CN103058908A - One-step synthetic method for bis(t-butylperoxyisopropyl)benzene - Google Patents
One-step synthetic method for bis(t-butylperoxyisopropyl)benzene Download PDFInfo
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- CN103058908A CN103058908A CN2012105741311A CN201210574131A CN103058908A CN 103058908 A CN103058908 A CN 103058908A CN 2012105741311 A CN2012105741311 A CN 2012105741311A CN 201210574131 A CN201210574131 A CN 201210574131A CN 103058908 A CN103058908 A CN 103058908A
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Abstract
The invention relates to preparation of an organic peroxide initiator and aims to provide a one-step synthetic method for bis(t-butylperoxyisopropyl)benzene. The method comprises the following steps: (1) successively adding tert-butyl hydroperoxide, 2-isopropyl benzene alcohol and a catalyst NaClO4 into a reaction vessel placed in a water bath and then slowly adding sulfuric acid with a mass concentration of 70%, wherein water-bath temperature is controlled to be 30 to 55 DEG C and reaction time is controlled to be 30 to 50 min; and (2) adding desalinized water to terminate a reaction, carrying out standing for layering, repeatedly washing an organic phase taken from an upper layer with water and alkali many times and carrying out drying so as to obtain a final product. The synthetic method provided by the invention has mild reaction conditions and enables high yield and product purity of more than 95% to be realized. Meanwhile, waste liquid except the target product can be recycled in peroxidation and tert-butylation, which is beneficial for environmental protection and enables production raw materials to be saved.
Description
Technical field
The present invention relates to a kind of preparation method of organic peroxide evocating agent, more specifically is the preparation method of a kind of organo-peroxide two (tert-butyl hydroperoxide sec.-propyl) benzene, belongs to the field of chemical synthesis.
Background technology
Two (tert-butyl hydroperoxide isopropyl) benzene (ZR-BIPB) are the upgrading products of DCP, be commonly called as " tasteless DCP ", consumption is only second to the dialkyl group organo-peroxide linking agent of DCP, is the novel peroxide product of realizing abroad suitability for industrialized production the beginning of the sixties in last century.Contain two peroxide bridges in two (tert-butyl hydroperoxide sec.-propyl) benzene molecular, belong to two peralcohol, its theoretical active o content is 9.45%.The free radical that is produced by two (tert-butyl hydroperoxide sec.-propyl) benzene thermolysis has higher stability, can be used as the linking agent of the rubber such as polyethylene, terpolymer EP rubber, ethene one acetate ethylene copolymer, silicon rubber, paracril and plastics.In the situation of equal cross-linking effect, addition only is 2/3 of DCP.Two (tert-butyl hydroperoxide sec.-propyl) benzene does not all have the crosslinked stink of DCP in cross-linking process or finished product.Two (tert-butyl hydroperoxide sec.-propyl) benzene cross-linking efficiency is high, and the thermotolerance of goods, cryogenic subduing flexibility and withstand voltage deformability are all better.
The synthetic method of two (tert-butyl hydroperoxide isopropyl) benzene has four kinds:
1) in the presence of an acidic catalyst, the condensation reaction with two-(2-hydroxyl sec.-propyl) benzene and tertbutyl peroxide obtains ZR-BIPB;
2) in the presence of an acidic catalyst, obtain ZR-BIPB with tertbutyl peroxide and two-(pseudoallyl) benzene by addition reaction;
3) in the presence of the acid acceptors such as the tertiary alcohol or alkene, by tertbutyl peroxide and α, the de-hydrogen halide of α '-dihalo diisopropylbenzene(DIPB) prepares ZR-BIPB;
4) be in the presence of metal ion catalyst, directly react to synthesize ZR-BIPB by diisopropylbenzene(DIPB) and tertbutyl peroxide.
The characteristics of the various synthetic routes of brief description.
