CN103232488B - A kind of trioctyl phosphine oxide compound and preparation method thereof - Google Patents

A kind of trioctyl phosphine oxide compound and preparation method thereof Download PDF

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CN103232488B
CN103232488B CN201310178158.3A CN201310178158A CN103232488B CN 103232488 B CN103232488 B CN 103232488B CN 201310178158 A CN201310178158 A CN 201310178158A CN 103232488 B CN103232488 B CN 103232488B
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phosphine oxide
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dioctyl
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多文彬
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Tianjin Kingzu Technology Co ltd
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Abstract

It is an object of the invention to provide a kind of yield height, the trioctyl phosphine oxide compound that cost is low, reaction condition is gentle and preparation method thereof.To realize above-mentioned goal of the invention, technical scheme is as follows：A kind of preparation method of trioctyl phosphine oxide, comprises the following steps：Sodium hypophosphite is passed sequentially through into octene addition, trichlorosilane reduction, bromoalkane addition and hydrolysis and prepares trioctyl phosphine oxide；Or by sodium hypophosphite by octene addition, trichlorosilane reduction, hydrolysis and again octene addition prepare trioctyl phosphine oxide；Or sodium hypophosphite is prepared into trioctyl phosphine oxide by octene addition, trichlorosilane reduction and alcoholysis.The raw material that the synthetic method of the present invention is selected is simple and easy to get, and using sodium hypophosphite and octene addition reaction, reaction condition is gentle, easily controllable, enhances the security of operation；It is higher to react yield, can reach more than 90%, and purifies conveniently, product purity is higher.

Description

A kind of trioctyl phosphine oxide compound and preparation method thereof
Technical field
The invention belongs to organic chemistry filed, and in particular to trioctyl phosphine oxide compound and preparation method thereof.
Background technology
Trioctyl phosphine oxide compound is generally used for the extraction of metallic nickel, cobalt and uranium etc..By taking uranium extraction as an example：Uranium mill The solution of processing is the weak solution that volume is big, uranium concentration is low, impurity content is high, uranium must be separated with impurity and tentatively make uranium dense Contracting, and in process for refining, processing be high concentration the uranium solution that contain, product quality requires to reach core pure.In the extraction work of uranium The organic phosphine commonly used in skill has tributyl phosphate (TBP), two-(2- ethylhexyls) phosphoric acid, trioctylamine with octyl group amine extractant Deng.
In uranium mill, the extraction of sulfuric acid system is more using Phosphorus and two kinds of extraction process (extractions of alkaline system of amine Conventional quaternary amine extraction process), such as octyl group phosphine extraction process and amine extracted technological process, the latter is in the world using more. China's application more is eluex process.The saturated resin of adsorption uranium, eluted with 1mol/L sulfuric acid, then this leacheate is entered Row extraction.Such as the extractant used in eluex process is the three pungent of 0.2mol/L two-(2- ethylhexyls) phosphoric acid -0.1mol/L Base phosphine oxide system.The saturation degree of organic phase is controlled more than 85%, after washing, is stripped with carbonic acid crystalline ammonium, it is pure can to obtain core Uranyl tricarbonate.Elution combines with extraction in this flow, reduces the liquid measure handled by extraction, and metal recovery rate is high, saves examination Agent, product purity are also high.
At present, trioctyl phosphine oxide compound has the synthetic method of several main flows：Grignard reagent method, hydrogen phosphide synthetic method and Red phosphorus
R is C2~C12 octyl group
Trioctyl phosphine oxide is prepared by grignard reaction, only product need to be can obtain by single step reaction.But many institute's weeks Know, grignard reaction operation difficulty is high, and low yield, RMgBr is to water and oxygen all extreme sensitivities.Moreover, yield is relatively low so that work The cost of industry production is too high.
R is H or C1~C10 octyl group
Prepared by 1- octenes and hydrogen phosphide, only need a step to obtain product trioctyl phosphine oxide, still, hydrogen phosphide is acute Poisonous gas, if suction can cause damage to heart, respiratory system, kidney, stomach, nervous system and liver, 9.7mg/m3It is dense above Degree, can cause to be poisoned；550~830mg/m3Dead, 2798mg/m occurs for 0.5~1.0 hour for contact3Can be lethal rapidly.And hydrogen phosphide In atmosphere can spontaneous combustion.
In addition, some other synthetic methods are gone back, such as：
R is C2~C12 octyl group.
But using iodine as reactant, cost is too high, pole is unfavorable for commercial Application.
Or these method yields are not high, or toxicity is too big, or cost is too high, does not comply with nowadays green low-carbon Requirement.Therefore, the two advantage, and the new method of discarding dross can be combined by finding one kind, undoubtedly be had great importance.
The content of the invention
It is an object of the invention to provide a kind of yield height, the trioctyl phosphine oxide compound that cost is low, reaction condition is gentle And preparation method thereof.
To realize above-mentioned goal of the invention, technical scheme is as follows：
A kind of trioctyl phosphine oxide compound, its structural formula are as follows：
Wherein R1, R2, R3 are C8 straight chains and branched octyl.
A kind of preparation method of trioctyl phosphine oxide, it is characterised in that：Comprise the following steps：
It is pungent that sodium hypophosphite is passed sequentially through into positive octene addition, trichlorosilane reduction, bromoalkane addition and hydrolysis preparation three Base phosphine oxide
Comprise the following steps that：
1) octene addition：A certain amount of sodium hypophosphite is used into appropriate acetic acid, 120 DEG C is heated to, is slowly dropped into Octene, continue to be heated to 135 DEG C, use31PNMR detects reaction end, after the completion of reaction, cooling, adds water and chloroform, liquid separation Unnecessary solvent is removed, is evaporated under reduced pressure and removes organic solvent, vacuum drying obtains white solid dioctyl phosphinic acid sodium；
2) trichlorosilane reduction：In the dioctyl phosphinic acid sodium input closed reactor that step 1 is obtained, three chloromethanes are added Alkane is dissolved in right amount, and addition trichlorosilane is appropriate, and 80 DEG C are reacted 16 hours,31PNMR detects reaction end, after the completion of reaction, decompression Organic solvent is distilled off, is dried in vacuo to obtain greenish liquid dioctyl phosphonium chloride；
3) bromoalkane addition：The dioctyl phosphonium chloride that step 2 is obtained is added in toluene, appropriate bromoalkane is added, in 100 DEG C reaction 24 hours,31PNMR detects reaction end, after the completion of reaction, is evaporated under reduced pressure and removes toluene and excessive bromoalkane, obtain brown Color liquid trioctylphosphine dihalo phosphine；
4) hydrolyze：The trioctylphosphine dihalo phosphine that step 3 obtains is dissolved in appropriate solvent D, distilled water is added, is stirred in room temperature Mix 1 hour,31PNMR detects reaction end, and after the completion of reaction, liquid separation removes water layer, is evaporated under reduced pressure and removes toluene, and it is solid to obtain white Body trioctyl phosphine oxide compound.
A kind of preparation method of trioctyl phosphine oxide, it is characterised in that：Comprise the following steps：
By sodium hypophosphite by positive octene addition, trichlorosilane reduction, hydrolysis and again octene addition prepare trioctylphosphine Phosphine oxide：
Comprise the following steps that：
1) octene addition：A certain amount of sodium hypophosphite is used into appropriate acetic acid, 120 DEG C is heated to, is slowly dropped into Octene, continue to be heated to 135 DEG C, use31PNMR detects reaction end, after the completion of reaction, cooling, adds water and chloroform, liquid separation Unnecessary solvent is removed, is evaporated under reduced pressure and removes organic solvent, vacuum drying obtains white solid dioctyl phosphinic acid sodium；
2) trichlorosilane reduction：In the dioctyl phosphinic acid sodium input closed reactor that step 1 is obtained, three chloromethanes are added Alkane is dissolved in right amount, and addition trichlorosilane is appropriate, and 80 DEG C are reacted 16 hours,31PNMR detects reaction end, after the completion of reaction, decompression Organic solvent is distilled off, is dried in vacuo to obtain greenish liquid dioctyl phosphonium chloride；
3) hydrolyze：The dioctyl phosphonium chloride that step 2 obtains is dissolved in toluene, adds distilled water hydrolysis,31PNMR detections are anti- Terminal is answered, after the completion of reaction, alkali lye liquid separation is added, removes water layer, is evaporated under reduced pressure and removes chloroform, vacuum drying obtains white Solid dioctyl phosphine oxide.
4) octene addition again：Dioctyl phosphine oxide is put into acetic acid, after being heated to 120 DEG C, is slowly dropped into positive octene, Continue to be heated to 135 DEG C to react 8 hours,31PNMR detects reaction end, after the completion of reaction, adds chloroform and distillation moisture Liquid, acetic acid is removed, be evaporated under reduced pressure and remove chloroform, be dried in vacuo to obtain white solid trioctyl phosphine oxide compound.
A kind of preparation method of trioctyl phosphine oxide, it is characterised in that：Comprise the following steps：
Sodium hypophosphite is prepared into trioctyl phosphine oxide by positive octene addition, trichlorosilane reduction and alcoholysis：
Comprise the following steps that：
1) octene addition：A certain amount of sodium hypophosphite is used into appropriate acetic acid, 120 DEG C is heated to, is slowly dropped into Octene, continue to be heated to 135 DEG C, use31PNMR detects reaction end, after the completion of reaction, cooling, adds water and chloroform, liquid separation Unnecessary solvent is removed, is evaporated under reduced pressure and removes organic solvent, vacuum drying obtains white solid dioctyl phosphinic acid sodium；
2) trichlorosilane reduction：In the dioctyl phosphinic acid sodium input closed reactor that step 1 is obtained, three chloromethanes are added Alkane is dissolved in right amount, and addition trichlorosilane is appropriate, and 80 DEG C are reacted 16 hours,31PNMR detects reaction end, after the completion of reaction, decompression Organic solvent is distilled off, is dried in vacuo to obtain greenish liquid dioctyl phosphonium chloride；
3) alcoholysis：The dioctyl phosphonium chloride that step 1 obtains is dissolved in solvent in chloroform, addition alphanol, 50 DEG C Reaction
2 hours,31PNMR detects reaction end, after the completion of reaction, adds moisture liquid, is evaporated under reduced pressure and removes solvent chloroform With
Alcohol excess, obtain white solid trioctyl phosphine oxide compound.
In above-mentioned reaction equation, n represents carbon atom number, and n=5.
The synthetic method of the trioctyl phosphine oxide compound of the present invention is to be based on following design：Using sodium hypophosphite as original Material, first by sodium hypophosphite and octene reaction generation dioctyl phosphinic acid compound, then with trichlorosilane by dioctyl phosphinic acid Compound reduction chlorination generation dioctyl chlorination phosphine compound, after obtaining dioctyl chlorination phosphine compound, has three kinds of modes to obtain Final product trioctyl phosphine oxide compound, first method, dioctyl chlorination phosphine compound and bromoalkane addition are generated Trioctylphosphine dihalo phosphine, then hydrolyzes to obtain trioctyl phosphine oxide compound, and second of thinking is by dioctyl chlorination phosphine compound Obtain trioctyl phosphine oxide compound after hydrolysis with octene addition again, Third Train of Thought is by dioctyl chlorination phosphine compound alcohol Solution, trioctyl phosphine oxide compound is obtained via rearrangement.
Described 31PNMR is composed for nuclear magnetic resonance phosphorus, and content of material is analyzed by detecting phosphorus 31.
The beneficial effects of the invention are as follows：The synthetic method of the trioctyl phosphine oxide compound of the present invention, the raw material letter of selection Singly it is easy to get, using sodium hypophosphite and octene addition reaction, other solvents etc. are also conventional chemical products, can be purchased by market It can buy；Reaction condition is gentle, easily controllable, enhances the security of operation；It is higher to react yield, can reach more than 90%, And purification is convenient, product purity is higher.
Embodiment
Embodiment 1
The synthesis of trioctyl phosphine oxide, by taking positive octene as an example, comprise the following steps：
1) octene addition：
Sodium hypophosphite 10g (0.114mol) is added in 50ml acetic acid, after being heated to 120 DEG C, is slowly dropped into 30g (0.268mol) positive octene, continue to be heated to 135 DEG C and react 4 hours, use31PNMR detects reaction end, cold after the completion of reaction But, add water and chloroform liquid separation to remove acid, be evaporated under reduced pressure (400Pa, 35 DEG C) and remove organic solvent, be dried in vacuo (120Pa, 25 DEG C) obtain white solid dioctyl phosphinic acid sodium 30.8g (0.106mol).Yield 93.2%.
2) trichlorosilane reduction
In 2g (0.007mol) the dioctyl phosphinic acid sodium input 50ml closed reactors that step 1 is obtained, 30ml is added Chloroform (water removal) makees solvent, adds 2g (0.015mol) trichlorosilane, and 80 DEG C are reacted 16 hours,31PNMR detection reactions Terminal, after the completion of reaction, it is evaporated under reduced pressure (400Pa, 35 DEG C) and removes organic solvent, vacuum drying (120Pa, 25 DEG C) obtains light green color Liquid dioctyl phosphonium chloride 1.82g (0.006mol).Yield 91.5%.
3) bromoalkane addition
2g (0.007mol) the dioctyls phosphonium chloride that step 2 is obtained is added in 20ml toluene (water removal), adds 1.5g (0.008mol) bromooctane, reacted 24 hours in 100 DEG C,31PNMR detects reaction end, after the completion of reaction, is evaporated under reduced pressure and removes The bromooctane (400Pa, 60 DEG C) of toluene (400Pa, 50 DEG C) and excess, obtains brown liquid 2.9g (0.006mol).Yield 87.8%.
4) hydrolyze：
2g (0.004mol) trioctylphosphine dihalo phosphine that step 3 is obtained is dissolved in 20ml toluene, distilled water is added, in room Temperature stirring 1 hour,31PNMR detects reaction end, after the completion of reaction, liquid separation removing water layer, vacuum distillation removing toluene (400Pa, 50 DEG C), obtain white solid trioctyl phosphine oxide 1.43g (0.0037mol).Yield 92.6%.
Embodiment 2
Difference with embodiment 2 is the later technique of step 2.
1) hydrolyze：The dioctyl phosphonium chloride 2g (0.007mol) that step 2 in embodiment 1 obtains is dissolved in 20ml chloroforms In, distilled water hydrolysis is added,31PNMR detects reaction end, after the completion of reaction, adds alkali lye liquid separation, removes water layer, is evaporated under reduced pressure Chloroform (400Pa, 35 DEG C) is removed, vacuum drying obtains white solid dioctyl phosphine oxide 1.73g (0.006mol).Yield 92.9%.
2) octene addition again：2g dioctyls phosphine oxide (0.007mol) is put into 20ml acetic acid, is heated to 120 DEG C Afterwards, 2.2 (0.020mol) g octenes are slowly dropped into, continues to be heated to 135 DEG C and reacts 8 hours,31PNMR detects reaction end, reaction After the completion of, chloroform and distilled water liquid separation are added, removes acetic acid, is evaporated under reduced pressure and removes chloroform (400Pa, 35 DEG C), very Sky dries (120Pa, 25 DEG C) and obtains white solid 2.2g (0.0057mol).Yield 81.4%.
Embodiment 3
The dioctyl phosphonium chloride 2g (0.007mol) that step 2 in embodiment 1 obtains is dissolved in 20ml chloroforms, added N-octyl alcohol 1g (0.0077mol), 50 DEG C are reacted 2 hours,31PNMR detects reaction end, after the completion of reaction, adds moisture liquid, depressurizes Chloroform (400Pa, 35 DEG C) and excessive n-octyl alcohol (400Pa, 65 DEG C) is distilled off, obtains white solid trioctyl phosphine oxide 2.57g(0.0067mol).Yield 95.1%
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all the present invention spirit and Any modification made within principle and equivalent substitution, should be included in the scope of the protection.

Claims (6)

  1. A kind of 1. preparation method of trioctyl phosphine oxide compound, it is characterised in that：Comprise the following steps：
    Sodium hypophosphite is passed sequentially through into positive octene addition, trichlorosilane reduction, bromoalkane addition and hydrolysis and prepares trioctylphosphine oxygen Change phosphine,
    N=5.
  2. A kind of 2. preparation method of trioctyl phosphine oxide compound according to claim 1, it is characterised in that：Including as follows Step：
    1) octene addition：A certain amount of sodium hypophosphite is used into appropriate acetic acid, 120 DEG C is heated to, is slowly dropped into just pungent Alkene, continue to be heated to 135 DEG C, use31PNMR detects reaction end, after the completion of reaction, cooling, adds water and chloroform, liquid separation removes Unnecessary solvent is removed, is evaporated under reduced pressure and removes organic solvent, vacuum drying obtains white solid dioctyl phosphinic acid sodium；
    2) trichlorosilane reduction：In the dioctyl phosphinic acid sodium input closed reactor that step 1 is obtained, add chloroform and fit Amount dissolving, addition trichlorosilane is appropriate, and 80 DEG C are reacted 16 hours,31PNMR detects reaction end, after the completion of reaction, is evaporated under reduced pressure Organic solvent is removed, is dried in vacuo to obtain greenish liquid dioctyl phosphonium chloride；
    3) bromoalkane addition：The dioctyl phosphonium chloride that step 2 is obtained is added in toluene, adds appropriate bromoalkane, anti-in 100 DEG C Answer 24 hours,31PNMR detects reaction end, after the completion of reaction, is evaporated under reduced pressure and removes toluene and excessive bromoalkane, obtain brown liquid Body trioctylphosphine dihalo phosphine；
    4) hydrolyze：The trioctylphosphine dihalo phosphine that step 3 obtains is dissolved in q. s. toluene, distilled water is added, it is small to be stirred at room temperature 1 When,31PNMR detects reaction end, and after the completion of reaction, liquid separation removes water layer, is evaporated under reduced pressure and removes toluene, obtains white solid three Octyl group phosphine oxide compound.
  3. A kind of 3. preparation method of trioctyl phosphine oxide compound, it is characterised in that：Comprise the following steps：
    By sodium hypophosphite is by positive octene addition, trichlorosilane reduction, hydrolysis and octene addition preparation trioctylphosphine aoxidizes again Phosphine：
    N=5.
  4. A kind of 4. preparation method of trioctyl phosphine oxide compound according to claim 3, it is characterised in that：Including as follows Step：
    1) octene addition：A certain amount of sodium hypophosphite is used into appropriate acetic acid, 120 DEG C is heated to, is slowly dropped into just pungent Alkene, continue to be heated to 135 DEG C, use31PNMR detects reaction end, after the completion of reaction, cooling, adds water and chloroform, liquid separation removes Unnecessary solvent is removed, is evaporated under reduced pressure and removes organic solvent, vacuum drying obtains white solid dioctyl phosphinic acid sodium；
    2) trichlorosilane reduction：In the dioctyl phosphinic acid sodium input closed reactor that step 1 is obtained, add chloroform and fit Amount dissolving, addition trichlorosilane is appropriate, and 80 DEG C are reacted 16 hours,31PNMR detects reaction end, after the completion of reaction, is evaporated under reduced pressure Organic solvent is removed, is dried in vacuo to obtain greenish liquid dioctyl phosphonium chloride；
    3) hydrolyze：The dioctyl phosphonium chloride that step 2 obtains is dissolved in toluene, adds distilled water hydrolysis,31PNMR detections reaction is eventually Point, after the completion of reaction, alkali lye liquid separation is added, removes water layer, be evaporated under reduced pressure and remove chloroform, vacuum drying obtains white solid Dioctyl phosphine oxide；
    4) octene addition again：Dioctyl phosphine oxide is put into acetic acid, after being heated to 120 DEG C, is slowly dropped into positive octene, is continued 135 DEG C are heated to react 8 hours,31PNMR detects reaction end, after the completion of reaction, adds chloroform and distilled water liquid separation, removes Acetic acid is removed, is evaporated under reduced pressure and removes chloroform, be dried in vacuo to obtain white solid trioctyl phosphine oxide compound.
  5. A kind of 5. preparation method of trioctyl phosphine oxide compound, it is characterised in that：Comprise the following steps：
    Sodium hypophosphite is prepared into trioctyl phosphine oxide by positive octene addition, trichlorosilane reduction and alcoholysis：
    N=5.
  6. A kind of 6. preparation method of trioctyl phosphine oxide compound according to claim 5, it is characterised in that：Including as follows Step：
    1) octene addition：A certain amount of sodium hypophosphite is used into appropriate acetic acid, 120 DEG C is heated to, is slowly dropped into just pungent Alkene, continue to be heated to 135 DEG C, use31PNMR detects reaction end, after the completion of reaction, cooling, adds water and chloroform, liquid separation removes Unnecessary solvent is removed, is evaporated under reduced pressure and removes organic solvent, vacuum drying obtains white solid dioctyl phosphinic acid sodium；
    2) trichlorosilane reduction：In the dioctyl phosphinic acid sodium input closed reactor that step 1 is obtained, add chloroform and fit Amount dissolving, addition trichlorosilane is appropriate, and 80 DEG C are reacted 16 hours,31PNMR detects reaction end, after the completion of reaction, is evaporated under reduced pressure Organic solvent is removed, is dried in vacuo to obtain greenish liquid dioctyl phosphonium chloride；
    3) alcoholysis：The dioctyl phosphonium chloride that step 1 obtains is dissolved in solvent in chloroform, adds alphanol, 50 DEG C of reactions 2 Hour,31PNMR detects reaction end, after the completion of reaction, adds moisture liquid, is evaporated under reduced pressure and removes solvent chloroform and alcohol excess, Obtain white solid trioctyl phosphine oxide compound.
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Citations (2)

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Publication number Priority date Publication date Assignee Title
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Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5284555A (en) * 1991-08-15 1994-02-08 Albright & Wilson Limited Process for preparing organophosphines
CN102180903A (en) * 2011-03-10 2011-09-14 常熟新特化工有限公司 Preparation method for tri-n-octyl phosphine oxide

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