JP2000302752A - ヒドロペルオキシド類の製造方法 - Google Patents
ヒドロペルオキシド類の製造方法Info
- Publication number
- JP2000302752A JP2000302752A JP11574499A JP11574499A JP2000302752A JP 2000302752 A JP2000302752 A JP 2000302752A JP 11574499 A JP11574499 A JP 11574499A JP 11574499 A JP11574499 A JP 11574499A JP 2000302752 A JP2000302752 A JP 2000302752A
- Authority
- JP
- Japan
- Prior art keywords
- oxidation
- hydrocarbon
- oxygen
- hydroperoxide
- hydroperoxides
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title abstract description 17
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 50
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 26
- 150000002432 hydroperoxides Chemical class 0.000 claims abstract description 23
- 230000003647 oxidation Effects 0.000 claims abstract description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000007789 gas Substances 0.000 claims abstract description 16
- -1 arylalkyl hydrocarbon Chemical class 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- VUMCUSHVMYIRMB-UHFFFAOYSA-N 1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1 VUMCUSHVMYIRMB-UHFFFAOYSA-N 0.000 claims abstract description 3
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 claims abstract description 3
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 3
- 229930007927 cymene Natural products 0.000 claims abstract description 3
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 5
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 claims description 2
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- AMBHHSBRXZAGDZ-UHFFFAOYSA-N 1-phenyl-2,3-di(propan-2-yl)benzene Chemical group CC(C)C1=CC=CC(C=2C=CC=CC=2)=C1C(C)C AMBHHSBRXZAGDZ-UHFFFAOYSA-N 0.000 claims 1
- HKTCLPBBJDIBGF-UHFFFAOYSA-N 1-phenyl-2-propan-2-ylbenzene Chemical group CC(C)C1=CC=CC=C1C1=CC=CC=C1 HKTCLPBBJDIBGF-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001336 alkenes Chemical class 0.000 abstract description 3
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 239000007858 starting material Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 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 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- QEULXXWJQAFTSN-UHFFFAOYSA-N cumene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1.CC(C)C1=CC=CC=C1 QEULXXWJQAFTSN-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical class CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- MLXMBIUVXPMUPK-UHFFFAOYSA-N 1-butan-2-yl-2-ethylbenzene Chemical compound CCC(C)C1=CC=CC=C1CC MLXMBIUVXPMUPK-UHFFFAOYSA-N 0.000 description 1
- GWLLTEXUIOFAFE-UHFFFAOYSA-N 2,6-diisopropylnaphthalene Chemical compound C1=C(C(C)C)C=CC2=CC(C(C)C)=CC=C21 GWLLTEXUIOFAFE-UHFFFAOYSA-N 0.000 description 1
- 102100024522 Bladder cancer-associated protein Human genes 0.000 description 1
- 101150110835 Blcap gene Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102100039851 DNA-directed RNA polymerases I and III subunit RPAC1 Human genes 0.000 description 1
- 101710112289 DNA-directed RNA polymerases I and III subunit RPAC1 Proteins 0.000 description 1
- 101100493740 Oryza sativa subsp. japonica BC10 gene Proteins 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C407/00—Preparation of peroxy compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11574499A JP2000302752A (ja) | 1999-04-23 | 1999-04-23 | ヒドロペルオキシド類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11574499A JP2000302752A (ja) | 1999-04-23 | 1999-04-23 | ヒドロペルオキシド類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000302752A true JP2000302752A (ja) | 2000-10-31 |