[1] condensation reaction synthesis method
The method the method is take diisopropylbenzene(DIPB) as basic raw material, obtains 21 (2 monohydroxy sec.-propyl) benzene (DCBL) by oxygen or air automatic oxidation reaction and reduction reaction.Then in the presence of an acidic catalyst, allow DCBL and tertbutyl peroxide (TBHP) that condensation reaction occurs and generate BIPB.Different according to catalyst system therefor, the condensation reaction synthesis method can be divided into again hydrochloric acid (nitric acid) catalysis method, sulfuric acid catalysis method and anhydrous oxalic acid catalysis method.Its reaction equation is:
1) hydrochloric acid (nitric acid) catalysis method
Hydrochloric acid (nitric acid) catalysis method is that German Huels company 1979 is open in German Patent
2) sulfuric acid catalysis method
The sulfuric acid catalysis method is in selected reaction solvent, sulfuric acid with 70% is as catalyzer, under 10～25 ℃ temperature of reaction, TBHP and DCBL are carried out condensation reaction by the mol ratio of 3:1, with higher yields (78%～82c%) preparation ZR-BIPB product.
3) anhydrous oxalic acid catalysis method
The anhydrous oxalic acid catalysis method is Dutch Deventer company disclosed BIPB synthesis method in patent.According to the statement of this patent specification because TBHP and two tertiary carbons alcohol EXEBL condensation generates bimolecular water, generate dialkyl peroxide ZR-BIPB, the anhydrous oxalic acid of a molecule can with two water molecules, generation oxalic acid hydrate.Utilize this character, because the water molecules that the anhydrous oxalic acid molecule constantly generates with condensation reaction makes reaction move to the direction that generates superoxide.
The anhydrous oxalic acid method can be used as the laboratory method of synthetic a small amount of BIPB, but to carry out in this way the suitability for industrialized production of BIPB, just have following problem: (1) anhydrous oxalic acid has very strong water absorbability, and the deliquescence that absorbs water easily stores and use all inconveniences.(2) anhydrous oxalic acid large usage quantity, raw materials cost is higher.(3) anhydrous oxalic acid is one of organic acid, and is more serious to equipment corrosion.(4) recycling of anhydrous oxalic acid is very difficult.Not only absorb water with the anhydrous oxalic acid of crossing, also adsorbed simultaneously considerable superoxide, only with the benzene solvent washing, be difficult to guarantee superoxide is washed off fully.When thermal dehydration activates, the easy decomposition explosion of residual superoxide.
[2] alkene addition synthesis method
The alkene addition synthesis method of ZR-14: get di isopropenylbenzene through the high-temperature catalytic Oxidative Dehydrogenation take diisopropylbenzene(DIPB) as raw material, with hydrogen chloride gas or hydrochloric acid etc. as an acidic catalyst, under certain temperature of reaction, make TBHP and (or) di isopropenylbenzene is synthesized ZR-BIPB by addition reaction; Also can be at a small amount of α, α ' dichloro-diisopropylbenzene(DIPB) exists lower, makes TBHP and di isopropenylbenzene is reacted to make ZR-BIPB.Its reaction equation is:
This synthetic method is such as the catalysis of employing hydrogenchloride, and the TBHP's of requirement is dense, reaches more than 98%, stores for transportation and proposes very high safety requirements, and the while preparation of hydrogen chloride is having relatively high expectations to equipment also.As adopt hydrochloric acid catalysis, although not high to the concentration requirement of TBHP, the consumption of TBHP increases greatly, reaches more than the twice of theoretical consumption, and is obviously not too economical.Adopt α, the catalysis of α ' dichloro-diisopropylbenzene(DIPB), then catalyzer buying difficulty is large, and cost is high.So inapplicable suitability for industrialized production of this synthesis mode.
[3] de-hydrogen halide synthesis method
The de-hydrogen halide synthesis method is Nof Corp.'s disclosed ZR-BIPB synthetic method in United States Patent (USP).According to this patent specification statement, mostly used the strong acid as hydrochloric acid, nitric acid, sulfuric acid in the patent of synthetic ZR-BIPB in the past, these catalyzer are easy to make TBHP and ZR-14 to reduce side reaction.The synthetic of DCBL will be through the complicated operating procedure such as peroxidation, reduction and separation and purification in addition, and production cost is relatively more expensive, and no matter di isopropenylbenzene prepares by DCBL dehydration or diisopropylbenzene(DIPB) catalytic dehydrogenation, and manufacturing cost is all very high.Patented invention person claims, under reduced pressure, or in the presence of the tertiary alcohol and fatty alkene, synthesizes ZR-BIPB by 21 (alpha-halogen sec.-propyl) benzene (it is prepared through the photochemical catalysis halo by diisopropyl benzene) with the reaction of TBHP dehydrohalogenation.Its reaction equation is:
The great advantage of this synthesis method is directly to react to synthesize ZR-BIPB with diisopropylbenzene(DIPB) and TBHP, and not as other several method, will make DCBL through oxidation, reduction by diisopropylbenzene(DIPB) first, diisopropylbenzene(DIPB) is through the synthetic two bromo diisopropylbenzene(DIPB)s of bromo or diisopropylbenzene(DIPB) Oxidative Dehydrogenation di isopropenylbenzene.This synthesis method has following shortcoming: (1) TBHP consumption is too large, and every a part diisopropylbenzene(DIPB) will react with four molecule DCBL, could generate a part BIPB.(2) temperature of reaction is higher, because TBHP and BIPB are to heat-labile superoxide, high temperature of reaction can make them that the thermolysis side reaction occurs, and has safety problem.(3) reaction times oversize, only dripping TBHP will 20h, adds the reaction times that TBHP all disappears, the time of whole reaction might surpass 30h.(4) side reaction is more, and reaction yield is too low, only has 41%.Therefore this ZR-BIPB synthesis method can only as the novel method of synthetic a small amount of sample in the laboratory, not be suitable for suitability for industrialized production at present.
This synthesis method has following shortcoming: (1) is if react under reduced pressure; the a large amount of hypertoxic bromize hydrogen gas that reaction generates has very strong corrodibility to equipment and pipeline; highly acid hydrogen bromide can also make the ZR-BIPB of TBHP and generation that acid catalyzed decomposition occurs, and the generation of hydrogen bromide is unfavorable to environment protection in addition.(2) with the tertiary alcohol or olefines material as reaction solvent, reclaiming what obtain is the mixture of solvent and halohydrocarbon, is difficult to separate again reuse.(3) suitability for industrialized production of reaction raw materials 21 (alpha-brominated sec.-propyl) benzene is had any problem, and production cost is higher.(4) consumption of TBHP is too large, and reaction yield is lower.So being not suitable for project, this synthetic route adopts.
[4] metal ion catalysis synthesis method
The metal ion catalysis synthesis method is by the disclosed ZR-BIPB synthetic method of Italian company.This patented method is under certain temperature of reaction, directly take diisopropylbenzene(DIPB) and tertbutyl peroxide as raw material, at mantoquita, manganese salt or bore under the katalysis of salt, pass through radical reaction mechanism, generate Isosorbide-5-Nitrae a pair of (t-butyl peroxy sec.-propyl) benzene ZR-BIPB, reaction equation is as follows:
The great advantage of this synthesis method is directly to react to synthesize ZR-BIPB with diisopropylbenzene(DIPB) and TBHP, and not as other several method, will make DCBL through oxidation, reduction by diisopropylbenzene(DIPB) first, diisopropylbenzene(DIPB) is through the synthetic two bromo diisopropylbenzene(DIPB)s of bromo or diisopropylbenzene(DIPB) Oxidative Dehydrogenation di isopropenylbenzene.This synthesis method has following shortcoming: (1) TBHP consumption is too large, and every a part diisopropylbenzene(DIPB) will react with four molecule DCBL, could generate a part BIPB.(2) temperature of reaction is higher, because TBHP and BIPB are to heat-labile superoxide, high temperature of reaction can make them that the thermolysis side reaction occurs, and has safety problem.(3) reaction times oversize, only dripping TBHP will 20h, adds the reaction times that TBHP all disappears, the time of whole reaction might surpass 30h.(4) side reaction is more, and reaction yield is too low, only has 41%.Therefore this ZR-BIPB synthesis method can only as the novel method of synthetic a small amount of sample in the laboratory, not be suitable for suitability for industrialized production at present.
Summary of the invention
The technical problem to be solved in the present invention is, overcomes deficiency of the prior art, and the method for synthetic two (tert-butyl hydroperoxide sec.-propyl) benzene of a kind of single stage method is provided.
For realizing goal of the invention, solution of the present invention is:
The method of synthetic two (tert-butyl hydroperoxide sec.-propyl) benzene of a kind of single stage method is provided, may further comprise the steps:
(1) add successively tertbutyl peroxide, 2 isopropyl benzenes alcohol to the reaction vessel that places water-bath, and catalyst n aClO
4, then slowly add mass concentration and be 70% sulfuric acid; The control charging capacity makes tertbutyl peroxide: 2 isopropyl benzenes alcohol: sulfuric acid: the mass ratio of sodium perchlorate is 3: 2: 1: 0.12～0.17; Control bath temperature at 30～55 ℃, 30～50 minutes reaction times;
(2) according to sulfuric acid: the mass ratio of de-salted water is 7: 5 adding de-salted waters, and reaction is stopped, and then controls bath temperature at 50 ℃; Standing demix is got repeated multiple times the washing and alkali cleaning of organic phase on upper strata, and obtain the finished product after drying treatment.
Among the present invention, before reaction, use solid salt Na
2CO
3Or Na
2SO
4Tertbutyl peroxide is carried out processed.
Among the present invention, when carrying out alkali cleaning, functional quality concentration is 30% NaOH solution.
Among the present invention, in alkaline cleaning procedure, add different n-nonanoic acid and rapid stirring mixture, be used for promoting the layering of reaction system organic phase.
With respect to prior art, the invention has the beneficial effects as follows:
Reaction conditions in the synthetic method of the present invention is gentle, productive rate is higher, and product purity is more than 95%.Simultaneously, in peroxidation and tertiary butyl reaction, can realize the waste liquid beyond the target product is recycled, not only be conducive to environment protection, save simultaneously raw materials for production.
Embodiment
Implementation procedure of the present invention is:
The present invention is pure as raw material, at catalyst n aClO take tertbutyl peroxide (TBHP) and 2 isopropyl benzenes
4With react under the effect of sulfuric acid.After reaction is finished, stop reactor and stir, the product in the reactor and water are two-phase through standing separation, and following water is disposed to first sewage recovering system, and the product in the reactor is sent to washing bath.With stirring two-phase is fully mixed in washing bath, organic phase is carried out repeatedly water washing, adding alkali washed after water washing was finished, and was used for a small amount of sulfuric acid that neutralized product is carried secretly, also can add simultaneously different n-nonanoic acid as additive.After each washing, the water in the washing bath enters sewage recovering system after standing separation.After the finished product drying that washing is good is processed, beat to packaging unit with pump and directly to pack.
The used raw material of the present invention can adopt:
Tertbutyl peroxide (TBHP), reagent product, the extensive and profound in meaning scientific instrument in Ningbo company limited; 98% vitriol oil, industrial goods, rich titanium dioxide company limited is believed in Zhejiang; 2 isopropyl benzenes alcohol, reagent product, the extensive and profound in meaning scientific instrument in Ningbo company limited; Sodium hydroxide, industrial goods, worker company limited is foreignized in the Ningbo town; Laboratory apparatus: 500 there-necked flasks, electric mixer S212 type, water bath; Dropping funnel, separating funnel.
