DE1262993B - Verfahren zur Herstellung von Benzoesaeure - Google Patents
Verfahren zur Herstellung von BenzoesaeureInfo
- Publication number
- DE1262993B DE1262993B DEA48875A DEA0048875A DE1262993B DE 1262993 B DE1262993 B DE 1262993B DE A48875 A DEA48875 A DE A48875A DE A0048875 A DEA0048875 A DE A0048875A DE 1262993 B DE1262993 B DE 1262993B
- Authority
- DE
- Germany
- Prior art keywords
- benzoic acid
- toluene
- oxygen
- oxidation
- cobalt
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims description 71
- 239000005711 Benzoic acid Substances 0.000 title claims description 35
- 235000010233 benzoic acid Nutrition 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 63
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000007789 gas Substances 0.000 claims description 16
- 230000003647 oxidation Effects 0.000 claims description 14
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 3
- 150000001868 cobalt Chemical class 0.000 claims description 2
- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 description 10
- 239000010941 cobalt Substances 0.000 description 10
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003999 initiator Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 229940011182 cobalt acetate Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229940071125 manganese acetate Drugs 0.000 description 2
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- -1 aromatic carboxylic acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 238000007630 basic procedure Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000004868 gas analysis Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Electromechanical Clocks (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35836364A | 1964-04-08 | 1964-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1262993B true DE1262993B (de) | 1968-03-14 |
Family
ID=23409363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA48875A Pending DE1262993B (de) | 1964-04-08 | 1965-04-08 | Verfahren zur Herstellung von Benzoesaeure |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE662279A (fr) |
| CH (1) | CH443260A (fr) |
| DE (1) | DE1262993B (fr) |
| ES (1) | ES311608A1 (fr) |
| FR (1) | FR1429185A (fr) |
| GB (1) | GB1070227A (fr) |
| IL (1) | IL23319A (fr) |
| NL (1) | NL6504510A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106631761A (zh) * | 2016-09-12 | 2017-05-10 | 华东理工大学 | 一种低温常压氧化甲苯制苯甲酸的方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590559A (zh) * | 2019-08-19 | 2019-12-20 | 浙江工业大学 | 一种球磨法氧化甲苯及其衍生物选择性制备苯甲酸及其衍生物的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2963509A (en) * | 1958-03-10 | 1960-12-06 | Mid Century Corp | Process for oxidation of mono-alkyl benzene |
-
1965
- 1965-04-08 ES ES0311608A patent/ES311608A1/es not_active Expired
- 1965-04-08 IL IL2331965A patent/IL23319A/xx unknown
- 1965-04-08 GB GB1496265A patent/GB1070227A/en not_active Expired
- 1965-04-08 BE BE662279D patent/BE662279A/xx unknown
- 1965-04-08 NL NL6504510A patent/NL6504510A/xx unknown
- 1965-04-08 CH CH492765A patent/CH443260A/fr unknown
- 1965-04-08 FR FR12487A patent/FR1429185A/fr not_active Expired
- 1965-04-08 DE DEA48875A patent/DE1262993B/de active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2963509A (en) * | 1958-03-10 | 1960-12-06 | Mid Century Corp | Process for oxidation of mono-alkyl benzene |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106631761A (zh) * | 2016-09-12 | 2017-05-10 | 华东理工大学 | 一种低温常压氧化甲苯制苯甲酸的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CH443260A (de) | 1967-09-15 |
| ES311608A1 (es) | 1965-07-01 |
| FR1429185A (fr) | 1966-02-18 |
| IL23319A (en) | 1968-08-22 |
| BE662279A (fr) | 1965-08-02 |
| NL6504510A (fr) | 1965-10-11 |
| GB1070227A (en) | 1967-06-01 |
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