JP2005526718A - フェノールの精製方法及び触媒 - Google Patents
フェノールの精製方法及び触媒 Download PDFInfo
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- hydroxide
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- 239000003054 catalyst Substances 0.000 title claims abstract description 51
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000000746 purification Methods 0.000 title claims description 18
- 239000000203 mixture Substances 0.000 claims abstract description 28
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims abstract description 14
- ZGUQGPFMMTZGBQ-UHFFFAOYSA-N [Al].[Al].[Zr] Chemical compound [Al].[Al].[Zr] ZGUQGPFMMTZGBQ-UHFFFAOYSA-N 0.000 claims abstract description 13
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical group OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 8
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 claims abstract description 7
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910001928 zirconium oxide Inorganic materials 0.000 claims abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- IVORCBKUUYGUOL-UHFFFAOYSA-N 1-ethynyl-2,4-dimethoxybenzene Chemical compound COC1=CC=C(C#C)C(OC)=C1 IVORCBKUUYGUOL-UHFFFAOYSA-N 0.000 claims description 14
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 13
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 claims description 11
- 229910001593 boehmite Inorganic materials 0.000 claims description 11
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 6
- 238000001935 peptisation Methods 0.000 claims description 5
- HAIMOVORXAUUQK-UHFFFAOYSA-J zirconium(iv) hydroxide Chemical class [OH-].[OH-].[OH-].[OH-].[Zr+4] HAIMOVORXAUUQK-UHFFFAOYSA-J 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 230000001180 sulfating effect Effects 0.000 claims description 4
- 230000019635 sulfation Effects 0.000 claims description 4
- 238000005670 sulfation reaction Methods 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 2
- 238000001125 extrusion Methods 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 10
- -1 aromatic carbonyl compounds Chemical class 0.000 abstract description 4
- ZXAUZSQITFJWPS-UHFFFAOYSA-J zirconium(4+);disulfate Chemical compound [Zr+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZXAUZSQITFJWPS-UHFFFAOYSA-J 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract description 3
- 125000001931 aliphatic group Chemical group 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 19
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 10
- 229940024545 aluminum hydroxide Drugs 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- GBGPVUAOTCNZPT-UHFFFAOYSA-N 2-Methylcumarone Chemical compound C1=CC=C2OC(C)=CC2=C1 GBGPVUAOTCNZPT-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 7
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 4
- 239000011812 mixed powder Substances 0.000 description 4
- 229910001388 sodium aluminate Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 2
