BG63627B1 - Метод за дехидриране на вторични циклични алкохоли - Google Patents
Метод за дехидриране на вторични циклични алкохоли Download PDFInfo
- Publication number
- BG63627B1 BG63627B1 BG102720A BG10272098A BG63627B1 BG 63627 B1 BG63627 B1 BG 63627B1 BG 102720 A BG102720 A BG 102720A BG 10272098 A BG10272098 A BG 10272098A BG 63627 B1 BG63627 B1 BG 63627B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- catalyst
- dehydration
- zinc
- powder
- calcium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000018044 dehydration Effects 0.000 title claims abstract description 15
- 238000006297 dehydration reaction Methods 0.000 title claims abstract description 15
- -1 cyclic alcohols Chemical group 0.000 title claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 63
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims abstract description 30
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000011787 zinc oxide Substances 0.000 claims abstract description 14
- 229910021532 Calcite Inorganic materials 0.000 claims abstract description 13
- 229910000019 calcium carbonate Inorganic materials 0.000 claims abstract description 12
- 239000007789 gas Substances 0.000 claims abstract description 10
- 230000004048 modification Effects 0.000 claims abstract description 8
- 238000012986 modification Methods 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 239000011148 porous material Substances 0.000 claims description 19
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 18
- 239000000843 powder Substances 0.000 claims description 17
- 239000011701 zinc Substances 0.000 claims description 16
- 229910052725 zinc Inorganic materials 0.000 claims description 15
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 14
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 13
- 229940043430 calcium compound Drugs 0.000 claims description 10
- 150000001674 calcium compounds Chemical class 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002244 precipitate Substances 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 150000003333 secondary alcohols Chemical class 0.000 claims description 5
- 238000002441 X-ray diffraction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 238000011161 development Methods 0.000 claims description 2
- 239000012065 filter cake Substances 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 19
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 229910002804 graphite Inorganic materials 0.000 description 9
- 239000010439 graphite Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 229910002651 NO3 Inorganic materials 0.000 description 5
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001354 calcination Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000003997 cyclic ketones Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- TXXPCSLWXVPZIV-UHFFFAOYSA-L dizinc oxygen(2-) carbonate Chemical compound [O-2].[Zn+2].C([O-])([O-])=O.[Zn+2] TXXPCSLWXVPZIV-UHFFFAOYSA-L 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- MQWLIFWNJWLDCI-UHFFFAOYSA-L zinc;carbonate;hydrate Chemical compound O.[Zn+2].[O-]C([O-])=O MQWLIFWNJWLDCI-UHFFFAOYSA-L 0.000 description 2
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- SFVWPXMPRCIVOK-UHFFFAOYSA-N cyclododecanol Chemical compound OC1CCCCCCCCCCC1 SFVWPXMPRCIVOK-UHFFFAOYSA-N 0.000 description 1
