CN112745183A - C with low isobutene content4Method for synthesizing isooctene by oligomerization - Google Patents
C with low isobutene content4Method for synthesizing isooctene by oligomerization Download PDFInfo
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- CN112745183A CN112745183A CN201911049286.1A CN201911049286A CN112745183A CN 112745183 A CN112745183 A CN 112745183A CN 201911049286 A CN201911049286 A CN 201911049286A CN 112745183 A CN112745183 A CN 112745183A
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000006384 oligomerization reaction Methods 0.000 title claims abstract description 16
- DFVOXRAAHOJJBN-UHFFFAOYSA-N 6-methylhept-1-ene Chemical compound CC(C)CCCC=C DFVOXRAAHOJJBN-UHFFFAOYSA-N 0.000 title claims description 14
- 230000002194 synthesizing effect Effects 0.000 title claims description 4
- 239000011347 resin Substances 0.000 claims abstract description 69
- 229920005989 resin Polymers 0.000 claims abstract description 69
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 36
- 230000008569 process Effects 0.000 claims abstract description 25
- 239000003112 inhibitor Substances 0.000 claims abstract description 21
- 238000005658 halogenation reaction Methods 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 17
- 230000026030 halogenation Effects 0.000 claims abstract description 13
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 35
- 239000000047 product Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000010030 laminating Methods 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- -1 bromine halide Chemical class 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 7
- 229910052799 carbon Inorganic materials 0.000 abstract description 7
- 150000003460 sulfonic acids Chemical class 0.000 abstract description 3
- 239000002245 particle Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000005829 trimerization reaction Methods 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 230000031709 bromination Effects 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000006471 dimerization reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 238000003475 lamination Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 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 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/28—Catalytic processes with hydrides or organic compounds with ion-exchange resins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- C07C2531/08—Ion-exchange resins
- C07C2531/10—Ion-exchange resins sulfonated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention discloses a process method for superposing four low-isobutene carbon raw materials. Mixing the carbon four raw materials, sequentially passing through two superposed reaction sections connected in series under the condition of not adding an inhibitor, and carrying out superposed reaction under the condition of a superposed process; the conventional sulfonic acid resin is used in the first polymerization reaction section, and the brominated sulfonic acid resin is used in the second polymerization reaction section, wherein the halogenation rate is 20-40%. When the mass content of isobutene in C4 oligomerization raw material is lower than normal level, the method still maintains higher isobutene conversion rate and selectivity under the condition of eliminating the addition of inhibitor, and increases the economical efficiency of the device.
Description
Technical Field
The invention relates to a C with low isobutene content4(isobutene mass percent: 8% -15%) oligomerization synthesis method of isooctene.
Background
MTBE is a gasoline blending component with excellent performance, but has carcinogenicity. The united states has long banned its addition to gasoline. At present, China is also popularizing ethanol gasoline and will forbid the artificial addition of MTBE in the gasoline. One hundred more MTBE devices in China are facing to improvement, wherein the widely seen alternative technology is the technology for producing isooctenes by C4 oligomerization. However, in the oligomerization of C4, polymers are formed, so that it is common practice to add inhibitors during the oligomerization process, thereby reducing the production of by-products.
There are many MTBE devices in the country, with a capacity of about 1800 million tons in 2018. If one-fourth of the plants selected C4 oligomerization as an alternative technique, the approximate calculated addition of inhibitor was about 5 ten thousand tons per year. The inhibitor is used as a non-popular chemical in chemical products, and the market productivity of the inhibitor reaches a certain balance. If the demand is increased greatly in a short time, the price of the inhibitor is increased greatly, and the economic benefit of the C4 oligomerization device is further reduced sharply. Therefore, it is a very critical and practical task to study how to reach the selectivity and conversion rate of isooctene produced by C4 oligomerization without adding an inhibitor.
In addition, in the actual production, the concentration of olefin in the C4 raw material is easy to change due to the fluctuation of equipment and the change of raw material sources, when the content of isobutene in the C4 raw material (8 wt% -15 wt%) is lower than the normal value, a higher initial reaction temperature (40-50 ℃) is needed, the temperature rise is 20-42 ℃, and by adopting the conventional resin and filling mode, an inhibitor must be added, otherwise, the use temperature range of the conventional resin is exceeded, and the increase of byproducts is caused.
Disclosure of Invention
The invention provides a method, which can achieve the same isobutene conversion rate and selectivity as the reaction with an inhibitor under the condition of not adding the inhibitor when the isobutene mass content in the raw material is 8-15%. So that the C4 oligomerization can be carried out without inhibitor and an acceptable product is produced. The economy of the device is not influenced by the inhibitor and the price thereof, so that the device can run stably for a long time.
C with low isobutene content4The process method for synthesizing isooctene by oligomerization comprises the following steps:
mixing the C-C raw material, sequentially passing through two superposed reaction sections connected in series under the condition of not adding an inhibitor, carrying out superposed reaction under the condition of a superposed process, and separating a reaction product to obtain an isooctene product;
a resin catalyst A is used in the first polymerization reaction section, the resin catalyst A is sulfonic acid resin, the acid exchange equivalent weight of the resin catalyst A is 2.0-6.0 mg/g, preferably 5.0-6.0 mg/g, and the halogenation rate is 0;
in the second polymerization reaction section, resin catalyst B is used, the resin catalyst B is halogenated sulfonic acid resin, the acid exchange equivalent thereof is equivalent to that of the resin catalyst A, preferably 4.0-6.0 mg/g, and the halogenation rate is 20-40%.
Further, the resin A is conventional sulfonic acid resin; the resin B is brominated sulfonic acid resin, the acid exchange equivalent of the resin B is equivalent to that of the resin A, and the halogenation rate is 20-40%. The halogenation rate refers to the molar ratio of halogen element (bromine) to sulfonate in the resin catalyst.
Furthermore, the filling amount of the resin catalyst A in the first lamination reaction section is 5-20%, preferably 10-15% based on the total filling volume of all the resin catalysts. The filling amount of the resin catalyst B in the second polymerization reaction section is 80-95%, preferably 85-90%.
Further, the lamination process conditions include: the average reaction temperature of the first polymerization reaction section is 42-57 ℃, and the liquid hourly volume space velocity is 4h-1~22h-1Preferably 6h-1~15h-1(ii) a The average reaction temperature of the second polymerization reaction section is 53-71 ℃, and the liquid hourly volume space velocity is 0.5h-1~4h-1Preferably 1h-1~2h-1。
In the invention, the first polymerization reaction section and the second polymerization reaction section can be arranged in one reactor or more than two reactors. Each reaction zone may comprise one or more catalyst beds.
In the invention, the C-containing raw material is a C4 raw material with low isobutene content, wherein the mass content of isobutene is generally 8-15 wt%.
Compared with the prior art, the process method has the beneficial effects that:
1. according to the process characteristics of the C4 polymerization reaction, the catalyst is selected to be compounded and filled, so that the generation of polymers (such as trimerization products and tetramerization products) is reduced. The carbon tetramerization reaction is characterized in that the exothermic quantity is large, most of the exothermic quantity is concentrated in the first half part of the reaction, and a large amount of carbon octaolefin can be generated in the first half part of the reaction. It is therefore desirable to have the oligomerization (dimerization) of isobutene take place as quickly as possible and to control the reaction depth as far as possible. The use of conventional resins in the first polymerization stage, at relatively high space velocities, allows the oligomerization (dimerization) of the tetraisobutene carbonate to occur as quickly as possible. The concentration of carbon octaolefins increases rapidly as the reactants flow progressively downstream. The brominated sulfonic acid resin is filled in the second laminating section, and the generation of trimerization (including trimerization and tetramerization) products can be inhibited by utilizing the steric hindrance effect of halogen groups on the brominated resin.
2. The addition of the inhibitor is cancelled in the whole process of the polymerization reaction, so that higher selectivity and conversion rate can be realized, and the requirement of industrial production is met. The use of brominated sulfonic acid resin in the second lamination stage is intended to reduce the formation of polymeric products without the addition of inhibitors. The principle is as follows: after halogenation of conventional sulfonic acid resins, bromine is introduced around the acidic groups. The bromine group has stronger polarity, electronegativity and larger volume, thereby generating steric hindrance effect on the resin structure; the steric hindrance effect formed by the bromine group effectively reduces the opportunity that the dimerization and trimerization products approach the acid center of the resin catalyst, and meanwhile, the bromine group has different sizes of the electronegative effect on the carbon four and carbon eight olefins, so that the dimerization and trimerization products are not easy to activate, the generation amount of the trimerization and tetramerization products is also reduced, and the selectivity of the polymerization reaction process is improved.