- 150000004645 aluminates Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- CMOAHYOGLLEOGO-UHFFFAOYSA-N oxozirconium;dihydrochloride Chemical compound Cl.Cl.[Zr]=O CMOAHYOGLLEOGO-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000005406 washing Methods 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
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/053—Sulfates
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
- B01J37/031—Precipitation
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
【解決手段】 脂肪族及び芳香族カルボニル化合物の混合物を含有するフェノールをアルミニウムジルコニウム触媒を用いて精製する。アルミニウムジルコニウム触媒はジルコニウムの酸化物及び硫酸塩の混合物を含んでおり、硫酸アルミニウムと硫酸ジルコニウムの合計含有率は5〜15質量%(SO4に基づいて計算)であり、酸化アルミニウムと硫酸アルミニウムの合計含有率は5〜30質量%(酸化アルミニウムに基づいて計算)である。本プロセスは、90〜200℃の温度で、触媒床を通る相対的な原料体積供給速度を空間速度1〜3h-1とするのに必要なレベルに維持して実施される。本発明の触媒との接触で得られるフェノールを蒸留すると、実際上純粋なフェノールを単離することができる。
Description
[ソ連特許第1559494号(1986)、ロシア連邦特許第2058189号 (ロシア特許庁公報誌第11号、4/20/96)]。
a)触媒の調製
431gのZrOCl2・8H2O塩を蒸留水5.2Lに溶解する。得られた溶液に濃度約25%のNH4OH溶液332mLを20分かけて滴下する。得られた沈殿をブフナー漏斗で濾過し、水洗して塩化アンモニウムを除去する。洗浄した沈殿を110℃の乾燥キャビネットで24時間乾燥する。乾燥した沈殿をミルで粉砕し、得られた微粉末を180μmの篩いにかける。粉末の質量は190gであり、ZrO2に換算すると147gである。
得られたアルミニウムジルコニウム触媒のフェノール精製プロセスに関する試験を、フロースルー実験室用装置において温度100℃、原料体積供給速度1.5h-1で実施した。以下の表に、クミルヒドロペルオキシドの分解で得られ、精製原料として供したフェノールの組成と、上記の通り製造した触媒を用いて精製した生成物の組成を示す。
触媒を実施例1と同様に製造するが、水酸化アルミニウム混合粉末中のベーマイトと擬ベーマイトの比は3:1である(Al2O3に基づいて計算)。水酸化ジルコニウム沈殿は硫酸溶液380mLで硫酸化する。硫酸化した水酸化ジルコニウム粉末と混合する水酸化アルミニウム混合粉末の量は13.9gである。その他のパラメータは実施例1と同一である。
製造法と組成を実施例1に記載したアルミニウムジルコニウム触媒から試料を取った。試験を、温度90℃、原料体積供給速度V=1h-1で上述の通り実施した。得られたフェノールは以下の組成(ppm単位):HA<1;α−メチルスチレン<1;2−メチルベンゾフラン−58;OM<5;AP<1;DMPC<1を有していた。
製造法と組成を実施例2に記載したアルミニウムジルコニウム触媒から試料を取った。試験を、温度200℃、原料体積供給速度V=1.5h-1で上述の通り実施した。得られたフェノールは以下の組成(ppm単位):HA<1;α−メチルスチレン<1;2−メチルベンゾフラン−31;OM<5;AP<1;DMPC<1を有していた。
Claims (11)
- クミルヒドロペルオキシド分解法で生成した粗製フェノールを精製する方法であって、当該方法が、(i)粗製フェノールを90〜200℃の温度、1〜6h-1の原料体積供給速度で酸性酸化アルミニウム触媒と接触させ、(ii)その後、蒸留で精製したフェノールを単離することを含んでなり、上記酸化アルミニウム触媒がアルミニウム及びジルコニウムの酸化物及び硫酸塩の混合物を含み、硫酸アルミニウムと硫酸ジルコニウムの合計含有率が5〜15質量%(SO4イオンに基づいて計算)であり、触媒の酸化アルミニウムと硫酸アルミニウムの合計含有率が5〜30質量%(酸化アルミニウムに基づいて計算)ある、方法。
- 前記触媒が実質的にアルミニウム及びジルコニウムの酸化物及び硫酸塩の混合物からなる、請求項1記載の方法。
- 前記触媒が請求項1記載の方法によって製造される、請求項2記載の方法。
- フェノールの精製に適したアルミニウムジルコニウム触媒の製造方法であって、硫酸化段階と解膠段階の両段階において水酸化ジルコニウムを硫酸を用いて2度処理し、質量比1:3〜3:1のベーマイトと擬ベーマイトの混合物からなる酸化アルミニウムを使用する、方法。
- 前記解膠剤が硫酸の水溶液である、請求項4記載の方法。
- 前記水酸化アルミニウムが質量比1:3〜3:1のベーマイトと擬ベーマイトの混合物である、請求項5記載の方法。
- 前記フェノールの精製に適したアルミニウムジルコニウム触媒の製造方法であって、
a)水酸化ジルコニウムを沈澱させ、
b)水酸化アルミニウムを上記水酸化ジルコニウムを混合し、
c)水酸化ジルコニウムを硫酸化し、
d)水酸化ジルコニウムと硫酸化した水酸化ジルコニウムを解膠剤で解膠し、
e)次に、解膠した水酸化物混合物をスクリュー押出し、
f)押出混合物を加熱処理する
ことを含んでなる、方法。 - 前記解膠剤が硫酸の水溶液である、請求項7記載の方法。
- 前記水酸化アルミニウムが質量比1:3〜3:1のベーマイトと擬ベーマイトの混合物である、請求項8記載の方法。
- 第一の硫酸化段階及び第二の解膠段階において硫酸を用いて水酸化ジルコニウムを2度処理し、解膠段階で酸化アルミニウムを添加する段階を含んでなり、酸化アルミニウムが質量比1:3〜3:1のベーマイトと擬ベーマイトの混合物からなる方法によって製造される、フェノールの精製に適した触媒。
- a)水酸化ジルコニウムを沈澱させ、
b)水酸化アルミニウムを水酸化ジルコニウムと混合し、
c)水酸化ジルコニウムを硫酸化し、
d)水酸化ジルコニウムと硫酸化した水酸化ジルコニウムを解膠剤で解膠し、
e)次に、解膠した水酸化物混合物をスクリュー押出し、
f)押出混合物を加熱処理する
段階を含んでなる、フェノールの精製に適した触媒。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
