CN102557908B - 2-(环己-1'-烯基)环己酮的制备方法 - Google Patents
2-(环己-1'-烯基)环己酮的制备方法 Download PDFInfo
- Publication number
- CN102557908B CN102557908B CN201110099723.8A CN201110099723A CN102557908B CN 102557908 B CN102557908 B CN 102557908B CN 201110099723 A CN201110099723 A CN 201110099723A CN 102557908 B CN102557908 B CN 102557908B
- Authority
- CN
- China
- Prior art keywords
- cyclohexanone
- cyclohex
- enyl
- catalyst
- reaction
- 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.)
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 106
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 238000006482 condensation reaction Methods 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 238000009833 condensation Methods 0.000 abstract description 9
- 239000011973 solid acid Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000005260 corrosion Methods 0.000 abstract description 3
- 230000007797 corrosion Effects 0.000 abstract description 3
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 17
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 10
- 239000000539 dimer Substances 0.000 description 7
- 238000006356 dehydrogenation reaction Methods 0.000 description 5
- 235000010292 orthophenyl phenol Nutrition 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- 229910018626 Al(OH) Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UOBQDYFTAJKQAL-UHFFFAOYSA-N O=C(CCCC1)C1C1CCCCC1 Chemical compound O=C(CCCC1)C1C1CCCCC1 UOBQDYFTAJKQAL-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 101150026303 HEX1 gene Proteins 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- AFSRWGCXJIBKFK-UHFFFAOYSA-I [V+5].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O Chemical compound [V+5].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AFSRWGCXJIBKFK-UHFFFAOYSA-I 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000011942 biocatalyst Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- ZHXBTDJWYYJMDG-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1.C1=CC=C2C3=CC=CC=C3OC2=C1 ZHXBTDJWYYJMDG-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- 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
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW099146246 | 2010-12-28 | ||
| TW099146246A TW201226379A (en) | 2010-12-28 | 2010-12-28 | Method of producing 2-(cyclohex-1'-enyl) cyclohexanone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102557908A CN102557908A (zh) | 2012-07-11 |
| CN102557908B true CN102557908B (zh) | 2015-09-23 |
Family
ID=45771175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110099723.8A Active CN102557908B (zh) | 2010-12-28 | 2011-04-20 | 2-(环己-1'-烯基)环己酮的制备方法 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US8519192B2 (enExample) |
| CN (1) | CN102557908B (enExample) |
| TW (1) | TW201226379A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104437558B (zh) * | 2014-11-19 | 2017-03-01 | 济南大学 | 一种用于环己酮自缩合反应的新型绿色固体超强酸催化剂及其应用 |
| TWI549749B (zh) * | 2015-05-07 | 2016-09-21 | China Petrochemical Dev Corp Taipei Taiwan | A catalyst composition for preparing o-phenylphenol and a process for preparing o-phenylphenol using the catalyst composition |
| CN106632387B (zh) * | 2016-12-13 | 2018-08-10 | 浙江华贝药业有限责任公司 | 一种工业合成中间体季戊四醇双缩二苯酮的合成工艺 |
| TWI759615B (zh) * | 2019-07-22 | 2022-04-01 | 中國石油化學工業開發股份有限公司 | 2-環己烷基環己醇之製法 |
| TWI755626B (zh) * | 2019-09-03 | 2022-02-21 | 中國石油化學工業開發股份有限公司 | 一種環己酮二聚物之製備方法 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3880930A (en) * | 1972-05-29 | 1975-04-29 | Ruetgerswerke Ag | Process for the production of 1-{8 cyclohexene-(1-YL{9 )-cyclohexanone-(2) by condensation of cyclohexanone |
| US4002693A (en) * | 1974-02-28 | 1977-01-11 | Laporte Industries Limited | Process for the production of o-phenylphenol |
| CN1371897A (zh) * | 2001-02-23 | 2002-10-02 | 南京理工大学 | 用环己酮合成邻苯基苯酚的方法 |
| CN101074187A (zh) * | 2007-05-15 | 2007-11-21 | 盐城市华业医药化工有限公司 | 邻苯基苯酚的制备工艺 |
| CN101205170A (zh) * | 2007-11-08 | 2008-06-25 | 中国石油大学(华东) | 一种固体催化剂用于环己酮自缩合反应的使用方法 |
| CN101538196A (zh) * | 2008-03-18 | 2009-09-23 | 中国石油化工集团公司 | 一种制备2-(1-环己烯基)环己酮的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980716A (en) | 1968-03-15 | 1976-09-14 | Imperial Chemical Industries Limited | Production of ortho-phenylphenol from cyclohexanone |
| NL7500549A (nl) * | 1975-01-17 | 1976-07-20 | Stamicarbon | Werkwijze voor de bereiding van 2-(1-cyclo- hexenyl)-cyclohexanon. |
| CA2068489A1 (en) * | 1991-05-16 | 1992-11-17 | Masaru Ishino | Aldol condensation dehydration catalyst, a process for preparing the same and a process for preparing an aldol condensation dehydrate using the process |
-
2010
- 2010-12-28 TW TW099146246A patent/TW201226379A/zh unknown
-
2011
- 2011-04-20 CN CN201110099723.8A patent/CN102557908B/zh active Active
- 2011-11-16 US US13/297,687 patent/US8519192B2/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3880930A (en) * | 1972-05-29 | 1975-04-29 | Ruetgerswerke Ag | Process for the production of 1-{8 cyclohexene-(1-YL{9 )-cyclohexanone-(2) by condensation of cyclohexanone |
| US4002693A (en) * | 1974-02-28 | 1977-01-11 | Laporte Industries Limited | Process for the production of o-phenylphenol |
| CN1371897A (zh) * | 2001-02-23 | 2002-10-02 | 南京理工大学 | 用环己酮合成邻苯基苯酚的方法 |
| CN101074187A (zh) * | 2007-05-15 | 2007-11-21 | 盐城市华业医药化工有限公司 | 邻苯基苯酚的制备工艺 |
| CN101205170A (zh) * | 2007-11-08 | 2008-06-25 | 中国石油大学(华东) | 一种固体催化剂用于环己酮自缩合反应的使用方法 |
| CN101538196A (zh) * | 2008-03-18 | 2009-09-23 | 中国石油化工集团公司 | 一种制备2-(1-环己烯基)环己酮的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US8519192B2 (en) | 2013-08-27 |
| US20120059193A1 (en) | 2012-03-08 |
| TW201226379A (en) | 2012-07-01 |
| CN102557908A (zh) | 2012-07-11 |
| TWI460156B (enExample) | 2014-11-11 |
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| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |