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 US7141703B2 (en) | 2003-02-14 | 2004-01-21 | Process for producing phenol and ketone using neutralizing base |
| US10/761,641 | 2004-01-21 | ||
| 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 (enExample) | 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 (enExample) |
| EP (1) | EP1594838A1 (enExample) |
| JP (1) | JP4912870B2 (enExample) |
| KR (1) | KR20050097550A (enExample) |
| BR (1) | BRPI0407404A (enExample) |
| MY (1) | MY139447A (enExample) |
| TW (1) | TW200508188A (enExample) |
| WO (1) | WO2004074241A1 (enExample) |
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 |
| US7446232B2 (en) * | 2006-08-03 | 2008-11-04 | Exxonmobil Chemical Patents Inc. | Process for oxidizing alkylaromatic compounds |
| US8581016B2 (en) * | 2006-11-21 | 2013-11-12 | Mitsui Chemicals, Inc. | Process for producing alkylated aromatic compound and process for producing phenol |
| TW200846312A (en) * | 2007-02-22 | 2008-12-01 | Exxonmobil Chem Patents Inc | Oxidation of sec-butylbenzene and production of phenol and methyl ethyl ketone |
| ATE509898T1 (de) | 2007-02-23 | 2011-06-15 | Mitsui Chemicals Inc | Verfahren zur herstellung einer alkylierten aromatischen verbindung |
| CN101687784B (zh) * | 2007-08-22 | 2014-11-12 | 埃克森美孚化学专利公司 | 烃的氧化 |
| US8658836B2 (en) * | 2007-10-31 | 2014-02-25 | Exxonmobil Chemical Patents Inc. | Oxidation of hydrocarbons |
| WO2011031374A2 (en) | 2009-08-28 | 2011-03-17 | Exxonmobil Chemical Patents Inc. | Oxidation of hydrocarbons |
| JP2011500816A (ja) * | 2007-10-31 | 2011-01-06 | エクソンモービル・ケミカル・パテンツ・インク | 炭化水素の酸化 |
| KR101242254B1 (ko) | 2008-06-10 | 2013-03-11 | 미쓰이 가가쿠 가부시키가이샤 | 알킬화 방향족 화합물의 제조방법 및 페놀의 제조방법 |
| JP2011525195A (ja) * | 2008-08-26 | 2011-09-15 | エクソンモービル・ケミカル・パテンツ・インク | アルキルベンゼンヒドロペルオキシドの製造方法 |
| WO2010042273A1 (en) * | 2008-10-10 | 2010-04-15 | Exxonmobil Chemical Patents Inc. | Oxidation of hydrocarbons |
| KR101320163B1 (ko) * | 2008-10-23 | 2013-10-23 | 미쓰이 가가쿠 가부시키가이샤 | 알킬화 방향족 화합물의 제조 방법, 쿠멘의 제조 방법 및 페놀의 제조 방법 |
| CN102227405A (zh) | 2008-12-15 | 2011-10-26 | 埃克森美孚化学专利公司 | 烷基芳族化合物的氧化 |
| JP5345203B2 (ja) | 2009-03-19 | 2013-11-20 | 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 |
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 (enExample) * | 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 |
| DE2300903A1 (de) | 1972-01-10 | 1973-08-02 | Union Carbide Corp | Verfahren zur herstellung von butylbenzolhydroperoxid und dessen verwendung zur herstellung von phenol, acetophenon und methylaethylketon |
| 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 (enExample) * | 1991-12-26 | 1994-07-01 | Sumitomo Chemical Co | |
| TW237445B (enExample) * | 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 |
| CN1227202C (zh) | 1998-09-04 | 2005-11-16 | 伊拉国际有限责任公司 | 苯酚和丙酮生产的高选择性方法 |
| ES2247191T3 (es) * | 2000-12-27 | 2006-03-01 | Shell Internationale Research Maatschappij B.V. | Procedimiento para preparar hidroperoxidos organicos con una cantidad reducida de contaminantes. |
| 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 BR BRPI0407404-1A patent/BRPI0407404A/pt not_active IP Right Cessation
- 2004-02-11 WO PCT/US2004/004010 patent/WO2004074241A1/en not_active Ceased
- 2004-02-11 TW TW093103185A patent/TW200508188A/zh unknown
- 2004-02-11 KR KR1020057014920A patent/KR20050097550A/ko not_active Ceased
- 2004-02-11 JP JP2006503496A patent/JP4912870B2/ja not_active Expired - Fee Related
- 2004-02-11 MY MYPI20040415A patent/MY139447A/en unknown
- 2004-02-11 EP EP04710252A patent/EP1594838A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0407404A (pt) | 2006-02-21 |
| WO2004074241A1 (en) | 2004-09-02 |
| US20040162448A1 (en) | 2004-08-19 |
| TW200508188A (en) | 2005-03-01 |
| US7141703B2 (en) | 2006-11-28 |
| KR20050097550A (ko) | 2005-10-07 |
| JP2006517968A (ja) | 2006-08-03 |
| EP1594838A1 (en) | 2005-11-16 |
| MY139447A (en) | 2009-10-30 |
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Legal Events
| Date | Code | Title | Description |
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| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070122 |
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