CN103360202A - Preparation method of hexafluorobenzene and chloropentafluorobenzene - Google Patents
Preparation method of hexafluorobenzene and chloropentafluorobenzene Download PDFInfo
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Abstract
The invention discloses a preparation method of hexafluorobenzene and chloropentafluorobenzene. The preparation method of hexafluorobenzene and chloropentafluorobenzene comprises the following steps of: (1) adding raw materials including hexafluorobenzene, active potassium fluoride and a catalyst into a reactor; (2) carrying out nitrogen displacement on the reactor and adding a solvent into the reactor; (3) heating the reactor and stopping heating after a reaction completes; (4) after cooling, switching on an air valve of the reactor, evaporating a reaction product and the solvent in the reactor, and condensing and recycling the reaction product and the solvent; (5) deacidifying the reaction product and the solvent condensed and recycled in the step (4) through an acid separator; (6) separating hexafluorobenzene and chloropentafluorobenzene from the deacidified reaction product and solvent in the step (5) through a rectifying method; and (7) after the reaction product and the solvent in the reactor are completely recycled, cooling the reactor, opening a reaction kettle, and taking out residues such as potassium chloride in the reaction kettle. The preparation method of hexafluorobenzene and chloropentafluorobenzene has the characteristics of convenience for process operation, mildness in reaction, safety and controllability, simplicity in post treatment procedure, less loss and high yield.
Description
Technical field
The present invention relates to the preparation method of a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene.
Background technology
Phenyl-hexafluoride also claims perfluor benzene, CAS:392-56-3, English name Perfluorobenzene, another name hexafluorobenzene, water white liquid, molecular formula C
6F
6, molecular weight 186.05, fusing point 3.7-4.1 ° C, boiling point 81-82 ° C, density 1.612g/cm
3, specific refractory power 1.376-1.378.
One chlorine penta fluoro benzene also claims five fluorochlorobenzenes, CAS:344-07-0, English name chloropentafluorobenzene, water white liquid, molecular formula C
6F
5Cl, molecular weight 202.50,18.1 ℃ of fusing points, boiling point 122-123 ℃, density 1.64g/cm
3, specific refractory power 1.424.
Phenyl-hexafluoride and a chlorine penta fluoro benzene can be used as the important intermediate of synthetic perfluoro aromatic compound, synthetic multiple medicine, agricultural chemicals, liquid crystal material and special copolymer etc., in the research of exploitation liquid crystal material, find in recent years, the liquid crystalline cpd that uses perfluor benzene and a chlorine penta fluoro benzene to derive has preferably performance, therefore has boundless development prospect.
Show according to present data, the study on the synthesis of phenyl-hexafluoride and a chlorine penta fluoro benzene is not yet carried out at home, do not retrieve the data of relevant this aspect, the research of phenyl-hexafluoride and chlorine penta fluoro benzene report is also few abroad, according to the present data of grasping, the synthetic route of phenyl-hexafluoride and a chlorine penta fluoro benzene mainly contains following several:
Method one: the dehydrofluorination method take benzene as raw material
1956, Godsell, Stacey and Tatlow obtained phenyl-hexafluoride by nine fluorine hexanaphthenes dehydrofluorination in alkali lye.But nine fluorine hexanaphthenes need to be by benzene vapour and CoF under 150 ° of C conditions
3Reaction prepares, and transformation efficiency is lower, has limited its application.
Method two: the high-temperature cracking method take fluorotribromomethane as raw material
Nineteen fifty-five, Desirant has reported more directly and effective means: CFBr
3, Pintsch process prepares phenyl-hexafluoride in 630～640 ℃ platinotron.
6CFBr
3——C
6F
6+9Br
2
Although this method is simple, the complicacy of radical polymerization causes also more complicated of product, and selectivity is not high, and yield is low, and raw materials cost is high, is unfavorable for suitability for industrialized production.
Method three: the direct fluorination method take Perchlorobenzene as raw material
The people such as Mcbee, Lindgren and Ligett successively use BrF
3, SbF
5, zinc powder processes Perchlorobenzene, can obtain a small amount of phenyl-hexafluoride, other by products have tetrahydrobenzene and the cyclohexadiene compound of perfluor, fluorine chlorine.Be to use Perchlorobenzene as raw material equally, Vorozhtsov, Platonov and Yakobson attempt replacing the chlorine atom with anhydrous K F and prepare phenyl-hexafluoride.Reaction is carried out in autoclave, and 450～500 ℃ of temperature are isolated C at last
6F
6(productive rate 2l%) and the complete fluorochlorobenzene (C of fluoro not
6F
5C1:20%; C
6F
4C1
2: 14%; C
6F
3C1
3: 12%).
This method operational path is short, and raw materials cost is low, but also exists yield low, and the reactor coking is serious, has limited industrialized application.
In sum, the synthetic method of existing phenyl-hexafluoride and a chlorine penta fluoro benzene exists that transformation efficiency is lower, yield is low, the reactor coking is serious, is unfavorable for the weak point of suitability for industrialized production.
Summary of the invention
The object of the invention is to that the existing transformation efficiency of synthetic method for existing phenyl-hexafluoride and a chlorine penta fluoro benzene is lower, yield is low, the reactor coking is serious, the weak point that is unfavorable for suitability for industrialized production, provide that a kind of technological operation is easy, reaction temperature and, safety is controlled, postprocessing working procedures simple, loss less, the high phenyl-hexafluoride of productive rate and the preparation method of a chlorine penta fluoro benzene.
Technical scheme of the present invention realizes in the following way: the preparation method of a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene, take Perchlorobenzene and Potassium monofluoride as raw material, under the phase-transfer catalyst effect, adopt single reaction vessel, preparation phenyl-hexafluoride and a chlorine penta fluoro benzene in solvent, the preparation method of a kind of phenyl-hexafluoride of the present invention and a chlorine penta fluoro benzene may further comprise the steps:
⑴ put into reactor with raw material Perchlorobenzene, active potassium fluoride and catalyzer;
⑵ carry out pressure testing leakage detection and nitrogen replacement to the reactor that Perchlorobenzene, active potassium fluoride and catalyzer are housed, and then adds solvent in reactor;
⑶ heat the reactor that Perchlorobenzene, active potassium fluoride, catalyzer and solvent are housed, and makes the slow increasing temperature and pressure of this reactor to temperature of reaction and reaction pressure, reacts after 24～48 hours stopped heating, cooling;
⑷ when treat below the greenhouse cooling to 300 ℃ of the reactor among the step ⑶, open the air valve of reactor, with the reaction product in the reactor and solvent steams in the lump and condensation is reclaimed;
⑸ reaction product and the solvent that reclaim condensation among the step ⑷ remove acid part by acid separator;
⑹ separate by the method for rectifying reaction product and solvent after deacidifying among the step ⑸ with the phenyl-hexafluoride in the reaction product and a chlorine penta fluoro benzene, not fluorochlorobenzene (the C of complete fluoro
6F
4C1
2C
6F
3C1
3C
6F
2C1
4, C
6FC1
5Deng) after super-dry, again add continuation use in the reactor with solvent;
⑺ after the reactant in the question response device and solvent recuperation are complete, be cooled to below 60 ℃, open reactor, take out the residues such as Repone K in the still, the preparation work of phenyl-hexafluoride and a chlorine penta fluoro benzene is finished.
In the preparation method of above-mentioned a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene, in step ⑴, the mass ratio of described Perchlorobenzene and active potassium fluoride is 1:1.2～2.5.
In the preparation method of above-mentioned a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene, in step ⑴, the mass ratio of described Perchlorobenzene and active potassium fluoride is 1:1.7～2.0.
In the preparation method of above-mentioned a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene, in step ⑴, the mass ratio of described Perchlorobenzene and catalyzer is 1:0.005～0.03.
In the preparation method of above-mentioned a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene, in step ⑴, the mass ratio of described Perchlorobenzene and catalyzer is 1:0.01～0.015.
In the preparation method of above-mentioned a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene, in step ⑴, described catalyzer adopts four (a kind of in diethylin) phosphonium bromide, bromination Shi six alkyl San Ding Ji Phosphonium, bromination hexadecane base San Yi Ji Phosphonium, the chlorination Shi six alkyl San Ding Ji Phosphonium.
In the preparation method of above-mentioned a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene, in step ⑴, described catalyzer adopts four (diethylin) phosphonium bromides.
In the preparation method of above-mentioned a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene, in step ⑵, the mass ratio of Perchlorobenzene and solvent is 1:1.
In the preparation method of above-mentioned a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene, in step ⑵, the cyanobenzene solvent that described solvent adopts drying to process, wherein, the moisture in the cyanobenzene solvent is less than 30ppm; The cyanobenzene solvent is carried out drying treatment adopts calcium chloride or molecular sieve to carry out drying treatment.
In the preparation method of above-mentioned a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene, in step ⑶, described temperature of reaction is 500～650 ℃, and described reaction pressure is 6.0～10Mpa.
