CN102584559A - Method for separating and purifying 2,3,5-trimethyl benzoquinone - Google Patents
Method for separating and purifying 2,3,5-trimethyl benzoquinone Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 68
- QIXDHVDGPXBRRD-UHFFFAOYSA-N 2,3,5-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C(C)=C(C)C1=O QIXDHVDGPXBRRD-UHFFFAOYSA-N 0.000 title claims abstract description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 81
- 239000012043 crude product Substances 0.000 claims abstract description 67
- 238000006243 chemical reaction Methods 0.000 claims abstract description 44
- 239000007787 solid Substances 0.000 claims abstract description 35
- 238000005406 washing Methods 0.000 claims abstract description 29
- 238000002156 mixing Methods 0.000 claims abstract description 28
- 239000003960 organic solvent Substances 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000012074 organic phase Substances 0.000 claims abstract description 24
- 230000008569 process Effects 0.000 claims abstract description 20
- 238000003756 stirring Methods 0.000 claims abstract description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 34
- 238000005516 engineering process Methods 0.000 claims description 32
- 230000003647 oxidation Effects 0.000 claims description 32
- 238000007254 oxidation reaction Methods 0.000 claims description 32
- 238000000746 purification Methods 0.000 claims description 32
- 238000000926 separation method Methods 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 26
- 150000002191 fatty alcohols Chemical class 0.000 claims description 19
- 235000010265 sodium sulphite Nutrition 0.000 claims description 18
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 17
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 17
- 229940117389 dichlorobenzene Drugs 0.000 claims description 17
- 239000012071 phase Substances 0.000 abstract description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 abstract 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 1
- 239000012535 impurity Substances 0.000 description 15
- 239000006227 byproduct Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 235000017471 coenzyme Q10 Nutrition 0.000 description 2
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 2
- 229940110767 coenzyme Q10 Drugs 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000010812 external standard method Methods 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
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Abstract
The invention discloses a method for separating and purifying 2,3,5-trimethyl benzoquinone. The method comprises the following steps of: 1, mixing a sodium hydrogensulfite solution and a crude product solution of 2,3,5-trimethyl benzoquinone, reacting with stirring, and filtering to obtain a filtrate and a solid; 2, washing the solid by using an organic solvent, and airing; and 3, mixing the aired solid and a sodium hydroxide solution, reacting with stirring, standing a reacted reaction solution, demixing to divide a water phase and an organic phase, washing the organic phase by using water, and drying by using anhydrous sodium sulfate to obtain the 2,3,5-trimethyl benzoquinone of which the mass purity is more than or equal to 99 percent. By the method, the harsh requirements of high vacuum and high temperature in the conventional process are avoided, so the method has the advantages of simple reaction process, high efficiency, convenience for operation and the like, and is an ideal method for separating and purifying the 2,3,5-trimethyl benzoquinone. According to the 2,3,5-trimethyl benzoquinone separated and purified by the method, the purity is over 99 percent, and the yield is more than or equal to 93 percent.
Description
Technical field
The invention belongs to chemosynthesis technical field, be specifically related to a kind of separation and purification 2,3, the method for 5-trimethylbenzoquinone.
Background technology
2,3,5-trimethylbenzoquinone (English name: 2; 3,5-trimethylbenzoquinone writes a Chinese character in simplified form TMBQ) be the important intermediate of synthesising complex E and Coenzyme Q10 99.0; Along with the continuous sharp increase of the whole world to living plain E and Coenzyme Q10 99.0 demand, the production of highly purified TMBQ extremely people is paid close attention in recent years.There is the method for the relevant TMBQ separation and purification that document can look into to mainly contain three kinds of steam distillation, rectification under vacuum method and very low temperature crystallization processs at present.Steam distillation is with a large amount of water vapour TMBQ to be taken out of, through oil phase, aqueous phase separation, again oil phase is carried out drying then, finally obtains high purity TMBQ; This method production efficiency is low, and energy consumption is higher, makes the TMBQ production cost significantly increase, and only in indivedual small-sized factories, uses.The rectification under vacuum method is under the high vacuum condition, through rectifying tower TMBQ is separated with impurity, obtains highly purified TMBQ; This method is high to vacuum requirements in operating process, and general requirement vacuum tightness is below the 100Pa, and the equipment early investment is bigger, in the big abroad factory of this method industrial applications is arranged.The very low temperature crystallization process is under-6 ℃～32 ℃ condition, under the condition that one or more auxiliary agents exist, makes the TMBQ recrystallization; This method not only needs multiple auxiliary agent, and in mother liquor, has 10%～20% TMBQ residual, is not suitable for industrial applications.
Summary of the invention
Technical problem to be solved by this invention is the deficiency to above-mentioned prior art, a kind of separation and purification 2,3 is provided, the method for 5-trimethylbenzoquinone.This method has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, is a kind of comparatively ideal 2,3, the separation purification method of 5-trimethylbenzoquinone.
For solving the problems of the technologies described above, the technical scheme that the present invention adopts is: a kind of separation and purification 2,3, and the method for 5-trimethylbenzoquinone is characterized in that, this method may further comprise the steps:
Step 2, with solid described in the step 1 with organic solvent washing 3～5 times, the solid after will washing then is air-dry;
Sodium sulfite solution described in the above-mentioned steps one is saturated sodium sulfite solution.
Described in the above-mentioned steps one 2,3, the crude product solution of 5-trimethylbenzoquinone is 2,3; 6-pseudocuminol chemical oxidation process obtain 2,3,5-trimethylbenzoquinone crude product solution, 2,3; 6-pseudocuminol catalyzed oxidation technology obtain 2,3,5-trimethylbenzoquinone crude product solution, unsym-trimethyl benzene chemical oxidation process obtain 2,3; 5-trimethylbenzoquinone crude product solution or unsym-trimethyl benzene catalyzed oxidation technology obtain 2,3,5-trimethylbenzoquinone crude product solution.
Described in the above-mentioned steps one 2,3, the organic solvent in the crude product solution of 5-trimethylbenzoquinone is one or more in aromatic hydrocarbon, chlorobenzene and the dichlorobenzene of the Fatty Alcohol(C12-C14 and C12-C18) of 3～12 carbon atoms, 6～9 carbon atoms.
Described in the above-mentioned steps one 2,3, in the crude product solution of 5-trimethylbenzoquinone 2,3, the volumetric molar concentration of 5-trimethylbenzoquinone is 0.05mol/L～2.5mol/L.
Organic solvent described in the above-mentioned steps two is the Fatty Alcohol(C12-C14 and C12-C18) of sherwood oil or 3～12 carbon atoms.
The temperature of reaction of stirring reaction described in the above-mentioned steps three is-6 ℃～25 ℃.
The mass concentration of sodium hydroxide solution described in the above-mentioned steps three is 10%～30%.
Described in the above-mentioned steps three in the sodium hydroxide solution amount of substance of the sodium sulfite anhy 96 in the amount of substance of sodium hydroxide and the sodium sulfite solution described in the step 1 equate.
The present invention compared with prior art has the following advantages:
1, method of the present invention has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, is a kind of comparatively ideal 2,3, the separation purification method of 5-trimethylbenzoquinone.
2, method of the present invention can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities, adopts 2,3 of method separation and purification of the present invention, and 5-trimethylbenzoquinone purity reaches more than 99%, and yield is not less than 93%.
Below in conjunction with accompanying drawing and embodiment, technical scheme of the present invention is done further to describe in detail.
Description of drawings
Fig. 1 is 2,3 of the embodiment of the invention 1, the gas chromatogram of 5-trimethylbenzoquinone crude product solution.
Fig. 2 is 2,3 after the embodiment of the invention 1 separation and purification, the gas chromatogram of 5-trimethylbenzoquinone.
Embodiment
Step 2, with solid described in the step 1 with petroleum ether 3 times, the solid after will washing then is air-dry at normal temperatures;
Adopt the gas chromatographic detection present embodiment used 2,3,5-trimethylbenzoquinone crude product solution, the result is as shown in Figure 1, as can be seen from the figure, and 2,3,5-trimethylbenzoquinone RT is 16.715min, and peak area is 695421.8, and peak area per-cent is 4.87%; Organic solvent propyl carbinol RT is 5.990min, and peak area is 13403264.2, and peak area per-cent is 93.85%; All the other are impurity peaks.Demarcate through external standard method, in the solution 2,3, the quality percentage composition of 5-trimethylbenzoquinone is 17.44%.
Adopt 2,3 of gas chromatographic detection present embodiment separation and purification, the 5-trimethylbenzoquinone, the result is as shown in Figure 2; As can be seen from the figure, 2,3; 5-trimethylbenzoquinone RT is 16.852min, and peak area is 10055541.2, and peak area per-cent is 99.27%; Demarcate 2,3 through external standard method, the quality percentage composition of 5-trimethylbenzoquinone is 99.33%.
