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Integrated process to produce 2,3,3,3-tetrafluoropropene

A technology of tetrafluoropropane and tetrafluoropropane, which is applied in the field of preparing fluorinated organic compounds and can solve the problems of low yield

Inactive Publication Date: 2009-12-09
HONEYWELL INT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process yields are relatively low and a significant portion of the organic starting material is converted to unwanted and / or insignificant by-products, including considerable amounts of carbon black which tend to deactivate the catalyst in the process

Method used

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  • Integrated process to produce 2,3,3,3-tetrafluoropropene
  • Integrated process to produce 2,3,3,3-tetrafluoropropene
  • Integrated process to produce 2,3,3,3-tetrafluoropropene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] This example illustrates the continuous gas phase fluorination reaction of step 1 1,1,2,3-tetrachloropropene (TCP)+3HF→2-chloro-3,3,3-trifluoropropene (HCFO-1233xf)+ 3HCl. The fluorination catalyst used in this experiment was fluorinated Cr 2 o 3 .

[0074] The continuous gas-phase fluorination reaction system used to study this reaction consists of N 2 , HF and organic feed system, feed evaporator, superheater, 4-inch ID Monel reactor, acid scrubber, dryer and product collection system. Charge 9415.2 grams of pretreated Cr in the reactor 2 o 3 catalyst, equal to approximately 6.5 liters of catalyst. After placing the reactor in a constant temperature sand bath, the reactor was heated to a reaction temperature of about 235 °C with N 2 Purge over the catalyst. Reactor pressure was about 3 psig. HF feed was introduced to the reactor (via evaporator and superheater), and N 2 The co-feed form is fed for 15 minutes, at which time N 2 Stream stops. The HF flow rat...

Embodiment 2

[0076] Fluorinated Cr deactivated after 650 hours run time as described in Example 1 2 o 3 The catalyst is regenerated by the following steps.

[0077] When N 2 The reactor was heated to 300°C while the flow rate was 5000cc / min. After the reactor temperature stabilized, synthetic air was introduced. The initial flow rate of air is such that with 0.5% O 2 . Gradually, increase 0.25% O 2 , the air flow increases so that O 2 The concentration is 2.0%. The reactor hot spot rose to 360°C. Then gradually increase the air flow rate, in increments of 0.5-1.0%, so that O 2 The concentration was increased to 5.0%. The reaction heater temperature was carefully adjusted to avoid overheating of the reactor by exceeding 380 °C.

[0078] When flowing 5% O 2 / N 2 At the same time, the reactor temperature was maintained at the hot spot temperature of the catalyst bed at 360-375° C. until the hot spot reached the top of the catalyst bed. Next, without changing the temperature of t...

Embodiment 3

[0081] This example illustrates the continuous gas-phase fluorination reaction of step 1 1,1,1,2,3-pentachloropropane (HCC-240db) + 3HF → 2-chloro-3,3,3-trifluoropropene (HCFO -1233xf)+4HCl. The fluorination catalyst used in this experiment was fluorinated Cr 2 o 3 .

[0082] The same continuous gas phase fluorination reaction system described in Example 1 was used in Example 3. Under the condition that the molar ratio of HF to HCC-240db is 15:1, the contact time is 15 seconds and the reaction temperature is 255°C, the reaction of HCC-240db+3HF→HCFO-1233xf+4HCl is carried out. GC analysis of the reactor effluent showed 100% conversion of HCC-240db and 98.3% selectivity to HCFO-1233xf on a molar basis. See Table 1 for details of Example 3.

[0083] Table 1

[0084] experiment # 71 HCC-240db+3HF→HCFO-1233xf+4HCl Fluorinated Cr 2 o 3 Catalyst, the molar ratio of HF to HCC-240db is 15:1, the contact time is 15 seconds, and the reaction temperature is 255°C.

[0085] ...

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Abstract

A method for preparing 2,3,3,3-tetrafluoroprop-1-ene comprising (a) providing a starting composition comprising at least one compound having a structure selected from Formulae I, II and III: CX 2 =CCl-CH 2 X (Formula I) CX 3 -CCl=CH 2 (Formula II) CX 3 -CHCl-CH 2 X (Formula III) wherein X is independently selected from F, Cl, Br, and I, provided that at least one X is not fluorine; (b) contacting said starting composition with a first fluorinating agent to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene and a first chlorine-containing byproduct; (c) contacting said first intermediate composition with a second fluorinating agent to produce a second intermediate composition comprising 2-chloro-1,1,1,2-tetrafluoropropane and a second chlorine-containing byproduct; and (d) catalytically dehydrochlorinating at least a portion of said 2-chloro-1,1,1,2-tetrafluoropropane to produce a reaction product comprising 2,3,3,3-tetrafluoroprop-1-ene.

Description

technical field [0001] This invention relates to a new process for the preparation of fluorinated organic compounds, especially fluorinated olefins. Background technique [0002] Hydrofluoroolefins (HFO), such as tetrafluoropropenes (including 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf)), are known to be effective refrigerants, fire extinguishing agents, Heat transfer media, propellants, blowing agents, blowing agents, gaseous dielectrics, sterilization vehicles, polymerization media, particle removal fluids, carrier fluids, polishing abrasives, displacement desiccants and power cycle working fluids. Unlike chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (FCs), which are both potentially harmful to the Earth's ozone layer, HFOs do not contain chlorine and are therefore not harmful to the ozone layer. In addition, HFO-1234yf is a compound with low global warming and low toxicity, thus meeting the increasingly stringent demand for automotive air-conditioning refrigeran...

Claims

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Application Information

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IPC IPC(8): C07C21/18C07C17/25
CPCY02P20/10
Inventor D·C·默克尔童雪松K·A·波克洛夫斯基S·贝克特塞维克R·C·约翰逊汪海有
Owner HONEYWELL INT INC
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