TWI577657B - 酸溶液之純化方法 - Google Patents
酸溶液之純化方法 Download PDFInfo
- Publication number
- TWI577657B TWI577657B TW100141351A TW100141351A TWI577657B TW I577657 B TWI577657 B TW I577657B TW 100141351 A TW100141351 A TW 100141351A TW 100141351 A TW100141351 A TW 100141351A TW I577657 B TWI577657 B TW I577657B
- Authority
- TW
- Taiwan
- Prior art keywords
- stream
- hydrolysis
- carboxylic acid
- zone
- anhydride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 110
- 230000008569 process Effects 0.000 title claims description 84
- 239000002253 acid Substances 0.000 title description 13
- 238000000746 purification Methods 0.000 title description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 152
- 230000007062 hydrolysis Effects 0.000 claims description 146
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 85
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 85
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 68
- 239000003054 catalyst Substances 0.000 claims description 48
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 47
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 42
- 238000000926 separation method Methods 0.000 claims description 32
- 238000004821 distillation Methods 0.000 claims description 30
- 238000001816 cooling Methods 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 22
- 230000006315 carbonylation Effects 0.000 claims description 10
- 238000005810 carbonylation reaction Methods 0.000 claims description 10
- 230000032050 esterification Effects 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 6
- 238000004064 recycling Methods 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 description 44
- 239000000047 product Substances 0.000 description 23
- 229960000583 acetic acid Drugs 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 239000012535 impurity Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 150000001735 carboxylic acids Chemical class 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- 229910045601 alloy Inorganic materials 0.000 description 6
- 239000000956 alloy Substances 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- -1 ethylene propylene anhydride Chemical class 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 108010011485 Aspartame Proteins 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 239000000605 aspartame Substances 0.000 description 2
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 2
- 235000010357 aspartame Nutrition 0.000 description 2
- 229960003438 aspartame Drugs 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000000413 hydrolysate Substances 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 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 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- 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
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 239000004376 Sucralose Substances 0.000 description 1
- 238000002679 ablation Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical class C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 238000013178 mathematical model Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012806 monitoring device Methods 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000010457 zeolite Substances 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
- C07C51/083—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid anhydrides
- C07C51/087—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid anhydrides by hydrolysis
-
- 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
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41323410P | 2010-11-12 | 2010-11-12 | |
| US12/982,150 US9416086B2 (en) | 2010-11-12 | 2010-12-30 | Processes for purification of acid solutions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201226382A TW201226382A (en) | 2012-07-01 |
| TWI577657B true TWI577657B (zh) | 2017-04-11 |
Family
ID=46048392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW100141351A TWI577657B (zh) | 2010-11-12 | 2011-11-11 | 酸溶液之純化方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9416086B2 (https=) |
| EP (1) | EP2637996B1 (https=) |
| JP (1) | JP2014503491A (https=) |
| CN (2) | CN104591995A (https=) |
| BR (1) | BR112013011581A2 (https=) |
| TW (1) | TWI577657B (https=) |
| WO (1) | WO2012074628A1 (https=) |
Families Citing this family (6)
| 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 |
| CN106660925B (zh) | 2014-08-19 | 2021-05-11 | 索尔维阿塞托有限公司 | 用于回收羧酸的方法和木材处理方法 |
| US9908835B2 (en) | 2015-11-13 | 2018-03-06 | Celanese International Corporation | Processes for purifying acetic and hydrating anhydride |
| CN108368018B (zh) * | 2016-03-01 | 2022-01-21 | 株式会社大赛璐 | 乙酸制造方法 |
| CN107973712B (zh) * | 2017-11-28 | 2023-09-12 | 天津渤化永利化工股份有限公司 | 一种提高丙酸产量的系统及方法 |
| CN110922328B (zh) * | 2019-12-12 | 2022-11-08 | 万华化学集团股份有限公司 | 一种异辛酸粗产品中重组分的处理方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2423079A1 (de) * | 1974-05-13 | 1975-11-27 | Hoechst Ag | Verfahren zur reinigung von essigsaeure |
| CN1538946A (zh) * | 2001-08-07 | 2004-10-20 | �����ɷ� | 联合制备甲酸和具有至少两个碳原子的羧酸和/或其衍生物的灵活方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2429643A (en) * | 1939-08-11 | 1947-10-28 | Joseph G Denny Jr | Art of esterification |
| US3125551A (en) * | 1959-03-09 | 1964-03-17 | xlesterifying p polyoxymethylene glycol toth | |
| JPS4830254B1 (https=) * | 1969-02-27 | 1973-09-18 | ||
| JPS4830254A (https=) | 1971-08-20 | 1973-04-21 | ||
| NZ203226A (en) | 1982-02-13 | 1985-08-30 | Bp Chemical Ltd | Production of acetic anhydride from methanol and carbon monoxide |
| JPS58138383A (ja) * | 1982-02-13 | 1983-08-17 | Nippon Shinyaku Co Ltd | 生理活性物質の製法 |
| DE3823645C1 (https=) | 1988-07-13 | 1989-11-30 | Hoechst Ag | |
| US5175362A (en) * | 1991-05-29 | 1992-12-29 | Eastman Kodak Company | Recovery of acetyl values from ethylidene diacetate |
| JPH0830254A (ja) * | 1994-07-20 | 1996-02-02 | Hitachi Ltd | 表示効果発生回路 |
| GB9802027D0 (en) | 1998-01-31 | 1998-03-25 | Bp Chem Int Ltd | Chemical process |
| US7820856B2 (en) * | 2005-02-09 | 2010-10-26 | Mitsubishi Rayon Co., Ltd. | Process for producing α,β-unsaturated carboxylic acid |
-
2010
- 2010-12-30 US US12/982,150 patent/US9416086B2/en active Active
-
2011
- 2011-10-26 WO PCT/US2011/057785 patent/WO2012074628A1/en not_active Ceased
- 2011-10-26 CN CN201410759812.4A patent/CN104591995A/zh active Pending
- 2011-10-26 EP EP11827782.1A patent/EP2637996B1/en active Active
- 2011-10-26 BR BR112013011581A patent/BR112013011581A2/pt not_active IP Right Cessation
- 2011-10-26 JP JP2013538764A patent/JP2014503491A/ja active Pending
- 2011-10-26 CN CN201180054361.9A patent/CN103201246B/zh active Active
- 2011-11-11 TW TW100141351A patent/TWI577657B/zh active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2423079A1 (de) * | 1974-05-13 | 1975-11-27 | Hoechst Ag | Verfahren zur reinigung von essigsaeure |
| CN1538946A (zh) * | 2001-08-07 | 2004-10-20 | �����ɷ� | 联合制备甲酸和具有至少两个碳原子的羧酸和/或其衍生物的灵活方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR112013011581A2 (pt) | 2016-08-09 |
| EP2637996A1 (en) | 2013-09-18 |
| JP2014503491A (ja) | 2014-02-13 |
| CN103201246A (zh) | 2013-07-10 |
| WO2012074628A1 (en) | 2012-06-07 |
| US20120123160A1 (en) | 2012-05-17 |
| CN104591995A (zh) | 2015-05-06 |
| CN103201246B (zh) | 2016-04-06 |
| US9416086B2 (en) | 2016-08-16 |
| TW201226382A (en) | 2012-07-01 |
| EP2637996B1 (en) | 2018-02-28 |
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