CN105237331B - The method simultaneously preparing trichlorine five fluorine cyclopentenes isomerss - Google Patents
The method simultaneously preparing trichlorine five fluorine cyclopentenes isomerss Download PDFInfo
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- CN105237331B CN105237331B CN201510689893.XA CN201510689893A CN105237331B CN 105237331 B CN105237331 B CN 105237331B CN 201510689893 A CN201510689893 A CN 201510689893A CN 105237331 B CN105237331 B CN 105237331B
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Abstract
The present invention relates to the method preparing trichlorine five fluorine cyclopentenes isomerss simultaneously, belong to the field of chemical synthesis.The method have solvent or solvent-free under the conditions of, with 1,3 dichloro hexafluoro cyclopentenes, 1,4 dichloro hexafluoro cyclopentenes, 3 chlorine seven fluorine cyclopentenes or 4 chlorine seven fluorine cyclopentenes are raw material, are 30～150 DEG C with chlorination reagent in reaction temperature, occur chlorine fluorine exchange reaction that trichlorine five fluorine cyclopentenes isomerss 1 are obtained, 2,4 trichlorine five fluorine cyclopentenes, 1,2,3 trichlorine five fluorine cyclopentenes, 1,3,3 trichlorine five fluorine cyclopentenes, Isosorbide-5-Nitrae, 4 trichlorine five fluorine cyclopentenes.The inventive method not only can coproduction trichlorine five fluorine cyclopentenes isomerss, and material toxicity is less, reaction condition gentle, reaction is easily controlled, the yield of isomerss is higher, industrially can be effectively separated by common refined means.
Description
Technical field
The present invention relates to one kind prepare simultaneously 1,2,4- trichlorine five fluorine cyclopentenes, 1,2,3- trichlorine five fluorine cyclopentenes, 1,3,
3- trichlorine five fluorine cyclopentenes, Isosorbide-5-Nitrae, the method for 4- trichlorine five fluorine cyclopentenes, more particularly, to one kind pass through 1,3- dichloro hexafluoro ring penta
Alkene or 1,4- dichloro hexafluoro cyclopentenes are reacted with anhydrous Aluminum chloride and obtain 1,2,4- trichlorine five fluorine cyclopentenes, 1,2,3- trichlorine five fluorine
Cyclopentenes, 1,3,3- trichlorine five fluorine cyclopentenes, the preparation method of 1,4,4- trichlorine five fluorine cyclopentenes.
Background technology
Trichlorine five fluorine cyclopentenes isomerss are the particularly important industrial chemicals of a class or intermediate, can synthesize etching
Agent octafluoro cyclopentenes, intermediate 1- chlorine seven fluorine cyclopentenes of abluent 1,1,2,2,3,3,4- seven fluorine Pentamethylene. etc..According to Gauss
Calculate, trichlorine five fluorine cyclopentenes isomerss 1,2,4- trichlorine five fluorine cyclopentenes, 1,2,3- trichlorine five fluorine cyclopentenes, 1,3,3-
Trichlorine five fluorine cyclopentenes, Isosorbide-5-Nitrae, 4- trichlorine five fluorine cyclopentenes, due to the difference in structure, lead to its compound capacity volume variance very big,
In some exchange chloride for fluoride, using compound energy of a relatively high isomerss 1,3,3- trichlorine five fluorine cyclopentenes,
The relatively low isomerss 1,2,3- trichlorine five fluorine cyclopentenes of 1,4,4- trichlorine five fluorine cyclopentenes alternative compounds energy or
1,2,4- trichlorine five fluorine cyclopentenes, can obtain structure identical target product under the reaction condition of milder, and its product
Rate is higher.Therefore, 1,2,4- trichlorine five fluorine cyclopentenes, 1,2,3- trichlorine five fluorine cyclopentenes, 1,3,3- trichlorine five fluorine cyclopentenes, 1,
The research of 4,4- trichlorine five fluorine cyclopentenes has important theory significance and using value.
