TWI544956B - 處理羰化製程所產生之氣態流 - Google Patents
處理羰化製程所產生之氣態流 Download PDFInfo
- Publication number
- TWI544956B TWI544956B TW100141382A TW100141382A TWI544956B TW I544956 B TWI544956 B TW I544956B TW 100141382 A TW100141382 A TW 100141382A TW 100141382 A TW100141382 A TW 100141382A TW I544956 B TWI544956 B TW I544956B
- Authority
- TW
- Taiwan
- Prior art keywords
- carbonylation
- reaction zone
- reactant
- distillation
- combining
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 133
- 238000005810 carbonylation reaction Methods 0.000 title claims description 130
- 230000006315 carbonylation Effects 0.000 title claims description 73
- 238000012545 processing Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 312
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 126
- 238000004821 distillation Methods 0.000 claims description 126
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 125
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 116
- 239000000376 reactant Substances 0.000 claims description 98
- 239000003599 detergent Substances 0.000 claims description 94
- 150000001875 compounds Chemical class 0.000 claims description 45
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 43
- 229910052740 iodine Inorganic materials 0.000 claims description 43
- 239000011630 iodine Substances 0.000 claims description 42
- 238000005201 scrubbing Methods 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 30
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 24
- 239000007789 gas Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000006227 byproduct Substances 0.000 claims description 9
- 238000004064 recycling Methods 0.000 claims description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- 238000003860 storage Methods 0.000 claims description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000011084 recovery Methods 0.000 claims description 6
- 238000001311 chemical methods and process Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 238000011010 flushing procedure Methods 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- MROZMRCKKCNECB-UHFFFAOYSA-N CC(=O)C.[I] Chemical compound CC(=O)C.[I] MROZMRCKKCNECB-UHFFFAOYSA-N 0.000 claims description 3
- LEKJTGQWLAUGQA-UHFFFAOYSA-N acetyl iodide Chemical compound CC(I)=O LEKJTGQWLAUGQA-UHFFFAOYSA-N 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 claims description 3
- YDGMIJCIBXSCQR-UHFFFAOYSA-N methyl 2-iodoacetate Chemical compound COC(=O)CI YDGMIJCIBXSCQR-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000007670 refining Methods 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000005406 washing Methods 0.000 description 42
- 239000010935 stainless steel Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 238000012856 packing Methods 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- 238000010992 reflux Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 230000010354 integration Effects 0.000 description 4
- NIUAGEVCVWHMTA-UHFFFAOYSA-N 5-(4-iodophenyl)-1-(4-methylsulfonylphenyl)-3-(trifluoromethyl)pyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(I)=CC=2)=CC(C(F)(F)F)=N1 NIUAGEVCVWHMTA-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000000809 air pollutant Substances 0.000 description 1
- 231100001243 air pollutant Toxicity 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- -1 methyl iodide Chemical class 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000066 reactive distillation Methods 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
- 239000002904 solvent Substances 0.000 description 1
- 229910001256 stainless steel alloy Inorganic materials 0.000 description 1
- 238000012546 transfer 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
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1418—Recovery of products
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
- B01D53/86—Catalytic processes
- B01D53/8659—Removing halogens or halogen compounds
-
- 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
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/20—Halogens or halogen compounds
- B01D2257/202—Single element halogens
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1406—Multiple stage absorption
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1493—Selection of liquid materials for use as absorbents
