KR940703798A - 하이드록시 방향족화합물의 제조방법 - Google Patents
하이드록시 방향족화합물의 제조방법Info
- Publication number
- KR940703798A KR940703798A KR1019940702312A KR19940702312A KR940703798A KR 940703798 A KR940703798 A KR 940703798A KR 1019940702312 A KR1019940702312 A KR 1019940702312A KR 19940702312 A KR19940702312 A KR 19940702312A KR 940703798 A KR940703798 A KR 940703798A
- Authority
- KR
- South Korea
- Prior art keywords
- producing
- acid
- hydroperoxides
- aromatic compound
- hydroxy aromatic
- 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
- -1 hydroxy aromatic compound Chemical class 0.000 title claims abstract 18
- 238000000034 method Methods 0.000 title claims abstract 6
- 238000004519 manufacturing process Methods 0.000 claims abstract 16
- 150000001875 compounds Chemical class 0.000 claims abstract 9
- 239000003377 acid catalyst Substances 0.000 claims abstract 8
- 239000002253 acid Substances 0.000 claims abstract 7
- 238000006243 chemical reaction Methods 0.000 claims abstract 5
- 239000011541 reaction mixture Substances 0.000 claims abstract 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract 3
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 claims abstract 3
- 238000000354 decomposition reaction Methods 0.000 claims abstract 2
- 150000002978 peroxides Chemical class 0.000 claims abstract 2
- 150000002432 hydroperoxides Chemical class 0.000 claims 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 claims 3
- SBUBPFHJZHQNNT-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene hydrogen peroxide Chemical compound OO.OO.CC(C)C1=CC=CC=C1C(C)C SBUBPFHJZHQNNT-UHFFFAOYSA-N 0.000 claims 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 3
- OXGNOOBROBDQFE-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene hydrogen peroxide Chemical compound OO.C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 OXGNOOBROBDQFE-UHFFFAOYSA-N 0.000 claims 2
- WRJDXIDFGOPHNQ-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene hydrogen peroxide Chemical compound OO.OO.C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 WRJDXIDFGOPHNQ-UHFFFAOYSA-N 0.000 claims 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims 2
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 claims 2
- MRIZMKJLUDDMHF-UHFFFAOYSA-N cumene;hydrogen peroxide Chemical class OO.CC(C)C1=CC=CC=C1 MRIZMKJLUDDMHF-UHFFFAOYSA-N 0.000 claims 2
- HNGMGIQYDOKAMH-UHFFFAOYSA-N hydrogen peroxide 2-methyl-1-propan-2-ylnaphthalene Chemical compound OO.C1=CC=C2C(C(C)C)=C(C)C=CC2=C1 HNGMGIQYDOKAMH-UHFFFAOYSA-N 0.000 claims 2
- QBEZHXMLBPSPCU-UHFFFAOYSA-N hydrogen peroxide;1-propan-2-ylnaphthalene Chemical compound OO.C1=CC=C2C(C(C)C)=CC=CC2=C1 QBEZHXMLBPSPCU-UHFFFAOYSA-N 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- 125000005650 substituted phenylene group Chemical group 0.000 claims 2