Trichlorine five fluorine cyclopentenes isomerss more typically are 1,2,3- trichlorine five fluorine cyclopentenes, a lot of document reports
The preparation method of 1,2,3- trichlorine five fluorine cyclopentenes.US6218586 reports in the presence of fluorination catalyst, hexacholorocyclopentadiene
With chlorine, anhydrous hydrogen fluoride reaction, obtain 1,2,3- trichlorine five fluorine cyclopentenes, its yield is 19.2%.Urged by changing fluorination
Agent, can prepare 1,2,4- trichlorine five fluorine cyclopentenes under similar conditions.US5180861 reports containing magnesium, bismuth, ferrum
Fluorination catalyst catalysis hexacholorocyclopentadiene and chlorine, anhydrous hydrogen fluoride reaction obtain 1,2,4- trichlorine five fluorine cyclopentenes, its
Yield is 29.1%.However, the method preparing trichlorine five fluorine cyclopentenes isomerss is rarely reported simultaneously.Document
[ChemischeBerichte；vol.117；nb.3；(1984)；P.1153-1160] report by 1,2,3,4,5- pentachloro- five fluorine
Pentamethylene. is raw material, and Na-Ag-Hg alloy reaction, obtain three kinds of isomerss (3S, 4s, 5R) of trichlorine five fluorine cyclopentenes-
3,4,5- trichlorine five fluorine cyclopentenes, (3S, 4r, 5R) -3,4,5- trichlorine five fluorine cyclopentenes, (3R, 5R) -3,4,5- trichlorine five fluorine ring
Amylene, the gross production rate of three is 8%.Document [J.Gen.Chem.USSR (Engl.Transl.)；vol.59；nb.3.2；
(1989)；P.622-630,551-558] report by chloro- 2, the 5- difluorocyclohex alkane of Isosorbide-5-Nitrae-two be raw material, 600 DEG C of reaction temperature,
3.8 seconds times of contact, pyrolysis is occurred to obtain three kinds of isomerss (3S, 4s, 5R) -3 of trichlorine five fluorine cyclopentenes, 4,5- trichlorines
Five fluorine cyclopentenes, (3S, 4r, 5R) -3,4,5- trichlorine five fluorine cyclopentenes, (3R, 5R) -3,4,5- trichlorine five fluorine cyclopentenes, three
Gross production rate be 8.7%.
Above-mentioned technology has the following disadvantages：First, be mostly same point of the single kind preparing trichlorine five fluorine cyclopentenes different
Structure body；Secondly, the technology simultaneously preparing trichlorine five fluorine cyclopentenes isomerss is too harsh, employ wayward, have play
The Na-Ag-Hg alloy of poison or (600 DEG C) pyrolysis of high temperature.Industrially, this kind of isomer is difficult to by efficiently separating.
Content of the invention
The present invention is directed to the deficiency in background technology, and not only material toxicity is low, reaction condition gentle, easily control to provide one kind
System, prepare the isomerss of trichlorine five fluorine cyclopentenes simultaneously, and yield is higher, be industrially easy to be effectively separated.
The method simultaneously preparing trichlorine five fluorine cyclopentenes isomerss, described trichlorine five fluorine cyclopentenes isomerss are
1,2,4- trichlorine five fluorine cyclopentenes, 1,2,3- trichlorine five fluorine cyclopentenes, 1,3,3- trichlorine five fluorine cyclopentenes, 1,4,4- trichlorine five fluorine
Cyclopentenes it is characterised in that：Under organic solvent or condition of no solvent, with 1,3- dichloro hexafluoro cyclopentenes, Isosorbide-5-Nitrae-dichloro hexafluoro
Cyclopentenes, 3- chlorine seven fluorine cyclopentenes or 4- chlorine seven fluorine cyclopentenes be raw material, with chlorination reagent reaction temperature be 30～150 DEG C of bars
Chlorine-fluorine exchange reaction is occurred to be obtained under part.
Described chlorination reagent is anhydrous Aluminum chloride, butter of tin, Antimony pentachloride, titanium tetrachloride, phosphorus pentachloride or tri-chlorination
Phosphorus.
Described reaction in organic solvent be dimethylformamide, dimethyl sulfoxide, sulfolane, carbon tetrachloride, 1,1,1,3,
3- pentachloropropane, ethanol, 1- n-butyl alcohol.
In described reaction chlorination reagent, solvent and 1,3- dichloro hexafluoro cyclopentenes or 1,4- dichloro hexafluoro cyclopentenes mole
Than for 0.1～1：0～20：1, in described reaction, the response time is 2～30 hours.
Preferably 0.3～0.5：0：1 or 0.3～0.5：10～16：1, in described reaction, reaction temperature is 80～120 DEG C, excellent
Select 7～20 hours.
The condition of described reaction is：Anhydrous Aluminum chloride, dimethylformamide or 1,1,1,3,3- pentachloropropane and 1,3- bis-
The mol ratio of chlorine hexafluoro cyclopentenes or 1,4- dichloro hexafluoro cyclopentenes is 0.1～1：0～20：1, reaction temperature is 30～150 DEG C,
Response time is 2～30 hours.
The condition of described reaction is：Anhydrous Aluminum chloride and 1,3- dichloro hexafluoro cyclopentenes or 1,4- dichloro hexafluoro cyclopentenes
Mol ratio is 0.3～0.5：1, reaction temperature is 80～120 DEG C, and the response time is 7～20 hours.
The condition of described reaction is：Anhydrous Aluminum chloride, dimethylformamide or 1,1,1,3,3- pentachloropropane and 1,3- bis-
The mol ratio of chlorine hexafluoro cyclopentenes or 1,4- dichloro hexafluoro cyclopentenes is 0.3～0.5：10～16：1, reaction temperature is 80～120
DEG C, the response time is 7～20 hours.
The present invention, is handed over through liquid phase chlorine-fluorine for raw material with 1,3- dichloro hexafluoro cyclopentenes or Isosorbide-5-Nitrae-dichloro hexafluoro cyclopentenes
Change reaction, obtain 1,2,4- trichlorine five fluorine cyclopentenes, 1,2,3- trichlorine five fluorine cyclopentenes, 1,3,3- trichlorine five fluorine cyclopentenes simultaneously
With 1,4,4- trichlorine five fluorine cyclopentenes.Its dominant response is as follows：
The present invention can be carried out at ambient pressure, also can carry out under high pressure.Due to being liquid phase reactor, be not related to phase feed or
Product, therefore, pressure is on reaction impact according to the present invention less.
The present invention can be carried out in the reactor of glass material, stainless steel or politef material.
The invention provides a kind of can be with the preparation method of the isomerss of coproduction trichlorine five fluorine cyclopentenes, wherein trichlorine
Five fluorine cyclopentenes isomerss include 1,2,4- trichlorine five fluorine cyclopentenes, 1,2,3- trichlorine five fluorine cyclopentenes, 1,3,3- trichlorine
Five fluorine cyclopentenes and 1,4,4- trichlorine five fluorine cyclopentenes.Only need respectively to 1,2,4- trichlorine five fluorine cyclopentenes, 1,2,3- trichlorine five
The products such as fluorine cyclopentenes, 1,3,3- trichlorine five fluorine cyclopentenes, 1,4,4- trichlorine five fluorine cyclopentenes carry out except solvent, eliminating water, refine
Deng post processing, you can obtain corresponding product.Isosorbide-5-Nitrae, 4- trichlorine five fluorine cyclopentenes boiling point is 109-113 DEG C (760mmHg), 1,3,3-
Trichlorine five fluorine cyclopentenes boiling point is 115-117 DEG C (760mmHg), and 1,2,4- trichlorine five fluorine cyclopentenes boiling point is 123-124 DEG C
(760mmHg), 1,2,3- trichlorine five fluorine cyclopentenes boiling point is 129-130 DEG C (760mmHg).
Advantages of the present invention：The present invention provide technical method not only can coproduction trichlorine five fluorine cyclopentenes isomerss 1,
2,4- trichlorine five fluorine cyclopentenes, 1,2,3- trichlorine five fluorine cyclopentenes, 1,3,3- trichlorine five fluorine cyclopentenes and 1,4,4- trichlorine five fluorine
Cyclopentenes, and material toxicity is less, reaction condition is gentle, reaction is easily controlled, the yield of isomerss is higher, in industry
On can be effectively separated by common refined means.
Specific embodiment
Analytical tool：Glad chromatograph GC-930 in Shanghai sea, hydrogen flame detector, chromatographic column is capillary column Al2O3/S“50m×
0.320mm × 0.25 μm " (manufacture of chromatographic technique research and development centre of Lanzhou Inst. of Chemical Physics, Chinese Academy of Sciences).
Gas chromatography analysis method：Product, after washing, alkali cleaning and being dried, takes gaseous sample to carry out gas chromatogram and divides
Analysis.High Purity Nitrogen and hydrogen are used as carrier gas.Testing conditions are 250 DEG C of temperature of vaporization chamber, 250 DEG C of auxiliary furnace 2 temperature, detector temperature
250 DEG C, 40 DEG C of post stove initial temperature, keep 10 minutes, 15 DEG C/min of heating rate, 230 DEG C of final temperature, keep 3 minutes.
Following the present invention is described in further detail in conjunction with the embodiments, but do not limit the scope of the invention.
Embodiment 1
Normal pressure, under stirring condition, burns in 250 milliliters of glass equipped with condensing tube and bubbler (making reaction be in normal pressure)
In bottle, add anhydrous Aluminum chloride, dimethylformamide and Isosorbide-5-Nitrae-dichloro hexafluoro cyclopentenes, its molar ratio anhydrous Aluminum chloride/bis-
Methylformamide/Isosorbide-5-Nitrae-dichloro hexafluoro cyclopentenes are 0.5/10/1,110 DEG C of reaction temperature, 14 hours response time.Reaction terminates
Afterwards, through washing 100ml × 3 time, anhydrous magnesium sulfate 2.0g is dried, and is filtrated to get organic faciess, takes organic faciess to carry out gas chromatogram and divide
The composition of analysis Organic substance, the results are shown in Table 1.
Above-mentioned organic faciess are carried out rectification, obtains isomerss 1,2, the 4- trichlorine five fluorine ring penta of trichlorine five fluorine cyclopentenes
Alkene, 1,2,3- trichlorine five fluorine cyclopentenes, 1,3,3- trichlorine five fluorine cyclopentenes and 1,4,4- trichlorine five fluorine cyclopentenes.Wherein, Isosorbide-5-Nitrae,
4- trichlorine five fluorine cyclopentenes boiling point is 109-113 DEG C (760mmHg), and 1,3,3- trichlorine five fluorine cyclopentenes boiling point is 115-117 DEG C
(760mmHg), 1,2,4- trichlorine five fluorine cyclopentenes boiling point is 123-124 DEG C (760mmHg), and 1,2,3- trichlorine five fluorine cyclopentenes boil
Point is 129-130 DEG C (760mmHg).
Embodiment 2
Operation same as Example 1, except that anhydrous Aluminum chloride/dimethylformamide/Isosorbide-5-Nitrae-dichloro hexafluoro ring
The molar ratio of amylene is 0.1/20/1, the results are shown in Table 1.
Embodiment 3
Operation same as Example 1, except that anhydrous Aluminum chloride/dimethylformamide/Isosorbide-5-Nitrae-dichloro hexafluoro ring
The molar ratio of amylene is 0.3/16/1, the results are shown in Table 1.
Embodiment 4
Operation same as Example 1, except that anhydrous Aluminum chloride/dimethylformamide/Isosorbide-5-Nitrae-dichloro hexafluoro ring
The molar ratio of amylene is 0.7/5/1, the results are shown in Table 1.
Embodiment 5
Operation same as Example 1, except that anhydrous Aluminum chloride/dimethylformamide/Isosorbide-5-Nitrae-dichloro hexafluoro ring
The molar ratio of amylene is 1/0/1, the results are shown in Table 1.
Embodiment 6
Operation same as Example 1, except that anhydrous Aluminum chloride/dimethylformamide/Isosorbide-5-Nitrae-dichloro hexafluoro ring
The molar ratio of amylene is 0.1/0/1, the results are shown in Table 1.
Embodiment 7
Operation same as Example 1, except that anhydrous Aluminum chloride/dimethylformamide/Isosorbide-5-Nitrae-dichloro hexafluoro ring
The molar ratio of amylene is 0.3/0/1, the results are shown in Table 1.
Embodiment 8
Operation same as Example 1, except that anhydrous Aluminum chloride/dimethylformamide/Isosorbide-5-Nitrae-dichloro hexafluoro ring
The molar ratio of amylene is 0.5/0/1, the results are shown in Table 1.
Embodiment 9
Operation same as Example 1, except that 30 DEG C of reaction temperature, in 30 hours response time, the results are shown in Table 1.
Embodiment 10
Operation same as Example 1, except that 50 DEG C of reaction temperature, in 25 hours response time, the results are shown in Table 1.
Embodiment 11
Operation same as Example 1, except that 70 DEG C of reaction temperature, in 20 hours response time, the results are shown in Table 1.
Embodiment 12
Operation same as Example 1, except that 90 DEG C of reaction temperature, in 17 hours response time, the results are shown in Table 1.
Embodiment 13
Operation same as Example 1, except that 130 DEG C of reaction temperature, in 8 hours response time, the results are shown in Table 1.
Embodiment 14
Operation same as Example 1, except that 150 DEG C of reaction temperature, in 2 hours response time, the results are shown in Table 1.
Embodiment 15
Operation same as Example 1, except that Isosorbide-5-Nitrae-dichloro hexafluoro cyclopentenes such as are changed at the 1,3- of the amount of material
Dichloro hexafluoro cyclopentenes, the results are shown in Table 1.
Embodiment 16
Operation same as Example 1, except that Isosorbide-5-Nitrae-dichloro hexafluoro cyclopentenes such as are changed at the 3- chlorine of the amount of material
Seven fluorine cyclopentenes, the results are shown in Table 2.
Embodiment 17
Operation same as Example 1, except that Isosorbide-5-Nitrae-dichloro hexafluoro cyclopentenes such as are changed at the 4- chlorine of the amount of material
Seven fluorine cyclopentenes, the results are shown in Table 2.
Embodiment 18
Operation same as Example 1, except that anhydrous Aluminum chloride such as changes at the butter of tin of the amount of material, the result
It is shown in Table 1.
Embodiment 19
Operation same as Example 1, except that anhydrous Aluminum chloride such as changes at the Antimony pentachloride of the amount of material, the result
It is shown in Table 1.
Embodiment 20
Operation same as Example 1, except that anhydrous Aluminum chloride such as changes at the titanium tetrachloride of the amount of material, the result
It is shown in Table 1.
Embodiment 21
Operation same as Example 1, except that anhydrous Aluminum chloride such as changes at the phosphorus pentachloride of the amount of material, the result
It is shown in Table 1.
Embodiment 22
Operation same as Example 1, except that anhydrous Aluminum chloride such as changes at the Phosphorous chloride. of the amount of material, the result
It is shown in Table 1.
Embodiment 23
Operation same as Example 1, except that dimethylformamide such as changes at the dimethyl sulfoxide of the amount of material,
The results are shown in Table 1.
Embodiment 24
Operation same as Example 1, except that dimethylformamide such as changes at the sulfolane of the amount of material, the result
It is shown in Table 1.
Embodiment 25
Normal pressure, under stirring condition, burns in 250 milliliters of glass equipped with condensing tube and bubbler (making reaction be in normal pressure)
In bottle, add anhydrous Aluminum chloride, carbon tetrachloride and 1,3- dichloro hexafluoro cyclopentenes, its molar ratio anhydrous Aluminum chloride/dimethyl
Methanamide/1,3- dichloro hexafluoro cyclopentenes are 0.3/10/1,70 DEG C of reaction temperature, 6 hours response time.After reaction terminates, warp
Washing 100ml × 3 time, anhydrous magnesium sulfate 2.0g is dried, is filtrated to get organic faciess, takes organic faciess to carry out gas chromatographic analysiss organic
The composition of thing, the results are shown in Table 1.
Embodiment 26
With the operation of embodiment 25 identical, except that carbon tetrachloride such as changes at 1,1,1,3, the 3- pentachloro- of the amount of material
Propane, the results are shown in Table 1.
Embodiment 27
With the operation of embodiment 25 identical, except that carbon tetrachloride such as changes at the ethanol of the amount of material, the results are shown in Table
1.
Embodiment 28
With the operation of embodiment 25 identical, except that carbon tetrachloride such as changes at the 1- n-butyl alcohol of the amount of material, the result
It is shown in Table 1.
Table 1
Note：(1) used in embodiment " 1-14 " and embodiment " 18-24 ", raw material is 1,4- dichloro hexafluoro cyclopentenes.
(2) used in embodiment " 15 " and embodiment " 25-28 ", raw material is 1,3- dichloro hexafluoro cyclopentenes.
Table 2
Note：(1) used in embodiment " 16 ", raw material is 3- chlorine seven fluorine cyclopentenes.
(2) used in embodiment " 17 ", raw material is 4- chlorine seven fluorine cyclopentenes.
Claims (7)
1. the method simultaneously preparing trichlorine five fluorine cyclopentenes isomerss, described trichlorine five fluorine cyclopentenes isomerss are 1,
2,4- trichlorine five fluorine cyclopentenes, 1,2,3- trichlorine five fluorine cyclopentenes, 1,3,3- trichlorine five fluorine cyclopentenes, 1,4,4- trichlorine five fluorine ring
Amylene it is characterised in that：Under organic solvent or condition of no solvent, with 1,3- dichloro hexafluoro cyclopentenes, Isosorbide-5-Nitrae-dichloro hexafluoro ring
Amylene, 3- chlorine seven fluorine cyclopentenes or 4- chlorine seven fluorine cyclopentenes are raw material, are 30～150 DEG C with chlorination reagent in reaction temperature, send out
Raw chlorine-fluorine exchange reaction and be obtained, described chlorination reagent is anhydrous Aluminum chloride, butter of tin, Antimony pentachloride, titanium tetrachloride, five
Phosphorus chloride or Phosphorous chloride..
2. method according to claim 1, in described reaction, organic solvent is dimethylformamide, dimethyl sulfoxide, ring
Fourth sulfone, carbon tetrachloride, 1,1,1,3,3- pentachloropropane, ethanol, 1- n-butyl alcohol.
3. method according to claim 2, chlorination reagent, solvent and 1,3- dichloro hexafluoro cyclopentenes or 1 in described reaction,
The mol ratio of 4- dichloro hexafluoro cyclopentenes is 0.1～1：0～20：1, in described reaction, the response time is 2～30 hours.
4. method according to claim 3, chlorination reagent, solvent and 1,3- dichloro hexafluoro cyclopentenes or Isosorbide-5-Nitrae-two in reaction
The mol ratio of chlorine hexafluoro cyclopentenes is 0.3～0.5：0：1 or 0.3～0.5：10～16：1, in described reaction, reaction temperature is 80
～120 DEG C, the response time is 7～20 hours.
5. method according to claim 2, the condition of described reaction is：Anhydrous Aluminum chloride, dimethylformamide or 1,1,
1,3,3- pentachloropropane is 0.1～1 with the mol ratio of 1,3- dichloro hexafluoro cyclopentenes or Isosorbide-5-Nitrae-dichloro hexafluoro cyclopentenes：0～20：
1, reaction temperature is 30～150 DEG C, and the response time is 2～30 hours.
6. method according to claim 2, the condition of described reaction is：Anhydrous Aluminum chloride and 1,3- dichloro hexafluoro cyclopentenes
Or the mol ratio of 1,4- dichloro hexafluoro cyclopentenes is 0.3～0.5：1, reaction temperature is 80～120 DEG C, and the response time is 7～20
Hour.
7. method according to claim 2, the condition of described reaction is：Anhydrous Aluminum chloride, dimethylformamide or 1,1,
1,3,3- pentachloropropane is 0.3～0.5 with the mol ratio of 1,3- dichloro hexafluoro cyclopentenes or Isosorbide-5-Nitrae-dichloro hexafluoro cyclopentenes：10～
16：1, reaction temperature is 80～120 DEG C, and the response time is 7～20 hours.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0999195A1 (en) * | 1998-11-05 | 2000-05-10 | Central Glass Company, Limited | Method for preparing perhalogenated five-membered cyclic compound |
| CN1270575A (en) * | 1997-09-17 | 2000-10-18 | 森陶硝子株式会社 | Method for producing perhalogenated cyclopentene |
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2015
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1270575A (en) * | 1997-09-17 | 2000-10-18 | 森陶硝子株式会社 | Method for producing perhalogenated cyclopentene |
| EP0999195A1 (en) * | 1998-11-05 | 2000-05-10 | Central Glass Company, Limited | Method for preparing perhalogenated five-membered cyclic compound |
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| C06 | Publication | ||
| PB01 | Publication | ||
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