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Application of alkyl sulfide methyl phenolic compounds

A technology of alkylthiomethylphenol and alkylthiomethyl, which is applied in the fields of sulfide preparation, organic chemistry, liquid carbon-containing fuel, etc., can solve the problem of no antiknock effect of metal antiknock agents, air and soil environmental damage , Interfering with metabolism and other issues, to achieve excellent anti-knock performance, no ash, no residue and environmental protection

Inactive Publication Date: 2011-08-17
邱国福
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As we all know, lead-containing antiknock agents are highly toxic substances, which not only cause great harm to the human body, such as loss of appetite, physical drowsiness, visual hallucinations, auditory hallucinations, coma, and even death; the product of combustion, lead dioxide, can cause neurotoxicity, Interfering with metabolism, poisoning the purification device of the exhaust system of the engine, invalidating various sensors of the EFI device, etc., more importantly, causing irreversible damage to the air and soil environment
The addition of ferrocene to gasoline has a good anti-shock effect, but due to the bad influence of iron oxide deposition on engine and exhaust and other auxiliary equipment oils, although additives can be added to reduce iron oxide deposition, the additive itself also has shortcomings. while driving up costs
However, MMT forms porous deposits on the surface of the engine combustion chamber, which is likely to cause an increase in the manganese content in the environment; at the same time, it is harmful to the exhaust system
Although MMT has many shortcomings, it is after all an efficient antiknock agent developed after alkyl lead, and it is still used in Europe and Asia with restrictions
[0005] 2 Organic ashless: Organic antiknock agents are low in cost and widely sourced, but they are not as effective as metal antiknock agents. The increase in octane number is quite limited, and the dosage is relatively large (15% or even higher). Can only be used in combination with metal antiknock agents
But recently, MTBE's environmental pollution and refractory problems have caused more and more concerns in relevant countries and regions

Method used

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  • Application of alkyl sulfide methyl phenolic compounds
  • Application of alkyl sulfide methyl phenolic compounds
  • Application of alkyl sulfide methyl phenolic compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Under stirring at 0-10℃, add 108.1g (1.0 mol) o-cresol, 124.1g (2.0 mol) ethyl mercaptan, and 120.1g paraformaldehyde (4.0 mol) to a 1-liter autoclave in turn, and then slowly Slowly add 27.33g of 33% (volume ratio) dimethylamine aqueous solution. After the dimethylamine solution is added, the reactor is sealed under the condition of nitrogen gas. Under the protection of nitrogen and stirring, let the reaction solution react at 50°C for 1.5 hours, then heat to 115°C for 2 hours; lower the temperature of the reaction solution to 20°C, distill under reduced pressure to remove water and low-boiling organic impurities, and then Slowly increase the temperature of the reaction solution to 95°C, and distill out most of the volatile impurities and intermediate products. Finally at Under the condition of 1 HNMR, CDCl3, ppm): 1.3011-1.3102 (6H, t, 2*CH 3 ), 2.2690 (3H, s, ArCH 3 ), 2.3911-2.4302 (4H, q, 2* SCH 2 ), 3.6055 (2H, s, SCH 2 Ar), 3.9667 (2H, s, SCH 2 Ar), 6.8642-6.8687...

Embodiment 2

[0034] Under stirring at 0-10°C, 108.14g (1.0 mol) o-cresol, 152g (2.0 mol) n-propyl mercaptan, 120.12g paraformaldehyde (4.0 mol) were added to a 1-liter autoclave in sequence, and then dropped Add 27.33g of 33% dimethylamine in water. After the dimethylamine solution is added, the reactor is sealed. Under the protection of nitrogen and stirring, let the reaction solution react at 50°C for 0.5 hours, then heat to 115°C for 2 hours; reduce the temperature of the reaction solution to 65°C, and distill under reduced pressure to remove water and low-boiling organic impurities , Then slowly increase the temperature of the reaction solution to 95°C, and distill out most of the volatile impurities and intermediate products. Finally at Under the condition of 1 HNMR, CDCl3, ppm): 1.103-1.126 (6H, t, 2*CH 3 ), 1.6890-1.6907 (4H, m, 2* CH 2 ), 2.2667 (3H, s, ArCH 3 ), 2.3685-2.4431 (4H, q, 2* SCH 2 ), 3.6051 (2H, s, SCH 2 Ar), 3.9648 (2H, s, SCH 2 Ar), 6.8638-6.8681 (1H, d, Ar-H), 7.028...

Embodiment 3

[0036] Under stirring at 0-10℃, add 108.14g (1.0 mol) o-cresol, 180g (2.0 mol) isopropyl mercaptan, and 120.12g paraformaldehyde (4.0 mol) into a 1 liter autoclave. 27.33g of 33% dimethylamine aqueous solution was added dropwise. After the dimethylamine solution is added, the reactor is sealed. The subsequent control, operation and reaction post-treatment process are the same as in the second implementation example. Then 225.7 g (79.5%) of 2-methyl-4,6-bis(isopropylthiomethyl)phenol was obtained. (Sample number 03). Proton Nuclear Magnetic Resonance Spectroscopy ( 1 HNMR, CDCl3, ppm): 1.2784-1.2951 (12H, d, 4*CH 3 ), 2.2662 (3H, s, ArCH 3 ), 2.3690-2.4424 (2H, q, 2* SCH), 3.6027 (2H, s, SCH 2 Ar), 3.9639 (2H, s, SCH 2 Ar), 6.8647-6.8686 (1H, d, Ar-H), 7.0285-7.0319 (1H, d, Ar-H), 7.489 (1H, b, OH).

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Abstract

The invention relates to efficient antiknock active compounds capable of remarkably increasing the octane value of fuel oil, wherein antiknock effective components are alkyl sulfide methyl phenolic compounds which can increase the octane value of the fuel oil by 1-25, not only have excellent antiknock performance same as metal antiknock agents, but also have the advantages of no dust and no residual of an organic antiknock agent. The alkyl sulfide methyl phenolic compounds have a structural formula shown in the specification, wherein R1 is hydrogen, methyl, ethyl or isopropyl; R2 is C1-12 linear alkyl or C1-12 branched alkyl or C3-5 alkenyl; and n=1-3.

Description

Technical field [0001] The invention relates to the use of alkyl thiomethyl phenol compounds, in particular to the use of alkyl thiomethyl phenol compounds as fuel antiknock agents, and belongs to the field of fuel additives. Background technique [0002] It is the consistent pursuit of the automotive fuel production industry to achieve combustion at a high compression ratio, improve fuel combustion efficiency, and obtain greater power. Especially in today's increasingly serious energy crisis, the combustion efficiency of internal combustion engines is an important way to save energy and reduce emissions. For vehicle engines that consume a lot of gasoline, increasing the octane number of gasoline and achieving combustion under high compression ratio conditions is one of the effective ways to improve combustion efficiency, enhance engine power, and achieve energy saving and emission reduction. This requires vehicle fuel to have a high octane number, so that it has good anti-knock...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C10L10/10C10L1/24C07C323/20
Inventor 邱国福邱千
Owner 邱国福
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