JP4912870B2 - アルキルベンゼンヒドロペルオキシドの製造方法 - Google Patents
アルキルベンゼンヒドロペルオキシドの製造方法 Download PDFInfo
- Publication number
- JP4912870B2 JP4912870B2 JP2006503496A JP2006503496A JP4912870B2 JP 4912870 B2 JP4912870 B2 JP 4912870B2 JP 2006503496 A JP2006503496 A JP 2006503496A JP 2006503496 A JP2006503496 A JP 2006503496A JP 4912870 B2 JP4912870 B2 JP 4912870B2
- Authority
- JP
- Japan
- Prior art keywords
- oxidation
- alkali metal
- hydroperoxide
- metal base
- amount
- 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 - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- -1 alkylbenzene hydroperoxide Chemical class 0.000 title claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 125
- 230000003647 oxidation Effects 0.000 claims description 121
- RWGFKTVRMDUZSP-UHFFFAOYSA-N isopropyl-benzene Natural products CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 43
- 239000002585 base Substances 0.000 claims description 38
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 26
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical group 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 41
- 239000000203 mixture Substances 0.000 description 33
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
- 230000003472 neutralizing effect Effects 0.000 description 20
- 229910021529 ammonia Inorganic materials 0.000 description 17
- 238000002474 experimental method Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 description 13
- 239000006227 byproduct Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 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 9
- 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 7
- 235000019253 formic acid Nutrition 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- KHADDDTZDWSVIZ-UHFFFAOYSA-N butan-2-ylbenzene;hydrogen peroxide Chemical compound OO.CCC(C)C1=CC=CC=C1 KHADDDTZDWSVIZ-UHFFFAOYSA-N 0.000 description 4
- 239000002574 poison Substances 0.000 description 4
- 231100000614 poison Toxicity 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 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 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FTZBYXCNXOPJEL-UHFFFAOYSA-N 2-methyl-1-phenylbutan-2-ol Chemical compound CCC(C)(O)CC1=CC=CC=C1 FTZBYXCNXOPJEL-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 230000000674 effect on sodium Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- 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
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
- C07C409/10—Cumene hydroperoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44752603P | 2003-02-14 | 2003-02-14 | |
| US60/447,526 | 2003-02-14 | ||
| US10/761,641 | 2004-01-21 | ||
| US10/761,641 US7141703B2 (en) | 2003-02-14 | 2004-01-21 | Process for producing phenol and ketone using neutralizing base |
| PCT/US2004/004010 WO2004074241A1 (en) | 2003-02-14 | 2004-02-11 | Process for producing alkylbenzene hydroperoxides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006517968A JP2006517968A (ja) | 2006-08-03 |
| JP2006517968A5 JP2006517968A5 (https=) | 2011-04-14 |
| JP4912870B2 true JP4912870B2 (ja) | 2012-04-11 |
Family
ID=32853507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006503496A Expired - Fee Related JP4912870B2 (ja) | 2003-02-14 | 2004-02-11 | アルキルベンゼンヒドロペルオキシドの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7141703B2 (https=) |
| EP (1) | EP1594838A1 (https=) |
| JP (1) | JP4912870B2 (https=) |
| KR (1) | KR20050097550A (https=) |
| BR (1) | BRPI0407404A (https=) |
| MY (1) | MY139447A (https=) |
| TW (1) | TW200508188A (https=) |
| WO (1) | WO2004074241A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007106747A (ja) * | 2005-09-15 | 2007-04-26 | Sumitomo Chemical Co Ltd | アルキルベンゼンハイドロパーオキサイドの製造方法 |
| US7326815B2 (en) * | 2005-12-27 | 2008-02-05 | Exxonmobil Chemical Patents Inc. | Selective oxidation of alkylbenzenes |
| WO2008018972A2 (en) * | 2006-08-03 | 2008-02-14 | Exxonmobil Chemical Patents Inc. | Process for oxidizing alkylaromatic compounds |
| CN101541711B (zh) | 2006-11-21 | 2013-02-13 | 三井化学株式会社 | 烷基化芳香族化合物的制造方法以及苯酚的制造方法 |
| TW200846312A (en) * | 2007-02-22 | 2008-12-01 | Exxonmobil Chem Patents Inc | Oxidation of sec-butylbenzene and production of phenol and methyl ethyl ketone |
| JP5072951B2 (ja) | 2007-02-23 | 2012-11-14 | 三井化学株式会社 | アルキル化芳香族化合物の製造方法 |
| WO2009025939A2 (en) * | 2007-08-22 | 2009-02-26 | Exxonmobil Chemical Patents Inc. | Oxidation of hydrocarbons |
| WO2009058531A1 (en) * | 2007-10-31 | 2009-05-07 | Exxonmobil Chemical Patents Inc. | Oxidation of hydrocarbons |
| US8658839B2 (en) * | 2007-10-31 | 2014-02-25 | Exxonmobil Chemical Patents Inc. | Oxidation of hydrocarbons |
| JP5334969B2 (ja) * | 2008-06-10 | 2013-11-06 | 三井化学株式会社 | アルキル化芳香族化合物の製造方法およびフェノールの製造方法 |
| EP2344436A1 (en) * | 2008-08-26 | 2011-07-20 | ExxonMobil Chemical Patents Inc. | Process for producing alkylbenzene hydroperoxides |
| CN102177120B (zh) * | 2008-10-10 | 2015-01-28 | 埃克森美孚化学专利公司 | 烃的氧化 |
| WO2010047364A1 (ja) * | 2008-10-23 | 2010-04-29 | 三井化学株式会社 | アルキル化芳香族化合物の製造方法、クメンの製造方法およびフェノールの製造方法 |
| CN104529853A (zh) | 2008-12-15 | 2015-04-22 | 埃克森美孚化学专利公司 | 烷基芳族化合物的氧化 |
| WO2010106967A1 (ja) | 2009-03-19 | 2010-09-23 | 三井化学株式会社 | アルキル化芳香族化合物の製造方法およびフェノールの製造方法 |
| CN106117099A (zh) | 2009-08-28 | 2016-11-16 | 埃克森美孚化学专利公司 | 烃的氧化 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2632773A (en) | 1947-04-01 | 1953-03-24 | Hercules Powder Co Ltd | Manufacture of peroxidic compounds |
| US3187055A (en) * | 1948-03-19 | 1965-06-01 | Hercules Powder Co Ltd | Manufacture of peroxidic compounds |
| US2632026A (en) | 1950-02-18 | 1953-03-17 | Hercules Powder Co Ltd | Oxidation of aromatic hydrocarbons |
| US2757209A (en) | 1951-04-26 | 1956-07-31 | Allied Chem & Dye Corp | Recovery of phenol and alphamethylstyrene from cumene oxidation reaction mixtures |
| NL136649C (https=) * | 1966-11-03 | |||
| US3907901A (en) * | 1969-07-14 | 1975-09-23 | Allied Chem | Continuous process for preparing cumene hydroperoxide |
| US4016213A (en) * | 1971-05-03 | 1977-04-05 | Allied Chemical Corporation | Recovery of phenol, acetone and dimethyl phenyl carbinol from cumene oxidation product |
| FR2182802A1 (en) | 1972-01-10 | 1973-12-14 | Union Carbide Corp | Sec butylbenzolhydroperoxide prepn - with subsequent prodn of phenol and methylethyl ketone |
| US4358618A (en) | 1981-06-22 | 1982-11-09 | Allied Corporation | Decomposition of cumene oxidation product |
| US4431849A (en) * | 1981-10-21 | 1984-02-14 | The Goodyear Tire & Rubber Company | Process for preparing a methyl phenol |
| JPH0635407B2 (ja) * | 1985-02-21 | 1994-05-11 | 三井石油化学工業株式会社 | ２，６−ジイソプロピルナフタレンの酸化方法 |
| JP2686490B2 (ja) * | 1988-09-05 | 1997-12-08 | 三菱化学株式会社 | クメンヒドロペルオキシドの精製方法 |
| US4950794A (en) | 1989-05-24 | 1990-08-21 | Arco Chemical Technology, Inc. | Ethylbenzene oxidation |
| JP3061394B2 (ja) | 1990-04-02 | 2000-07-10 | 三井化学株式会社 | クメンハイドロパーオキサイドの製造方法 |
| TW226011B (https=) * | 1991-12-26 | 1994-07-01 | Sumitomo Chemical Co | |
| TW237445B (https=) * | 1992-07-07 | 1995-01-01 | Sumitomo Chemical Co | |
| US5254751A (en) | 1992-09-14 | 1993-10-19 | General Electric Company | Method for the decomposition of cumene hydroperoxide by acidic catalyst to phenol and acetone |
| RU2108318C1 (ru) * | 1994-03-01 | 1998-04-10 | Закошанский Владимир Михайлович | СПОСОБ ПОЛУЧЕНИЯ ФЕНОЛА, АЦЕТОНА И α МЕТИЛСТИРОЛА |
| US5767322A (en) * | 1996-06-27 | 1998-06-16 | General Electric Company | Cumene oxidation process |
| JP3391644B2 (ja) * | 1996-12-19 | 2003-03-31 | 住友化学工業株式会社 | ハイドロパーオキシドの抽出方法 |
| US6077977A (en) | 1998-06-01 | 2000-06-20 | General Electric Company | Method for preparing hydroperoxides by oxygenation |
| WO2000014042A1 (en) | 1998-09-04 | 2000-03-16 | Illa International L.L.C. | High selective method of phenol and acetone production |
| JP3939655B2 (ja) * | 2000-12-27 | 2007-07-04 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | 汚染物質の含有量を低減させた有機ヒドロペルオキシドの調製方法 |
| US6465695B1 (en) * | 2001-07-27 | 2002-10-15 | General Electric Company | Method and system for manufacturing cumene hydroperoxide |
| US6486365B1 (en) * | 2002-04-04 | 2002-11-26 | General Electric Company | Production and purification of phenol: hydroxyacetone removal by hydrotalcite |
-
2004
- 2004-01-21 US US10/761,641 patent/US7141703B2/en not_active Expired - Fee Related
- 2004-02-11 JP JP2006503496A patent/JP4912870B2/ja not_active Expired - Fee Related
- 2004-02-11 TW TW093103185A patent/TW200508188A/zh unknown
- 2004-02-11 WO PCT/US2004/004010 patent/WO2004074241A1/en not_active Ceased
- 2004-02-11 KR KR1020057014920A patent/KR20050097550A/ko not_active Ceased
- 2004-02-11 EP EP04710252A patent/EP1594838A1/en not_active Withdrawn
- 2004-02-11 MY MYPI20040415A patent/MY139447A/en unknown
- 2004-02-11 BR BRPI0407404-1A patent/BRPI0407404A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1594838A1 (en) | 2005-11-16 |
| US20040162448A1 (en) | 2004-08-19 |
| MY139447A (en) | 2009-10-30 |
| US7141703B2 (en) | 2006-11-28 |
| KR20050097550A (ko) | 2005-10-07 |
| TW200508188A (en) | 2005-03-01 |
| BRPI0407404A (pt) | 2006-02-21 |
| WO2004074241A1 (en) | 2004-09-02 |
| JP2006517968A (ja) | 2006-08-03 |
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