DE1163827B - Verfahren zur Herstellung von tertiaeren aliphatischen Hydroperoxyden - Google Patents
Verfahren zur Herstellung von tertiaeren aliphatischen HydroperoxydenInfo
- Publication number
- DE1163827B DE1163827B DEF31487A DEF0031487A DE1163827B DE 1163827 B DE1163827 B DE 1163827B DE F31487 A DEF31487 A DE F31487A DE F0031487 A DEF0031487 A DE F0031487A DE 1163827 B DE1163827 B DE 1163827B
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen peroxide
- reaction
- tertiary
- tertiary aliphatic
- concentration
- 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
- 238000000034 method Methods 0.000 title claims description 8
- -1 aliphatic hydroperoxides Chemical group 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 57
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 28
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 235000011007 phosphoric acid Nutrition 0.000 claims description 14
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 150000002978 peroxides Chemical class 0.000 claims description 7
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- ZWNMRZQYWRLGMM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diol Chemical compound CC(C)(O)CCC(C)(C)O ZWNMRZQYWRLGMM-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- JGBAASVQPMTVHO-UHFFFAOYSA-N 2,5-dihydroperoxy-2,5-dimethylhexane Chemical compound OOC(C)(C)CCC(C)(C)OO JGBAASVQPMTVHO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002360 explosive Substances 0.000 description 4
- 150000002432 hydroperoxides Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- LZMSJLJRUYKOQD-UHFFFAOYSA-N 2,7-dimethyloctane-2,7-diol Chemical compound CC(C)(O)CCCCC(C)(C)O LZMSJLJRUYKOQD-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HYQVJTPIWPMTLK-UHFFFAOYSA-N 1,4-dimethylcyclohexane-1,4-diol Chemical compound CC1(O)CCC(C)(O)CC1 HYQVJTPIWPMTLK-UHFFFAOYSA-N 0.000 description 1
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 1
- JPUIYNHIEXIFMV-UHFFFAOYSA-N 2,5-dimethylhexan-2-ol Chemical compound CC(C)CCC(C)(C)O JPUIYNHIEXIFMV-UHFFFAOYSA-N 0.000 description 1
- DCBZMACKXFNTBM-UHFFFAOYSA-N 2,7-dihydroperoxy-2,7-dimethyloctane Chemical compound OOC(C)(C)CCCCC(C)(C)OO DCBZMACKXFNTBM-UHFFFAOYSA-N 0.000 description 1
- SSZWOQANOUHNLV-UHFFFAOYSA-N 2-cyclohexylpropan-2-ol Chemical compound CC(C)(O)C1CCCCC1 SSZWOQANOUHNLV-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- NPHCXUPGMINOPP-UHFFFAOYSA-N 3,6-dimethyloctan-3-ol Chemical compound CCC(C)CCC(C)(O)CC NPHCXUPGMINOPP-UHFFFAOYSA-N 0.000 description 1
- WMEDSSFYIKNTNG-UHFFFAOYSA-N 3,6-dimethyloctane-3,6-diol Chemical compound CCC(C)(O)CCC(C)(O)CC WMEDSSFYIKNTNG-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000005474 detonation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82328859A | 1959-06-29 | 1959-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1163827B true DE1163827B (de) | 1964-02-27 |
Family
ID=25238324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF31487A Pending DE1163827B (de) | 1959-06-29 | 1960-06-22 | Verfahren zur Herstellung von tertiaeren aliphatischen Hydroperoxyden |
Country Status (8)
| Country | Link |
|---|---|
| CH (1) | CH383376A (en, 2012) |
| DE (1) | DE1163827B (en, 2012) |
| ES (1) | ES259029A1 (en, 2012) |
| FR (1) | FR1262829A (en, 2012) |
| GB (1) | GB904475A (en, 2012) |
| LU (1) | LU38884A1 (en, 2012) |
| MY (1) | MY6300084A (en, 2012) |
| NL (1) | NL253196A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0395803A1 (en) * | 1987-12-15 | 1990-11-07 | Nippon Oil And Fats Company, Limited | Method for producing 1,1,3,3, - tetramethylbutyl hydroperoxide |
-
0
- NL NL253196D patent/NL253196A/xx unknown
-
1960
- 1960-06-17 ES ES0259029A patent/ES259029A1/es not_active Expired
- 1960-06-17 GB GB21279/60A patent/GB904475A/en not_active Expired
- 1960-06-22 DE DEF31487A patent/DE1163827B/de active Pending
- 1960-06-24 FR FR831058A patent/FR1262829A/fr not_active Expired
- 1960-06-27 CH CH721760A patent/CH383376A/de unknown
- 1960-06-28 LU LU38884D patent/LU38884A1/xx unknown
-
1963
- 1963-12-31 MY MY196384A patent/MY6300084A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0395803A1 (en) * | 1987-12-15 | 1990-11-07 | Nippon Oil And Fats Company, Limited | Method for producing 1,1,3,3, - tetramethylbutyl hydroperoxide |
Also Published As
| Publication number | Publication date |
|---|---|
| MY6300084A (en) | 1963-12-31 |
| NL253196A (en, 2012) | |
| CH383376A (de) | 1964-10-31 |
| FR1262829A (fr) | 1961-06-05 |
| GB904475A (en) | 1962-08-29 |
| ES259029A1 (es) | 1960-10-01 |
| LU38884A1 (en, 2012) | 1960-08-29 |
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