CN105153224B - Synthesizing method of 1-octylphosphonate for metal corrosion inhibition - Google Patents
Synthesizing method of 1-octylphosphonate for metal corrosion inhibition Download PDFInfo
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- CN105153224B CN105153224B CN201510604364.5A CN201510604364A CN105153224B CN 105153224 B CN105153224 B CN 105153224B CN 201510604364 A CN201510604364 A CN 201510604364A CN 105153224 B CN105153224 B CN 105153224B
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Abstract
The invention discloses a synthesizing method of 1-octylphosphonate for metal corrosion inhibition and belongs to the field of chemical preparation. The method includes the synthesizing methods that firstly, 1-bromoctane and catalysts are mixed in proportion, triethyl phosphate is dropwise added into a reaction system within the temperature range of 70-120 DEG C, and adding time is 2-3h; then the temperature of the system is raised to 130-160 DEG C and preserved for 2-4 h, and then the reaction continues; secondly, the temperature of the system is lowered to 60-80 DEG C, a hydrogen bromide aqueous solution is dropwise added, and the adding time is 0.5-1 h; then temperature is raised till backflow happens, and the temperature is preserved for 2-4 h for carrying out a reaction; thirdly, the hydrogen bromide aqueous solution in the reaction system is firstly evaporated out at normal pressure, and then vacuumizing is performed so that excessive 1-bromoctane in the reaction can be evaporated out; fourthly, cooling is performed after distilling ends, extraction and liquid separation are performed, and then the 1-octylphosphonate can be prepared. According to the synthesizing method, reaction conditions are moderate, the reaction process is easy to control, the product yield is high, and purity is high.
Description
Technical field
A kind of the present invention relates to chemicals preparing technical field, more particularly, it relates to 1- octyl group for corrosion inhibition for metal
The synthetic method of phosphonic acids.
Background technology
Metal working lubricant liquid refer to for metal and its alloy cutting, grinding, punching press, rolling and drawing etc. various plus
The lubricant that work process is used, main inclusion metal cutting lubricant, plastic working lubricant and anti-rust and lubrication grease etc..Greatly
Most metal working lubricants has following effect：Control friction, reduce abrasion；Heat controls；Metal surface is formed well
Inhibition protection, improve metal surface quality, improve fineness.1- octyl phosphonic acid because have excellent inhibition and lubrication,
Extreme pressure property, can add in the lubricant.Especially for non-ferrous metal, the long-time place of non-ferrous metal holds in the basic conditions
Easy to change, make metal lose original gloss, and 1- octyl phosphonic acid can be used in the processing and lubrication liquid of the metals such as aluminium, magnesium, zinc, use
Make corrosion inhibitor, metal variable color can be prevented；Therefore, 1- octyl phosphonic acid is studied and current non-ferrous metals processing lubrication is sent out
Exhibition is significant.
Through experimental studies have found that, 1- octyl phosphonic acid to corrosion inhibition for metal effect preferably, excellent performance, but difficult in prior art
To inquire the technology of preparing of correlation, 1- octyl phosphonic acid is caused also not obtain greatly as metal inhibitor in processing and lubrication liquid
Scale popularization and application.
Chinese Patent Application No.：201410577208.X, the applying date：On October 27th, 2014, this application case discloses one
Plant the method catalyzing and synthesizing iso-octyl phosphonic acids di-isooctyl, phosphonic acids di-isooctyl and caustic alcohol react and obtain phosphonic acids di-isooctyl
Sodium, phosphonic acids di-isooctyl sodium again with chloro-iso-octane iodine alkali metal salt be catalyzed under, 150～160 DEG C react 2～4h, so
After saponification, point liquid, distillation obtain target product iso-octyl phosphonic acids di-isooctyl.The system to iso-octyl phosphonic acids di-isooctyl for the program
Standby be described, but cannot therefrom learn how to prepare octyl phosphonic acid it is impossible to meet the demand to the preparation of non-ferrous metal lubricant.
Content of the invention
1. invent technical problem to be solved
It is an object of the invention to overcome the shortcomings of to lack in prior art effectively preparing high recovery rate 1- octyl phosphonic acid, carry
Supply a kind of synthetic method of the 1- octyl phosphonic acid for corrosion inhibition for metal, technical scheme, with 1- bromooctane and phosphorous
Triethylenetetraminehexaacetic acid ester prepares 1- octyl phosphonic acid for raw material, and reaction condition is gentle, and course of reaction is easily controllable, and product recovery rate is high, and
Reactant can recycle after the reaction, does not result in environmental pollution and wastage of material.
2. technical scheme
For reaching above-mentioned purpose, the technical scheme that the present invention provides is：
A kind of synthetic method of 1- octyl phosphonic acid for corrosion inhibition for metal of the present invention, comprises the following steps：
(1) under room temperature, 1- bromooctane is mixed with catalyst by proportion stirring, then be warming up to 70～90 DEG C, then by phosphorous
Triethylenetetraminehexaacetic acid ester drips into reaction system, exothermic heat of reaction, controls temperature at 70～120 DEG C, and time for adding is 2～3h；It is added dropwise to complete
Afterwards, system temperature is risen to 130～160 DEG C, insulation 2～4h proceeds to react；
(2) after step (1) reaction terminates, system is cooled to 60～80 DEG C, in reactor, drips aqueous solution of hydrogen bromide,
Time for adding is 0.5～1h；Then heat to flow back, keep 2～4h to be reacted；
(3) after step (2) reaction terminates, first at ambient pressure the aqueous solution of hydrogen bromide in reaction system is steamed, then take out
During vacuum will be reacted, excessive 1- bromooctane steams；
(4) after distillation terminates, it is down to room temperature, n-hexane and water are put in reactor in proportion, extraction point liquid；By lower floor
Aqueous phase separation, upper oil phase steams n-hexane at normal pressure, 70～85 DEG C, that is, 1- octyl phosphonic acid is obtained.
As further improvement of the present invention, in step (1), 1- bromooctane and the mol ratio of triethyl phosphite are
1.2:1～2.5:1.
As further improvement of the present invention, described catalyst is AlCl3、FeCl3One of or two kinds.
As further improvement of the present invention, described catalyst amount be 1- bromooctane and triethyl phosphite quality it
The 0.5%～2.0% of sum.
As further improvement of the present invention, in step (2), the concentration of aqueous solution of hydrogen bromide is 35%～42%, bromination
Hydrogen is 2.0 with the mol ratio of triethyl phosphite:1～2.5:1.
As further improvement of the present invention, step steams aqueous solution of hydrogen bromide in (3) under the conditions of 105～120 DEG C；
Excessive 1- bromooctane in reaction system is steamed under the conditions of 90～100 DEG C, vacuum 2.5～4.5kPa.
As further improvement of the present invention, in the extraction of step (4), n-hexane and the volume ratio of water are 5:1～6:1.
3. beneficial effect
The technical scheme being provided using the present invention, compared with prior art, is had the advantages that：
(1) synthetic method of a kind of 1- octyl phosphonic acid for corrosion inhibition for metal of the present invention, reaction raw materials low cost, easily takes
, and react after can recycling, both contributed to environmental protection, do not resulted in waste again；
(2) a kind of synthetic method of 1- octyl phosphonic acid for corrosion inhibition for metal of the present invention, anti-using Louis acid catalysis
Should, then hydrolysis preparation 1- octyl phosphonic acid, the process is simple of this synthetic method in acid condition, reaction condition is gentle, through after
Phase sampling detection finds that the recovery rate of 1- octyl phosphonic acid and chromatographic purity are all very high.
Specific embodiment
For further appreciating that present disclosure, the present invention is described in detail in conjunction with the embodiments.
Embodiment 1
Under room temperature, 1.2mol 1- bromooctane is put into 1000ml flask, adds 2.0g ferric trichloride, stir,
It is warming up to 75 DEG C again, drip 1.0mol triethyl phosphite, exothermic heat of reaction, between 75～110 DEG C, 2.0h drips temperature control
Complete.After completion of dropwise addition, it is warming up to 150 DEG C, insulation 2h proceeds to react.After reaction terminates, it is cooled to 70 DEG C, will
405.0g concentration is that 40% aqueous solution of hydrogen bromide drips into reaction system, and 30min drips.After being added dropwise to complete, it is warming up to back
2h is kept to proceed to react under stream mode.After reaction terminates, aqueous solution of hydrogen bromide is steamed for 115 DEG C by elder generation at ambient pressure, reclaims
These aqueous solution of hydrogen bromide；In vacuum 2.92kPa, under the conditions of 93 DEG C, steam 1- bromooctane；Then it is down to room temperature, by volume
Than for 5:1 n-hexane and the mixed solution of water are poured in reactor, all pour separatory funnel, extraction point liquid after stirring into；Will
Lower floor's aqueous phase liquid reclaims, and upper oil phase transfers in flask, steams n-hexane, just reclaiming these at normal pressure, 70 DEG C
Hexane, that is, obtain 1- octyl phosphonic acid；The yield of this reaction is 90.9%；Sample analysis, the chromatographic purity of product is 97.4%.
Embodiment 2
Under room temperature, 1.2mol1- bromooctane is put into 1000ml flask, adds 3.60g ferric trichloride, stir,
It is warming up to 75 DEG C again, drip 1.0mol triethyl phosphite, exothermic heat of reaction, between 75～115 DEG C, 2.5h drips temperature control
Complete.After completion of dropwise addition, it is warming up to 160 DEG C, insulation 3h proceeds to react.After reaction terminates, it is cooled to 70 DEG C, will
405.0g concentration is that 40% aqueous solution of hydrogen bromide drips into reaction system, and 50min drips.After being added dropwise to complete, it is warming up to back
Under stream mode, 3h is kept to be reacted.After reaction terminates, aqueous solution of hydrogen bromide is steamed for 115 DEG C by elder generation at ambient pressure, reclaims these
Aqueous solution of hydrogen bromide；In vacuum 4.5kPa, under the conditions of 100 DEG C, steam 1- bromooctane；Then it is down to room temperature, volume ratio is
5.5:1 n-hexane and the mixed solution of water are poured in reactor, all pour separatory funnel, extraction point liquid after stirring into；Under inciting somebody to action
Layer aqueous phase liquid reclaims, and upper oil phase transfers in flask, steams n-hexane at normal pressure, 80 DEG C, reclaims these just own
Alkane, that is, obtain 1- octyl phosphonic acid；The yield of this reaction is 91.7%；Sample analysis, the chromatographic purity of product is 97.4%.
Embodiment 3
Under room temperature, 1.2mol 1- bromooctane is put into 1000ml flask, add 7.20g ferric trichloride, stir, then
It is warming up to 80 DEG C, drip 1.0mol triethyl phosphite, between 80～110 DEG C, 3.0h is added dropwise to complete temperature control.Dropping knot
Shu Hou, is warming up to 150 DEG C, and insulation 4h proceeds to react.After reaction terminates, it is cooled to 70 DEG C, 405.0g concentration is 40%
Aqueous solution of hydrogen bromide drip into reaction system, 60min drips.After being added dropwise to complete, it is warming up under reflux state, keep 4h to enter
Row reaction.After reaction terminates, aqueous solution of hydrogen bromide is steamed for 120 DEG C by elder generation at ambient pressure, reclaims these aqueous solution of hydrogen bromide；True
Reciprocal of duty cycle 2.5kPa, steams 1- bromooctane under the conditions of 90 DEG C；Then it is down to room temperature, volume ratio is 5:1 n-hexane is mixed with water
Close solution and pour in reactor, after stirring, all pour separatory funnel, extraction point liquid into；Lower floor's aqueous phase liquid is reclaimed, upper strata oil
Mutually transfer in flask, at normal pressure, 85 DEG C, n-hexane is steamed, reclaim these n-hexanes, that is, obtain 1- octyl phosphonic acid；Should
The yield of reaction is 92.9%；Sample analysis, the chromatographic purity of product is 97.6%.
Embodiment 4
Under room temperature, 2.0mol 1- bromooctane is put into 1000ml flask, add 1.2g ferric trichloride, 1.75g tri-chlorination
Aluminium, stirs, then is warming up to 90 DEG C, drip 1.0mol triethyl phosphite, temperature control between 90～120 DEG C, 2.0h
It is added dropwise to complete.After completion of dropwise addition, it is warming up to 130 DEG C, insulation 2h proceeds to react.After reaction terminates, it is cooled to 70 DEG C, will
506.0g concentration is 35% aqueous solution of hydrogen bromide dropping entrance reaction system, and 30min drips.After being added dropwise to complete, it is warming up to
Under reflux state, 2h is kept to be reacted.After reaction terminates, aqueous solution of hydrogen bromide is steamed for 120 DEG C by elder generation at ambient pressure, reclaims this
A little aqueous solution of hydrogen bromide；In vacuum 4.5kPa, under the conditions of 100 DEG C, steam 1- bromooctane；Then it is down to room temperature, volume ratio is
6:1 n-hexane and the mixed solution of water are poured in reactor, all pour separatory funnel, extraction point liquid after stirring into；By lower floor
Aqueous phase liquid reclaims, and upper oil phase transfers in flask, steams n-hexane, reclaim these n-hexanes at normal pressure, 70 DEG C,
Obtain 1- octyl phosphonic acid；The yield of this reaction is 94.2%；Sample analysis, the chromatographic purity of product is 98.2%.
Embodiment 5
Under room temperature, 2.5mol 1- bromooctane is put into 1000ml flask, add 6.50g alchlor, stir, then
It is warming up to 70 DEG C, drip 1.0mol triethyl phosphite, between 70～100 DEG C, 2.5h is added dropwise to complete temperature control.Dropping knot
After bundle, it is warming up to 150 DEG C, insulation 3h proceeds to react.After reaction terminates, it is cooled to 60 DEG C, 506.0g concentration is
40% aqueous solution of hydrogen bromide drips into reaction system, and 50min is added dropwise to complete.After being added dropwise to complete, it is warming up under reflux state, protect
Hold 3h to be reacted.After reaction terminates, aqueous solution of hydrogen bromide is steamed for 115 DEG C by elder generation at ambient pressure, reclaims these hydrogen bromides water-soluble
Liquid；In vacuum 3.5kPa, under the conditions of 95 DEG C, steam 1- bromooctane；Then it is down to room temperature, volume ratio is 6:1 n-hexane with
The mixed solution of water is poured in reactor, all pours separatory funnel, extraction point liquid after stirring into；Lower floor's aqueous phase liquid is reclaimed,
Upper oil phase transfers in flask, steams n-hexane, reclaims these n-hexanes, that is, obtain 1- octyl group at normal pressure, 80 DEG C
Phosphonic acids；The yield of this reaction is 94.8%；Sample analysis, the chromatographic purity of product is 98.2%.
Embodiment 6
Under room temperature, 2.5mol 1- bromooctane is put into 1000ml flask, add 12.9g alchlor, stir, then
It is warming up to 85 DEG C, drip 1.0mol triethyl phosphite, between 85～105 DEG C, 3.0h is added dropwise to complete temperature control.Dropping knot
After bundle, it is warming up to 160 DEG C, insulation 4h proceeds to react.After reaction terminates, it is cooled to 80 DEG C, 506.0g concentration is
40% aqueous solution of hydrogen bromide dropping enters reaction system, and 60min drips.After being added dropwise to complete, it is warming up under reflux state, protect
Hold 4h to be reacted.After reaction terminates, aqueous solution of hydrogen bromide is steamed for 105 DEG C by elder generation at ambient pressure, reclaims these hydrogen bromides water-soluble
Liquid；In vacuum 2.5kPa, under the conditions of 90 DEG C, steam 1- bromooctane；Then it is down to room temperature, volume ratio is 6:1 n-hexane with
The mixed solution of water is poured in reactor, all pours separatory funnel, extraction point liquid after stirring into；Lower floor's aqueous phase liquid is reclaimed,
Upper oil phase transfers in flask, steams n-hexane, reclaims these n-hexanes, that is, obtain 1- octyl group at normal pressure, 85 DEG C
Phosphonic acids；The yield of this reaction is 95.1%；Sample analysis, the chromatographic purity of product is 98.2%.
Prepare the 1- octyl phosphonic acid for metal inhibitor using the synthetic method of embodiment 1～6, this synthetic method former
Material is easy to get, and reaction condition is gentle, and reaction conversion ratio is high, and wastewater and waste materials can be carried out recycling, and is conducive to environmental protection.
Below schematically the present invention and embodiments thereof are described, this description does not have restricted, actual knot
Structure is not limited thereto.So, if those of ordinary skill in the art is enlightened by it, without departing from the invention objective
In the case of, design the frame mode similar to this technical scheme and embodiment without creative, all should belong to the present invention's
Protection domain.
Claims (7)
1. a kind of synthetic method of the 1- octyl phosphonic acid for corrosion inhibition for metal, comprises the following steps：
(1) under room temperature, 1- bromooctane is mixed with catalyst by proportion stirring, then be warming up to 70～90 DEG C, then by phosphorous acid three
Ethyl ester drips into reaction system, controls temperature at 70～120 DEG C, and time for adding is 2～3h；After being added dropwise to complete, by system temperature
Rise to 130～160 DEG C, insulation 2～4h proceeds to react；
(2) after step (1) reaction terminates, system is cooled to 60～80 DEG C, drips aqueous solution of hydrogen bromide, dropping in reactor
Time is 0.5～1h；Then heat to flow back, keep 2～4h to be reacted；
(3) after step (2) reaction terminates, first at ambient pressure the aqueous solution of hydrogen bromide in reaction system is steamed, then vacuumize
Excessive 1- bromooctane in reaction is steamed；
(4) after distillation terminates, it is down to room temperature, n-hexane and water are put in reactor in proportion, extraction point liquid；By lower floor's aqueous phase
Separate, upper oil phase steams n-hexane at normal pressure, 70～85 DEG C, that is, 1- octyl phosphonic acid is obtained.
2. a kind of 1- octyl phosphonic acid for corrosion inhibition for metal according to claim 1 synthetic method it is characterised in that：Step
Suddenly in (1), 1- bromooctane and the mol ratio of triethyl phosphite are 1.2:1～2.5:1.
3. a kind of 1- octyl phosphonic acid for corrosion inhibition for metal according to claim 1 synthetic method it is characterised in that：Institute
Stating catalyst is AlCl3、FeCl3One of or two kinds.
4. the synthetic method of a kind of 1- octyl phosphonic acid for corrosion inhibition for metal according to claim 1 or 2 or 3, its feature
It is：Described catalyst amount is the 0.5%～2.0% of 1- bromooctane and triethyl phosphite quality sum.
5. a kind of 1- octyl phosphonic acid for corrosion inhibition for metal according to claim 1 synthetic method it is characterised in that：Step
Suddenly in (2), the concentration of aqueous solution of hydrogen bromide is 35%～42%, and hydrogen bromide is 2.0 with the mol ratio of triethyl phosphite:1～
2.5:1.
6. a kind of 1- octyl phosphonic acid for corrosion inhibition for metal according to claim 1 synthetic method it is characterised in that：Step
Suddenly steam aqueous solution of hydrogen bromide under the conditions of 105～120 DEG C in (3)；Under the conditions of 90～100 DEG C, vacuum 2.5～4.5kPa
Steam excessive 1- bromooctane in reaction system.
7. a kind of 1- octyl phosphonic acid for corrosion inhibition for metal according to claim 1 synthetic method it is characterised in that：Step
Suddenly in the extraction of (4), n-hexane and the volume ratio of water are 5:1～6:1.
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| CN114437859B (en) * | 2021-10-29 | 2023-03-07 | 南京科润工业介质股份有限公司 | Long-acting corrosion-inhibition aluminum alloy cutting fluid |
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| US4069247A (en) * | 1974-08-31 | 1978-01-17 | Hoechst Aktiengesellschaft | Preparation of phosphonic and/or phosphinic acids |
| EP0529640A1 (en) * | 1991-08-29 | 1993-03-03 | DR. TH. BÖHME KG CHEM. FABRIK GMBH & CO. | Process for the preparation of alkanephosphonic acid |
| JP2001270888A (en) * | 2000-03-23 | 2001-10-02 | Miyoshi Oil & Fat Co Ltd | Method for manufacturing alkylphosphonic acid |
| CN104447864A (en) * | 2014-10-27 | 2015-03-25 | 三门峡中达化工有限公司 | Method for synthesizing isooctyl-diisooctyl phosphonate by catalysis |
-
2015
- 2015-09-21 CN CN201510604364.5A patent/CN105153224B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4069247A (en) * | 1974-08-31 | 1978-01-17 | Hoechst Aktiengesellschaft | Preparation of phosphonic and/or phosphinic acids |
| EP0529640A1 (en) * | 1991-08-29 | 1993-03-03 | DR. TH. BÖHME KG CHEM. FABRIK GMBH & CO. | Process for the preparation of alkanephosphonic acid |
| JP2001270888A (en) * | 2000-03-23 | 2001-10-02 | Miyoshi Oil & Fat Co Ltd | Method for manufacturing alkylphosphonic acid |
| CN104447864A (en) * | 2014-10-27 | 2015-03-25 | 三门峡中达化工有限公司 | Method for synthesizing isooctyl-diisooctyl phosphonate by catalysis |
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