CN104804782A - Method for preparing anti-wear agent for aircraft fuel - Google Patents
Method for preparing anti-wear agent for aircraft fuel Download PDFInfo
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- CN104804782A CN104804782A CN201510133557.7A CN201510133557A CN104804782A CN 104804782 A CN104804782 A CN 104804782A CN 201510133557 A CN201510133557 A CN 201510133557A CN 104804782 A CN104804782 A CN 104804782A
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Abstract
The invention relates to a method for preparing an anti-wear agent for aircraft fuel. The method comprises steps as follows: (A) preparation of mixed fatty acid; (B1), synthesis of C36 unsaturated fatty acid biopolymer, wherein linoleic acid or mixed fatty acid obtained in the step (A) is taken as a raw material and put in a high-pressure reaction kettle, 9%-15% of a catalyst and 0.5%-1.5% of an auxiliary agent are added, the high-pressure kettle is mounted well by the mass of linoleic acid or the mixed fatty acid, the airtightness is detected, the catalyst is treated clay, the auxiliary agent is lithium carbonate, the usage amount of the catalyst is preferably 10%-13%, and the usage amount of the auxiliary agent is preferably 0.8%-1.2%.
Description
Technical field
The present invention relates to a kind of method preparing the anti-wear agent of aviation fuel, especially a kind of preparation method of aviation fuel anti-wear agent of unsaturated fatty acids dipolymer type.
Background technology
At present, the anti-wear agent added in domestic air mail fuel is the active principle of T1602, T1602 is naphthenic acid, and naphthenic acid is the component wishing in rocket engine fuel processing to remove, and rejoin naphthenic acid the acidity of aviation fuel can be caused to increase, the corrodibility of rocket engine fuel also can be caused to increase.And the colourity of T1602 additive is comparatively dark, affects the colour index of aviation fuel, in addition, the unstable product quality of T1602.
Aviation fuel mainly adopts acid-alkali refining, hydrofining or hydrocracking in process of production, natural wear-resistant composition in cut is removed, cause aviation fuel abrasion resistance to reduce, therefore must add anti-wear agent in aviation fuel, prevent the heavy wear of fuel system.
Summary of the invention
In order to overcome the deficiencies in the prior art, the present invention proposes a kind of anti-wear agent of aviation fuel, be particularly useful for the anti-wear agent of rocket engine fuel, the unexpected discovery of contriver, owing to adopting anti-wear agent of the present invention, greatly improves the corrosive nature of former cycloalkanes acid type additive.
A kind of anti-wear agent of aviation fuel, comprise C36 unsaturated fatty acids dipolymer, this C36 unsaturated fatty acids dipolymer comprises: the compound more than 65% shown in general formula (1), compound 25-30% shown in general formula (2), compound shown in general formula (3) lower than 10%, in mass.
Above-mentioned C36 unsaturated fatty acids dipolymer prepares as follows:
(A) preparation of mixed fatty acid: comprise vegetables oil to mix with excessive alkaline solution and appropriate ethanol and carry out saponification and slough glycerine, generate soap, soap is through being acidified to pH=2 ~ 3, adopt petroleum ether extraction oil phase, oil phase is after washing, anhydrous sodium sulfate drying, adopt rotary evaporation removing sherwood oil, after vacuum-drying mixed fatty acid;
(B1) synthesis of C36 unsaturated fatty acids dipolymer, comprises the steps:
(1) be placed in autoclave using the mixed fatty acid of linolic acid or step (A) gained as raw material, add the catalyzer of 9-15% and the auxiliary agent of 0.5-1.5% again, based on the quality meter of linolic acid or above-mentioned mixed fatty acid, install autoclave, and check resistance to air loss, wherein catalyzer is treated earth, auxiliary agent is Quilonum Retard, the preferred 10-13% of usage quantity of catalyzer, more preferably 12%, the preferred 0.8-1.2% of usage quantity of auxiliary agent, more preferably 1.0%;
(2) use nitrogen purging autoclave three times, discharge the air in autoclave, then inflated with nitrogen is to 2.0MPa, closes autoclave intake valve;
(3) under the condition stirred, be heated to temperature of reaction 230-240 DEG C, when arriving temperature of reaction, start timing, as reacting zero point;
(4) react after within 5-6 hour, terminating, stop heating, autoclave kettle is placed in cold water, makes kettle drop to room temperature rapidly, drives still, and pour out reaction product;
(5) crude product equal-volume sherwood oil dilution, and add excessive hydrochloric acid and be acidified to pH=2 ~ 3;
(6) after acidifying, mixture is carried out centrifugation, removing catalyzer and solid impurity;
(7) supernatant liquid deionized water is washed till neutrality, separatory, upper oil phase anhydrous sodium sulfate drying, hold over night, crosses and filters anhydrous sodium sulphate;
(8) rotary evaporation in vacuo removing sherwood oil, remove unreacted monomer acids finally by underpressure distillation, the condition of underpressure distillation is: gas phase temperature is 240 DEG C, and residual voltage is 133Pa (1mmHg), obtains refined products.
Step B1 can adopt step B2 to replace, and step B2 comprises the steps:
(1) be placed in autoclave using the mixed fatty acid of linolic acid or step (A) gained as raw material, add the ionic liquid of 9-15% again as catalyzer, based on the quality meter of linolic acid or above-mentioned mixed fatty acid, install autoclave, and check resistance to air loss, the preferred 10-13% of usage quantity of catalyzer, more preferably 12%, ionic liquid is ionic liquid I or the ionic liquid II with following structural formula
(2) use nitrogen purging autoclave three times, discharge the air in autoclave, then inflated with nitrogen is to 2.0MPa, closes autoclave intake valve;
(3) under the condition stirred, be heated to temperature of reaction 230-240 DEG C, when arriving temperature of reaction, start timing, as reacting zero point;
(4) react after within 5-6 hour, terminating, stop heating, autoclave kettle is placed in cold water, makes kettle drop to room temperature rapidly, drives still, and pour out reaction product;
(5) crude product equal-volume sherwood oil dilution, and add excessive hydrochloric acid and be acidified to pH=2 ~ 3;
(6) after acidifying, supernatant liquid deionized water is washed till neutrality, separatory, upper oil phase anhydrous sodium sulfate drying, hold over night, and cross and filter anhydrous sodium sulphate, the ionic liquid of lower floor is recyclable to be recycled;
(7) rotary evaporation in vacuo removing sherwood oil, remove unreacted monomer acids finally by underpressure distillation, the condition of underpressure distillation is: gas phase temperature is 240 DEG C, and residual voltage is 133Pa (1mmHg), obtains refined products.
The synthesis of ionic liquid I:
Ionic liquid I specifically adopts following preparation method:
(1) in Erlenmeyer flask, trimethylamine solution is mixed with PS etc. mole, stirring reaction 24h at 60 DEG C;
(2), after reaction terminates, rotary distillation, except anhydrating, obtains white solid;
(3) by re-crystallizing in ethyl acetate, suction filtration, and wash three times;
(4) vacuum-drying (80 DEG C) 4h obtains the solid inner salt of white;
(5) with the water dissolution inner salt of 3 times of quality;
(6) drip the hcl acidifying that equimolar mass concentration is 37%, dropwise, be warming up to 80 DEG C, stirring reaction 3h.
(7) rotary distillation is except anhydrating, and vacuum-drying (80 DEG C) 4h, obtains light yellow viscous liquid, i.e. acidifying inner salt;
(8) get a certain amount of acidifying inner salt, the zinc chloride being 1:2 with mol ratio mixes, and under nitrogen protection, is warming up to 100 DEG C, is stirred to solid and all dissolves;
(9) vacuum-drying (80 DEG C) 8h, obtains thick ionic liquid I.
The synthesis of ionic liquid II:
The concrete synthesis step of ionic liquid II is as follows:
(1) a certain amount of PS being dissolved in its total mass number is in the ethyl acetate of 5 ~ 10 times, is warming up to 40 ~ 60 DEG C, drips equimolar N-Methylimidazole.Dropwise, insulation reaction 3 ~ 5h;
(2), after reaction terminates, suction filtration, obtains white filter cake, and filter cake ethyl acetate washs three times;
(3) vacuum-drying (100 DEG C) 2h obtains white solid inner salt 3-(1-Methylimidazole-3-alkyl)-propyl sulfonic acid salt (mim-PS);
(4) get a certain amount of inner salt mim-PS, being dissolved in its total mass number is in the deionized water of 2 ~ 4 times;
(5) drip the hydrochloric acid that equimolar mass concentration is 37%, acidifying is complete, is warming up to 70 ~ 90 DEG C, stirring reaction 2 ~ 3h;
(6) rotary distillation is except anhydrating, and vacuum-drying (80 DEG C) 4h, obtains light yellow viscous liquid, i.e. acidifying inner salt chlorination 1-(3-sulfonic acid)-propyl group-3-methylimidazole salt [HO
3s-(CH
2)
3-mim] Cl;
(7) get a certain amount of acidifying inner salt, the zinc chloride being 1:2 with mol ratio mixes, and under nitrogen protection, is warming up to 90 ~ 110 DEG C, is stirred to solid and all dissolves;
(8) vacuum-drying (80 DEG C) 8h, obtains thick ionic liquid II.
Accompanying drawing explanation
Fig. 1 is that the impact of number of times on C36 unsaturated fatty acids dipolymer (KM3) yield reused by catalyzer
embodiment
Embodiment 1
Prepare mixed fatty acid:
(1) 100g sunflower seed oil is accurately taken in 250mL there-necked flask.
(2) 40g KOH is added, 95% ethanolic soln of 80g deionized water (or 40ml 50%KOH solution) and 160ml.
(3) under 90 DEG C of glycerol bath conditions, stirring and refluxing saponification 2h, obtains saponification liquor (saponification liquor that takes a morsel is water-soluble, if leave standstill without oil reservoir, then saponification is complete).
(4) treat that saponification liquor is cooled to room temperature, add dilute hydrochloric acid and be acidified to pH=2 ~ 3, with a small amount of petroleum ether extraction oil phase.
(5) acidifying is complete, is washed till neutrality with deionized water, separatory.Upper oil phase anhydrous sodium sulfate drying, hold over night.
(6) excessively anhydrous sodium sulphate is filtered.
(7) rotary evaporation in vacuo removing sherwood oil, vacuum-drying, obtains mixed fatty acid.
Embodiment 2
The synthesis of C36 unsaturated fatty acids dipolymer:
(1) be placed in autoclave as raw material using the mixed fatty acid of embodiment 1 gained, then add the catalyzer of 12% and the auxiliary agent of 1%, based on the quality meter of above-mentioned mixed fatty acid, install autoclave, and check resistance to air loss, wherein catalyzer is treated earth, and auxiliary agent is Quilonum Retard;
(2) use nitrogen purging autoclave three times, discharge the air in autoclave, then inflated with nitrogen is to 2.0MPa, closes autoclave intake valve;
(3) under the condition stirred, be heated to temperature of reaction 240 DEG C, when arriving temperature of reaction, start timing, as reacting zero point;
(4) react after within 6 hours, terminating, stop heating, autoclave kettle is placed in cold water, makes kettle drop to room temperature rapidly, drives still, and pour out reaction product;
(5) crude product equal-volume sherwood oil dilution, and add excessive hydrochloric acid and be acidified to pH=2 ~ 3;
(6) after acidifying, mixture is carried out centrifugation, removing catalyzer and solid impurity;
(7) supernatant liquid deionized water is washed till neutrality, separatory, upper oil phase anhydrous sodium sulfate drying, hold over night, crosses and filters anhydrous sodium sulphate;
(8) rotary evaporation in vacuo removing sherwood oil, remove unreacted monomer acids finally by underpressure distillation, the condition of underpressure distillation is: gas phase temperature is 240 DEG C, and residual voltage is 133Pa (1mmHg), obtain refined products, the yield of C36 unsaturated fatty acids dipolymer is 67.6%.
