CN103408531A - Method for synthesizing sulfurized isobutylene - Google Patents
Method for synthesizing sulfurized isobutylene Download PDFInfo
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- CN103408531A CN103408531A CN2013103876003A CN201310387600A CN103408531A CN 103408531 A CN103408531 A CN 103408531A CN 2013103876003 A CN2013103876003 A CN 2013103876003A CN 201310387600 A CN201310387600 A CN 201310387600A CN 103408531 A CN103408531 A CN 103408531A
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- reaction
- temperature
- butylene
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- pressure
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 238000000034 method Methods 0.000 title abstract description 8
- 230000002194 synthesizing effect Effects 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 46
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000007259 addition reaction Methods 0.000 claims abstract description 12
- 230000003647 oxidation Effects 0.000 claims abstract description 3
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 3
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims abstract description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 19
- 238000010189 synthetic method Methods 0.000 claims description 11
- 241000972773 Aulopiformes Species 0.000 claims description 8
- 230000037452 priming Effects 0.000 claims description 8
- 235000019515 salmon Nutrition 0.000 claims description 8
- 238000013021 overheating Methods 0.000 claims description 7
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 238000001308 synthesis method Methods 0.000 abstract description 5
- 239000005864 Sulphur Substances 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 3
- 239000012535 impurity Substances 0.000 abstract description 2
- 230000003213 activating effect Effects 0.000 abstract 1
- 238000007599 discharging Methods 0.000 abstract 1
- 230000009965 odorless effect Effects 0.000 abstract 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 14
- 239000011734 sodium Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 235000010265 sodium sulphite Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000001307 helium Substances 0.000 description 5
- 229910052734 helium Inorganic materials 0.000 description 5
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 230000009967 tasteless effect Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000004763 sulfides Chemical class 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- -1 sulphur alkene Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for synthesizing sulfurized isobutylene, for solving the problems of products prepared by the existing T321 high-pressure synthesis method, such as strong sharp aroma, high impurity content and high production cost. The method disclosed by the invention comprises the following steps of: adding elemental sulphur and sodium sulphide solution into a reaction kettle without oxidation treatment in the normal temperature state, gradually increasing the temperature, and carrying out activating reaction at temperature from normal temperature to 100 DEG C till the solution is of an orange red color and is transparent; and introducing isobutene into the reaction kettle, continuously increasing the temperature, controlling reaction temperature to be 100-204 DEG C, controlling pressure to be 1.0-6.9 MPa, and discharging sulfurized isobutylene after carrying out addition reaction for 1-16h, wherein the molar ratio of elemental sulphur to isobutene is 1.0:(0.5-3.5). The method for synthesizing sulfurized isobutylene disclosed by the invention has the advantages of high yield and product quality, low production cost, clean and odorless reaction process and the like.
Description
Technical field
The invention belongs to the synthetic method of sulphur alkene, is a kind of synthetic method of sulfide isobutene specifically, is more specifically the tasteless high pressure synthesis method of a kind of highly purified T321.
Background technology
The sulfide isobutene extreme pressure anti-wear additives, product designation T321, this product has high sulfur content, and good oil soluble is arranged in mineral oil, good extreme pressure activity and thermostability.Due to the advantageous characteristic of T321, thereby be widely used in and be deployed into gear oil, metal working oil, lubricating grease and the antiwear hydraulic oil that meets different size by domestic and international manufacturer.But due to its reaction process, produce waste liquid, the waste gas of a large amount of stenches, environmental pollution is serious, once once stops production abroad.
In prior art, mainly comprise normal pressure and high pressure synthesis method production sulfide isobutene, but which kind of production method all can't be dispelled the pungent bad smell produced in reaction process.Wherein, the high pressure synthesis method has advantages of that reaction process is short, although people, through a large amount of trial, continue to optimize techniques such as synthetic, the tasteless processing of T321, removal of impurities, but its pungent bad smell still just can't be eliminated, tracing it to its cause is that the side reaction of iso-butylene and elemental sulfur has generated mercaptan.Therefore, the low flavor of exploration, tasteless sulfide isobutene synthesis technique have become a focus in the synthetic field of sulfur-bearing organic derivative.
Summary of the invention
The synthetic method that the purpose of this invention is to provide a kind of sulfide isobutene.The problems such as in existing T321 high pressure synthesis method, the product sharp aroma is large, foreign matter content is high, production cost is high have been solved.
The object of the present invention is achieved like this: the synthetic method of this sulfide isobutene comprises the following steps: under the normal temperature state, elemental sulfur and sodium sulfide solution are added in the reactor of non-oxidation processing, heat up gradually, make its priming reaction in normal temperature to 100 ℃, make solution be the transparent salmon state; Then, pass into iso-butylene in reactor, persistently overheating and temperature of reaction is controlled to 100 ~ 204 ℃, pressure-controlling, at 1.0 ~ 6.9MPa, after addition reaction 1 ~ 16h is discharged sulfide isobutene; The mol ratio of elemental sulfur and iso-butylene is 1.0:0.5 ~ 3.5.
For improving reaction efficiency and yield, described addition reaction temperature is 110 ~ 160 ℃.
For improving reaction efficiency and yield, described addition reaction pressure is 2.0 ~ 4.5Mpa.
For improving reaction efficiency and yield, the mol ratio of described elemental sulfur and iso-butylene is 1:1.0 ~ 2.5, is preferably 1:1.5 ~ 2.0.
Advantage of the present invention and beneficial effect are: owing to using sodium sulphite as catalyzer, not only make reaction under equal condition of high voltage be more conducive to carry out, shorten reaction process, reaction process is easy to control, constant product quality.Na after reaction
2S is dissolved in water, while extracting the target product T321 of oil phase, minute quantity Na is only arranged
2S sneaks into.And due to the change of reaction process, make in target product not chloridely, improved quality product.Simultaneously, avoided elemental sulfur directly with isobutene reaction, to generate the mercaptan with pungent bad smell, reaction process cleans tasteless, environmental protection more.Na
2The S reusable edible, greatly reduce production cost.The priming reaction temperature of catalyzer lower (prior art is 150 ~ 250 ℃, and this patent is less than 100 ℃), reduced reaction temperature required, saved production cost.After adopting catalyzer of the present invention and synthesis condition, synthesized have surmount common sulfide isobutene application performance tasteless, without chlorine, low viscous extreme pressure antiwear agent for lubricant oil, its anti-extreme pressure is higher than 15 ~ 25% of non-pressure process.
Reaction mechanism of the present invention is as follows:
（1）?
；
（2）
。
In above-mentioned reaction equation, R is iso-butylene.As can be known by above-mentioned reaction mechanism, wherein, Na
2Sn is transparent salmon liquid, passes through Na
2S reacts with elemental sulfur and generates Na
2Sn, by elemental sulfur, catalyst activation, is about to Na
2Sn, as the carrier of reactant elemental sulfur, therefore is more conducive to reaction and carries out.Na
2Sn reacts under High Temperature High Pressure with iso-butylene and generates Na
2S and target product T321, shortened reaction process.Na
2The total amount of S before and after reaction is constant, namely as catalyzer.The Na that therefore, denier is only arranged
2S sneaks into T321, and quality product is better, and has saved catalyst levels, has reduced production cost.
Embodiment
Embodiment 1
Below elaborate content of the present invention.The synthetic method of this sulfide isobutene comprises the following steps: under the normal temperature state, 32kg elemental sulfur powder and the aqueous solution that contains 31kg sodium sulphite are added in the emptying reactor of rare gas element (as nitrogen, helium), heat up gradually, make its priming reaction in 25 ~ 100 ℃, make solution be the transparent salmon state, namely sodium sulphite and elemental sulfur complete reaction have generated sodium polysulphide.Then, in reactor, slowly pass into iso-butylene by high-pressure metering pump, control the flow velocity of iso-butylene, persistently overheating and temperature of reaction is controlled to 115 ~ 204 ℃, pressure-controlling, at 1.0 ~ 6.9MPa, is cooled to room temperature after reaction, after addition reaction 8 ~ 10h, sulfide isobutene is discharged.
Embodiment 2
Under the normal temperature state, 32kg elemental sulfur powder and the aqueous solution that contains 28kg sodium sulphite are added in the emptying reactor of rare gas element (as nitrogen, helium), heat up gradually, make its priming reaction in 45 ~ 90 ℃, make solution be the transparent salmon state.Then, in reactor, slowly pass into the 196kg iso-butylene by high-pressure metering pump, control the flow velocity of iso-butylene, persistently overheating and temperature of reaction is controlled to 125 ~ 195 ℃, pressure-controlling, at 2.2 ~ 5.5MPa, is cooled to room temperature after reaction, after addition reaction 10 ~ 12h, sulfide isobutene is discharged.
Embodiment 3
Under the normal temperature state, 32kg elemental sulfur powder and the aqueous solution that contains 32kg sodium sulphite are added in the emptying reactor of rare gas element (as nitrogen, helium), heat up gradually, make its priming reaction in 75 ~ 87 ℃, make solution be the transparent salmon state.Then, in reactor, slowly pass into the 84kg iso-butylene by high-pressure metering pump, control the flow velocity of iso-butylene, persistently overheating and temperature of reaction is controlled to 130 ~ 180 ℃, pressure-controlling, at 2.5 ~ 4.5MPa, is cooled to room temperature after reaction, after addition reaction 1 ~ 3h, sulfide isobutene is discharged.
Embodiment 4
Under the normal temperature state, 32kg elemental sulfur powder and the aqueous solution that contains 30kg sodium sulphite are added in the emptying reactor of rare gas element (as nitrogen, helium), heat up gradually, make its priming reaction in 80 ~ 85 ℃, make solution be the transparent salmon state.Then, in reactor, slowly pass into the 140kg iso-butylene by high-pressure metering pump, control the flow velocity of iso-butylene, persistently overheating and temperature of reaction is controlled to 145 ~ 170 ℃, pressure-controlling, at 3.0 ~ 3.5MPa, is cooled to room temperature after reaction, after addition reaction 4 ~ 6h, sulfide isobutene is discharged.
Embodiment 5
Under the normal temperature state, 32kg elemental sulfur powder and the aqueous solution that contains 30kg sodium sulphite are added in the emptying reactor of rare gas element (as nitrogen, helium), heat up gradually, make its priming reaction in 85 ~ 95 ℃, make solution be the transparent salmon state.Then, in reactor, slowly pass into the 112kg iso-butylene by high-pressure metering pump, control the flow velocity of iso-butylene, persistently overheating and temperature of reaction is controlled to 135 ~ 160 ℃, pressure-controlling, at 4.2 ~ 5.5MPa, is cooled to room temperature after reaction, after addition reaction 8 ~ 12h, sulfide isobutene is discharged.
The yield of the T321 crude product of embodiment 1 ~ 5 gained is 120 ~ 190% of iso-butylene.Then crude product is carried out to the rectifying postscript and obtain highly purified T321, its yield is 120% ~ 150% of iso-butylene.
Each component proportion of the T321 of embodiment 1 ~ 5 gained: monosulphide<0.5 wt%; Disulphide 20 ~ 35 wt%; Trisulphide 30 ~ 50 wt%; Tetrasulfide 15 ~ 18wt%.
The significant parameter of the T321 of embodiment 1 ~ 5 gained is as follows: sharp aroma: nothing; Flash-point>95 ℃; Kinematic viscosity (100 ℃): 1.0 ~ 1.8 mm
2/ s; Sulphur content 40 ~ 44 wt%; Copper rotten (121 ℃, 3h): three grades; Flash-point>95 ℃; Chlorine: do not contain.
The T321 of embodiment 1 ~ 5 gained is at the four-ball test application performance, all high by 4 ~ 12% than non-pressure process.
Claims (5)
1. the synthetic method of a sulfide isobutene, comprise the following steps: under the normal temperature state, elemental sulfur and sodium sulfide solution are added in the reactor of non-oxidation processing, heat up gradually, make its priming reaction in normal temperature to 100 ℃, make solution be the transparent salmon state; In reactor, pass into iso-butylene, persistently overheating and temperature of reaction is controlled to 100 ~ 204 ℃, pressure-controlling, at 1.0 ~ 6.9MPa, after addition reaction 1 ~ 16h is discharged sulfide isobutene; The mol ratio of elemental sulfur and iso-butylene is 1.0:0.5 ~ 3.5.
2. the synthetic method of sulfide isobutene according to claim 1, it is characterized in that: described addition reaction temperature is 110 ~ 160 ℃.
3. the synthetic method of sulfide isobutene according to claim 1, it is characterized in that: described addition reaction pressure is 2.0 ~ 4.5Mpa.
4. the synthetic method of sulfide isobutene according to claim 1, it is characterized in that: the mol ratio of described elemental sulfur and iso-butylene is 1:1.0 ~ 2.5.
5. the synthetic method of sulfide isobutene according to claim 4, it is characterized in that: the mol ratio of described elemental sulfur and iso-butylene is 1:1.5 ~ 2.0.
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| CN2013103876003A CN103408531A (en) | 2013-08-31 | 2013-08-31 | Method for synthesizing sulfurized isobutylene |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103613578A (en) * | 2013-11-07 | 2014-03-05 | 安徽大学 | Method for green and efficient preparation of lubricating oil additive T321 by medium-pressure solvothermal method |
| CN105541791A (en) * | 2016-01-28 | 2016-05-04 | 沈阳广达化工有限公司 | System for increasing yield in synthesis of sulfurized isobutylene |
| CN111944582A (en) * | 2020-09-08 | 2020-11-17 | 定远县云森科技有限公司 | A kind of low odor and high activity extreme pressure antiwear agent and preparation method thereof |
| CN111979028A (en) * | 2020-09-08 | 2020-11-24 | 定远县云森科技有限公司 | A kind of low odor and low corrosive extreme pressure antiwear agent and preparation method thereof |
| CN112552983A (en) * | 2019-09-26 | 2021-03-26 | 中国石油化工股份有限公司 | Ashless vehicle gear oil and preparation method thereof |
| CN114835676A (en) * | 2022-06-17 | 2022-08-02 | 黄河三角洲京博化工研究院有限公司 | Synthetic method of high-sulfur-content sulfurized isobutylene |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101096353A (en) * | 2006-06-30 | 2008-01-02 | 山东联合化工股份有限公司 | Synthesis technique of sulfide isobutene by one-step method |
-
2013
- 2013-08-31 CN CN2013103876003A patent/CN103408531A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101096353A (en) * | 2006-06-30 | 2008-01-02 | 山东联合化工股份有限公司 | Synthesis technique of sulfide isobutene by one-step method |
Non-Patent Citations (1)
| Title |
|---|
| 王德秋等: "有机预硫化剂的合成", 《化学工业与工程》, vol. 25, no. 4, 31 July 2008 (2008-07-31), pages 302 - 305 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103613578A (en) * | 2013-11-07 | 2014-03-05 | 安徽大学 | Method for green and efficient preparation of lubricating oil additive T321 by medium-pressure solvothermal method |
| CN105541791A (en) * | 2016-01-28 | 2016-05-04 | 沈阳广达化工有限公司 | System for increasing yield in synthesis of sulfurized isobutylene |
| CN105541791B (en) * | 2016-01-28 | 2017-11-03 | 沈阳广达化工有限公司 | The system that yield is improved in sulfide isobutene synthesis |
| CN112552983A (en) * | 2019-09-26 | 2021-03-26 | 中国石油化工股份有限公司 | Ashless vehicle gear oil and preparation method thereof |
| CN111944582A (en) * | 2020-09-08 | 2020-11-17 | 定远县云森科技有限公司 | A kind of low odor and high activity extreme pressure antiwear agent and preparation method thereof |
| CN111979028A (en) * | 2020-09-08 | 2020-11-24 | 定远县云森科技有限公司 | A kind of low odor and low corrosive extreme pressure antiwear agent and preparation method thereof |
| CN114835676A (en) * | 2022-06-17 | 2022-08-02 | 黄河三角洲京博化工研究院有限公司 | Synthetic method of high-sulfur-content sulfurized isobutylene |
| CN114835676B (en) * | 2022-06-17 | 2024-03-19 | 黄河三角洲京博化工研究院有限公司 | Synthetic method of high-sulfur-content vulcanized isobutene |
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Application publication date: 20131127 |