CN116063246A - Method for preparing 1,2-pentanediol and 2, 3-pentalene oxide - Google Patents
Method for preparing 1,2-pentanediol and 2, 3-pentalene oxide Download PDFInfo
- Publication number
- CN116063246A CN116063246A CN202111270612.9A CN202111270612A CN116063246A CN 116063246 A CN116063246 A CN 116063246A CN 202111270612 A CN202111270612 A CN 202111270612A CN 116063246 A CN116063246 A CN 116063246A
- Authority
- CN
- China
- Prior art keywords
- reaction
- pentene
- tower
- carbon
- pentanediol
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 45
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 title claims abstract description 34
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims abstract description 73
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims abstract description 63
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 55
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 55
- 238000006243 chemical reaction Methods 0.000 claims abstract description 51
- 239000002994 raw material Substances 0.000 claims abstract description 32
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000005977 Ethylene Substances 0.000 claims abstract description 22
- 238000006735 epoxidation reaction Methods 0.000 claims abstract description 22
- 239000002808 molecular sieve Substances 0.000 claims abstract description 17
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 17
- UGACIEPFGXRWCH-UHFFFAOYSA-N [Si].[Ti] Chemical compound [Si].[Ti] UGACIEPFGXRWCH-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000007800 oxidant agent Substances 0.000 claims abstract description 6
- 230000001590 oxidative effect Effects 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000000197 pyrolysis Methods 0.000 claims description 15
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 14
- BCJPEZMFAKOJPM-UHFFFAOYSA-N 2-ethyl-3-methyloxirane Chemical compound CCC1OC1C BCJPEZMFAKOJPM-UHFFFAOYSA-N 0.000 claims description 13
- 230000003197 catalytic effect Effects 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 238000011084 recovery Methods 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 239000003495 polar organic solvent Substances 0.000 claims description 9
- 230000035484 reaction time Effects 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims description 7
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910019440 Mg(OH) Inorganic materials 0.000 claims description 2
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 239000012847 fine chemical Substances 0.000 abstract description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 230000002194 synthesizing effect Effects 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000005156 Dehydration Diseases 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000004280 Sodium formate Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- -1 oxygen organic acid Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
- 235000019254 sodium formate Nutrition 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing 1,2-pentanediol and 2, 3-pentalene oxide. The method takes a titanium-silicon molecular sieve as a catalyst and hydrogen peroxide as an oxidant, takes the residual carbon five of the cracked ethylene as a raw material, and obtains 1,2-pentanediol and 2, 3-pentalene oxide through epoxidation reaction and hydrolysis reaction. The method has the advantages of environmental protection, sufficient reaction raw material supply, low price, and the 1-pentene and 2-pentene in the residual carbon five are used for preparing high added value fine chemicals, thereby improving the comprehensive utilization level of the carbon five resources.
Description
Technical Field
The invention belongs to the technical field of olefin catalytic epoxidation reaction for synthesizing alkylene oxide, and in particular relates to a method for obtaining 1,2-pentanediol and 2, 3-pentalene oxide by using a titanium-silicon molecular sieve as a catalyst and hydrogen peroxide as an oxidant and raffinate carbon five of cracked ethylene as a raw material through epoxidation reaction and hydrolysis reaction.
Background
l, 2-pentanediol, also known as 1, 2-dihydroxypentane, and the English name is 1, 2-pentandiol, is a key intermediate for synthesizing the systemic fungicide propiconazole, and is also an important raw material for producing products such as polyester fibers, surfactants, medicines and the like. The method for producing the 1,2-pentanediol by using the 1-pentene as a raw material through oxidation and saponification of oxygen organic acid is a main method for industrially producing the 1, 2-pentanediol. U.S. patent No. 4605795 discloses a continuous phase process for preparing 1,2-pentanediol by epoxidation of 1-pentene and peroxypropionic acid in a benzene solvent, but the recovery of the by-products produced is difficult and causes environmental pollution. US4479021 discloses a continuous production process of 1,2-pentanediol, which uses 1-pentene and peracetic acid as raw materials to produce 1,2-pentanediol, but peracetic acid is easy to explode, and the problem of safety control of peracetic acid is not mentioned in the literature. CN155268 discloses a method for preparing 1,2-pentanediol by using n-pentene, formic acid and hydrogen peroxide as raw materials, wherein the oxidation reaction temperature is-20 to-10 ℃, the molar ratio of n-pentene to formic acid is 1:1.6-2.6, the molar ratio of formic acid to hydrogen peroxide is 1:0.4-0.9, and after the oxidation reaction is completed, the 1,2-pentanediol is obtained through saponification reaction and extractive distillation, and the yield is 72%. The patent adopts low-temperature reaction, peroxyformic acid replaces peroxyacetic acid, the process safety is improved, but the patent also has some problems: the oxidation reaction has more formic acid excess, byproducts are easy to form in the reaction process, the saponification reaction consumes more NaOH, and the generated sodium formate needs to be separated, recycled and utilized, so that the process flow is more complicated. After the saponification reaction is completed, extracting and separating 1,2-pentanediol, extracting organic phase residual sodium formate, and promoting the decomposition of 1,2-pentanediol during rectification. In addition, the 1-pentene which is a reaction raw material belongs to a-olefin containing odd carbon atoms, mainly comes from dehydration of 1-amyl alcohol or Fischer-Tropsch synthesis, has low market output and is more expensive.
In order to solve the defects of the existing 1,2-pentanediol synthesis process, the inventor adopts a titanium-silicon molecular sieve as a catalyst, preferably a titanium-silicon molecular sieve TS-1 as a catalyst, hydrogen peroxide as an oxidant, and takes low-price pyrolysis ethylene to extract residual carbon five raw materials, and the 1-pentene, 2-pentene and hydrogen peroxide in the residual carbon five react to generate 1,2-pentane, 2, 3-pentane and water, so that the reaction has the advantages of environmental protection and the like, and the used pyrolysis ethylene to extract residual carbon five raw materials is cheap, has sufficient market supply and ensures raw material sources. At present, the ethylene yield in China is close to 2000 ten thousand tons/year, the cracking carbon five yield reaches 200 ten thousand tons/year, and after dicyclopentadiene, isoprene, piperylene and 2-methyl butene-1 and 2-methyl butene-2 in the ethylene are removed by a carbon five separation device, the residual carbon five scale reaches 40 ten thousand tons/year. In the residual carbon five, the main component is pentane, the mass percentage of 1-pentene is 5-12%, and the mass percentage of 2-pentene is 20-40%. The method adopts precise rectification to separate 1-pentene and 2-pentene from the residual carbon five, the theoretical plate number and the reflux ratio of the rectifying tower are large, the energy consumption is high, the main application of the residual carbon five at present is to prepare pentane through hydrogenation reaction, and the 1-pentene and 2-pentene in the residual carbon five are not effectively utilized.
The method provided by the invention is used for synthesizing the 1,2-pentanediol and the 2, 3-pentalene, has the advantages of sufficient raw material supply, low price, greatly improved reaction safety, obviously reduced discharge of three wastes and simultaneously provides a high accessory value utilization method for cracking the 1-pentene and the 2-pentene in the ethylene residual carbon five.
According to the method provided by the invention, 1-pentene and 2-pentene in the residual carbon five are utilized to react with hydrogen peroxide to form 1,2-pentane oxide and 2, 3-pentane oxide under the catalysis of a titanium-silicon molecular sieve TS-1, and the reaction formula is as follows:
as can be seen from the reaction scheme, 1, 2-pentalene oxide and 2, 3-pentalene oxide are isomers, and the invention is of little significance if 1, 2-pentalene oxide and 2, 3-pentalene oxide cannot be effectively separated. In order to solve this problem, the inventors found through experiments that 1, 2-pentalene and 2, 3-pentalene have very different hydrolysis reaction properties in an alkaline aqueous solution, 1, 2-pentalene is easily hydrolyzed to form 1,2-pentanediol, and 2, 3-pentalene does not undergo hydrolysis reaction in a 30% KOH aqueous solution even at 120 ℃. The normal pressure boiling point of the 1,2-pentanediol is 206 ℃, the boiling point of the 2, 3-epoxypentane is about 90 ℃, the boiling points of the two are very different, and the two are easy to separate by rectification separation. Therefore, the reaction mixture of the 1, 2-epoxypentane and the 2, 3-epoxypentane is hydrolyzed to generate the 1,2-pentanediol by the alkali catalytic hydrolysis reaction, thereby effectively solving the separation problem of the 1, 2-epoxypentane and the 2, 3-epoxypentane. The inventor firstly discovers the difference of the hydrolytic properties of the 1, 2-epoxypentane and the 2, 3-epoxypentane, so that the epoxidation reaction of the 1-pentene and the 2-pentene in the residual carbon five has industrial development value.