The method of synthetic two (tert-butyl hydroperoxide sec.-propyl) benzene of single stage method among the present invention may further comprise the steps:
(1) add successively tertbutyl peroxide, 2 isopropyl benzenes alcohol to the reaction vessel that places water-bath, and catalyst n aClO
4, then slowly add mass concentration and be 70% sulfuric acid; The control charging capacity makes tertbutyl peroxide: 2 isopropyl benzenes alcohol: sulfuric acid: the mass ratio of sodium perchlorate is 3: 2: 1: 0.12～0.17; Control bath temperature at 30～55 ℃, 30～50 minutes reaction times;
(2) according to sulfuric acid: the mass ratio of de-salted water is 7: 5 adding de-salted waters, and reaction is stopped, and then controls bath temperature at 50 ℃; Standing demix is got repeated multiple times the washing and alkali cleaning of organic phase on upper strata, and obtain the finished product after drying treatment.
The data of specific embodiment:
The more detailed implementation procedure of specific embodiment 3 is described below:
The amount of reactant is by TBHP: 2 isopropyl benzenes alcohol: sulfuric acid: the mass ratio of perchloric acid is 3: 2: 1: 0.15 feed intake.
1, at first injecting an amount of water in the water bath is heated to about 55 ℃ and keeps constant temperature.
1. will put with the there-necked flask of agitator and be preheated to 55 ℃ to well heater, turn on agitator adds 21gTBHP simultaneously in there-necked flask;
2. add solid salt Na
2CO
30.1g, also add Na simultaneously
2SO
41.0g, and stir fast 5～10 minutes (guarantee the abundant dissolving of salt, play the effect of dehydration), keep temperature of reaction about 55 ℃.
2, standing separation and discharge
1. stop agitator;
2. wait for 10～20 minutes after leaving standstill, observe the layering situation.
3. from TBHP, isolate Na
2SO
4The aqueous solution.
3, add diisopropylbenzene(DIPB) alcohol
1. start agitator;
2. gradually adding 2 isopropyl benzenes alcohol 14g in the reactor.
4, add NaClO
4
1. add slowly solid NaCl O
41.05g to reactor.(NaClO
4Play the effect of catalyzer).
5, add slowly H
2SO
4Solution (mass concentration is 70%)
1. connect the temperature to 55 ℃ that slightly to adjust water in the process.
2. with the H of 70% concentration
2SO
47g makes in the adding there-necked flask of drainage " progressively slow " (in case splashing) of glass stick.
3. add in the sulfuric acid process progressively adjustment bath temperature holding temperature about 55 ℃, make it reach reaction conditions sustained reaction 30 minutes or longer time.Also without overlong time (helping to improve the transformation efficiency of desired product).
6, reaction finishes
1. add de-salted water 5.0g in order to dilute sulphuric acid, make the reaction mixture stopped reaction, simultaneously bath temperature decline control remains on 55 ℃.
7, standing separation and discharge
1. stop agitator, allow mixture leave standstill 20 minutes.
2. observe the layering situation, the density ratio water of product is little, above can swimming in (oily).
3. after layering finishes, with transfer pipet the water of reactor bottom is extracted out.
8, add pure water and NaOH---30% mass ratio
1. start agitator
2. at first add pure water 3g, then residual sulphuric acid soln (will slowly add when adding alkali) in adding the NaOH---30%6g neutralise mixt, water temperature still remains on 55 ℃.
9, from there-necked flask organic phase two (tert-butyl hydroperoxide sec.-propyl) benzene and water conveying to moving the funnel at night
10, add distilled water to there-necked flask
1. adding distil water 3.0g is to there-necked flask, and complete afterwards hot water temperature remains on about 55 ℃, and temperature can not surpass more than 60 ℃.
