CN114315541A - Cyclohexanone composition and application thereof - Google Patents
Cyclohexanone composition and application thereof Download PDFInfo
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- CN114315541A CN114315541A CN202210048165.0A CN202210048165A CN114315541A CN 114315541 A CN114315541 A CN 114315541A CN 202210048165 A CN202210048165 A CN 202210048165A CN 114315541 A CN114315541 A CN 114315541A
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- CN
- China
- Prior art keywords
- trimethyl
- cyclohexene
- composition
- dione
- cyclohexanone
- Prior art date
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- 239000002994 raw material Substances 0.000 claims abstract description 18
- AYJXHIDNNLJQDT-UHFFFAOYSA-N 2,6,6-Trimethyl-2-cyclohexene-1,4-dione Chemical compound CC1=CC(=O)CC(C)(C)C1=O AYJXHIDNNLJQDT-UHFFFAOYSA-N 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 38
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 16
- POSWICCRDBKBMH-UHFFFAOYSA-N 3,3,5-trimethylcyclohexan-1-one Chemical compound CC1CC(=O)CC(C)(C)C1 POSWICCRDBKBMH-UHFFFAOYSA-N 0.000 claims description 14
- IITQJMYAYSNIMI-UHFFFAOYSA-N 3-Methyl-2-cyclohexen-1-one Chemical compound CC1=CC(=O)CCC1 IITQJMYAYSNIMI-UHFFFAOYSA-N 0.000 claims description 12
- LKOKKQDYMZUSCG-UHFFFAOYSA-N 3,5,5-Trimethyl-3-cyclohexen-1-one Chemical compound CC1=CC(C)(C)CC(=O)C1 LKOKKQDYMZUSCG-UHFFFAOYSA-N 0.000 claims description 10
- 239000012752 auxiliary agent Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- OQJMHUOCLRCSED-UHFFFAOYSA-N 3,3,5,5-tetramethylcyclohexan-1-one Chemical compound CC1(C)CC(=O)CC(C)(C)C1 OQJMHUOCLRCSED-UHFFFAOYSA-N 0.000 claims description 6
- ROTNQFPVXVZSRL-UHFFFAOYSA-N 4,4,6-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one Chemical compound C1C(C)(C)CC(=O)C2OC21C ROTNQFPVXVZSRL-UHFFFAOYSA-N 0.000 claims description 6
- PIGJMFZYQUTSNI-UHFFFAOYSA-N 5,5-dimethyl-3-oxocyclohexene-1-carbaldehyde Chemical compound CC1(C)CC(=O)C=C(C=O)C1 PIGJMFZYQUTSNI-UHFFFAOYSA-N 0.000 claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- -1 nitrogen-containing compound Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 2
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 229910009474 Y2O3—ZrO2 Inorganic materials 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 241000758789 Juglans Species 0.000 description 3
- 235000009496 Juglans regia Nutrition 0.000 description 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 235000020234 walnut Nutrition 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005485 electric heating Methods 0.000 description 2
- 238000009775 high-speed stirring Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 description 1
- SHWZFQPXYGHRKT-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;nickel Chemical compound [Ni].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O SHWZFQPXYGHRKT-FDGPNNRMSA-N 0.000 description 1
- FFIDVTCKFVYQCZ-UHFFFAOYSA-N 1,3,3-trimethylcyclohexene Chemical compound CC1=CC(C)(C)CCC1 FFIDVTCKFVYQCZ-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- JEBFVOLFMLUKLF-IFPLVEIFSA-N Astaxanthin Natural products CC(=C/C=C/C(=C/C=C/C1=C(C)C(=O)C(O)CC1(C)C)/C)C=CC=C(/C)C=CC=C(/C)C=CC2=C(C)C(=O)C(O)CC2(C)C JEBFVOLFMLUKLF-IFPLVEIFSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 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
- 239000000020 Nitrocellulose Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000013793 astaxanthin Nutrition 0.000 description 1
- MQZIGYBFDRPAKN-ZWAPEEGVSA-N astaxanthin Chemical compound C([C@H](O)C(=O)C=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)[C@@H](O)CC1(C)C MQZIGYBFDRPAKN-ZWAPEEGVSA-N 0.000 description 1
- 229940022405 astaxanthin Drugs 0.000 description 1
- 239000001168 astaxanthin Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- UBEWDCMIDFGDOO-UHFFFAOYSA-N cobalt(II,III) oxide Inorganic materials [O-2].[O-2].[O-2].[O-2].[Co+2].[Co+3].[Co+3] UBEWDCMIDFGDOO-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- ZKXWKVVCCTZOLD-UHFFFAOYSA-N copper;4-hydroxypent-3-en-2-one Chemical compound [Cu].CC(O)=CC(C)=O.CC(O)=CC(C)=O ZKXWKVVCCTZOLD-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000010010 raising Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- Y02P20/10—Process efficiency
Abstract
The invention provides a cyclohexanone composition and application thereof. The cyclohexanone composition is a composition containing 3,5, 5-trimethyl-3-cyclohexene-1-ketone and has a special composition, and the composition is prepared by taking 3,5, 5-trimethyl-2-cyclohexene-1-ketone as a raw material and reacting. The composition can be used for preparing 2,6, 6-trimethyl-2-cyclohexene-1, 4-diketone. The method has the advantages of less catalyst consumption, low energy consumption, high product yield and easy industrialization.
Description
Technical Field
The invention belongs to the field of cyclohexanone synthesis, and particularly relates to a cyclohexanone composition and application thereof.
Background
Cyclohexanone-based materials have been used in a wide variety of applications, such as 3,5, 5-trimethyl-2-cyclohexen-1-one as a solvent for paints, inks, coatings, gums, resins, nitrocellulose, and as an intermediate for chemical synthesis, particularly for vinyl resins. Is a high boiling point solvent for nitro spray paint and synthetic resin paint. As a special paint diluent, a soluble phenolic resin and an epoxy resin are used in admixture with methyl isobutyl ketone.
3,3, 5-trimethylcyclohexanone is used as an important high-boiling organic solvent and a medicine synthesis intermediate, is mainly used in the fields of medicines, pesticides, fine chemical engineering and the like, and downstream products of the intermediate can be used as vulcanizing agents in rubber and other industries and polymer monomers in plastic industry.
3,5, 5-trimethyl-3-cyclohexene-1-ketone is an important intermediate for synthesizing natural products such as vitamin E, carotenoid, astaxanthin and the like and spices, in particular to a main raw material for preparing tea-scented ketone, and the tea-scented ketone is also a precursor for preparing trimethyl hydrogen hydroquinone (VE main ring).
3,5, 5-trimethyl-3-cyclohexene-1-ketone is an important raw material for preparing 2,6, 6-trimethyl-2-cyclohexene-1, 4-diketone. However, the existing method for processing 3,5, 5-trimethyl-3-cyclohexene-1-ketone is not beneficial to obtaining 2,6, 6-trimethyl-2-cyclohexene-1, 4-diketone products with high yield and high selectivity. US patent US4010205A uses triethanolamine as catalyst to perform reactive distillation, and washes the reaction solution with tartaric acid and brine to obtain 3,5, 5-trimethyl-3-cyclohexene-1-one; the technical scheme has the defects that the purity of the obtained 3,5, 5-trimethyl-3-cyclohexene-1-ketone is low and the post-treatment process is complex; US5907065A, US6005147A utilize Co3O4、CaO、Fe3O4The oxide is used as a catalyst, a reduced pressure rectification method is adopted for reaction, the purity of the obtained 3,5, 5-trimethyl-3-cyclohexene-1-ketone can reach more than 97 percent, but the reaction byproducts are more, and the space-time yield is low. 3,5, 5-trimethyl-3-cyclohexene treated by the above two patentsWhen the (E) -1-ketone is used for preparing the 2,6, 6-trimethyl-2-cyclohexene-1, 4-diketone, the ideal target product is difficult to obtain.
U.S. Pat. No. 4, 4005145A discloses a method for preparing a crude product of beta-isophorone by reaction and rectification with adipic acid as a catalyst, and the purity of the obtained product can reach more than 91%. The process also suffers from the problems of more by-products, low space-time yield, severe corrosion of equipment, etc.
In summary, it is desirable to obtain a cyclohexanone composition that produces 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione in high yield and with high selectivity.
Disclosure of Invention
The invention aims to provide a cyclohexanone composition, which can obtain higher yield and selectivity when being used for preparing 2,6, 6-trimethyl-2-cyclohexene-1, 4-diketone.
In order to achieve the purpose, the invention adopts the following technical scheme:
a cyclohexanone composition, said composition comprising the following components:
i.90-99.9 wt% of 3,5, 5-trimethyl-3-cyclohexene-1-one; and
0.01-5 wt% of 3, 3-dimethyl-5-methylenecyclohex-1-one; and
iii 0.0001-0.005 wt% of 3-methyl-cyclohex-2-enone; and
0.001 to 1 wt% of 3,3, 5-trimethylcyclohexanone; and
0.001-2 wt% of 3,3,5, 5-tetramethylcyclohexanone; and
vi.0.01-8 wt.% of 3,5, 5-trimethyl-2-cyclohexen-1-one; and
0.001-5 wt% of 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione; and
viii.0.0001-0.01 wt% of 5, 5-dimethyl-3-oxocyclohex-1-enecarbaldehyde; and
ix.0.0001-0.005% by weight of 2,2, 6-trimethylcyclohexyl-1, 4-dione; and
x.0.0001-0.01 wt% of 2, 3-epoxy-3, 5, 5-trimethyl-1-cyclohexanone;
preferably, the composition comprises the following components:
i.97-99.7 wt% of 3,5, 5-trimethyl-3-cyclohexene-1-one; and
0.1-2 wt% of 3, 3-dimethyl-5-methylenecyclohex-1-one; and
iii 0.001-0.002 wt% of 3-methyl-cyclohex-2-enone; and
0.01-0.1 wt% of 3,3, 5-trimethylcyclohexanone; and
v.0.1-0.5 wt% of 3,3,5, 5-tetramethylcyclohexanone; and
vi.0.01-2.7 wt% of 3,5, 5-trimethyl-2-cyclohexen-1-one; and
0.01-0.1 wt% of 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione; and
viii.0.001-0.004 wt% of 5, 5-dimethyl-3-oxocyclohex-1-enecarbaldehyde; and
ix.0.001-0.005% by weight of 2,2, 6-trimethylcyclohex-1, 4-dione; and
x.0.001-0.006 wt.% of 2, 3-epoxy-3, 5, 5-trimethyl-1-cyclohexanone.
In the invention, the composition is prepared by taking 3,5, 5-trimethyl-2-cyclohexene-1-ketone as a raw material and reacting.
It is another object of the present invention to provide a process for preparing a cyclohexanone composition.
A process for preparing a cyclohexanone composition as described above, said process comprising: adding the catalyst, the auxiliary agent and the raw material 3,5, 5-trimethyl-2-cyclohexene-1-ketone composition into a reaction rectifying tower from a tower bottom, and heating the tower bottom for reaction. In the reaction, the raw material 3,5, 5-trimethyl-2-cyclohexene-1-ketone mainly undergoes isomerization reaction.
In the invention, the reaction is carried out under the conditions of a catalyst and an auxiliary agent. Preferably, the catalyst is a metal acetylacetonate and/or an inorganic base catalyst; the acetylacetone metal can be cobalt acetylacetonate, iron acetylacetonate, copper acetylacetonate, nickel acetylacetonate, titanium acetylacetonate, etc. The inorganic base may be Na2CO3、K2CO3LiOH, NaOH, KOH, etc. Preferably, the auxiliary agent is a nitrogen-containing compound, preferably one or more of phenazine, 2, 3-diaminophenol oxazine, 3-indole formaldehyde and 3-hydroxypyridine.
In the present invention, the catalyst is used in an amount of 0.1ppm to 10ppm, preferably 0.5ppm to 8ppm, based on the mass of the starting material 3,5, 5-trimethyl-2-cyclohexen-1-one.
In the present invention, the amount of the auxiliary is 0.1ppm to 100ppm, preferably 0.2ppm to 50ppm, based on the mass of the starting material 3,5, 5-trimethyl-2-cyclohexen-1-one.
In the invention, the theoretical plate number of the reaction rectifying tower is 10-70, preferably 20-50; the reflux ratio is 200:1-2: 1.
In the present invention, the reaction is fed at normal temperature.
In the present invention, the reaction is warmed to 120 ℃ to 300 ℃, preferably 150 ℃ to 270 ℃, at a pressure of 0.05barA to 5barA, preferably 0.2barA to 3.2 barA.
It is still another object of the present invention to provide a method for preparing 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione.
The method for preparing the 2,6, 6-trimethyl-2-cyclohexene-1, 4-diketone adopts the cyclohexanone composition as a raw material, or adopts the cyclohexanone composition prepared by the composition preparation method as a raw material.
In the present invention, the cyclohexanone composition used in the method for preparing 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione comprises the following components:
i.90-99.9 wt% of 3,5, 5-trimethyl-3-cyclohexene-1-one; and
0.01-5 wt% of 3, 3-dimethyl-5-methylenecyclohex-1-one; and
iii 0.0001-0.005 wt% of 3-methyl-cyclohex-2-enone; and
0.001 to 1 wt% of 3,3, 5-trimethylcyclohexanone; and
0.001-2 wt% of 3,3,5, 5-tetramethylcyclohexanone; and
vi.0.01-8 wt.% of 3,5, 5-trimethyl-2-cyclohexen-1-one; and
0.001-5 wt% of 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione; and
viii.0.0001-0.01 wt% of 5, 5-dimethyl-3-oxocyclohex-1-enecarbaldehyde; and
ix.0.0001-0.005% by weight of 2,2, 6-trimethylcyclohexyl-1, 4-dione; and
x.0.0001-0.01 wt% of 2, 3-epoxy-3, 5, 5-trimethyl-1-cyclohexanone.
In one embodiment, the process for preparing 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione comprises: taking a reaction kettle provided with a six-blade turbine high-speed stirring paddle as a reactor, sequentially adding the cyclohexanone composition, acetonitrile, a catalyst and hydroquinone into the reaction kettle, starting electric heating and mechanical stirring, raising the temperature of the reaction liquid, dropwise adding a hydrogen peroxide solution, and continuing the heat preservation reaction. After the reaction, the reaction mixture was analyzed by gas chromatography.
The composition prepared by the method has higher reaction activity when preparing the target product 2,6, 6-trimethyl-2-cyclohexene-1, 4-diketone, and can obtain the target product 2,6, 6-trimethyl-2-cyclohexene-1, 4-diketone under the conditions of less catalyst dosage and milder reaction.
The introduction of the auxiliary agent can reduce the reaction of the raw material and the product to generate heavy components at high temperature, thereby reducing the occurrence of side reactions and the loss of the raw material and the product, and meanwhile, the auxiliary agent is used as a nitrogen-containing compound with high boiling point, basically has no loss in the reaction process, can be repeatedly used after being recovered, and reduces the cost of the raw material to the maximum extent. The introduction of the auxiliary agent enables the catalyst to achieve better reaction effect under the condition of less using amount.
Compared with the prior art, the scheme of the invention has the following positive effects:
1) the catalyst consumption is greatly reduced, the equipment corrosion is reduced, and the industrial amplification and material selection are facilitated.
2) The obtained cyclohexanone composition has better downstream application, and particularly has better conversion rate and selectivity when being used for preparing 2,6, 6-trimethyl-2-cyclohexene-1, 4-diketone.
3) In the prior art, compared with other processes, the productivity is obviously increased, the energy consumption is reduced, and the volume of the reaction rectifying tower is reduced.
4) Compared with other processes, the method has the advantages of better reaction selectivity and obviously reduced by-products.
Detailed Description
The method according to the invention will be further illustrated by the following examples, but the invention is not limited to the examples listed, but also encompasses any other known modification within the scope of the claims of the invention.
The main raw material sources are shown in the following table:
the gas chromatograph is Agilent 7820A, and the gas chromatographic analysis conditions are as follows: an Agilent gas chromatography polysiloxane column HP-5 is subjected to online measurement, the temperature of a gasification chamber is 250 ℃, the temperature of a detector is 250 ℃, and the column temperature is programmed temperature: 50 ℃ for 1 min; at 80 ℃ for 1 min; 10 ℃/min to 250 ℃, 10min, and the sample injection amount of 0.2 mu L.
Example 1
Under normal temperature condition, adding 20kg of mixed solution of raw materials of 3,5, 5-trimethyl-2-cyclohexen-1-one, 40.0mg of cobalt acetylacetonate and 900.0mg of phenazine into a tower kettle of a stainless steel rectifying tower with 45 theoretical plates, maintaining the tower top pressure of the reactive rectifying tower at 2.4barA, slowly heating the tower kettle to boil, keeping the temperature of the tower kettle at 259 ℃, slowly increasing the reflux quantity of the tower top to 80kg/h after the reflux of the tower top is established, after the total reflux is about 1h, starting to extract materials at the speed of 5.0kg/h from the tower top, simultaneously feeding fresh raw materials of 3,5, 5-trimethyl-2-cyclohexen-1-one into the tower kettle at the feeding speed of 5.0kg/h, keeping the reaction liquid volume of the tower kettle constant in the whole rectifying process, keeping the temperature of the tower kettle at 259 plus 261 ℃ after the stable operation is carried out for 720h, the gas phase analysis is carried out on the materials extracted from the tower top, and the mass composition is as follows:
the cyclohexanone composition obtained in the above way is used to prepare 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione.
Preparing 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione by using the obtained cyclohexanone composition as a raw material: drying walnut shell at 120 deg.C to constant weight, pulverizing and mixingSieving with 160 mesh sieve. The activator adopts H with the mass fraction of 40%3PO4Adding 300g of activating agent into 50g of walnut shell powder, mixing and standing for 20h, drying the mixture at 120 ℃, and then putting the mixture into a tube furnace for pyrolysis at 550 ℃ for 1h (under the protection of nitrogen). After cooling to room temperature, the activated carbon is taken out and washed to be neutral. Drying the activated carbon, cooling, crushing, sieving by a 200-mesh sieve, putting into a dryer, and storing for later use, wherein the prepared walnut shell activated carbon is recorded as W-AC.
Weighing 4g of nano-Y2O34g of nano ZrO2And 50g of carrier W-AC are ground in an agate mortar for 30min, transferred into a beaker, added with 300g of pure water and stirred for 1h, so that the active component and the carrier are fully mixed. And (3) carrying out ultrasonic oscillation on the stirred mixed sample for 2 hours at the frequency of 100Hz and the temperature of 25 ℃ so as to further and fully mix the sample. And (5) putting the sample into a constant temperature box for drying. Taking out and grinding to obtain Y2O3-ZrO2/W-AC。
MmXn-Y2O3-ZrO2Preparation of/W-AC: all of the obtained Y2O3-ZrO2the/W-AC is dispersed in 100g of water and dissolved in 1.2g of magnesium chloride aqueous solution, and ultrasonic treatment is carried out for 1 h. Followed by vigorous stirring at 60 ℃ for 10 h. Stopping stirring, standing, discarding supernatant, centrifuging, and drying precipitate to obtain MgCl2-Y2O3-ZrO2The catalyst was a/W-AC catalyst (denoted as catalyst a). According to XPS test of the content of Y, Zr and Mg elements, the catalyst a is prepared from the following components: y is2O3:ZrO2:MgCl2100.0:8.0:8.0:2.1 (mass ratio).
A reaction kettle provided with a six-blade turbine high-speed stirring paddle is used as a reactor. 1382g of the prepared cyclohexanone composition, 1658g of acetonitrile, 6.90g of a catalyst a and 41.46g of hydroquinone are sequentially added into a reaction kettle; starting electric heating and mechanical stirring, heating the temperature of the reaction solution to 30 ℃, dropwise adding 2429g of 35% hydrogen peroxide solution for 5 hours, and continuing to perform heat preservation reaction for 2 hours. After the reaction, gas chromatography analysis showed that the conversion of the starting material, 3,5, 5-trimethyl-2-cyclohexen-1-one, was 99.81%, the selectivity for 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione was 96.24%, and the yield of 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione was 96.0%.
Compared with the prior art, the preparation process of the 2,6, 6-trimethyl-2-cyclohexene-1, 4-diketone has the advantages that the dosage of the catalyst a is reduced by 80%, the reaction time is reduced by 30%, and the reaction yield is improved by about 1.5%.
Examples 2 to 7
Operating conditions were varied, the procedure was as in example 1, and other conditions and results are as in the following table:
comparative example 1
Under the condition of normal temperature, 20kg of raw material 3,5, 5-trimethyl-2-cyclohexene-1-ketone and 4.0g of KOH mixed solution are added into a tower bottom of a stainless steel rectifying tower with 45 theoretical plates, the top pressure of the reactive rectifying tower is maintained at 2.4barA, then the tower bottom is slowly heated to boil, the temperature of the tower bottom is 258 ℃, after the reflux is established at the tower top, the reflux quantity at the tower top is slowly increased to 80kg/h, after the total reflux is about 1h, the material is extracted from the tower top at the speed of 5kg/h, meanwhile, fresh raw material 3,5, 5-trimethyl-2-cyclohexene-1-ketone is fed into the tower bottom at the feeding speed of 5.0kg/h, the reaction liquid product at the tower bottom is maintained to be constant in the whole rectifying process, after the stable operation is carried out for 72h, the temperature of the tower bottom is maintained at 258-, the gas phase analysis is carried out on the materials extracted from the tower top, and the compositions are as follows:
the 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione was prepared using the 3,5, 5-trimethyl-3-cyclohexene-1-one obtained above as a starting material in exactly the same manner as in example 1, and after completion of the reaction, gas chromatography analysis showed that the conversion of the starting material 3,5, 5-trimethyl-2-cyclohexene-1-one was 82.12%, the selectivity for 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione was 73.29%, and the yield of 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione was 60.1%.
It will be appreciated by those skilled in the art that modifications or adaptations to the invention may be made in light of the teachings of the present specification. Such modifications or adaptations are intended to be within the scope of the present invention as defined in the claims.
Claims (9)
1. A cyclohexanone composition characterized in that said composition comprises the following components:
i.90-99.9 wt% of 3,5, 5-trimethyl-3-cyclohexene-1-one; and
0.01-5 wt% of 3, 3-dimethyl-5-methylenecyclohex-1-one; and
iii 0.0001-0.005 wt% of 3-methyl-cyclohex-2-enone; and
0.001 to 1 wt% of 3,3, 5-trimethylcyclohexanone; and
0.001-2 wt% of 3,3,5, 5-tetramethylcyclohexanone; and
vi.0.01-8 wt.% of 3,5, 5-trimethyl-2-cyclohexen-1-one; and
0.001-5 wt% of 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione; and
viii.0.0001-0.01 wt% of 5, 5-dimethyl-3-oxocyclohex-1-enecarbaldehyde; and
ix.0.0001-0.005% by weight of 2,2, 6-trimethylcyclohexyl-1, 4-dione; and
x.0.0001-0.01 wt% of 2, 3-epoxy-3, 5, 5-trimethyl-1-cyclohexanone;
preferably, the composition comprises the following components:
i.97-99.7 wt% of 3,5, 5-trimethyl-3-cyclohexene-1-one; and
0.1-2 wt% of 3, 3-dimethyl-5-methylenecyclohex-1-one; and
iii 0.001-0.002 wt% of 3-methyl-cyclohex-2-enone; and
0.01-0.1 wt% of 3,3, 5-trimethylcyclohexanone; and
v.0.1-0.5 wt% of 3,3,5, 5-tetramethylcyclohexanone; and
vi.0.01-2.7 wt% of 3,5, 5-trimethyl-2-cyclohexen-1-one; and
0.01-0.1 wt% of 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione; and
viii.0.001-0.004 wt% of 5, 5-dimethyl-3-oxocyclohex-1-enecarbaldehyde; and
ix.0.001-0.005% by weight of 2,2, 6-trimethylcyclohex-1, 4-dione; and
x.0.001-0.006 wt.% of 2, 3-epoxy-3, 5, 5-trimethyl-1-cyclohexanone.
2. The composition of claim 1, wherein the composition is prepared by reacting 3,5, 5-trimethyl-2-cyclohexen-1-one as a starting material.
3. A process for preparing a cyclohexanone composition according to claim 1 or 2, which process is: adding the catalyst, the auxiliary agent and the raw material 3,5, 5-trimethyl-2-cyclohexene-1-ketone composition into a reaction rectifying tower from a tower bottom, and heating the tower bottom for reaction.
4. The process according to claim 3, wherein the reaction is carried out under catalyst and promoter conditions;
preferably, the catalyst is a metal acetylacetonate and/or an inorganic base catalyst;
preferably, the auxiliary agent is a nitrogen-containing compound, preferably one or more of phenazine, 2, 3-diaminophenol oxazine, 3-indole formaldehyde and 3-hydroxypyridine.
5. The process according to claim 4, characterized in that the catalyst is used in an amount of 0.1ppm to 10ppm, preferably 0.5ppm to 8ppm, based on the mass of the starting material 3,5, 5-trimethyl-2-cyclohexen-1-one.
6. The process according to claim 4, characterized in that the auxiliaries are used in an amount of from 0.1ppm to 100ppm, preferably from 0.2ppm to 50ppm, based on the mass of the starting material 3,5, 5-trimethyl-2-cyclohexen-1-one.
7. A method according to claim 3, characterized in that the reaction rectification column has a theoretical plate number of 10-70, preferably 20-50; the reflux ratio is 200:1-2: 1;
and/or, the reaction is fed at normal temperature;
and/or, the reaction is warmed to 120 ℃ to 300 ℃, preferably 150 ℃ to 270 ℃, pressure 0.05barA to 5barA, preferably 0.2barA to 3.2 barA.
8. A process for the preparation of 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione starting from a cyclohexanone composition as claimed in claim 1 or 2 or prepared by a process for the preparation of a composition as claimed in any one of claims 3 to 7.
9. The process for preparing 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione as claimed in claim 8, wherein the cyclohexanone composition comprises the following components:
i.90-99.9 wt% of 3,5, 5-trimethyl-3-cyclohexene-1-one; and
0.01-5 wt% of 3, 3-dimethyl-5-methylenecyclohex-1-one; and
iii 0.0001-0.005 wt% of 3-methyl-cyclohex-2-enone; and
0.001 to 1 wt% of 3,3, 5-trimethylcyclohexanone; and
0.001-2 wt% of 3,3,5, 5-tetramethylcyclohexanone; and
vi.0.01-8 wt.% of 3,5, 5-trimethyl-2-cyclohexen-1-one; and
0.001-5 wt% of 2,6, 6-trimethyl-2-cyclohexene-1, 4-dione; and
viii.0.0001-0.01 wt% of 5, 5-dimethyl-3-oxocyclohex-1-enecarbaldehyde; and
ix.0.0001-0.005% by weight of 2,2, 6-trimethylcyclohexyl-1, 4-dione; and
x.0.0001-0.01 wt% of 2, 3-epoxy-3, 5, 5-trimethyl-1-cyclohexanone.
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