Present embodiment has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities.2,3 of the method separation and purification of employing present embodiment, the quality purity of 5-trimethylbenzoquinone is 99.33%, yield reaches 95.0%.
Embodiment 2
Present embodiment is identical with embodiment 1, and wherein difference is: said 2,3; The crude product solution of 5-trimethylbenzoquinone is 2,3,6-pseudocuminol catalyzed oxidation technology obtain 2; 3,5-trimethylbenzoquinone crude product solution, unsym-trimethyl benzene chemical oxidation process obtain 2,3; 5-trimethylbenzoquinone crude product solution or unsym-trimethyl benzene catalyzed oxidation technology obtain 2,3,5-trimethylbenzoquinone crude product solution; Said 2; 3; Organic solvent in the crude product solution of 5-trimethylbenzoquinone is the Fatty Alcohol(C12-C14 and C12-C18) of propyl alcohol, 5～12 carbon atoms, aromatic hydrocarbon, chlorobenzene or the dichlorobenzene of 6～9 carbon atoms, perhaps is at least two kinds in aromatic hydrocarbon, chlorobenzene and the dichlorobenzene of the Fatty Alcohol(C12-C14 and C12-C18) of 3～12 carbon atoms, 6～9 carbon atoms.
Present embodiment has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities.2,3 of the method separation and purification of employing present embodiment, the quality purity of 5-trimethylbenzoquinone is that yield is not less than 93% more than 99%.
Step 2, with solid described in the step 1 with propyl alcohol washing 5 times, the solid after will washing then is air-dry at normal temperatures;
Present embodiment has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities.2,3 of the method separation and purification of employing present embodiment, the quality purity of 5-trimethylbenzoquinone is 99.4%, yield reaches 95.3%.
Embodiment 4
Present embodiment is identical with embodiment 3, and wherein difference is: said 2,3; The crude product solution of 5-trimethylbenzoquinone is 2,3,6-pseudocuminol chemical oxidation process obtain 2; 3,5-trimethylbenzoquinone crude product solution, unsym-trimethyl benzene chemical oxidation process obtain 2,3; 5-trimethylbenzoquinone crude product solution or unsym-trimethyl benzene catalyzed oxidation technology obtain 2,3,5-trimethylbenzoquinone crude product solution; Said 2; 3; Organic solvent in the crude product solution of 5-trimethylbenzoquinone is the Fatty Alcohol(C12-C14 and C12-C18) of 4～12 carbon atoms, aromatic hydrocarbon, chlorobenzene or the dichlorobenzene of 6～9 carbon atoms, perhaps is at least two kinds in aromatic hydrocarbon, chlorobenzene and the dichlorobenzene of the Fatty Alcohol(C12-C14 and C12-C18) of 3～12 carbon atoms, 6～9 carbon atoms.
Present embodiment has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities.2,3 of the method separation and purification of employing present embodiment, the quality purity of 5-trimethylbenzoquinone is that yield is not less than 93% more than 99%.
Embodiment 5
The 1500mL 2 that step 1, the saturated sodium sulfite solution that will contain the 0.2mol sodium sulfite anhy 96 and unsym-trimethyl benzene chemical oxidation process obtain; 3; The mixing of 5-trimethylbenzoquinone crude product solution obtains mixing solutions; Be stirring reaction 3h under 25 ℃ the condition with mixing solutions, obtain filtrating and solid after the filtration in temperature; Said 2,3, in the 5-trimethylbenzoquinone crude product solution 2,3, the concentration of 5-trimethylbenzoquinone is 0.05mol/L, and is said 2,3, and the solvent of 5-trimethylbenzoquinone crude product solution is a dodecanol;
Step 2, with solid described in the step 1 with petroleum ether 4 times, the solid after will washing then is air-dry at normal temperatures;
Present embodiment has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities.2,3 of the method separation and purification of employing present embodiment, the quality purity of 5-trimethylbenzoquinone is 99.58%, yield reaches 94.7%.
Embodiment 6
Present embodiment is identical with embodiment 5, and wherein difference is: said 2,3, the crude product solution of 5-trimethylbenzoquinone is 2; 3,6-pseudocuminol chemical oxidation process obtain 2,3,5-trimethylbenzoquinone crude product solution, 2; 3,6-pseudocuminol catalyzed oxidation technology obtain 2,3; 5-trimethylbenzoquinone crude product solution or unsym-trimethyl benzene catalyzed oxidation technology obtain 2,3,5-trimethylbenzoquinone crude product solution; Said 2; 3; Organic solvent in the crude product solution of 5-trimethylbenzoquinone is the Fatty Alcohol(C12-C14 and C12-C18) of 3～11 carbon atoms, aromatic hydrocarbon, chlorobenzene or the dichlorobenzene of 6～9 carbon atoms, perhaps is at least two kinds in aromatic hydrocarbon, chlorobenzene and the dichlorobenzene of the Fatty Alcohol(C12-C14 and C12-C18) of 3～12 carbon atoms, 6～9 carbon atoms.
Present embodiment has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities.2,3 of the method separation and purification of employing present embodiment, the quality purity of 5-trimethylbenzoquinone is that yield is not less than 93% more than 99%.
Embodiment 7
The 150mL 2 that step 1, the saturated sodium sulfite solution that will contain the 0.45mol sodium sulfite anhy 96 and unsym-trimethyl benzene catalyzed oxidation technology obtain; 3; The mixing of 5-trimethylbenzoquinone crude product solution obtains mixing solutions; Be stirring reaction 4h under 10 ℃ the condition with mixing solutions, obtain filtrating and solid after the filtration in temperature; Said 2,3, in the 5-trimethylbenzoquinone crude product solution 2,3, the concentration of 5-trimethylbenzoquinone is 1mol/L, and is said 2,3, and the solvent of 5-trimethylbenzoquinone crude product solution is the mixed solvent of benzene and dichlorobenzene;
Step 2, with solid described in the step 1 with petroleum ether 5 times, the solid after will washing then is air-dry at normal temperatures;
Present embodiment has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities.2,3 of the method separation and purification of employing present embodiment, the quality purity of 5-trimethylbenzoquinone is 99.61%, yield reaches 93.5%.
Present embodiment is identical with embodiment 7, and wherein difference is: said 2,3, the crude product solution of 5-trimethylbenzoquinone is 2; 3,6-pseudocuminol chemical oxidation process obtain 2,3,5-trimethylbenzoquinone crude product solution, 2; 3,6-pseudocuminol catalyzed oxidation technology obtain 2,3; 5-trimethylbenzoquinone crude product solution or unsym-trimethyl benzene chemical oxidation process obtain 2,3,5-trimethylbenzoquinone crude product solution; Said 2; 3; Organic solvent in the crude product solution of 5-trimethylbenzoquinone is a kind of in aromatic hydrocarbon, chlorobenzene and the dichlorobenzene of the Fatty Alcohol(C12-C14 and C12-C18) of 3～12 carbon atoms, 6～9 carbon atoms or more than three kinds; Perhaps being two kinds in aromatic hydrocarbon and the chlorobenzene of the Fatty Alcohol(C12-C14 and C12-C18) of 3～12 carbon atoms, 6～9 carbon atoms, perhaps is the mixed solvent of a kind of and dichlorobenzene in aromatic hydrocarbon and the chlorobenzene of the Fatty Alcohol(C12-C14 and C12-C18) of 3～12 carbon atoms, 7～9 carbon atoms.
Present embodiment has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities.2,3 of the method separation and purification of employing present embodiment, the quality purity of 5-trimethylbenzoquinone is that yield is not less than 93% more than 99%.
Embodiment 9
Step 2, with solid described in the step 1 with dodecanol washing 3 times, the solid after will washing then is air-dry at normal temperatures;
Present embodiment has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities.2,3 of the method separation and purification of employing present embodiment, the quality purity of 5-trimethylbenzoquinone is 99.48%, yield reaches 94.8%.
Present embodiment is identical with embodiment 9, and wherein difference is: said 2,3; The crude product solution of 5-trimethylbenzoquinone is 2,3,6-pseudocuminol catalyzed oxidation technology obtain 2; 3,5-trimethylbenzoquinone crude product solution, unsym-trimethyl benzene chemical oxidation process obtain 2,3; 5-trimethylbenzoquinone crude product solution or unsym-trimethyl benzene catalyzed oxidation technology obtain 2,3,5-trimethylbenzoquinone crude product solution; Said 2; 3; Organic solvent in the crude product solution of 5-trimethylbenzoquinone be in aromatic hydrocarbon, chlorobenzene and the dichlorobenzene of the Fatty Alcohol(C12-C14 and C12-C18) of 3～12 carbon atoms, 6～9 carbon atoms a kind of, more than two kinds or four kinds; Perhaps be three kinds in aromatic hydrocarbon and the chlorobenzene of the Fatty Alcohol(C12-C14 and C12-C18) of 3～12 carbon atoms, 6～9 carbon atoms; Perhaps being in the aromatic hydrocarbon of Fatty Alcohol(C12-C14 and C12-C18) and 6～9 carbon atoms of 3～12 carbon atoms the two kinds mixed solvents with dichlorobenzene, perhaps is the mixed solvent of a kind of and chlorobenzene and dichlorobenzene in the aromatic hydrocarbon of Fatty Alcohol(C12-C14 and C12-C18) and 6～9 carbon atoms of 3～11 carbon atoms.
Present embodiment has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities.2,3 of the method separation and purification of employing present embodiment, the quality purity of 5-trimethylbenzoquinone is that yield is not less than 93% more than 99%.
Embodiment 11
The 100mL 2 that step 1, the saturated sodium sulfite solution that will contain the 0.8mol sodium sulfite anhy 96 and unsym-trimethyl benzene chemical oxidation process obtain; 3; The mixing of 5-trimethylbenzoquinone crude product solution obtains mixing solutions; Be stirring reaction 4h under-6 ℃ the condition with mixing solutions, obtain filtrating and solid after the filtration in temperature; Said 2,3, in the 5-trimethylbenzoquinone crude product solution 2,3, the concentration of 5-trimethylbenzoquinone is 2.0mol/L, and is said 2,3, and the solvent of 5-trimethylbenzoquinone crude product solution is a chlorobenzene;
Step 2, with solid described in the step 1 with propyl carbinol washing 4 times, the solid after will washing then is air-dry at normal temperatures;
Present embodiment has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities.2,3 of the method separation and purification of employing present embodiment, the quality purity of 5-trimethylbenzoquinone is 99%, yield is 93%.
Embodiment 12
Present embodiment is identical with embodiment 11, and wherein difference is: said 2,3, the crude product solution of 5-trimethylbenzoquinone is 2; 3,6-pseudocuminol chemical oxidation process obtain 2,3,5-trimethylbenzoquinone crude product solution, 2; 3,6-pseudocuminol catalyzed oxidation technology obtain 2,3; 5-trimethylbenzoquinone crude product solution or unsym-trimethyl benzene catalyzed oxidation technology obtain 2,3,5-trimethylbenzoquinone crude product solution; Said 2; 3; Organic solvent in the crude product solution of 5-trimethylbenzoquinone is the Fatty Alcohol(C12-C14 and C12-C18) of 3～12 carbon atoms, the aromatic hydrocarbon or the dichlorobenzene of 6～9 carbon atoms, perhaps is at least two kinds in aromatic hydrocarbon, chlorobenzene and the dichlorobenzene of the Fatty Alcohol(C12-C14 and C12-C18) of 3～12 carbon atoms, 6～9 carbon atoms.
Present embodiment has been avoided the harsh requirement of the high vacuum in the traditional technology, pyritous, and it is simple to have reaction process, and efficient is high, be convenient to advantage such as operation, can make 2,3, and the 5-trimethylbenzoquinone separates rapidly with organic solvent, by-product impurities.2,3 of the method separation and purification of employing present embodiment, the quality purity of 5-trimethylbenzoquinone is that yield is not less than 93% more than 99%.
The above; It only is preferred embodiment of the present invention; Be not that the present invention is done any restriction, every according to inventing technical spirit to any simple modification, change and equivalent structure variation that above embodiment did, all still belong in the protection domain of technical scheme of the present invention.
Claims (10)
1. separation and purification 2,3, the method for 5-trimethylbenzoquinone is characterized in that, this method may further comprise the steps:
Step 1, with sodium sulfite solution and 2,3, the crude product solution of 5-trimethylbenzoquinone is mixed and to be obtained mixing solutions, be stirring reaction 3h～5h under-6 ℃～25 ℃ the condition in temperature with mixing solutions, obtains after the filtration filtrating and solid; Sodium sulfite anhy 96 and 2,3 in the said mixing solutions, the mol ratio of 5-trimethylbenzoquinone is not less than 2: 1;
Step 2, with solid described in the step 1 with organic solvent washing 3～5 times, the solid after will washing then is air-dry;
Step 3, the solid after air-dry in the step 2 is mixed with sodium hydroxide solution, stirring reaction 0.5h～1.5h with reacted reaction solution standing demix, tells water and organic phase then; Organic phase with water washing 2～3 times, is used anhydrous sodium sulfate drying at last, obtain quality purity be not less than 99% 2,3, the 5-trimethylbenzoquinone.
2. a kind of separation and purification 2,3 according to claim 1, the method for 5-trimethylbenzoquinone is characterized in that, sodium sulfite solution described in the step 1 is saturated sodium sulfite solution.
3. a kind of separation and purification 2,3 according to claim 1, the method for 5-trimethylbenzoquinone is characterized in that, sodium sulfite anhy 96 and 2,3 in the mixing solutions described in the step 1, the mol ratio of 5-trimethylbenzoquinone is 2～3: 1.
4. a kind of separation and purification 2,3 according to claim 1, the method for 5-trimethylbenzoquinone is characterized in that; Described in the step 12,3, the crude product solution of 5-trimethylbenzoquinone is 2,3; 6-pseudocuminol chemical oxidation process obtain 2,3,5-trimethylbenzoquinone crude product solution, 2,3; 6-pseudocuminol catalyzed oxidation technology obtain 2,3,5-trimethylbenzoquinone crude product solution, unsym-trimethyl benzene chemical oxidation process obtain 2,3; 5-trimethylbenzoquinone crude product solution or unsym-trimethyl benzene catalyzed oxidation technology obtain 2,3,5-trimethylbenzoquinone crude product solution.
5. a kind of separation and purification 2 according to claim 1; 3; The method of 5-trimethylbenzoquinone is characterized in that, described in the step 12; 3, the organic solvent in the crude product solution of 5-trimethylbenzoquinone is one or more in aromatic hydrocarbon, chlorobenzene and the dichlorobenzene of the Fatty Alcohol(C12-C14 and C12-C18) of 3～12 carbon atoms, 6～9 carbon atoms.
6. a kind of separation and purification 2,3 according to claim 1, the method for 5-trimethylbenzoquinone is characterized in that, described in the step 12,3, in the crude product solution of 5-trimethylbenzoquinone 2,3, the volumetric molar concentration of 5-trimethylbenzoquinone is 0.05mol/L～2.5mol/L.
7. a kind of separation and purification 2,3 according to claim 1, the method for 5-trimethylbenzoquinone is characterized in that, organic solvent described in the step 2 is the Fatty Alcohol(C12-C14 and C12-C18) of sherwood oil or 3～12 carbon atoms.
8. a kind of separation and purification 2,3 according to claim 1, the method for 5-trimethylbenzoquinone is characterized in that, the temperature of reaction of stirring reaction described in the step 3 is-6 ℃～25 ℃.
9. a kind of separation and purification 2,3 according to claim 1, the method for 5-trimethylbenzoquinone is characterized in that, the mass concentration of sodium hydroxide solution described in the step 3 is 10%～30%.
10. a kind of separation and purification 2 according to claim 1; 3; The method of 5-trimethylbenzoquinone is characterized in that, described in the step 3 in the sodium hydroxide solution amount of substance of the sodium sulfite anhy 96 in the amount of substance of sodium hydroxide and the sodium sulfite solution described in the step 1 equate.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN88102750A (en) * | 1987-05-13 | 1988-11-30 | 卫材株式会社 | Preparation method of 2, 3, 5-trimethylbenzoquinone |
| CN102108047A (en) * | 2010-12-06 | 2011-06-29 | 上海迪赛诺医药发展有限公司 | Method for preparing 2,3,5-trimethylhydroquinone |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN88102750A (en) * | 1987-05-13 | 1988-11-30 | 卫材株式会社 | Preparation method of 2, 3, 5-trimethylbenzoquinone |
| CN102108047A (en) * | 2010-12-06 | 2011-06-29 | 上海迪赛诺医药发展有限公司 | Method for preparing 2,3,5-trimethylhydroquinone |
Non-Patent Citations (2)
| Title |
|---|
| 吴西宁等: "催化氧化法制2,3,5-三甲基苯醌", 《工业催化》 * |
| 李雄 等: "2,3,5-三甲基苯醌的合成研究", 《湖南化工》 * |
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