ES2440468T3 - Procedimiento para la eliminación de acetol a partir de fenol - Google Patents
Procedimiento para la eliminación de acetol a partir de fenol Download PDFInfo
- Publication number
- ES2440468T3 ES2440468T3 ES05712667.4T ES05712667T ES2440468T3 ES 2440468 T3 ES2440468 T3 ES 2440468T3 ES 05712667 T ES05712667 T ES 05712667T ES 2440468 T3 ES2440468 T3 ES 2440468T3
- Authority
- ES
- Spain
- Prior art keywords
- phenol
- acetol
- mbf
- stream
- treatment
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 81
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 26
- 229920005989 resin Polymers 0.000 claims abstract description 31
- 239000011347 resin Substances 0.000 claims abstract description 31
- 230000002378 acidificating effect Effects 0.000 claims abstract description 29
- 238000004821 distillation Methods 0.000 claims abstract description 24
- 238000009835 boiling Methods 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- KCZQNAOFWQGLCN-UHFFFAOYSA-N 5-methyl-1-benzofuran Chemical compound CC1=CC=C2OC=CC2=C1 KCZQNAOFWQGLCN-UHFFFAOYSA-N 0.000 claims 1
- GBGPVUAOTCNZPT-UHFFFAOYSA-N 2-Methylcumarone Chemical compound C1=CC=C2OC(C)=CC2=C1 GBGPVUAOTCNZPT-UHFFFAOYSA-N 0.000 abstract description 6
- 238000007701 flash-distillation Methods 0.000 abstract 1
- 238000011282 treatment Methods 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000013626 chemical specie Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery 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
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- ZRXHLJNBNWVNIM-UHFFFAOYSA-N 3-methyl-1-benzofuran Chemical compound C1=CC=C2C(C)=COC2=C1 ZRXHLJNBNWVNIM-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- -1 aliphatic carbonyl compounds Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- ZPAOSKLOFZWBLS-UHFFFAOYSA-N n-[3-methyl-1-(2-phenylethyl)piperidin-4-yl]-n-phenylbutanamide Chemical compound C=1C=CC=CC=1N(C(=O)CCC)C(C(C1)C)CCN1CCC1=CC=CC=C1 ZPAOSKLOFZWBLS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/04—Phenol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55623604P | 2004-03-24 | 2004-03-24 | |
| US556236P | 2004-03-24 | ||
| US915723 | 2004-08-09 | ||
| US10/915,723 US7034192B2 (en) | 2004-03-24 | 2004-08-09 | Method for removal of acetol from phenol |
| PCT/US2005/003298 WO2005102974A1 (en) | 2004-03-24 | 2005-02-03 | Method for removal of acetol from phenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2440468T3 true ES2440468T3 (es) | 2014-01-29 |
Family
ID=34960470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES05712667.4T Expired - Lifetime ES2440468T3 (es) | 2004-03-24 | 2005-02-03 | Procedimiento para la eliminación de acetol a partir de fenol |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7034192B2 (enExample) |
| EP (1) | EP1727779B1 (enExample) |
| JP (1) | JP4226054B2 (enExample) |
| KR (2) | KR20060130209A (enExample) |
| CN (1) | CN1942423B (enExample) |
| ES (1) | ES2440468T3 (enExample) |
| TW (1) | TWI266642B (enExample) |
| WO (1) | WO2005102974A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4996861B2 (ja) * | 2006-02-23 | 2012-08-08 | 三井化学株式会社 | 回収フェノール類の精製方法 |
| EP2247535B1 (en) | 2007-12-20 | 2016-03-02 | Borealis Technology Oy | Process for recovery of organic compounds from a wastewater stream |
| WO2012036822A1 (en) | 2010-09-14 | 2012-03-22 | Exxonmobil Chemical Patents Inc. | Phenol and cyclohexanone mixtures |
| KR101378274B1 (ko) * | 2010-06-08 | 2014-04-01 | 주식회사 엘지화학 | 페놀 불순물 제거 방법 |
