KR900006263A - 알킬방향족 화합물로부터 방향족 산을 제조하기 위한 산화공정 - Google Patents
알킬방향족 화합물로부터 방향족 산을 제조하기 위한 산화공정 Download PDFInfo
- Publication number
- KR900006263A KR900006263A KR1019880013548A KR880013548A KR900006263A KR 900006263 A KR900006263 A KR 900006263A KR 1019880013548 A KR1019880013548 A KR 1019880013548A KR 880013548 A KR880013548 A KR 880013548A KR 900006263 A KR900006263 A KR 900006263A
- Authority
- KR
- South Korea
- Prior art keywords
- zirconium
- acid
- atoms
- oxidation
- milligrams
- 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.)
- Granted
Links
- 230000003647 oxidation Effects 0.000 title claims 5
- 238000007254 oxidation reaction Methods 0.000 title claims 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 229910052726 zirconium Inorganic materials 0.000 claims 5
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 claims 4
- 239000007791 liquid phase Substances 0.000 claims 4
- 229910052759 nickel Inorganic materials 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 2
- 229910052748 manganese Inorganic materials 0.000 claims 2
- 239000011572 manganese Substances 0.000 claims 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 claims 2
- 239000012429 reaction media Substances 0.000 claims 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003628 tricarboxylic acids Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B33/00—Oxidation in general
-
- 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
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/889—Manganese, technetium or rhenium
- B01J23/8892—Manganese
-
- 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
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0231—Halogen-containing compounds
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
- B01J2231/76—Dehydrogenation
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (6)
- 산화시에p-크실렌,m-크실렌 또는 슈도쿠멘의 각각의 그램 몰에 대하여 닉켈 약 4 내지 약 20밀리그램원자, 지르코늄 약 0.10 내지 약 0.30밀리그램원자, 총 망각 약 2 내지 약 10밀리그램원자 및 브롬 약 8 내지 24밀리그램원자가 존재하는, 브롬과 닉켈, 지르코늄 및 망간과의 공급원을 포함하는 촉매계의 존재하에 산화를 수행함을 특징으로 하여, 디-및 트리메틸벤젠을 액상 조건하에서 5개 미만의 탄소원자를 갖는 지방족산의 존재하에 또는 물의 존재하에 또는 지방족 산과 물과의 혼합물의 존재하에 약 100℃ 내지 260℃의 온도및 반응 매질의 70 내지 80%를 액상으로 유지하는 압력에서 분자산소를 사용하여 벤젠 디- 및 트리카복실산으로 산화시키는 방법.
- 제1항에 있어서, 닉켈 : 지르코늄 : 망간의 그램원자 비율이 약 33 : 1 : 12 내지 약 80 : 1 : 43의 범위이고, 용매가 아세트산 또는 물인 방법.
- 제2항에 있어서,p-크실렌을 테레프탈산으로 산화시키는 방법.
- 제2항에 있어서,m-크실렌을 이소프탈산으로 산화시키는 방법.
- 제2항에 있어서, 슈도큐멘을 트리멜리트산으로 산화시키는 방법.
- 산화시에 슈도쿠멘의 각각의 그램몰에 대하여 닉켈 약 4 내지 약 20밀리그램원자, 지르코늄 약 0.10 내지 약 0.30밀리그램원자, 총 망간 약 2 내지 약 10밀리그램원자 및 브롬 약 8 내지 24밀리그램원자가 존재하는, 브롬과 닉켈, 지르코늄 및 망간과의 공급원을 포함하는 촉매계의 존재하에 슈도큐멘을 액상조건하에서 100℃ 내지 260℃범위의 온도 및 반응매질의 70 내지 80%를 액상으로 유지하는 압력에서, 분자산소를 사용하여 액상 산화시키는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US050,860 | 1987-05-18 | ||
| US07/050,860 US4786753A (en) | 1987-05-18 | 1987-05-18 | Oxidation process for the manufacture of aromatic acids from alkylaromatic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR900006263A true KR900006263A (ko) | 1990-05-07 |
| KR960015910B1 KR960015910B1 (ko) | 1996-11-23 |
Family
ID=21967929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880013548A Expired - Lifetime KR960015910B1 (ko) | 1987-05-18 | 1988-10-18 | 알킬 방향족 화합물로부터 방향족 산을 제조하기 위한 산화공정 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4786753A (ko) |
| EP (1) | EP0362443B1 (ko) |
| KR (1) | KR960015910B1 (ko) |
| ES (1) | ES2047557T3 (ko) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100427298B1 (ko) | 2001-03-31 | 2004-04-17 | 한국화학연구원 | 알킬방향족 화합물의 액상산화에 의한 방향족카르복시산의 제조방법 |
| US4996353A (en) * | 1989-05-16 | 1991-02-26 | The Dow Chemical Company | Process for the preparation of para,para'-polyphenyldicarboxylic acid |
| US5028737A (en) * | 1990-02-22 | 1991-07-02 | Amoco Corporation | Preparation of isopropylidene bis(phthalic acid) |
| GB9104776D0 (en) * | 1991-03-07 | 1991-04-17 | Ici Plc | Process for the production of terephthalic acid |
| KR970000136B1 (ko) * | 1993-09-28 | 1997-01-04 | 브이.피. 유리예프 | 고순도 벤젠디카르복실산 이성질체의 제조방법 |
| US5895820A (en) * | 1997-07-16 | 1999-04-20 | Mitsubishi Gas Chemical Company, Inc. | Process for the production of trimellitic acid and process for the production of trimellitic acid anhydride |
| US6649773B2 (en) | 2002-03-22 | 2003-11-18 | General Electric Company | Method for the manufacture of halophthalic acids and anhydrides |
| US6657068B2 (en) | 2002-03-22 | 2003-12-02 | General Electric Company | Liquid phase oxidation of halogenated ortho-xylenes |
| US6657067B2 (en) | 2002-03-22 | 2003-12-02 | General Electric Company | Method for the manufacture of chlorophthalic anhydride |
| US7348452B2 (en) * | 2004-04-22 | 2008-03-25 | Eastman Chemical Company | Liquid phase oxidation of P-xylene to terephthalic acid in the presence of a catalyst system containing nickel, manganese, and bromine atoms |
| US7541489B2 (en) | 2004-06-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Method of making halophthalic acids and halophthalic anhydrides |
| US7550627B2 (en) | 2005-03-08 | 2009-06-23 | Eastman Chemical Company | Processes for producing aromatic dicarboxylic acids |
| US20060205974A1 (en) * | 2005-03-08 | 2006-09-14 | Lavoie Gino G | Processes for producing aromatic dicarboxylic acids |
| CN105688988B (zh) * | 2014-12-16 | 2018-11-27 | 财团法人工业技术研究院 | 糠醛化合物的氧化反应催化剂及糠醛化合物的氧化方法 |
| CN106349048B (zh) * | 2016-08-26 | 2019-03-15 | 浙江大学 | 一种间二甲苯氧化生产间苯二甲酸的方法及装置 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2245528A (en) * | 1938-10-18 | 1941-06-10 | Du Pont | Catalytic oxidation of alkyl substituted aromatic compounds |
| US2833816A (en) * | 1954-05-03 | 1958-05-06 | Mid Century Corp | Preparation of aromatic polycarboxylic acids |
| BE562538A (ko) * | 1956-11-21 | 1900-01-01 | ||
| US3819695A (en) * | 1971-04-28 | 1974-06-25 | Teijin Ltd | Process for preparation of methylterephthalic acid and 4-methylisophthalic acid |
| US3920735A (en) * | 1973-05-21 | 1975-11-18 | Standard Oil Co | Zirconium enhanced activity of transition metal-bromine catalysis of di- and trimethyl benzene oxidation in liquid phase |
| US4330676A (en) * | 1977-07-04 | 1982-05-18 | Imperial Chemical Industries Limited | Oxidation process |
| DE2962928D1 (en) * | 1978-12-21 | 1982-07-08 | Ici Plc | Recovery of bromine from the effluent gases of a bromine catalysed oxidation process |
| EP0034413A1 (en) * | 1980-02-12 | 1981-08-26 | Imperial Chemical Industries Plc | Process for the preparation of diphenylether carboxylic acids |
| EP0041784A1 (en) * | 1980-06-10 | 1981-12-16 | Imperial Chemical Industries Plc | Oxidation of substituted aromatic compounds to aromatic carboxylic acids |
| EP0041778B2 (en) * | 1980-06-10 | 1988-08-24 | Imperial Chemical Industries Plc | Oxidation of meta- or para-xylene to iso- or tere-phthalic acid |
| US4754062A (en) * | 1985-05-24 | 1988-06-28 | Amoco Corporation | Iron-enhanced selectivity of heavy metal-bromine catalysis in the oxidation of polyalkylaromatics |
| JP3692390B2 (ja) * | 1996-04-19 | 2005-09-07 | 独立行政法人物質・材料研究機構 | 骨誘導能ないしは伝導能を有する薬剤徐放可能な生体活性生体吸収型有機無機複合体 |
-
1987
- 1987-05-18 US US07/050,860 patent/US4786753A/en not_active Expired - Fee Related
-
1988
- 1988-10-05 EP EP88309255A patent/EP0362443B1/en not_active Expired - Lifetime
- 1988-10-05 ES ES88309255T patent/ES2047557T3/es not_active Expired - Lifetime
- 1988-10-18 KR KR1019880013548A patent/KR960015910B1/ko not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2047557T3 (es) | 1994-03-01 |
| US4786753A (en) | 1988-11-22 |
| EP0362443B1 (en) | 1994-01-12 |
| EP0362443A1 (en) | 1990-04-11 |
| KR960015910B1 (ko) | 1996-11-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19881018 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19931018 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19881018 Comment text: Patent Application |
|
| G160 | Decision to publish patent application | ||
| PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19961030 |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19970213 |
|
| NORF | Unpaid initial registration fee | ||
| PC1904 | Unpaid initial registration fee |