GB747204A - Process for the production of terephthalic acid or derivatives thereof from phthalic acid - Google Patents
Process for the production of terephthalic acid or derivatives thereof from phthalic acidInfo
- Publication number
- GB747204A GB747204A GB32184/53A GB3218453A GB747204A GB 747204 A GB747204 A GB 747204A GB 32184/53 A GB32184/53 A GB 32184/53A GB 3218453 A GB3218453 A GB 3218453A GB 747204 A GB747204 A GB 747204A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- terephthalic acid
- reaction
- oxide
- potassium
- 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 14
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 title abstract 8
- 238000000034 method Methods 0.000 title abstract 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000001569 carbon dioxide Substances 0.000 abstract 3
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 3
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- COHDHYZHOPQOFD-UHFFFAOYSA-N arsenic pentoxide Chemical compound O=[As](=O)O[As](=O)=O COHDHYZHOPQOFD-UHFFFAOYSA-N 0.000 abstract 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 abstract 2
- GOMCKELMLXHYHH-UHFFFAOYSA-L dipotassium;phthalate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=CC=C1C([O-])=O GOMCKELMLXHYHH-UHFFFAOYSA-L 0.000 abstract 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 abstract 2
- HJTAZXHBEBIQQX-UHFFFAOYSA-N 1,5-bis(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1CCl HJTAZXHBEBIQQX-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 abstract 1
- 239000005751 Copper oxide Substances 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 229910000410 antimony oxide Inorganic materials 0.000 abstract 1
- GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001559 benzoic acids Chemical class 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 238000003763 carbonization Methods 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- IAQWMWUKBQPOIY-UHFFFAOYSA-N chromium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Cr+4] IAQWMWUKBQPOIY-UHFFFAOYSA-N 0.000 abstract 1
- AYTAKQFHWFYBMA-UHFFFAOYSA-N chromium(IV) oxide Inorganic materials O=[Cr]=O AYTAKQFHWFYBMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000571 coke Substances 0.000 abstract 1
- 229910000431 copper oxide Inorganic materials 0.000 abstract 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 229910000464 lead oxide Inorganic materials 0.000 abstract 1
- 229910021514 lead(II) hydroxide Inorganic materials 0.000 abstract 1
- 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 1
- 229960002523 mercuric chloride Drugs 0.000 abstract 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052753 mercury Inorganic materials 0.000 abstract 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 235000011181 potassium carbonates Nutrition 0.000 abstract 1
- 239000001103 potassium chloride Substances 0.000 abstract 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 abstract 1
- 235000011164 potassium chloride Nutrition 0.000 abstract 1
- IWZKICVEHNUQTL-UHFFFAOYSA-M potassium hydrogen phthalate Chemical compound [K+].OC(=O)C1=CC=CC=C1C([O-])=O IWZKICVEHNUQTL-UHFFFAOYSA-M 0.000 abstract 1
- 229910052939 potassium sulfate Inorganic materials 0.000 abstract 1
- 239000001120 potassium sulphate Substances 0.000 abstract 1
- 235000011151 potassium sulphates Nutrition 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000004576 sand Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
- 150000003639 trimesic acids Chemical class 0.000 abstract 1
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 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
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/416—Henkel reaction and related reactions, i.e. rearrangement of carboxylate salt groups linked to six-membered aromatic rings, in the absence or in the presence of CO or CO2, (e.g. preparation of terepholates from benzoates); no additional classification for the subsequent hydrolysis of the salt groups has to be given
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| DE747204X | 1952-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB747204A true GB747204A (en) | 1956-03-28 |
Family
ID=6648575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32184/53A Expired GB747204A (en) | 1952-11-21 | 1953-11-20 | Process for the production of terephthalic acid or derivatives thereof from phthalic acid |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2863914A (OSRAM) |
| BE (1) | BE522829A (OSRAM) |
| FR (1) | FR1090261A (OSRAM) |
| GB (1) | GB747204A (OSRAM) |
| NL (2) | NL87537C (OSRAM) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2906774A (en) * | 1956-05-26 | 1959-09-29 | Henkel & Compagnie G M B H | Process for the production of aromatic di- and polycarboxylic acids |
| US3010802A (en) * | 1956-03-06 | 1961-11-28 | Henkel & Compagnie G M B H | Apparatus for the continuous reaction of solid materials |
| US3014067A (en) * | 1956-10-15 | 1961-12-19 | Henkel & Cie Gmbh | Process for the production of aromatic di-and polycarboxylic acids |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE522829A (OSRAM) * | 1952-11-21 | |||
| BE547302A (OSRAM) * | 1955-05-04 | |||
| US2891992A (en) * | 1955-12-08 | 1959-06-23 | Henkel & Cie Gmbh | Process for the rearrangement of salts of aromatic or heterocyclic carboxylic acids |
| US2930813A (en) * | 1955-12-09 | 1960-03-29 | Henkel & Cie Gmbh | Process for the preparation of cyclic dicarboxylic acids |
| US3101368A (en) * | 1956-01-03 | 1963-08-20 | Henkel & Cie Gmbh | Process for the preparation of cyclic dicarboxylic acids |
| US3093683A (en) * | 1956-01-12 | 1963-06-11 | Henkel & Cie Gmbh | Process for the transformation of benzene polycarboxylic acids to terephthalic acid |
| NL213764A (OSRAM) * | 1956-01-17 | |||
| US2965674A (en) * | 1957-01-22 | 1960-12-20 | Monsanto Chemicals | Preparation of terephthalates by heating benzoic acid salts under pressure of gases |
| US3023216A (en) * | 1958-03-07 | 1962-02-27 | Henkel & Cie Gmbh | Process for the introduction of carboxyl groups into aromatic compounds |
| DE1142597B (de) * | 1961-07-21 | 1963-01-24 | Basf Ag | Verfahren zur Gewinnung trockener, neutraler Alkalisalze cyclischer Carbonsaeuren |
| US3546282A (en) * | 1964-02-18 | 1970-12-08 | Tamotsu Murase | Process for the production of alkali aromatic dicarboxylates |
| US3479399A (en) * | 1964-08-14 | 1969-11-18 | Ube Kogyo Kk | Process for the production of alkali metal terephthalates |
| US3761515A (en) * | 1971-10-21 | 1973-09-25 | Chevron Res | Preparation of potassium terephthalate |
| CA2801397C (en) * | 2010-06-03 | 2018-04-24 | Stora Enso Oyj | Hydrogen treatment of impure tall oil for the production of aromatic monomers |
| FI125507B2 (en) | 2012-04-13 | 2021-12-15 | Stora Enso Oyj | Process for deoxygenating tall oil and producing polymerizable monomers therefrom |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1937477A (en) * | 1932-07-05 | 1933-11-28 | Dow Chemical Co | Process of preparing para-hydroxybenzoic acid |
| BE522829A (OSRAM) * | 1952-11-21 |
-
0
- BE BE522829D patent/BE522829A/xx unknown
- NL NLAANVRAGE7511387,A patent/NL181266B/xx unknown
- NL NL87537D patent/NL87537C/xx active
-
1953
- 1953-11-16 FR FR1090261D patent/FR1090261A/fr not_active Expired
- 1953-11-20 GB GB32184/53A patent/GB747204A/en not_active Expired
-
1957
- 1957-01-24 US US635945A patent/US2863914A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3010802A (en) * | 1956-03-06 | 1961-11-28 | Henkel & Compagnie G M B H | Apparatus for the continuous reaction of solid materials |
| US2906774A (en) * | 1956-05-26 | 1959-09-29 | Henkel & Compagnie G M B H | Process for the production of aromatic di- and polycarboxylic acids |
| US3014067A (en) * | 1956-10-15 | 1961-12-19 | Henkel & Cie Gmbh | Process for the production of aromatic di-and polycarboxylic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| BE522829A (OSRAM) | |
| NL87537C (OSRAM) | |
| US2863914A (en) | 1958-12-09 |
| FR1090261A (fr) | 1955-03-29 |
| NL181266B (nl) |
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