CN115490653A - Synthesis and application of 4-furylmethylene-2,6-di-tert-butyl-2,5-cyclohexadiene-1-one compound - Google Patents
Synthesis and application of 4-furylmethylene-2,6-di-tert-butyl-2,5-cyclohexadiene-1-one compound Download PDFInfo
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- CN115490653A CN115490653A CN202110707476.9A CN202110707476A CN115490653A CN 115490653 A CN115490653 A CN 115490653A CN 202110707476 A CN202110707476 A CN 202110707476A CN 115490653 A CN115490653 A CN 115490653A
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- -1 4-furylmethylene-2,6-di-tert-butyl-2,5-cyclohexadiene-1-one compound Chemical class 0.000 title claims abstract description 14
- 230000015572 biosynthetic process Effects 0.000 title claims description 5
- 238000003786 synthesis reaction Methods 0.000 title claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 47
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 238000005303 weighing Methods 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims 1
- 150000004053 quinones Chemical class 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- JPUUAYFQHNNDBM-UHFFFAOYSA-N bicyclo[4.1.0]hepta-1(6),3-diene-2,5-dione Chemical compound O=C1C=CC(=O)C2=C1C2 JPUUAYFQHNNDBM-UHFFFAOYSA-N 0.000 description 1
- OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N dihydroxy-phenylborane Natural products OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
- C07D307/44—Furfuryl alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F112/02—Monomers containing only one unsaturated aliphatic radical
- C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F112/06—Hydrocarbons
- C08F112/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
- C08F2/40—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation using retarding agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention provides a furan ring modified quinone methyl compound. The invention also discloses a preparation method of the compound. The compound provided by the invention has a good polymerization inhibition effect on styrene. The preparation method of the furan ring modified quinone methyl compound is simple, mature and easy to control.
Description
Technical Field
The invention relates to a furan ring modified quinone methyl compound, in particular to synthesis and application of a furan ring modified quinone methyl compound simultaneously containing furan rings, tert-butyl, cyclohexadiene and methylene quinone.
Background
In the petrochemical industry, the production of styrene is one of the most important engineering techniques. Styrene is an organic raw material widely used and can be used for producing synthetic resins and synthetic rubbers such as polystyrene, styrene butadiene rubber and the like. Therefore, styrene can be widely applied to industries such as coating, pharmacy, dye, textile and the like. However, the double bonds of the styrene monomer are relatively active, so that the polymerization reaction can be thermally excited in a normal-temperature environment without an initiator, and the polymerization is faster at higher temperature. At present, the most common method for industrially producing styrene is an ethylbenzene dehydrogenation method, the temperature in a rectifying tower can reach 70-120 ℃, and the problem of self-polymerization is serious. The generation of the polymer not only causes the loss of reaction monomers and the reduction of production efficiency, but also increases the viscosity of a reaction system, causes the blockage of pipelines and causes safety accidents in severe cases. Therefore, in order to reduce the monomer loss of styrene in the rectification process and prevent and delay the self-polymerization process, the industry often adopts a method of adding a polymerization inhibitor into the rectification process to achieve the styrene polymerization inhibition effect.
Disclosure of Invention
The technical problem to be solved by the present invention is to provide a synthesis and application of phenylboronic acid modified quinone methyl compounds, aiming at the above disadvantages in the prior art. The compound shows good polymerization inhibition effect on styrene.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows: a furan ring modified quinone methide compound, wherein the structural formula (I) of the compound is as follows:
the aboveThe furan ring modified quinone methyl compound is characterized in that R is
And
in addition, the invention also provides a method for preparing the furan ring modified quinone methyl compound, which is characterized in that the synthetic route of the compound is as follows:
the method comprises the following steps:
weighing the compounds of the formulas 1 and 2 and organic base according to a certain proportion, adding a solvent for dissolving, reacting for 8-10 hours in a nitrogen atmosphere, cooling to 100 ℃ after the reaction is finished, dropwise adding phosphoric acid, standing for liquid separation, washing with saturated salt water to be neutral, absorbing excessive moisture by anhydrous magnesium sulfate, and separating and purifying to obtain the corresponding compounds of the formulas 3a, 3b or 3 c.
Furthermore, the invention also provides application of the furan ring modified quinone methyl compound in styrene polymerization inhibition.
The technical solution of the present invention is further described in detail with reference to the accompanying drawings and embodiments.
Drawings
The attached drawing is a schematic diagram of the experimental result of polymerization inhibition of the styrene by the furan ring modified quinone methyl compound.
Detailed Description
It will be understood that terms such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
< implementation 1 >
Weighing the compound of formula 1 (2.4 mmol), the compound of formula 2a (2.8 mmol) and piperazine (4.8 mmol) according to the proportion, adding 20mL of dichloromethane solvent to dissolve, heating to 130 ℃, and reacting for 8h, wherein foam is continuously generated in the process. After the reaction, the temperature was reduced to 100 ℃ and phosphoric acid (2.4 mm0 l) was slowly added dropwise to the reaction mixture, and after 1 hour of the reaction, the mixture was allowed to stand for liquid separation, washed with saturated salt water to neutrality, allowed to stand for liquid separation, and excess water was absorbed by anhydrous magnesium sulfate, and magnesium sulfate was removed by filtration. The solvent was then distilled off under reduced pressure, and the extract was isolated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5: 1) to give a deep red viscous liquid 3a with a yield of 71.3%.
Infrared IR (KBr, cm) -1 )：3649.13，2961.38，2857.70，1406.98，1260.8，1022.45，800.56，701.39。
< implementation 2 >
Weighing the compound of formula 1 (2.4 mmol), the compound of formula 2b (2.8 mmol) and piperazine (4.8 mmol) according to the proportion, adding 20mL of dichloromethane solvent to dissolve, heating to 130 ℃, and reacting for 8h, wherein foam is continuously generated in the process. After the reaction, the temperature was reduced to 100 ℃ and phosphoric acid (2.4 mmol) was slowly dropped to react for 1 hour, followed by standing and liquid separation, washing with saturated saline to neutrality, standing and liquid separation, allowing anhydrous magnesium sulfate to absorb excess water, and filtering to remove magnesium sulfate. The solvent was then distilled off under reduced pressure, and the red viscous liquid 3b was isolated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5: 1) with a yield of 79.7%.
Infrared IR (KBr, cm-1): 3642.21, 2924.76, 2864.97, 1756.64, 1427.93, 1257.84, 1143.15, 1022.10, 801.60, 745.91.
< implementation 3 >
Weighing the compound of formula 1 (2.4 mmol), the compound of formula 2c (2.8 mmol) and piperazine (4.8 mmol) according to a ratio, adding 20mL of dichloromethane solvent to dissolve, heating to 130 ℃, and reacting for 8h, wherein foam is continuously generated in the process. After the reaction, the temperature was reduced to 100 ℃ and phosphoric acid (2.42 mmol) was slowly dropped to react for 1 hour, followed by standing and liquid separation, washing with saturated saline to neutrality, standing and liquid separation, allowing anhydrous magnesium sulfate to absorb excess water, and filtering to remove magnesium sulfate. The solvent was then distilled off under reduced pressure and the product was isolated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5: 1) to give a deep red viscous liquid 3c with a yield of 69.6%.
Infrared IR (KBr, cm-1): 3644.78, 2924.67, 1710.90, 1427.10, 1230.51, 1172.06, 1142.93, 897.37, 745.63.
< example 4 >
The polymerization inhibiting properties for styrene comprising compounds 3a, 3b and 3c of example 1, example 2 and example 3:
100mL of styrene was weighed into a round-bottom flask, heated in a 100 ℃ constant temperature oil bath, and heated until styrene polymerized. The time to start the polymerization of styrene was recorded.
0.5mL of the styrene polymerization inhibitor 3a, 3b or 3c was added dropwise to a round-bottomed flask containing 100mL of styrene, and the flask was heated in a constant-temperature oil bath at 100 ℃ until styrene was polymerized. The time to start the polymerization of styrene was recorded.