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- RRCMEPHKTHMOKV-UHFFFAOYSA-N cumene;hydrogen peroxide Chemical compound OO.OO.CC(C)C1=CC=CC=C1 RRCMEPHKTHMOKV-UHFFFAOYSA-N 0.000 claims 1
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 abstract 4
- 239000006227 byproduct Substances 0.000 abstract 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/04—Phenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (15)
- 일반식(I)(상기식 중, n은 1 또는 2의 정수를 나타내고, Ar은 n가의 방향족탄화수소기를 나타낸다.)로 표시되는 하이드로퍼옥사이드류를 산촉매의 존재하에 산분해하여, 일반식(Ⅱ)Ar-(OH)n (Ⅱ)(식중, Ar 및 n은 상기와 똑같다.)로 표시되는 하이드록시방향족화합물을 제조하는 방법에 있어서, 산촉매로서, 테트라플루오로붕산, 헥사플루오로규산 또는 헥사플루오로인산을 사용하는 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 제1항 내지 3항 중의 어느 한 항에 있어서, 산촉매를 반응혼합물에서, 20ppm 내지 5중량%의 범위에서 사용하는 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 제1항 내지 4항 중의 어느 한 항에 있어서, 일반식(I)에서, n이 1일 때, Ar이 페닐기 또는 치환페닐이기고, n이 2일 때, Ar이 페닐렌기, 치환페닐렌기, 나프탈렌기 또는 치환나프탈렌기인 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 제1항 또는 2항에 있어서, 하이드로퍼옥사이드류가 쿠멘하이드로퍼옥사이드, 사이멘하이드로퍼옥사이드, 디이소프로필벤젠모노하이드로퍼옥사이드, 트리이소프로필벤젠모노하이드로퍼옥사이드, 이소프로필나프탈렌하이드로퍼옥사이드, 메틸이소프로필나프탈렌모노하드로퍼옥사이드, 디이소프로필나프탈렌모노하이드로퍼옥사이드, 디이소프로필벤젠디하이드로퍼옥사이드, 트리이소프로필벤젠디하이드로퍼옥사이드 또는 디이소프로필나프탈렌디하이드로퍼옥사이드인 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 제1항 또는 2항에 있어서, 하이드로퍼옥사이드류가 쿠멘하이드로퍼옥사이드인 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 제1항 또는 2항에 있어서 하이드로퍼옥사이드류가 사이멘하이드로퍼옥사이드인 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 제1항 또는 2항에 있어서, 하이드로퍼옥사이드류가 이소프로필벤젠디하이드로퍼옥사이드인 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 일반식(I)(상기식 중, n은 1또는 2의 정수를 나타내고, Ar은 n가의 방향족탄화수소기를 나타낸다.)로 표시되는 하이토록퍼옥사이드류를 산촉매의 존재하에서 산분해하여, 일반식(Ⅱ)Ar-(OH)n (Ⅱ)(식중, Ar 및 n은 상기와 같다.)로 표시되는 하이드록시방향족화합물을 제조하는 방법에 있어서, 산촉매로서, 테트라풀루오로붕산, 헥사플루오로규산 또는 헥사플루오로인산을 사용하는 동시에, 상기 산분해반응을 제1단으로서 제1반응기에 있어서 온도 50℃ 내지 95℃에서 행하고, 얻어진 반응혼합물을 제2반응기에 있어서, 제2단으로서 온도 80℃ 내지 120℃에서 행하는 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 제8항에 있어서, 잔존하는 하이드로퍼옥사이드농도가 1중량%이하로 저하된 시점에서 제1단의 반응을 정지하고, 이어서, 제2단의 반응을 잔존하이드로퍼옥사이드농도가 0.1중량%이하로 되도록 행하는 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 제8항 또는 제9항에 있어서, 산촉매를 반응혼합물에 있어서 20ppm 내지 5중량%의 범위로 사용하는 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 제8항 내지 10항중의 어느 한 항에 있어서, 일반식에서, n이 1일 때, Ar이 페닐렌기 또는 치환페닐기이고, n이 2일 때, Ar이 페닐기, 치환페닐렌기, 나프탈렌기 또는 치환나프탈렌기인 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 제8항 내지 10항중의 어느 한 항에 있어서, 하이드로퍼옥사이드류가 쿠멘하이드로퍼옥사이드, 사이멘하이드로퍼옥사이드, 디이소프로필벤젠모노하이드로퍼옥사이드, 트리이소프로필벤젠모노하이드로퍼옥사이드, 이소프로필나프탈렌하이드로퍼옥사이드, 메틸이소프로필나프탈렌모노하드로퍼옥사이드, 디이소프로필나프탈렌모노하이드로퍼옥사이드, 디이소프로필벤젠디하이드로퍼옥사이드, 트리이소프로필벤젠디하이드로퍼옥사이드 또는 디이소프로필나프탈렌디하이드로퍼옥사이드인 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 제8항 내지 10항 중의 어느 한 항에 있어서, 하이드로퍼옥사이드류가 쿠멘하이드로퍼옥사이드인 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.에 있어서, 하이드록시 방향족화합물의 제조방법.
- 제8항 내지 10항 중의 어느 한 항에 있어서, 하이드로퍼옥사이드류가 사이멘하이드로퍼옥사이드인 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.