RU2002103669/04A RU2217408C2 (ru) | 2002-02-08 | 2002-02-08 | Способ и катализатор очистки фенола |
US10/354,270 US7102036B2 (en) | 2002-02-08 | 2003-01-30 | Process and catalyst for purifying phenol |
PCT/US2003/003090 WO2003066554A1 (en) | 2002-02-08 | 2003-02-03 | Process and catalyst for purifying phenol |
Publications (1)
Publication Number | Publication Date |
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JP2005526718A true JP2005526718A (ja) | 2005-09-08 |
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JP2003565931A Pending JP2005526718A (ja) | 2002-02-08 | 2003-02-03 | フェノールの精製方法及び触媒 |
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US (1) | US20060129003A1 (ja) |
EP (1) | EP1476413A1 (ja) |
JP (1) | JP2005526718A (ja) |
CN (1) | CN100457703C (ja) |
AU (1) | AU2003222202A1 (ja) |
WO (1) | WO2003066554A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2013154147A1 (ja) * | 2012-04-13 | 2013-10-17 | 三井化学株式会社 | フェノールの精製方法 |
JP2015017058A (ja) * | 2013-07-11 | 2015-01-29 | 三井化学株式会社 | フェノールの精製方法 |
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AU2005212396A1 (en) | 2004-02-06 | 2005-08-25 | Bayer Healthcare Llc | Oxidizable species as an internal reference for biosensors and method of use |
JP5385607B2 (ja) | 2005-07-20 | 2014-01-08 | バイエル・ヘルスケア・エルエルシー | ゲート化電流測定器 |
RU2426107C2 (ru) | 2005-09-30 | 2011-08-10 | БАЙЕР ХЕЛТКЭА ЭлЭлСи | Вольтамперометрический способ определения концентрации аналита в образце и устройство для определения концентрации аналита |
EP2679150B1 (en) | 2006-10-24 | 2020-07-22 | Ascensia Diabetes Care Holdings AG | Transient decay amperometry |
WO2009076302A1 (en) | 2007-12-10 | 2009-06-18 | Bayer Healthcare Llc | Control markers for auto-detection of control solution and methods of use |
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- 2003-02-03 WO PCT/US2003/003090 patent/WO2003066554A1/en active Application Filing
- 2003-02-03 CN CNB038035812A patent/CN100457703C/zh not_active Expired - Fee Related
- 2003-02-03 AU AU2003222202A patent/AU2003222202A1/en not_active Abandoned
- 2003-02-03 JP JP2003565931A patent/JP2005526718A/ja active Pending
- 2003-02-03 EP EP03717881A patent/EP1476413A1/en not_active Withdrawn
-
2006
- 2006-02-01 US US11/344,780 patent/US20060129003A1/en not_active Abandoned
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013154147A1 (ja) * | 2012-04-13 | 2013-10-17 | 三井化学株式会社 | フェノールの精製方法 |
US9029609B2 (en) | 2012-04-13 | 2015-05-12 | Mitsui Chemicals, Inc. | Phenol purification process |
JPWO2013154147A1 (ja) * | 2012-04-13 | 2015-12-17 | 三井化学株式会社 | フェノールの精製方法 |
JP2015017058A (ja) * | 2013-07-11 | 2015-01-29 | 三井化学株式会社 | フェノールの精製方法 |
Also Published As
Publication number | Publication date |
---|---|
US20060129003A1 (en) | 2006-06-15 |
AU2003222202A1 (en) | 2003-09-02 |
WO2003066554A1 (en) | 2003-08-14 |
CN1630626A (zh) | 2005-06-22 |
EP1476413A1 (en) | 2004-11-17 |
CN100457703C (zh) | 2009-02-04 |
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