CN106243146B - Two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds and preparation method thereof - Google Patents
Two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds and preparation method thereof Download PDFInfo
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- CN106243146B CN106243146B CN201610602379.2A CN201610602379A CN106243146B CN 106243146 B CN106243146 B CN 106243146B CN 201610602379 A CN201610602379 A CN 201610602379A CN 106243146 B CN106243146 B CN 106243146B
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 title claims abstract description 56
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 title claims abstract description 56
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 239000005642 Oleic acid Substances 0.000 title claims abstract description 56
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 title claims abstract description 56
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 title claims abstract description 56
- -1 oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds Chemical class 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title claims description 52
- 238000006243 chemical reaction Methods 0.000 claims abstract description 59
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 39
- 150000002148 esters Chemical class 0.000 claims abstract description 22
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 12
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 4
- AHNBSGYALSWVOQ-UHFFFAOYSA-N COC(=O)[Sn](CC(Cl)Cl)C(=O)OC Chemical compound COC(=O)[Sn](CC(Cl)Cl)C(=O)OC AHNBSGYALSWVOQ-UHFFFAOYSA-N 0.000 claims description 45
- 239000000543 intermediate Substances 0.000 claims description 43
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 37
- 238000003756 stirring Methods 0.000 claims description 36
- 239000003054 catalyst Substances 0.000 claims description 31
- 239000011521 glass Substances 0.000 claims description 30
- CGOSCPFIHGMPHN-UHFFFAOYSA-N COC(=O)[Sn](CC)C(=O)OC Chemical compound COC(=O)[Sn](CC)C(=O)OC CGOSCPFIHGMPHN-UHFFFAOYSA-N 0.000 claims description 20
- 239000007789 gas Substances 0.000 claims description 20
- 230000035484 reaction time Effects 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 14
- 238000005660 chlorination reaction Methods 0.000 claims description 13
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 12
- 238000007664 blowing Methods 0.000 claims description 12
- 210000003298 dental enamel Anatomy 0.000 claims description 12
- 230000032050 esterification Effects 0.000 claims description 12
- 238000005886 esterification reaction Methods 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- 239000012074 organic phase Substances 0.000 claims description 12
- 239000011265 semifinished product Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 11
- 238000005292 vacuum distillation Methods 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000004202 carbamide Substances 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 7
- 239000003456 ion exchange resin Substances 0.000 claims description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 7
- ZCYZVNPFLTXYPE-KVVVOXFISA-N SC(C)O.C(CCCCCCC\C=C/CCCCCCCC)(=O)O Chemical class SC(C)O.C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZCYZVNPFLTXYPE-KVVVOXFISA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- 239000003643 water by type Substances 0.000 claims description 4
- 235000019441 ethanol Nutrition 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- 238000005070 sampling Methods 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 2
- GHKCSRZBNZQHKW-UHFFFAOYSA-N 1-sulfanylethanol Chemical class CC(O)S GHKCSRZBNZQHKW-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 125000004185 ester group Chemical group 0.000 abstract description 4
- 229920002521 macromolecule Polymers 0.000 abstract description 2
- 239000003381 stabilizer Substances 0.000 abstract description 2
- 125000002347 octyl 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])[H] 0.000 description 8
- 229910001868 water Inorganic materials 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 4
- 230000036632 reaction speed Effects 0.000 description 4
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- NLOMWWAGCXLRQK-UHFFFAOYSA-N COC(=O)[Sn](CC)C(=O)OC.[Cl] Chemical compound COC(=O)[Sn](CC)C(=O)OC.[Cl] NLOMWWAGCXLRQK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- WTHDKMILWLGDKL-UHFFFAOYSA-N urea;hydrate Chemical compound O.NC(N)=O WTHDKMILWLGDKL-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 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
- C07F7/22—Tin compounds
- C07F7/226—Compounds with one or more Sn-S linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds, molecular formula is：
Description
Technical field：
The present invention relates to a kind of travel notes tin compound and preparation method thereof, more particularly, is related to a kind of two oleic acid sulfydryl second
Base alcohol ester dimethoxycarbonyl ethyl tin compound and preparation method thereof.
Background technology：
It is by the way that resin is heated when halo ethylene resin and the composition containing halo ethylene resin are converted to product at present
Softening or the mode melted are transformed into melt substance with thermoforming to form product, that is, by powdered resin composition, then
Required shape is obtained through extrusion forming.Heat is produced by the friction occurred in compound in this course, softens halogen ethene
Heat needed for resin combination is different and different with composition, but typically between 165-210 DEG C.Halo ethylene resin higher than
To be degraded under conditions of 100 DEG C, and degraded can cause the discoloration of halogen ethene and physical property to be lost, or even meeting blackening becomes fragile down to not
Can use, in order to solve these problems, people have done a variety of effort, as Chinese patent 93118446.0 disclose one it is organic
The patent of tin stable compound and its preparation method and application, belong to the heat stabilizer of halo ethylene resin, can suppress to colour in early days,
With UV resistant and long-term thermal stability.But the problem of existing is that the cost of product is high, and raw material sources are not extensive, solve this
One problem turns into and is badly in need of.
The content of the invention
An object of the present invention is to provide a kind of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds.
The second object of the present invention is to provide a kind of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compound
Preparation method.
The these and other objects of the present invention will further embody by the following detailed description and explanation.
The two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds of the present invention, molecular formula are：
The preparation method of the two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds of the present invention, including following step
Suddenly：
A. the preparation of dichloro dimethoxycarbonyl ethyl tin compound intermediate
The methyl acrylate that will be measured, concentrated hydrochloric acid and catalyst are added in chlorination enamel reaction still, stirring are started, while stirring
Mix side and add glass putty, the mesh number of glass putty is：400 mesh, while dry hydrogen chloride gas is passed through, controlling reaction temperature 50-85
DEG C, after glass putty completely reaction, the solids that cools, filter white, its composition is dichloro dimethoxycarbonyl ethyl tin chemical combination
Thing intermediate, the methyl acrylate for removing excess residual is then washed with 0.5-4 mass % aqueous solution of urea, refilters, do
It is dry to obtain pure dichloro dimethoxycarbonyl ethyl tin compound intermediate；
B. the preparation of oleic acid mercaptoethanol ester
By 2 mercapto ethanol, oleic acid, catalyst is added in reaction kettle of the esterification, is heated while stirring, when temperature is heated to 55-
At 70 DEG C, 1-4 hours are reacted, obtain semi-finished product；Then 80-90 DEG C is again heated to, under condition of negative pressure, controls this temperature to keep
1-3 hour obtains oleic acid mercaptoethanol ester；
C. the preparation of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds
By dichloro dimethoxycarbonyl ethyl tin compound intermediate made from A, step B, oleic acid mercaptoethanol ester, ammoniacal liquor,
Deionized water and catalyst are added in synthesis reactor, and controlling reaction temperature is 60-70 DEG C, reacts 1-3 hours, then blowing, layering,
Organic phase is evaporated under reduced pressure again, the control condition of vacuum distillation is temperature：80-95 DEG C, negative pressure：0.05-0.90MPa,
Reaction time：3-4 hours, the final products for then cooling, filtering.
It is an option that the preparation side of the two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds of the present invention
Method, comprise the following steps：
A. the preparation of dichloro dimethoxycarbonyl ethyl tin compound intermediate
The methyl acrylate that will be measured, concentrated hydrochloric acid and catalyst are added in chlorination enamel reaction still, stirring are started, while stirring
Mix side and add glass putty, the mesh number of glass putty is：400 mesh, while dry hydrogen chloride gas is passed through, controlling reaction temperature 50-85
DEG C, after glass putty completely reaction, the solids that cools, filter white, its composition is dichloro dimethoxycarbonyl ethyl tin chemical combination
Thing intermediate, the methyl acrylate for removing excess residual is then washed with 0.5-2.5 mass % aqueous solution of urea, refilter,
Dry pure dichloro dimethoxycarbonyl ethyl tin compound intermediate；
B. the preparation of oleic acid mercaptoethanol ester
By 2 mercapto ethanol, oleic acid, catalyst is added in reaction kettle of the esterification, is heated while stirring, when temperature is heated to 60-
At 75 DEG C, 1.5-2.5 hours are reacted, obtain semi-finished product；Then 80-90 DEG C is again heated to, under condition of negative pressure, controls this temperature
Kept for 1.5-3 hour obtain oleic acid mercaptoethanol ester；
C. the preparation of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds
By dichloro dimethoxycarbonyl ethyl tin compound intermediate made from A, step B, oleic acid mercaptoethanol ester, ammoniacal liquor,
Deionized water and catalyst are added in synthesis reactor, and controlling reaction temperature is 60-65 DEG C, are reacted 1.5 hours, then blowing, layering,
Organic phase is evaporated under reduced pressure again, the control condition of vacuum distillation is temperature：80-95 DEG C, negative pressure：0.08-0.5MPa, instead
Between seasonable：3-4 hours, the final products for then cooling, filtering.
The preparation method of the two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds of the present invention, including following step
Suddenly：
A. the preparation of dichloro dimethoxycarbonyl ethyl tin compound intermediate
By 60-120 kilograms of methyl acrylate, 1-3 kilograms of concentrated hydrochloric acid and 0.1-1.0 kg catalysts add chlorination and warded off
In porcelain reactor, stirring is started, adds 50-80 kilograms of glass putty while stirring, the mesh number of glass putty is：400 mesh, while it is passed through drying
30-70 kilograms of hydrogen chloride gas, controlling reaction temperature be 50-85 DEG C, after glass putty completely reaction after, cool, filter white
Solids, its composition is dichloro dimethoxycarbonyl ethyl tin compound intermediate, then with 0.5-2.5 mass % urea water
Solution 20kg washings remove the methyl acrylate of excess residual, refilter, dry pure dichloro dimethoxycarbonyl ethyl tin
Compound intermediate；
B. the preparation of oleic acid mercaptoethanol ester
By 40-60 kilograms of 2 mercapto ethanol, 160-200 kilograms of oleic acid, 2-5 kg catalysts are added in reaction kettle of the esterification,
Heat while stirring, when temperature is heated to 60-75 DEG C, reacts 1.5-2.5 hours, obtain semi-finished product；Then it is again heated to 80-
90 DEG C, under condition of negative pressure, this temperature is controlled to be kept for 1.5-3 hour obtain oleic acid mercaptoethanol ester；
C. the preparation of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds
By 80-120 kilograms of dichloro dimethoxycarbonyl ethyl tin compound intermediate made from A, step B, 180-220 kilograms
Oleic acid mercaptoethanol ester, deionized water 80-120kg, 60-100 kilograms of content 10-20% ammoniacal liquor and 0.5 kg catalyst add
Enter in synthesis reactor, controlling reaction temperature is 60-65 DEG C, is reacted 1.5 hours, then blowing, layering, organic phase is depressurized again
Distillation, the control condition of vacuum distillation is temperature：80-95 DEG C, negative pressure：0.08-0.1MPa, reaction time：3-4 hours, so
The final products for cooling afterwards, filtering.
It is preferred that the preparation method of the two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds of the present invention,
Comprise the following steps：
A. the preparation of dichloro dimethoxycarbonyl ethyl tin compound intermediate
By 80-100 kilograms of methyl acrylate, 1.5-2.5 kilograms of concentrated hydrochloric acid and 0.5 kg catalyst add chlorination and warded off
In porcelain reactor, stirring is started, adds 55-70 kilograms of glass putty while stirring, the mesh number of glass putty is：400 mesh, while it is passed through drying
44 kilograms of hydrogen chloride gas, controlling reaction temperature is 50-85 DEG C, after glass putty completely reaction, is cooled, consolidating of filtering white
Body thing, its composition is dichloro dimethoxycarbonyl ethyl tin compound intermediate, then with 0.5-2.5 mass % aqueous solution of urea
21kg washings remove the methyl acrylate of excess residual, refilter, dry pure dichloro dimethoxycarbonyl ethyl tin chemical combination
Thing intermediate；
B. the preparation of oleic acid mercaptoethanol ester
By 45-55 kilograms of 2 mercapto ethanol, 170-190 kilograms of oleic acid, 3-4 kg catalysts are added in reaction kettle of the esterification,
Heat while stirring, when temperature is heated to 60-75 DEG C, reacts 1.5-2.5 hours, obtain semi-finished product；Then it is again heated to 80-
90 DEG C, under condition of negative pressure, this temperature is controlled to be kept for 1.5-3 hour obtain oleic acid mercaptoethanol ester；
C. the preparation of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds
By 90-100 kilograms of dichloro dimethoxycarbonyl ethyl tin compound intermediate made from A, step B, 190-210 kilograms
Oleic acid mercaptoethanol ester, deionized water 100kg, 70-90 kilograms of content 10-20% ammoniacal liquor and 0.5 kg catalyst, which add, to be closed
Into in kettle, controlling reaction temperature is 60-65 DEG C, is reacted 1.5 hours, then blowing, layering, decompression steaming is carried out by organic phase again
Evaporate, the control condition of vacuum distillation is temperature：80-95 DEG C, negative pressure：0.08-0.1MPa, reaction time：3-4 hours, then
Cooling, the final products of filtering.
It is described in the preparation method of the two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds of the present invention
A diameter of DN100 of chlorination enamel reaction still, cylinder height：4000mm, inside there are hydrogen chloride gas body canal 3850mm, mixing speed
For 450 revs/min, and there is sampling observation panel, thermometer mouth and gauge port.
It is described in the preparation method of the two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds of the present invention
Catalyst is AlCl3、FeCl3, ion exchange resin：732 types or 213 types.
It is preferred that the preparation method of the two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds of the present invention,
Molecular formula is：
It is prepared as follows：
A, the preparation of dichloro dimethoxycarbonyl ethyl tin compound intermediate
By 92 kilograms of methyl acrylates, the concentrated hydrochloric acid and 0.5 kg catalyst AlCl that 2 kilograms of concentration are 31%3Add chlorine
Change in enamel reaction still, start stirring, add 60 kilograms of glass puttys while stirring, while be passed through dry hydrogen chloride gas 37kg,
This gas is passed through reactor bottom, and controlling reaction temperature is 60 DEG C, 3 hours of reaction time, after glass putty completely reaction, drop
Temperature, the solids for filtering white, its composition are：Dichloro dimethoxycarbonyl ethyl tin compound intermediate, then with 1% urine
The methyl acrylates of 20 kilograms of washing excess residuals of the plain aqueous solution, refilter, dry pure dichloro dimethoxycarbonyl ethyl
Tin compound intermediate 132.1KG, yield 95%.
B, the preparation of oleic acid mercaptoethanol ester：
By 50 kilograms of 2 mercapto ethanol (contents：99%, technical grade), 181 kilograms of oleic acid (contents：99%, technical grade),
The concentrated sulfuric acid that 3.5 kilograms of contents are 93% is added in reaction kettle of the esterification, is heated while stirring, when temperature is heated to 65 DEG C, instead
It is 2.2 hours between seasonable, obtains semi-finished product, be then again heated to 85 DEG C ,-the 0.096MPa under condition of negative pressure, control this temperature
Kept for 2 hours, then cool, filter to obtain oleic acid mercaptoethanol ester 215KG, yield 98%.
C. the preparation of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds
By 100 kilograms of dichloro dimethoxycarbonyl ethyl tin compound intermediates, 206 kilograms of oleic acid mercaptoethanol esters, content
For 17% 80 kilograms of ammoniacal liquor, 100 kilograms of deionized waters and ion exchange resin：213 type catalyst are added in synthesis reactor, control reaction
65 DEG C of temperature, react 1.5 hours, then blowing, layering, organic phase are evaporated under reduced pressure again, the control strip of vacuum distillation
Part is：Temperature：85-90℃；Negative pressure：-0.098MPa；Reaction time：3.5 hours, then cool, filter, obtain two oleic acid mercaptos
Base ethyl alcohol ester dimethoxycarbonyl ethyl tin compound 281KG, yield 96.5%.
Technical solution of the present invention quotes oleic acid synthesis (inverse) Ester-tin Compounds, due to the change of (inverse) ester group structure,
The activity increase of (inverse) ester group, make its as stabilizer early stage stability more preferably, then due to the oil containing macromolecule in ester
Acid, make its slip more excellent, there is the effect that traditional organotin can not possess.And unique equipment and technique are used, instead
Answer effect more preferable, it is more efficient, there is more preferable application prospect.
In order to make the purpose , technical scheme and advantage of the present invention be clearer, with reference to embodiments, to the present invention
It is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, it is not used to
Limit the present invention.
In the present invention, refered in particular to as non-, all amounts, part are unit of weight, and all raw material can be from market
Buy.
Embodiment
Embodiment 1
Prepare two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds of following molecular formula：
It is prepared as follows：
A, the preparation of dichloro dimethoxycarbonyl ethyl tin compound intermediate
Sn+2CH2=CHCOOCH3+2HCL→(CH3COOCCH2CH2)2SnCL2
By 92 kilograms of methyl acrylates, (content is：99.0%, technical grade), the concentrated hydrochloric acid and 0.5 that 2 kilograms of concentration are 31%
Kg catalyst AlCl3Add in chlorination enamel reaction still, start stirring, (content is 60 kilograms of glass puttys of addition while stirring：
99.99%, technical grade, mesh number is：400 mesh), while dry hydrogen chloride gas 37kg is passed through, this gas is passed through reactor bottom
Portion, to improve reaction speed, controlling reaction temperature is 60 DEG C, 3 hours of reaction time, (the sampling after glass putty completely reaction
Observing response situation), the solids for cooling, filtering white, its composition is：Among dichloro dimethoxycarbonyl ethyl tin compound
Body, then with 1% 20 kilograms of aqueous solution of urea washing excess residual methyl acrylates, refilter, dry pure two
Chlorine dimethoxycarbonyl ethyl tin compound intermediate 132.1KG, yield 95%；
B, the preparation of oleic acid mercaptoethanol ester：
HOCH2CH2SH+CH3(CH2) 7CH=CH (CH2)7COOH→
HSCH2CH2COO(CH2) 7CH=CH (CH2)7CH3+H20
By 50 kilograms of 2 mercapto ethanol (contents：99%, technical grade), 181 kilograms of oleic acid (contents：99%, technical grade),
The concentrated sulfuric acid that 3.5 kilograms of contents are 93% is added in reaction kettle of the esterification, is heated while stirring, when temperature is heated to 65 DEG C, instead
It is 2.2 hours between seasonable, obtains semi-finished product, be then again heated to 85 DEG C ,-the 0.096MPa under condition of negative pressure, control this temperature
Kept for 2 hours, then cool, filter to obtain oleic acid mercaptoethanol ester 215KG, yield 98%.
C, the preparation of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds
(CH3COOCCH2CH2)2SnCL2+2HSCH2CH2COO(CH2) 7CH=CH (CH2)7CH3+2NH3.H2O→
By 100 kilograms of dichloro dimethoxycarbonyl ethyl tin compound intermediates, 206 kilograms of oleic acid mercaptoethanol esters, content
For 17% 80 kilograms of ammoniacal liquor, 100 kilograms of deionized waters and 0.5 kilogram of ion exchange resin：213 type catalyst are added in synthesis reactor,
65 DEG C of controlling reaction temperature, react 1.5 hours, then blowing, layering, organic phase is evaporated under reduced pressure again, vacuum distillation
Control condition be：Temperature：85-90℃；Negative pressure：-0.098MPa；Reaction time：3.5 hours, then cool, filter, obtain
Two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compound 281KG, yield 96.5%.
Embodiment 2
Prepare two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds of following molecular formula：
It is prepared as follows：
A, the preparation of dichloro dimethoxycarbonyl ethyl tin compound intermediate
Sn+2CH2=CHCOOCH3+2HCL→(CH3COOCCH2CH2)2SnCL2
By 65 kilograms of methyl acrylates, (content is：99.0%, technical grade), the concentrated hydrochloric acid and 0.3 that 1 kilogram of concentration is 31%
Kg catalyst AlCl3Add in chlorination enamel reaction still, start stirring, (content is 50 kilograms of glass puttys of addition while stirring：
99.99%, technical grade, mesh number is：400 mesh), while dry hydrogen chloride gas 30kg is passed through, this gas is passed through reactor bottom
Portion, to improve reaction speed, controlling reaction temperature is 50 DEG C, 2.5 hours of reaction time, (is taken after glass putty completely reaction
Sample observing response situation), the solids for cooling, filtering white, its composition is：In dichloro dimethoxycarbonyl ethyl tin compound
Mesosome, then with 1% 20 kilograms of aqueous solution of urea washing excess residual methyl acrylates, refilter, be purely dry
Dichloro dimethoxycarbonyl ethyl tin compound intermediate 102.1KG, yield 94%；
B, the preparation of oleic acid mercaptoethanol ester：
HOCH2CH2SH+CH3(CH2) 7CH=CH (CH2)7COOH→
HSCH2CH2COO(CH2) 7CH=CH (CH2)7CH3+H20
By 40 kilograms of 2 mercapto ethanol (contents：99%, technical grade), 161 kilograms of oleic acid (contents：99%, technical grade),
The concentrated sulfuric acid that 2.5 kilograms of contents are 93% is added in reaction kettle of the esterification, is heated while stirring, when temperature is heated to 65 DEG C, instead
It is 1.6 hours between seasonable, obtains semi-finished product, be then again heated to 82 DEG C ,-the 0.096MPa under condition of negative pressure, control this temperature
Kept for 2 hours, then cool, filter to obtain oleic acid mercaptoethanol ester 185KG, yield 98%.
C, the preparation of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds
(CH3COOCCH2CH2)2SnCL2+2HSCH2CH2COO(CH2) 7CH=CH (CH2)7CH3+2NH3.H2O→
It is by 80 kilograms of dichloro dimethoxycarbonyl ethyl tin compound intermediates, 186 kilograms of oleic acid mercaptoethanol esters, content
17% 60 kilograms of ammoniacal liquor, 80 kilograms of deionized waters and 0.3 kilogram of ion exchange resin：213 type catalyst are added in synthesis reactor, control
65 DEG C of reaction temperature, react 1.5 hours, then blowing, layering, organic phase are evaporated under reduced pressure again, the control of vacuum distillation
Condition processed is：Temperature：85-90℃；Negative pressure：-0.098MPa；Reaction time：3.5 hours, then cool, filter, obtain two oil
Sour mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compound 201KG, yield 96.5%.
Embodiment 3
Prepare two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds of following molecular formula：
It is prepared as follows：
A, the preparation of dichloro dimethoxycarbonyl ethyl tin compound intermediate
Sn+2CH2=CHCOOCH3+2HCL→(CH3COOCCH2CH2)2SnCL2
By 115 kilograms of methyl acrylates, (content is：99.0%, technical grade), concentrated hydrochloric acid that 2.8 kilograms of concentration are 31% and
0.9 kg catalyst FeCl3Add in chlorination enamel reaction still, start stirring, add 80 kilograms of glass putty (contents while stirring
For：99.99%, technical grade, mesh number is：400 mesh), while dry hydrogen chloride gas 60kg is passed through, this gas is passed through reactor
Bottom, to improve reaction speed, controlling reaction temperature is 80 DEG C, 3 hours of reaction time, (is taken after glass putty completely reaction
Sample observing response situation), the solids for cooling, filtering white, its composition is：In dichloro dimethoxycarbonyl ethyl tin compound
Mesosome, then with 1% 24 kilograms of aqueous solution of urea washing excess residual methyl acrylates, refilter, be purely dry
Dichloro dimethoxycarbonyl ethyl tin compound intermediate 189.1KG, yield 96%；
B, the preparation of oleic acid mercaptoethanol ester：
HOCH2CH2SH+CH3(CH2) 7CH=CH (CH2)7COOH→
HSCH2CH2COO(CH2) 7CH=CH (CH2)7CH3+H20
By 60 kilograms of 2 mercapto ethanol (contents：99%, technical grade), 191 kilograms of oleic acid (contents：99%, technical grade),
The concentrated sulfuric acid that 4.5 kilograms of contents are 93% is added in reaction kettle of the esterification, is heated while stirring, when temperature is heated to 70 DEG C, instead
It is 2.5 hours between seasonable, obtains semi-finished product, be then again heated to 85 DEG C ,-the 0.096MPa under condition of negative pressure, control this temperature
Kept for 2.5 hours, then cool, filter to obtain oleic acid mercaptoethanol ester 255KG, yield 98%.
C, the preparation of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds
(CH3COOCCH2CH2)2SnCL2+2HSCH2CH2COO(CH2) 7CH=CH (CH2)7CH3+2NH3.H2O→
By 120 kg dichloro dimethoxycarbonyl ethyl tin compound intermediate, 210 kilograms of oleic acid mercaptoethanol esters, content
For 20% 80 kilograms of ammoniacal liquor, 120 kg deionized water and 0.8 kilogram of type catalyst of ion exchange resin 732 are added in synthesis reactor, control
65 DEG C of reaction temperature processed, react 1.5 hours, then blowing, layering, organic phase is evaporated under reduced pressure again, vacuum distillation
Control condition is：Temperature：85-90℃；Negative pressure：-0.098MPa；Reaction time：3.5 hours, then cool, filter, obtain two
Oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compound 315KG, yield 96.5%.
Embodiment 4
Prepare two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds of following molecular formula：
It is prepared as follows：
A, the preparation of dichloro dimethoxycarbonyl ethyl tin compound intermediate
Sn+2CH2=CHCOOCH3+2HCL→(CH3COOCCH2CH2)2SnCL2
By 96 kilograms of methyl acrylates, (content is：99.0%, technical grade), concentrated hydrochloric acid that 1.9 kilograms of concentration are 31% and
0.45 kg catalyst AlCl3Add in chlorination enamel reaction still, start stirring, add 62 kilograms of glass putty (contents while stirring
For：99.99%, technical grade, mesh number is：400 mesh), while dry hydrogen chloride gas 40kg is passed through, this gas is passed through reactor
Bottom, to improve reaction speed, controlling reaction temperature is 60 DEG C, 3 hours of reaction time, (is taken after glass putty completely reaction
Sample observing response situation), the solids for cooling, filtering white, its composition is：In dichloro dimethoxycarbonyl ethyl tin compound
Mesosome, then with 1% 20 kilograms of aqueous solution of urea washing excess residual methyl acrylates, refilter, be purely dry
Dichloro dimethoxycarbonyl ethyl tin compound intermediate 135.2KG, yield 95.8%；
B, the preparation of oleic acid mercaptoethanol ester：
HOCH2CH2SH+CH3(CH2) 7CH=CH (CH2)7COOH→
HSCH2CH2COO(CH2) 7CH=CH (CH2)7CH3+H20
By 55 kilograms of 2 mercapto ethanol (contents：99%, technical grade), 195 kilograms of oleic acid (contents：99%, technical grade),
The concentrated sulfuric acid that 3.6 kilograms of contents are 93% is added in reaction kettle of the esterification, is heated while stirring, when temperature is heated to 65 DEG C, instead
It is 2.2 hours between seasonable, obtains semi-finished product, be then again heated to 85 DEG C ,-the 0.096MPa under condition of negative pressure, control this temperature
Kept for 2 hours, then cool, filter to obtain oleic acid mercaptoethanol ester 225KG, yield 98%.
C, the preparation of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds
(CH3COOCCH2CH2)2SnCL2+2HSCH2CH2COO(CH2) 7CH=CH (CH2)7CH3+2NH3.H2O→
By 105 kg dichloro dimethoxycarbonyl ethyl tin compound intermediate, 216 kilograms of oleic acid mercaptoethanol esters, content
For 17% 85 kilograms of ammoniacal liquor, 105 kg deionized water and 0.55 kilogram of type catalyst of ion exchange resin 213 are added in synthesis reactor,
65 DEG C of controlling reaction temperature, react 1.5 hours, then blowing, layering, organic phase is evaporated under reduced pressure again, vacuum distillation
Control condition be：Temperature：85-90℃；Negative pressure：-0.098MPa；Reaction time：3.5 hours, then cool, filter, obtain
Two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compound 290KG, yield 96.5%.
Claims (4)
1. a kind of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds, it is characterised in that molecular formula is：
Carry out as follows：
A. the preparation of dichloro dimethoxycarbonyl ethyl tin compound intermediate
60-120 kilograms of methyl acrylate, 1-3 kilograms of concentrated hydrochloric acid and 0.1-1.0 kg catalysts addition chlorination enamel is anti-
Answer in kettle, start stirring, add 50-80 kilograms of glass putty while stirring, the mesh number of glass putty is：400 mesh, while be passed through dry
30-70 kilograms of hydrogen chloride gas, controlling reaction temperature are 50-85 DEG C, after glass putty completely reaction, cool, filter white
Solids, its composition are dichloro dimethoxycarbonyl ethyl tin compound intermediate, and then the urea with 0.5-2.5 mass % is water-soluble
Liquid 20kg washings remove the methyl acrylate of excess residual, refilter, dry pure dichloro dimethoxycarbonyl ethyl tin
Compound intermediate；
B. the preparation of oleic acid mercaptoethanol ester
By 40-60 kilograms of 2 mercapto ethanol, 160-200 kilograms of oleic acid, 2-5 kg catalysts are added in reaction kettle of the esterification, while stirring
Side heating is mixed, when temperature is heated to 60-75 DEG C, 1.5-2.5 hours is reacted, obtains semi-finished product；Then it is again heated to 80-90
DEG C, under condition of negative pressure, control this temperature to be kept for 1.5-3 hour obtain oleic acid mercaptoethanol ester；
C. the preparation of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds
By 80-120 kilograms of dichloro dimethoxycarbonyl ethyl tin compound intermediate, 180-220 kilograms of oleic acid made from A, step B
Mercaptoethanol ester, deionized water 80-120kg, 60-100 kilograms of content 10-20% ammoniacal liquor and 0.5 kg catalyst, which add, to be closed
Into in kettle, controlling reaction temperature is 60-65 DEG C, is reacted 1.5 hours, then blowing, layering, decompression steaming is carried out by organic phase again
Evaporate, the control condition of vacuum distillation is temperature：80-95 DEG C, negative pressure：0.08-0.1MPa, reaction time：3-4 hours, then
Cooling, the final products of filtering；
Described catalyst is AlCl3Or FeCl3。
2. the preparation method of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compound according to claim 1,
It is characterized in that comprise the following steps：
A. the preparation of dichloro dimethoxycarbonyl ethyl tin compound intermediate
By 80-100 kilograms of methyl acrylate, 1.5-2.5 kilograms of concentrated hydrochloric acid and 0.5 kg catalyst addition chlorination enamel are anti-
Answer in kettle, start stirring, add 55-70 kilograms of glass putty while stirring, the mesh number of glass putty is：400 mesh, while it is passed through dry 44
Kilogram hydrogen chloride gas, controlling reaction temperature are 50-85 DEG C, after glass putty completely reaction, the solid that cools, filter white
Thing, its composition is dichloro dimethoxycarbonyl ethyl tin compound intermediate, then with 0.5-2.5 mass % aqueous solution of urea
21kg washings remove the methyl acrylate of excess residual, refilter, dry pure dichloro dimethoxycarbonyl ethyl tin chemical combination
Thing intermediate；
B. the preparation of oleic acid mercaptoethanol ester
By 45-55 kilograms of 2 mercapto ethanol, 170-190 kilograms of oleic acid, 3-4 kg catalysts are added in reaction kettle of the esterification, while stirring
Side heating is mixed, when temperature is heated to 60-75 DEG C, 1.5-2.5 hours is reacted, obtains semi-finished product；Then it is again heated to 80-90
DEG C, under condition of negative pressure, control this temperature to be kept for 1.5-3 hour obtain oleic acid mercaptoethanol ester；
C. the preparation of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds
By 90-100 kilograms of dichloro dimethoxycarbonyl ethyl tin compound intermediate, 190-210 kilograms of oleic acid made from A, step B
Mercaptoethanol ester, deionized water 100kg, 70-90 kilograms of content 10-20% ammoniacal liquor and 0.5 kg catalyst add synthesis reactor
In, controlling reaction temperature is 60-65 DEG C, is reacted 1.5 hours, then blowing, layering, organic phase is evaporated under reduced pressure again, subtracted
The control condition of pressure distillation is temperature：80-95 DEG C, negative pressure：0.08-0.1MPa, reaction time：3-4 hours, then cool,
The final products of filtering；
Described catalyst is AlCl3Or FeCl3。
3. the preparation side of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compound according to claim 1 or 2
Method, it is characterised in that a diameter of DN100 of described chlorination enamel reaction still, cylinder height：4000mm, inside there is hydrogen chloride gas
Conduit 3850mm, mixing speed is 450 revs/min, and has sampling observation panel, thermometer mouth and gauge port.
A kind of 4. preparation method of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compound, it is characterised in that molecular formula
For：
It is prepared as follows：
A, the preparation of dichloro dimethoxycarbonyl ethyl tin compound intermediate
By 92 kilograms of methyl acrylates, the concentrated hydrochloric acid and 0.5 kilogram of AlCl that 2 kilograms of concentration are 31%3Add chlorination enamel reaction still
In, stirring is started, adds 60 kilograms of glass puttys while stirring, while dry hydrogen chloride gas 37kg is passed through, this gas is passed through instead
Bottom portion is answered, controlling reaction temperature is 60 DEG C, 3 hours of reaction time, after glass putty completely reaction, cools, filters white
Solids, its composition is：Dichloro dimethoxycarbonyl ethyl tin compound intermediate, it is then public with 1% aqueous solution of urea 20
The methyl acrylate of jin washing excess residual, is refiltered, among dry pure dichloro dimethoxycarbonyl ethyl tin compound
Body 132.1KG, yield 95%；
B, the preparation of oleic acid mercaptoethanol ester：
By 50 kilograms of 2 mercapto ethanols, 181 kilograms of oleic acid, the concentrated sulfuric acid that 3.5 kilograms of contents are 93% is added in reaction kettle of the esterification,
Heat while stirring, when temperature is heated to 65 DEG C, the reaction time is 2.2 hours, obtains semi-finished product, is then again heated to 85
DEG C ,-the 0.096MPa under condition of negative pressure, control this temperature to be kept for 2 hours, then cool, filter to obtain oleic acid mercaptoethanol ester
215KG, yield 98%；
C, the preparation of two oleic acid mercaptoethyl alcohol ester dimethoxycarbonyl ethyl tin compounds
It is by 100 kilograms of dichloro dimethoxycarbonyl ethyl tin compound intermediates, 206 kilograms of oleic acid mercaptoethanol esters, content
17% 80 kilograms of ammoniacal liquor, 100 kilograms of deionized waters, 0.5 kilogram of type of ion exchange resin 213 are added in synthesis reactor, control reaction temperature
65 DEG C of degree, react 1.5 hours, then blowing, layering, organic phase are evaporated under reduced pressure again, the control condition of vacuum distillation
For：Temperature：85-90 DEG C, negative pressure：-0.098MPa；Reaction time：3.5 hours, then cool, filter, obtain two oleic acid sulfydryls
Ethyl alcohol ester dimethoxycarbonyl ethyl tin compound 281KG, yield 96.5%.
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| CN1088930A (en) * | 1993-10-12 | 1994-07-06 | 泰安市精细化工总厂 | Stable organotin compound and its production and application |
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| CN1435416A (en) * | 2002-01-28 | 2003-08-13 | 朱雅文 | Dimercaptoacetic acid isooctyl ester dimethoxy-carbonyl ethyl tin compound and preparation method thereof |
| CN102796282A (en) * | 2012-08-21 | 2012-11-28 | 衢州建华东旭助剂有限公司 | Aliphatic acid mercaptoethanol ester methyl tin heat stabilizer and preparation method thereof |
| CN104629208A (en) * | 2013-11-14 | 2015-05-20 | 湖北南星化工总厂 | Composite solid methyltin PVC (polyvinyl chloride) heat stabilizer and preparation method thereof |
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2016
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1088930A (en) * | 1993-10-12 | 1994-07-06 | 泰安市精细化工总厂 | Stable organotin compound and its production and application |
| CN1137048A (en) * | 1995-05-27 | 1996-12-04 | 深圳泛胜塑胶助剂有限公司 | PVC resin preparing process using mixture of methyl tin and thiolate as thermal stabilizer |
| CN1435416A (en) * | 2002-01-28 | 2003-08-13 | 朱雅文 | Dimercaptoacetic acid isooctyl ester dimethoxy-carbonyl ethyl tin compound and preparation method thereof |
| CN102796282A (en) * | 2012-08-21 | 2012-11-28 | 衢州建华东旭助剂有限公司 | Aliphatic acid mercaptoethanol ester methyl tin heat stabilizer and preparation method thereof |
| CN104629208A (en) * | 2013-11-14 | 2015-05-20 | 湖北南星化工总厂 | Composite solid methyltin PVC (polyvinyl chloride) heat stabilizer and preparation method thereof |
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