Bio-based alkyl thiophosphoric acid or derivative thereof and preparation method and application of bio-based alkyl thiophosphoric acid or derivative thereof

An alkylthiophosphoric acid, a bio-based technology, applied in the field of machinery or material science, can solve the problems of petrochemical resource loss, complex production process, and poor practical applicability, and achieve the effect of renewable raw materials and environmental friendliness

Inactive Publication Date: 2016-11-23
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The currently reported bio-based oil additives include dispersants, detergents, antioxidants, anti-wear agents and friction modifiers, but there are few practical applications.
The performance of these bio-based additives is inferior to that of petroleum-based additives, the structure is more complicated, the production process is complicated, the performance stability is poor, and the practical applicability is not strong
[0005] Dialkyl dithiophosphate metal salt (ZDDP) has been used in lubricating oil for more than 60 years as an anti-oxidant, anti-wear and anti-corrosion multifunctional additive. It is the most comprehensive multifunctional additive with excellent performance. No additive can completely replace ZDDP
However, the existing ZDDP preparation raw materials are all non-natural or non-renewable substances, and because ZDDP is a consumable product, it causes the loss of petrochemical resources.

Method used

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  • Bio-based alkyl thiophosphoric acid or derivative thereof and preparation method and application of bio-based alkyl thiophosphoric acid or derivative thereof
  • Bio-based alkyl thiophosphoric acid or derivative thereof and preparation method and application of bio-based alkyl thiophosphoric acid or derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1 (comparative example)

[0062] In this example, dodecylphenol is used to synthesize sulfuric acid and its derivatives. Dodecylphenol is alkylated by phenol and tetrapropylene (isododecene) under the catalysis of cation exchange resin or activated clay. be made of.

[0063] Synthesis of thiophosphoric acid: 22.23gP 2 S 5 Put 10.0g of 150N base oil into a reaction bottle, heat to 70°C and stir to disperse, then add 110.1g of dodecylphenol dropwise into the mixture, and control the rate of addition so that the temperature does not exceed 105°C due to the exothermic reaction. After the dropwise addition was completed and the temperature was maintained at 105°C for 1 hour, the temperature was raised to 125°C. After maintaining for 1 hour, purging with nitrogen, the hydrogen sulfide gas in the system was tested negative with lead acetate test paper, and the reaction was completed. After filtration, the phosphoric acid content in the product was 89%, P was 4.3...

Embodiment 2

[0066] In this example, biogenic phenol was used to synthesize phosphoric acid and its derivatives.

[0067] Synthesis of thiophosphoric acid: 22.23gP 2 S 5 Put 10.0g of 150N base oil into a reaction bottle, heat to 70°C and stir to disperse, then add 63.0g of thymol dropwise to the mixture, and control the rate of addition so that the temperature does not exceed 105°C due to the exothermic reaction. After the dropwise addition was completed and the temperature was maintained at 105°C for 1 hour, the temperature was raised to 125°C. After maintaining for 1 hour, purging with nitrogen, the hydrogen sulfide gas in the system was tested negative with lead acetate test paper, and the reaction was completed. After filtration, the phosphoric acid content in the product was 85.7%, P was 6.7%, and S was 13.8%.

[0068] Neutralization reaction: Add 9.13g of ZnO to 30g of 150N base oil and 30g of thymolyl sulfuric acid, stir to disperse. Heat to 45-50°C, add dropwise the remaining 7...

Embodiment 3-10

[0070] Embodiment 3-10 adopts monohydric alcohol of biological origin and its mixture to synthesize phosphoric acid and its derivatives. The synthesis steps are the same as in Example 1 or 2. The specific phosphoric acid synthesis temperature and time vary according to different raw materials. The specific feed ratio is the same as The results are shown in Table 1 and Table 2.

[0071] Table 1

[0072] Example

Types of bio-based alcohols

P 2 S 5 (g)

Alcohol 1 (g)

Alcohol 2 (g)

150N(g)

Thiophosphoric acid%

P％

S％

Example 3

Butanol

22.2

31.1

-

10.0

80.8％

10.3％

21.4％

Example 4

2-butanol

22.2

31.1

-

10.0

80.8％

10.3％

21.4％

Example 5

n-octanol

22.2

54.7

-

10.0

84.9％

7.4％

15.4％

[0073] Example 6

1-pentanol

22.2

37.0

-

10.0

82.1％

9.4％

19.5％

Example 7

sec-butanol, 2-pentanol

22.2

13.8

20....

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PUM

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Abstract

The invention discloses a bio-based alkylthiophosphoric acid or a derivative thereof, a preparation method and an application thereof. This bio-based alkyl phosphorothioate has a structure shown in formula (I): where R 1 , R 2 , at least one of X, Y, Z, W, M from bio-based raw materials; R 1 , R 2 Independently be a hydrocarbon group, a hydroxyl group, a carbonyl group or a heteroatom; and at least one of X, Y, Z, W contains a sulfur atom, and the rest are arbitrarily selected from O, S atoms; and M is H or another one having the formula (I) Derivative groups of molecules of the shown structure. In the synthesis process of the bio-based thiophosphoric acid or its derivatives of the present invention, at least one raw material is derived from bio-based raw materials, that is, natural and renewable raw materials, which have the advantages of greenness, environmental friendliness, renewable raw materials, and energy saving. It can be widely used in the fields of lubricating oil, grease, mine flotation agent, pesticide, flame retardant and rubber accelerator.

Description

technical field [0001] The invention relates to an alkylthiophosphoric acid and its derivatives, in particular to a bio-based alkylthiophosphoric acid or its derivatives, its preparation method and application, and belongs to the field of mechanical or material science. Background technique [0002] With the decreasing of petrochemical resources, the problem of energy shortage and the gradual enhancement of people's awareness of environmental protection, it has gradually become the focus of people's research to replace petrochemicals with bio-renewable resources to the greatest extent, and to apply them to various materials and additives. Bio-based materials use renewable resources as the main raw materials. While reducing the consumption of petrochemical products, they also reduce the environmental pollution during the production process of petroleum-based materials. Bio-based materials refer to a class of new materials that use renewable substances, including crops, trees,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/17C10M137/10C10N30/06C10N30/10C10N30/12
Inventor 冯建湘王志刚刘升高
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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