As shown in the figure, before adding no polymerization inhibitor, the polymerization of styrene is started from 90 minutes, and after adding the compound 3a, 3b or 3c, the polymerization start time of styrene is delayed obviously, wherein the compound 3c has the best effect of inhibiting polymerization of styrene, and the polymerization of styrene is started after 120 minutes.
While embodiments of the invention have been disclosed above, it is not intended to be limited to the uses set forth in the specification and examples. It can be applied to all kinds of fields suitable for the present invention. Additional modifications will readily occur to those skilled in the art. It is therefore intended that the invention not be limited to the exact details and illustrations described and illustrated herein, but fall within the scope of the appended claims and equivalents thereof.
Claims (3)
1. A furan ring modified quinone methyl compound is characterized in that the structural formula (I) of the compound is as follows:
in the formula (I), R is
2. A method for the synthesis of a furan ring modified quinone methide compound as claimed in claim 1 or 2, wherein said compound is synthesized by the following scheme:
the method comprises the following steps:
weighing the compounds of the formulas 1 and 2 and organic base according to a certain proportion, adding a solvent for dissolving, reacting for 8-10 hours in a nitrogen atmosphere, cooling to 100 ℃ after the reaction is finished, dropwise adding phosphoric acid, standing for liquid separation, washing with saturated salt water to be neutral, absorbing excessive moisture by anhydrous magnesium sulfate, and separating and purifying to obtain the corresponding compounds of the formulas 3a, 3b or 3 c.
3. The use of the furan ring-modified quinone methide of claim 1 for the preparation of styrene polymerization inhibitors.
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|---|---|---|---|
| CN202110707476.9A CN115490653A (en) | 2021-06-18 | 2021-06-18 | Synthesis and application of 4-furylmethylene-2,6-di-tert-butyl-2,5-cyclohexadiene-1-one compound |
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| CN202110707476.9A CN115490653A (en) | 2021-06-18 | 2021-06-18 | Synthesis and application of 4-furylmethylene-2,6-di-tert-butyl-2,5-cyclohexadiene-1-one compound |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0744392A1 (en) * | 1995-05-26 | 1996-11-27 | Ciba-Geigy Ag | A new one-pot process for the preparation of 7-aryl-2,6-disubstituted quinone methides |
| US5583247A (en) * | 1995-04-14 | 1996-12-10 | Ciba-Geigy Corporation | 7-substituted quinone methides as inhibitors for unsaturated monomers |
| CN1139094A (en) * | 1995-04-14 | 1997-01-01 | 希巴-盖吉股份公司 | Inhibition of unsaturated monomers with 7-aryl quinone methides |
| CN104341281A (en) * | 2014-06-29 | 2015-02-11 | 浙江大学 | 2, 6-di-tert-butyl-4-(2-methoxyphenylmethylene)-2, 5-cyclohexadiene-1-one and preparation method thereof |
| CN106866443A (en) * | 2015-12-10 | 2017-06-20 | 华东理工大学 | Chiral beta-diaryl-alpha-amino acid derivatives and application thereof |
-
2021
- 2021-06-18 CN CN202110707476.9A patent/CN115490653A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5583247A (en) * | 1995-04-14 | 1996-12-10 | Ciba-Geigy Corporation | 7-substituted quinone methides as inhibitors for unsaturated monomers |
| CN1139094A (en) * | 1995-04-14 | 1997-01-01 | 希巴-盖吉股份公司 | Inhibition of unsaturated monomers with 7-aryl quinone methides |
| EP0744392A1 (en) * | 1995-05-26 | 1996-11-27 | Ciba-Geigy Ag | A new one-pot process for the preparation of 7-aryl-2,6-disubstituted quinone methides |
| CN104341281A (en) * | 2014-06-29 | 2015-02-11 | 浙江大学 | 2, 6-di-tert-butyl-4-(2-methoxyphenylmethylene)-2, 5-cyclohexadiene-1-one and preparation method thereof |
| CN106866443A (en) * | 2015-12-10 | 2017-06-20 | 华东理工大学 | Chiral beta-diaryl-alpha-amino acid derivatives and application thereof |
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