JPS6353979B2 - - Google Patents
Info
- Publication number
- JPS6353979B2 JPS6353979B2 JP56134894A JP13489481A JPS6353979B2 JP S6353979 B2 JPS6353979 B2 JP S6353979B2 JP 56134894 A JP56134894 A JP 56134894A JP 13489481 A JP13489481 A JP 13489481A JP S6353979 B2 JPS6353979 B2 JP S6353979B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- hydrogen peroxide
- parts
- carbinol
- reaction product
- 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
Links
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 111
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 65
- 239000007795 chemical reaction product Substances 0.000 claims description 43
- 238000007254 oxidation reaction Methods 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 36
- -1 carbinol compound Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims description 15
- 229960001553 phloroglucinol Drugs 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 8
- 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 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- CWGPMZVRCXTBSZ-UHFFFAOYSA-N hydrogen peroxide 1,3,5-tri(propan-2-yl)benzene Chemical compound OO.OO.OO.CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1 CWGPMZVRCXTBSZ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- SXXLKZCNJHJYFL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,2]oxazolo[4,5-c]pyridin-5-ium-3-olate Chemical compound C1CNCC2=C1ONC2=O SXXLKZCNJHJYFL-UHFFFAOYSA-N 0.000 description 14
- 101000799461 Homo sapiens Thrombopoietin Proteins 0.000 description 14
- 102100034195 Thrombopoietin Human genes 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- GTDOPRQDTRLYAL-UHFFFAOYSA-N hydrogen peroxide;methanol Chemical compound OC.OO GTDOPRQDTRLYAL-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- PJAYOCNSYITZCZ-UHFFFAOYSA-N hydrogen peroxide 1,3,5-tri(propan-2-yl)benzene Chemical compound OO.OO.CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1 PJAYOCNSYITZCZ-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- 239000004343 Calcium peroxide Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- CFTUQVVLPNHCHP-UHFFFAOYSA-N O(O)C(C)(C)C1=CC(=CC(=C1)C(C)(O)C)C(C)(C)O Chemical compound O(O)C(C)(C)C1=CC(=CC(=C1)C(C)(O)C)C(C)(C)O CFTUQVVLPNHCHP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- LHJQIRIGXXHNLA-UHFFFAOYSA-N calcium peroxide Chemical compound [Ca+2].[O-][O-] LHJQIRIGXXHNLA-UHFFFAOYSA-N 0.000 description 1
- 235000019402 calcium peroxide Nutrition 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- ZICZNSUYUYOXMM-UHFFFAOYSA-N hydrogen peroxide 1,3,5-tri(propan-2-yl)benzene Chemical compound OO.CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1 ZICZNSUYUYOXMM-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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
-
- 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
- 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
- C07C409/12—Compounds containing six-membered aromatic rings with two alpha,alpha-dialkylmethyl hydroperoxy groups bound to carbon atoms of the same six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56134894A JPS5835135A (ja) | 1981-08-27 | 1981-08-27 | フロログルシンの製造法 |
| US06/407,159 US4469899A (en) | 1981-08-27 | 1982-08-11 | Process for producing phloroglucin |
| GB08224023A GB2104892B (en) | 1981-08-27 | 1982-08-20 | A process for producing phloroglucin |
| NL8203342A NL192616C (nl) | 1981-08-27 | 1982-08-26 | Werkwijze ter bereiding van 1,3,5-trihydroxybenzeen. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56134894A JPS5835135A (ja) | 1981-08-27 | 1981-08-27 | フロログルシンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5835135A JPS5835135A (ja) | 1983-03-01 |
| JPS6353979B2 true JPS6353979B2 (US06168655-20010102-C00055.png) | 1988-10-26 |
Family
ID=15138998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56134894A Granted JPS5835135A (ja) | 1981-08-27 | 1981-08-27 | フロログルシンの製造法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4469899A (US06168655-20010102-C00055.png) |
| JP (1) | JPS5835135A (US06168655-20010102-C00055.png) |
| GB (1) | GB2104892B (US06168655-20010102-C00055.png) |
| NL (1) | NL192616C (US06168655-20010102-C00055.png) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0244183U (US06168655-20010102-C00055.png) * | 1988-09-21 | 1990-03-27 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58150529A (ja) * | 1982-03-02 | 1983-09-07 | Mitsui Petrochem Ind Ltd | フロログルシンの製法 |
| JPS6084235A (ja) * | 1983-10-14 | 1985-05-13 | Mitsui Petrochem Ind Ltd | ｍ−ヒドロキシ置換フエノ−ル類の製法 |
| WO1987001700A1 (en) * | 1985-09-20 | 1987-03-26 | Mitsui Petrochemical Industries, Ltd. | Process for oxidizing 2,6-diisopropylnaphthalene |
| DE3607923A1 (de) * | 1986-03-11 | 1987-09-17 | Degussa | Verfahren zur herstellung substituierter trihydroxybenzole |
| JPH07108866B2 (ja) * | 1987-03-27 | 1995-11-22 | 三井石油化学工業株式会社 | ヒドロキシベンゼン類の製法 |
| US4847437A (en) * | 1987-12-22 | 1989-07-11 | Indspec Chemical Corporation | Oxidation and subsequent decomposition of dihydroperoxide |
| CN101538020B (zh) * | 2008-03-21 | 2010-11-17 | 北京化工大学 | 一种含异丙基芳烃催化氧化制过氧化氢物的方法 |
| CN104860861B (zh) * | 2015-04-01 | 2017-08-08 | 中石化上海工程有限公司 | 生产过氧化二异丙苯的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5323939A (en) * | 1976-08-18 | 1978-03-06 | Mitsui Petrochem Ind Ltd | Preparation of divalent phenols |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB751598A (en) * | 1952-12-18 | 1956-06-27 | Hooker Electrochemical Co | Meta-substituted phenols and method for their synthesis |
| US2790010A (en) * | 1952-12-18 | 1957-04-23 | Hooker Electrochemical Co | Synthesis of meta-substituted phenols |
| DD12239A1 (de) * | 1955-04-20 | 1956-10-16 | Wolfen Filmfab Veb | Verfahren zur Herstellung von Phenolen |
| JPS6024788B2 (ja) * | 1978-10-17 | 1985-06-14 | 三井化学株式会社 | 芳香族ヒドロペルオキシドの製造方法 |
| JPS567733A (en) * | 1979-06-30 | 1981-01-27 | Mitsui Petrochem Ind Ltd | Method and apparatus for preparation of phenol |
-
1981
- 1981-08-27 JP JP56134894A patent/JPS5835135A/ja active Granted
-
1982
- 1982-08-11 US US06/407,159 patent/US4469899A/en not_active Expired - Lifetime
- 1982-08-20 GB GB08224023A patent/GB2104892B/en not_active Expired
- 1982-08-26 NL NL8203342A patent/NL192616C/nl not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5323939A (en) * | 1976-08-18 | 1978-03-06 | Mitsui Petrochem Ind Ltd | Preparation of divalent phenols |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0244183U (US06168655-20010102-C00055.png) * | 1988-09-21 | 1990-03-27 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL8203342A (nl) | 1983-03-16 |
| NL192616B (nl) | 1997-07-01 |
| GB2104892A (en) | 1983-03-16 |
| US4469899A (en) | 1984-09-04 |
| NL192616C (nl) | 1997-11-04 |
| JPS5835135A (ja) | 1983-03-01 |
| GB2104892B (en) | 1985-09-04 |