| WO2012036827A1 (en) | 2010-09-14 | 2012-03-22 | Exxonmobil Chemical Patents Inc. | Processes for producing phenol |
| WO2012036828A1 (en) | 2010-09-14 | 2012-03-22 | Exxonmobil Chemical Patents Inc. | Processes for producing phenol |
| WO2012036819A1 (en) | 2010-09-14 | 2012-03-22 | Exxonmobil Chemical Patents Inc. | Dehydrogenation process of cyclohexanone and phenol compositions |
| US9365474B2 (en) | 2010-09-14 | 2016-06-14 | Exxonmobil Chemical Patents Inc. | Processes for producing phenol |
| US8921610B2 (en) | 2010-09-14 | 2014-12-30 | Exxonmobil Chemical Patents Inc. | Oxidation of alkylbenzenes |
| JP6074902B2 (ja) * | 2012-03-28 | 2017-02-08 | 三菱化学株式会社 | 精製フェノール系化合物の製造方法 |
| WO2018088846A1 (ko) * | 2016-11-14 | 2018-05-17 | 주식회사 엘지화학 | 페놀의 정제 방법 |
| KR102040059B1 (ko) * | 2016-11-14 | 2019-11-05 | 주식회사 엘지화학 | 페놀의 정제 방법 |
| KR102021114B1 (ko) * | 2017-01-24 | 2019-09-11 | 주식회사 엘지화학 | 페놀의 정제 방법 |
| US11578278B2 (en) | 2020-08-01 | 2023-02-14 | Honeywell International Inc. | Renewable transportation fuel process with thermal oxidation system |
| US12017984B2 (en) | 2020-08-04 | 2024-06-25 | Honeywell International Inc. | Propane/butane dehydrogenation complex with thermal oxidation system |
| US11780795B2 (en) | 2020-08-04 | 2023-10-10 | Honeywell International Inc. | Cumene-phenol complex with thermal oxidation system |
| US11578020B2 (en) | 2020-08-04 | 2023-02-14 | Honeywell International Inc. | Naphtha complex with thermal oxidation system |
| US11492306B2 (en) | 2020-09-30 | 2022-11-08 | Honeywell International Inc. | Alkylation process with thermal oxidation system |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2992169A (en) * | 1961-07-11 | Inven | ||
| US2910511A (en) * | 1956-12-10 | 1959-10-27 | Allied Chem | Processes for the purification of phenols |
| GB865677A (en) | 1958-03-04 | 1961-04-19 | Distillers Co Yeast Ltd | Purification of phenol |
| US2971893A (en) * | 1958-05-29 | 1961-02-14 | Hercules Powder Co Ltd | Phenol purification |
| US3029294A (en) * | 1959-02-27 | 1962-04-10 | Hercules Powder Co Ltd | Purification of phenol |
| GB883746A (en) | 1959-08-28 | 1961-12-06 | Distillers Co Yeast Ltd | Purification of phenol |
| GB920905A (en) | 1959-11-20 | 1963-03-13 | Shawinigan Chem Ltd | Improvements in and relating to purification of phenol |
| GB933723A (en) | 1960-05-20 | 1963-08-14 | Distillers Co Yeast Ltd | Purification of phenol |
| US3087969A (en) * | 1961-03-29 | 1963-04-30 | Dow Chemical Co | Method for purifying aromatic compounds |
| US3335070A (en) * | 1964-06-18 | 1967-08-08 | Hercules Inc | Phenol purification by base addition and plural distillation |
| GB1108327A (en) | 1964-08-05 | 1968-04-03 | Universal Oil Prod Co | Process for purifying phenols |
| GB1148907A (en) * | 1965-11-26 | 1969-04-16 | Ici Ltd | Purification of phenol |
| GB1171854A (en) | 1966-03-24 | 1969-11-26 | Sir Soc Italiana Resine Spa | Method of Purifying Phenol. |
| DE1668952A1 (de) | 1968-01-13 | 1969-11-27 | Phenolchemie Gmbh | Verfahren zur Gewinnung von Reinphenolen aus Rohphenolen,die bei der Spaltung von Hydroperoxiden alkylaromatischer Kohlenwasserstoffe erhalten worden sind |
| US3965187A (en) * | 1970-07-02 | 1976-06-22 | Allied Chemical Corporation | Hydrogenation of phenol |
| US3810946A (en) * | 1972-11-03 | 1974-05-14 | Allied Chem | Purification of phenol |
| US4251325A (en) | 1978-03-04 | 1981-02-17 | Bp Chemicals Limited | Process for the removal of hydroxyacetone from phenol |
| US4298765A (en) * | 1980-03-26 | 1981-11-03 | Allied Corporation | Purification of phenol with reduced energy consumption |