In the preparation method of above-mentioned a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene, in step ⑶, described temperature of reaction is 580～630 ℃, and described reaction pressure is 8.0～9.0Mpa.
In the preparation method of above-mentioned a kind of phenyl-hexafluoride and a chlorine penta fluoro benzene, in step ⑸, described acid separator adopts the solid sodium bicarbonate acid separator.
In the preparation method of a kind of phenyl-hexafluoride of the present invention and a chlorine penta fluoro benzene, the reaction equation of fluoridizing preparation phenyl-hexafluoride and a chlorine penta fluoro benzene take Perchlorobenzene and Potassium monofluoride as the raw material high-temperature catalytic is as follows:
Also has other not fluorochlorobenzene (C of complete fluoro in the reaction product
6F
4C1
2C
6F
3C1
3C
6F
2C1
4, C
6FC1
5Deng), re-start high-temperature catalytic after fully the fluorochlorobenzene of fluoro separates with these and fluoridize and can be further converted to phenyl-hexafluoride and a chlorine penta fluoro benzene, can improve the overall yield of phenyl-hexafluoride and a chlorine penta fluoro benzene.
The present invention compares with the synthetic method of a chlorine penta fluoro benzene with existing phenyl-hexafluoride, has following characteristics:
1, avoided the coking of reaction product, the yield that has improved, the productive rate of one way can reach more than 60%, is fit to suitability for industrialized production.
2, synthesis route is short, one-step synthesis phenyl-hexafluoride and a chlorine penta fluoro benzene, and product proportion can be regulated easily, and can obtain as required dichloro-tetrafluoro benzene, and trichlorine trifluoro-benzenes etc. are the fluorochlorobenzene of complete fluoro not.
3, technological operation is easy, reaction temperature and, safety is controlled, postprocessing working procedures is simple, loss is few, productive rate is high.
4, used raw material is the general chemical product, and the prices of raw and semifnished materials are low, and the productive rate of building-up reactions is high, and production cost is lower.
Description of drawings
Fig. 1 is the preparation method's of a kind of phenyl-hexafluoride of the present invention and a chlorine penta fluoro benzene process flow diagram.
In accompanying drawing 1,1 expression reactor; 2 expression crude product condensers; 3 expression acid separators; 4 expression rectifying tower; 5 expression solvent seasoning devices; 6 expression solvent feed tanks.
Embodiment
Below by embodiment the present invention is made further and to specify, but the present invention is not limited only to these embodiment.
Embodiment 1:
In reactor, add raw material Perchlorobenzene 130g, active potassium fluoride 260g, with catalyzer four (diethylin) phosphonium bromide 1.3g, after the methylene dichloride dehydration, add dry benzene formonitrile HCN 130g, after reinforced the finishing reactor slowly is warmed up to 580 ℃, and constant temperature is after 30 hours, reaction pressure is 8.0～8.2Mpa, and stopped heating is when being cooled to 300 ℃, open air valve, reactant and solvent are steamed also condensation recovery in the lump.The productive rate data that record reaction product see Table one:
Table one:
| Embodiment | C 6F 6，％ | C 6F 5C1，％ | Other fluorochlorobenzene, % | Other high boiling material, % |
| 1 | 31.6 | 30.3 | 33.3 | 4.8 |
Other fluorochlorobenzene refers to: C
6F
4C1
2, C
6F
3C1
3, C
6F
2C1
4, C
6FC1
5Deng.
Other high boiling material refers to the product except fluorochlorobenzene, mainly comprises: C
8F
9C1, C
12F
14, C
13F
10C
12Deng.
