitor Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000005194 fractionation Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 235000010269 sulphur dioxide Nutrition 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229960005419 nitrogen Drugs 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 239000000306 component Substances 0.000 description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229950000688 phenothiazine Drugs 0.000 description 4
- 239000004291 sulphur dioxide Substances 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/152,885 US4301298A (en) | 1980-05-23 | 1980-05-23 | Light ends recovery in ethyl acrylate process |
| US152,885 | 1980-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1145354A true CA1145354A (en) | 1983-04-26 |
Family
ID=22544872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000378084A Expired CA1145354A (en) | 1980-05-23 | 1981-05-22 | Light ends recovery in ethyl acrylate process |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4301298A (enExample) |
| JP (1) | JPS5716837A (enExample) |
| CA (1) | CA1145354A (enExample) |
| DE (1) | DE3119555A1 (enExample) |
| FR (1) | FR2482954A1 (enExample) |
| GB (1) | GB2076814A (enExample) |
| IT (1) | IT1137482B (enExample) |
| NL (1) | NL8102533A (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4554055A (en) * | 1983-03-07 | 1985-11-19 | Phillips Petroleum Company | Solvent recovery |
| US4968834A (en) * | 1990-05-07 | 1990-11-06 | Hoechst Celanese Corporation | Recovery of acrylic acid and/or ethyl acrylate from black acid |
| EP0562139B1 (en) * | 1992-03-25 | 1995-12-13 | Showa Denko Kabushiki Kaisha | Process for preparation of lower fatty acid ester |
| US5345771A (en) * | 1993-03-25 | 1994-09-13 | John Zink Company, A Division Of Koch Engineering Company, Inc. | Process for recovering condensable compounds from inert gas-condensable compound vapor mixtures |
| JP4698778B2 (ja) * | 1999-06-03 | 2011-06-08 | 株式会社日本触媒 | （メタ）アクリル酸（エステル）の精製方法 |
| DE10143565B4 (de) * | 2001-09-05 | 2014-10-30 | Basf Se | Verfahren zur Herstellung polymerisationsfähiger Verbindungen |
| US7253374B2 (en) * | 2003-09-15 | 2007-08-07 | General Motors Corporation | Sheet-to-tube welded structure and method |
| US20050109507A1 (en) * | 2003-11-21 | 2005-05-26 | Halliburton Energy Services, Inc. | Methods of using cement compositions having long-term slurry-state stability |
| EP3205384A1 (de) * | 2016-02-15 | 2017-08-16 | Evonik Degussa GmbH | Verfahren zur vakuumdestillation einer organischen verbindung |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1972157A (en) * | 1928-12-04 | 1934-09-04 | Barrett Co | Vacuum distillation |
| US2336493A (en) * | 1940-07-23 | 1943-12-14 | Du Pont | Distillation of organic liquids polymerizable by heat |
| US3228860A (en) * | 1961-09-18 | 1966-01-11 | Phillips Petroleum Co | Overhead vapor condenser for cooling liquid for rotary pump seal |
| US3248233A (en) * | 1964-06-02 | 1966-04-26 | Coca Cola Co | Essence recovery |
| BE712804A (enExample) * | 1967-03-31 | 1968-07-31 | ||
| US3951756A (en) * | 1974-11-08 | 1976-04-20 | Celanese Corporation | Purification of alkyl esters |
| US4087208A (en) * | 1976-06-08 | 1978-05-02 | Mitsubishi Jukogyo Kabushiki Kaisha | Method for compressing mixed gas consisting of combustible gas and air |
-
1980
- 1980-05-23 US US06/152,885 patent/US4301298A/en not_active Expired - Lifetime
-
1981
- 1981-05-16 DE DE19813119555 patent/DE3119555A1/de not_active Withdrawn
- 1981-05-21 JP JP7581881A patent/JPS5716837A/ja active Pending
- 1981-05-22 NL NL8102533A patent/NL8102533A/nl not_active Application Discontinuation
- 1981-05-22 IT IT21923/81A patent/IT1137482B/it active
- 1981-05-22 CA CA000378084A patent/CA1145354A/en not_active Expired
- 1981-05-22 GB GB8115746A patent/GB2076814A/en not_active Withdrawn
- 1981-05-22 FR FR8110271A patent/FR2482954A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5716837A (en) | 1982-01-28 |
| IT8121923A0 (it) | 1981-05-22 |
| NL8102533A (nl) | 1981-12-16 |
| FR2482954B1 (enExample) | 1983-11-10 |
| FR2482954A1 (fr) | 1981-11-27 |
| IT1137482B (it) | 1986-09-10 |
| US4301298A (en) | 1981-11-17 |
| GB2076814A (en) | 1981-12-09 |
| DE3119555A1 (de) | 1982-05-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |