CA2525174C - Process for preparing vinyl acetate - Google Patents
Process for preparing vinyl acetate Download PDFInfo
- Publication number
- CA2525174C CA2525174C CA002525174A CA2525174A CA2525174C CA 2525174 C CA2525174 C CA 2525174C CA 002525174 A CA002525174 A CA 002525174A CA 2525174 A CA2525174 A CA 2525174A CA 2525174 C CA2525174 C CA 2525174C
- Authority
- CA
- Canada
- Prior art keywords
- acetic acid
- column
- section
- rectification
- vinyl 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 - Fee Related
Links
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 title description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 329
- 238000000034 method Methods 0.000 claims abstract description 59
- 239000007789 gas Substances 0.000 claims abstract description 55
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000005977 Ethylene Substances 0.000 claims abstract description 35
- 239000007788 liquid Substances 0.000 claims abstract description 18
- 238000012423 maintenance Methods 0.000 claims abstract description 3
- 238000009738 saturating Methods 0.000 claims abstract description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 238000005259 measurement Methods 0.000 description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 239000006200 vaporizer Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000009834 vaporization Methods 0.000 description 5
- 230000008016 vaporization Effects 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- -1 alkali metal acetates Chemical class 0.000 description 2
- 230000001174 ascending effect Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 150000002343 gold Chemical class 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002940 palladium Chemical class 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- UWIKQJCVLSOKTO-UHFFFAOYSA-N 2-acetyloxyethenyl acetate Chemical compound CC(=O)OC=COC(C)=O UWIKQJCVLSOKTO-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- 229920013683 Celanese Polymers 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/11—Automated chemical analysis
- Y10T436/117497—Automated chemical analysis with a continuously flowing sample or carrier stream
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004053184A DE102004053184B4 (de) | 2004-11-04 | 2004-11-04 | Verfahren zur Sättigung ethylenhaltiger Gase mit Essigsäure |
| DE102004053184.6 | 2004-11-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2525174A1 CA2525174A1 (en) | 2006-05-04 |
| CA2525174C true CA2525174C (en) | 2008-09-09 |
Family
ID=35519926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002525174A Expired - Fee Related CA2525174C (en) | 2004-11-04 | 2005-11-02 | Process for preparing vinyl acetate |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7202377B2 (enExample) |
| EP (1) | EP1655279B1 (enExample) |
| JP (1) | JP5362170B2 (enExample) |
| KR (1) | KR101263221B1 (enExample) |
| CN (1) | CN1769259B (enExample) |
| BR (1) | BRPI0504946A (enExample) |
| CA (1) | CA2525174C (enExample) |
| DE (1) | DE102004053184B4 (enExample) |
| MX (1) | MXPA05011806A (enExample) |
| MY (1) | MY135979A (enExample) |
| SG (1) | SG122042A1 (enExample) |
| TW (1) | TW200619190A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008001366A1 (de) * | 2008-04-24 | 2009-10-29 | Wacker Chemie Ag | Verfahren zur Herstellung von ungesättigten Carbonsäureestern |
| CN102516006B (zh) * | 2011-11-11 | 2014-07-02 | 天津大学 | 醋酸乙烯生产过程乙烯回收方法及装置 |
| CN102936198B (zh) * | 2012-10-12 | 2016-05-25 | 天津大学 | 生产醋酸乙烯的方法 |
| US10947178B2 (en) | 2017-11-21 | 2021-03-16 | Wacker Chemie Ag | Method for producing vinyl acetate |
| CN112209830B (zh) * | 2020-10-20 | 2021-08-27 | 天津大学 | 醋酸乙烯酯的生产方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3840590A (en) * | 1971-01-22 | 1974-10-08 | Celanese Corp | Alkanoic acid recycle system in process for catalytic production of an alkenyl alkanoate from an alkene and an alkanoic acid |
| US6420595B1 (en) * | 2001-09-10 | 2002-07-16 | Millennium Petrochemicals, Inc. | Process control for vinyl acetate manufacture |
-
2004
- 2004-11-04 DE DE102004053184A patent/DE102004053184B4/de not_active Expired - Lifetime
- 2004-11-04 BR BRPI0504946-6A patent/BRPI0504946A/pt not_active IP Right Cessation
-
2005
- 2005-10-26 EP EP05023388.1A patent/EP1655279B1/de not_active Expired - Lifetime
- 2005-10-28 US US11/261,319 patent/US7202377B2/en not_active Expired - Lifetime
- 2005-11-01 JP JP2005317957A patent/JP5362170B2/ja not_active Expired - Lifetime
- 2005-11-02 MY MYPI20055170A patent/MY135979A/en unknown
- 2005-11-02 KR KR1020050104339A patent/KR101263221B1/ko not_active Expired - Fee Related
- 2005-11-02 CA CA002525174A patent/CA2525174C/en not_active Expired - Fee Related
- 2005-11-02 SG SG200508456A patent/SG122042A1/en unknown
- 2005-11-03 MX MXPA05011806A patent/MXPA05011806A/es active IP Right Grant
- 2005-11-04 CN CN2005101175767A patent/CN1769259B/zh not_active Expired - Lifetime
- 2005-11-04 TW TW094138667A patent/TW200619190A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE102004053184A1 (de) | 2006-05-11 |
| TW200619190A (en) | 2006-06-16 |
| EP1655279A1 (de) | 2006-05-10 |
| SG122042A1 (en) | 2006-05-26 |
| EP1655279B1 (de) | 2017-02-22 |
| JP2006131632A (ja) | 2006-05-25 |
| DE102004053184B4 (de) | 2013-12-12 |
| CN1769259A (zh) | 2006-05-10 |
| US20060094896A1 (en) | 2006-05-04 |
| CA2525174A1 (en) | 2006-05-04 |
| HK1086820A1 (en) | 2006-09-29 |
| KR20060052413A (ko) | 2006-05-19 |
| CN1769259B (zh) | 2012-03-07 |
| MXPA05011806A (es) | 2006-05-25 |
| US7202377B2 (en) | 2007-04-10 |
| MY135979A (en) | 2008-07-31 |
| BRPI0504946A (pt) | 2006-06-27 |
| JP5362170B2 (ja) | 2013-12-11 |
| KR101263221B1 (ko) | 2013-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7576236B2 (en) | Utilization of acetic acid reaction heat in other process plants | |
| US6663692B2 (en) | Process for purifying carbon dioxide-containing gas streams | |
| KR20020039665A (ko) | 벤젠의 사이클로헥산으로의 수소화 방법 | |
| CA2525174C (en) | Process for preparing vinyl acetate | |
| US4562283A (en) | Continuous separation of maleic anhydride from gaseous reaction mixtures | |
| RU2326106C2 (ru) | Способ получения монохлоруксусной кислоты | |
| US20250019333A1 (en) | Process for preparing isoprenal and/or prenal | |
| WO2024030439A1 (en) | Catalyst for olefin acetoxylation | |
| HK1086820B (en) | Process for preparing vinyl acetate | |
| US6620965B1 (en) | Process for vinyl acetate | |
| US20240343661A1 (en) | Catalyst and process for hydrogenation of olefins | |
| JP6724161B2 (ja) | 酢酸ビニルの製造方法 | |
| EP4565557A1 (en) | Zone catalyst loading and processes for the acetoxylation of olefins using the same | |
| KR20230019134A (ko) | 아세트산의 생성 및 정제 | |
| WO2024246272A1 (en) | Processes for the preparation of citral and interrelated products | |
| JP2023528449A (ja) | 過マンガン酸塩還元化合物を除去することによる、酢酸を製造するための方法 | |
| TH35235A (th) | กระบวนการสำหรับการผลิตไดอะซีทอกซิบิวทีน |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20141103 |