CN105732694A - Method for adsorbing and purifying 1, 1, 1, 3, 5, 5, 5-heptamethyltrisiloxane - Google Patents
Method for adsorbing and purifying 1, 1, 1, 3, 5, 5, 5-heptamethyltrisiloxane Download PDFInfo
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- CN105732694A CN105732694A CN201610139441.9A CN201610139441A CN105732694A CN 105732694 A CN105732694 A CN 105732694A CN 201610139441 A CN201610139441 A CN 201610139441A CN 105732694 A CN105732694 A CN 105732694A
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- Prior art keywords
- heptamethyltrisiloxane
- purification
- exchange column
- product
- adsorbent resin
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- SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 16
- 239000011347 resin Substances 0.000 claims abstract description 27
- 229920005989 resin Polymers 0.000 claims abstract description 27
- 239000000047 product Substances 0.000 claims abstract description 19
- 239000003463 adsorbent Substances 0.000 claims abstract description 14
- 239000012043 crude product Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000000746 purification Methods 0.000 claims description 15
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 150000001735 carboxylic acids Chemical class 0.000 claims description 9
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 6
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 6
- -1 Alkyl carboxylic acid Chemical class 0.000 claims description 5
- 238000007664 blowing Methods 0.000 claims description 5
- 238000007265 chloromethylation reaction Methods 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 4
- RUNGRIFDFFUCOH-UHFFFAOYSA-N 2-(1-methylimidazol-2-yl)propanoic acid Chemical compound OC(=O)C(C)C1=NC=CN1C RUNGRIFDFFUCOH-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 description 11
- 229960004011 methenamine Drugs 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 229940073561 hexamethyldisiloxane Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/20—Purification, separation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
The invention discloses a method for adsorbing and purifying 1, 1, 1, 3, 5, 5, 5-heptamethyltrisiloxane.The method includes preparing adsorbent resin with oxo-cyclobutane; adding the adsorbent resin into an exchange column to obtain adsorbent resin products; adding a crude product 1, 1, 1, 3, 5, 5, 5-heptamethyltrisiloxane into the exchange column from the upper side of the exchange column to obtain effluent which is the purified 1, 1, 1, 3, 5, 5, 5-heptamethyltrisiloxane.
Description
Technical field
The present invention relates to the preparation method of a kind of organosilicon product, particularly a kind of absorption purifies
The method of 1,1,1,3,5,5,5-heptamethyltrisiloxane.
Background technology
Trisiloxanes class surfactant has excellent plate-out ability, wettability and impregnability, in recent years conduct
Agricultural agent is widely used in agricultural, has boundless application prospect, along with three silane
The continuous expansion of class surfactant application, 1,1,1,3,5,5,5-heptamethyltrisiloxane is as synthesis
The intermediate of the surfactant of trisiloxanes class, its synthesis and purification also seem more and more important.
CN101020691 discloses the method for synthesis 1,1,1,3,5,5,5-heptamethyltrisiloxane, and step is as follows:
To have ME3The trimethyl silicane alkanes material inorganic weak bases solution of SIX formula is hydrolyzed, then to hydrolysis body
System is slowly added dropwise there is MESIHX2The methylhydrosiloxane class material of formula, be hydrolyzed under stirring condensation reaction,
Reaction temperature is-5～20 DEG C, and time for adding controls 1～4H, X=CL in above-mentioned two formulas, BR, I, OME,
OET, ME3SIX and MESIHX2Volume parts ratio be 150: 20～150: 110, drip complete, oil phase is through water
Wash, be dried, rectification, obtain product.
The open one of CN104004010A uses solid super-strong acid to prepare 1,1,1,3,5,5,5-seven methyl three silicon
The new method of oxygen alkane.The method is that to use high containing hydrogen silicone oil and hexamethyl disiloxane be raw material, its mass ratio
Being 3～10: 1, under the catalysis of solid super-strong acid, reaction temperature is 50～90 DEG C, carries out still reaction,
Response time is 5～9 hours, produces 1,1,1,3,5,5,5-heptamethyltrisiloxane, to reacted product
Thing carries out rectification, obtains the purity product more than 99.3%.
Existing patent and the used purifying technique of technical literature, all use distillation or the technique of evaporation, and energy consumption is high,
Equipment investment is big, is unfavorable for industrialized production.
Summary of the invention
In order to solve above technical problem, present invention employs following technical scheme: a kind of absorption purifies
The method of 1,1,1,3,5,5,5-heptamethyltrisiloxane, comprises the following steps:
Step 1. aminating reaction
Macropore Chloromethyl polystyrene reacts with hexamethylenamine, obtains primary amine resin.
By weight, 100 parts of chloromethylation balls of addition in stirred tank, 50-100 part hexamethylenetetramine,
50-100 part pure water, is warming up to 60-100 DEG C, is incubated 5-15h, filters, and blowing is weighed, and obtains primary amine groups
Resin.
Step 2 carboxylic acid reaction
By weight, stirred tank adds 100 parts of primary amine groups resins, 200-400 part 3-oxo ring fourth
Alkyl carboxylic acid, 10-40 part nervonie acid, 0.01-0.1 part 1-carboxyethyl-3-Methylimidazole.
Villaumite and 100-400 part water, be warming up to 50-80 DEG C, is incubated 30-60h, obtains adsorbent resin.
Step 3, the purification of 1,1,1,3,5,5,5-heptamethyltrisiloxane
By weight, exchange column adds step 2 and obtain adsorbent resin product 100 parts, by crude product
1,1,1,3,5,5,5-heptamethyltrisiloxane adds above exchange column, flow velocity 50-150L/h, and effluent is i.e.
For 1 after purification, 1,1,3,5,5,5-heptamethyltrisiloxane.
1-chloro-4-methyl-benzene described in step 1 be commercially available prod be commercially available prod, such as Linchuan, Changzhou Wujin
The product that work company limited produces；Hexamethylenetetramine described in step 1 is commercially available prod, such as Guangzhou
The product that Gui Hua Science and Technology Ltd. produces.
3-oxo Tetramethylene. yl carboxylic acid described in step 2 is commercially available prod, as Changzhou edifies the limited public affairs of chemical industry
The product that department produces；1-carboxyethyl-3-Methylimidazole. villaumite described in step 1, commercially available prod, such as middle section
Institute's Lanzhou Chemical Physics institute produces product；Nervonie acid described in step 2 is commercially available
Product, the product produced such as source, Shanghai leaf biology company limited.
In the present invention 1,1,1,3,5,5,5-heptamethyltrisiloxane crude product is commercially available prod, such as Shanghai Jin Jin
Happy Industrial Co., Ltd. product.
Compared with prior art, the method have the advantages that
1, resin adsorption method technique is simple, and flow process is short, and equipment investment is few.
2, containing oxo Tetramethylene. base in adsorbent resin skeleton, it is low point of main component to polydimethylcyclosil.xane
The adsorbance of sub-thing improves；And the intensity making resin improves.
3, product low molecule adsorption rate is more than 80%, reaches as high as 95%.
Detailed description of the invention
Below in conjunction with specific embodiment, it is further elucidated with the present invention, but these embodiments are only used for explaining this
Bright rather than be used for limiting the scope of the present invention.
In embodiment 1,1,1,3,5,5,5-heptamethyltrisiloxane crude material is that Jin Jin happy industry in Shanghai has
Limit Products.
Embodiment 1
Step 1. aminating reaction
Addition 100Kg chloromethylation ball in 500L reactor, 80Kg hexamethylenetetramine, 80Kg pure water,
Reacting 12h at 80 DEG C, reaction is filtered after terminating, and blowing obtains primary amine groups resin after drying.
Step 2. carboxylic acid reaction
100Kg primary amine groups resin, 300Kg3-oxo Tetramethylene. yl carboxylic acid, 20Kg is added in 1000L reactor
Nervonie acid, 0.05Kg1-carboxyethyl-3-Methylimidazole. villaumite, 300Kg water, anti-at 60 DEG C
Answer 50h, obtain adsorbent resin.
Step 3. 1,1, the purification of 1,3,5,5,5-heptamethyltrisiloxane
In 500L exchange column, add the adsorbent resin product that 100Kg step 2 obtains, by crude product
1,1,1,3,5,5,5-heptamethyltrisiloxane adds above exchange column, flow velocity 100L/h, and effluent is
1 after purification, 1,1,3,5,5,5-heptamethyltrisiloxane.Adsorption rate is shown in Table 1.
Embodiment 2
Step 1. aminating reaction
Addition 100Kg chloromethylation ball in 500L reactor, 50Kg hexamethylenetetramine, 80Kg pure water,
Reacting 10h at 80 DEG C, reaction is filtered after terminating, and blowing obtains primary amine groups resin after drying.
Step 2. carboxylic acid reaction
100Kg primary amine groups resin, 200Kg3-oxo Tetramethylene. yl carboxylic acid, 10Kg is added in 1000L reactor
Nervonie acid, 0.01Kg1-carboxyethyl-3-Methylimidazole. villaumite, 300Kg water, anti-at 60 DEG C
Answer 30h, obtain adsorbent resin.
Step 3. 1,1, the purification of 1,3,5,5,5-heptamethyltrisiloxane
In 500L exchange column, add the adsorbent resin product that 100Kg step 2 obtains, by crude product
1,1,1,3,5,5,5-heptamethyltrisiloxane adds above exchange column, flow velocity 50L/h, and effluent is pure
After change 1,1,1,3,5,5,5-heptamethyltrisiloxane.Adsorption rate is shown in Table 1.
Embodiment 3
Step 1. aminating reaction
Addition 100Kg chloromethylation ball in 500L reactor, 100Kg hexamethylenetetramine, 80Kg pure water,
Reacting 10h at 80 DEG C, reaction is filtered after terminating, and blowing obtains primary amine groups resin after drying.
Step 2. carboxylic acid reaction
100Kg primary amine groups resin, 400Kg3-oxo Tetramethylene. yl carboxylic acid, 50Kg is added in 1000L reactor
Nervonie acid, 0.1Kg1-carboxyethyl-3-Methylimidazole. villaumite, 300Kg water, anti-at 60 DEG C
Answer 60h, obtain adsorbent resin.
Step 3. 1,1, the purification of 1,3,5,5,5-heptamethyltrisiloxane
In 500L exchange column, add the adsorbent resin product that 100Kg step 2 obtains, by crude product
1,1,1,3,5,5,5-heptamethyltrisiloxane adds above exchange column, flow velocity 150L/h, and effluent is
1 after purification, 1,1,3,5,5,5-heptamethyltrisiloxane.Adsorption rate is shown in Table 1.
Comparative example 1
Step 2 is added without nervonie acid, the other the same as in Example 1, and adsorption rate is shown in Table 1.
Comparative example 2
Step 2 is added without 1-carboxyethyl-3-Methylimidazole. villaumite, and the other the same as in Example 1, adsorption rate is shown in Table 1.
The detection of embodiment 4 low molecule adsorption rate
Low molecule adsorption rate=(1,1,1,3,5,5,5-heptamethyltrisiloxane low molecule content-purification before purification
Rear 1,1,1,3,5,5,5-heptamethyltrisiloxane low molecule content)/1,1,1,3,5,5,5-seven first before purification
Base trisiloxanes low molecule content.
Table 1: the low molecule adsorption rate of embodiment 1-3 and comparative example 1-2 is shown in Table 1.
| Embodiment | Low molecule adsorption rate is shown in % |
| 1 | 90 |
| 2 | 84 |
| 3 | 97 |
| Comparative example 1 | 74 |
| Comparative example 2 | 72 |
Claims (1)
1. the method for absorption purification 1,1,1,3,5,5, a 5-heptamethyltrisiloxane, it is characterised in that described
Preparation method comprises the following steps:
Step 1. aminating reaction
By weight, 100 parts of chloromethylation balls of addition in stirred tank, 50-100 part hexamethylenetetramine,
50-100 part pure water, is warming up to 60-100 DEG C, is incubated 5-15h, filters, and blowing is weighed, and obtains primary amine groups
Resin；
Step 2 carboxylic acid reaction
By weight, stirred tank adds 100 parts of primary amine groups resins, 200-400 part 3-oxo ring fourth
Alkyl carboxylic acid, 10-40 part nervonie acid, 0.01-0.1 part 1-carboxyethyl-3-Methylimidazole.
Villaumite and 100-400 part water, be warming up to 50-80 DEG C, is incubated 30-60h, obtains adsorbent resin；
Step 3, the purification of 1,1,1,3,5,5,5-heptamethyltrisiloxane
By weight, exchange column adds step 2 and obtain adsorbent resin product 100 parts, by crude product
1,1,1,3,5,5,5-heptamethyltrisiloxane adds above exchange column, and effluent is after purification
1,1,1,3,5,5,5-heptamethyltrisiloxane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610139441.9A CN105732694B (en) | 2016-03-04 | 2016-03-04 | A kind of method that absorption purifies 1,1,1,3,5,5,5- heptamethyltrisiloxane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610139441.9A CN105732694B (en) | 2016-03-04 | 2016-03-04 | A kind of method that absorption purifies 1,1,1,3,5,5,5- heptamethyltrisiloxane |
Publications (2)
| Publication Number | Publication Date |
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| CN105732694A true CN105732694A (en) | 2016-07-06 |
| CN105732694B CN105732694B (en) | 2018-07-13 |
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| CN201610139441.9A Active CN105732694B (en) | 2016-03-04 | 2016-03-04 | A kind of method that absorption purifies 1,1,1,3,5,5,5- heptamethyltrisiloxane |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107512704A (en) * | 2017-04-26 | 2017-12-26 | 张玲 | A kind of method of organosilicon by-product hydrochloric acid purification |
| CN111440209A (en) * | 2020-04-27 | 2020-07-24 | 浙江新安化工集团股份有限公司 | 1,1,1,3,5,5, 5-heptamethyltrisiloxane and preparation method thereof |
| CN115591272A (en) * | 2022-10-27 | 2023-01-13 | 大连科利德光电子材料有限公司（Cn） | Method and system for purifying silicon-based precursor |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101020691A (en) * | 2007-03-13 | 2007-08-22 | 浙江大学 | Process of synthesizing 1,1,1,3,5,5,5-heptamethyl trisiloxane |
| CN104072777B (en) * | 2014-06-13 | 2017-01-25 | 王金明 | Process for purifying and refining 107 gel |
| CN104071751B (en) * | 2014-06-13 | 2016-02-10 | 王金明 | A kind of method of siloxanes in adsorbing and removing hydrochloric acid |
-
2016
- 2016-03-04 CN CN201610139441.9A patent/CN105732694B/en active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107512704A (en) * | 2017-04-26 | 2017-12-26 | 张玲 | A kind of method of organosilicon by-product hydrochloric acid purification |
| CN111440209A (en) * | 2020-04-27 | 2020-07-24 | 浙江新安化工集团股份有限公司 | 1,1,1,3,5,5, 5-heptamethyltrisiloxane and preparation method thereof |
| CN115591272A (en) * | 2022-10-27 | 2023-01-13 | 大连科利德光电子材料有限公司（Cn） | Method and system for purifying silicon-based precursor |
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