CN104649903A - Sebacate hydroxyethyl tertiary amine compound and preparation method thereof - Google Patents
Sebacate hydroxyethyl tertiary amine compound and preparation method thereof Download PDFInfo
- Publication number
- CN104649903A CN104649903A CN201310598373.9A CN201310598373A CN104649903A CN 104649903 A CN104649903 A CN 104649903A CN 201310598373 A CN201310598373 A CN 201310598373A CN 104649903 A CN104649903 A CN 104649903A
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- CN
- China
- Prior art keywords
- tertiary amine
- trihydroxyethyl
- hydroxyethyl
- amine compound
- water
- Prior art date
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Links
- -1 Sebacate hydroxyethyl tertiary amine compound Chemical class 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 229940116351 sebacate Drugs 0.000 title abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 49
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000004821 distillation Methods 0.000 claims abstract description 9
- 238000005886 esterification reaction Methods 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 4
- 229910052751 metal Inorganic materials 0.000 claims abstract description 4
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 3
- 230000032050 esterification Effects 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 2
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- GLVPUAWFPNGKHO-UHFFFAOYSA-L N.[Fe+2].[O-]S([O-])(=O)=O Chemical compound N.[Fe+2].[O-]S([O-])(=O)=O GLVPUAWFPNGKHO-UHFFFAOYSA-L 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000005555 metalworking Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a sebacate hydroxyethyl tertiary amine compound and its preparation method. The preparation method is characterized in that sebacic acid and trihydroxyethyl tertiary amine undergo a neutralization reaction to prepare sebacate trihydroxyethyl tertiary ammonium salt; under the action of a catalyst, refuxing esterification is carried out by using methylbenzene as a water-carrying agent; and reduced pressure distillation is carried out to remove methylbenzene so as to prepare the sebacate hydroxyethyl tertiary amine compound. Sources of raw materials are sufficient, and costs are low. The composition is an organic polybasic carboxylate hydroxyethyl tertiary amine compound, has characteristics of two carbanyl groups and amino groups binding to metal, has an antirust effect, has multiple hydroxyethyl groups and has good water solubility. The composition is diester and has certain lubricity.
Description
Technical field
The present invention relates to rust-inhibiting additive synthesis technical field, espespecially a kind of sebate hydroxyethyl tertiary amine compound 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, polar group in rust-inhibiting additive molecule can be adsorbed in metallic surface, and hydrophobic alkyl forms protective membrane in metallic surface, play rust-proof effect, the solvability of organic molecule in water is relevant with the hydrophilic radical of alkyl chain, as water miscible rust-inhibiting additive, the polar group playing rust inhibition not only will be had in molecule, and to have certain water-soluble, along with improving constantly of modern machinery and equipment performance, environmental requirement is increasingly harsh, produce, need in life to use high performance rust-inhibiting additive, 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.
Summary of the invention
The object of the present invention is to provide a kind of sebate hydroxyethyl tertiary amine compound and preparation method thereof.
Technical solution of the present invention is: sebacic acid and trihydroxyethyl tertiary amine carry out neutralization reaction, produce sebacic acid trihydroxyethyl tertiary ammonium salt, under catalyst action, be water entrainer again with toluene, carry out refuxing esterification reaction, underpressure distillation removing toluene, obtained sebate hydroxyethyl tertiary amine compound, specifically comprises following steps:
1). sebacic acid (I) and trihydroxyethyl tertiary amine (II), stirring reaction 1 ~ 2 hour at 40 DEG C ~ 60 DEG C, produce sebacic acid trihydroxyethyl tertiary ammonium salt (III), its main chemical reactions is:
2). take toluene as water entrainer, under catalyst action, sebacic acid and trihydroxyethyl tertiary ammonium salt (III) are at 140 DEG C ~ 170 DEG C, carry out refuxing esterification reaction, the water that water-and-oil separator separating reaction generates, reacted after 4 ~ 6 hours, underpressure distillation removing toluene, obtained sebate hydroxyethyl tertiary amine compound (IV), its main chemical reactions is:
Further, the mol ratio of described sebacic acid and trihydroxyethyl tertiary amine is 1 ﹕ 2 ~ 3.
Described catalyzer is the metal ammonium salt of sulfuric acid or the metal-salt of thionamic acid, and its consumption is 0.5% ~ 2% of trihydroxyethyl tertiary amine consumption.
A kind of sebate hydroxyethyl of the present invention tertiary amine compound and preparation method thereof, its feature and advantage are: sufficient raw, and cost is lower; Synthetics is a kind of organic polycarboxylic acid ester hydroxyethyl tertiary amine compound, has two carbonyls and characteristic that is amino and melts combine, can play rust inhibition; There is multiple hydroxyethyl, good water solubility; Synthetics is a kind of dibasic acid esters, has certain oilness; Operation is simple, is applicable to suitability for industrialized production.
Embodiment
Embodiment 1
In the four-hole bottle that whipping appts, reflux condensate device and thermometer are housed, add 34 grams of trihydroxyethyl tertiary amines, add 23 grams of sebacic acid in batches, at 40 DEG C ~ 50 DEG C, stirring reaction is after 1 ~ 2 hour, produce sebacic acid trihydroxyethyl tertiary ammonium salt, add 80mL methylbenzene water-taking agent again, add 0.2 gram of catalyst sulfuric acid iron ammonium, under being heated to 140 DEG C ~ 170 DEG C temperature, carry out refuxing esterification reaction, the water that water-and-oil separator separating reaction generates, react after 5 ~ 6 hours, underpressure distillation removing toluene, obtained sebate hydroxyethyl tertiary amine compound.
Embodiment 2
In the four-hole bottle that whipping appts, reflux condensate device and thermometer are housed, add 48 grams of trihydroxyethyl tertiary amines, add 26 grams of sebacic acid in batches, at 45 DEG C ~ 55 DEG C, stirring reaction is after 1 ~ 2 hour, produce sebacic acid trihydroxyethyl tertiary ammonium salt, add 100mL methylbenzene water-taking agent again, add 0.6 gram of catalyst sulfuric acid iron ammonium, under being heated to 140 DEG C ~ 170 DEG C temperature, carry out refuxing esterification reaction, the water that water-and-oil separator separating reaction generates, react after 4.5 ~ 5.5 hours, underpressure distillation removing toluene, obtained sebate hydroxyethyl tertiary amine compound.
Embodiment 3
In the four-hole bottle that whipping appts, reflux condensate device and thermometer are housed, add 64 grams of trihydroxyethyl tertiary amines, add 29 grams of sebacic acid in batches, at 50 DEG C ~ 60 DEG C, stirring reaction is after 1 ~ 2 hour, produce sebacic acid trihydroxyethyl tertiary ammonium salt, add 150mL methylbenzene water-taking agent again, add 1.2 grams of catalyst sulfuric acid iron ammoniums, under being heated to 140 DEG C ~ 170 DEG C temperature, carry out refuxing esterification reaction, the water that water-and-oil separator separating reaction generates, react after 4 ~ 5 hours, underpressure distillation removing toluene, obtained sebate hydroxyethyl tertiary amine compound.
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. sebate hydroxyethyl tertiary amine compound and preparation method thereof, it is characterized in that: sebacic acid and trihydroxyethyl tertiary amine carry out neutralization reaction, produce sebacic acid trihydroxyethyl tertiary ammonium salt, under catalyst action, take toluene as water entrainer again, carry out refuxing esterification reaction, underpressure distillation removing toluene, obtained sebate hydroxyethyl tertiary amine compound, specifically comprises following steps:
1). sebacic acid and trihydroxyethyl tertiary amine, stirring reaction 1 ~ 2 hour at 40 DEG C ~ 60 DEG C, produces sebacic acid trihydroxyethyl tertiary ammonium salt;
2). take toluene as water entrainer, under catalyst action, sebacic acid and trihydroxyethyl tertiary ammonium salt, at 140 DEG C ~ 170 DEG C, carry out refuxing esterification reaction, the water that water-and-oil separator separating reaction generates, react after 4 ~ 6 hours, underpressure distillation removing toluene, obtained sebate hydroxyethyl tertiary amine compound;
3). using toluene as water entrainer, the methyne acid esterification intermediate product of tolyltriazole and monohydroxyalkyl group primary amine, heating reflux reaction is continued at 110 ~ 130 DEG C, water-and-oil separator is separated the water generated, react after 2 ~ 4 hours, underpressure distillation removing toluene, the secondary methylol boric acid ester compound of obtained tolyltriazole.
2. a kind of sebate hydroxyethyl tertiary amine compound according to claim 1 and preparation method thereof, is characterized in that: the mol ratio of described sebacic acid and trihydroxyethyl tertiary amine is 1 ﹕ 2 ~ 3; Described catalyzer is the metal ammonium salt of sulfuric acid or the metal-salt of thionamic acid, and its consumption is 0.5% ~ 2% of trihydroxyethyl tertiary amine consumption.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310598373.9A CN104649903A (en) | 2013-11-25 | 2013-11-25 | Sebacate hydroxyethyl tertiary amine compound and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310598373.9A CN104649903A (en) | 2013-11-25 | 2013-11-25 | Sebacate hydroxyethyl tertiary amine compound and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104649903A true CN104649903A (en) | 2015-05-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310598373.9A Pending CN104649903A (en) | 2013-11-25 | 2013-11-25 | Sebacate hydroxyethyl tertiary amine compound and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104649903A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0664331A1 (en) * | 1994-01-20 | 1995-07-26 | Shell Internationale Researchmaatschappij B.V. | Substituted polyoxyalkylene compounds |
| EP2196451A1 (en) * | 2007-10-11 | 2010-06-16 | Takasago International Corporation | Acylation reaction of hydroxyl group |
| CN102002415A (en) * | 2009-09-02 | 2011-04-06 | 中国石油天然气股份有限公司 | A kind of ashless antirust additive that can be used for industrial lubricating oil and preparation method thereof |
-
2013
- 2013-11-25 CN CN201310598373.9A patent/CN104649903A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0664331A1 (en) * | 1994-01-20 | 1995-07-26 | Shell Internationale Researchmaatschappij B.V. | Substituted polyoxyalkylene compounds |
| EP2196451A1 (en) * | 2007-10-11 | 2010-06-16 | Takasago International Corporation | Acylation reaction of hydroxyl group |
| CN102002415A (en) * | 2009-09-02 | 2011-04-06 | 中国石油天然气股份有限公司 | A kind of ashless antirust additive that can be used for industrial lubricating oil and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| 杨必暖: "水锈防止剂", 《涂料工业》 * |
| 谢磊: "酯化三乙醇胺类新型水泥助磨剂的应用研究", 《北京交通大学硕士学位论文》 * |
| 韩立兴: "金属防锈剂的制备与应用", 《中国优秀硕士学位论文数据库 工程科技I辑》 * |
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150527 |