DE2615657C2 - - Google Patents
Info
- Publication number
- DE2615657C2 DE2615657C2 DE2615657A DE2615657A DE2615657C2 DE 2615657 C2 DE2615657 C2 DE 2615657C2 DE 2615657 A DE2615657 A DE 2615657A DE 2615657 A DE2615657 A DE 2615657A DE 2615657 C2 DE2615657 C2 DE 2615657C2
- Authority
- DE
- Germany
- Prior art keywords
- terephthalic acid
- acetic acid
- cobalt
- mass
- mixture
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 174
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 158
- 238000000034 method Methods 0.000 claims description 53
- 238000007254 oxidation reaction Methods 0.000 claims description 47
- 230000003647 oxidation Effects 0.000 claims description 46
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 36
- 229910017052 cobalt Inorganic materials 0.000 claims description 31
- 239000010941 cobalt Substances 0.000 claims description 31
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 31
- 239000011541 reaction mixture Substances 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 30
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 19
- 229910052748 manganese Inorganic materials 0.000 claims description 19
- 239000011572 manganese Substances 0.000 claims description 19
- 239000007789 gas Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 239000012452 mother liquor Substances 0.000 claims description 10
- 239000007791 liquid phase Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000002002 slurry Substances 0.000 claims description 5
- BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 claims description 4
- 150000002697 manganese compounds Chemical class 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- 150000001869 cobalt compounds Chemical class 0.000 claims description 3
- 238000010924 continuous production Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims 1
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 36
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
- 238000004519 manufacturing process Methods 0.000 description 24
- -1 aliphatic Monocarboxylic acid Chemical class 0.000 description 18
- 230000032050 esterification Effects 0.000 description 12
- 238000005886 esterification reaction Methods 0.000 description 12
- 229920000139 polyethylene terephthalate Polymers 0.000 description 12
- 239000005020 polyethylene terephthalate Substances 0.000 description 12
- 238000002485 combustion reaction Methods 0.000 description 11
- 238000011282 treatment Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 229940011182 cobalt acetate Drugs 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
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229940071125 manganese acetate Drugs 0.000 description 3
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 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 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 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 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940075581 sodium bromide Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB14964/75A GB1511181A (en) | 1975-04-11 | 1975-04-11 | Preparation of terephthalic acid by oxidation of p-xylene |
| GB3320475 | 1975-08-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2615657A1 DE2615657A1 (de) | 1976-10-21 |
| DE2615657C2 true DE2615657C2 (en:Method) | 1989-05-24 |
Family
ID=26250923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762615657 Granted DE2615657A1 (de) | 1975-04-11 | 1976-04-09 | Oxidationsverfahren, insbesondere zur herstellung von terephthalsaeure |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS6050775B2 (en:Method) |
| DE (1) | DE2615657A1 (en:Method) |
| FR (1) | FR2306967A1 (en:Method) |
| IT (1) | IT1063362B (en:Method) |
| NL (1) | NL7603780A (en:Method) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1595974A (en) * | 1977-04-07 | 1981-08-19 | Ici Ltd | Recovering catalyst values |
| GB1595904A (en) * | 1977-04-25 | 1981-08-19 | Ici Ltd | Recovery catalyst values |
| FR2413352A1 (fr) * | 1977-12-28 | 1979-07-27 | Mitsui Petrochemical Ind | Procede de preparation de l'acide terephtalique |
| NL7900151A (nl) * | 1978-01-13 | 1979-07-17 | Ici Ltd | Oxydatiewerkwijze. |
| JPS54160330A (en) * | 1978-06-05 | 1979-12-19 | Kuraray Yuka Kk | Preparation of high-purity terephthalic acid of stable quality |
| CN101622218B (zh) * | 2007-02-28 | 2013-08-07 | 株式会社日立工业设备技术 | 氢化精制用粗制芳香族二羧酸的制造方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2113424A5 (en:Method) * | 1970-11-01 | 1972-06-23 | Maruzen Oil Co Ltd | |
| JPS5328419B1 (en:Method) * | 1971-04-26 | 1978-08-15 | ||
| JPS5328421B2 (en:Method) * | 1973-05-15 | 1978-08-15 | ||
| JPS5328901B2 (en:Method) * | 1973-07-28 | 1978-08-17 |
-
1976
- 1976-04-09 NL NL7603780A patent/NL7603780A/xx not_active Application Discontinuation
- 1976-04-09 IT IT22164/76A patent/IT1063362B/it active
- 1976-04-09 DE DE19762615657 patent/DE2615657A1/de active Granted
- 1976-04-09 FR FR7610590A patent/FR2306967A1/fr active Granted
- 1976-04-12 JP JP51041176A patent/JPS6050775B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6050775B2 (ja) | 1985-11-11 |
| IT1063362B (it) | 1985-02-11 |
| JPS51127037A (en) | 1976-11-05 |
| FR2306967A1 (fr) | 1976-11-05 |
| NL7603780A (nl) | 1976-10-13 |
| FR2306967B1 (en:Method) | 1980-07-25 |
| DE2615657A1 (de) | 1976-10-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69230967T2 (de) | Verfahren zur herstellung von 2,6-naphthalindicarbonsäure | |
| DE69104280T2 (de) | Verfahren zur Herstellung von hochreiner Isophthalsäure. | |
| DE69506462T2 (de) | Verfahren zur Herstellung von aromatischer Carbonsäure | |
| DE2942375C2 (de) | Verfahren zur Herstellung von Terephthalsäure | |
| DE3209069C2 (en:Method) | ||
| DE2420960C2 (de) | Verfahren zur Oxydation von Di- oder Trimethylbenzolen mit molekularem Sauerstoff | |
| DE2436177C3 (de) | Verfahren zur Herstellung von Benzolcarbonsäuren durch Oxidation von Alkylbenzolen in flüssiger Phase | |
| DE3128147C2 (de) | Verfahren zur Gewinnung von aromatischen Monocarbonsäuren | |
| DE2627475C3 (de) | Verfahren zur Herstellung von Terephthalsäure | |
| DE2847170C2 (de) | Verfahren zur kontinuierlichen Herstellung von Terephthalsäure | |
| DE2154147C3 (de) | Verfahren zur Herstellung von Terephthalsäure | |
| DE2534161C2 (de) | Verfahren zur Herstellung von Terephthalsäure mit hoher Reinheit | |
| DE2615657C2 (en:Method) | ||
| DE69203947T2 (de) | Verfahren zur Herstellung von Trimellithsäure. | |
| DE2605363C3 (de) | Verfahren zur Herstellung von Phthalsäure | |
| DE2703161C2 (de) | Verfahren zur Herstellung von Terephthalsäure | |
| DE2749638A1 (de) | Verfahren zur herstellung von terephthalsaeure | |
| DE2540331C3 (de) | Verfahren zur Herstellung von Terephthalsäure oder Isophthalsäure | |
| DE2603173A1 (de) | Verfahren zur herstellung einer ungeschwaerzten phthalsaeure aus dem entsprechenden tolylaldehyd | |
| DE2355415C3 (de) | Verfahren zur Herstellung von Terephthalsäure | |
| DE60009785T2 (de) | Verfahren zur Herstellung von Pyromellitsäure | |
| DE68925222T2 (de) | Verfahren zur Herstellung von 2,6-Naphthalindicarbonsäure | |
| DE2615070A1 (de) | Verfahren zur herstellung von terephthalsaeure | |
| DE1297092B (de) | Verfahren zur Gewinnung von reiner Terephthalsaeure | |
| DE2243158C3 (de) | Verfahren zur Herstellung der 2,6-Naphthalindicarbonsäure |
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 |