CN110698329A - Biomass synthetic oil for drilling fluid and preparation method thereof - Google Patents

Biomass synthetic oil for drilling fluid and preparation method thereof Download PDF

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Publication number
CN110698329A
CN110698329A CN201810744419.6A CN201810744419A CN110698329A CN 110698329 A CN110698329 A CN 110698329A CN 201810744419 A CN201810744419 A CN 201810744419A CN 110698329 A CN110698329 A CN 110698329A
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drilling fluid
synthetic oil
biomass synthetic
prepared
biomass
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单海霞
王中华
周亚贤
李彬
张晓刚
吕跃滨
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Sinopec Oilfield Service Corp
Sinopec Zhongyuan Petroleum Engineering Co Ltd
Drilling Engineering Technology Research Institute of Sinopec Zhongyuan Petroleum Engineering Co Ltd
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Sinopec Oilfield Service Corp
Sinopec Zhongyuan Petroleum Engineering Co Ltd
Drilling Engineering Technology Research Institute of Sinopec Zhongyuan Petroleum Engineering Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01Preparation of ethers
    • C07C41/16Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02Well-drilling compositions
    • C09K8/32Non-aqueous well-drilling compositions, e.g. oil-based
    • C09K8/34Organic liquids

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  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides a preparation method of biomass synthetic oil for drilling fluid, which comprises the following steps: reacting halogenated dodecane, an acid-binding agent and alkyl alcohol under the action of a catalyst to obtain the biomass synthetic oil for the drilling fluid. The method for preparing the biomass synthetic oil for the drilling fluid has the advantages of low synthesis temperature, short synthesis time, high synthesis efficiency, time and cost saving, high reaction yield, good product quality, simple process, mild conditions, no toxicity, high efficiency and environmental protection in the preparation process, and can effectively avoid the generation of waste gas in the industrial production process. The invention also provides the biomass synthetic oil for the drilling fluid, which is prepared by the method in the technical scheme, has good inhibition, low viscosity, strong temperature resistance, hydrolytic stability and biodegradability, and can be used as base oil for synthesizing the drilling fluid.

Description

Biomass synthetic oil for drilling fluid and preparation method thereof
Technical Field
The invention relates to the technical field of synthetic oil, in particular to biomass synthetic oil for well drilling and a preparation method thereof.
Background
The base oil is the main component for preparing the drilling fluid, and the performance indexes of the base oil determine the vast majority of performance indexes of the drilling fluid, such as flash point, viscosity, freezing point, biological toxicity and the like. Along with the increasing number of deep well, ultra-deep well, horizontal well and large-slope directional well encountered by drilling, the probability of drilling in a strong water-sensitive stratum is higher and higher, and the synthetic base drilling fluid is widely applied due to excellent lubricating, inhibiting and other properties. However, the base oil used for preparing the synthetic base drilling fluid at present is mainly chemical products such as mineral oil, olefin, alkylbenzene, linear paraffin and the like, has the defects of certain toxicity and poor biodegradability, and has been limited to be applied to some environment sensitive areas. With the increasingly strict national environmental protection requirements, the development of environment-friendly drilling fluid and green drilling fluid base oil become the main directions of research and application in the field.
Therefore, there is a need for a biodegradable base oil with good drilling fluid performance indexes such as inhibitive performance, viscosity, temperature resistance, and hydrolytic stability.
Disclosure of Invention
In view of the above, the invention aims to provide the biomass synthetic oil for the drilling fluid and the preparation method thereof.
The invention provides a preparation method of biomass synthetic oil for drilling fluid, which comprises the following steps:
under the action of a catalyst, chlorododecane, an acid-binding agent and alkyl alcohol react to obtain the biomass synthetic oil for the drilling fluid.
In the invention, the alkyl alcohol is preferably an alkyl alcohol with 1-10 carbon atoms, and more preferably one or more of methanol, ethanol, butanol, isobutanol, n-hexanol and n-octanol.
In the present invention, the halogenated dodecane is preferably one or more of chlorododecane and bromododecane.
In the present invention, the catalyst is preferably selected from one or more of sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium methoxide, potassium ethoxide and potassium tert-butoxide.
In the invention, the acid-binding agent is preferably one or two of sodium carbonate and potassium carbonate.
In the present invention, the molar ratio of the halogenated dodecane, the acid scavenger, the alkyl alcohol and the catalyst is preferably 1: (1.1-1.3) in the following ratio (1.1-1.3): (0.02 to 0.05), more preferably 1: (1.15-1.25) and (1.15-1.25): (0.03-0.04), most preferably 1: 1.2:1.2: 0.035.
in the invention, the reaction temperature is preferably 60-100 ℃, more preferably 70-90 ℃, and most preferably 75-85 ℃; the reaction time is preferably 6 to 10 hours, more preferably 7 to 9 hours, and most preferably 8 hours. In the present invention, the reaction is preferably carried out under stirring conditions, and the stirring speed is preferably 200 to 300rpm, more preferably 220 to 280rpm, and most preferably 240 to 260 rpm.
The method for preparing the biomass synthetic oil adopts nucleophilic substitution reaction, for alkylated lauryl alcohol, the activity of anions, namely dodecyl oxygen anions, of the method is far greater than that of the lauryl alcohol, and halogenated dodecane can rapidly generate dodecyl ether with alkyl alcohol after an alkaline catalyst and an acid-binding agent are added into a reaction system. Therefore, the method provided by the invention has the advantages of shorter time for preparing the biomass synthetic oil and higher production efficiency; in addition, the method provided by the invention has the advantages of mild reaction conditions, high reactant activity, low required temperature and high conversion speed; can avoid the occurrence of side reaction and has high product yield.
The biomass synthetic oil for the drilling fluid prepared by the method provided by the invention has better inhibitive performance, viscosity, temperature resistance, hydrolytic stability and biodegradability, and the biomass synthetic oil for the drilling fluid prepared by the method provided by the invention has the advantages of low reaction temperature, short reaction time, capability of avoiding industrial waste gas generation in the large-scale production process, high synthesis efficiency and time and cost saving. The method for preparing the biomass synthetic oil for the drilling fluid has the advantages of high reaction yield, good product quality, simple process method, mild conditions, and nontoxic, efficient and environment-friendly preparation process.
The preparation method of the biomass synthetic oil provided by the invention has the advantages of mild synthesis conditions, simple process and no secondary pollution, and the prepared product has good environmental protection characteristics, good safety performance and easy biodegradation, and can meet the requirements of being used as base oil of drilling fluid.
The invention provides biomass synthetic oil for drilling fluid, which is prepared by the method in the technical scheme. In the invention, the biomass synthetic oil for the drilling fluid preferably has a structure shown in a formula I:
Figure BDA0001723977630000021
in the formula I, R is an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 2 to 8 carbon atoms, more preferably an alkyl group having 36 to 9 carbon atoms, and most preferably an alkyl group having 4 to 5 carbon atoms.
In the invention, the biomass synthetic oil for the drilling fluid is preferably dodecyl methyl ether, dodecyl ethyl ether, dodecyl butyl ether, dodecyl hexyl ether or dodecyl decyl ether. In the invention, the number average molecular weight of the biomass synthetic oil for the drilling fluid is preferably 200-326, the lubrication coefficient is preferably 0.04-0.08, and the kinematic viscosity at 40 ℃ is preferably 1.8-2.8 mm2S, appearance is preferably colorless and transparent orA light yellow transparent liquid.
The biomass synthetic oil for the drilling fluid, which is prepared by the method, structurally comprises saturated long-chain fatty groups and alkyl ether groups, does not contain unsaturated bonds (such as ester bonds and carbon-carbon double bonds), and has good inhibition, viscosity, temperature resistance, hydrolytic stability and biodegradability.
In the invention, the biomass synthetic oil for the drilling fluid is a green and nontoxic product, has no stimulation to human bodies and environment after being decomposed, has good ecological safety, has good lubricity and biocompatibility, and can meet the performance requirement of being used as base oil of the drilling fluid.
The biomass synthetic oil for the drilling fluid is a light yellow liquid, is a low-viscosity asymmetric high-grade ether synthesized by alkyl etherification modification, does not contain unsaturated bonds (ester bonds and carbon-carbon double bonds) in the structure, has high temperature resistance and hydrolytic stability, and can be used as base oil of the drilling fluid.
The biomass synthetic oil for the drilling fluid can be used for the drilling fluid and used as base oil of the drilling fluid, so that the drilling fluid has better inhibitive performance, viscosity, temperature resistance, hydrolytic stability and biodegradability. The biomass synthetic oil provided by the invention has good chemical stability, lubricity, inhibitability, low viscosity, hydrolytic stability and biodegradability as the base oil of the drilling fluid, has the advantage that the viscosity of an ether base fluid is less influenced by temperature change, and has good chemical stability, lubricity, inhibitability, low viscosity and hydrolytic stability.
According to the national standard GB/T16783.2' petroleum and natural gas industry drilling fluid field test part 2: oil-based drilling fluid, the molecular weight, the lubrication coefficient and the kinematic viscosity at 40 ℃ of the biomass synthetic oil prepared by the invention are tested. The biotoxicity of the biomass synthetic oil prepared by the invention is tested by an acute oral toxicity method in the disinfection technical Specification of the Ministry of health (2002 edition).
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In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the provided drawings without creative efforts.
FIG. 1 is a gas chromatogram of a biomass synthetic oil prepared in example 1 of the present invention;
FIG. 2 is a gas chromatogram of the biomass synthetic oil prepared in example 2 of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other examples, which may be modified or appreciated by those of ordinary skill in the art based on the examples given herein, are intended to be within the scope of the present invention.
The raw materials used in the following examples of the present invention are all commercially available products.
Example 1
Adding 1mol of chlorododecane, 1.1mol of sodium carbonate, 1.1mol of methanol and 0.02mol of sodium tert-butoxide into a reaction kettle with a stirring, condensing and heating device, stirring and mixing uniformly, reacting for 6 hours at 60 ℃ and 200rpm, and cooling to room temperature to obtain the biomass synthetic oil.
Performing gas chromatography detection on the biomass synthetic oil prepared in the embodiment 1 of the invention, wherein a detection instrument is a gas chromatograph of Fuli analytical instruments ltd, Wenling City, and the model of the instrument is GC-9700; the gas phase detection conditions were: the chromatographic column comprises SE-54(30m × 0.32mm × 0.25 μm), column temperature of 190 deg.C, injection port temperature of 300 deg.C, detection temperature (FID) of 300 deg.C, flow rate of carrier gas (nitrogen gas) of 30mL/min, sample injection amount of 0.2 μ L, and split ratio of 50: 1. As shown in FIG. 1, a peak appeared at 3.715min, and the peak area content was 92.39%. Through detection, the product prepared in the embodiment 1 of the invention is dodecyl methyl ether and has a structure shown in a formula I, wherein R is methyl.
The dodecyl methyl ether prepared in the embodiment 1 of the invention is colorless and transparent liquid in appearance, and the yield is 83.5%. According to the method of the technical scheme, the molecular weight, the lubrication coefficient and the kinematic viscosity of the lauryl methyl ether prepared in the embodiment 1 of the invention are detected, the detection results are shown in table 1, and the table 1 is the performance detection results of the biomass synthetic oil prepared in the embodiment of the invention.
Example 2
Adding 1mol of chlorododecane, 1.3mol of potassium carbonate, 1.1mol of butanol and 0.03mol of sodium ethoxide into a reaction kettle with a stirring, condensing and heating device, stirring and mixing uniformly, reacting for 8 hours at 80 ℃ and 250rpm, and cooling to room temperature to obtain the biomass synthetic oil.
According to the method of example 1, the biomass synthetic oil prepared in example 2 of the present invention was subjected to gas chromatography detection under the same conditions as in example 1, and the detection result is shown in FIG. 2, in which a peak appeared at 5.773min and the peak area content was 93.99%. Through detection, the product prepared in the embodiment 2 of the invention is dodecyl butyl ether and has a structure shown in a formula I, wherein R is butyl.
According to the method of the technical scheme, the dodecyl butyl ether prepared in the embodiment 2 of the invention is subjected to detection of molecular weight, lubrication coefficient and kinematic viscosity, and the detection results are shown in table 1.
Example 3
Adding 1mol of bromododecane, 1.3mol of potassium carbonate, 1.1mol of ethanol and 0.05mol of sodium methoxide into a reaction kettle with a stirring, condensing and heating device, stirring and mixing uniformly, reacting for 10 hours at 100 ℃ and 300rpm, and cooling to room temperature to obtain the biomass synthetic oil.
According to the method of the embodiment 1, the biomass synthetic oil prepared in the embodiment 3 of the invention is detected by gas chromatography, and the detection result is dodecyl ethyl ether with the structure shown in the formula I, wherein R is ethyl.
According to the method of the technical scheme, the dodecyl ethyl ether prepared in the embodiment 3 of the invention is subjected to detection of molecular weight, lubrication coefficient and kinematic viscosity, and the detection results are shown in table 1.
Example 4
Adding 1mol of chlorododecane, 1.1mol of sodium carbonate, 1.1mol of n-hexanol and 0.04mol of potassium tert-butoxide into a reaction kettle with a stirring, condensing and heating device, stirring and mixing uniformly, reacting for 10 hours at 90 ℃ and 280rpm, and cooling to room temperature to obtain the biomass synthetic oil.
According to the method of the embodiment 1, the biomass synthetic oil prepared in the embodiment 4 of the invention is detected by gas chromatography, and the detection result is dodecyl hexyl ether with the structure shown in the formula I, wherein R is hexyl.
According to the method of the technical scheme, the molecular weight, the lubrication coefficient and the kinematic viscosity of the dodecyl hexyl ether prepared in the embodiment 4 of the invention are detected, and the detection results are shown in table 1.
Example 5
Adding 1mol of bromododecane, 1.3mol of potassium carbonate, 1.3mol of octanol and 0.05mol of potassium methoxide into a reaction kettle with a stirring, condensing and heating device, stirring and mixing uniformly, reacting for 9 hours at the temperature of 95 ℃ and the speed of 260rpm, and cooling to room temperature to obtain the biomass synthetic oil.
According to the method of the embodiment 1, the biomass synthetic oil prepared in the embodiment 5 of the invention is detected by gas chromatography, and the detection result is dodecyl octyl ether with the structure shown in the formula I, wherein R is octyl.
According to the method of the technical scheme, the molecular weight, the lubrication coefficient and the kinematic viscosity of the dodecyl octyl ether prepared in the embodiment 5 of the invention are detected, and the detection results are shown in table 1.
Example 6
Adding 1mol of chlorododecane, 1.2mol of sodium carbonate, 1.2mol of decanol and 0.03mol of potassium ethoxide into a reaction kettle with a stirring, condensing and heating device, stirring and mixing uniformly, reacting for 10 hours at 85 ℃ and 270rpm, and cooling to room temperature to obtain the biomass synthetic oil.
According to the method of the embodiment 1, the biomass synthetic oil prepared in the embodiment 6 of the invention is detected by gas chromatography, and the detection result is dodecyl decyl ether with the structure shown in the formula I, wherein R is decyl.
According to the method of the technical scheme, the molecular weight, the lubrication coefficient and the kinematic viscosity of the dodecyl decyl ether prepared in the embodiment 6 of the invention are detected, and the detection results are shown in table 1.
Example 7
Adding 1mol of chlorododecane, 1.1mol of potassium carbonate, 1.1mol of butanol and 0.03mol of potassium tert-butoxide into a reaction kettle with a stirring, condensing and heating device, stirring and mixing uniformly, reacting for 7 hours at 70 ℃ and 220rpm, and cooling to room temperature to obtain the biomass synthetic oil.
According to the method of the embodiment 1, the biomass synthetic oil prepared in the embodiment 7 of the invention is detected by gas chromatography, and the detection result is dodecyl butyl ether with the structure shown in the formula I, wherein R is butyl.
According to the method of the technical scheme, the dodecyl butyl ether prepared in the embodiment 7 of the invention is subjected to detection of molecular weight, lubrication coefficient and kinematic viscosity, and the detection results are shown in table 1.
Example 8
Adding 1mol of bromododecane, 1.2mol of potassium carbonate, 1.2mol of butanol and 0.04mol of sodium tert-butoxide into a reaction kettle with a stirring, condensing and heating device, stirring and mixing uniformly, reacting for 8 hours at 90 ℃ and 250rpm, and cooling to room temperature to obtain the biomass synthetic oil.
According to the method of the embodiment 1, the biomass synthetic oil prepared in the embodiment 8 of the invention is detected by gas chromatography, and the detection result is dodecyl butyl ether with the structure shown in the formula I, wherein R is butyl.
According to the method of the technical scheme, the dodecyl butyl ether prepared in the embodiment 8 of the invention is subjected to detection of molecular weight, lubrication coefficient and kinematic viscosity, and the detection results are shown in table 1.
Example 9
Adding 1mol of chlorododecane, 1.1mol of potassium carbonate, 1.2mol of ethanol and 0.03mol of potassium tert-butoxide into a reaction kettle with a stirring, condensing and heating device, stirring and mixing uniformly, reacting for 6 hours at 100 ℃ and 200rpm, and cooling to room temperature to obtain the biomass synthetic oil.
According to the method of the embodiment 1, the biomass synthetic oil prepared in the embodiment 9 of the invention is detected by gas chromatography, and the detection result is dodecyl ethyl ether with the structure shown in the formula I, wherein R is ethyl.
According to the method of the technical scheme, the dodecyl ethyl ether prepared in the embodiment 9 of the invention is subjected to detection of molecular weight, lubrication coefficient and kinematic viscosity, and the detection results are shown in table 1.
TABLE 1 Performance data for Biomass synthetic oils prepared in accordance with the present invention
Figure BDA0001723977630000071
Example 10
The biomass synthetic oil prepared by the embodiment of the invention is used as a base fluid to prepare the drilling fluid, and the prepared drilling fluid comprises: 100 parts by weight of a biomass synthetic oil; 3 parts by weight of quaternary ammonium salt modified organic soil; 5 parts by weight of span-80; 4 parts by weight of an oil-soluble epoxy resin; 3 parts by weight of calcium oxide and 133 parts by weight of barite. Aging the drilling fluid at 150 ℃, and then performing performance test according to the national standard GB/T16783.2-2012, the 2 nd part of the field test of the drilling fluid in the petroleum and natural gas industry: the method of oil-based drilling fluid "was used to test the performance of the drilling fluid, and the test results are shown in table 2, where table 2 is the performance test results of the drilling fluid prepared according to the example of the present invention.
Table 2 performance test results for drilling fluids prepared according to embodiments of the present invention
Figure BDA0001723977630000072
Note: rho is density; AV is apparent viscosity; PV is plastic viscosity; YP is dynamic shear force.
As can be seen from Table 2, in terms of service performance, the drilling fluid prepared from the biomass synthetic oil provided by the invention has the density of 1.6g/cm at the temperature of 150 DEG C3Within the range, the apparent viscosity is less than 80mPa · s, and the filtration loss is less than 0.5 mL; the drilling fluid disclosed by the invention has good rheological property and suspension stability, and can meet the requirements of exploration and development. Moreover, the drilling fluid is green and environment-friendly.
From the above embodiments, the present invention provides a method for preparing a biomass synthetic oil for a drilling fluid, including: reacting halogenated dodecane, an acid-binding agent and alkyl alcohol under the action of a catalyst to obtain the biomass synthetic oil for the drilling fluid. The method for preparing the biomass synthetic oil for the drilling fluid has the advantages of low synthesis temperature, short synthesis time, high synthesis efficiency, time and cost saving, high reaction yield, good product quality, simple process, mild conditions, no toxicity, high efficiency and environmental protection in the preparation process, and can effectively avoid the generation of waste gas in the industrial production process. The invention also provides the biomass synthetic oil for the drilling fluid, which is prepared by the method in the technical scheme, has good inhibition, low viscosity, strong temperature resistance, hydrolytic stability and biodegradability, and can be used as base oil for synthesizing the drilling fluid.
While only the preferred embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention.

Claims (10)

1. A preparation method of biomass synthetic oil for drilling fluid comprises the following steps:
reacting halogenated dodecane, an acid-binding agent and alkyl alcohol under the action of a catalyst to obtain the biomass synthetic oil for the drilling fluid.
2. The method of claim 1, wherein the halogenated dodecane is one or more of chlorododecane and bromododecane.
3. The method according to claim 1, wherein the catalyst is selected from one or more of sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium methoxide, potassium ethoxide and potassium tert-butoxide.
4. The method of claim 1, wherein the acid scavenger is one or both of sodium carbonate and potassium carbonate.
5. The method according to claim 1, wherein the alkyl alcohol has 1 to 10 carbon atoms.
6. The method according to claim 5, wherein the alkyl alcohol is selected from one or more of methanol, ethanol, butanol, isobutanol, n-hexanol, n-octanol and decanol.
7. The process according to claim 1, wherein the molar ratio of the halododecane, acid scavenger, alkyl alcohol and catalyst is 1: (1.1-1.3), (0.02-0.05).
8. The method according to claim 1, wherein the reaction time is 6 to 10 hours.
9. The method according to claim 1, wherein the reaction temperature is 60 to 100 ℃.
10. The biomass synthetic oil for the drilling fluid prepared by the method of claim 1.
CN201810744419.6A 2018-07-09 2018-07-09 Biomass synthetic oil for drilling fluid and preparation method thereof Pending CN110698329A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1070938A (en) * 1991-08-16 1993-04-14 埃克森化学专利公司 Load bearing fluid
US20130074398A1 (en) * 2010-05-30 2013-03-28 Theis Brock-Nannestad Aviation fuel
CN104788296A (en) * 2014-09-22 2015-07-22 山东诚创医药技术开发有限公司 Preparation method of methyldecane as impurity of colesevelam hydrochloride
CN107304160A (en) * 2016-04-18 2017-10-31 中石化石油工程技术服务有限公司 A kind of biomass alcohol ether and preparation method thereof and drilling fluid
CN107304161A (en) * 2016-04-18 2017-10-31 中石化石油工程技术服务有限公司 A kind of laruyl alcohol alkyl ether and preparation method thereof and drilling fluid

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1070938A (en) * 1991-08-16 1993-04-14 埃克森化学专利公司 Load bearing fluid
US20130074398A1 (en) * 2010-05-30 2013-03-28 Theis Brock-Nannestad Aviation fuel
CN104788296A (en) * 2014-09-22 2015-07-22 山东诚创医药技术开发有限公司 Preparation method of methyldecane as impurity of colesevelam hydrochloride
CN107304160A (en) * 2016-04-18 2017-10-31 中石化石油工程技术服务有限公司 A kind of biomass alcohol ether and preparation method thereof and drilling fluid
CN107304161A (en) * 2016-04-18 2017-10-31 中石化石油工程技术服务有限公司 A kind of laruyl alcohol alkyl ether and preparation method thereof and drilling fluid

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