GB908736A - Improvements in the production of terephthalic acid - Google Patents
Improvements in the production of terephthalic acidInfo
- Publication number
- GB908736A GB908736A GB2006660A GB2006660A GB908736A GB 908736 A GB908736 A GB 908736A GB 2006660 A GB2006660 A GB 2006660A GB 2006660 A GB2006660 A GB 2006660A GB 908736 A GB908736 A GB 908736A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxygen
- bromide
- oxidation
- acids
- 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.)
- Expired
Links
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title abstract 4
- 230000003647 oxidation Effects 0.000 abstract 6
- 238000007254 oxidation reaction Methods 0.000 abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 5
- 239000001301 oxygen Substances 0.000 abstract 5
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 4
- 229910017052 cobalt Inorganic materials 0.000 abstract 3
- 239000010941 cobalt Substances 0.000 abstract 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkyl radical Chemical class 0.000 abstract 2
- 229910052788 barium Inorganic materials 0.000 abstract 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 abstract 2
- VMHAYKUZIAAXIZ-UHFFFAOYSA-N 1,2-bis(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=CC=C1CC(C)C VMHAYKUZIAAXIZ-UHFFFAOYSA-N 0.000 abstract 1
- KGKAYWMGPDWLQZ-UHFFFAOYSA-N 1,2-bis(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1CBr KGKAYWMGPDWLQZ-UHFFFAOYSA-N 0.000 abstract 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 abstract 1
- SKBBQSLSGRSQAJ-UHFFFAOYSA-N 1-(4-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)C=C1 SKBBQSLSGRSQAJ-UHFFFAOYSA-N 0.000 abstract 1
- ADQDTIAWIXUACV-UHFFFAOYSA-N 1-ethyl-4-propylbenzene Chemical class CCCC1=CC=C(CC)C=C1 ADQDTIAWIXUACV-UHFFFAOYSA-N 0.000 abstract 1
- ZQVKTHRQIXSMGY-UHFFFAOYSA-N 4-Ethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1 ZQVKTHRQIXSMGY-UHFFFAOYSA-N 0.000 abstract 1
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 abstract 1
- QBHDSQZASIBAAI-UHFFFAOYSA-N 4-acetylbenzoic acid Chemical compound CC(=O)C1=CC=C(C(O)=O)C=C1 QBHDSQZASIBAAI-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical class CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004153 Potassium bromate Substances 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- ZJRXSAYFZMGQFP-UHFFFAOYSA-N barium peroxide Chemical compound [Ba+2].[O-][O-] ZJRXSAYFZMGQFP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 abstract 1
- 229950005228 bromoform Drugs 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical class ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 1
- RJYMRRJVDRJMJW-UHFFFAOYSA-L dibromomanganese Chemical compound Br[Mn]Br RJYMRRJVDRJMJW-UHFFFAOYSA-L 0.000 abstract 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000005313 fatty acid group Chemical group 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000005609 naphthenate group Chemical group 0.000 abstract 1
- 125000005608 naphthenic acid group Chemical group 0.000 abstract 1
- 150000001451 organic peroxides Chemical class 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 235000019396 potassium bromate Nutrition 0.000 abstract 1
- 229940094037 potassium bromate Drugs 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 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)
Abstract
A process for the production of terephthalic acid by oxidising first in the liquid phase a para-dialkyl-benzene having at least two carbon atoms in each alkyl radical or an intermediate oxidation product thereof in the presence of a salt of cobalt, manganese, barium or lead which is soluble in said paradialkyl benzene as catalyst, with oxygen at a temperature between about 100 DEG and 170 DEG C., dissolving the resultant oxidation product in a solvent inert to oxygen, continuing the oxidation with oxygen at temperatures between 120 DEG and 200 DEG C. under a pressure of about 3 to 50 atmospheres absolute until the absorption of oxygen has ended and then after adding bromine or a bromine compound, leading the oxidation to its conclusion with oxygen at temperatures between 150 and 200 DEG C. and pressures of about 3 to 50 atmospheres absolute. Starting materials specified include p-diethyl-, di-n-propyl-, di-iso-propyl-, di-n-butyl- or di-iso-butyl-benzene and the corresponding mixed dialkyl benzenes e.g. p-ethylpropyl-benzenes. Intermediate oxidation products specified include p-cumic-, and p-a -dihydroxycumic acids, a ,a 1-dihydroxy-1,4-diethylbenzene, p-ethylbenzoic acid, p-diacetylbenzene and p-acetyl-benzoic acid. Salts of cobalt, manganese, barium and lead with higher fatty or naphthenic acids e.g. octenates and naphthenates may be used as catalysts. Oxidation initiators which may be employed include tetraethyl lead and inorganic and organic peroxides and include sodium, potassium or barium peroxide, benzoyl peroxide, perbenzoic and peracetic acids, substances forming peroxides under the reaction conditions e.g. aldehydes, ketones, ethers and olefines, several of which are specified, and ozone. Solvents specified include aliphatic and araliphatic carboxylic acids, diphenyl, diphenyl ethers, chlorbenzenes, chlorpolyphenyls and naphthalene. Bromine compounds specified include hydrogen bromide and its salts, e.g. ammonium, cobalt and manganese bromide, potassium bromate, xylylene dibromide, benzyl bromide, ethylene bromide, bromoform, cyclohexyl bromide and bromacetaldehyde. Examples are furnished. Specification 807,091 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC19957A DE1106751B (en) | 1959-10-13 | 1959-10-13 | Process for the preparation of terephthalic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB908736A true GB908736A (en) | 1962-10-24 |
Family
ID=7016718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2006660A Expired GB908736A (en) | 1959-10-13 | 1960-06-08 | Improvements in the production of terephthalic acid |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1106751B (en) |
| GB (1) | GB908736A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3406196A (en) * | 1964-09-30 | 1968-10-15 | Du Pont | Oxidation of polyalkyl aromatics to polycarboxylic acids |
| US3431296A (en) * | 1963-10-10 | 1969-03-04 | Teijin Ltd | Process for preparation of high purity terephthalic acid |
| US3974214A (en) * | 1974-02-27 | 1976-08-10 | Atlantic Richfield Company | Isophthalic acid manufacture |
| US4755622A (en) * | 1983-12-29 | 1988-07-05 | Amoco Corporation | Process for the production of trimellitic acid and pyromellitic acid by staged bromine addition in an oxidation of polyalkylaromatics |
| CN112479861A (en) * | 2020-12-10 | 2021-03-12 | 成家钢 | Liquid-phase normal-pressure catalytic oxygen oxidation safety method and oxygen oxidation safety reaction equipment |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB983677A (en) * | 1962-04-27 | 1965-02-17 | Mitsui Petrochemical Ind | A process for the preparation of terephthalic acid having extremely high purity |
| DE1270030C2 (en) * | 1962-04-27 | 1973-07-19 | METHOD FOR PURIFYING TEREPHTHALIC ACID |
-
1959
- 1959-10-13 DE DEC19957A patent/DE1106751B/en active Pending
-
1960
- 1960-06-08 GB GB2006660A patent/GB908736A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3431296A (en) * | 1963-10-10 | 1969-03-04 | Teijin Ltd | Process for preparation of high purity terephthalic acid |
| US3406196A (en) * | 1964-09-30 | 1968-10-15 | Du Pont | Oxidation of polyalkyl aromatics to polycarboxylic acids |
| US3974214A (en) * | 1974-02-27 | 1976-08-10 | Atlantic Richfield Company | Isophthalic acid manufacture |
| US4755622A (en) * | 1983-12-29 | 1988-07-05 | Amoco Corporation | Process for the production of trimellitic acid and pyromellitic acid by staged bromine addition in an oxidation of polyalkylaromatics |
| CN112479861A (en) * | 2020-12-10 | 2021-03-12 | 成家钢 | Liquid-phase normal-pressure catalytic oxygen oxidation safety method and oxygen oxidation safety reaction equipment |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1106751B (en) | 1961-05-18 |
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