Disclosure of Invention
In order to overcome the defects of the existing technology for synthesizing 1,2-pentanediol by a peroxy organic acid method, the invention provides a method for preparing 1,2-pentanediol and 2, 3-pentalene oxide. The method takes a titanium-silicon molecular sieve as a catalyst and hydrogen peroxide as an oxidant, takes the residual carbon five of the cracked ethylene as a raw material, and obtains 1,2-pentanediol and 2, 3-pentalene oxide through epoxidation reaction and hydrolysis reaction. The method has the advantages of environmental protection, sufficient reaction raw material supply, low price, and the 1-pentene and 2-pentene in the residual carbon five are used for preparing high added value fine chemicals, thereby improving the comprehensive utilization level of the carbon five resources.
The technical scheme of the invention is specifically introduced as follows:
the invention provides a method for preparing 1,2-pentanediol and 2, 3-pentalene oxide, which comprises the following steps:
(1) The method comprises the steps of taking pyrolysis ethylene raffinate carbon five as a reaction raw material, taking hydrogen peroxide as an oxidant, fully contacting the reaction material with a titanium-silicon molecular sieve TS-1 catalyst in a catalytic epoxidation reactor in a polar organic solvent to perform catalytic oxidation reaction, and performing pyrolysis on 1-pentene in the pyrolysis ethylene raffinate carbon five,2-pentene reacts with H under the catalysis of titanium-silicon molecular sieve TS-1 2 O 2 Generating epoxidation reaction to generate 1, 2-epoxypentane, 2, 3-epoxypentane and water;
wherein the sum of the mole numbers of the 1-pentene and the 2-pentene in the residual carbon five raw material of the cracked ethylene is equal to H 2 O 2 The molar ratio is 1:1.5-1: 3.3, the temperature of the catalytic epoxidation reaction is 50-90 ℃, the reaction pressure is 0.5-7.0 MPa (absolute pressure), and the reaction time is 1-10 hours;
(2) The reaction product obtained in the step (1) adopts a double-tower serial continuous rectification process, carbon five components which do not undergo epoxidation reaction are collected at the top of a first rectification tower, tower kettle materials are conveyed to a second rectification tower, polar organic solvents are collected at the top of the second rectification tower, and a mixture of 1, 2-epoxypentane, 2, 3-epoxypentane and water is collected at the tower kettle;
(3) And (3) conveying the mixed material of 1.2-pentalene oxide, 2, 3-pentalene oxide and water collected in the second rectifying tower kettle in the step (2) into a hydrolysis reactor, and carrying out hydrolysis reaction on the 1, 2-pentalene oxide under the action of an alkaline catalyst to generate 1,2-pentanediol, wherein the 2, 3-ethylene oxide is not hydrolyzed, so as to obtain an aqueous solution of the 1,2-pentanediol and the 2, 3-pentalene oxide.
Further, the sum of the mole numbers of the 1-pentene and the 2-pentene in the ethylene-extracting carbon five raw material in the step (1) is cracked to be H 2 O 2 The molar ratio is 1:2.2-1: 2.5, the temperature of the catalytic epoxidation reaction is 60-80 ℃, the reaction pressure is 2.0-6.0 MPa, and the reaction time is 4-6 hours.
Further, the titanium silicalite molecular sieve TS-1 belongs to Pentasil type heteroatom molecular sieve, is orthorhombic, has a three-dimensional pore structure represented by ZSM-5, consists of Z-shaped channels and elliptic straight channels intersected with the Z-shaped channels, has the crystallinity of 90% or more and the BET specific surface area of 350m or more 2 Per g, pore diameter of 0.56-0.58 nm, siO 2 /TiO 2 30-200 (molar ratio), burning (550 ℃ C., 2 hr) less than or equal to 5%.
In the present invention, the preparation method of the TS-1 titanium silicalite molecular sieve catalyst is disclosed in the following literature, and any improved method based on the literature is also included:
[1]Taramasso.Preparation of porous crystalline synthetic material comprised of silicon and titanium oxides[P].US:4410501,1983.
[2]Thangaraj A,Eapen M J,Sivasanker S,et al.Studies on the synthesis of titanium silicalite,TS-1[J].Zeolites,1992,12(8):943-950.
further, the catalytic oxidation reaction in the step (1) adopts a fixed bed continuous reaction or batch kettle reaction process; a fixed bed continuous loop reaction process is preferred.
Further, when the batch kettle reaction process is adopted, the catalyst dosage is 5-50% of the total mass of 1-pentene and 2-pentene in the carbon five pumped into the kettle reactor; when adopting fixed bed continuous reaction, the volume space velocity of the total material fed into the reactor is 0.1-1.0 h -1 。
Further, when the batch kettle reaction process is adopted, the catalyst dosage is 10% -30% of the total mass of 1-pentene and 2-pentene in the carbon five pumped into the kettle reactor; when adopting fixed bed continuous reaction, the volume space velocity of the total material fed into the reactor is 0.2-0.8 h -1 。
Further, the polar organic solvent in the step (1) is selected from one or more of methanol, ethanol, n-propanol, isopropanol, tertiary butanol, acetone, butanone, isobutyl ketone, pentanone, cyclopentanone, heptanone, tetrahydrofuran, tetrahydropyran, acetonitrile; the preferred polar organic solvent is acetone or methanol.
Further, the volume ratio of the polar organic solvent to the pyrolysis ethylene raffinate carbon five raw materials is 5: 1-10:1, preferably the volume ratio is 5: 1-8:1.
Further, H in the hydrogen peroxide in the step (1) 2 O 2 The mass percentage of (C) is 30-70 wt%, preferably 40-50 wt%.
Further, in the step (2), a double-tower serial continuous rectification process is adopted, the theoretical plate number of the first rectification tower is 30-60, the tower top pressure is 0.1-0.3 MPa (absolute pressure), the tower top temperature is 26.0-66.1 ℃, the tower bottom temperature is 57.1-90.0 ℃, and the reflux ratio is 5: 1-10:1, and the recovery rate of the carbon five fraction at the top of the rectifying tower is more than 95 percent; the second rectifying tower adopts normal pressure rectification, theoretical plate number is 30-60, tower top temperature is 55.8-64.4 ℃, tower bottom temperature is 78.3-99.4, reflux ratio is 2:1-6:1, and recovery rate of the tower top of the solvent rectifying tower is 92.0-100%.
Further, the hydrolysis reaction temperature in the step (3) is controlled to be 50-120 ℃, the hydrolysis reaction pressure is 0.1-0.3 MPa (absolute pressure), and the reaction time is 1-10 hours; the preferable hydrolysis reaction temperature is controlled between 70 and 90 ℃, the reaction pressure is normal pressure, and the reaction time is 4 to 5 hours.
Further, the basic catalyst for hydrolysis in the step (3) is selected from the group consisting of hydroxides of alkali metals or alkaline earth metals of the periodic table or aqueous solutions thereof, preferably KOH, naOH, ca (OH) 2 、Mg(OH) 2 、Ba(OH) 2 More preferably KOH, naOH; in the hydrolysis reaction system, alkali metal or alkaline earth metal hydroxide is used as solute to form alkaline aqueous solution with water in the reaction raw material, wherein the mass percent of the solute in the alkaline aqueous solution is 5-20wt%, preferably 10-15wt%.
The invention uses the pyrolysis ethylene residual carbon five as the reaction raw material, and the components thereof comprise: the mass percentage of the 1-pentene is 5.0-15.3%, the mass percentage of the 2-pentene is 12.0-40.0%, the mass percentage of the isopentene is less than or equal to 0.5%, and the balance is n-pentane and isopentane.
Compared with the prior art, the invention has the beneficial effects that:
the invention provides a method for synthesizing 1,2-pentanediol and 2, 3-epoxypentane by taking a mixture of 1-pentene and 2-pentene in the residual carbon five as raw materials, which effectively solves the problems of high price and low productivity of the 1-pentene and 2-pentene in the current market, provides a more economic synthesis method for producing the 1,2-pentanediol and 2, 3-epoxypentane, and simultaneously provides a new method for comprehensively utilizing the residual carbon five.
