CA1042468A - Method of recovering butadiene gas from an acetoxylation process - Google Patents
Method of recovering butadiene gas from an acetoxylation processInfo
- Publication number
- CA1042468A CA1042468A CA218,817A CA218817A CA1042468A CA 1042468 A CA1042468 A CA 1042468A CA 218817 A CA218817 A CA 218817A CA 1042468 A CA1042468 A CA 1042468A
- Authority
- CA
- Canada
- Prior art keywords
- butadiene
- acetic acid
- absorber
- acetoxylation
- waste gas
- 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims abstract description 254
- 238000006137 acetoxylation reaction Methods 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims abstract description 49
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 457
- 239000007789 gas Substances 0.000 claims abstract description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000002912 waste gas Substances 0.000 claims abstract description 40
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 32
- 230000007062 hydrolysis Effects 0.000 claims abstract description 31
- 238000010521 absorption reaction Methods 0.000 claims abstract description 20
- 230000000694 effects Effects 0.000 claims abstract description 18
- 238000004064 recycling Methods 0.000 claims abstract description 9
- 239000006096 absorbing agent Substances 0.000 claims description 81
- 239000001301 oxygen Substances 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000000746 purification Methods 0.000 claims description 18
- MWWXARALRVYLAE-UHFFFAOYSA-N 2-acetyloxybut-3-enyl acetate Chemical compound CC(=O)OCC(C=C)OC(C)=O MWWXARALRVYLAE-UHFFFAOYSA-N 0.000 claims description 14
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 238000007872 degassing Methods 0.000 claims description 3
- 239000013505 freshwater Substances 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003729 cation exchange resin Substances 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 125000002091 cationic group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 description 109
- 235000011054 acetic acid Nutrition 0.000 description 109
- 239000000047 product Substances 0.000 description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 230000009102 absorption Effects 0.000 description 14
- 239000000203 mixture Substances 0.000 description 10
- 229910002092 carbon dioxide Inorganic materials 0.000 description 9
- 239000001569 carbon dioxide Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- NLAMRLZPVVKXTK-UHFFFAOYSA-N but-1-enyl acetate Chemical compound CCC=COC(C)=O NLAMRLZPVVKXTK-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- MUSFRELEIXGPKU-UHFFFAOYSA-N selanylidenepalladium Chemical compound [Pd]=[Se] MUSFRELEIXGPKU-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 238000003915 air pollution Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000035508 accumulation Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/11—Purification; Separation; Use of additives by absorption, i.e. purification or separation of gaseous hydrocarbons with the aid of liquids
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1476274A JPS5534785B2 (en, 2012) | 1974-02-05 | 1974-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042468A true CA1042468A (en) | 1978-11-14 |
Family
ID=11870079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA218,817A Expired CA1042468A (en) | 1974-02-05 | 1975-01-28 | Method of recovering butadiene gas from an acetoxylation process |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4152525A (en, 2012) |
| JP (1) | JPS5534785B2 (en, 2012) |
| BE (1) | BE825219A (en, 2012) |
| CA (1) | CA1042468A (en, 2012) |
| DE (1) | DE2504638C2 (en, 2012) |
| FR (1) | FR2259806B1 (en, 2012) |
| GB (1) | GB1493705A (en, 2012) |
| IT (1) | IT1027405B (en, 2012) |
| NL (1) | NL180309C (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52133912A (en) * | 1976-05-01 | 1977-11-09 | Mitsubishi Chem Ind Ltd | Preparation of butanediol |
| JPS5839141B2 (ja) * | 1978-02-08 | 1983-08-27 | ジェイエスアール株式会社 | ジアセトキシブテンの製造方法 |
| US4228301A (en) * | 1977-10-21 | 1980-10-14 | Japan Synthetic Rubber Co., Ltd. | Process for the preparation of diacetoxybutene |
| GB9823853D0 (en) | 1998-10-30 | 1998-12-23 | Bp Chem Int Ltd | A process for making n-butyl esters from butadiene |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE520083A (en, 2012) | 1952-05-21 | |||
| GB1170222A (en) | 1968-06-10 | 1969-11-12 | Shell Int Research | Process for the preparation of Tetrahydrofuran and/or Homologues thereof |
| US3872163A (en) * | 1972-01-19 | 1975-03-18 | Kuraray Co | Method of preparing 1,4-diacyloxy-2-butenes |
| US3917720A (en) * | 1973-05-30 | 1975-11-04 | Gen Electric | Continuous process for the production of a diol from a diol ester |
-
1974
- 1974-02-05 JP JP1476274A patent/JPS5534785B2/ja not_active Expired
-
1975
- 1975-01-27 NL NLAANVRAGE7500895,A patent/NL180309C/xx not_active IP Right Cessation
- 1975-01-28 CA CA218,817A patent/CA1042468A/en not_active Expired
- 1975-01-29 IT IT67213/75A patent/IT1027405B/it active
- 1975-01-30 US US05/545,504 patent/US4152525A/en not_active Expired - Lifetime
- 1975-02-04 FR FR7503458A patent/FR2259806B1/fr not_active Expired
- 1975-02-04 DE DE2504638A patent/DE2504638C2/de not_active Expired
- 1975-02-04 GB GB4661/75A patent/GB1493705A/en not_active Expired
- 1975-02-05 BE BE153093A patent/BE825219A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE825219A (fr) | 1975-08-05 |
| DE2504638A1 (de) | 1975-08-14 |
| IT1027405B (it) | 1978-11-20 |
| FR2259806B1 (en, 2012) | 1978-02-03 |
| US4152525A (en) | 1979-05-01 |
| NL7500895A (nl) | 1975-08-07 |
| FR2259806A1 (en, 2012) | 1975-08-29 |
| JPS5534785B2 (en, 2012) | 1980-09-09 |
| DE2504638C2 (de) | 1985-05-30 |
| NL180309C (nl) | 1987-02-02 |
| GB1493705A (en) | 1977-11-30 |
| NL180309B (nl) | 1986-09-01 |
| JPS50106903A (en, 2012) | 1975-08-22 |
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