- FHADSMKORVFYOS-UHFFFAOYSA-N cyclooctanol Chemical compound OC1CCCCCCC1 FHADSMKORVFYOS-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- HBYOLNPZXLHVQA-UHFFFAOYSA-J dicalcium dicarbonate Chemical compound [Ca+2].[Ca+2].[O-]C([O-])=O.[O-]C([O-])=O HBYOLNPZXLHVQA-UHFFFAOYSA-J 0.000 description 1
- IHGWHZVHHHLEQR-UHFFFAOYSA-L dimagnesium oxygen(2-) carbonate Chemical compound C([O-])([O-])=O.[Mg+2].[O-2].[Mg+2] IHGWHZVHHHLEQR-UHFFFAOYSA-L 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229960000314 zinc acetate Drugs 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate 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
-
- 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
- C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/06—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of zinc, cadmium or mercury
-
- 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
- B01J27/20—Carbon compounds
- B01J27/232—Carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (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 |
|---|---|---|---|
| DE19609954A DE19609954A1 (de) | 1996-03-14 | 1996-03-14 | Verfahren zur Dehydrierung von sekundären cyclischen Alkoholen |
| PCT/EP1997/001124 WO1997033853A1 (de) | 1996-03-14 | 1997-03-06 | Verfahren zur dehydrierung von sekundären cyclischen alkoholen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG102720A BG102720A (en) | 1999-04-30 |
| BG63627B1 true BG63627B1 (bg) | 2002-07-31 |
Family
ID=7788219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG102720A BG63627B1 (bg) | 1996-03-14 | 1998-08-24 | Метод за дехидриране на вторични циклични алкохоли |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6162758A (cs) |
| EP (1) | EP0888273B1 (cs) |
| JP (1) | JP3901220B2 (cs) |
| KR (1) | KR100500624B1 (cs) |
| CN (1) | CN1106372C (cs) |
| AU (1) | AU2095797A (cs) |
| BG (1) | BG63627B1 (cs) |
| BR (1) | BR9708048B1 (cs) |
| CZ (1) | CZ291458B6 (cs) |
| DE (2) | DE19609954A1 (cs) |
| ES (1) | ES2163737T3 (cs) |
| ID (1) | ID16219A (cs) |
| MY (1) | MY115530A (cs) |
| PL (1) | PL188645B1 (cs) |
| RU (1) | RU2181624C2 (cs) |
| SK (1) | SK282793B6 (cs) |
| TW (1) | TW391889B (cs) |
| UA (1) | UA61070C2 (cs) |
| WO (1) | WO1997033853A1 (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19933079A1 (de) * | 1999-07-19 | 2001-01-25 | Bayer Ag | Dehydrierkatalysatoren |
| DE102004011543A1 (de) * | 2004-03-08 | 2005-10-06 | Basf Ag | Verfahren zur Herstellung optisch aktiver Carbonylverbindungen |
| DE102004057277A1 (de) * | 2004-11-26 | 2006-06-01 | Basf Ag | Verfahren zur Herstellung von Menthol |
| JP2007022922A (ja) * | 2005-07-12 | 2007-02-01 | Tonen Chem Corp | カルボニル化合物の製造法 |
| KR101218453B1 (ko) * | 2008-12-30 | 2013-01-04 | 주식회사 효성 | 탈수소화 촉매 |
| RU2447937C1 (ru) * | 2010-08-27 | 2012-04-20 | Открытое акционерное общество "Ангарский завод катализаторов и органического синтеза" (ОАО "АЗКиОС") | Катализатор для дегидрирования циклогексанола в циклогексанон и способ его приготовления |
| JP6627219B2 (ja) * | 2015-01-05 | 2020-01-08 | 株式会社Ihi | オレフィンの製造方法 |
| RU2593206C1 (ru) * | 2015-07-01 | 2016-08-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Ивановский государственный химико-технологический университет" (ИГХТУ) | Катализатор для дегидрирования циклогексанола в циклогексанон и способ его получения |
| KR101981886B1 (ko) * | 2018-02-01 | 2019-05-23 | 효성화학 주식회사 | 탈수소화 촉매 |
| RU2768141C1 (ru) * | 2021-01-18 | 2022-03-23 | Публичное акционерное общество "КуйбышевАзот" | Способ получения циклогексанона |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3305587A (en) * | 1967-02-21 | Dehydrogenation of cycloalkanols | ||
