TWI513684B - 粗製乙醯基類混合物之精煉方法 - Google Patents
粗製乙醯基類混合物之精煉方法 Download PDFInfo
- Publication number
- TWI513684B TWI513684B TW100141381A TW100141381A TWI513684B TW I513684 B TWI513684 B TW I513684B TW 100141381 A TW100141381 A TW 100141381A TW 100141381 A TW100141381 A TW 100141381A TW I513684 B TWI513684 B TW I513684B
- Authority
- TW
- Taiwan
- Prior art keywords
- distillation column
- torr
- column
- iodine
- containing compound
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 62
- 238000000034 method Methods 0.000 title claims description 45
- 238000007670 refining Methods 0.000 title claims description 7
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 title description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 167
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 167
- 238000004821 distillation Methods 0.000 claims description 95
- 150000001875 compounds Chemical class 0.000 claims description 69
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 63
- 229910052740 iodine Inorganic materials 0.000 claims description 63
- 239000011630 iodine Substances 0.000 claims description 62
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 claims description 45
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 14
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 14
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- -1 acetamino group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 11
- 230000006315 carbonylation Effects 0.000 description 8
- 238000005810 carbonylation reaction Methods 0.000 description 8
- 239000011269 tar Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 7
- 125000004018 acid anhydride group Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000012856 packing Methods 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 150000002497 iodine compounds Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- GELJRMXFVDEVLN-UHFFFAOYSA-N 1,1-diiodopropane Chemical compound CCC(I)I GELJRMXFVDEVLN-UHFFFAOYSA-N 0.000 description 1
- WEFSXBPMNKAUDL-UHFFFAOYSA-N 1-iodopropan-2-one Chemical compound CC(=O)CI WEFSXBPMNKAUDL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- LEKJTGQWLAUGQA-UHFFFAOYSA-N acetyl iodide Chemical compound CC(I)=O LEKJTGQWLAUGQA-UHFFFAOYSA-N 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical group CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/573—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41322410P | 2010-11-12 | 2010-11-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201226385A TW201226385A (en) | 2012-07-01 |
| TWI513684B true TWI513684B (zh) | 2015-12-21 |
Family
ID=45094237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW100141381A TWI513684B (zh) | 2010-11-12 | 2011-11-11 | 粗製乙醯基類混合物之精煉方法 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP2637998B1 (enExample) |
| JP (1) | JP2014500255A (enExample) |
| CN (1) | CN103180285B (enExample) |
| BR (1) | BR112013011438A2 (enExample) |
| TW (1) | TWI513684B (enExample) |
| WO (1) | WO2012064832A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9415366B2 (en) * | 2012-12-31 | 2016-08-16 | Eastman Chemical Company | Systems and methods for processing variable acetyl streams |
| US10428004B2 (en) | 2017-01-18 | 2019-10-01 | Daicel Corporation | Method for producing acetic acid |
| KR102255683B1 (ko) * | 2017-01-18 | 2021-05-26 | 주식회사 다이셀 | 아세트산의 제조 방법 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0087870A1 (en) * | 1982-02-13 | 1983-09-07 | BP Chemicals Limited | Process for the production of acetic anhydride and acetic acid |
| WO1995032938A1 (en) * | 1994-05-31 | 1995-12-07 | Eastman Chemical Company | Process for the removal of iodine from acetyl compounds |
| CN101384535A (zh) * | 2005-12-21 | 2009-03-11 | 英国石油化学品有限公司 | 羰基化方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3927078A (en) | 1972-08-21 | 1975-12-16 | Chevron Res | Methylene and oxymethylene bis-ester production |
| US4559183A (en) | 1973-09-04 | 1985-12-17 | The Halcon Sd Group, Inc. | Preparation of carboxylic acid anhydrides |
| DE2450965C2 (de) | 1974-10-26 | 1983-06-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung von Essigsäureanhydrid |
| US4115444A (en) | 1975-03-10 | 1978-09-19 | Halcon International, Inc. | Process for preparing carboxylic acid anhydrides |
| DE2836084A1 (de) | 1978-08-17 | 1980-03-06 | Hoechst Ag | Verfahren zur herstellung von essigsaeureanhydrid |
| US4252741A (en) | 1978-10-06 | 1981-02-24 | Halcon Research & Development Corp. | Carbonylation with Group VIII noble metal catalysts |
| US4374070A (en) | 1980-11-21 | 1983-02-15 | Eastman Kodak Company | Preparation of acetic anhydride |
| NZ203225A (en) | 1982-02-13 | 1985-01-31 | Bp Chem Int Ltd | Coproduction of monocarboxylic acids and anhydrides |
| US4435595A (en) | 1982-04-26 | 1984-03-06 | Eastman Kodak Company | Reactive distillation process for the production of methyl acetate |
| US5003104A (en) | 1987-03-03 | 1991-03-26 | Bp Chemicals Limited | Carbonylation process and catalyst |
| DE69108567T2 (de) | 1990-12-20 | 1995-08-03 | Eastman Chem Co | Kontinuierliches verfahren zur herstellung von essigsäureanhydrid oder einer mischung von essigsäureanhydrid und essigsäure. |
| US5300198A (en) * | 1993-04-05 | 1994-04-05 | Eastman Kodak Company | Process for the separation of ethylidene diacetate from acetic anhydride |
| JPH07324055A (ja) * | 1994-04-04 | 1995-12-12 | Daicel Chem Ind Ltd | 無水酢酸及び酢酸の製造法 |
| US5554790A (en) * | 1994-04-04 | 1996-09-10 | Daicel Chemical Industries, Ltd. | Process for producing acetic anhydride and acetic acid |
| US5922911A (en) | 1998-04-24 | 1999-07-13 | Eastman Chemical Company | Process for the manufacture of acetic anhydride |
-
2011
- 2011-11-09 WO PCT/US2011/059958 patent/WO2012064832A1/en not_active Ceased
- 2011-11-09 CN CN201180054078.6A patent/CN103180285B/zh active Active
- 2011-11-09 BR BR112013011438A patent/BR112013011438A2/pt not_active IP Right Cessation
- 2011-11-09 JP JP2013538844A patent/JP2014500255A/ja active Pending
- 2011-11-09 EP EP11791113.1A patent/EP2637998B1/en active Active
- 2011-11-11 TW TW100141381A patent/TWI513684B/zh active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0087870A1 (en) * | 1982-02-13 | 1983-09-07 | BP Chemicals Limited | Process for the production of acetic anhydride and acetic acid |
| WO1995032938A1 (en) * | 1994-05-31 | 1995-12-07 | Eastman Chemical Company | Process for the removal of iodine from acetyl compounds |
| CN101384535A (zh) * | 2005-12-21 | 2009-03-11 | 英国石油化学品有限公司 | 羰基化方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012064832A1 (en) | 2012-05-18 |
| EP2637998A1 (en) | 2013-09-18 |
| TW201226385A (en) | 2012-07-01 |
| CN103180285A (zh) | 2013-06-26 |
| JP2014500255A (ja) | 2014-01-09 |
| BR112013011438A2 (pt) | 2016-08-09 |
| CN103180285B (zh) | 2016-02-03 |
| EP2637998B1 (en) | 2018-08-22 |
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