CN109694388B - Phosphorus-containing compound and preparation method and application thereof - Google Patents

Phosphorus-containing compound and preparation method and application thereof Download PDF

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CN109694388B
CN109694388B CN201710989917.2A CN201710989917A CN109694388B CN 109694388 B CN109694388 B CN 109694388B CN 201710989917 A CN201710989917 A CN 201710989917A CN 109694388 B CN109694388 B CN 109694388B
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CN109694388A (en
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庄敏阳
刘欣阳
孙洪伟
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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China Petroleum and Chemical Corp
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/64—Environmental friendly compositions

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  • General Chemical & Material Sciences (AREA)
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Abstract

The invention provides a phosphorus-containing compound and a preparation method and application thereof. The phosphorus-containing compound of the present invention has the structure:
Figure DDA0001441251460000011
a in the formula I is
Figure DDA0001441251460000012
Or H, at least one A is
Figure DDA0001441251460000013
Wherein R is1Is C2‑C30A hydrocarbon group of R2Is C1‑C10Alkylene of (A), R3Is a single bond or C1‑C10Alkylene of (A), R4Is H or C1‑C6A hydrocarbon group of R5Is C1‑C10Alkylene of (A), R6Is H or C1‑C6A hydrocarbon group of R7Is C1‑C10The alkylene group of (1). The phosphorus-containing compound has excellent biodegradability, and is particularly suitable for promoting biodegradation of lubricating oil products. The preparation method of the phosphorus-containing compound is simple and efficient, and the yield is high.

Description

Phosphorus-containing compound and preparation method and application thereof
Technical Field
The invention relates to a phosphorus-containing compound, in particular to a phosphorus-containing compound capable of promoting biodegradation of lubricating oil.
Background
Lubricating oil is a necessary working medium in the normal operation of mechanical equipment and the manufacturing and processing processes of materials, and along with the rapid development of industry, the demand of the lubricating oil is more and more increased. In the process of storing, transporting and using the lubricating oil, the conditions of leakage, overflow, improper discharge and environmental pollution can not be avoided. Although the acute toxicity of the lubricating oil to organisms is very small, the lubricating oil entering the environment seriously pollutes the land, rivers and lakes due to poor biodegradability, and meanwhile, the ecological balance can be influenced by the accumulation of the lubricating oil in the environment, so that a biodegradation accelerator is urgently needed to improve the biodegradation rate of the lubricating oil.
In recent years, the influence of waste and leaked lubricating oil on the environment has attracted much attention, and in order to solve the problem, on one hand, biodegradable lubricating oil compositions and methods for preparing the same, as reported in CN 102408939B, biodegradable industrial gear oil compositions as reported in CN 105132104a, are prepared from biodegradable vegetable oils and synthetic oils of esters; on the other hand, the development of the lubricating oil biodegradation accelerator is carried out, for example, the chemical formula is C reported in patent CN 103642557B20H37NO3Amide-type lubricating oil biodegradation accelerant, and currently, research reports on the lubricating oil biodegradation accelerant are rare.
Disclosure of Invention
The invention provides a phosphorus-containing compound and a preparation method and application thereof.
The phosphorus-containing compound of the present invention has the structure:
Figure BDA0001441251450000011
a in the formula I is
Figure BDA0001441251450000012
Or H, at least one A is
Figure BDA0001441251450000021
Wherein R is1Is C2-C30Is preferably C5-C25More preferably C8-C20Hydrocarbon group of) R2Is C1-C10Alkylene (preferably C)2-C8Alkylene of (3), more preferably C3-C6Alkylene group of (A), R3Is a single bond or C1-C10Alkylene (preferably a single bond or C)1-C8More preferably a single bond or C1-C4Alkylene group of (A), R4Is H or C1-C6Is preferably H or C1-C4More preferably H or C1-C3Alkyl group of (1), R5Is C1-C10Alkylene (preferably C)1-C8Alkylene of (3), more preferably C1-C6Alkylene group of (A), R6Is H or C1-C6Is preferably H or C1-C4More preferably H or C1-C3Alkyl group of (1), R7Is C1-C10Alkylene (preferably C)1-C8Alkylene of (3), more preferably C1-C6Alkylene groups of (ii).
The R is1Can be selected from C2-C30Optionally C containing one or more unsaturated double bonds2-C30Hydrocarbyl, e.g. C8-C20Alkyl group of (C), CH3(CH2)7CH＝CH(CH2)7-。
The above-mentioned
Figure BDA0001441251450000022
R in (1)5Or R7To the oxygen atom in the repeating unit of formula (I).
The invention also provides a preparation method of the phosphorus-containing compound, which comprises the following steps: will be provided with
Figure BDA0001441251450000023
A step of reacting with a phosphorus source which is a phosphorus compound capable of removing hydroxyl hydrogen to form a bond with hydroxyl oxygen. Wherein each group is as defined above.
The phosphorus source is preferably a phosphorus compound capable of removing hydroxyl hydrogens to form chemical bonds with hydroxyl oxygens.
The phosphorus source is preferably one or more of a phosphorus oxyhalide compound, a phosphorus halide compound, a phosphorus oxyhalide compound, phosphoric acid, phosphorous acid, a phosphoric acid condensate, and a phosphorous acid condensate, and is preferably one or more of a phosphorus oxyhalide compound, a phosphorus halide compound, and a phosphorus oxyhalide compound.
The phosphorus oxygen halogen compound can be one or more of phosphorus oxygen fluorine compound, phosphorus oxygen chlorine compound, phosphorus oxygen bromine compound and phosphorus oxygen iodine compound; the phosphorus halogen compound can be one or more of a phosphorus fluorine compound, a phosphorus chlorine compound, a phosphorus bromine compound and a phosphorus iodine compound; the phosphorus-oxygen compound may be selected from P2O5、P2O3。
Examples of the phosphorus source include POCl3、PCl5、PCl3、P2O5、P2O3、H3PO4、H3PO3。
The phosphorus source is preferably a phosphorus oxychloride compound.
The above-mentioned
Figure BDA0001441251450000031
The reaction equivalent ratio of the phosphorus source to the phosphorus source is 1: 5-5: 1, preferably 1: 3-3: 1. the reaction temperature is 0-50 ℃, preferably 5-45 ℃, and the reaction time is preferably 1-30 hours, more preferably 2-20 hours.
In the above-mentioned
Figure BDA0001441251450000032
The reaction with the phosphorus source may or may not be carried out with a solvent, preferably with a solvent. The solvent is preferably an organic solvent, more preferably an organic polar solvent, and for example, one or more of tetrahydrofuran, dichloromethane, chloroform, acetone, ethyl acetate and acetonitrile may be used, preferably dichloromethane. The amount of the solvent to be added is not particularly limited, as long as the reaction is promoted to proceed smoothly.
The catalyst may or may not be added in the reaction. The catalyst can be organic amine, for example, one or more of ethylamine, diethylamine, triethylamine, n-butylamine and pyridine can be selected, and triethylamine is preferred. The adding amount of the catalyst is preferably 10-700% of the mass of the phosphorus source.
Preference is given to using solvents for the reaction
Figure BDA0001441251450000033
Washing and purifying the product reacted with the phosphorus source, wherein the solvent for washing is preferably a polar organic solvent, for example, one or more of dichloromethane, chloroform, acetone, ethyl acetate and acetonitrile can be selected, and dichloromethane is preferred. The solvent may be removed by conventional techniques such as drying, evaporation, distillation, and the like.
Preferably for the above
Figure BDA0001441251450000041
And (3) carrying out hydrolysis, washing and recrystallization operations on the product reacted with the phosphorus source so as to improve the purity of the reaction product. And the hydrolysis operation is to add water into the reaction product to carry out reflux reaction, wherein the reaction time is preferably 1-6 hours. The washing operation is to perform acid washing and/or water washing operation on the reaction product, preferably, the acid washing is performed firstly, and then the water washing operation is performed, the acid solution in the acid washing operation is preferably an aqueous solution of hydrochloric acid, sulfuric acid or nitric acid, and the concentration of the acid solution is preferably 1-12 mol/L. The recrystallization operation is a step of washing the reaction product with a solvent, followed by recrystallization. The solvent is preferably an alcoholic solvent, more preferably methanol and/or ethanol.
The above-mentioned
Figure BDA0001441251450000042
Preferably by acylation, more preferably by
Figure BDA0001441251450000043
And R1COOH and/or R1And carrying out acylation reaction on the COCl to obtain the product. Wherein each group is as defined above.
The above-mentioned
Figure BDA0001441251450000044
One or more of prolinol, 2-piperidinemethanol, 3-piperidinemethanol, 4-piperidinemethanol, 2-methylaminoethanol, 2-ethylaminoethanol (CAS: 110-73-6), pyrrolidine-3-methanol (CAS: 5082-74-6), and 4-ethylamino-1-butanol can be selected.
The R is1COOH and/or R1Examples of COCl include one or more of lauric acid, myristic acid, palmitic acid, oleic acid, stearic acid, palmitic acid, lauroyl chloride, myristoyl chloride, palmitoyl chloride, oleoyl chloride, stearoyl chloride, and palmitoyl chloride.
The reaction temperature of the acylation reaction is preferably-20-30 ℃, and more preferably-10-20 ℃; the reaction time is preferably 1 to 25 hours, more preferably 2 to 15 hours.
The acylation reaction may be carried out with or without a solvent, preferably with a solvent. The solvent can be selected from polar solvents, for example, one or more of dichloromethane, chloroform, acetone, ethyl acetate, acetonitrile and water can be selected, and a mixture of a polar organic solvent and water is preferred, and the volume ratio of the polar organic solvent to the water is preferably 10: 1-1: 5.
the acylation reaction may or may not be carried out with a catalyst, preferably with a catalyst. The catalyst can be selected from organic base or inorganic base, for example, one or more of lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, triethylamine, pyridine and 4-dimethylamino pyridine can be selected. The amount of the catalyst to be added is preferably an acylating agent (R) used in the acylation reaction1COOH and/or R1COCl) of 50% to 300%, preferably 80% to 200%, by mass.
The phosphorus-containing compound of any of the preceding aspects is useful as a biodegradation agent for lubricating oil products.
The phosphorus-containing compound has excellent biodegradability, and is particularly suitable for promoting biodegradation of lubricating oil products. The preparation method of the phosphorus-containing compound is simple and efficient, and the yield is high.
Detailed Description
The process of the present invention is illustrated below by means of specific examples, but the present invention is not limited thereto.
The experimental methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
EXAMPLE 1 Synthesis of bis (N-lauroyl prolinol) -phosphoric acid (see formula I-a)
Figure BDA0001441251450000051
1) Prolinol (47.6mmol, 4.8g), 40mL acetone, 20mL water, sodium hydroxide (95.2mmol, 10g) were added to the reactor in this order, the temperature was reduced to 0 deg.C, and lauroyl chloride (shown by formula II-a) (47.6mmol, 10.4g) was added dropwise. After 5 hours of reaction, dichloromethane is used for extracting and separating liquid, washing and rotary evaporation are carried out to obtain white solid;
2) dissolving the white solid (17.4mmol, 4.9g) in 50mL dichloromethane, adding triethylamine (52.2mmol, 5.28g), dropwise adding phosphorus oxychloride (8.7mmol, 1.33g), reacting for 12 hours, adding 5mL water, refluxing for 4 hours, washing with 6 mol/L hydrochloric acid solution and water in sequence, drying, rotary evaporating to obtain white solid, and recrystallizing with ethanol to obtain bis (N-lauroyl prolinol) -phosphoric acid (shown in formula I-a).
The structure confirmation results are as follows:1H NMR(400MHz,CDCl3)δ4.47-4.21(m,4H),4.11(br,1H),3.67-3.41(m,6H),2.21(t,J＝6.8Hz,4H),2.12-1.92(m,8H),1.57(t,J＝6.8Hz,4H),1.42-1.21(m,32H),0.81(t,J＝7.0Hz,6H)；HRMS(FT-ICRMS)calcd for C34H64N2O6P(M-H):627.4507,found:627.4511.
the compound synthesized by structural identification is identified as the target compound of bis (N-lauroyl prolinol) -phosphoric acid (shown in a structural formula I-a).
Example 2 Synthesis of bis (N-heptadecaprolinol) -phosphoric acid (see formula I-b)
Figure BDA0001441251450000061
1) Prolinol (47.6mmol, 4.8g), 40mL acetone, 20mL water, sodium hydroxide (95.2mmol, 10g) were added to the reactor in this order, and stearoyl chloride (shown in formula II-b) (47.6mmol, 14.4g) was added dropwise, cooling to 0 ℃. After 5 hours of reaction, the mixture was extracted with dichloromethane, washed with water and rotary evaporated to give a white solid.
2) Dissolving the white solid (17.4mmol, 6.4g) in 50mL dichloromethane, adding triethylamine (52.2mmol, 5.28g), dropwise adding phosphorus oxychloride (8.7mmol, 1.33g), reacting for 12 hours, adding 5mL water, refluxing for 4 hours, washing with 6 mol/L hydrochloric acid solution and water in sequence, drying, rotary evaporating to obtain white solid, and recrystallizing with ethanol to obtain bis (N-heptadecanoyl prolinol) -phosphoric acid (shown in formula I-a).
The structure confirmation results are as follows:1H NMR(400MHz,CDCl3)δ4.55-4.30(m,4H),4.21(br,1H),3.79-3.48(m,6H),2.27(t,J＝6.8Hz,4H),2.20-1.99(m,8H),1.51(t,J＝6.8Hz,4H),1.48-1.23(m,56H),0.88(t,J＝7.0Hz,6H)；HRMS(FT-ICRMS)calcd for C46H88N2O6P(M-H):795.6385,found:795.6387.
the compound synthesized by structure identification is determined to be a target compound, namely bis (N-heptadecaprolinol) -phosphoric acid (shown as a structural formula I-b).
EXAMPLE 3 Synthesis of O-dimethylphosphonyl-N-oleoylserine (see formula I-c)
Figure BDA0001441251450000071
1) Prolinol (47.6mmol, 4.8g), 40mL acetone, 20mL water, sodium hydroxide (95.2mmol, 10g) were added to the reactor in this order, the temperature was reduced to 0 deg.C, and oleoyl chloride (shown in formula II-c) (47.6mmol, 13.45g) was added dropwise. After 5 hours of reaction, the mixture was extracted with dichloromethane, washed with water and rotary evaporated to give a white solid.
2) Dissolving the white solid (17.4mmol, 6.4g) in 50mL dichloromethane, adding triethylamine (52.2mmol, 5.28g), dropwise adding phosphorus oxychloride (8.7mmol, 1.33g), reacting for 12 hours, adding 5mL water, refluxing for 4 hours, washing with 6 mol/L hydrochloric acid solution and water in sequence, drying, rotary evaporating to obtain white solid, and recrystallizing with ethanol to obtain bis (N-oleoyl prolinol) -phosphoric acid (shown in formula I-c).
The structure confirmation results are as follows:1H NMR(400MHz,CDCl3)δ5.76-5.44(m,4H),4.57-4.36(m,4H),4.22(br,1H),3.77-3.42(m,6H),2.21-2.11(m,12H),2.07-1.91(m,8H),1.56(t,J＝7.2Hz,4H),1.48-1.23(m,40H),0.86(t,J＝6.8Hz,6H)；HRMS(FT-ICRMS)calcd for C46H84N2O6P(M-H):791.6072,found:791.6077.
the compound synthesized by structural identification is identified as the target compound bis (N-oleoyl prolinol) -phosphoric acid (shown in structural formula I-c).
Example 4 Synthesis of bis (N-octanoylprolinol) -phosphate (see formula I-d)
Figure BDA0001441251450000072
1) Prolinol (47.6mmol, 4.8g), 40mL acetone, 20mL water, sodium hydroxide (95.2mmol, 10g) were added to the reactor in this order, the temperature was reduced to 0 deg.C, and octanoyl chloride (shown in formula II-d) (47.6mmol, 7.74g) was added dropwise. After 5 hours of reaction, the mixture was extracted with dichloromethane, washed with water and rotary evaporated to give a white solid.
2) Dissolving the white solid (17.4mmol, 4.9g) in 50mL dichloromethane, adding triethylamine (52.2mmol, 5.28g), dropwise adding phosphorus oxychloride (8.7mmol, 1.33g), reacting for 12 hours, adding 5mL water, refluxing for 4 hours, washing with 6 mol/L hydrochloric acid solution and water in sequence, drying, rotary evaporating to obtain white solid, and recrystallizing with ethanol to obtain bis (N-octanoyl prolinol) -phosphoric acid (shown in formula I-d).
The structure confirmation results are as follows:1H NMR(400MHz,CDCl3)δ4.42-4.18(m,4H),4.02(br,1H),3.69-3.44(m,6H),2.25(t,J＝7.0Hz,4H),2.19-1.94(m,8H),1.51(t,J＝7.2Hz,4H),1.44-1.20(m,20H),0.83(t,J＝7.0Hz,6H)；HRMS(FT-ICRMS)calcd for C28H52N2O6P(M-H):543.3568,found:543.3571.
the compound synthesized by structure identification is identified as the target compound of bis (N-caprylyl prolinol) -phosphoric acid (shown in structural formula I-d).
Respectively adding the phosphorus-containing compound prepared in the above way into common lubricating oil HVI 350, PAO4 and PAO10, wherein the mass ratio of the phosphorus-containing compound to the lubricating oil is 1: 99. the biodegradability of phosphorus-containing compounds for lubricating oils was measured according to the OECD 302B method, and the results are shown in Table 1. As is clear from Table 1, the phosphorus-containing compound of the present invention has excellent performance for promoting biodegradation of lubricating oils.
TABLE 1 determination of degradation Properties of lubricating oils
Figure BDA0001441251450000081
Wherein the contrast promoter is derived from the literature: lubrication and sealing, 2009, 34(11), 5-8.

Claims (16)

1. A phosphorus-containing compound having the structure:
Figure FDA0003239531130000011
a in the formula I is
Figure FDA0003239531130000012
Or H, wherein two A are
Figure FDA0003239531130000013
One A is H, wherein R1Is C2-C30A hydrocarbon group of R2Is C1-C10Alkylene of (A), R3Is a single bond or C1-C10Alkylene of (A), R4Is H or C1-C6A hydrocarbon group of R5Is C1-C10The alkylene group of (1).
2. A phosphorus-containing compound according to claim 1, wherein R is1Is C5-C25A hydrocarbon group of R2Is C2-C8Alkylene of (A), R3Is a single bond or C1-C8Alkylene of (A), R4Is H or C1-C4Alkyl of R5Is C1-C8An alkylene group of (a).
3. A phosphorus-containing compound according to claim 1, wherein R is1Is C8-C20A hydrocarbon group of R2Is C3-C6Alkylene of (A), R3Is a single bond or C1-C4Alkylene of (A), R4Is H or C1-C3Alkyl of R5Is C1-C6An alkylene group of (a).
4. A method of preparing a phosphorus-containing compound comprising: will be provided with
Figure FDA0003239531130000014
A step of reacting with a phosphorus source, wherein R1Is C2-C30A hydrocarbon group of R2Is C1-C10Alkylene of (A), R3Is a single bond or C1-C10Alkylene of (A), R4Is H or C1-C6A hydrocarbon group of R5Is C1-C10The alkylene group of (1).
5. A process according to claim 4, wherein the phosphorus source is a phosphorus compound capable of removing hydroxyl hydrogens to form a chemical bond with hydroxyl oxygen, R1Is C5-C25A hydrocarbon group of R2Is C2-C8Alkylene of (A), R3Is a single bond or C1-C8Alkylene of (A), R4Is H or C1-C4Alkyl of R5Is C1-C8An alkylene group of (a).
6. The method of claim 4, wherein R is1Is C8-C20A hydrocarbon group of R2Is C3-C6Alkylene of (A), R3Is a single bond or C1-C4Alkylene of (A), R4Is H or C1-C3Alkyl of R5Is C1-C6An alkylene group of (a).
7. The method of claim 4, wherein the phosphorus source is selected from one or more of phosphorus oxyhalide compounds, phosphorus halide compounds, phosphorus oxy compounds, phosphoric acid, phosphorous acid, phosphoric acid condensates, and phosphorous acid condensates.
8. The method of claim 4, wherein the phosphorus source is selected from one or more of phosphorus oxyhalide compounds, phosphorus halide compounds, and phosphorus oxyhalide compounds.
9. The method of claim 7, wherein the phosphorus oxyhalide compound is selected from one or more of a phosphorus oxyfluoride compound, a phosphorus oxychloride compound, a phosphorus oxybromide compound, and a phosphorus oxyiodide compound; the phosphorus halogen compound is selected from one or more of a phosphorus fluorine compound, a phosphorus chlorine compound, a phosphorus bromine compound and a phosphorus iodine compound; the phosphorus oxygen compound is selected from P2O5And/or P2O3。
10. Method according to claim 4, characterized in that said method comprises
Figure FDA0003239531130000021
The reaction equivalent ratio of the phosphorus source to the phosphorus source is 1: 5-5: 1, the reaction temperature is 0-50 ℃, and the reaction time is 1-30 hours.
11. Method according to claim 4, characterized in that said method comprises
Figure FDA0003239531130000022
The reaction equivalent ratio of the phosphorus source to the phosphorus source is 1: 3-3: 1, the reaction temperature is 5-45 ℃, and the reaction time is 2-20 hours.
12. The method of claim 4, wherein a catalyst is added to the reaction, and the catalyst is an organic amine.
13. Method according to claim 4, characterized in that said method comprises
Figure FDA0003239531130000023
Obtained by acylation reaction.
14. Method according to claim 4, characterized in that said method comprises
Figure FDA0003239531130000024
By passing
Figure FDA0003239531130000031
And R1COOH and/or R1And carrying out acylation reaction on the COCl to obtain the product.
15. The method of claim 14, wherein said method further comprises
Figure FDA0003239531130000032
One or more selected from prolinol, 2-piperidinemethanol, 3-piperidinemethanol, 4-piperidinemethanol and pyrrolidine-3-methanol.
16. Use of a phosphorus-containing compound according to any one of claims 1 to 3 or obtained by a process according to any one of claims 4 to 15 as a biodegradation agent for lubricating oil products.
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