- 제8항 내지 10중의 어느 한 항에 있어서, 하이드로퍼옥사이드류가 디이소프로필벤젠디하이드로퍼옥사이드인 것을 특징으로 하는 하이드록시방향족화합물의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29614692 | 1992-11-05 | ||
| JP92-296146 | 1992-11-05 | ||
| PCT/JP1993/001586 WO1994010115A1 (fr) | 1992-11-05 | 1993-11-01 | Procede de production d'un compose hydroxylique aromatique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR940703798A true KR940703798A (ko) | 1994-12-12 |
| KR100281849B1 KR100281849B1 (ko) | 2001-02-15 |
Family
ID=17829748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019940702312A Expired - Lifetime KR100281849B1 (ko) | 1992-11-05 | 1993-11-01 | 하이드록시 방향족화합물의 제조방법 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5475157A (ko) |
| EP (1) | EP0622350B1 (ko) |
| KR (1) | KR100281849B1 (ko) |
| CA (1) | CA2127375A1 (ko) |
| DE (1) | DE69318007T2 (ko) |
| WO (1) | WO1994010115A1 (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10110392A1 (de) * | 2001-03-03 | 2002-09-12 | Phenolchemie Gmbh & Co Kg | Verfahren zur Herstellung von Phenolen |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3376352A (en) * | 1963-02-21 | 1968-04-02 | Montedison Spa | Process for producing hydroquinone from p-dialkyl-benzene-bis-hydroperoxides |
| JPS4945854B1 (ko) * | 1969-06-18 | 1974-12-06 | ||
| US3720716A (en) * | 1970-06-12 | 1973-03-13 | Mitsui Petrochemical Ind | Process for preparation of cresol and acetone from cymene hydroperoxide |
| JPS4945854A (ko) * | 1972-09-08 | 1974-05-01 | ||
| JPS5050311A (ko) * | 1973-09-07 | 1975-05-06 | ||
| US4119791A (en) * | 1977-09-14 | 1978-10-10 | The Goodyear Tire & Rubber Company | Aqueous recovery of hydroquinone |
| US4267379A (en) * | 1978-12-04 | 1981-05-12 | Gulf Research & Development Company | Decomposition of cumene hydroperoxide and recovery of boron trifluoride catalyst |
| US4267380A (en) * | 1979-06-25 | 1981-05-12 | Gulf Research & Development Company | Decomposition of cumene hydroperoxide using a Lewis acid catalyst |
| US4339613A (en) * | 1980-03-14 | 1982-07-13 | Pcuk Produits Chimiques Ugine Kuhlmann | Superacid catalyzed preparation of resorcinol from meta-diisopropylbenzene |
| JPS6052733B2 (ja) * | 1980-12-05 | 1985-11-21 | 三井化学株式会社 | ヒドロキノンの製造方法 |
| US4358618A (en) * | 1981-06-22 | 1982-11-09 | Allied Corporation | Decomposition of cumene oxidation product |
| US4490566A (en) * | 1983-05-06 | 1984-12-25 | Mobil Oil Corporation | Production of phenol |
| JPS6084235A (ja) * | 1983-10-14 | 1985-05-13 | Mitsui Petrochem Ind Ltd | ｍ−ヒドロキシ置換フエノ−ル類の製法 |
| US4893995A (en) * | 1988-12-05 | 1990-01-16 | General Motors Corporation | Electric motor-driven impeller-type air pump |
-
1993
- 1993-11-01 KR KR1019940702312A patent/KR100281849B1/ko not_active Expired - Lifetime
- 1993-11-01 DE DE69318007T patent/DE69318007T2/de not_active Expired - Lifetime
- 1993-11-01 WO PCT/JP1993/001586 patent/WO1994010115A1/ja not_active Ceased
- 1993-11-01 US US08/256,245 patent/US5475157A/en not_active Expired - Lifetime
- 1993-11-01 CA CA002127375A patent/CA2127375A1/en not_active Abandoned
- 1993-11-01 EP EP93923680A patent/EP0622350B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR100281849B1 (ko) | 2001-02-15 |
| EP0622350A1 (en) | 1994-11-02 |
| EP0622350A4 (en) | 1994-12-21 |
| DE69318007D1 (de) | 1998-05-20 |
| CA2127375A1 (en) | 1994-05-11 |
| US5475157A (en) | 1995-12-12 |
| EP0622350B1 (en) | 1998-04-15 |
| DE69318007T2 (de) | 1998-09-17 |
| WO1994010115A1 (fr) | 1994-05-11 |
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