11, add different n-nonanoic acid, and for the first time alkali cleaning
1. in reaction mixture, quantitatively add different n-nonanoic acid 0.2g, and rapid stirring reactant (purpose that adds different n-nonanoic acid is to promote the layering of mixture)
12, standing demix and discharge
1. stop agitator
2. wait for 20～30 minutes after leaving standstill, observe the layering situation, after layering finishes with transfer pipet with the waste liquid sucking-off.Water temperature keeps 55 ℃.
13, add pure water and NaOH solution (mass concentration 30%)
1. in thick product, add pure water 6g and NaOH solution (mass concentration 30%) 5.6g.
14, add different n-nonanoic acid, and for the second time alkali cleaning
1. in reaction mixture, quantitatively add different n-nonanoic acid 0.2g, and the rapid stirring several minutes.
2. stir several minutes and finish, with the Na that adds 20% concentration in the backward mixing solutions
2SO
33g solution also stirs fast.
15, standing demix and discharge
1. wait for 20～30 minutes after leaving standstill, observe the layering situation, after organic phase and water layering finish with transfer pipet with the waste liquid sucking-off.Water temperature keeps 55 ℃.
16, the pure water that adds heat
1. add pure water 5.5g in the there-necked flask and carry out final separation cleaning (to remove micro-NaOH/Sulphite and other water-soluble impurity).
17, standing separation and discharge
1. wait for 20～30 minutes after leaving standstill, observe the layering situation, after organic phase and water layering finish with transfer pipet with the waste liquid sucking-off.Water temperature keeps 55 ℃.Product moisture is controlled in 5%.
18, be transported to drying chamber from the purge tank there-necked flask and carry out drying treatment, product water content is controlled at 0.1%.
Claims (4)
1. the method for synthetic two (tert-butyl hydroperoxide sec.-propyl) benzene of single stage method is characterized in that, comprises the steps:
(1) add successively tertbutyl peroxide, 2-isopropyl benzene alcohol to the reaction vessel that places water-bath, and catalyst n aClO
4, then slowly add mass concentration and be 70% sulfuric acid; The control charging capacity makes tertbutyl peroxide: 2-isopropyl benzene alcohol: sulfuric acid: the mass ratio of sodium perchlorate is 3: 2: 1: 0.12～0.17; Control bath temperature at 30～55 ℃, 30～50 minutes reaction times;
(2) according to sulfuric acid: the mass ratio of de-salted water is 7: 5 adding de-salted waters, and reaction is stopped, and then controls bath temperature at 50 ℃; Standing demix is got repeated multiple times the washing and alkali cleaning of organic phase on upper strata, and obtain the finished product after drying treatment.
2. method according to claim 1 is characterized in that, before reaction, uses solid salt Na
2CO
3Or Na
2SO
4Tertbutyl peroxide is carried out processed.
3. method according to claim 1 is characterized in that, when carrying out alkali cleaning, functional quality concentration is 30% NaOH solution.
4. method according to claim 1 is characterized in that, adds different n-nonanoic acid and rapid stirring in alkaline cleaning procedure, to promote the layering of organic phase in the reaction system.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106588735A (en) * | 2015-10-20 | 2017-04-26 | 中国石油化工集团公司 | Bis(t-butylperoxyisopropyl)benzene production method |
| CN107556225A (en) * | 2017-10-12 | 2018-01-09 | 江苏道明化学有限公司 | One kind two（T-butylperoxyisopropyl）The production method of benzene |
| CN108929257A (en) * | 2018-05-30 | 2018-12-04 | 浙江道明化学有限公司 | A kind of chemical synthesis process of organic peroxide |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106588735A (en) * | 2015-10-20 | 2017-04-26 | 中国石油化工集团公司 | Bis(t-butylperoxyisopropyl)benzene production method |
| CN107556225A (en) * | 2017-10-12 | 2018-01-09 | 江苏道明化学有限公司 | One kind two（T-butylperoxyisopropyl）The production method of benzene |
| CN108929257A (en) * | 2018-05-30 | 2018-12-04 | 浙江道明化学有限公司 | A kind of chemical synthesis process of organic peroxide |
| 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 |
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