DE2227529A1 - Verbessertes Verfahren zur Herstellung von aromatischen (sek.-C tief 3-tief 7-Alkyl) -hydroperoxiden - Google Patents
Verbessertes Verfahren zur Herstellung von aromatischen (sek.-C tief 3-tief 7-Alkyl) -hydroperoxidenInfo
- Publication number
- DE2227529A1 DE2227529A1 DE19722227529 DE2227529A DE2227529A1 DE 2227529 A1 DE2227529 A1 DE 2227529A1 DE 19722227529 DE19722227529 DE 19722227529 DE 2227529 A DE2227529 A DE 2227529A DE 2227529 A1 DE2227529 A1 DE 2227529A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction mixture
- zone
- oxidation
- oxygen
- oxidation zone
- 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 32
- 125000003118 aryl group Chemical group 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 8
- 150000002432 hydroperoxides Chemical class 0.000 title description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 79
- 230000003647 oxidation Effects 0.000 claims description 78
- 239000007789 gas Substances 0.000 claims description 63
- 239000011541 reaction mixture Substances 0.000 claims description 63
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 15
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- -1 aralkyl hydroperoxides Chemical class 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims 1
- 239000002585 base Substances 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 229910001882 dioxygen Inorganic materials 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 229960003742 phenol Drugs 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 3
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical class CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 2
- XCYJPXQACVEIOS-UHFFFAOYSA-N 1-isopropyl-3-methylbenzene Chemical compound CC(C)C1=CC=CC(C)=C1 XCYJPXQACVEIOS-UHFFFAOYSA-N 0.000 description 2
- TVYVQNHYIHAJTD-UHFFFAOYSA-N 2-propan-2-ylnaphthalene Chemical class C1=CC=CC2=CC(C(C)C)=CC=C21 TVYVQNHYIHAJTD-UHFFFAOYSA-N 0.000 description 2
- VLJSLTNSFSOYQR-UHFFFAOYSA-N 3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 2
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- OLBVUFHMDRJKTK-UHFFFAOYSA-N [N].[O] Chemical compound [N].[O] OLBVUFHMDRJKTK-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 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 1
- 229930007927 cymene Natural products 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002672 m-cresols Chemical class 0.000 description 1
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
- 150000002931 p-cresols Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- KFDFYCRDUBAKHD-UHFFFAOYSA-M sodium;carbamate Chemical compound [Na+].NC([O-])=O KFDFYCRDUBAKHD-UHFFFAOYSA-M 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
- C07C409/12—Compounds containing six-membered aromatic rings with two alpha,alpha-dialkylmethyl hydroperoxy groups bound to carbon atoms of the same six-membered aromatic ring
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15047971A | 1971-06-07 | 1971-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2227529A1 true DE2227529A1 (de) | 1972-12-28 |
Family
ID=22534714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722227529 Pending DE2227529A1 (de) | 1971-06-07 | 1972-06-06 | Verbessertes Verfahren zur Herstellung von aromatischen (sek.-C tief 3-tief 7-Alkyl) -hydroperoxiden |
Country Status (11)
| Country | Link |
|---|---|
| AU (1) | AU452419B2 (https=) |
| BE (1) | BE784536A (https=) |
| BR (1) | BR7203631D0 (https=) |
| CA (1) | CA984855A (https=) |
| DE (1) | DE2227529A1 (https=) |
| ES (1) | ES403961A1 (https=) |
| FR (1) | FR2140469B1 (https=) |
| GB (1) | GB1351429A (https=) |
| IT (1) | IT955983B (https=) |
| NL (1) | NL7207543A (https=) |
| SE (1) | SE370390B (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10240816A1 (de) * | 2002-08-30 | 2004-03-11 | Basf Ag | Oxidationsverfahren |
| CN106554298B (zh) * | 2015-09-28 | 2019-04-23 | 万华化学集团股份有限公司 | 一种乙苯氧化制备乙苯氢过氧化物的方法 |
-
1972
- 1972-05-12 CA CA141,958A patent/CA984855A/en not_active Expired
- 1972-05-25 AU AU42759/72A patent/AU452419B2/en not_active Expired
- 1972-05-26 GB GB2509272A patent/GB1351429A/en not_active Expired
- 1972-05-29 IT IT2502072A patent/IT955983B/it active
- 1972-06-02 NL NL7207543A patent/NL7207543A/xx not_active Application Discontinuation
- 1972-06-06 FR FR7220241A patent/FR2140469B1/fr not_active Expired
- 1972-06-06 BR BR363172A patent/BR7203631D0/pt unknown
- 1972-06-06 DE DE19722227529 patent/DE2227529A1/de active Pending
- 1972-06-07 BE BE784536A patent/BE784536A/xx unknown
- 1972-06-07 SE SE747172A patent/SE370390B/xx unknown
- 1972-06-07 ES ES403961A patent/ES403961A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA984855A (en) | 1976-03-02 |
| AU4275972A (en) | 1974-02-21 |
| BR7203631D0 (pt) | 1973-06-14 |
| SE370390B (https=) | 1974-10-14 |
| FR2140469A1 (https=) | 1973-01-19 |
| ES403961A1 (es) | 1975-05-01 |
| GB1351429A (en) | 1974-05-01 |
| IT955983B (it) | 1973-09-29 |
| FR2140469B1 (https=) | 1977-12-23 |
| BE784536A (fr) | 1972-12-07 |
| AU452419B2 (en) | 1974-09-05 |
| NL7207543A (https=) | 1972-12-11 |
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