Drawings
FIG. 1 is a process flow diagram of the present invention.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
The present invention is further illustrated by the following examples, but the present invention is not limited to the examples. The product yield in the specification is defined, and the reaction yield calculation formula is as follows:
yield of 1, 2-pentalene reaction = 100% moles of 1, 2-pentalene in the epoxidation reaction product/moles of 1-pentene fed to the epoxidation reactor
Yield of 2, 3-pentalene reaction = 100% moles of 2, 3-pentalene in the epoxidation reaction product/moles of 2-pentene fed to the epoxidation reactor
Yield of 1,2-pentanediol = mole number of 1,2-pentanediol in hydrolysis reaction product/mole number of 1, 2-pentalene oxide charged to hydrolysis reactor 100%
Solvent overhead recovery = solvent extraction mass per hour at the top of the second rectification column/solvent mass fed to the first rectification column per hour 100%
Carbon five fraction overhead recovery = carbon five component mass withdrawn per hour at the top of the first rectifying column/carbon five component mass fed into the first rectifying column per hour 100%
Catalyst amount = TS-1 mass charged to the tank reactor/(mass of 1-pentene + mass of 2-pentene in the tank reactor) ×100%.
N-pentene mole = 1-pentene mole + 2-pentene mole
The invention uses the pyrolysis ethylene residual carbon five as the reaction raw material, and the components thereof comprise: the mass percentage of the 1-pentene is 5.0-15.3%, the mass percentage of the 2-pentene is 12.0-40.0%, the mass percentage of the isopentene is less than or equal to 0.5%, and the balance is n-pentane and isopentane.
Examples 1 to 8: kettle type reaction process for synthesizing 1, 2-epoxypentane and 2, 3-epoxypentane
In a 500ml reaction kettle, respectively adding a solvent, residual carbon five, hydrogen peroxide and a titanium-silicon molecular sieve catalyst TS-1, fixing the catalyst on the side of a cooling coil of the reaction kettle in a hanging basket manner, flushing nitrogen into the reaction kettle after feeding to set the initial reaction pressure, starting stirring, and observing the influence of the TS-1 molecular sieve catalysts with different olefin raw materials, solvents, temperatures, pressures, reaction time, feeding ratios and silicon-titanium molar ratios on the reaction. The composition of the pyrolysis ethylene raffinate carbon five feedstock used in examples 1-5: 77.0% of n-pentane, 5.5% of isopentane, 0.5% of isopentene, 5.0% of 1-pentene and 12.0% of 2-pentene, wherein the solvent used in the oxidation reaction is acetone. The composition of the pyrolysis ethylene raffinate carbon five feedstock used in examples 6-8: 65.0% of n-pentane, 4.5% of isopentane, 0.5% of isopentene, 10.0% of 1-pentene and 20.0% of 2-pentene, and the solvent used for the oxidation reaction is acetone. After the reaction was terminated, a sample was taken, the composition of the product was analyzed by gas chromatography, and the experimental results are shown in Table 1.
TABLE 1 reaction conditions for the kettle type intermittent epoxy ring of 1-pentene and 2-pentene in the carbon five residue
Examples 9 to 16: synthesis of 1, 2-epoxypentane, 2, 3-epoxypentane by fixed bed continuous reaction process
A40 ml jacketed stainless steel fixed bed reactor is heated by heat conduction oil, the reactor is 500mm long and 10mm in inner diameter, 30 ml of a 25-60 mesh titanium silicon molecular formula TS-1 catalyst is filled in the reactor, reaction materials adopt a low-inlet and high-outlet mode, and a metering pump is used for mixing a solvent, residual carbon five and hydrogen peroxide according to a process ratio and then feeding the mixture into the reactor. The composition of the five raw materials of the residual carbon of the pyrolysis ethylene used in examples 9 to 13 comprises the following components in percentage by mass: 39.7% of n-pentane, 3.3% of isopentane, 0.2% of isopentene, 15.3% of 1-pentene and 40.0% of 2-pentene, wherein acetone is used as a solvent for the epoxidation reaction, the composition of the residual five carbon raw materials used in examples 14 to 16 is the same as that of examples 6 to 8, and methanol is used as a solvent for the epoxidation reaction. The effect of temperature, pressure, reaction material ratio, mass space velocity, catalyst TS-1 silicon-titanium molar ratio on the reaction was examined separately, and the results are shown in Table 2.
TABLE 2 fixed bed epoxy Ring reaction conditions for 1-pentene and 2-pentene in the raffinate carbon five
Examples 17 to 26: double-tower serial continuous rectification for separating C5, solvent, 1, 2-epoxypentane and 2, 3-epoxypentane
The reaction products of examples 6, 7 and 8 were combined and had the following mass percentages: 78.8% of acetone, 9.2% of n-pentane, 0.6% of isopentane, 0.4% of 1-pentene, 0.3% of 2-pentene, 0.1% of isopentene, 1.3% of 1,2-pentane oxide, 2.2% of 2, 3-pentane oxide and 6.9% of water are used as rectification raw materials in examples 17 to 23. The reaction products of examples 14, 15, 16 were used as rectification feeds for examples 24, 25, 26, respectively. The rectification separation operation adopts a double-tower serial continuous rectification separation process, the feeding speed of a first rectification tower is 100 g/h, the height of the first rectification tower is 2000mm, the inner diameter of the first rectification tower is 50mm, the volume of a tower kettle is 5L, the height of a second rectification tower is 2000mm, the inner diameter of the second rectification tower is 50mm, the volume of the tower kettle is 10L, the filling materials filled in the two towers are stainless steel theta-ring filling materials, phi 2.5 and phi 2.5, and the theoretical plate number of the rectification tower is regulated by regulating the height of the filling materials. The first rectifying tower and the second rectifying tower are fed with metering pump, the tower top fraction is produced, and the liquid level difference is utilized to overflow the liquid accumulating tray of the condenser into the storage tank. The reflux condenser at the top of the tower adopts low-temperature water at the temperature of minus 5 ℃ to condense and cool materials, the evaporation of materials at the bottom of the tower adopts an electric heating mode, and the reflux ratio controller controls the reflux quantity at the top of the tower. The solvents in the materials are acetone and methanol, under the conditions of theoretical plate, tower top temperature, pressure, tower bottom temperature, reflux ratio and the like, the rectification recovery rate of the carbon five fraction of the first rectifying tower, the recovery rate of the solvent of the tower top of the second rectifying tower and the mass percentage composition of the tower bottom materials of the second rectifying tower are respectively examined, and experimental results are respectively shown in tables 3, 4 and 5.
TABLE 3 operation of the first rectification column (column top separation recovery of five carbon fractions)
TABLE 4 operation process of second rectifying column (separation recovery solvent from top of column)
Table 5 composition of the second rectifying column bottoms in mass percent
Examples 27 to 31: hydrolysis of 1, 2-epoxypentane
Mixing the materials in the tower bottoms of the second rectifying towers in the embodiments 17-23, and uniformly mixing the materials in percentage by mass: 10.8% of 1, 2-pentalene, 19.5% of 2, 3-pentalene, 63.3% of water and 6.4% of solvent, 300 ml of materials are taken, the materials are put into a 500ml kettle reactor with mechanical stirring, KOH or NaOH is added, the dosage of alkali is controlled, so that water and alkali in hydrolysis reaction materials form aqueous solution, the mass percentage of KOH or NaOH is 5% -20%, a stirrer is started, the temperature is raised, the materials are fully mixed, the hydrolysis reaction is started, the influence of reaction temperature, pressure, alkali mass fraction and reaction time on the hydrolysis reaction is examined, and experimental results are shown in table 6. The hydrolysis reaction product can be obtained by utilizing the general chemical separation and rectification technology, and the separated alkali liquor can be reused as a catalyst after dehydration treatment.
TABLE 6 hydrolysis reaction conditions of 1, 2-epoxypentane
While the preferred embodiments of the present invention have been illustrated and described, the present invention is not limited to the embodiments, and various equivalent modifications and substitutions can be made by one skilled in the art without departing from the spirit of the present invention, and these equivalent modifications and substitutions are intended to be included in the scope of the present invention as defined in the appended claims.
Claims (12)
1. A process for preparing 1,2-pentanediol, 2, 3-pentalene oxide, comprising:
(1) The method comprises the steps of taking pyrolysis ethylene raffinate carbon five as a reaction raw material, taking hydrogen peroxide as an oxidant, fully contacting the reaction material with a titanium silicalite molecular sieve TS-1 catalyst in a catalytic epoxidation reactor in a polar organic solvent to perform catalytic oxidation reaction, and reacting 1-pentene and 2-pentene in the pyrolysis ethylene raffinate carbon five with H under the catalytic action of the titanium silicalite molecular sieve TS-1 2 O 2 Generating epoxidation reaction to generate 1, 2-epoxypentane, 2, 3-epoxypentane and water;
wherein the sum of the mole numbers of the 1-pentene and the 2-pentene in the residual carbon five raw material of the cracked ethylene is equal to H 2 O 2 The molar ratio is 1:1.5-1: 3.3, the temperature of the catalytic epoxidation reaction is 50-90 ℃, the reaction pressure is 0.5-7.0 MPa (absolute pressure), and the reaction time is 1-10 hours;
the pyrolysis ethylene raffinate carbon five is used as a reaction raw material, and comprises the following components: the mass percentage of the 1-pentene is 5.0-15.3%, the mass percentage of the 2-pentene is 12.0-40.0%, the mass percentage of the isopentene is less than or equal to 0.5%, and the balance is n-pentane and isopentane;
(2) The reaction product obtained in the step (1) adopts a double-tower serial continuous rectification process, carbon five components which do not undergo epoxidation reaction are collected at the top of a first rectification tower, tower kettle materials are conveyed to a second rectification tower, polar organic solvents are collected at the top of the second rectification tower, and a mixture of 1, 2-epoxypentane, 2, 3-epoxypentane and water is collected at the tower kettle;
(3) And (3) conveying the mixed material of 1.2-pentalene oxide, 2, 3-pentalene oxide and water collected in the second rectifying tower kettle in the step (2) into a hydrolysis reactor, and carrying out hydrolysis reaction on the 1, 2-pentalene oxide under the action of an alkaline catalyst to generate 1,2-pentanediol, wherein the 2, 3-ethylene oxide is not hydrolyzed, so as to obtain an aqueous solution of the 1,2-pentanediol and the 2, 3-pentalene oxide.
2. The method according to claim 1, characterized in that: the sum of the mole numbers of the 1-pentene and the 2-pentene in the ethylene-extracting carbon five raw material in the step (1) is equal to H 2 O 2 The molar ratio is 1:2.2-1: 2.6, the temperature of the catalytic epoxidation reaction is 60-80 ℃, the reaction pressure is 2.0-6.0 MPa, and the reaction time is 4-6 hours.
3. The method according to claim 1, characterized in that: the titanium-silicon molecular sieve TS-1 belongs to Pentasil type heteroatom molecular sieve, is orthorhombic, has a three-dimensional pore structure represented by ZSM-5, consists of Z-shaped channels and elliptic straight channels intersected with the Z-shaped channels, has crystallinity of 90% or more and BET specific surface area of 350m or more 2 Per g, pore diameter of 0.56-0.58 nm, siO 2 /TiO 2 30-200 (molar ratio), burning (550 ℃ C., 2 hr) less than or equal to 5%.
4. The method according to claim 1, characterized in that: the catalytic oxidation reaction in the step (1) adopts a fixed bed continuous reaction or batch kettle reaction process.
5. The method according to claim 4, wherein: when the intermittent kettle type reaction process is adopted, the catalyst dosage is 5-50% of the total mass of 1-pentene and 2-pentene in the residual carbon five pumped into the kettle type reactor; when adopting fixed bed continuous reaction, the volume space velocity of the total material fed into the reactor is 0.1-1.0 h -1 。
6. The method according to claim 1, characterized in that: the polar organic solvent in the step (1) is methanol or acetone.
7. The method according to claim 1, characterized in that: the volume ratio of the polar organic solvent to the pyrolysis ethylene residual carbon five raw materials is 4: 1-10:1.
8. The method according to claim 1, characterized in that: h in the hydrogen peroxide in the step (1) 2 O 2 The mass percentage of (2) is 30-70 wt%.
9. The method according to claim 1, characterized in that: in the step (2), a double-tower serial continuous rectification process is adopted, the theoretical plate number of a first rectification tower is 30-60, the tower top pressure is 0.1-0.3 MPa (absolute pressure), the tower top temperature is 26.0-66.1 ℃, the tower bottom temperature is 57.1-90.0 ℃, and the reflux ratio is 5: 1-10:1, and the recovery rate of the carbon five fraction at the top of the rectifying tower is more than 95 percent; the second rectifying tower adopts normal pressure rectification, theoretical plate number is 30-60, tower top temperature is 55.8-64.2 ℃, tower bottom temperature is 78.3-99.4, reflux ratio is 2:1-6:1, and recovery rate of the tower top of the solvent rectifying tower is 92.0-100%.
10. The method according to claim 1, characterized in that: the hydrolysis reaction temperature in the step (3) is controlled to be 50-120 ℃, the hydrolysis reaction pressure is 0.1-0.3 MPa (absolute pressure), and the reaction time is 1-10 hours.
11. The method according to claim 1, characterized in that: the basic catalyst for hydrolysis in step (3) is selected from the group consisting of hydroxides of alkali metals or alkaline earth metals of the periodic table of elements; in the hydrolysis reaction system, hydroxide of alkali metal or alkaline earth metal is taken as solute to form alkaline aqueous solution with water in reaction raw materials, and the mass percentage of the solute in the alkaline aqueous solution is 5-20wt%.
12. The method according to claim 11, wherein: the basic catalyst is KOH, naOH, ca (OH) 2 、Mg(OH) 2 Or Ba (OH) 2 The method comprises the steps of carrying out a first treatment on the surface of the The mass percentage of the solute in the alkaline aqueous solution is 10-15 wt%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111270612.9A CN116063246A (en) | 2021-10-29 | 2021-10-29 | Method for preparing 1,2-pentanediol and 2, 3-pentalene oxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111270612.9A CN116063246A (en) | 2021-10-29 | 2021-10-29 | Method for preparing 1,2-pentanediol and 2, 3-pentalene oxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116063246A true CN116063246A (en) | 2023-05-05 |
Family
ID=86171850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111270612.9A Pending CN116063246A (en) | 2021-10-29 | 2021-10-29 | Method for preparing 1,2-pentanediol and 2, 3-pentalene oxide |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116063246A (en) |
-
2021
- 2021-10-29 CN CN202111270612.9A patent/CN116063246A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105622337B (en) | Novel reactive distillation coupling process and device for separating liquid-phase product of ethylene glycol prepared from coal | |
| CN105622338B (en) | Method, process and device for separating ethylene glycol and 1, 2-butanediol | |
| CN102372600B (en) | Separation method for glycol, propylene glycol and butylene glycol | |
| CN102372596B (en) | Method for producing glycol product by separating synthetic gas | |
| CN104355975B (en) | A kind of method of acetone two step synthesis methyl iso-butyl ketone (MIBK) | |
| CN106588589A (en) | Purification method for polyoxymethylene dimethyl ether(PODE) | |
| CN102372597B (en) | Method for separating glycol product produced from syngas | |
| CN107501042A (en) | A kind of method that isopropanol is prepared by isopropyl acetate ester hydrolysis | |
| CN107614464A (en) | The manufacture method of conjugated diene | |
| CN102453002A (en) | Method for preparing epoxypropane | |
| CN106588590A (en) | Refinement method for polyoxymethylene dimethyl ether | |
| CN113480421B (en) | System and method for preparing succinic acid by maleic anhydride hydrogenation | |
| CN106588598A (en) | Polyformaldehyde dimethyl ether refinement method | |
| CN111269096A (en) | Method for preparing ethylene glycol tert-butyl ether | |
| CN101289368A (en) | Technological process for continuously producing sec-butyl alcohol by direct hydration of n-butene | |
| CN101544537A (en) | Method for producing low carbon chemical ethanol from C6 sugar alcohol | |
| CN112174914A (en) | Method for gas-phase epoxidation reaction of olefin and hydroperoxide | |
| CN116063246A (en) | Method for preparing 1,2-pentanediol and 2, 3-pentalene oxide | |
| CN106588597A (en) | Method for purifying polyoxyethene dimethyl ether | |
| CN116063250A (en) | Method for preparing 1, 2-epoxypentane, 2, 3-epoxypentane and 1, 2-pentanediol | |
| CN116063154A (en) | Preparation method of 1,2-pentanediol and 2, 3-pentalene oxide | |
| CN116063247A (en) | Method for jointly preparing 1,2-pentanediol and 2, 3-pentalene oxide | |
| JPS6327332B2 (en) | ||
| CN103664520A (en) | Method for preparing isopropyl alcohol through hydration reaction of propylene | |
| CN112079688A (en) | Method and device for separating and refining coal and biomass-based ethylene glycol liquid-phase product |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination |