CN104649987A - Triazine trithione butyrate hydroxyalkyl tertiary ammonium salt and preparation method thereof - Google Patents

Triazine trithione butyrate hydroxyalkyl tertiary ammonium salt and preparation method thereof Download PDF

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Publication number
CN104649987A
CN104649987A CN201310598260.9A CN201310598260A CN104649987A CN 104649987 A CN104649987 A CN 104649987A CN 201310598260 A CN201310598260 A CN 201310598260A CN 104649987 A CN104649987 A CN 104649987A
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China
Prior art keywords
trimerization
tertiary amines
sulphur cyanogen
triazine
preparation
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CN201310598260.9A
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Chinese (zh)
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刘现梅
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Individual
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/38—Sulfur atoms
    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/20—Thiols; Sulfides; Polysulfides
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • C10M2215/222—Triazines
    • 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
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses triazine trithione butyrate hydroxyalkyl tertiary ammonium salt and its preparation method. The preparation method is characterized in that cyanuric sulfide and crotonic acid undergo an addition reaction under the action of an acid catalyst; and after a compound generated by the reaction undergoes purification such as filtration, alkali dissolution, acidification and the like, the purified compound reacts with hydroxyalkyl tertiary amine to generate a triazine trithione butyrate hydroxyalkyl tertiary ammonium salt rust-inhibiting additive. The composition is an alcohol amine salt of organic heterocyclic polycarboxylic acid, has characteristics of multiple carboxyl groups binding to metal and can have an excellent rust-inhibiting effect. The composition contains elements such as sulfur and nitrogen for providing lone pair electrons and has extreme pressure property. The reaction operation is simple and feasible.

Description

A kind of triazine tri-thiol butyric acid tertiary amines salt and preparation method thereof
Technical field
The present invention relates to organic lubricating and antirust additive chemistry synthesis technical field, espespecially a kind of triazine tri-thiol butyric acid tertiary amines salt and preparation method thereof.
Background technology
Water-based metal working fluid is because having excellent cooling, cleaning, rust-preventing characteristic, the advantage such as economy and security, be developed rapidly, and be widely used in cutting, grinding, calendering, the metal processing sectors such as punching press and tapping, rust-inhibiting additive is the important component part of water-based metal working fluid, along with the development and application of organic rust preventing additive, inorganic salts rust-inhibiting additive is substituted gradually, carboxyl is the essential groups of natural organic ligand and melts combine, the size of its corrosion inhibition, depend primarily on molecular structure, in metallic surface, keying action is played to molecular adsorption.
Trimerization sulphur cyanogen is a kind of abundance of originating, has the industrial chemicals of stable triazine chemical structure, by functional group and reaction, by functional group and reaction, can synthesize outstanding lubricating and antirust additive.
Summary of the invention
The object of the present invention is to provide a kind of triazine tri-thiol butyric acid tertiary amines salt and preparation method thereof.
Technical solution of the present invention is: to achieve these goals, technical solution of the present invention is: trimerization sulphur cyanogen and β-crotonic acid, addition reaction is carried out under an acidic catalyst effect, after the compound that its reaction generates after filtration, alkali dissolution, acidifying etc. purify, react with tertiary amines again, generate triazine tri-thiol butyric acid tertiary amines salt rust-inhibiting additive, specifically comprise following steps:
1). take water as solvent, trimerization sulphur cyanogen (I) and β-crotonic acid (II) are under an acidic catalyst effect, react 3 ~ 5 hours at 40 DEG C ~ 50 DEG C, generate trimerization sulphur cyanogen intermediate compound (III) containing crotons acidic group, its main chemical reactions is:
2). above-mentioned reaction mass is cooled to less than 30 DEG C, thin up, filter, filter cake alkaline aqueous solution dissolves, again cross and filter insolubles, it is 1 ~ 3 that filtrate acid solution is acidified to PH, filters, washes, trimerization sulphur cyanogen intermediate compound (V) containing crotons acidic group that must purify, its main chemical reactions is:
3). trimerization sulphur cyanogen intermediate compound (V) containing crotons acidic group of purification and tertiary amines (VI), at 20 ~ 40 DEG C, carry out reaction 1 ~ 2 hour, obtained triazine tri-thiol butyric acid tertiary amines salt rust-inhibiting additive (VII), its main chemical reactions is:
In formula, R 1, R 2and R 2the short chain hydroxyalkyls such as hydroxyethyl independent of each other, hydroxypropyl, hydroxyl sec.-propyl, hydroxyl butyl or hydroxyl isobutyl-.
  
Further, the mol ratio of described trimerization sulphur cyanogen, β-crotonic acid and tertiary amines is 1 ﹕ 3 ~ 3.5 ﹕ 6 ~ 8.
Described an acidic catalyst selects 60% sulfuric acid, and its consumption is 200% ~ 300% of trimerization sulphur cyanogen consumption.。
Described alkaline aqueous solution is one or more materials in sodium hydroxide, potassium hydroxide, sodium carbonate, salt of wormwood and sodium bicarbonate, the aqueous solution be mixed with after dissolving in water.
A kind of method utilizing hydrogenated terpinene maleic anhydride to prepare rust-inhibiting lubricant of the present invention, its feature and advantage are: sufficient raw, and cost is lower; Synthetics is a kind of alcohol amine salt of organic heterocyclic polycarboxylic acid, has the characteristic of multiple carboxyl and melts combine, can play excellent rust inhibition; The element that synthetics contains sulphur, nitrogen can provide lone-pair electron, and there is extreme pressure property; Operation is simple, is applicable to suitability for industrialized production.
Embodiment
Embodiment 1
Whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add the trimerization sulphur cyanogen of 29 grams, 60% sulfate sulfatase 58 grams, at 40 DEG C ~ 60 DEG C, add the β-crotonic acid of 43 grams in batches, react 2 ~ 4 hours, reaction mass is cooled to less than 30 DEG C, thin up, filter, filter cake aqueous sodium carbonate dissolves, again cross and filter insolubles, it is 1 ~ 3 that filtrate dilute sulfuric acid solution is acidified to PH, filter, washing, the trimerization sulphur cyanogen intermediate compound containing crotons acidic group that must purify, the obtained trimerization sulphur cyanogen intermediate compound containing crotons acidic group, add 188 grams of hydroxyl sec.-propyl tertiary amines, at 20 ~ 40 DEG C, carry out reaction 1 ~ 2 hour, obtained triazine tri-thiol butyric acid tertiary amines salt rust-inhibiting additive.
Embodiment 2
Whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add the trimerization sulphur cyanogen of 35 grams, 60% sulfate sulfatase 70 grams, at 40 DEG C ~ 60 DEG C, add the β-crotonic acid of 56 grams in batches, react 2 ~ 4 hours, reaction mass is cooled to less than 30 DEG C, thin up, filter, filter cake potassium hydroxide aqueous solution dissolves, again cross and filter insolubles, it is 1 ~ 3 that filtrate dilute sulfuric acid solution is acidified to PH, filter, washing, the trimerization sulphur cyanogen intermediate compound containing crotons acidic group that must purify, the obtained trimerization sulphur cyanogen intermediate compound containing crotons acidic group, add 104 grams of hydroxyethyl tertiary amines and 130 grams of hydroxyl sec.-propyl tertiary amines, at 20 ~ 40 DEG C, carry out reaction 1 ~ 2 hour, obtained triazine tri-thiol butyric acid tertiary amines salt rust-inhibiting additive.
Embodiment 3
Whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add the trimerization sulphur cyanogen of 25 grams, 60% sulfate sulfatase 75 grams, at 40 DEG C ~ 60 DEG C, add the β-crotonic acid of 42 grams in batches, react 2 ~ 4 hours, reaction mass is cooled to less than 30 DEG C, thin up, filter, filter cake aqueous sodium hydroxide solution dissolves, again cross and filter insolubles, it is 1 ~ 3 that filtrate dilute sulfuric acid solution is acidified to PH, filter, washing, the trimerization sulphur cyanogen intermediate compound containing crotons acidic group that must purify, the obtained trimerization sulphur cyanogen intermediate compound containing crotons acidic group, add 168 grams of hydroxyethyl tertiary amines, at 20 ~ 40 DEG C, carry out reaction 1 ~ 2 hour, obtained triazine tri-thiol butyric acid tertiary amines salt rust-inhibiting additive.
The above; embodiment is only be described the preferred embodiment of the present invention; not scope of the present invention is limited; under the prerequisite of spirit not departing from the technology of the present invention; the various distortion that this area engineering technical personnel make technical scheme of the present invention and improvement, all should fall in protection domain that claims of the present invention determine.

Claims (2)

1. triazine tri-thiol butyric acid tertiary amines salt and preparation method thereof, it is characterized in that: trimerization sulphur cyanogen and β-crotonic acid, addition reaction is carried out under an acidic catalyst effect, after the compound that its reaction generates after filtration, alkali dissolution, acidifying etc. purify, react with tertiary amines again, generate triazine tri-thiol butyric acid tertiary amines salt rust-inhibiting additive, specifically comprise following steps:
1). take water as solvent, trimerization sulphur cyanogen and β-crotonic acid, under an acidic catalyst effect, react 3 ~ 5 hours at 40 DEG C ~ 50 DEG C, generate the trimerization sulphur cyanogen intermediate compound containing crotons acidic group;
2). above-mentioned reaction mass is cooled to less than 30 DEG C, thin up, filters, filter cake alkaline aqueous solution dissolves, and again cross and filter insolubles, it is 1 ~ 3 that filtrate acid solution is acidified to PH, filter, wash, obtain the trimerization sulphur cyanogen intermediate compound containing crotons acidic group of purification;
3). the trimerization sulphur cyanogen intermediate compound containing crotons acidic group of purification and tertiary amines, at 20 ~ 40 DEG C, carry out reaction 1 ~ 2 hour, obtained triazine tri-thiol butyric acid tertiary amines salt rust-inhibiting additive.
2. a kind of triazine tri-thiol butyric acid tertiary amines salt according to claim 1 and preparation method thereof, is characterized in that: the mol ratio of described trimerization sulphur cyanogen, β-crotonic acid and tertiary amines is 1 ﹕ 3 ~ 3.5 ﹕ 6 ~ 8; Described an acidic catalyst selects 60% sulfuric acid, and its consumption is 200% ~ 300% of trimerization sulphur cyanogen consumption; Described alkaline aqueous solution is one or more materials in sodium hydroxide, potassium hydroxide, sodium carbonate, salt of wormwood and sodium bicarbonate, the aqueous solution be mixed with after dissolving in water.
CN201310598260.9A 2013-11-25 2013-11-25 Triazine trithione butyrate hydroxyalkyl tertiary ammonium salt and preparation method thereof Pending CN104649987A (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5549847A (en) * 1991-04-24 1996-08-27 Ciba-Geigy Corporation Flowable aqueous dispersions of polycarboxylic acid corrosion inhibitors
CN1760352A (en) * 2005-11-10 2006-04-19 上海大学 Water based additive for metal machining liquid, and preparation method
CN102250027A (en) * 2011-05-16 2011-11-23 修建东 Preparation method of 2,4,6-tri(caproyl aminomethyl sulfo)-s-triazine
CN102492533A (en) * 2011-11-28 2012-06-13 上海应用技术学院 Hard water-resistant semi-synthetic metal cutting fluid and preparation method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5549847A (en) * 1991-04-24 1996-08-27 Ciba-Geigy Corporation Flowable aqueous dispersions of polycarboxylic acid corrosion inhibitors
CN1760352A (en) * 2005-11-10 2006-04-19 上海大学 Water based additive for metal machining liquid, and preparation method
CN102250027A (en) * 2011-05-16 2011-11-23 修建东 Preparation method of 2,4,6-tri(caproyl aminomethyl sulfo)-s-triazine
CN102492533A (en) * 2011-11-28 2012-06-13 上海应用技术学院 Hard water-resistant semi-synthetic metal cutting fluid and preparation method thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
薛守庆，等: "基于噻二唑型水基润滑油防锈剂的合成，表征和应用", 《渤海大学学报（自然科学版）》 *

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