CN100402482C - 芳香羧酸的制备方法 - Google Patents
芳香羧酸的制备方法 Download PDFInfo
- Publication number
- CN100402482C CN100402482C CNB2004800045914A CN200480004591A CN100402482C CN 100402482 C CN100402482 C CN 100402482C CN B2004800045914 A CNB2004800045914 A CN B2004800045914A CN 200480004591 A CN200480004591 A CN 200480004591A CN 100402482 C CN100402482 C CN 100402482C
- Authority
- CN
- China
- Prior art keywords
- acetate
- carboxylic acid
- aromatic carboxylic
- methyl acetate
- solvent
- 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 - Lifetime
Links
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000004519 manufacturing process Methods 0.000 title abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 86
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 63
- 239000002904 solvent Substances 0.000 claims abstract description 60
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 58
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000007788 liquid Substances 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 46
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 44
- 238000011084 recovery Methods 0.000 claims abstract description 35
- 238000000926 separation method Methods 0.000 claims abstract description 29
- 238000002425 crystallisation Methods 0.000 claims abstract description 25
- 239000002002 slurry Substances 0.000 claims abstract description 24
- 238000001035 drying Methods 0.000 claims abstract description 13
- 239000007791 liquid phase Substances 0.000 claims abstract description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 65
- 230000003647 oxidation Effects 0.000 claims description 37
- 239000007789 gas Substances 0.000 claims description 30
- 239000002912 waste gas Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 28
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 14
- 230000001590 oxidative effect Effects 0.000 claims description 13
- 238000010521 absorption reaction Methods 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000006096 absorbing agent Substances 0.000 claims description 5
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 4
- 230000008025 crystallization Effects 0.000 abstract description 14
- -1 terephthalic acid Chemical compound 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 description 14
- 238000005984 hydrogenation reaction Methods 0.000 description 11
- 238000000746 purification Methods 0.000 description 9
- 239000012452 mother liquor Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229930194542 Keto Natural products 0.000 description 5
- 125000000468 ketone group Chemical group 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000567 combustion gas Substances 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux 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
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
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)
Abstract
Description
Claims (13)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP044121/2003 | 2003-02-21 | ||
JP2003044121 | 2003-02-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1751015A CN1751015A (zh) | 2006-03-22 |
CN100402482C true CN100402482C (zh) | 2008-07-16 |
Family
ID=32905446
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2004800045914A Expired - Lifetime CN100402482C (zh) | 2003-02-21 | 2004-02-13 | 芳香羧酸的制备方法 |
Country Status (3)
Country | Link |
---|---|
CN (1) | CN100402482C (zh) |
AU (1) | AU2004213274A1 (zh) |
WO (1) | WO2004074231A1 (zh) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7888530B2 (en) | 2004-09-02 | 2011-02-15 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
US7897810B2 (en) | 2004-09-02 | 2011-03-01 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
US20070203359A1 (en) | 2006-03-01 | 2007-08-30 | Philip Edward Gibson | Versatile oxidation byproduct purge process |
US7863481B2 (en) | 2006-03-01 | 2011-01-04 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
US7897808B2 (en) | 2006-03-01 | 2011-03-01 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
US7880032B2 (en) | 2006-03-01 | 2011-02-01 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
CN100368370C (zh) * | 2006-03-29 | 2008-02-13 | 中国石化仪征化纤股份有限公司 | 对二甲苯氧化母液中悬浮物的回收系统装置 |
CN101914003A (zh) * | 2010-07-02 | 2010-12-15 | 逸盛大化石化有限公司 | 一种烷基芳香烃液相催化氧化生产芳香族羧酸的方法 |
GB201417621D0 (en) * | 2014-10-06 | 2014-11-19 | Invista Tech Sarl | Production of an aromatic dicarboxylic acid |
GB201417735D0 (en) * | 2014-10-07 | 2014-11-19 | Invista Tech Sarl | Production of an aromatic dicarboxylic acid |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4562285A (en) * | 1976-12-30 | 1985-12-31 | Mitsubishi Chemical Industries Limited | Process for producing terephthalic acid |
US6143925A (en) * | 1998-06-05 | 2000-11-07 | Mitsui Chemicals, Inc. | Process for producing aromatic carboxylic acid |
CN1374937A (zh) * | 1999-09-21 | 2002-10-16 | 纳幕尔杜邦公司 | 具有改进的前体、溶剂和乙酸甲酯回收的生产纯对苯二甲酸的方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5384932A (en) * | 1976-12-30 | 1978-07-26 | Mitsubishi Chem Ind Ltd | Preparation of terephthalic acid |
JP2000072714A (ja) * | 1998-08-24 | 2000-03-07 | Mitsui Chemicals Inc | 芳香族カルボン酸の製造方法 |
-
2004
- 2004-02-13 CN CNB2004800045914A patent/CN100402482C/zh not_active Expired - Lifetime
- 2004-02-13 AU AU2004213274A patent/AU2004213274A1/xx active Pending
- 2004-02-13 WO PCT/JP2004/001549 patent/WO2004074231A1/ja active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4562285A (en) * | 1976-12-30 | 1985-12-31 | Mitsubishi Chemical Industries Limited | Process for producing terephthalic acid |
US6143925A (en) * | 1998-06-05 | 2000-11-07 | Mitsui Chemicals, Inc. | Process for producing aromatic carboxylic acid |
CN1374937A (zh) * | 1999-09-21 | 2002-10-16 | 纳幕尔杜邦公司 | 具有改进的前体、溶剂和乙酸甲酯回收的生产纯对苯二甲酸的方法 |
Also Published As
Publication number | Publication date |
---|---|
AU2004213274A1 (en) | 2004-09-02 |
WO2004074231A1 (ja) | 2004-09-02 |
CN1751015A (zh) | 2006-03-22 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CP01 | Change in the name or title of a patent holder |
Address after: Tokyo, Japan Patentee after: MITSUBISHI CHEMICAL Corp. Address before: Tokyo, Japan Patentee before: MITSUBISHI RAYON Co.,Ltd. |
|
CP01 | Change in the name or title of a patent holder | ||
TR01 | Transfer of patent right |
Effective date of registration: 20170926 Address after: Tokyo, Japan Patentee after: MITSUBISHI RAYON Co.,Ltd. Address before: Tokyo, Japan (Tokyo four, 14, 1) Patentee before: MITSUBISHI CHEMICAL Corp. |
|
TR01 | Transfer of patent right | ||
CX01 | Expiry of patent term |
Granted publication date: 20080716 |
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CX01 | Expiry of patent term |