KR950008467A - 고순도 벤젠디카르복실산 이성질체의 제조방법 - Google Patents
고순도 벤젠디카르복실산 이성질체의 제조방법 Download PDFInfo
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- KR950008467A KR950008467A KR1019930021276A KR930021276A KR950008467A KR 950008467 A KR950008467 A KR 950008467A KR 1019930021276 A KR1019930021276 A KR 1019930021276A KR 930021276 A KR930021276 A KR 930021276A KR 950008467 A KR950008467 A KR 950008467A
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- oxidation reaction
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- oxidation
- postoxidation
- carboxylic acid
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- 238000000034 method Methods 0.000 title claims abstract description 39
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 title claims abstract 7
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 48
- 238000000605 extraction Methods 0.000 claims abstract description 28
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims abstract 13
- 239000003054 catalyst Substances 0.000 claims abstract 11
- 239000002002 slurry Substances 0.000 claims abstract 10
- 229910001385 heavy metal Inorganic materials 0.000 claims abstract 8
- ZBICJTQZVYWJPB-UHFFFAOYSA-N [Mn].[Co].[Br] Chemical class [Mn].[Co].[Br] ZBICJTQZVYWJPB-UHFFFAOYSA-N 0.000 claims abstract 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 6
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000007789 gas Substances 0.000 claims abstract 3
- 238000010438 heat treatment Methods 0.000 claims abstract 3
- 239000012535 impurity Substances 0.000 claims abstract 3
- 150000003738 xylenes Chemical class 0.000 claims abstract 3
- 229910052684 Cerium Inorganic materials 0.000 claims abstract 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052804 chromium Inorganic materials 0.000 claims abstract 2
- 239000011651 chromium Substances 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 150000002736 metal compounds Chemical class 0.000 claims abstract 2
- 229910052759 nickel Inorganic materials 0.000 claims abstract 2
- 229910052726 zirconium Inorganic materials 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims 6
- 229910017052 cobalt Inorganic materials 0.000 claims 4
- 239000010941 cobalt Substances 0.000 claims 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 4
- 239000011541 reaction mixture Substances 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 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 3
- -1 manganese-bromine compound Chemical class 0.000 claims 3
- 238000004064 recycling Methods 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000010586 diagram Methods 0.000 description 2
Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/14—Monocyclic dicarboxylic acids
- C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
- C07C63/26—1,4 - Benzenedicarboxylic acid
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- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
본 발명은 고순도의 벤젠디카르복실산 이성질체를 제조하는 개량된 방법을 제공하며, 이 방법은 (a) 자일렌 이성질체를 저급 지방족카르복실산 용매내에서 코발트-망간-브롬 화합물과 니켈, 크롬, 지르코늄 및 세륨 중에서 선택된 적어도 1종 이상의 중금속 화합물로 이루어진 촉매계를 이용하여 분자상 산소 또는 분자상 산소함유 가스로 산화시키는 산화반응공정을 1회 또는 2회 실시하고; 및 (b) 상기 산화반응공정의 산화 반응생성물을 결정화하여 조(租) 벤젠디카르복실산 이성질체의 케이크를 분리하고, 저급 지방족 카르복실산 용액을 상기 케이크에 첨가하여 재슬러리화한 후 가열하여 불순물을 용액상으로 추출해내고, 얻어진 전체 슬러리를 상기한 촉매 존재하에서 상기 가열 추출공정의 온도보다 적어도 2-80℃낮은 온도에서 산화시키는 추출/후산화공정을 1회 또는 2회 실시하는 것을 포함함을 특징으로 한다. 또한 본 발명에 따르면 상기의 산화반응공정 및 추출/후산화 공정을 최소한 총 3회 이상 실시해야 한다.
본 발명의 방법에 따르면, 불순물인 CBA의 농도가 25ppm미만인 고순도의 벤젠디카르복실산을 보다 경제적인 방법으로 신속하게 제조할 수 있다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 본 발명의 방법에 따라 제1 및 제2산화반응 공정후에 추출/후산화 공정을 1회 실시하는 경우(방법 제1)의 반응 공정도이고;
제2도는 본 발명의 방법에 따라 제1 및 제2산화반응 공정후에 추출/후산화 공정을 2회 실시하는 경우(방법 제2)의 반응 공정도이며;
제3도는 본 발명의 방법에 따라 제1산화반응 공정후에 추출/후산화반응 공정을 2회 실시하는 경우(방법 제3)의 반응 공정도이다.
Claims (19)
- 자일렌 이성질체를 액상에서 촉매 존재하에 분자상 산소 또는 분자상 산소 함유 가스로 산화시켜 벤젠디카르복실산 이성질체를 제조하는 방법에 있어서, (a) 자일렌 이성질체를 저급 지방족카르복실산 용매내에서 코발트-망간-브롬 화합물과 니켈, 크롬, 지르코늄 및 세륨 중에서 선택된 적어도 1종 이상의 중금속 화합물로 이루어진 촉매계를 이용하여 분자상 산소 또는 분자상 산소함유 가스로 산화시키는 산화반응공정을 1회 또는 2회 실시하고; 및 (b) 상기 산화반응 공정의 생성물을 결정화하여 조(租) 벤젠디카르복실산 이성질체의 케이크를 분리하고, 저급 지방족 카르복실산 용액을 상기 케이크에 첨가하여 재슬러리화한 후 200-280℃의 온도로 5-60분간 가열하여 불순물을 용액상으로 추출해내고, 얻어진 전체 슬러리를 상기한 산화반응 공정(a)에서의 촉매 존재하에서 상기 가열 추출공정의 온도보다 적어도 2-80℃낮은 온도에서 산화시키는 추출/후산화공정을 1회 또는 2회 실시하며, (a)와(b)의 공정을 합한 총 실시횟수를 3회 이상으로 함을 특징으로 하는 고순도 벤젠디카르복실산 이성질체의 제조방법.
- 제1항에 있어서, (a)의 산화반응 공정을 2회 실시하고(제1 및 제2산화반응 공정), (b)의 추출/후산화 공정을 1회 실시하는 (제1추출/후산화반응 공정) 것을 특징으로 하는 방법.
- 제1항에 있어서, (a)의 산화반응 공정을 2회 실시하고(제1 및 제2산화반응 공정), (b)의 추출/후산화 공정을 2회 실시하는 (제1 및 제2추출/후산화반응 공정) 것을 특징으로 하는 방법.
- 제1항에 있어서, (a)의 산화반응 공정을 1회 실시하고(제1산화반응 공정), (b)의 추출/후산화 공정을 2회 실시하는 (제1 및 제2추출/후산화반응 공정) 것을 특징으로 하는 방법.
- 제2항 내지 제4항중 어느 한 항에 있어서, 제1산화반응을 위해 반응기로 투입시키는 반응혼합물을 미리 150℃이상, 산화반응의 온도 이하의 온도에서 선가열하는 것을 특징으로 하는 방법.
- 제2항에 있어서, 2회째의 산화반응 공정(제2산화반응 공정) 후 얻어지는 슬러리로부터 분리하여 얻은 케이크의 재슬러리화에 사용되는 저급 지방족 카르복실산 용액으로는, 1회째의 추출/후산화 반응 공정(제1추출/후산화반응 공정)에서 얻어지는 케이크를 세척하는데 사용된 저급 지방족 카르복실산을 재순환하여 사용하는 것을 특징으로 하는 방법.
- 제3항에 있어서, 2회째의 산화반응 공정(제2산화반응 공정) 후 얻어지는 슬러리로부터 분리하여 얻은 케이크의 재슬러리화에 사용되는 저급 지방족 카르복실산 용액으로는, 2회째의 추출/후산화 반응 공정(제2추출/후산화반응 공정)에서 얻어지는 슬러리를 분리하여 얻은 저급 지방족 카르복실산을 재순환하여 사용하고, 1회째의 추출/후산화반응 공정(제1추출/후산화반응 공정) 후 얻어지는 슬러리로부터 분리하여 얻은 케이크의 재슬러리화에 사용되는 저급 지방족 카르복실산 용액으로는, 2회째의 추출/후산화 반응 공정(제2추출/후산화반응 공정)에서 얻어지는 케이크를 세척하는데 사용된 저급 지방족 카르복실산을 재순환하여 사용하는 것을 특징으로 하는 방법.
- 제4항에 있어서, 1회째의 산화반응 공정(제1산화반응 공정) 후 얻어지는 슬러리로부터 분리하여 얻은 케이크의 재슬러리화에 사용되는 저급 지방족 카르복실산 용액으로는, 2회째의 추출/후산화 반응 공정(제2추출/후산화반응 공정)에서 얻어지는 슬러리를 분리하여 얻은 저급 지방족 카르복실산을 재순환하여 사용하고, 1회째의 추출/후산화반응 공정(제1추출/후산화반응 공정) 후 얻어지는 슬러리로부터 분리하여 얻은 케이크의 재슬러리화에 사용되는 저급 지방족 카르복실산 용액으로는, 2회째의 추출/후산화 반응 공정(제2추출/후산화반응 공정)에서 얻어지는 케이크를 세척하는데 사용된 저급 지방족 카르복실산을 재순환하여 사용하는 것을 특징으로 하는 방법.