| US4334107A (en) | 1980-11-11 | 1982-06-08 | Allied Chemical Corporation | Catalytic purification of phenol |
| US4857151A (en) * | 1982-06-28 | 1989-08-15 | The Lummus Company | Phenol purification |
| IT1183331B (it) | 1985-02-08 | 1987-10-22 | Anic Spa | Procedimento per la purificazione di fenolo |
| JPH05286879A (ja) | 1992-04-03 | 1993-11-02 | Mitsui Petrochem Ind Ltd | 高純度フェノールの製造方法 |
| RU2111203C1 (ru) * | 1993-12-01 | 1998-05-20 | Закошанский Владимир Михайлович | Способ очистки фенола от органических примесей |
| US5414154A (en) * | 1994-06-06 | 1995-05-09 | Alliedsignal Inc. | Phenol with low levels of methylbenzofuran |
| DE19903414A1 (de) | 1999-01-29 | 2000-10-05 | Phenolchemie Gmbh & Co Kg | Verfahren zum Entfernen von Hydroxyaceton aus hydroxyacetonhaltigem Phenol |
| US6066767A (en) * | 1999-02-10 | 2000-05-23 | Illa International, Llc | Method of purifying cumene hydroperoxide decomposition products from hydroxyacetone and from other carbonyls |
| DE19951373A1 (de) * | 1999-10-26 | 2001-05-03 | Phenolchemie Gmbh & Co Kg | Verfahren zur Entfernung von Verunreinigungen aus Phenol mittels zumindest eines sauren Katalysators |
| US6346645B1 (en) * | 2000-04-18 | 2002-02-12 | Uop Llc | Adsorptive removal of carbonyl impurities from oxygenated organic liquids |
| US6576798B1 (en) * | 2001-11-29 | 2003-06-10 | General Electric Company | Method and system for purifying cumene hydroperoxide cleavage products |
| US6573408B1 (en) * | 2001-11-29 | 2003-06-03 | General Electric Company | System and method for purifying cumene hydroperoxide cleavage products |
| US6635789B2 (en) * | 2002-03-06 | 2003-10-21 | General Electric Company | Production and purification of phenol |
| US6486365B1 (en) * | 2002-04-04 | 2002-11-26 | General Electric Company | Production and purification of phenol: hydroxyacetone removal by hydrotalcite |
| US7205442B2 (en) | 2003-02-06 | 2007-04-17 | Shell Oil Company | Method of making high purity phenol |
| US7019180B2 (en) | 2003-02-06 | 2006-03-28 | Shell Oil Company | Method of purifying phenol |
| CN1898189A (zh) * | 2003-12-18 | 2007-01-17 | 通用电气公司 | 苯酚的纯化方法 |
-
2004
- 2004-08-09 US US10/915,723 patent/US7034192B2/en not_active Expired - Lifetime
- 2004-09-16 US US10/944,315 patent/US7002048B2/en not_active Expired - Lifetime
-
2005
- 2005-02-03 JP JP2007504949A patent/JP4226054B2/ja not_active Expired - Lifetime
- 2005-02-03 CN CN2005800089353A patent/CN1942423B/zh not_active Expired - Lifetime
- 2005-02-03 KR KR1020067018715A patent/KR20060130209A/ko not_active Ceased
- 2005-02-03 ES ES05712667.4T patent/ES2440468T3/es not_active Expired - Lifetime
- 2005-02-03 EP EP05712667.4A patent/EP1727779B1/en not_active Expired - Lifetime
- 2005-02-03 WO PCT/US2005/003298 patent/WO2005102974A1/en not_active Ceased
- 2005-02-03 KR KR1020087023910A patent/KR20080093463A/ko not_active Ceased
- 2005-02-05 TW TW094104094A patent/TWI266642B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1727779A1 (en) | 2006-12-06 |
| JP2007530539A (ja) | 2007-11-01 |
| CN1942423B (zh) | 2010-05-05 |
| TWI266642B (en) | 2006-11-21 |
| US20050215834A1 (en) | 2005-09-29 |
| KR20080093463A (ko) | 2008-10-21 |
| TW200539928A (en) | 2005-12-16 |
| WO2005102974A1 (en) | 2005-11-03 |
| CN1942423A (zh) | 2007-04-04 |
| US7034192B2 (en) | 2006-04-25 |
| JP4226054B2 (ja) | 2009-02-18 |
| KR20060130209A (ko) | 2006-12-18 |
| US20050215835A1 (en) | 2005-09-29 |
| EP1727779B1 (en) | 2013-10-09 |
| US7002048B2 (en) | 2006-02-21 |
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