Operation steps by example one keeps other reaction conditions constant, and controlling respectively temperature of reaction is 500 ℃, 550 ℃, 600 ℃, 650 ℃, and the productive rate data of assaying reaction product see Table two:
Table two:
| Embodiment | Temperature of reaction | C 6F 6，％ | C 6F 5C1，％ | Other fluorochlorobenzene, % | Other high boiling material, % |
| 2 | 500℃ | 14.6 | 18.4 | 63.8 | 3.2 |
| 3 | 550℃ | 28.9 | 29.8 | 37.0 | 4.3 |
| 4 | 600℃ | 33.2 | 30.1 | 31.1 | 5.6 |
| 5 | 650℃ | 34.6 | 29.7 | 25.4 | 10.3 |
Operation steps by example one keeps other reaction conditions constant, and the mass ratio of controlling respectively Perchlorobenzene and catalyzer is 1:005,1:0.015,1:0.03, and the productive rate data of assaying reaction product see Table three:
Table three:
| Embodiment | Ratio | C 6F 6，％ | C 6F 5C1，％ | Other fluorochlorobenzene, % | Other high boiling material, % |
| 6 | 1:005 | 19.8 | 21.2 | 55.7 | 3.3 |
| 7 | 1:0.015 | 33.1 | 29.3 | 32.71 | 4.9 |
| 8 | 1:0.03 | 34.8 | 28.1 | 32.0 | 5.1 |
Embodiment 9,10,11:
Operation steps by example one keeps other reaction conditions constant, and the mass ratio of controlling respectively Perchlorobenzene and Potassium monofluoride is 1:1.2,1:7,1:2.5, and the productive rate data of assaying reaction product see Table four:
Table four:
| Embodiment | Ratio | C 6F 6，％ | C 6F 5C1，％ | Other fluorochlorobenzene, % | Other high boiling material, % |
| 9 | 1:1.2 | 21.2 | 24.9 | 50.0 | 3.9 |
| 10 | 1:1.7 | 30.5 | 29.8 | 35.3 | 4.4 |
| 11 | 1:2.5 | 32.6 | 27.9 | 34.6 | 4.9 |
Embodiment 12,13:
Operation steps by example one keeps other reaction conditions constant, and controlling respectively the reaction times is 24 hours, 48 hours, and the productive rate data of assaying reaction product see Table five:
Table five:
| Embodiment | Reaction times | C 6F 6，％ | C 6F 5C1，％ | Other fluorochlorobenzene, % | Other high boiling material, % |
| 12 | 24 hours | 25.6 | 27.8 | 42.3 | 4.3 |
| 13 | 48 hours | 32.0 | 29.4 | 33.7 | 4.9 |
Embodiment 14,15,16:
Operation steps by example one keeps other reaction conditions constant, changes catalyzer into bromination Shi six alkyl San Ding Ji Phosphonium, bromination hexadecane base San Yi Ji Phosphonium, chlorination Shi six alkyl San Ding Ji Phosphonium, and the productive rate data of assaying reaction product see Table six:
Table six:
Embodiment 17:
By the operation steps of example one, keep other reaction conditions constant, will contain other fluorochlorobenzene and high boiling material and be 31.2% cyanobenzene as solvent, the productive rate data of assaying reaction product see Table seven:
Table seven:
| Embodiment | C 6F 6，％ | C 6F 5C1，％ | Other fluorochlorobenzene, % | Other high boiling material, % |
| 17 | 37.8 | 36.6 | 19.3 | 6.3 |
Claims (8)
1. the preparation method of a phenyl-hexafluoride and a chlorine penta fluoro benzene, it is characterized in that take Perchlorobenzene and Potassium monofluoride as raw material, under the phase-transfer catalyst effect, adopt single reaction vessel, preparation phenyl-hexafluoride and a chlorine penta fluoro benzene in solvent, the preparation method of this phenyl-hexafluoride and a chlorine penta fluoro benzene may further comprise the steps:
⑴ put into reactor with raw material Perchlorobenzene, active potassium fluoride and catalyzer;
⑵ carry out pressure testing leakage detection and nitrogen replacement to the reactor that Perchlorobenzene, active potassium fluoride and catalyzer are housed, and then adds solvent in reactor;
⑶ heat the reactor that Perchlorobenzene, active potassium fluoride, catalyzer and solvent are housed, and makes the slow increasing temperature and pressure of this reactor to temperature of reaction and reaction pressure, reacts after 24～48 hours stopped heating, cooling;
⑷ when treat below the greenhouse cooling to 300 ℃ of the reactor among the step ⑶, open the air valve of reactor, with the reaction product in the reactor and solvent steams in the lump and condensation is reclaimed;
⑸ reaction product and the solvent that reclaim condensation among the step ⑷ remove acid part by acid separator;
⑹ separate by the method for rectifying reaction product and solvent after deacidifying among the step ⑸ with the phenyl-hexafluoride in the reaction product and a chlorine penta fluoro benzene, not fluorochlorobenzene (the C of complete fluoro
6F
4C1
2C
6F
3C1
3C
6F
2C1
4, C
6FC1
5Deng) after super-dry, again add continuation use in the reactor with solvent;
⑺ after the reactant in the question response device and solvent recuperation are complete, be cooled to below 60 ℃, open reactor, take out the residues such as Repone K in the still, the preparation work of phenyl-hexafluoride and a chlorine penta fluoro benzene is finished.
2. the preparation method of a kind of phenyl-hexafluoride according to claim 1 and a chlorine penta fluoro benzene is characterized in that in step ⑴, and the mass ratio of described Perchlorobenzene and active potassium fluoride is 1:1.2～2.5.
3. the preparation method of a kind of phenyl-hexafluoride according to claim 1 and 2 and a chlorine penta fluoro benzene is characterized in that in step ⑴, and the mass ratio of described Perchlorobenzene and catalyzer is 1:0.005～0.03.
4. the preparation method of a kind of phenyl-hexafluoride according to claim 1 and 2 and a chlorine penta fluoro benzene, it is characterized in that in step ⑴ described catalyzer adopts four (a kind of in diethylin) phosphonium bromide, bromination Shi six alkyl San Ding Ji Phosphonium, bromination hexadecane base San Yi Ji Phosphonium, the chlorination Shi six alkyl San Ding Ji Phosphonium.
5. the preparation method of a kind of phenyl-hexafluoride according to claim 1 and 2 and a chlorine penta fluoro benzene is characterized in that in step ⑵, and the mass ratio of Perchlorobenzene and solvent is 1:1.
6. the preparation method of a kind of phenyl-hexafluoride according to claim 1 and 2 and a chlorine penta fluoro benzene is characterized in that in step ⑵, the cyanobenzene solvent that described solvent adopts drying to process, and wherein, the moisture in the cyanobenzene solvent is less than 30ppm; The cyanobenzene solvent is carried out drying treatment adopts calcium chloride or molecular sieve to carry out drying treatment.
7. the preparation method of a kind of phenyl-hexafluoride according to claim 1 and 2 and a chlorine penta fluoro benzene is characterized in that in step ⑶, and described temperature of reaction is 500～650 ℃, and described reaction pressure is 6.0～10Mpa.
8. the preparation method of a kind of phenyl-hexafluoride according to claim 1 and 2 and a chlorine penta fluoro benzene is characterized in that in step ⑸, and described acid separator adopts the solid sodium bicarbonate acid separator.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104725183A (en) * | 2015-02-16 | 2015-06-24 | 巨化集团技术中心 | Environment-friendly treatment method of hexachlorobenzene |
| CN105061260A (en) * | 2015-08-25 | 2015-11-18 | 苏州飞翔新材料研究院有限公司 | Method for preparing aromatic or pyridine meta-fluorination compound |
| CN111116306A (en) * | 2019-12-26 | 2020-05-08 | 洛阳森蓝化工材料科技有限公司 | Preparation method of hexafluorobenzene |
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| CN101168493A (en) * | 2006-10-26 | 2008-04-30 | 中国石油化工股份有限公司 | Preparation method for fluorochlorobenzene |
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2013
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| CN1238748A (en) * | 1996-11-22 | 1999-12-15 | 阿尔伯麦尔公司 | Halogen exchange reactions and uses thereof |
| US6241917B1 (en) * | 1996-11-22 | 2001-06-05 | Albemarle Corporation | Halogen exchange reactions in preparing catalysts and their precursors |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104725183A (en) * | 2015-02-16 | 2015-06-24 | 巨化集团技术中心 | Environment-friendly treatment method of hexachlorobenzene |
| CN104725183B (en) * | 2015-02-16 | 2017-12-22 | 巨化集团技术中心 | A kind of environment-friendly treatment method of hexachloro-benzene |
| CN105061260A (en) * | 2015-08-25 | 2015-11-18 | 苏州飞翔新材料研究院有限公司 | Method for preparing aromatic or pyridine meta-fluorination compound |
| CN111116306A (en) * | 2019-12-26 | 2020-05-08 | 洛阳森蓝化工材料科技有限公司 | Preparation method of hexafluorobenzene |
| CN111116306B (en) * | 2019-12-26 | 2022-09-13 | 洛阳森蓝化工材料科技有限公司 | Preparation method of hexafluorobenzene |
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Effective date of registration: 20151119 Address after: 324000 Zhejiang province Kecheng District of Quzhou City Green Road No. 18 Patentee after: Quzhou sea light Technology Co., Ltd. Address before: 324004 Zhejiang province Kecheng District of Quzhou City Green Road No. 18 Patentee before: ZHEJIANG HAILAN CHEMICAL GROUP CO., LTD. |
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Address after: 324004 Zhejiang Province, Quzhou City Kecheng District No. 16 Hua Feng Lu 1, building 3, building 4 Patentee after: Quzhou Dry Technology Co., Ltd. Address before: 324000 Zhejiang province Kecheng District of Quzhou City Green Road No. 18 Patentee before: Quzhou sea light Technology Co., Ltd. |