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Environmental & Geological Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Gas Separation By Absorption (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41321210P | 2010-11-12 | 2010-11-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201226041A TW201226041A (en) | 2012-07-01 |
| TWI544956B true TWI544956B (zh) | 2016-08-11 |
Family
ID=45044714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW100141382A TWI544956B (zh) | 2010-11-12 | 2011-11-11 | 處理羰化製程所產生之氣態流 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP2637767B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5969489B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN103189125A (cg-RX-API-DMAC7.html) |
| BR (1) | BR112013011566A2 (cg-RX-API-DMAC7.html) |
| TW (1) | TWI544956B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2012064689A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201610487PA (en) * | 2014-06-17 | 2017-01-27 | Bp Chem Int Ltd | Method and apparatus for treating offgases in a acetic acid production unit |
| US20230127564A1 (en) | 2020-04-01 | 2023-04-27 | Celanese International Corporation | Processes for removing and/or reducing permanganate reducing compounds and alkyl iodides |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50187U (cg-RX-API-DMAC7.html) * | 1973-05-07 | 1975-01-06 | ||
| JPS5246924B2 (cg-RX-API-DMAC7.html) * | 1973-11-27 | 1977-11-29 | ||
| JPS54132516A (en) * | 1978-04-06 | 1979-10-15 | Daicel Chem Ind Ltd | Purification of acetic acid |
| JPS54155936U (cg-RX-API-DMAC7.html) * | 1978-04-21 | 1979-10-30 | ||
| US4255591A (en) * | 1978-11-20 | 1981-03-10 | Monsanto Company | Carbonylation process |
| US4241219A (en) * | 1979-07-30 | 1980-12-23 | Halcon Research And Development Corp. | Treatment of carbonylation effluent |
| DE3137782A1 (de) * | 1981-09-23 | 1983-03-31 | Hoechst Ag, 6230 Frankfurt | Verfahren zur rueckgewinnung von jodverbindungen aus dem abgas von carbonylierungsreaktionen |
| JPS6158803A (ja) * | 1984-08-27 | 1986-03-26 | Daicel Chem Ind Ltd | カルボニル化反応廃ガスからの沃素化合物の回収法 |
| DE3823645C1 (cg-RX-API-DMAC7.html) * | 1988-07-13 | 1989-11-30 | Hoechst Ag | |
| JP3377555B2 (ja) * | 1993-05-31 | 2003-02-17 | ダイセル化学工業株式会社 | カルボニル化反応生成物に含有されるヨウ素化合物の除去方法 |
| KR960006546B1 (ko) * | 1993-07-28 | 1996-05-17 | 한국과학기술연구원 | 초산에스테르의 제조 방법 |
| JPH07324055A (ja) * | 1994-04-04 | 1995-12-12 | Daicel Chem Ind Ltd | 無水酢酸及び酢酸の製造法 |
| DK136196A (da) * | 1996-11-29 | 1998-05-30 | Haldor Topsoe As | Fremgangsmåde til fremstilling af eddikesyre |
| FR2826960B1 (fr) * | 2001-07-03 | 2005-10-21 | Acetex Chimie | Procede de controle d'une production d'acide acetique et/ou d'acetate de methyle en continu |
| CN1325459C (zh) * | 2004-02-04 | 2007-07-11 | 上海吴泾化工有限公司 | 羰基化生产乙酸/醋酐中尾气轻组分的回收方法 |
| JP4564295B2 (ja) * | 2004-07-08 | 2010-10-20 | 千代田化工建設株式会社 | 気泡塔型反応器を用いた酢酸製造方法 |
| JP4597099B2 (ja) * | 2005-08-04 | 2010-12-15 | 株式会社タクマ | ガス精製システムとガス精製方法 |
| US8017802B2 (en) * | 2007-05-21 | 2011-09-13 | Celanese International Corporation | Control of impurities in reaction product of rhodium-catalyzed methanol carbonylation |
| EP2327474B1 (en) * | 2008-04-29 | 2018-01-10 | Celanese International Corporation | Methanol carbonylation system having absorber with multiple solvent options |
| US8076508B2 (en) * | 2008-12-08 | 2011-12-13 | Lyondell Chemical Technology | Preparation of acetic acid |
| CN101817737A (zh) * | 2010-03-22 | 2010-09-01 | 许昌东方化工有限公司 | 醋酸的回收方法 |
-
2011
- 2011-11-08 CN CN2011800542813A patent/CN103189125A/zh active Pending
- 2011-11-08 WO PCT/US2011/059699 patent/WO2012064689A1/en not_active Ceased
- 2011-11-08 BR BR112013011566A patent/BR112013011566A2/pt not_active IP Right Cessation
- 2011-11-08 EP EP11788270.4A patent/EP2637767B1/en active Active
- 2011-11-08 JP JP2013538818A patent/JP5969489B2/ja active Active
- 2011-11-11 TW TW100141382A patent/TWI544956B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2637767B1 (en) | 2017-04-26 |
| JP5969489B2 (ja) | 2016-08-17 |
| TW201226041A (en) | 2012-07-01 |
| EP2637767A1 (en) | 2013-09-18 |
| CN103189125A (zh) | 2013-07-03 |
| BR112013011566A2 (pt) | 2016-08-09 |
| JP2014502917A (ja) | 2014-02-06 |
| WO2012064689A1 (en) | 2012-05-18 |
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