JPS58180448A - オルソ−フエニルフエノ−ル類の製造法 - Google Patents
オルソ−フエニルフエノ−ル類の製造法Info
- Publication number
- JPS58180448A JPS58180448A JP57063898A JP6389882A JPS58180448A JP S58180448 A JPS58180448 A JP S58180448A JP 57063898 A JP57063898 A JP 57063898A JP 6389882 A JP6389882 A JP 6389882A JP S58180448 A JPS58180448 A JP S58180448A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- catalyst
- alumina
- metal sulfate
- selectivity
- 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
- 235000010292 orthophenyl phenol Nutrition 0.000 title claims description 6
- -1 o-phenylphenol compound Chemical class 0.000 title abstract description 6
- LLEMOWNGBBNAJR-UHFFFAOYSA-N ortho-phenyl-phenol Natural products OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 27
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 13
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 9
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 12
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims description 8
- 229910052939 potassium sulfate Inorganic materials 0.000 claims description 8
- 235000011151 potassium sulphates Nutrition 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 150000005351 2-phenylphenols Chemical class 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 abstract 2
- 229910052936 alkali metal sulfate Inorganic materials 0.000 abstract 2
- 238000007142 ring opening reaction Methods 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 5
- 238000007598 dipping method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000010304 firing Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000005297 pyrex Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- NHMAFIMOCYQLOP-UHFFFAOYSA-N 2-(4-phenylphenyl)phenol Chemical compound OC1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 NHMAFIMOCYQLOP-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- UWXLYSVMPRLLJW-UHFFFAOYSA-N 3-phenyldibenzofuran Chemical compound C1=CC=CC=C1C1=CC=C2C3=CC=CC=C3OC2=C1 UWXLYSVMPRLLJW-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052925 anhydrite Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000004306 orthophenyl phenol Substances 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57063898A JPS58180448A (ja) | 1982-04-19 | 1982-04-19 | オルソ−フエニルフエノ−ル類の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57063898A JPS58180448A (ja) | 1982-04-19 | 1982-04-19 | オルソ−フエニルフエノ−ル類の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58180448A true JPS58180448A (ja) | 1983-10-21 |
| JPS6254409B2 JPS6254409B2 (enExample) | 1987-11-14 |
Family
ID=13242580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57063898A Granted JPS58180448A (ja) | 1982-04-19 | 1982-04-19 | オルソ−フエニルフエノ−ル類の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58180448A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104841421A (zh) * | 2015-04-15 | 2015-08-19 | 北京旭阳化工技术研究院有限公司 | 一种催化剂组合物、其制备方法及使用其制备邻苯基苯酚的方法 |
-
1982
- 1982-04-19 JP JP57063898A patent/JPS58180448A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104841421A (zh) * | 2015-04-15 | 2015-08-19 | 北京旭阳化工技术研究院有限公司 | 一种催化剂组合物、其制备方法及使用其制备邻苯基苯酚的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6254409B2 (enExample) | 1987-11-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU616551B2 (en) | Process for starting-up an ethylene oxide reactor | |
| US3743607A (en) | Palladium-gold catalyst | |
| JP3046865B2 (ja) | 四塩化炭素からのクロロホルムの製造方法及びそれに使用する触媒組成物 | |
| JPH08502064A (ja) | １，２，３−トリクロロプロパンを塩化アリル及びプロピレンに転化する方法 | |
| US5434322A (en) | Process for preparing 1,1-dichloro-2,2,2-trifluoroethane | |
| JP2637812B2 (ja) | フェノールの製造方法 | |
| JPS58180448A (ja) | オルソ−フエニルフエノ−ル類の製造法 | |
| US4088702A (en) | Process for preparing o-phenylphenol | |
| US4060559A (en) | Process for preparing O-phenylphenol | |
| JP2594463B2 (ja) | 脱水素反応用触媒及びその製法 | |
| JP2819171B2 (ja) | 芳香族アルコールの製造方法 | |
| JPH0542298B2 (enExample) | ||
| EP0040414B1 (en) | Process for producing acetaldehyde | |
| JPS63101348A (ja) | １，１−ジエステルの製造方法 | |
| JP2000506886A (ja) | アセトアルデヒドの製造 | |
| US2671803A (en) | Dehalogenation of halogeno acetic acids by hydrogenation | |
| JPS58180447A (ja) | Ｏ−フエニルフエノ−ル類の製造方法 | |
| EP1112775B1 (en) | Catalyst for the preparation of allyl acetate | |
| EP1205246B1 (en) | Process for preparation of catalyst | |
| NO163167B (no) | Fremgangsmaate for fremstilling av planteekstrakt av familien hypoxidaceae for behandling av krefttilstander. | |
| EP0031530B1 (en) | Process for producing pyrogallol | |
| US5206423A (en) | Acyloxylation of alkylaromatic compounds with palladium-tin catalysts | |
| JPS61191627A (ja) | スチレン類含有物の精製法 | |
| JPS6039063B2 (ja) | ヒドロキシ酢酸の製造方法 | |
| JPH0430394B2 (enExample) |