- 제2항 또는 제3항에 있어서, 제1산화반응 및 제2산화반응은 150-230℃의 온도에서 20-60분간 실시함을 특징으로 하는 방법.
- 제4항에 있어서, 제1산화반응은 150-230℃의 온도에서 20-60분간 실시함을 특징으로 하는 방법.
- 제2항 내지 제4항중 어느 한 항에 있어서, 제1산화반응을 위해 반응기로 투입시키는 반응혼합물의 유입속도는 6-30m/s이고, 투입방향은 반응기내부의 기존 반응혼합물의 회전방향의 반대임을 특징으로 하는 방법.
- 제2항에 있어서, 코발트-망간-브롬 촉매계에 첨가되는 중금속의 농도는 코발트와 망간을 합한 농도에 대해서 0.01-0.2의 비율이고, 첨가되는 총 농도는 50-300ppm임을 특징으로 하는 방법.
- 제2항에 있어서, 코발트-망간-브롬 촉매계에 첨가되는 중금속의 양은 제1산화반응:제2산화반응:제1후산화반응의 농도비가 1:0.5-0.9:0.05-0.2임을 특징으로 하는 방법.
- 제3항에 있어서, 코발트-망간-브롬 촉매계에 첨가되는 중금속의 농도는 코발트와 망간을 합한 농도에 대해서 0.01-0.2의 비율이고, 첨가되는 총 농도는 30-200ppm임을 특징으로 하는 방법.
- 제3항에 있어서, 코발트-망간-브롬 촉매계에 첨가되는 중금속의 양은 제1산화반응 : 제2산화반응 : 제1후산화반응 : 제2후산화반응의 농도비가 1:0.5-0.9:0.1-0.3:0.05-0.2임을 특징으로 하는 방법.
- 제4항에 있어서, 코발트-망간-브롬 촉매계에 첨가되는 중금속의 농도는 코발트와 망간을 합한 농도에 대해서 0.01-0.2의 비율이고, 첨가되는 총 농도는 40-300ppm임을 특징으로 하는 방법.
- 제4항에 있어서, 코발트-망간-브롬 촉매계에 첨가되는 중금속의 양은 제1산화반응:제2산화반응:제2후산화반응의 농도비가 1:0.05-0.5:0.05-0.2임을 특징으로 하는 방법.
- 제1항에 있어서, 브롬 화합물은 브롬 화합물 또는 브롬 화합물과 염소 화합물의 혼합물이며, 후자의 경우 브롬:염소의 농도비가 1:0.001-0.5임을 특징으로 하는 방법.
- 제6항 내지 제8항중 어느 한 항에 있어서, 재슬러리화에 사용되는 옹매의 양은 처리전의 슬러리중에 포함되어 있는 용매 전체 중량의 적어도 60%이상이 교환될 수 있는 양인 것을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
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| RU93046191 | 1993-09-28 | ||
| RU93046190 | 1993-09-28 | ||
| RU93046190/04A RU2047594C1 (ru) | 1993-09-28 | 1993-09-28 | Способ получения изомеров бензолдикарбоновых кислот с высокой степенью очистки |
| RU93046191/04A RU2047595C1 (ru) | 1993-09-28 | 1993-09-28 | Способ получения изомеров фталевых кислот с высокой степенью чистоты |
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| Publication Number | Publication Date |
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| KR950008467A true KR950008467A (ko) | 1995-04-17 |
| KR970000136B1 KR970000136B1 (ko) | 1997-01-04 |
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| KR1019930021276A KR970000136B1 (ko) | 1993-09-28 | 1993-10-14 | 고순도 벤젠디카르복실산 이성질체의 제조방법 |
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| US (1) | US5359133A (ko) |
| JP (1) | JP3009223B2 (ko) |
| KR (1) | KR970000136B1 (ko) |
| CN (1) | CN1050118C (ko) |
| AU (1) | AU5576394A (ko) |
| BE (1) | BE1008546A4 (ko) |
| BG (1) | BG62324B1 (ko) |
| BR (1) | BR9305996A (ko) |
| CA (1) | CA2128719C (ko) |
| DE (2) | DE4397599T1 (ko) |
| ES (1) | ES2081265B1 (ko) |
| FR (1) | FR2710638B1 (ko) |
| GB (1) | GB2286588B (ko) |
| IT (1) | IT1271011B (ko) |
| MY (1) | MY108978A (ko) |
| PL (1) | PL175685B1 (ko) |
| RO (1) | RO113850B1 (ko) |
| SA (1) | SA94140587B1 (ko) |
| SK (1) | SK280582B6 (ko) |
| TW (1) | TW307753B (ko) |
| WO (1) | WO1995009143A1 (ko) |
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- 1993-10-14 KR KR1019930021276A patent/KR970000136B1/ko not_active IP Right Cessation
- 1993-10-27 US US08/141,738 patent/US5359133A/en not_active Expired - Lifetime
- 1993-11-30 AU AU55763/94A patent/AU5576394A/en not_active Abandoned
- 1993-11-30 JP JP6516877A patent/JP3009223B2/ja not_active Expired - Lifetime
- 1993-11-30 DE DE4397599T patent/DE4397599T1/de active Pending
- 1993-11-30 GB GB9415915A patent/GB2286588B/en not_active Expired - Lifetime
- 1993-11-30 BR BR9305996A patent/BR9305996A/pt not_active IP Right Cessation
- 1993-11-30 CA CA002128719A patent/CA2128719C/en not_active Expired - Lifetime
- 1993-11-30 DE DE4397599A patent/DE4397599C2/de not_active Expired - Lifetime
- 1993-11-30 ES ES09450020A patent/ES2081265B1/es not_active Expired - Fee Related
- 1993-11-30 PL PL93308537A patent/PL175685B1/pl unknown
- 1993-11-30 RO RO94-01218A patent/RO113850B1/ro unknown
- 1993-11-30 WO PCT/KR1993/000106 patent/WO1995009143A1/en active Application Filing
- 1993-11-30 SK SK877-94A patent/SK280582B6/sk not_active IP Right Cessation
- 1993-12-30 MY MYPI93002874A patent/MY108978A/en unknown
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1994
- 1994-01-12 CN CN94100679A patent/CN1050118C/zh not_active Expired - Lifetime
- 1994-01-20 TW TW083100473A patent/TW307753B/zh not_active IP Right Cessation
- 1994-03-06 SA SA94140587A patent/SA94140587B1/ar unknown
- 1994-07-20 BG BG98919A patent/BG62324B1/bg unknown
- 1994-07-26 BE BE9400702A patent/BE1008546A4/nl not_active IP Right Cessation
- 1994-09-14 IT ITMI941879A patent/IT1271011B/it active IP Right Grant
- 1994-09-21 FR FR9411253A patent/FR2710638B1/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE4397599C2 (de) | 1998-02-19 |
| BG62324B1 (bg) | 1999-08-31 |
| BG98919A (bg) | 1995-05-31 |
| IT1271011B (it) | 1997-05-26 |
| BE1008546A4 (nl) | 1996-06-04 |
| GB9415915D0 (en) | 1995-05-24 |
| SK280582B6 (sk) | 2000-04-10 |
| PL175685B1 (pl) | 1999-01-29 |
| GB2286588A (en) | 1995-08-23 |
| SA94140587B1 (ar) | 2006-11-12 |
| DE4397599T1 (de) | 1997-07-24 |
| BR9305996A (pt) | 1997-10-21 |
| JPH08506571A (ja) | 1996-07-16 |
| PL308537A1 (en) | 1995-08-21 |
| RO113850B1 (ro) | 1998-11-30 |
| FR2710638B1 (fr) | 1996-04-26 |
| ITMI941879A1 (it) | 1996-03-14 |
| ES2081265A1 (es) | 1996-02-16 |
| KR970000136B1 (ko) | 1997-01-04 |
| SK87794A3 (en) | 1995-05-10 |
| CN1050118C (zh) | 2000-03-08 |
| WO1995009143A1 (en) | 1995-04-06 |
| FR2710638A1 (fr) | 1995-04-07 |
| MY108978A (en) | 1996-11-30 |
| CN1103860A (zh) | 1995-06-21 |
| JP3009223B2 (ja) | 2000-02-14 |
| CA2128719A1 (en) | 1995-03-29 |
| ITMI941879A0 (it) | 1994-09-14 |
| CA2128719C (en) | 1998-06-09 |
| US5359133A (en) | 1994-10-25 |
| TW307753B (ko) | 1997-06-11 |
| ES2081265B1 (es) | 1996-10-16 |
| GB2286588B (en) | 1996-09-11 |
| AU5576394A (en) | 1995-04-18 |
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