| JP2000302752A5 JP2000302752A5 (enrdf_load_stackoverflow) | 2006-02-09 |
Family
ID=14669992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11574499A Pending JP2000302752A (ja) | 1999-04-23 | 1999-04-23 | ヒドロペルオキシド類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2000302752A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005281304A (ja) * | 2004-03-04 | 2005-10-13 | Mitsubishi Chemicals Corp | クメンハイドロパーオキサイドの製造方法 |
| WO2007094504A1 (ja) * | 2006-02-16 | 2007-08-23 | Sumitomo Chemical Company, Limited | ジアルキルハイドロパーオキシベンゼンの製造方法 |
| JP2007246511A (ja) * | 2006-02-16 | 2007-09-27 | Sumitomo Chemical Co Ltd | ジアルキルハイドロパーオキシベンゼンの製造方法 |
| WO2010069586A1 (en) | 2008-12-17 | 2010-06-24 | Borealis Ag | Improving cumene oxidation |
| WO2010078934A1 (en) | 2008-12-17 | 2010-07-15 | Borealis Ag | Multistage cumene oxidation |
| EP2657192A1 (en) | 2012-04-26 | 2013-10-30 | Borealis AG | Method for reducing organic impurities in waste water |
| RU2740017C1 (ru) * | 2020-03-03 | 2020-12-30 | Общество с ограниченной ответственностью "Научно-производственное объединение ЕВРОХИМ" | Способ получения гидроперекиси кумола |
-
1999
- 1999-04-23 JP JP11574499A patent/JP2000302752A/ja active Pending
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005281304A (ja) * | 2004-03-04 | 2005-10-13 | Mitsubishi Chemicals Corp | クメンハイドロパーオキサイドの製造方法 |
| US7763755B2 (en) | 2006-02-16 | 2010-07-27 | Sumitomo Chemical Company, Limited | Method for producing dialkylhydroperoxybenzenes |
| WO2007094504A1 (ja) * | 2006-02-16 | 2007-08-23 | Sumitomo Chemical Company, Limited | ジアルキルハイドロパーオキシベンゼンの製造方法 |
| JP2007246511A (ja) * | 2006-02-16 | 2007-09-27 | Sumitomo Chemical Co Ltd | ジアルキルハイドロパーオキシベンゼンの製造方法 |
| CN102256939A (zh) * | 2008-12-17 | 2011-11-23 | 博瑞立斯有限公司 | 多级枯烯氧化 |
| CN102256939B (zh) * | 2008-12-17 | 2014-01-01 | 博瑞立斯有限公司 | 多级枯烯氧化 |
| US20110263905A1 (en) * | 2008-12-17 | 2011-10-27 | Borealis Ag | Multistage cumene oxidation |
| CN102256940A (zh) * | 2008-12-17 | 2011-11-23 | 博瑞立斯有限公司 | 改善枯烯氧化 |
| WO2010069586A1 (en) | 2008-12-17 | 2010-06-24 | Borealis Ag | Improving cumene oxidation |
| EP2379495B1 (en) * | 2008-12-17 | 2017-03-01 | Borealis AG | Improving cumene oxidation |
| US8975444B2 (en) | 2008-12-17 | 2015-03-10 | Borealis Ag | Cumene oxidation |
| WO2010078934A1 (en) | 2008-12-17 | 2010-07-15 | Borealis Ag | Multistage cumene oxidation |
| US8952202B2 (en) | 2008-12-17 | 2015-02-10 | Borealis Ag | Multistage cumene oxidation |
| CN104271512A (zh) * | 2012-04-26 | 2015-01-07 | 博瑞立斯有限公司 | 用于减少废水中的有机杂质的方法 |
| WO2013160420A1 (en) | 2012-04-26 | 2013-10-31 | Borealis Ag | Method for reducing organic impurities in waste water |
| CN104271512B (zh) * | 2012-04-26 | 2016-08-24 | 博瑞立斯有限公司 | 用于减少废水中的有机杂质的方法 |
| EP2657192A1 (en) | 2012-04-26 | 2013-10-30 | Borealis AG | Method for reducing organic impurities in waste water |
| RU2740017C1 (ru) * | 2020-03-03 | 2020-12-30 | Общество с ограниченной ответственностью "Научно-производственное объединение ЕВРОХИМ" | Способ получения гидроперекиси кумола |
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