CN1939889A - Synthesis of fat tertiary amine quaternary ammonium salt derivative - Google Patents
Synthesis of fat tertiary amine quaternary ammonium salt derivative Download PDFInfo
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- CN1939889A CN1939889A CN 200610048203 CN200610048203A CN1939889A CN 1939889 A CN1939889 A CN 1939889A CN 200610048203 CN200610048203 CN 200610048203 CN 200610048203 A CN200610048203 A CN 200610048203A CN 1939889 A CN1939889 A CN 1939889A
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- tertiary amine
- quaternary ammonium
- ammonium salt
- fat tertiary
- fat
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Abstract
Synthesis of fatty tertiary amine quaternary ammonium salt derivative is carried out by putting long-chain fatty tertiary amine and methyl-carbonate into pressure pan, adding into low-carbon alcohol solvent, raising temperature to 130-160 degree, keeping reactive pressure to 0.5MPa-1.5MPa, and reacting for 4-10hrs to obtain quaternary ammonium ester. The fatty tertiary amine : methyl-carbonate is 1.0:1.5-6.0mol, and low-carbon alcohol solvent is 50%-200wt%. It has excellent biological degradability and environmental compatibility and low ecological toxicity.
Description
Technical field
The invention belongs to a kind of synthetic method of fat tertiary amine quaternary ammonium salt derivative, specifically the method for synthesizing tertiary amine quaternary ammonium salt with single, double long-chain alkyl tertiary amine and a kind of quaternizing agent methylcarbonate.
Background technology
The quaternary ammonium salt of long-chain fat tertiary amine is the very important organic chemicals of a class, is mainly used in petrochemical complex, agricultural chemicals, medical and health, weaving and daily use chemicals industry etc. as sterilant, washing composition and static inhibitor etc.The quaternizing agent of the cationic quaternary ammonium salt derivative of present industrial use mainly contains methyl chloride, Benzyl Chloride, methyl-sulfate etc., and is poisonous and there is corrosion in equipment.Methylcarbonate was just classified as nontoxic product by Europe in 1992, was a kind of environment-friendly and green raw material that the modern times " cleaning procedure " require that meets.The patent of making quaternizing agent synthesizing ester amine class quaternary ammonium salt with methylcarbonate has DE4338998, CN1562960A, and the patent of synthetic imidazolines ester quat has JP1017554.For using methylcarbonate not appear in the newspapers as yet as the synthetic long-chain fat tertiary amine quaternary ammonium salt derivative of quaternizing agent.
Summary of the invention
The objective of the invention is to invent a kind of synthetic method of using methylcarbonate to prepare fat tertiary amine quaternary ammonium salt derivative as quaternizing agent.
The chemical structural formula of the quaternary ammonium salt that single, double fat tertiary amine of the present invention and dimethyl carbonate generate is as follows:
In the formula: R is C
8～C
18Saturated or unsaturated straight chain or have the alkyl of side chain;
R ' is CH
3-Or same R.
Synthetic method of the present invention:
Long-chain fat tertiary amine and methylcarbonate are put into autoclave, add the low-carbon alcohol solvent simultaneously, be warming up to 130 ℃～160 ℃, keep reaction pressure 0.5MPa～1.5MPa, reaction 4～10hr obtains ester quat;
Each amounts of components is: the mol ratio of fat tertiary amine and methylcarbonate 1.0: 1.5～6.0, be preferably 1.0: 3.0～and 5.0, the low-carbon alcohol solvent load is 50%～200% of a fat tertiary amine quality, is preferably 80～150%.
Aforesaid long-chain fat tertiary amine is: C
8～C
18Single long-chain fat tertiary amine, C
8～C
18Two long-chain fat tertiary amines.
Aforesaid single long-chain fat tertiary amine is dodecyl dimethyl tertiary amine, octadecyl dimethyl tertiary amine etc.
Aforesaid pair of long-chain fat tertiary amine is two C
8-10Alkyl methyl tertiary amine, two C
12Alkyl methyl tertiary amine, two C
18Alkyl methyl tertiary amine etc.
Aforesaid low-carbon alcohol solvent is: one or more in methyl alcohol, dehydrated alcohol, Virahol, ethylene glycol, the propylene glycol.
The product of the present invention's preparation is a cats product, characteristic with cats product, the disinfectant that can be used as Treatment of Industrial Water, aquaculture, oil-field flooding sterilant and play apparatus, communal facility etc., synthon static inhibitor, carding auxiliary agent and mineral float makes agent etc.
The present invention compared with prior art has following advantage:
1. this product has excellent biodegradability, eco-toxicity is low and Environmental compatibility good.
2. this technology uses environmental protection material carbon dimethyl phthalate to substitute has corrosion and deleterious quaternizing agent methyl chloride, Benzyl Chloride etc. to equipment, has avoided to the pollution of environment and to the corrosion of equipment.
3. adopt this synthetic method synthetic product performance to be higher than or to be equal to the quaternary ammonium salt product that tertiary amine of the same race is quaternizing agent with the methyl chloride.
Embodiment
Embodiment 1
Take by weighing dodecyl dimethyl tertiary amine 55g, methylcarbonate 45g, Virahol 100g adds in the 1L autoclave, is warming up to 150 ℃, and 0.8MPa is reaction 4hr down.The transformation efficiency of dodecyl dimethyl tertiary amine is 83.89%.
Embodiment 2
Take by weighing two C
18Alkyl methyl tertiary amine 88g, methylcarbonate 61g, ethylene glycol 50g adds in the 1L autoclave, is warming up to 150 ℃, and 15MPa is reaction 6hr down, and transformation efficiency is 80.28%.
Embodiment 3
Take by weighing octadecyl dimethyl tertiary amine 48g, methylcarbonate 22g, Virahol 70g adds in the 1L autoclave, is warming up to 130 ℃, and 0.5MPa is reaction 10hr down, and transformation efficiency is 55.13%.
Embodiment 4
Take by weighing dodecyl dimethyl tertiary amine 55g, methylcarbonate 45g, methyl alcohol 40g, propylene glycol 40g adds in the 1L autoclave, is warming up to 150 ℃, and 1.0MPa is reaction 8hr down, and transformation efficiency is 96.91%.
Embodiment 5
Take by weighing two C
8-10Alkyl methyl tertiary amine 73g, methylcarbonate 38g, Virahol 35g, methyl alcohol 5g adds in the 1L autoclave, is warming up to 160 ℃, and 10MPa is reaction 6hr down, and transformation efficiency is 68.82%.
Embodiment 6
Take by weighing two C
12Alkyl methyl tertiary amine 58g, methylcarbonate 72g, methyl alcohol 3g, dehydrated alcohol 10g, Virahol 7g, ethylene glycol 8g, propylene glycol 5g add in the 1L autoclave, are warming up to 150 ℃, and 0.8MPa is reaction 8hr down, and transformation efficiency is 91.93%.
Embodiment 7
Take by weighing two C
8-10Alkyl methyl tertiary amine 58g, methylcarbonate 90g, dehydrated alcohol 33g adds in the 1L autoclave, is warming up to 150 ℃, and 0.9MPa is reaction 8hr down, and transformation efficiency is 95.56%.
Claims (7)
1, a kind of synthetic method of fat tertiary amine quaternary ammonium salt derivative is characterized in that comprising the steps:
Long-chain fat tertiary amine and methylcarbonate are put into autoclave, add the low-carbon alcohol solvent simultaneously, be warming up to 130 ℃～160 ℃, keep reaction pressure 0.5MPa～1.5MPa, reaction 4～10hr obtains ester quat; Each amounts of components is: the mol ratio of fat tertiary amine and methylcarbonate 1.0: 1.5～6.0, low-carbon alcohol solvent load are 50%～200% of fat tertiary amine quality.
2, the synthetic method of a kind of fat tertiary amine quaternary ammonium salt derivative as claimed in claim 1 is characterized in that the mol ratio 1.0: 3.0～5.0 of described fat tertiary amine and methylcarbonate.
3, the synthetic method of a kind of fat tertiary amine quaternary ammonium salt derivative as claimed in claim 1 is characterized in that described low-carbon alcohol solvent load is 80～150% of a fat tertiary amine quality.
4, the synthetic method of a kind of fat tertiary amine quaternary ammonium salt derivative as claimed in claim 1 is characterized in that described long-chain fat tertiary amine is: C
8～C
18Single long-chain fat tertiary amine or C
8～C
18Two long-chain fat tertiary amines.
5, the synthetic method of a kind of fat tertiary amine quaternary ammonium salt derivative as claimed in claim 4 is characterized in that described single long-chain fat tertiary amine is dodecyl dimethyl tertiary amine or octadecyl dimethyl tertiary amine.
6, the synthetic method of a kind of fat tertiary amine quaternary ammonium salt derivative as claimed in claim 4 is characterized in that described pair of long-chain fat tertiary amine is two C
8-10Alkyl methyl tertiary amine, two C
12Alkyl methyl tertiary amine or two C
18The alkyl methyl tertiary amine.
7, the synthetic method of a kind of fat tertiary amine quaternary ammonium salt derivative as claimed in claim 1 is characterized in that described low-carbon alcohol solvent is: one or more in methyl alcohol, dehydrated alcohol, Virahol, ethylene glycol, the propylene glycol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100482033A CN100436402C (en) | 2006-08-24 | 2006-08-24 | Synthesis of fat tertiary amine quaternary ammonium salt derivative |
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|---|---|---|---|
| CNB2006100482033A CN100436402C (en) | 2006-08-24 | 2006-08-24 | Synthesis of fat tertiary amine quaternary ammonium salt derivative |
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| CN1939889A true CN1939889A (en) | 2007-04-04 |
| CN100436402C CN100436402C (en) | 2008-11-26 |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351719A (en) * | 2011-10-08 | 2012-02-15 | 中国日用化学工业研究院 | Dialkyl dimethyl quaternary ammonium salt and preparation method thereof |
| CN102675155A (en) * | 2012-04-25 | 2012-09-19 | 中国日用化学工业研究院 | Guanidyl modified quaternary ammonium salt and synthetic method thereof |
| CN102816075A (en) * | 2012-08-24 | 2012-12-12 | 四川大学 | Preparation method of long-chain quaternary ammonium surfactant |
| CN103044264A (en) * | 2012-09-07 | 2013-04-17 | 赵立地 | Method for preparing quaternary ammonium salt |
| CN103111324A (en) * | 2013-01-25 | 2013-05-22 | 中南大学 | Application of bromine or iodine-containing haloid and method for synthesizing methyl three-long-chain aliphatic group quaternary ammonium salt derivative |
| CN104926668A (en) * | 2015-05-21 | 2015-09-23 | 北京盖雅环境科技有限公司 | Method for preparing tri-long-chain alkyl-ammonium bicarbonate and carbonate |
| CN107400043A (en) * | 2016-05-20 | 2017-11-28 | 中国科学院过程工程研究所 | Application and propylene glycol synthetic method of the ionic liquid in propylene glycol synthesis |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3816328A1 (en) * | 1988-05-13 | 1989-11-23 | Hoechst Ag | METHOD FOR PRODUCING QUATERNAUS AMMONIUM SALTS LONG-CHAIN ALIPHATIC CARBONIC ACIDS AND USE OF THESE AMMONIUM SALTS |
| CN1255374C (en) * | 2004-03-29 | 2006-05-10 | 中国日用化学工业研究院 | Quaternary ammonium salt in ester-amines and synthetic method |
-
2006
- 2006-08-24 CN CNB2006100482033A patent/CN100436402C/en not_active Expired - Fee Related
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351719A (en) * | 2011-10-08 | 2012-02-15 | 中国日用化学工业研究院 | Dialkyl dimethyl quaternary ammonium salt and preparation method thereof |
| CN102351719B (en) * | 2011-10-08 | 2014-07-02 | 中国日用化学工业研究院 | Dialkyl dimethyl quaternary ammonium salt and preparation method thereof |
| CN102675155A (en) * | 2012-04-25 | 2012-09-19 | 中国日用化学工业研究院 | Guanidyl modified quaternary ammonium salt and synthetic method thereof |
| CN102816075A (en) * | 2012-08-24 | 2012-12-12 | 四川大学 | Preparation method of long-chain quaternary ammonium surfactant |
| CN103044264A (en) * | 2012-09-07 | 2013-04-17 | 赵立地 | Method for preparing quaternary ammonium salt |
| CN103111324A (en) * | 2013-01-25 | 2013-05-22 | 中南大学 | Application of bromine or iodine-containing haloid and method for synthesizing methyl three-long-chain aliphatic group quaternary ammonium salt derivative |
| CN104926668A (en) * | 2015-05-21 | 2015-09-23 | 北京盖雅环境科技有限公司 | Method for preparing tri-long-chain alkyl-ammonium bicarbonate and carbonate |
| CN104926668B (en) * | 2015-05-21 | 2018-02-27 | 北京盖雅环境科技有限公司 | A kind of preparation method of tri-long-chain alkyl ammonium bicarbonate and carbonate |
| CN107400043A (en) * | 2016-05-20 | 2017-11-28 | 中国科学院过程工程研究所 | Application and propylene glycol synthetic method of the ionic liquid in propylene glycol synthesis |
| CN107400043B (en) * | 2016-05-20 | 2020-12-29 | 中国科学院过程工程研究所 | Application of ionic liquid in synthesis of propylene glycol ether and synthesis method of propylene glycol ether |
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| Publication number | Publication date |
|---|---|
| CN100436402C (en) | 2008-11-26 |
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