| NL259810A (cs) * | 1960-07-28 | |||
| DE1443462A1 (de) * | 1962-12-18 | 1969-08-14 | Basf Ag | Verfahren zum Dehydrieren von primaeren oder sekundaeren Alkoholen |
| DE1300905B (de) * | 1964-11-05 | 1969-08-14 | Basf Ag | Verwendung perforierter Hohlkugeln als Verdraengungskoerper in Wirbelschichtreaktoren |
| NL167676C (nl) * | 1969-06-11 | 1982-01-18 | Shell Int Research | Werkwijze voor de bereiding van aldehyden resp. ketonen door katalytische dehydrogenering van primaire resp. secundaire alcoholen, alsmede werkwijze voor het bereiden van een daarbij te gebruiken katalysator. |
| US3981923A (en) * | 1969-06-11 | 1976-09-21 | Shell Oil Company | Dehydrogenation of alcohols to ketones |
| US4670605A (en) * | 1985-05-31 | 1987-06-02 | Industrial Technology Research Institute | Process and catalyst for the conversion of cyclohexanol to cyclohexanone |
-
1996
- 1996-03-14 DE DE19609954A patent/DE19609954A1/de not_active Withdrawn
-
1997
- 1997-03-06 SK SK1169-98A patent/SK282793B6/sk not_active IP Right Cessation
- 1997-03-06 CZ CZ19982928A patent/CZ291458B6/cs not_active IP Right Cessation
- 1997-03-06 US US09/142,218 patent/US6162758A/en not_active Expired - Lifetime
- 1997-03-06 EP EP97906177A patent/EP0888273B1/de not_active Expired - Lifetime
- 1997-03-06 KR KR10-1998-0707225A patent/KR100500624B1/ko not_active Expired - Fee Related
- 1997-03-06 ES ES97906177T patent/ES2163737T3/es not_active Expired - Lifetime
- 1997-03-06 JP JP53225497A patent/JP3901220B2/ja not_active Expired - Fee Related
- 1997-03-06 WO PCT/EP1997/001124 patent/WO1997033853A1/de active IP Right Grant
- 1997-03-06 CN CN97193047A patent/CN1106372C/zh not_active Expired - Lifetime
- 1997-03-06 PL PL97328662A patent/PL188645B1/pl unknown
- 1997-03-06 BR BRPI9708048-9A patent/BR9708048B1/pt not_active IP Right Cessation
- 1997-03-06 DE DE59704534T patent/DE59704534D1/de not_active Expired - Lifetime
- 1997-03-06 RU RU98118915/04A patent/RU2181624C2/ru not_active IP Right Cessation
- 1997-03-06 AU AU20957/97A patent/AU2095797A/en not_active Abandoned
- 1997-03-10 ID IDP970762A patent/ID16219A/id unknown
- 1997-03-10 MY MYPI97001004A patent/MY115530A/en unknown
- 1997-03-14 TW TW086103202A patent/TW391889B/zh not_active IP Right Cessation
- 1997-06-03 UA UA98105387A patent/UA61070C2/uk unknown
-
1998
- 1998-08-24 BG BG102720A patent/BG63627B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG102720A (en) | 1999-04-30 |
| KR19990087753A (ko) | 1999-12-27 |
| CZ291458B6 (cs) | 2003-03-12 |
| WO1997033853A1 (de) | 1997-09-18 |
| CN1106372C (zh) | 2003-04-23 |
| BR9708048B1 (pt) | 2009-01-13 |
| ES2163737T3 (es) | 2002-02-01 |
| MY115530A (en) | 2003-07-31 |
| PL328662A1 (en) | 1999-02-15 |
| SK116998A3 (en) | 1999-02-11 |
| JP3901220B2 (ja) | 2007-04-04 |
| PL188645B1 (pl) | 2005-03-31 |
| JP2000506180A (ja) | 2000-05-23 |
| ID16219A (id) | 1997-09-11 |
| US6162758A (en) | 2000-12-19 |
| EP0888273B1 (de) | 2001-09-05 |
| DE59704534D1 (de) | 2001-10-18 |
| SK282793B6 (sk) | 2002-12-03 |
| UA61070C2 (en) | 2003-11-17 |
| AU2095797A (en) | 1997-10-01 |
| KR100500624B1 (ko) | 2005-10-21 |
| CN1213362A (zh) | 1999-04-07 |
| DE19609954A1 (de) | 1997-09-18 |
| RU2181624C2 (ru) | 2002-04-27 |
| TW391889B (en) | 2000-06-01 |
| BR9708048A (pt) | 1999-07-27 |
| CZ292898A3 (cs) | 1999-05-12 |
| EP0888273A1 (de) | 1999-01-07 |
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