CN100586942C - Production method of dioxane - Google Patents
Production method of dioxane Download PDFInfo
- Publication number
- CN100586942C CN100586942C CN200810013740A CN200810013740A CN100586942C CN 100586942 C CN100586942 C CN 100586942C CN 200810013740 A CN200810013740 A CN 200810013740A CN 200810013740 A CN200810013740 A CN 200810013740A CN 100586942 C CN100586942 C CN 100586942C
- Authority
- CN
- China
- Prior art keywords
- diox
- dioxane
- butylene
- formaldehyde
- iso
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 title abstract 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 85
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 239000003377 acid catalyst Substances 0.000 claims abstract description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 13
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 8
- 239000012752 auxiliary agent Substances 0.000 claims description 7
- 239000008098 formaldehyde solution Substances 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- 235000010288 sodium nitrite Nutrition 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 31
- 238000009835 boiling Methods 0.000 abstract description 26
- 239000000047 product Substances 0.000 abstract description 6
- 238000007171 acid catalysis Methods 0.000 abstract description 5
- 238000010478 Prins reaction Methods 0.000 abstract description 4
- 239000000284 extract Substances 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- GDKSTFXHMBGCPG-UHFFFAOYSA-N 4,4-dimethyl-1,3-dioxane Chemical compound CC1(C)CCOCO1 GDKSTFXHMBGCPG-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 35
- 239000000463 material Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 238000007086 side reaction Methods 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- UUIRDIWGVMSEBE-UHFFFAOYSA-N acetylene propan-2-one Chemical compound C#C.CC(C)=O UUIRDIWGVMSEBE-UHFFFAOYSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- -1 o-NP Chemical compound 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for manufacturing 4, 4-dimethyl-1, 3-dioxane, which belongs to the technical field of chemical product manufacturing method. A preparation method for dioxane is characterized in that formaldehyde, isobutene, an acid catalyst and additives are put in a sealed container to react and then the reaction product is extracted by fatty hydrocarbon, the extract is distilled to acquire dioxane, the content of a by-product high-boiling product in the reaction product is low, and the purity and yield of the dioxane is high. Aiming at the difficult problem that the formaldehyde and the isobutene have a large amount production of high-boiling products during prins reaction process under an acid catalysis, the preparation method of the dioxane of the invention can effectively reduce the production amount of high-boiling products and improve the purity and yield of the dioxane; the content of high-boiling objects in the dioxane product acquired from the method of theinvention is obviously declined, and the yield of the dioxane can be up to 89 to 95 percent.
Description
Technical field
The invention relates to the method for making of making isoprene process intermediate by iso-butylene, a kind of manufacturing 4 of saying so more specifically, 4-dimethyl-1, the method for 3-diox belongs to Chemicals manufacture method technical field.
Background technology
Isoprene is the important source material of producing polyisoprene rubber, and the production method of isoprene comprises cracking c5 cut extractive distillation method, dehydriding, chemical synthesis etc. at present.Wherein chemical synthesis comprises iso-butylene-formaldehyde method, acetylene-acetone method, propylene dimerization etc.Utilize the method at present industrialization of prins reaction by formaldehyde and the synthetic isoprene of iso-butylene, the chemical reaction of generation is as follows:
This reaction process realizes by the liquid phase two-step mode technique that normally the condensation under acid catalysis of the first step iso-butylene and formaldehyde generates diox, and the 2nd step diox cracking under catalyst action generates isoprene, formaldehyde and water.About this process, document DAS NO.1271106, DAS NO.1233880 and BelgianPat.NO.735564 all have introduction.
Patent GB825034A discloses and has a kind ofly made the method for diox by iso-butylene and formaldehyde under acid catalysis, and wherein the mol ratio of formaldehyde and iso-butylene is between 2～10; Temperature of reaction is controlled at: 55～75 ℃; The mass ratio of water and formaldehyde is controlled between 2～4; When being catalyzer with sulfuric acid, sulfuric acid pure heavy account for water aldehyde system heavy 5%～35%; When with phosphoric acid during as catalyzer, phosphoric acid account for water aldehyde system heavy 15%～75%.Patent fails to report the yield of diox, we verify the embodiment 1 of this patent, and the yield of finding this example Zhong diox is only 22%, and have generated a large amount of high boiling material in the reaction process, these high boiling material are very difficult to separate Yu diox, cause the purity of diox not high.The purity of gained diox is 98.4% in this patent working example 1, but our repeated experiments finds that this method gained De diox purity only is 86%.
Patent US2962507A1 discloses the method that a kind of utilization contains C4 component gas condensation reaction generation diox under acid catalyst as raw material and formaldehyde of iso-butylene, as the iso-butylene raw material, wherein the mol ratio of formaldehyde and iso-butylene is greater than 2 with the C4 that contains iso-butylene for this method; Temperature of reaction is controlled between 10～85 ℃; The mass ratio of water and formaldehyde is controlled between 1～10; Used acid accounts for 5～75% of water and aldehyde quality; The pressure of reaction is 0.02～15 normal atmosphere.But the deficiency of this patent is to have generated a large amount of high boiling material in the reaction process, wherein whenever obtains the 927g diox and will generate the 147g high boiling material.The generation of these high boiling material has reduced the atom utilization of iso-butylene.
Patent such as US3773847A1, US3972955A1 also discloses the manufacture method of diox, but this several method is all failed to solve reaction and produced this difficult problem with a large amount of high boiling material.
Summary of the invention
The present invention is directed to formaldehyde and iso-butylene and under acid catalysis, take place have a large amount of high boiling material to generate this difficult problem in the prins reaction process, a kind of preparation method that can effectively reduce the high boiling material growing amount, improve the diox of diox yield is provided.
Purpose of the present invention can reach by following embodiment.
A kind of preparation method of diox, it is characterized in that, formaldehyde, iso-butylene, acid catalyst and auxiliary agent are reacted in sealed vessel, then reaction product is extracted with aliphatic hydrocarbon, again extraction liquid is distilled, obtain diox, the purity and the yield height of the low ， diox of the content of by-product high boiling material in the reaction product.
Wherein formaldehyde can be solution, and its strength of solution can be but be not limited between 37～40%; Iso-butylene can be that pure iso-butylene also can be the C 4 fraction that contains iso-butylene;
Wherein the mol ratio of formaldehyde and iso-butylene can be between 2～15;
Wherein acid catalyst is phosphoric acid or sulfuric acid; If use phosphoric acid as catalyzer, pure heavy 5～75% of the system gross weight that accounts for of phosphoric acid then, if use sulfuric acid as catalyzer, pure heavy 3～30% of the system gross weight that accounts for of sulfuric acid then;
Wherein auxiliary agent can be a thanomin, oil of mirbane, and N-Methyl pyrrolidone, o-NP, one of Sodium Nitrite also can be above-mentioned several combination of compounds, its quality accounts for 0.01～2% of system gross weight;
Wherein the mass ratio of the quality of water and formaldehyde should be 1.7～3 in the reaction system;
Wherein Fan Ying temperature can be between 70～110 ℃;
Wherein Fan Ying pressure is the saturated vapor pressure of blending ingredients under temperature of reaction.
The preparation method of a kind of diox of the present invention, under acid catalysis, take place have a large amount of high boiling material to generate this difficult problem in the prins reaction process at formaldehyde and iso-butylene, can effectively reduce the purity and the yield of high boiling material growing amount, raising diox, utilize obviously the descend yield of ， diox of the content of high boiling material in the inventive method gained diox product can reach 89～95%.
Embodiment
Below by embodiment the present invention is done further explanation.
According to an embodiment of the present invention, our iso-butylene of selection can be that pure iso-butylene also can be the C4 component that contains the part iso-butylene.The side reaction of using pure iso-butylene to take place is few, uses the C4 component side reaction that contains iso-butylene many.Contingent side reaction can be referring to patent: US2962507 in this reaction process.Use method of the present invention, no matter be with pure iso-butylene or contain the C4 component of iso-butylene, the possibility that side reaction takes place all reduces greatly.
According to embodiment of the present invention, the formaldehyde that we select can be the formaldehyde solution that contains formaldehyde, including but not limited to concentration 37～40%.According to concrete implementation method, for the concentration of dilute catalyst acid not, we also can select the formaldehyde raw material of Paraformaldehyde 96 as this reaction process for use.
According to embodiment of the present invention, the acid catalyst that we select can be a mineral acid, can be sulfuric acid or phosphoric acid specifically.The concentration of selected acid can be any concentration, but must guarantee within the pure heavy value certain limit that accounts for the system gross weight of acid, specifically, if use sulfuric acid as catalyzer, pure important 3～30% of the system gross weight that accounts for of vitriolic so, if use phosphoric acid as catalyzer, so pure heavy 5～75% of the system gross weight that accounts for of phosphoric acid.Under identical temperature of reaction, the concentration of acid is high more, and then Fan Ying speed is fast more, but too high as the concentration of tartaric acid, then may cause diox optionally to reduce, even can cause the cracking of diox; But the concentration as tartaric acid is too low, and the speed of reaction will reduce greatly.Therefore select suitable acid concentration, to reacting most important.
According to embodiment of the present invention, the mol ratio of formaldehyde and iso-butylene is greater than the stoichiometric coefficient ratio of this reaction formaldehyde and iso-butylene, the mol ratio that is formaldehyde and iso-butylene is greater than 2, if the mol ratio of formaldehyde and iso-butylene less than 2, can cause the selectivity of diox to reduce.According to chemical reaction equilibrium, we know that the molar ratio of formaldehyde and iso-butylene is big more, and reaction helps the generation of diox more, but in the real process, the unlimited amount that increases formaldehyde is unpractical, so the mol ratio of formaldehyde and iso-butylene generally is controlled between 2～15.
According to embodiment of the present invention, the auxiliary agent that we select is to reduce the compound that side reaction takes place, and these auxiliary agents can be but be not limited to thanomin specifically, oil of mirbane, N-Methyl pyrrolidone, o-NP, Sodium Nitrite etc.The amount that these auxiliary agents add can be 0.01%～2% of a system gross weight.
According to embodiment of the present invention, the content of water will be controlled within certain scope in the system, and the content of water is too high, can cause a large amount of generations of the trimethyl carbinol, and the content of water is crossed and can be made the content of high boiling material increase at least, therefore wants the content of strict control water.Specifically, the mass ratio of the quality of water and formaldehyde preferably is controlled at 1.7～3.
According to embodiment of the present invention, the temperature of reaction will be controlled between 70～110 ℃, and too low temperature makes that the speed of reaction is low excessively, and temperature is too high, can cause the generation of carbonization.
According to embodiment of the present invention, the pressure of reaction system is under the temperature of reaction, the vapour pressure sum of various reaction mixtures in the system.
Embodiment 1
Formaldehyde solution 126.7g with 37%, 99.93% iso-butylene 35g, 98% sulfuric acid 22.9g, o-NP 1.85g joins in the autoclave, and powerful the stirring behind 80 ℃ of reaction 2h, extracts reaction product with hexanaphthene.With the extraction liquid distillation, De diox 68.1g wherein contains high boiling material 0.27g then.
Comparative Examples 1
Use identical experiment condition with embodiment 1, but do not add o-NP, after the identical operations method, obtain diox 47.1g, wherein contain high boiling material 13.2g.
Embodiment 2
Use identical experiment condition with embodiment 1, but change o-NP the thanomin of equal in quality into, after the identical operations method, obtain diox 67.2g, wherein contain high boiling material 0.27g.
Embodiment 3
Use identical experiment condition with embodiment 1, but change o-NP the oil of mirbane of equal in quality into, after the identical operations method, obtain diox 69.4g, wherein contain high boiling material 0.28g.
Embodiment 4
Use identical experiment condition with embodiment 1, but change o-NP the N-Methyl pyrrolidone of equal in quality into, after the identical operations method, obtain diox 65.2g, wherein contain high boiling material 0.26g.
Embodiment 5
Use identical experiment condition with embodiment 1, but change o-NP the Sodium Nitrite of equal in quality into, after the identical operations method, obtain diox 63.1g, wherein contain high boiling material 0.25g.
Embodiment 6
Use identical experiment condition with embodiment 1, but the quality of o-NP becomes 0.92g, after the identical operations method, obtains diox 68.9g, high boiling material 0.28g.
Embodiment 7
Formaldehyde solution 130.3g with 37%, 99.93% iso-butylene 35g, 85% phosphoric acid 27.9g, o-NP 1.88g joins in the autoclave, and powerful the stirring behind 80 ℃ of reaction 2h, extracts reaction product with hexanaphthene.Then with extraction liquid distillation, De diox 69.6g, high boiling material 0.21g.
Embodiment 8
Formaldehyde solution 130.3g with 37% contains the C4 gas 81.5g of iso-butylene 43%, 85% phosphoric acid 27.9g, and o-NP 1.88g joins in the autoclave, and powerful the stirring behind 80 ℃ of reaction 2h, extracts reaction product with hexanaphthene.Then with extraction liquid distillation, De diox 65.8g, high boiling material 0.32g.
Claims (6)
1, a kind of 4,4-dimethyl-1, the preparation method of 3-diox, it is characterized in that, formaldehyde solution, pure iso-butylene or the C 4 fraction, acid catalyst and the auxiliary agent that contain iso-butylene are reacted in sealed vessel, then reaction product is extracted with aliphatic hydrocarbon, again extraction liquid is distilled, obtain 4,4-dimethyl-1,3-diox;
Wherein auxiliary agent is any one or several combination in thanomin, oil of mirbane, N-Methyl pyrrolidone, o-NP, the Sodium Nitrite, and its quality accounts for 0.01～2% of system gross weight.
2, according to claim 1 a kind of 4,4-dimethyl-1, the preparation method of 3-diox is characterized in that, the concentration of formaldehyde solution is 37～40%.
3, according to claim 1 a kind of 4,4-dimethyl-1, the preparation method of 3-diox is characterized in that, wherein the mol ratio of formaldehyde and iso-butylene is between 2～15.
4, according to claim 1 a kind of 4,4-dimethyl-1, the preparation method of 3-diox is characterized in that, wherein acid catalyst is phosphoric acid or sulfuric acid; Phosphoric acid is as catalyzer, pure heavy 5～75% of the system gross weight that accounts for of phosphoric acid then, and sulfuric acid is as catalyzer, then pure heavy 3～30% of the system gross weight that accounts for of sulfuric acid.
5, according to claim 1 a kind of 4 ,/4-dimethyl-1, the preparation method of 3-diox is characterized in that, wherein Fan Ying temperature is between 70～110 ℃.
6, according to claim 1 a kind of 4,4-dimethyl-1, the preparation method of 3-diox is characterized in that, wherein Fan Ying pressure is the saturated vapor pressure of blending ingredients under temperature of reaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810013740A CN100586942C (en) | 2008-01-04 | 2008-01-04 | Production method of dioxane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810013740A CN100586942C (en) | 2008-01-04 | 2008-01-04 | Production method of dioxane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101220019A CN101220019A (en) | 2008-07-16 |
| CN100586942C true CN100586942C (en) | 2010-02-03 |
Family
ID=39630130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200810013740A Active CN100586942C (en) | 2008-01-04 | 2008-01-04 | Production method of dioxane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100586942C (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104974129B (en) * | 2014-04-03 | 2019-03-29 | 中国石油化工股份有限公司 | For separating extractant and its application of the high-boiling components generated in 4,4- dimethyl -1,3- dioxane production process |
| CN104974130B (en) * | 2014-04-03 | 2019-03-29 | 中国石油化工股份有限公司 | A method of separation preparation 4,4- dimethyl -1,3- dioxane |
| CN104876786B (en) * | 2015-01-28 | 2017-03-29 | 盘锦和运新材料有限公司 | The technology of olefine aldehydr preparing isoprene through liquid phase method |
| RU2658839C2 (en) * | 2016-09-12 | 2018-06-25 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Башкирский государственный университет" | Application of carbon nanotubes to increase selectivity in production of 4,4-dimethyl-1,3-dioxane |
| RU2663294C1 (en) * | 2018-03-07 | 2018-08-03 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Башкирский государственный университет" | Application of porous polyphenylenephthalide to increase selectivity in production of 4,4-dimethyl-1,3-dioxane |
| CN109761950B (en) * | 2019-01-25 | 2020-11-03 | 浙江师范大学 | Method for preparing 4, 4-dimethyl-1, 3-dioxane |
| CN111747910B (en) * | 2019-03-28 | 2022-09-16 | 万华化学集团股份有限公司 | Preparation method of gamma-decalactone |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB825034A (en) * | 1957-03-22 | 1959-12-09 | Inst Francais Du Petrole | Improvements in or relating to the production of 4:4-dimethyl-meta-dioxan |
| US2962507A (en) * | 1957-03-22 | 1960-11-29 | Inst Francais Du Petrole | Process for making 4, 4-dimethyl-metadioxane |
| US3773847A (en) * | 1970-09-09 | 1973-11-20 | Bayer Ag | Process for the preparation of isoprene from isobutene and formaldehyde |
| US3972955A (en) * | 1973-09-22 | 1976-08-03 | Bayer Aktiengesellschaft | Process for preparation of isoprene |
-
2008
- 2008-01-04 CN CN200810013740A patent/CN100586942C/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB825034A (en) * | 1957-03-22 | 1959-12-09 | Inst Francais Du Petrole | Improvements in or relating to the production of 4:4-dimethyl-meta-dioxan |
| US2962507A (en) * | 1957-03-22 | 1960-11-29 | Inst Francais Du Petrole | Process for making 4, 4-dimethyl-metadioxane |
| US3773847A (en) * | 1970-09-09 | 1973-11-20 | Bayer Ag | Process for the preparation of isoprene from isobutene and formaldehyde |
| US3972955A (en) * | 1973-09-22 | 1976-08-03 | Bayer Aktiengesellschaft | Process for preparation of isoprene |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101220019A (en) | 2008-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100586942C (en) | Production method of dioxane | |
| US2457866A (en) | Condensation of alcohols | |
| US2116182A (en) | Production of mercaptans | |
| CN105967978B (en) | Aqueous methyl butenol isomery is combined to prenol | |
| US5831134A (en) | Continuous production process of tertiary alcohols by radical addition of secondary alcohols to alkenes | |
| EP3015446B1 (en) | Method for producing allyl alcohol and allyl alcohol produced thereby | |
| CN107011191B (en) | Method for producing N,N-dimethyldiglycolamine and co-producing N,N-dimethylethanolamine | |
| EP2589586B1 (en) | Method for preparing chlorohydrins composition and method for preparing epichlorohydrin using chlorohydrins composition prepared thereby | |
| KR20120002338A (en) | Method for producing chlorohydrin compositions and method for producing epichlorohydrin using chlorohydrin compositions prepared by the method | |
| EP1123264A1 (en) | PROCESS FOR THE MANUFACTURE OF $g(a),$g(a)-BRANCHED CARBOXYLIC ACIDS | |
| US20140364351A1 (en) | Process for preparing a mixture of alcohols | |
| EP2594549B1 (en) | Method for preparing a composition of chlorohydrins | |
| US8933279B2 (en) | Method for preparing a mixture of alcohols | |
| CN108238875B (en) | Synthesis method of bromoisobutenyl methyl ether and application of bromoisobutenyl methyl ether in preparation of C14 aldehyde | |
| CN101209965A (en) | Method for preparing dehydrolinalyl acetate from dehydrolinalool | |
| EP1852410B1 (en) | Transport of ethyne in form of alpha-alkynols as ethyne precursors | |
| KR20190056665A (en) | Process for preparing 2,2,4,4-tetramethyl-1,3-cyclobutanediol | |
| JP5798871B2 (en) | Method for producing isoprene | |
| CN108299171B (en) | Method for synthesizing methyl heptenone from 2-methyl-3-butene-2-ol | |
| CN104496808B (en) | A kind of method of the secondary butyl ester of separating acetic acid from acetic acid with C4 reacted mixture | |
| CN111302919A (en) | Method for synthesizing high-content dihydrojasmone spice | |
| EP2943459A1 (en) | Production of acrylic acid | |
| KR20150101768A (en) | Method for preparing glycidol through successive catalytic reaction | |
| EP1860090B1 (en) | Method for processing the glycerol phase from transestrification of fatty acid triglycerols | |
| CN114516786B (en) | Method for preparing citral intermediate by photocatalysis |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |