CN102807494A - Method for preparing fat alkyl dimethyl benzyl ammonium chloride - Google Patents
Method for preparing fat alkyl dimethyl benzyl ammonium chloride Download PDFInfo
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- CN102807494A CN102807494A CN2012102933343A CN201210293334A CN102807494A CN 102807494 A CN102807494 A CN 102807494A CN 2012102933343 A CN2012102933343 A CN 2012102933343A CN 201210293334 A CN201210293334 A CN 201210293334A CN 102807494 A CN102807494 A CN 102807494A
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- alkyl dimethyl
- fatty alkyl
- ammonium chloride
- organic solvent
- benzyl ammonium
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- -1 alkyl dimethyl benzyl ammonium chloride Chemical compound 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000003960 organic solvent Substances 0.000 claims abstract description 21
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229940073608 benzyl chloride Drugs 0.000 claims abstract description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 9
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000013078 crystal Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 16
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 238000012805 post-processing Methods 0.000 abstract 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 3
- 241000195493 Cryptophyta Species 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000013543 active substance Substances 0.000 description 2
- OCBHHZMJRVXXQK-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 OCBHHZMJRVXXQK-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- QDYLMAYUEZBUFO-UHFFFAOYSA-N cetalkonium chloride Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 QDYLMAYUEZBUFO-UHFFFAOYSA-N 0.000 description 2
- 229960000228 cetalkonium chloride Drugs 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002932 luster Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 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
- 230000001877 deodorizing effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing fat alkyl dimethyl benzyl ammonium chloride. Fattyalkyl dimethyl amine and benzyl chloride are reacted in an organic solvent to obtain the fat alkyl dimethyl benzyl ammonium chloride. The fat alkyl is one or mixed alkyl of two of dodecyl, myristyl and cetyl, and the organic solvent is one or two of petroleum ether, isopropyl ether, methyl tertiary-butyl ether, normal hexane, cyclohexane and benzene. The method comprises the following steps of 1, adding the fattyalkyl dimethyl amine and the organic solvent into a reaction device to be mixed, then adding the benzyl chloride, heating to 60-100 DEG C to carry out backflow reaction with water for 4-8 hours; 2, after the reaction is finished, recovering the organic solvent at ordinary pressure, and then evaporating the residual unrecovered organic solvent in a pressure-reducing mode; and 3, lowering the temperature to 40-50 DEG C, adding water, and obtaining fat alkyl dimethyl benzyl ammonium chloride with crystal water. The method has the advantages of simplicity in postprocessing, better color of a product, higher purity of the product and higher yield of the product and is suitable for industrial production.
Description
Technical field
The present invention relates to the preparation method of a cationoid tensio-active agent, be specifically related to a kind of preparation method of fatty alkyl dimethyl benzyl ammonium chloride.
Background technology
The fatty alkyl dimethyl benzyl ammonium chloride is a cationoid tensio-active agent; Belong to non-oxidizable sterilant; Have wide spectrum, sterilization algae removal ability efficiently; Can control bacterium algae propagation and foundry loam growth in the water effectively, and have the effect of peeling off of good foundry loam and certain dispersion, osmosis, have simultaneously certain deoil, deodorizing capability and corrosion inhibition.Fatty alkyl dimethyl benzyl ammonium chloride toxicity is little; There is not accumulation property toxicity; And soluble in water, not influenced by the water hardness, therefore be widely used in the recirculating cooling water system of industries such as oil, chemical industry, electric power, weaving; Grow in order to Control Circulation cooling water system bacterium algae, special efficacy is arranged killing sulphate reducing bacteria.The fatty alkyl dimethyl benzyl ammonium chloride also can be used as biocide mildewcide, softening agent, static inhibitor, emulsifying agent and amendment of textile printing and dyeing industry or the like.
At present, the preparation method of fatty alkyl dimethyl benzyl ammonium chloride is reacted in the presence of water by fatty alkyl dimethyl tertiary amine and Benzyl Chloride to obtain.This method is owing to adopt water as solvent, so need dewater in the last handling process.At first, because the latent heat of vaporization of water is higher, therefore steaming is bigger except that difficulty, and the time is longer, and aftertreatment is loaded down with trivial details.Secondly, because the boiling point of water is also higher, it is also higher that therefore steaming removes temperature, causes the product color and luster relatively poor like this, is yellow.At last, because the very easily suction again of fatty alkyl dimethyl benzyl ammonium chloride, so water also is difficult to eliminate, and causes the solid shape of product poor like this, is generally blockly or gluey, and purity is lower, and yield is lower, is not suitable for suitability for industrialized production.
Summary of the invention
The objective of the invention is to address the above problem, provide that a kind of aftertreatment is simple, product color is better, purity is higher, yield is higher, be fit to the preparation method of the fatty alkyl dimethyl benzyl ammonium chloride of suitability for industrialized production.
The technical scheme that realizes the object of the invention is: a kind of preparation method of fatty alkyl dimethyl benzyl ammonium chloride, it is reacted in organic solvent by fatty alkyl dimethyl tertiary amine and Benzyl Chloride and obtains.Described fatty alkyl is a kind of or two kinds of mixed alkyls in dodecyl, tetradecyl, the hexadecyl.Described organic solvent is a kind of in sherwood oil, isopropyl ether, MTBE, normal hexane, hexanaphthene and the benzene or two kinds, preferred sherwood oil.
Concrete steps are following: 1. fatty alkyl dimethyl tertiary amine and organic solvent are added in the reaction unit, stir adding Benzyl Chloride down, be heated to 60 ℃～100 ℃ band water reaction 4h～8h that reflux; 2. after reaction finished, first normal pressure reclaimed organic solvent, removes the organic solvent that residue does not reclaim again under reduced pressure; 3. be cooled to 40 ℃～50 ℃, add water, obtain containing the fatty alkyl dimethyl benzyl ammonium chloride of crystal water.
The mol ratio of 1. described fatty alkyl dimethyl tertiary amine of above-mentioned steps and Benzyl Chloride is 1: 0.9～1: 1.
The weight of the water that above-mentioned steps is added in 3. is 15%～16% of the fatty alkyl dimethyl tertiary amine weight that added in 1. of step.
The positively effect that the present invention has: (1) method of the present invention select boiling point lower, do not replace water as reaction solvent with the miscible organic solvent of water, after the reaction end, anhydrous in the material like this; Organic solvent then can reclaim and remove under reduced pressure through normal pressure in lower temperature and short time, and the organic solvent of recovery is capable of circulation to be applied mechanically, thereby makes aftertreatment simplify greatly; And the product color and luster is better, is white in color, and product purity is also higher; Yield is higher, is fit to suitability for industrialized production.(2) because the fatty alkyl dimethyl benzyl ammonium chloride has water-absorbent, so the present invention added a spot of water and made it to form the fatty alkyl dimethyl benzyl ammonium chloride that contains crystal water, thereby improves the stability of product.
Embodiment
(embodiment 1)
Present embodiment is the preparation method of dodecyl benzyl dimethyl ammonium chloride, has following steps:
1. in the reaction kettle of 500L, add the sherwood oil of 200kg and the dodecyl dimethyl tertiary amine (514mol) of 109.5kg, stir the Benzyl Chloride (490mol) that adds 62kg down, be heated to 70 ℃ of band water reaction 8h that reflux.Dodecyl dimethyl tertiary amine content >=97wt%, Benzyl Chloride content >=98wt%, the specification of sherwood oil is a technical grade.
2. after reaction finished, first normal pressure reclaimed sherwood oil, removes the sherwood oil that residue does not reclaim again under reduced pressure, until there not being sherwood oil, obtains the anhydride of dodecyl benzyl dimethyl ammonium chloride.
3. be cooled to 50 ℃, add 18.6kg water, insulation with the slicing machine pulverizing of cutting into slices, obtains the dodecyl benzyl dimethyl ammonium chloride that 174.4kg contains two molecular crystal water, and yield is 90.3%, and purity is 98.8%, and pH value (1% aqueous solution) is 7.5.
(embodiment 2～embodiment 5)
The preparation method of each embodiment and embodiment 1 are basic identical, and difference is seen table 1.
Table 1
| ? | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 |
| Reaction kettle | 500L | 500L | 1000L | 500L | 1000L |
| The dodecyl dimethyl tertiary amine | 109.5kg （514mol） | 109.5kg（514mol） | 224kg（1052mol） | 109.5kg（514mol） | 224kg（1052mol） |
| Benzyl Chloride | 62kg（490mol） | 62kg（490mol） | 128kg（1012mol） | 65kg（514mol） | 120kg（949mol） |
| Organic solvent | The 200kg sherwood oil | The 200kg sherwood oil | The 400kg normal hexane | The 200kg sherwood oil | The 400kg sherwood oil |
| Temperature of reaction | 70℃ | 80℃ | 70℃ | 70℃ | 80℃ |
| Reaction times | 8 | 7 | 8 | 6 | 4 |
| Add water temp | 50℃ | 40℃ | 50℃ | 45℃ | 50℃ |
| Add water weight | 16.5kg | 16.5kg | 36kg | 16.5kg | 33.6kg |
| The dodecyl benzyl dimethyl ammonium chloride that contains crystal water | 174.4kg | 175.3kg | 360.8kg | 174.9kg | 359.8kg |
| The pH value | 7.5 | 6.9 | 6.5 | 7.3 | 7.4 |
| Yield | 90.3% | 90.8% | 91.4% | 90.6% | 91.1% |
| Purity | 98.8% | 98.2% | 98.5% | 98.4% | 98.2% |
(embodiment 6～embodiment 10)
The preparation method of each embodiment and embodiment 1 are basic identical, and difference is seen table 2.
Table 2
| ? | Embodiment 6 | Embodiment 7 | Embodiment 8 | Embodiment 9 | Embodiment 10 |
| Reaction kettle | 500L | 500L | 500L | 500L | 500L |
| The fatty alkyl dimethyl tertiary amine | Dodecyl dimethyl tertiary amine 109.5kg | Tetradecyl dimethyl tertiary amine 109.5kg | 12/tetradecyl dimethyl tertiary amine 109.5kg | Hexadecyldimethyl benzyl ammonium tertiary amine 109.5kg | 12/hexadecyldimethyl benzyl ammonium tertiary amine 109.5kg |
| Benzyl Chloride | 62kg | 62kg | 62kg | 61kg | 61kg |
| Organic solvent | The 180kg isopropyl ether | The 200kg sherwood oil | The 200kg normal hexane | The 200kg hexanaphthene | The 190kg sherwood oil |
| Temperature of reaction | 75℃ | 80℃ | 80℃ | 80℃ | 80℃ |
| Reaction times | 8 | 7 | 8 | 7 | 8 |
| Add water temp | 50℃ | 40℃ | 50℃ | 45℃ | 50℃ |
| Add water weight | 16.5kg | 16.6kg | 16.8kg | 16.5kg | 16.7kg |
| The fatty alkyl dimethyl benzyl ammonium chloride that contains crystal water | 175.2kg dodecyl benzyl dimethyl ammonium chloride | 175.0kg tetradecyl dimethyl benzyl ammonium chloride | 174.8kg 12/tetradecyl dimethyl benzyl ammonium chloride | 175.9kg cetalkonium chloride | 176.1kg 12/cetalkonium chloride |
| The pH value | 7.0 | 6.9 | 6.8 | 7.3 | 7.1 |
| Yield | 90.8% | 90.7% | 91.6% | 91.1% | 91.2% |
| Purity | 98.2% | 98.5% | 98.5% | 98.8% | 98.2% |
Claims (7)
1. the preparation method of a fatty alkyl dimethyl benzyl ammonium chloride is characterized in that: reacted in organic solvent by fatty alkyl dimethyl tertiary amine and Benzyl Chloride and obtain; Described fatty alkyl is a kind of or two kinds of mixed alkyls in dodecyl, tetradecyl, the hexadecyl; Described organic solvent is a kind of in sherwood oil, isopropyl ether, MTBE, normal hexane, hexanaphthene and the benzene or two kinds.
2. the preparation method of fatty alkyl dimethyl benzyl ammonium chloride according to claim 1 is characterized in that: described organic solvent is a sherwood oil.
3. the preparation method of fatty alkyl dimethyl benzyl ammonium chloride according to claim 1 and 2 is characterized in that: the mol ratio of described fatty alkyl dimethyl tertiary amine and Benzyl Chloride is 1: 0.9～1: 1.
4. the preparation method of fatty alkyl dimethyl benzyl ammonium chloride according to claim 1 and 2 is characterized in that having following steps:
1. fatty alkyl dimethyl tertiary amine and organic solvent are added in the reaction unit, stir adding Benzyl Chloride down, be heated to 60 ℃～100 ℃ band water reaction 4h～8h that reflux;
2. after reaction finished, first normal pressure reclaimed organic solvent, removes the organic solvent that residue does not reclaim again under reduced pressure;
3. be cooled to 40 ℃～50 ℃, add water, obtain containing the fatty alkyl dimethyl benzyl ammonium chloride of crystal water.
5. the preparation method of fatty alkyl dimethyl benzyl ammonium chloride according to claim 4 is characterized in that: the fatty alkyl dimethyl tertiary amine of step described in 1. and the mol ratio of Benzyl Chloride are 1: 0.9～1: 1.
6. the preparation method of fatty alkyl dimethyl benzyl ammonium chloride according to claim 4 is characterized in that: the weight of the water that step is added in 3. is 15%～16% of the fatty alkyl dimethyl tertiary amine weight that added in 1. of step.
7. the preparation method of fatty alkyl dimethyl benzyl ammonium chloride according to claim 5 is characterized in that: the weight of the water that step is added in 3. is 15%～16% of the fatty alkyl dimethyl tertiary amine weight that added in 1. of step.
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| CN2012102933343A CN102807494A (en) | 2012-08-17 | 2012-08-17 | Method for preparing fat alkyl dimethyl benzyl ammonium chloride |
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| Application Number | Priority Date | Filing Date | Title |
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| CN2012102933343A CN102807494A (en) | 2012-08-17 | 2012-08-17 | Method for preparing fat alkyl dimethyl benzyl ammonium chloride |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104151172A (en) * | 2014-05-12 | 2014-11-19 | 浙江博莱特科技有限公司 | Method for producing refined benzalkonium chloride |
| CN113861037A (en) * | 2021-09-24 | 2021-12-31 | 泰柯棕化(张家港)有限公司 | Production process of low-residue medicinal benzalkonium chloride |
| CN115594593A (en) * | 2022-09-09 | 2023-01-13 | 四川博利恒药业有限公司（Cn） | Production process of benzalkonium chloride |
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| JPH10277560A (en) * | 1997-04-08 | 1998-10-20 | Katayama Chem Works Co Ltd | Method for preventing attaching of slime to seawater cooling water system |
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2012
- 2012-08-17 CN CN2012102933343A patent/CN102807494A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10277560A (en) * | 1997-04-08 | 1998-10-20 | Katayama Chem Works Co Ltd | Method for preventing attaching of slime to seawater cooling water system |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104151172A (en) * | 2014-05-12 | 2014-11-19 | 浙江博莱特科技有限公司 | Method for producing refined benzalkonium chloride |
| CN113861037A (en) * | 2021-09-24 | 2021-12-31 | 泰柯棕化(张家港)有限公司 | Production process of low-residue medicinal benzalkonium chloride |
| CN115594593A (en) * | 2022-09-09 | 2023-01-13 | 四川博利恒药业有限公司（Cn） | Production process of benzalkonium chloride |
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Application publication date: 20121205 |