Embodiment 3
The synthesis of C36 unsaturated fatty acids dipolymer:
(1) be placed in autoclave as raw material using linolic acid, then add the catalyzer of 12% and the auxiliary agent of 1%, based on above-mentioned linoleic quality meter, install autoclave, and check resistance to air loss, wherein catalyzer is treated earth, and auxiliary agent is Quilonum Retard;
(2) use nitrogen purging autoclave three times, discharge the air in autoclave, then inflated with nitrogen is to 2.0MPa, closes autoclave intake valve;
(3) under the condition stirred, be heated to temperature of reaction 230 DEG C, when arriving temperature of reaction, start timing, as reacting zero point;
(4) react after within 6 hours, terminating, stop heating, autoclave kettle is placed in cold water, makes kettle drop to room temperature rapidly, drives still, and pour out reaction product;
(5) crude product equal-volume sherwood oil dilution, and add excessive hydrochloric acid and be acidified to pH=2 ~ 3;
(6) after acidifying, mixture is carried out centrifugation, removing catalyzer and solid impurity;
(7) supernatant liquid deionized water is washed till neutrality, separatory, upper oil phase anhydrous sodium sulfate drying, hold over night, crosses and filters anhydrous sodium sulphate;
(8) rotary evaporation in vacuo removing sherwood oil, remove unreacted monomer acids finally by underpressure distillation, the condition of underpressure distillation is: gas phase temperature is 240 DEG C, and residual voltage is 133Pa (1mmHg), obtain refined products, the yield of C36 unsaturated fatty acids dipolymer is 88.7%.
Embodiment 4
The synthesis of C36 unsaturated fatty acids dipolymer:
(1) be placed in autoclave using the mixed fatty acid of embodiment 1 gained as raw material, then the ionic liquid I adding 10% is as catalyzer, based on the quality meter of above-mentioned mixed fatty acid, installs autoclave, and checks resistance to air loss
(2) use nitrogen purging autoclave three times, discharge the air in autoclave, then inflated with nitrogen is to 2.0MPa, closes autoclave intake valve;
(3) under the condition stirred, be heated to temperature of reaction 230 DEG C, when arriving temperature of reaction, start timing, as reacting zero point;
(4) react after within 5 hours, terminating, stop heating, autoclave kettle is placed in cold water, makes kettle drop to room temperature rapidly, drives still, and pour out reaction product;
(5) crude product equal-volume sherwood oil dilution, and add excessive hydrochloric acid and be acidified to pH=2 ~ 3;
(6) after acidifying, supernatant liquid deionized water is washed till neutrality, separatory, upper oil phase anhydrous sodium sulfate drying, hold over night, and cross and filter anhydrous sodium sulphate, the ionic liquid of lower floor is recyclable to be recycled;
(7) rotary evaporation in vacuo removing sherwood oil, remove unreacted monomer acids finally by underpressure distillation, the condition of underpressure distillation is: gas phase temperature is 240 DEG C, and residual voltage is 133Pa (1mmHg), obtain refined products, the yield of C36 unsaturated fatty acids dipolymer is 63.3%.
Embodiment 5
The synthesis of C36 unsaturated fatty acids dipolymer:
Using ionic liquid II as catalyzer, other conditions are all identical with embodiment 5, prepare refined products, and the yield of C36 unsaturated fatty acids dipolymer is 64.9%.
Embodiment 6
The synthesis of C36 unsaturated fatty acids dipolymer:
Take linolic acid as raw material, other conditions are identical with embodiment 5, obtain refined products, and the yield of C36 unsaturated fatty acids dipolymer is 86.5%.
Embodiment 8
The synthesis of C36 unsaturated fatty acids dipolymer:
Take linolic acid as raw material, using ionic liquid II as catalyzer, other conditions are all identical with embodiment 5, prepare refined products, and the yield of C36 unsaturated fatty acids dipolymer is 87.4%.
Embodiment 9
When identical with the reaction conditions of embodiment 4, investigated ion I liquid and reused the impact of number of times on C36 unsaturated fatty acids dipolymer yield, result as shown in Figure 1:
As seen from Figure 1, after ionic liquid I reuses 5 times, the yield kept stable of C36 unsaturated fatty acids dipolymer, illustrates that ionic liquid has good repeat performance.This can explain from two aspects: (1) ionic liquid
acid sites is positioned at the alkylsulphonic acid that covalent linkage is connected on its positively charged ion, Lewis acid sites be then to water and
negatively charged ion [the Zn that acidic substance are stable
2cl
5]
-, therefore the acid sites of ionic liquid not easily runs off; (2) ZnCl
2introducing make the viscosity of ionic liquid and proportion all comparatively large, be conducive to it and be separated with reaction mixture, make the loss of ionic liquid in sepn process very little.
Wear-resistant and corrosion resistant testing data: unsaturated acid, because the existence of double bond, easier in metallic surface formation adsorption film, therefore abrasion resistance is better than linear saturated fatty acids.The corrodibility of naphthenic acid is larger than dimeracid.
This agent adds in No. 3 rocket engine fuels of hydrogenation technique production should meet following index (add-on 15 ~ 23mg/L):
1. oilness: wear scar diameter (WSD) is less than 0.65mm.(SH/T 0687) representative value 0.59mm
2. water separation index: MSEP >=75.(SH/T 0616) representative value 85 ~ 95
3. copper corrosion: be less than or equal to 1 grade (GB/T5096)
Claims (1)
1. prepare a method for the anti-wear agent of aviation fuel, the method comprises:
(A) preparation of mixed fatty acid: comprise vegetables oil to mix with excessive alkaline solution and appropriate ethanol and carry out saponification and slough glycerine, generate soap, soap is through being acidified to pH=2 ~ 3, adopt petroleum ether extraction oil phase, oil phase is after washing, anhydrous sodium sulfate drying, adopt rotary evaporation removing sherwood oil, after vacuum-drying mixed fatty acid;
(B1) synthesis of C36 unsaturated fatty acids dipolymer, comprises the steps:
(1) be placed in autoclave using the mixed fatty acid of linolic acid or step (A) gained as raw material, add the catalyzer of 9-15% and the auxiliary agent of 0.5-1.5% again, based on the quality meter of linolic acid or above-mentioned mixed fatty acid, install autoclave, and check resistance to air loss, wherein catalyzer is treated earth, auxiliary agent is Quilonum Retard, the preferred 10-13% of usage quantity of catalyzer, more preferably 12%, the preferred 0.8-1.2% of usage quantity of auxiliary agent, more preferably 1.0%;
(2) use nitrogen purging autoclave three times, discharge the air in autoclave, then inflated with nitrogen is to 2.0MPa, closes autoclave intake valve;
(3) under the condition stirred, be heated to temperature of reaction 230-240 DEG C, when arriving temperature of reaction, start timing, as reacting zero point;
(4) react after within 5-6 hour, terminating, stop heating, autoclave kettle is placed in cold water, makes kettle drop to room temperature rapidly, drives still, and pour out reaction product;
(5) crude product equal-volume sherwood oil dilution, and add excessive hydrochloric acid and be acidified to pH=2 ~ 3;
(6) after acidifying, mixture is carried out centrifugation, removing catalyzer and solid impurity;
(7) supernatant liquid deionized water is washed till neutrality, separatory, upper oil phase anhydrous sodium sulfate drying, hold over night, crosses and filters anhydrous sodium sulphate;
(8) rotary evaporation in vacuo removing sherwood oil, unreacted monomer acids is removed finally by underpressure distillation, the condition of underpressure distillation is: gas phase temperature is 240 DEG C, residual voltage is 133Pa (1mmHg), obtain refined products, this refined products comprises C36 unsaturated fatty acids dipolymer, this C36 unsaturated fatty acids dipolymer comprises: the compound more than 65% shown in general formula (1), compound 25-30% shown in general formula (2), compound shown in general formula (3) is lower than 10%, in mass
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109879743A (en) * | 2017-12-06 | 2019-06-14 | 中国石油化工股份有限公司 | A method of using tung oil as Material synthesis dimeric dibasic acid |
| CN110746288A (en) * | 2019-09-26 | 2020-02-04 | 广饶县信和化工有限公司 | Catalytic synthesis method for improving yield and product quality of dimer acid |
| CN111349037A (en) * | 2018-12-21 | 2020-06-30 | 中国石油化工股份有限公司 | Monoacid type aviation fuel antiwear agent and preparation method thereof |
| CN112538391A (en) * | 2019-09-23 | 2021-03-23 | 中国石油化工股份有限公司 | Dimer acid antiwear agent composition and preparation method and application thereof |
| CN112538009A (en) * | 2019-09-23 | 2021-03-23 | 中国石油化工股份有限公司 | Dimer acid, continuous production method thereof, continuous production system and application |
| CN112536060A (en) * | 2019-09-23 | 2021-03-23 | 中国石油化工股份有限公司 | Catalyst for preparing dimer acid, dimer acid and preparation method and application thereof |
| CN114686288A (en) * | 2020-12-31 | 2022-07-01 | 中国石油化工股份有限公司 | Bio-based aviation fuel antiwear agent and preparation method thereof |
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| CN102070437A (en) * | 2011-01-06 | 2011-05-25 | 陈春林 | Method for polymerizing unsaturated fatty acid in presence of water |
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| JPH09272880A (en) * | 1996-04-03 | 1997-10-21 | Sanyo Chem Ind Ltd | Fuel oil composition |
| CN101565367A (en) * | 2009-05-27 | 2009-10-28 | 浙江大学 | Preparation method of conjugated linoleic acid |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109879743B (en) * | 2017-12-06 | 2022-06-07 | 中国石油化工股份有限公司 | Method for synthesizing dimer acid by taking tung oil as raw material |
| CN109879743A (en) * | 2017-12-06 | 2019-06-14 | 中国石油化工股份有限公司 | A method of using tung oil as Material synthesis dimeric dibasic acid |
| CN111349037B (en) * | 2018-12-21 | 2021-10-08 | 中国石油化工股份有限公司 | Monoacid type aviation fuel antiwear agent and preparation method thereof |
| CN111349037A (en) * | 2018-12-21 | 2020-06-30 | 中国石油化工股份有限公司 | Monoacid type aviation fuel antiwear agent and preparation method thereof |
| CN112538391A (en) * | 2019-09-23 | 2021-03-23 | 中国石油化工股份有限公司 | Dimer acid antiwear agent composition and preparation method and application thereof |
| CN112536060A (en) * | 2019-09-23 | 2021-03-23 | 中国石油化工股份有限公司 | Catalyst for preparing dimer acid, dimer acid and preparation method and application thereof |
| CN112538009A (en) * | 2019-09-23 | 2021-03-23 | 中国石油化工股份有限公司 | Dimer acid, continuous production method thereof, continuous production system and application |
| CN112538391B (en) * | 2019-09-23 | 2023-01-13 | 中国石油化工股份有限公司 | Dimer acid antiwear agent composition and preparation method and application thereof |
| CN112536060B (en) * | 2019-09-23 | 2023-04-07 | 中国石油化工股份有限公司 | Catalyst for preparing dimer acid, dimer acid and preparation method and application of dimer acid |
| CN112538009B (en) * | 2019-09-23 | 2023-04-07 | 中国石油化工股份有限公司 | Dimer acid, continuous production method thereof, continuous production system and application |
| CN110746288A (en) * | 2019-09-26 | 2020-02-04 | 广饶县信和化工有限公司 | Catalytic synthesis method for improving yield and product quality of dimer acid |
| CN114686288A (en) * | 2020-12-31 | 2022-07-01 | 中国石油化工股份有限公司 | Bio-based aviation fuel antiwear agent and preparation method thereof |
| CN114686288B (en) * | 2020-12-31 | 2023-05-26 | 中国石油化工股份有限公司 | Bio-based aviation fuel antiwear agent and preparation method thereof |
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