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Method for preparing 1,5,9-cyclododecatriene

A technology of cyclododecatriene and butadiene, which is applied in the field of 1,5,9-cyclododecatriene, can solve the problems of adverse effects on CDT yield and not given, and achieve short reaction time, Less polymerization by-products and reduced reaction costs

Inactive Publication Date: 2013-08-07
李翔 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, none of the methods described in the above-mentioned patents and documents gives the selectivity of trans,trans,cis-CDT, and among the various isomers of CDT only trans,trans,cis-CDT is of industrial importance
And the reaction by-product described in above-mentioned patent technology is as: C 8 、C 16 And the selectivity of butadiene high polymer is all very high, the yield of CDT is adversely affected as the method described in US3499049

Method used

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  • Method for preparing 1,5,9-cyclododecatriene
  • Method for preparing 1,5,9-cyclododecatriene
  • Method for preparing 1,5,9-cyclododecatriene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] The reaction was carried out in a four-stage stirred reactor cascade (20 liter volume per reactor). The reaction temperature is kept at 50±1° C. by jacket cooling, and the reactor pressure is adjusted to 0.01-0.12 mpa. The relevant parameters of the four-stage reactor are:

[0092] The pressure relationship of the cascade reaction is: P1>P2>P3>P4

[0093] The catalyst concentration relationship for the cascade reaction is: C1>C2>C3>C4

[0094] The 1,3-butadiene reaction amount relationship of the cascade reaction is: V1>V2>V3>V4

[0095] The temperature relationship of the cascade reaction is T1=T2=T3=T4

[0096] in:

[0097] The pressure of each reactor in the P-cascade reaction

[0098] C-Concentration of catalyst in each reactor in the cascade reaction

[0099] 1,3-butadiene conversion in each reactor in V-cascade reaction

[0100] The temperature of each reactor in the T-cascade reaction

[0101] And in reactor 1 an adjustment was made to obtain a water cont...

Embodiment 2

[0114] Basically the conditions described in Example 1, but adopting diethyl sulfoxide instead of dimethyl sulfoxide in Example 1, and the diethyl sulfoxide was increased to 0.8g / h, and adjusted in reactor 1 A water content of 100 ppm and a sulfur content of 120 ppm were obtained. Under static conditions, add to the reactor:

[0115]

[0116] Other operations are the same as in Example 1 and will not be described in detail.

[0117] Determination of the polymerization product obtained and other by-product types and their content, the results are:

[0118]

[0119] The composition of CDT isomers is:

[0120]

[0121]

[0122] Before refining, the results of gas chromatographic determination of the reaction product components are shown in Figure 6 . The content results of the components corresponding to the peaks were determined by the area integration method as shown in Table 6 below.

[0123] Table 6

[0124]

Embodiment 3

[0126] Conditions were essentially as described in Example 1, but CDT was used instead of toluene as solvent, dibutylsulfoxide was used instead of dimethylsulfoxide, and adjusted in Reactor 1 to obtain a water content of 120 ppm and a sulfur content of 80 ppm. Add to the reactor under static conditions:

[0127]

[0128] Other operations are the same as in Example 1 and will not be described in detail.

[0129] Determination of the polymerization product obtained and other by-product types and their content, the result:

[0130]

[0131]

[0132] The composition of CDT isomers is:

[0133]

[0134] Before refining, the results of gas chromatographic determination of the reaction product components are shown in Figure 7 . The content results of the corresponding components of each peak determined by the area integration method are shown in Table 7 below.

[0135] Table 7

[0136]

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Abstract

The invention provides a method for preparing 1,5,9-cyclododecatriene. The method comprises the steps that: in an organic solvent, a catalytic system composed of sesqui-alkyl aluminum chloride, TiX4 and at least one compound with a structure represented below is adopted, such that 1,3-butadiene is polymerized into 1,5,9-cyclododecatriene under catalysis. The X in the TiX4 is independently F, Cl, Br or I; R and R' are independently C1-C5 straight-chain alkyl or alkyl with free branched-chain. With the method provided by the invention, 1,3-butadiene is highly selectively converted into 1,5,9-cyclododecatriene, and is especially highly selectively converted into trans,trans,cis-1,5,9-cyclododecatriene. Through refining, fine 1,5,9-cyclododecatriene with purity higher than 99% can be obtained. Therefore, the method has important industrial application prospect.

Description

technical field [0001] The present invention belongs to the field of polyolefin technology. Specifically, the present invention relates to a method for preparing 1,5,9-cyclododecatriene under the conditions of a Ziegler-Natta type catalytic system and 1,5,9-cyclodecatriene prepared by the method Dodecatriene. Background technique [0002] 1,5,9-Cyclododecatriene (hereinafter also referred to as "CDT") can be used to prepare polyester, polyamide and plasticizer, and to produce polyamide synthetic fiber, cold-resistant plasticizer, artificial rubber , flavoring agent, epoxy resin crosslinking agent, spices, fire-resistant additives, etc., is an important industrial raw material. [0003] At present, some patents and documents in this field have disclosed some methods and tests for preparing CDT using 1,3-butadiene as a raw material. For example, FR-A1393071 describes a method for preparing CDT using a compound of titanium and aluminum as a catalytic system, which uses Ti(OR...

Claims

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Application Information

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IPC IPC(8): C07C13/277C07C2/46B01J31/38
Inventor 李翔李明泉
Owner 李翔
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