DE2508452C2 - Verfahren zur Herstellung von Alkylphenolen - Google Patents
Verfahren zur Herstellung von AlkylphenolenInfo
- Publication number
- DE2508452C2 DE2508452C2 DE2508452A DE2508452A DE2508452C2 DE 2508452 C2 DE2508452 C2 DE 2508452C2 DE 2508452 A DE2508452 A DE 2508452A DE 2508452 A DE2508452 A DE 2508452A DE 2508452 C2 DE2508452 C2 DE 2508452C2
- Authority
- DE
- Germany
- Prior art keywords
- mol
- aldehyde
- hydrogen fluoride
- hydrogen peroxide
- reaction
- 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
- 238000000034 method Methods 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 3
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- -1 aromatic compounds Aldehydes Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 33
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 33
- 150000001299 aldehydes Chemical class 0.000 description 20
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 18
- 150000003934 aromatic aldehydes Chemical class 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000004675 formic acid derivatives Chemical class 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VXSCPERJHPWROZ-UHFFFAOYSA-N 2,4,5-trimethylphenol Chemical compound CC1=CC(C)=C(O)C=C1C VXSCPERJHPWROZ-UHFFFAOYSA-N 0.000 description 2
- GISVICWQYMUPJF-UHFFFAOYSA-N 2,4-Dimethylbenzaldehyde Chemical compound CC1=CC=C(C=O)C(C)=C1 GISVICWQYMUPJF-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
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000022244 formylation Effects 0.000 description 2
- 238000006170 formylation reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- SMUVABOERCFKRW-UHFFFAOYSA-N 2,5-Dimethylbenzaldehyde Chemical compound CC1=CC=C(C)C(C=O)=C1 SMUVABOERCFKRW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- 238000006220 Baeyer-Villiger oxidation reaction Methods 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- LROJZZICACKNJL-UHFFFAOYSA-N Duryl aldehyde Chemical compound CC1=CC(C)=C(C=O)C=C1C LROJZZICACKNJL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000010543 cumene process Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 239000011289 tar acid Substances 0.000 description 1
Classifications
-
- 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
- C07C39/06—Alkylated phenols
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2504374A JPS5328894B2 (en, 2012) | 1974-03-04 | 1974-03-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2508452A1 DE2508452A1 (de) | 1975-09-11 |
| DE2508452C2 true DE2508452C2 (de) | 1984-05-24 |
Family
ID=12154875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2508452A Expired DE2508452C2 (de) | 1974-03-04 | 1975-02-27 | Verfahren zur Herstellung von Alkylphenolen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3976702A (en, 2012) |
| JP (1) | JPS5328894B2 (en, 2012) |
| DE (1) | DE2508452C2 (en, 2012) |
| FR (1) | FR2263216B1 (en, 2012) |
| GB (1) | GB1431876A (en, 2012) |
| IT (1) | IT1033359B (en, 2012) |
| NL (1) | NL7502534A (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4051318A (en) * | 1975-01-16 | 1977-09-27 | Mitsubishi Gas Chemical Company, Inc. | Process for preparing formate esters of alkyl-substituted aromatic hydroxy compounds |
| US4528394A (en) * | 1983-08-03 | 1985-07-09 | The Dow Chemical Company | Preparation of hydroxyaromatic ethers |
| US4684752A (en) * | 1986-04-30 | 1987-08-04 | The Dow Chemical Company | Di-ortho-substituted di-meta-halogenated para-halomethylphenols |
| US4908476A (en) * | 1988-03-21 | 1990-03-13 | Hoechst Celanese Corporation | Synthesis of 2-(4-hydroxyphenoxy)alkanoic acids |
| US5008439A (en) * | 1988-03-21 | 1991-04-16 | Hoechst Celanese Corporation | Synthesis of 2-(4-hydroxyphenoxy) alkanoic acid esters |
| JP3036555B2 (ja) * | 1991-06-26 | 2000-04-24 | 三菱瓦斯化学株式会社 | 蟻酸アリールと芳香族カルボン酸の同時製造法 |
| EP1209145A3 (en) * | 1998-07-17 | 2002-06-19 | Mitsubishi Gas Chemical Company, Inc. | Process for preparing an aryl formate and an aromatic carboxylic acid |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3678104A (en) * | 1969-09-29 | 1972-07-18 | Universal Oil Prod Co | Hydroxylation of aromatic acids |
| BE789738A (fr) * | 1971-10-06 | 1973-04-05 | Rhone Poulenc Sa | Alcoylphenols par oxydation d'alcoylbenzaldehydes |
| BE791582A (fr) * | 1971-11-19 | 1973-05-17 | Rhone Poulenc Sa | Procede de preparation de phenols par oxydation d'aldehydes aromatique |
-
1974
- 1974-03-04 JP JP2504374A patent/JPS5328894B2/ja not_active Expired
-
1975
- 1975-02-27 DE DE2508452A patent/DE2508452C2/de not_active Expired
- 1975-03-03 IT IT20845/75A patent/IT1033359B/it active
- 1975-03-03 GB GB881675A patent/GB1431876A/en not_active Expired
- 1975-03-04 FR FR7506755A patent/FR2263216B1/fr not_active Expired
- 1975-03-04 US US05/555,113 patent/US3976702A/en not_active Expired - Lifetime
- 1975-03-04 NL NL7502534A patent/NL7502534A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2263216A1 (en, 2012) | 1975-10-03 |
| FR2263216B1 (en, 2012) | 1982-07-09 |
| US3976702A (en) | 1976-08-24 |
| JPS5328894B2 (en, 2012) | 1978-08-17 |
| NL7502534A (nl) | 1975-09-08 |
| DE2508452A1 (de) | 1975-09-11 |
| GB1431876A (en) | 1976-04-14 |
| IT1033359B (it) | 1979-07-10 |
| JPS50117738A (en, 2012) | 1975-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |