CN102796035A - Condensation method of m-,p-mixed di-(tert-butyl isopropyl peroxide)benzene - Google Patents
Condensation method of m-,p-mixed di-(tert-butyl isopropyl peroxide)benzene Download PDFInfo
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- CN102796035A CN102796035A CN2012103279224A CN201210327922A CN102796035A CN 102796035 A CN102796035 A CN 102796035A CN 2012103279224 A CN2012103279224 A CN 2012103279224A CN 201210327922 A CN201210327922 A CN 201210327922A CN 102796035 A CN102796035 A CN 102796035A
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Abstract
The invention discloses a condensation method of m-,p-mixed di-(tert-butyl isopropyl peroxide)benzene. In the method, di-(2-hydroxy-2-propyl)benzene and tert-butyl hydrogen peroxide are taken as starting raw materials; perchloric acid of which the concentration is 50-52 percent by weight is taken as a catalyst; 6# solvent oil is taken as a solvent; the molar ratio of di-(2-hydroxy-2-propyl)benzene to tert-butyl hydrogen peroxide is 1:(2.30-2.90); the weight ratio of di-(2-hydroxy-2-propyl)benzene to perchloric acid is 100:(0.35-0.75); and the weight ratio of di-(2-hydroxy-2-propyl)benzene to 6# solvent oil is 100:(250-410). The method comprises the following steps of: controlling the reaction temperature at 39-56 DEG C and controlling the reaction pressure at 0-0.056MPa for performing a reduced pressure nitrogen bubbling dehydration reflux condensation reaction; after reacting to a final point, adding an alkali for terminating the reaction; washing a reaction liquid with an alkali water and water to obtain a condensation liquid; and concentrating the condensation liquid to obtain di-(tert-butyl isopropyl peroxide)benzene. The method has the characteristics of easiness in controlling reaction, short condensation reaction time, small quantity of side products and high yield.
Description
Technical field
The present invention relates to organic chemical synthesis process, refer in particular to the method for condensing that a kind of, contraposition mix two-(tert-butyl hydroperoxide sec.-propyl) benzene.
Background technology
At present with two-(2-hydroxyl-2-propyl group) benzene (be called for short DC) be organo-peroxide two-(tert-butyl hydroperoxide sec.-propyl) benzene (Di-(2-tert-butyl peroxy isopropyl) benzene; Hereinafter to be referred as DBP) and the important starting raw material of midbody monomer superoxide tertbutyl peroxide (be called for short TBHP); Between, contraposition mixes two-condensation synthetic technology that (tert-butyl hydroperoxide sec.-propyl) benzene generally adopts and is to use the vitriol oil as catalyzer; Its shortcoming is that temperature of reaction is low; Generally need be controlled at 0～15 ℃, overtemperature causes decomposition easily, reduces the DBP yield; Because vitriol oil acidity is strong, condensation reaction is than difficult control, progressively carbonization of material in reaction, color blackening, reduction product quality and yield simultaneously.
Simultaneously, as the moisture that contains among the TBHP that uses in the above-mentioned reaction about 30%, and in producing, before reaction, remove the moisture among the TBHP, and in condensation reaction, do not take nitrogen bubble to remove reaction water, make the reaction times prolong and the reduction yield.
Summary of the invention
The object of the present invention is to provide a kind of, contraposition to mix two-(tert-butyl hydroperoxide sec.-propyl) benzene method of condensing; Overcome the shortcoming of existing technology; Make condensation reaction more easy to control, shorten the reaction times, reduce side reaction, improve yield and improve product quality.
