DE2116212C3 - - Google Patents
Info
- Publication number
- DE2116212C3 DE2116212C3 DE2116212A DE2116212A DE2116212C3 DE 2116212 C3 DE2116212 C3 DE 2116212C3 DE 2116212 A DE2116212 A DE 2116212A DE 2116212 A DE2116212 A DE 2116212A DE 2116212 C3 DE2116212 C3 DE 2116212C3
- Authority
- DE
- Germany
- Prior art keywords
- xylene
- acid
- reaction
- oxygen
- hydrogen bromide
- 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 22
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910017604 nitric acid Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims 6
- 239000002609 medium Substances 0.000 claims 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims 4
- 239000007791 liquid phase Substances 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 2
- -1 aromatic carboxylic acids Chemical class 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 101100346764 Mus musculus Mtln gene Proteins 0.000 claims 1
- 230000001133 acceleration Effects 0.000 claims 1
- 230000002730 additional effect Effects 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 238000011109 contamination Methods 0.000 claims 1
- 230000007613 environmental effect Effects 0.000 claims 1
- XDYHDLLKHFVVSE-UHFFFAOYSA-N hydrate;dihydrobromide Chemical compound O.Br.Br XDYHDLLKHFVVSE-UHFFFAOYSA-N 0.000 claims 1
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 235000010333 potassium nitrate Nutrition 0.000 claims 1
- 239000004323 potassium nitrate Substances 0.000 claims 1
- 238000010926 purge Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000010517 secondary reaction Methods 0.000 claims 1
- 238000009958 sewing Methods 0.000 claims 1
- 239000003610 charcoal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 241000282320 Panthera leo Species 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007306 turnover Effects 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2525170A | 1970-04-02 | 1970-04-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2116212A1 DE2116212A1 (en, 2012) | 1972-02-17 |
| DE2116212B2 DE2116212B2 (de) | 1973-03-22 |
| DE2116212C3 true DE2116212C3 (en, 2012) | 1973-11-15 |
Family
ID=21824945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712116212 Granted DE2116212B2 (de) | 1970-04-02 | 1971-04-02 | Verfahren zur herstellung von terephthalsaeure |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3678106A (en, 2012) |
| CA (1) | CA946410A (en, 2012) |
| DE (1) | DE2116212B2 (en, 2012) |
| FR (1) | FR2089101A5 (en, 2012) |
| GB (1) | GB1314915A (en, 2012) |
| NL (1) | NL7103373A (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS609018B2 (ja) * | 1977-01-26 | 1985-03-07 | 三菱瓦斯化学株式会社 | テレフタル酸の製造法 |
| JPS5490132A (en) * | 1977-12-07 | 1979-07-17 | Mitsubishi Gas Chem Co Inc | Preparation of high purity terephthalic acid |
| JPS5481238A (en) * | 1977-12-13 | 1979-06-28 | Mitsubishi Gas Chem Co Inc | Production of high-purity terephthalic acid |
| JPS5488234A (en) * | 1977-12-22 | 1979-07-13 | Mitsubishi Gas Chem Co Inc | Purification of terephthalic acid |
| JPS54125631A (en) * | 1978-02-20 | 1979-09-29 | Mitsubishi Gas Chem Co Inc | Preparation of high-purity terephthalic acid |
| JPS5517309A (en) * | 1978-07-21 | 1980-02-06 | Mitsubishi Gas Chem Co Inc | Preparation of high purity terephthalic acid |
| JPS582222B2 (ja) * | 1979-08-13 | 1983-01-14 | 三菱瓦斯化学株式会社 | 芳香族ポリカルボン酸の製造法 |
| EP0041785B1 (en) * | 1980-06-10 | 1985-05-02 | Imperial Chemical Industries Plc | Oxidation of substituted aromatic compounds to aromatic carboxylic acids |
| WO1999062859A1 (fr) | 1998-06-03 | 1999-12-09 | Daikin Industries, Ltd. | Procede de production d'acide fluoroalkylcaboxylique |
| CN111182968A (zh) | 2017-10-05 | 2020-05-19 | 诺沃梅尔公司 | 异氰酸酯、其衍生物及它们的生产方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2391740A (en) * | 1944-01-17 | 1945-12-25 | Shell Dev | Sensitization of hydrogen bromide catalyzed oxidation reactions |
| US2644840A (en) * | 1948-08-07 | 1953-07-07 | Monsanto Chemicals | Oxidation of hydrocarbons |
| US3532746A (en) * | 1966-09-20 | 1970-10-06 | Standard Oil Co | Two stage oxidation |
-
1970
- 1970-04-02 US US25251A patent/US3678106A/en not_active Expired - Lifetime
-
1971
- 1971-02-16 CA CA105,490A patent/CA946410A/en not_active Expired
- 1971-03-12 NL NL7103373A patent/NL7103373A/xx unknown
- 1971-04-02 DE DE19712116212 patent/DE2116212B2/de active Granted
- 1971-04-02 FR FR7111736A patent/FR2089101A5/fr not_active Expired
- 1971-04-19 GB GB2583171*A patent/GB1314915A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA946410A (en) | 1974-04-30 |
| GB1314915A (en) | 1973-04-26 |
| NL7103373A (en, 2012) | 1971-10-05 |
| FR2089101A5 (en, 2012) | 1972-01-07 |
| US3678106A (en) | 1972-07-18 |
| DE2116212B2 (de) | 1973-03-22 |
| DE2116212A1 (en, 2012) | 1972-02-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |