A kind of alcohol amino alkyl glycoside polyether and its application

Abstract

The present invention provides an alcohol amino alkyl glycoside polyether and its application. The structural formula of the alcohol amino alkyl glycoside polyether is shown in Formula I), #imgabs0# wherein m is an integer from 1 to 3, n is an integer from 1 to 5, o is an integer from 1 to 3, p is 9 to 18, and R1 is -C 16 H 33 or ‑C 18 H 37 , R2 is ‑H or ‑CH3, and R3 is ‑CH2 or ‑C2H4.

Description

Technical Field

[0001] The invention provides an alcohol amino hexadecyl glycoside polyether. Background Art

[0002] Wellbore instability during oil and gas drilling has always been a major factor hindering the smooth progress of drilling operations. In recent years, with the increasing number of complex wells such as deep and ultra-deep wells, horizontal wells with long lateral sections, and extended reach wells, the requirements for drilling fluid treatment agents to inhibit collapse and lubricate and prevent sticking have become increasingly stringent. According to statistics, over 90% of wellbore instability occurs in shale and shale-bearing formations. Furthermore, with increasingly stringent environmental protection requirements and increased awareness of reservoir protection, drilling fluid treatment agents are required to exhibit excellent environmental and reservoir protection properties.

[0003] In the 1990s, alkyl glycosides were used in drilling fluids, demonstrating excellent anti-caving, lubrication, and anti-sticking properties. They also exhibited good compatibility, were non-biotoxic, and were environmentally friendly. However, they had drawbacks such as requiring high addition levels (>35%), poor adsorption capacity, and insufficient temperature resistance. Summary of the Invention

[0004] One aspect of the present invention provides an alcohol amino alkyl glycoside polyether, the structural formula of which is shown in Formula I),

[0005]

[0006] wherein m is an integer from 1 to 3, n is an integer from 1 to 5, o is an integer from 1 to 3, p is 9 to 18, and R1 is -C 16 H 33 or -C 18 H 37 , R2 is -H or -CH3, R3 is -CH2 or -C2H4.

[0007] The second aspect of the present invention provides a method for preparing the alcohol amino alkyl glycoside polyether according to one aspect of the present invention, which comprises the following steps:

[0008] 1) mixing an alkyl glycoside, an epoxy compound, an inorganic base, and a chloroepoxy compound, and reacting them at a first temperature to obtain a first reaction solution containing a first intermediate product;

[0009] 2) adding triisopropanolamine to the first reaction solution and reacting at a second temperature to obtain a second reaction solution containing a second intermediate product;

[0010] 3) adding polyethylene glycol and an acidic catalyst to the second reaction solution, reacting at a third reaction temperature to obtain a reaction solution containing the alcohol amino alkyl glycoside polyether.

[0011] In a specific embodiment, the alkyl glycoside is hexadecyl glycoside and / or octadecyl glycoside.

[0012] In a specific embodiment, the epoxy compound is ethylene oxide and / or propylene oxide.

[0013] In a specific embodiment, the chlorinated epoxy compound is epichlorohydrin and / or epichlorohydrin.

[0014] In a specific embodiment, the inorganic base is sodium hydroxide and / or potassium hydroxide.

[0015] In a specific embodiment, the polyethylene glycol is at least one of polyethylene glycol 400, polyethylene glycol 600 and polyethylene glycol 800.

[0016] In one embodiment, the acidic catalyst is at least one of concentrated sulfuric acid (eg, 98% concentrated sulfuric acid), aminosulfonic acid, and p-toluenesulfonic acid.

[0017] In a specific embodiment, the mass ratio of the alkyl glycoside, epoxy compound, inorganic base, chloroepoxide, triisopropanolamine, polyethylene glycol and acidic catalyst is 100:(12-18):(5-10):(18-25):(38-48):(80-160):(5-10).

[0018] In one embodiment, the first temperature is 90° C. to 98° C., and the reaction time at the first temperature is 2 to 4 hours.

[0019] In one embodiment, the second temperature is 88° C. to 105° C., and the reaction time at the first temperature is 1 to 3 hours.

[0020] In one embodiment, the third temperature is 116° C. to 124° C., and the reaction time at the first temperature is 1 to 3 hours.

[0021] In one embodiment, the reactions in step 1), step 2) and step 3) are independently stirred at a speed of 600 to 1200 r / min.

[0022] The third aspect of the present invention provides the use of the alcohol amino alkyl glycoside polyether prepared according to the method described in one of the present inventions or any one of the methods described in the second aspect of the present invention for at least one of improving well wall stability, inhibiting collapse and lubricating.

[0023] Beneficial effects of the present invention:

[0024] The alcoholamine-based long-chain alkyl glycoside polyether provided by the present invention has excellent performance in inhibiting the hydration, expansion and dispersion of clay minerals in drilling formations, as well as lubricating and reservoir-protecting properties. It is environmentally friendly and can therefore be used in drilling fluids. Adding alcoholamine-based long-chain alkyl glycoside polyether to drilling fluids effectively addresses the challenges of wellbore instability, drill bit sticking, and reservoir damage in highly water-sensitive shales and other prone-to-collapse formations. The drilling fluid is suitable for green, safe, and efficient drilling operations in deep and ultra-deep wells with temperatures up to 200°C, horizontal shale oil and gas wells, and in environmentally sensitive areas.

[0025] In addition, the present invention uses long-chain alkyl glycoside, epoxy compound, inorganic base, chloroepoxy compound, triisopropanolamine and polyethylene glycol as raw materials, and reacts under the catalysis of an acidic catalyst to obtain alcoholamine-based long-chain alkyl glycoside polyether. The entire reaction conditions are mild, the process operation is simple, no wastewater, waste gas or waste residue is discharged, and the synthetic product is green and environmentally friendly. DETAILED DESCRIPTION

[0026] The present invention will be further described below with reference to examples. However, the examples are merely illustrative and do not limit the present invention in any way.

[0027] Example 1

[0028] 1) adding 200 g of hexadecyl glycoside, 24 g of ethylene oxide, 10 g of sodium hydroxide, and 36 g of epichlorohydrin to a four-necked flask equipped with a condenser reflux device, stirring at 600 r / min and keeping the temperature at 92° C. for 2.0 h to obtain a first reaction solution containing a first intermediate product;

[0029] 2) adding 76 g of triisopropanolamine to the first reaction solution, and reacting at 88° C. for 1.0 h at a stirring speed of 600 r / min to obtain a second reaction solution containing a second intermediate product;

[0030] 3) 160 g of polyethylene glycol 400 was added to the second reaction solution, and the mixture was reacted at 116° C. for 1.0 h at a stirring speed of 600 r / min under the catalysis of 10 g of 98% concentrated sulfuric acid to obtain a light yellow viscous liquid, which was alcohol amino hexadecyl glycoside polyether.

[0031] The product yield was 94.18%.

[0032] The alcohol amino hexadecyl glycoside polyether prepared in Example 1 of the present invention has a structure shown in Formula 1:

[0033]

[0034] In Formula 1, m is an integer of 1 to 3, n is an integer of 1 to 5, o is an integer of 1 to 3, p is an integer of 9 to 10, and R1 is -C 16 H33 , R2 is -H, and R3 is -CH2.

[0035] Example 2

[0036] 1) Add 200 g of octadecyl glycoside, 30 g of propylene oxide, 15 g of potassium hydroxide, and 44 g of epoxychlorobutane to a four-necked flask equipped with a condenser reflux device, and react at 94° C. for 3.0 h at a stirring speed of 1000 r / min to obtain a first reaction solution containing an intermediate product;

[0037] 2) adding 82 g of triisopropanolamine to the first reaction solution, and reacting at 96° C. for 2.0 h at a stirring speed of 1000 r / min to obtain a second reaction solution containing a second intermediate product;

[0038] 3) Add 240 g of polyethylene glycol 600 to the second reaction solution, and react at 120° C. for 2.0 h at a stirring speed of 1000 r / min under the catalysis of 15 g of aminosulfonic acid to obtain a light yellow viscous liquid, which is the alcohol amino octadecyl glycoside polyether.

[0039] The product yield was 95.24%.

[0040] The alcohol amino octadecyl glycoside polyether prepared in Example 2 of the present invention has a structure shown in Formula 2:

[0041]

[0042] In Formula 2, m is an integer from 1 to 3, n is an integer from 1 to 5, o is an integer from 1 to 3, p is an integer from 13 to 15, and R1 is -C 18 H 37 , R2 is -CH3, R3 is -C2H4.

[0043] Example 3

[0044] 1) adding 200 g of hexadecyl glycoside, 36 g of propylene oxide, 20 g of sodium hydroxide, and 50 g of epichlorohydrin to a four-necked flask equipped with a condenser reflux device, stirring at 1200 r / min and keeping the temperature at 98° C. for 4.0 h to obtain a first reaction solution containing a first intermediate product;

[0045] 2) adding 90 g of triisopropanolamine to the first reaction solution, and reacting at 105° C. for 3.0 h at a stirring speed of 1200 r / min to obtain a second reaction solution containing a second intermediate product;

[0046] 3) Add 320 g of polyethylene glycol 800 to the second reaction solution, and react at 124° C. for 3.0 h at a stirring speed of 1200 r / min under the catalysis of 20 g of p-toluenesulfonic acid to obtain a light yellow viscous liquid, which is the alcohol amino hexadecyl glycoside polyether.

[0047] The product yield was 95.73%.

[0048] The alcohol amino hexadecyl glycoside polyether prepared in Example 3 of the present invention has a structure shown in Formula 3:

[0049]

[0050] In Formula 3, m is an integer from 1 to 3, n is an integer from 1 to 5, o is an integer from 1 to 3, p is an integer from 16 to 18, and R1 is -C 16 H 33 , R2 is -CH3, R3 is -CH2.

[0051] Performance measurement

[0052] 1. Evaluation of relative inhibition rate

[0053] Here’s how:

[0054] 1) Take 350mL of distilled water, add 0.5wt% of sodium carbonate, dissolve it, add 10wt% of calcium bentonite, stir at high speed for 20min, and obtain calcium soil-based slurry. The obtained calcium soil-based slurry is hot rolled at 200℃ for 16h, cooled and taken out, stirred at high speed for 5min, and the 100r / min reading of the calcium soil-based slurry is measured by a six-speed rotation viscometer.

[0055] 2) Take 350mL of distilled water, add 0.5wt% of sodium carbonate and 1.0wt% of the alcohol amino long chain alkyl glycoside polyether prepared in Examples 1 to 3 respectively, and after fully dissolving, add 10wt% of calcium bentonite and stir at high speed for 20min to obtain a polyether calcium soil-based slurry. The obtained polyether calcium soil-based slurry is hot rolled at 200°C for 16h, cooled and taken out, stirred at high speed for 5min, and the 100r / min reading of the polyether calcium soil-based slurry is measured by a six-speed rotation viscometer.

[0056] 3) The relative inhibition rate of the alcoholamine-based long-chain alkyl polyglycoside polyether prepared in Examples 1 to 3 on calcium soil-based slurry was calculated as follows:

[0057]

[0058] The calculation results are shown in Table 1.

[0059] 2. Lubrication performance test

[0060] Here’s how:

[0061] 1) The slider in an EP-B extreme pressure lubrication tester (Qingdao Haitongda Special Instrument Co., Ltd.) was immersed in a 1.0 wt % aqueous solution of the alcoholamine-based long-chain alkyl glycoside polyether prepared in Examples 1 to 3 to be tested. The torque wrench value was adjusted to 16.95 N / m. The instrument was operated for 5 minutes, and the value displayed on the instrument was read as X.

[0062] 2) Immerse the slider in the EP-B extreme pressure lubrication instrument (Qingdao Haitongda Special Instrument Co., Ltd.) in clean water, adjust the torque wrench value to 16.95 N / m, operate the instrument for 5 minutes, and read the value Y displayed on the instrument.

[0063] 3) Calculate the extreme pressure lubrication coefficient using the following formula:

[0064]

[0065] The calculation results are shown in Table 1.

[0066] 3. Surface activity test

[0067] Use a surface tension meter to test the surface activity of the product. The method is as follows:

[0068] 1.0% aqueous solutions of the alcoholamine-based long-chain alkyl polyglycoside polyethers prepared in Examples 1 to 3 were prepared respectively. The surface tension of the aqueous solutions was tested at 20° C. using a QBZY series automatic surface tension meter (Shanghai Fangrui Instrument Co., Ltd.) using the platinum white plate method. The results are shown in Table 1.

[0069] 4. Biological toxicity EC 50 Value Test

[0070] Here’s how:

[0071] First, 50000 mg.dm of the alcoholamine long-chain alkyl glycoside polyether prepared in Examples 1 to 3 were prepared using 3 wt% sodium chloride aqueous solution. -3 200 mL of solution was stirred at 12000 r / min for 30 min to fully dissolve. Then a portion of the solution was diluted to 5000 mg.dm -3 、10000mg.dm -3 、25000mg.dm -3 , and finally get 5000mg.dm -3 、10000mg.dm -3 、25000mg.dm -3 、50000mg.dm -3 10 mL of each test solution and add 0 mg.dm -310 mL of the test solution was added and allowed to stand for 60 minutes. 10 mg of Vibrio fischeri T3 powder was added to the test solution at each concentration gradient and thoroughly shaken and mixed. After 15 minutes, the relative luminescence value at each dilution was measured using a DXY-2 biotoxicity tester, and the EC was calculated based on the relative luminescence value at each dilution. 50 The results are shown in Table 1.

[0072] Table 1

[0073] Example Relative inhibition rate / % Extreme pressure lubrication coefficient Surface tension / mN / m <![CDATA[EC 50 Value / mg / L]]> Example 1 98.57 0.0512 23.31 591400 Example 2 98.98 0.0498 22.78 596700 Example 3 99.63 0.0470 22.31 603100

[0074] Although the present invention has been described with reference to specific embodiments, those skilled in the art will appreciate that various modifications may be made without departing from the true spirit and scope of the invention. Furthermore, the subject matter, spirit, and scope of the invention may be modified in various ways to adapt to specific circumstances, materials, combinations of materials, and methods. All such modifications are intended to be within the scope of the claims.

Claims

1. An alcohol amino alkyl glycoside polyether, whose structural formula is shown in Formula I), in, m is an integer from 1 to 3, n is an integer from 1 to 5, o is an integer from 1 to 3, p is 9 to 18, and R1 is -C 16 H 33 or -C 18 H 37 , R2 is -H or -CH3, R3 is -CH2 or -C2H4.

2. A method for preparing the alcohol amino alkyl glycoside polyether according to claim 1, comprising the steps of: 1) mixing an alkyl glycoside, an epoxy compound, an inorganic base, and a chloroepoxy compound, and reacting them at a first temperature to obtain a first reaction solution containing a first intermediate product; 2) adding triisopropanolamine to the first reaction solution and reacting at a second temperature to obtain a second reaction solution containing a second intermediate product; 3) adding polyethylene glycol and an acidic catalyst to the second reaction solution, reacting at a third reaction temperature to obtain a reaction solution containing the alcohol amino alkyl glycoside polyether.

3. The method according to claim 2, characterized in that The alkyl glycoside is hexadecyl glycoside and / or octadecyl glycoside.

4. The method according to claim 2, characterized in that The epoxy compound is ethylene oxide and / or propylene oxide.

5. The method according to claim 2, characterized in that The chlorinated epoxy compound is epichlorohydrin and / or epichlorohydrin.

6. The method according to claim 2, characterized in that The inorganic base is sodium hydroxide and / or potassium hydroxide; and / or The polyethylene glycol is at least one of polyethylene glycol 400, polyethylene glycol 600 and polyethylene glycol 800; and / or The acidic catalyst is at least one of concentrated sulfuric acid, aminosulfonic acid and p-toluenesulfonic acid.

7. The method according to claim 2, characterized in that The mass ratio of the alkyl glycoside, epoxy compound, inorganic base, chloroepoxy compound, triisopropanolamine, polyethylene glycol and acid catalyst is 100:(12-18):(5-10):(18-25):(38-48):(80-160):(5-10).

8. The method according to claim 2, characterized in that The first temperature is 90° C. to 98° C., and the reaction time at the first temperature is 2 to 4 hours; and / or The second temperature is 88° C. to 105° C., and the reaction time at the first temperature is 1 to 3 hours; and / or The third temperature is 116° C. to 124° C., and the reaction time at the first temperature is 1 to 3 hours.

9. The method according to claim 2, characterized in that The reactions in step 1), step 2) and step 3) are independently stirred at a speed of 600 to 1200 r / min.

10. Use of the alcoholamino alkyl glycoside polyether according to claim 1 or the alcoholamino alkyl glycoside polyether prepared by the method according to any one of claims 2 to 9 for at least one of improving wellbore stability, inhibiting collapse, and lubricating.

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