The object of the invention realizes through following technical proposals: a kind of, contraposition mix the method for condensing of two-(tert-butyl hydroperoxide sec.-propyl) benzene; With DC and TBHP is starting raw material; Characteristics are that to adopt weight percent concentration be that 50%～52% perchloric acid is as catalyzer; With 6# solvent oil (being called rubber solvent naphtha again, 80 ~ 120 ℃ of boiling ranges) is solvent, may further comprise the steps at least:
(1) each material proportion: DC:TBHP (mol ratio) 1
:2
.30～2
.90; DC: perchloric acid (weight ratio) 100
:0.35～0
.75, DC:6
#Solvent oil (weight ratio) 100
:250～410;
(2) in the condensation still, press formula ratio and add solvent 6 earlier
#Behind the solvent oil, begin to stir and add TBHP, through stirring 20～30 minutes, 20～30 ℃ of controlled temperature, extraction, standing demix dewater;
(3) under whipped state, the DC that measures by the proportion scale input under the room temperature condition drops into the condensation reaction still, drops into perchloric acid then; Open condensation still chuck hot water and heat up, control still temperature is driven vacuum pump and is vacuumized at 39～56 ℃; Keep reaction pressure 0～-0.056MPa, carry out N at the bottom of the still simultaneously
2Bubbling is accomplished the reflux dewatering reaction;
(4) condensation reaction gas phase is after the condensation condenser condenses, and noncondensable gas high altitude discharge, lime set oil-feed water separator separate, solvent 6
#Solvent oil from top overflow go into water-and-oil separator and separate solvent 6
#The solvent oil into condensation still that refluxes recycles;
(5) react after 3 hours, sampling analysis, the content of monitoring midbody monomer superoxide is when single superoxide TBHP content≤3
.During 0%wt, reaction finishes, be cooled to below 45 ℃ after, slowly in still, add 3～5% alkali lye termination reactions;
(6) after the termination reaction, be cooled to reaction solution below 40 ℃, add alkali lye again and carry out alkali cleaning and washing, reach 6.5～7.5 to condensated liquid pH value, the buck of washing is put into condensation salkali waste groove, and washing water are put into the condensation waste water groove, and condensated liquid is put to thick DCB groove;
(7) with the condensated liquid input carry carry in the dense device dense: adopt and to carry dense with water azeotropic decompression desolventizing and decompression nitrogen bubble technology; Control concentration liquid phase temperature is at 50～80 ℃; Pressure-0.095MPa～normal pressure; Deviate from solvent after condenser condenses, advance to carry dense top liquid bath and reclaim, the upgrading system vacuum provides by carrying dense vacuum pump;
(8) concentration liquid is put the insulation of carrying out concentration liquid to the discharging still, supplies finished product to handle the hilllock and carries out the BIPB flaking.Between obtaining, contraposition mixes two-(tert-butyl hydroperoxide sec.-propyl) benzene (being called for short DBP).
The principle of the invention is following:
(1) condensation principle:
Main reaction (is example with p-DC):
Side reaction (is example with p-DC):
(2) put forward dense principle:
Utilize the difference of different liquid phase substance boiling points, under 50～80 ℃ of temperature, under pressure-0.095～condition of normal pressure, the light constituent in the mixing liquid is volatilized to reach the purpose of purification.Obtain two-(tert-butyl hydroperoxide sec.-propyl) benzene (being called for short DBP).
Use low perchloric acid to replace the vitriol oil, the DBP yield is brought up to more than 95% from 85% as reducing side reaction.Remove reaction water with nitrogen bubble, can improve the security of system, shorten the reaction times simultaneously.
Wherein, the washing described in the step (6) is closed water intaking valve behind the water yield 200～500kg, stirs after 20～30 minutes, stops stirring, leave standstill 20～30 minutes after, draining.
On the such scheme basis, describedly to put forward dense process and divide and add tap water 2～3 times, the add-on that single still is carried dense whole process tap water is not more than concentration liquid total amount 10%.
Beneficial effect of the present invention: make condensation reaction more easy to control, shorten the reaction times, reduce side reaction, improve yield and improve product quality.Use lower concentration 50%～52% perchloric acid to replace the vitriol oil, can reduce side reaction, the DBP yield is brought up to more than 95% from 85% as catalyzer.Remove reaction water with nitrogen bubble, can improve the security of system, shortened the reaction times simultaneously.
Description of drawings
Fig. 1 reaction formula 1 is main reaction;
Fig. 2 reaction formula 2 is side reaction.
Embodiment
A kind of, contraposition mix the method for condensing of two-(tert-butyl hydroperoxide sec.-propyl) benzene; With DC and TBHP is starting raw material; Adopting weight percent concentration is that 50%～52% perchloric acid is as catalyzer; With 6# solvent oil (being called rubber solvent naphtha again, 80 ~ 120 ℃ of boiling ranges) is solvent, and each material proportion is:
DC:TBHP (mol ratio) 1
:2
.30～2
.90;
DC: perchloric acid (weight ratio) 100
:0.35～0
.75;
DC:6
#Solvent oil (weight ratio) 100
:250～410.
Embodiment 1
Between, the contraposition condensation compound method exploration following steps of mixing two-(tert-butyl hydroperoxide sec.-propyl) benzene (DBP):
By filling a prescription earlier with 900kg6
#Solvent oil drops in the condensation still, opens and stirs;
By prescription 178kgTBHP is dropped into the condensation still, 23 ℃ of controlled temperature stirred 25 minutes, and moisture is got rid of in sedimentation 30 minutes, because content 70 ± 1 % TBHP water cut that market is bought are high, must dewater through extraction;
About 20 ℃ of still temperature, in the condensation reaction still, drop into the smart DC of 300kg, 1.2kg perchloric acid by prescription in regular turn, heated up through the chuck hot water that hot water pump provides by the elevated temperature heat tank, open condensation still chuck hot water and heat up, control still temperature is at 42 ± 1 ℃;
Drive the condensation vacuum pump and vacuumize, reaction pressure is controlled at-0.052MPa, from device N
2Surge tank (P<0.15MPa) N at the bottom of still is carried out in needle valve, the control of on-the-spot under meter
2Bubbling carries out " decompression, N
2Bubbling " the reflux dewatering reaction;
The condensation reaction gas phase is after the condensation condenser condenses, and noncondensable gas high altitude discharge, lime set oil-feed water separator separate, solvent 6
#Solvent oil from top overflow go into water-and-oil separator and separate solvent 6
#The solvent oil into condensation still that refluxes;
React after 3 hours sampling analysis, the content of monitoring midbody list superoxide; Come budgetary estimate to reach the time of condensation reaction terminal point according to the sampling analysis data; React single peroxide level≤1.9%Wt after 4.5 hours, reach reaction end, let out to normal pressure by the nitrogen that blasts in the condensation still; By inner coil pipe water quench reaction solution, slowly in the condensation lye vat, adding concentration when being cooled to below 45 ℃ is the aqueous sodium hydroxide solution 100kg termination reaction of 3～5%wt;
After the termination reaction, continue to be cooled to reaction solution below 40 ℃, add again that alkali lye carries out alkali cleaning in the condensation lye vat, stir after 23 minutes, stop stirring by the inner coil pipe water coolant, leave standstill 30 minutes after, open still bottom valve row alkali, the buck of washing is put into condensation salkali waste groove;
Add water washing, close water intaking valve behind the water yield 300kg, stir after 23 minutes; Stop stirring, leave standstill 30 minutes after, in draining to the condensation waste water groove; Carry out the second time or washing for the third time by this, survey washing water layer PH=7.1, put to thick DBP groove through the condensated liquid of alkali cleaning and washing;
With the 300kg condensated liquid from thick DBP groove with nitrogen pressure to carrying in the dense device, the hot water that is provided through hot water pump by the elevated temperature heat tank advances the chuck heating, adopts and carries dense with water azeotropic decompression desolventizing and decompression nitrogen bubble technology; Concentration liquid phase temperature is at 50～80 ℃; Pressure-0.095MPa～normal pressure in putting forward dense process, divides and adds tap water 3 times; The add-on that single still is carried dense whole process tap water is not more than concentration liquid total amount 10%; Obtain DBP, deviate from solvent after condenser condenses, advance to carry dense top liquid bath and reclaim.The upgrading system vacuum provides by carrying dense vacuum pump.
Concentration liquid is put the insulation of carrying out concentration liquid to the discharging still, supplies finished product to handle the hilllock and carries out the DBP flaking, between obtaining, contraposition mixes two-(tert-butyl hydroperoxide sec.-propyl) benzene.
Embodiment 2
Between, the contraposition condensation compound method of mixing two-(tert-butyl hydroperoxide sec.-propyl) benzene (DBP) may further comprise the steps at least:
By filling a prescription earlier with 1200kg6
#Solvent oil drops in the condensation still, opens and stirs;
By prescription 238kgTBHP is dropped into the condensation still, 25 ℃ of controlled temperature stirred 25 minutes, and moisture is got rid of in sedimentation 30 minutes;
By prescription about 20 ℃ of still temperature with the smart DC input of 400kg condensation reaction still;
By prescription about 20 ℃ of still temperature with 1.6kg perchloric acid input condensation reaction still;
Open condensation still chuck hot water and heat up, control still temperature is at 45 ± 1 ℃;
Drive vacuum pump and vacuumize, reaction pressure is controlled at-0.053MPa, carries out N at the bottom of the still simultaneously
2Bubbling carries out " decompression, N
2Bubbling " the reflux dewatering reaction;
React after 3 hours, sampling analysis comes budgetary estimate to reach the time of condensation reaction terminal point according to the sampling analysis data, reacts single peroxide level=2.9%Wt after 4.8 hours, and reaction finishes;
After being cooled to below 45 ℃, in still, add 3～5% aqueous sodium hydroxide solution 120kg termination reaction;
Stir after 25 minutes, stop stirring, leave standstill 30 minutes after, open still bottom valve row alkali;
Add water washing, close water intaking valve behind the water yield 350kg, stir after 25 minutes, stop stirring, leave standstill 30 minutes after, draining.Carry out the second time or washing for the third time by this, survey washing water layer PH=6.8;
350kg condensated liquid input is carried dense device, control concentration liquid phase temperature at 50～80 ℃, pressure-0.095MPa～normal pressure.Divide and add tap water 3 times putting forward dense process, the add-on that single still is carried dense whole process tap water is not more than concentration liquid total amount 10%.Obtain DBP.
Embodiment 3
Between, the contraposition condensation compound method of mixing two-(tert-butyl hydroperoxide sec.-propyl) benzene (DBP) may further comprise the steps at least:
By filling a prescription earlier with 1500kg6
#Solvent oil drops in the condensation still, opens and stirs;
By prescription 298kgTBHP is dropped into the condensation still, 28 ℃ of controlled temperature stirred 30 minutes, and moisture is got rid of in sedimentation 30 minutes;
, in the condensation reaction still, drop in regular turn about 20 ℃ of still temperature by prescription the smart DC of 500kg, 2.0kg perchloric acid;
Open condensation still chuck hot water and heat up, control still temperature is at 48 ± 1 ℃;
Drive vacuum pump and vacuumize, reaction pressure is controlled at-0.055MPa, carries out N at the bottom of the still simultaneously
2Bubbling carries out " decompression, N
2Bubbling " the reflux dewatering reaction;
React after 3 hours, sampling analysis comes budgetary estimate to reach the time of condensation reaction terminal point according to the sampling analysis data, reacts single peroxide level=2.2%Wt after 4.9 hours, and reaction finishes;
After being cooled to below 45 ℃, in still, add 3～5% aqueous sodium hydroxide solution 150kg termination reaction;
Stir after 25 minutes, stop stirring, leave standstill 30 minutes after, open still bottom valve row alkali;
Add water washing, close water intaking valve behind the water yield 450kg, stir after 25 minutes, stop stirring, leave standstill 30 minutes after, draining is carried out second time or washing for the third time by this, surveys and washs water layer PH=6.9;
450kg condensated liquid input is carried dense device, control concentration liquid phase temperature at 50～80 ℃, pressure-0.095MPa～normal pressure.Divide and add tap water 2 times putting forward dense process, the add-on that single still is carried dense whole process tap water is not more than said concentration liquid total amount 10%, obtains DBP.
Should be appreciated that after having read foregoing invention content of the present invention, those of ordinary skills can do various changes or modification to the present invention, these equivalent form of values modification fall into equally in the protection domain that the said claims of the application are limited.
Claims (3)
1. between one kind, contraposition mixes the method for condensing of two-(tert-butyl hydroperoxide sec.-propyl) benzene; With two-(2-hydroxyl-2-propyl group) benzene and tertbutyl peroxide is starting raw material; It is characterized in that: adopting weight percent concentration is that 50%～52% perchloric acid is as catalyzer; With the 6# solvent oil is solvent, may further comprise the steps at least:
(1) by following each material of prescription weighing, each material proportion is:
Two-(2-hydroxyl-2-propyl group) benzene: tertbutyl peroxide (mol ratio) 1
:2
.30～2
.90;
Two-(2-hydroxyl-2-propyl group) benzene: perchloric acid (weight ratio) 100
:0.35～0
.75;
Two-(2-hydroxyl-2-propyl group) benzene: 6
#Solvent oil (weight ratio) 100
:250～410;
(2) in the condensation still, press formula ratio and add solvent 6 earlier
#Behind the solvent oil, begin to stir and add TBHP, through stirring 20～30 minutes, 20～30 ℃ of controlled temperature, extraction, standing demix dewater;
(3) under whipped state, the DC that measures by the proportion scale input under the room temperature condition drops into the condensation reaction still, drops into perchloric acid then; Open condensation still chuck hot water and heat up, control still temperature is driven vacuum pump and is vacuumized at 39～56 ℃; Keep reaction pressure 0～-0.056MPa, carry out N at the bottom of the still simultaneously
2Bubbling is accomplished the reflux dewatering reaction;
(4) condensation reaction gas phase is after the condensation condenser condenses, and noncondensable gas high altitude discharge, lime set oil-feed water separator separate, solvent 6
#Solvent oil from top overflow go into water-and-oil separator and separate solvent 6
#The solvent oil into condensation still that refluxes recycles;
(5) react after 3 hours, sampling analysis, the content of monitoring midbody monomer superoxide is when single superoxide TBHP content≤3
.During 0%wt, reaction finishes, be cooled to below 45 ℃ after, slowly in still, add 3～5% alkali lye termination reactions;
(6) after the termination reaction, be cooled to reaction solution below 40 ℃, add alkali lye again and carry out alkali cleaning and washing, reach 6.5～7.5 to condensated liquid pH value, the buck of washing is put into condensation salkali waste groove, and washing water are put into the condensation waste water groove, and condensated liquid is put to thick DBP groove;
(7) condensated liquid is carried dense: the condensated liquid input is carried in the dense device; Adopt and carry dense with water azeotropic decompression desolventizing and decompression nitrogen bubble technology; Control concentration liquid phase temperature is at 50～80 ℃, and pressure-0.095MPa～normal pressure deviates from solvent after condenser condenses; Advance to carry dense top liquid bath and reclaim, the upgrading system vacuum provides by carrying dense vacuum pump;
(8) concentration liquid is put the insulation of carrying out concentration liquid to the discharging still, and supply finished product to handle the hilllock and carry out the BIPB flaking,
Between obtaining, contraposition mixes two-(tert-butyl hydroperoxide sec.-propyl) benzene.
2. according to claim 1, contraposition mix the method for condensing of two-(tert-butyl hydroperoxide sec.-propyl) benzene; It is characterized in that: the washing described in the described step (6); Close water intaking valve behind the water yield 200～500kg, stir after 20～30 minutes, stop stirring; After leaving standstill 20～30 minutes, draining.
3. according to claim 1, contraposition mix the method for condensing of two-(tert-butyl hydroperoxide sec.-propyl) benzene; It is characterized in that: describedly put forward dense process and divide and add tap water 2～3 times, the add-on that single still is carried dense whole process tap water is not more than concentration liquid gross weight 10%.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103058908A (en) * | 2012-12-25 | 2013-04-24 | 宁波东来化工有限公司 | One-step synthetic method for bis(t-butylperoxyisopropyl)benzene |
| CN106588735A (en) * | 2015-10-20 | 2017-04-26 | 中国石油化工集团公司 | Bis(t-butylperoxyisopropyl)benzene production method |
| CN106898719A (en) * | 2017-02-14 | 2017-06-27 | 珠海光宇电池有限公司 | Lithium battery diaphragm and preparation method thereof and the lithium battery using the barrier film |
| CN113999151A (en) * | 2021-12-01 | 2022-02-01 | 广西东岚新材料有限公司 | Condensation reaction method for synthesizing meta-position and para-position 2- (tert-butyl peroxyisopropyl) benzene |
| CN114920681A (en) * | 2022-05-27 | 2022-08-19 | 山东阳谷华泰化工股份有限公司 | Synthesis method of di (tert-butyl peroxy isopropyl) benzene |
| CN115010637A (en) * | 2022-06-14 | 2022-09-06 | 万华化学集团股份有限公司 | Method for preparing m-dihydrohydroperoxide cumene |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103058908A (en) * | 2012-12-25 | 2013-04-24 | 宁波东来化工有限公司 | One-step synthetic method for bis(t-butylperoxyisopropyl)benzene |
| CN106588735A (en) * | 2015-10-20 | 2017-04-26 | 中国石油化工集团公司 | Bis(t-butylperoxyisopropyl)benzene production method |
| CN106898719A (en) * | 2017-02-14 | 2017-06-27 | 珠海光宇电池有限公司 | Lithium battery diaphragm and preparation method thereof and the lithium battery using the barrier film |
| CN106898719B (en) * | 2017-02-14 | 2019-09-10 | 珠海光宇电池有限公司 | Lithium battery diaphragm and preparation method thereof and the lithium battery for using the diaphragm |
| CN113999151A (en) * | 2021-12-01 | 2022-02-01 | 广西东岚新材料有限公司 | Condensation reaction method for synthesizing meta-position and para-position 2- (tert-butyl peroxyisopropyl) benzene |
| CN114920681A (en) * | 2022-05-27 | 2022-08-19 | 山东阳谷华泰化工股份有限公司 | Synthesis method of di (tert-butyl peroxy isopropyl) benzene |
| CN115010637A (en) * | 2022-06-14 | 2022-09-06 | 万华化学集团股份有限公司 | Method for preparing m-dihydrohydroperoxide cumene |
| CN115010637B (en) * | 2022-06-14 | 2023-09-19 | 万华化学集团股份有限公司 | Method for preparing m-dihydrobenzene |
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Application publication date: 20121128 |