3. When the mass content (8-15%) of isobutene in the C4 oligomerization raw material is lower than a normal level, the addition of an inhibitor is cancelled on the premise of achieving higher isobutene conversion rate and selectivity, and the economy of the device is not influenced by the inhibitor and the price thereof, so that the device can stably run for a long time. The method provides an effective way for the transformation of the existing MTBE device.
Detailed Description
The process of the present invention is further described below by means of specific examples.
The acidic cation exchange resin used in the present invention is prepared by a conventional method. The halogenated resin is prepared through halogenation reaction on cation exchange resin as catalyst carrier and conventional process. The resin catalyst A is conventional sulfonic acid resin, and the resin B is brominated sulfonic acid resin. Detailed indexes of the resin catalyst are shown in Table 1, and the analysis standard of the catalyst is GB-T16579-1996.
TABLE 1 physicochemical Properties of the catalyst
In the following comparative examples and examples, the same raw materials were used as the C4 blend raw materials, and the compositions are shown in Table 2. The mixed C4 material and the hydrogenated product were analyzed by gas chromatography.
TABLE 2C 4 blend stock
Comparative example 1
The resin catalysts used in comparative example 1 were all resin A (particle size 1.1mm, exchange equivalent 5.4 mg/g, water content 50 wt%, wet apparent density 0.8 g/mL)-1) The grading filling was not carried out, the inhibitor used was tert-butanol, the amount added was 1.0% by mass of the feed amount. At the average reaction temperature of 55 ℃ and the total volume space velocity of 1h-1Under the conditions of (1), the conversion of isobutylene was 86.1% and the selectivity to isooctene was 87.3%.
Example 1
Catalyst grading filling mode: the first polymerization stage was charged with resin A (particle size 1.1mm, exchange equivalent 5.4 mg/g, water content 50 wt%, wet apparent density 0.8 g.mL)-1Halogenation rate is 0), the packing volume proportion of the resin A is 5%; filling resin B (in the second polymerization reaction section)Particle size of 1.1mm, exchange equivalent of 5.2 mg/g, water content of 50 wt%, wet apparent density of 0.8 g/mL-1The halogenation (bromination) rate was 40%), and the packed volume ratio of the resin B was 95%.
The average reaction temperature of the first polymerization reaction section is 43 ℃, and the volume space velocity is 20 h-1The average reaction temperature of the second polymerization reaction section is 57 ℃, and the space velocity is 1h-1The isobutene conversion was 82.3% and the isooctene selectivity was 84.1%.
Example 2
Catalyst grading filling mode: the first polymerization stage was charged with resin A (particle size 1.1mm, exchange equivalent 5.2 mg/g, water content 50 wt%, wet apparent density 0.8 g.mL)-1Halogenation rate is 0), the packing volume proportion of the resin A is 12%; the second polymerization stage was charged with resin B (particle size 1.1mm, exchange equivalent 5.2 mg/g, water content 50 wt%, wet apparent density 0.8 g.mL)-1The halogenation (bromination) rate was 40%), and the packed volume ratio of the resin B was 88%.
The average reaction temperature of the first polymerization reaction section is 46 ℃, and the volume space velocity is 9 h-1The average reaction temperature of the second polymerization reaction section is 60 ℃, and the space velocity is 1.2 h-1The isobutene conversion was 87.5% and the isooctene selectivity was 86.3%.
Example 3
Catalyst grading filling mode: the first polymerization stage was charged with resin A (particle size 1.1mm, exchange equivalent 5.2 mg/g, water content 50 wt%, wet apparent density 0.8 g.mL)-1Halogenation rate is 0), the packing volume proportion of the resin A is 15%; the second polymerization stage was charged with resin B (particle size 1.1mm, exchange equivalent 5.2 mg/g, water content 50 wt%, wet apparent density 0.8 g.mL)-1The halogenation (bromination) rate was 45%), and the packed volume ratio of the resin B was 85%.
The average reaction temperature of the first polymerization reaction section is 47 ℃, and the volume space velocity is 7 h-1The average reaction temperature of the second polymerization reaction section is 61 ℃, and the space velocity is 1.2 h-1The isobutene conversion was 89.8% and the isooctene selectivity was 87.1%.
Example 4
Catalyst grading filling mode: in thatThe first polymerization stage was packed with resin A (particle size 1.1mm, exchange equivalent 5.0 mg/g, water content 50 wt%, wet apparent density 0.8 g. mL)-1Halogenation rate is 0), the packing volume proportion of the resin A is 20%; the second polymerization stage was charged with resin B (particle size 1.1mm, exchange equivalent 5.0 mg/g, water content 50 wt%, wet apparent density 0.8 g.mL)-1The halogenation (bromination) rate was 40%), and the packed volume ratio of the resin B was 80%.
The average reaction temperature of the first polymerization reaction section is 48 ℃, and the volume space velocity is 6h-1The average reaction temperature of the second polymerization reaction section is 62 ℃ and the space velocity is 1.3 h-1The isobutene conversion was 89.8% and the isooctene selectivity was 85.0%.
The same raw materials are used, and the comparative example 1 and the examples 1 to 4 have the same reaction results, so that the method provided by the invention can eliminate the addition of the inhibitor on the premise of keeping equivalent or slightly improved conversion rate and selectivity of isobutene, and greatly improve the economy of the device.
Claims (10)
1. A process method for synthesizing isooctene by oligomerization of C4 raw materials comprises the following steps:
mixing the C-C raw material, sequentially passing through two superposed reaction sections connected in series under the condition of not adding an inhibitor, carrying out superposed reaction under the condition of a superposed process, and separating a reaction product to obtain an isooctene product;
a resin catalyst A is used in the first polymerization reaction section, the resin catalyst A is sulfonic acid resin, the acid exchange equivalent is 2.0-6.0 mg/g, and the halogenation rate is 0;
and a resin catalyst B is used in the second polymerization reaction section, wherein the resin catalyst B is brominated sulfonic acid resin, the acid exchange equivalent of the resin catalyst B is equivalent to that of the resin catalyst B, and the halogenation rate is 20-40%.
2. The process according to claim 1, wherein the resin A has an acid exchange equivalent of 5.0 to 6.0 mg/g; the resin B has an acid exchange equivalent of 4.0 to 6.0 mg/g.
3. The process of claim 1 wherein said halogenation rate is the molar ratio of bromine halide to sulfonate in the resin catalyst.
4. The process method of claim 1, wherein the loading amount of the resin catalyst A in the first polymerization reaction section is 5-20% and the loading amount of the resin catalyst B in the second polymerization reaction section is 80-95% based on the total loading volume of all the resin catalysts.
5. The process of claim 1, wherein the loading of the resin catalyst A in the first polymerization reaction stage is 10% to 15%.
6. The process of claim 1, wherein the loading of resin catalyst B in the second polymerization reaction zone is 85% to 90%.
7. The process of claim 1 wherein said laminating process conditions comprise: the average reaction temperature of the first polymerization reaction section is 42-57 ℃, and the liquid hourly volume space velocity is 4h-1~22h-1(ii) a The average reaction temperature of the second polymerization reaction section is 53-71 ℃, and the liquid hourly volume space velocity is 0.5h-1~4h-1。
8. The process of claim 7 wherein said laminating process conditions comprise: the liquid hourly space velocity of the first polymerization reaction section is 6h-1~15h-1(ii) a The liquid hourly space velocity of the second polymerization reaction section is 1h-1~2h-1。
9. The process of claim 1 wherein the first and second superimposed reaction zones are disposed in one reactor or in more than two reactors.
10. The process method according to claim 1, wherein the mass content of isobutene in the mixed C-C raw material is 8-15 wt%.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB733753A (en) * | 1952-09-25 | 1955-07-20 | Bataafsche Petroleum | Process for carrying out hydrocarbon reactions accelerated by catalysts of an acid nature |
| CN101190860A (en) * | 2006-11-30 | 2008-06-04 | 中国石油化工股份有限公司 | Dimerization-etherification method for producing MTBE, isooctene and diisobutylene from C4 olefin |
| CN107973680A (en) * | 2017-11-23 | 2018-05-01 | 丹东明珠特种树脂有限公司 | Isobutene polymerization catalyst filling structure |
-
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- 2019-10-31 CN CN201911049286.1A patent/CN112745183B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB733753A (en) * | 1952-09-25 | 1955-07-20 | Bataafsche Petroleum | Process for carrying out hydrocarbon reactions accelerated by catalysts of an acid nature |
| CN101190860A (en) * | 2006-11-30 | 2008-06-04 | 中国石油化工股份有限公司 | Dimerization-etherification method for producing MTBE, isooctene and diisobutylene from C4 olefin |
| CN107973680A (en) * | 2017-11-23 | 2018-05-01 | 丹东明珠特种树脂有限公司 | Isobutene polymerization catalyst filling structure |
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