CN101792425A - Synthesis method of tetrahydrofurfuryl ethyl ether - Google Patents
Synthesis method of tetrahydrofurfuryl ethyl ether Download PDFInfo
- Publication number
- CN101792425A CN101792425A CN 201010152904 CN201010152904A CN101792425A CN 101792425 A CN101792425 A CN 101792425A CN 201010152904 CN201010152904 CN 201010152904 CN 201010152904 A CN201010152904 A CN 201010152904A CN 101792425 A CN101792425 A CN 101792425A
- Authority
- CN
- China
- Prior art keywords
- synthetic method
- product
- reaction
- tetrahydrofurfuryl
- diethyl carbonate
- 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.)
- Granted
Links
- VUFKMYLDDDNUJS-UHFFFAOYSA-N 2-(ethoxymethyl)oxolane Chemical compound CCOCC1CCCO1 VUFKMYLDDDNUJS-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000001308 synthesis method Methods 0.000 title abstract 3
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 claims abstract description 23
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 claims abstract description 23
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001447 alkali salts Chemical class 0.000 claims abstract description 15
- 239000003513 alkali Substances 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 238000010189 synthetic method Methods 0.000 claims description 23
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 235000015320 potassium carbonate Nutrition 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 159000000011 group IA salts Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 37
- 238000004458 analytical method Methods 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 14
- 230000005311 nuclear magnetism Effects 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical group [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 238000013019 agitation Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000009834 vaporization Methods 0.000 description 7
- 230000008016 vaporization Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- -1 sodium alkoxide Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000006959 Williamson synthesis reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Images
Landscapes
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of tetrahydrofurfuryl ethyl ether, which comprises the following steps that: tetrahydrofurfuryl alcohol, diethyl carbonate and alkali or alkaline salt are mixed and react to generate the tetrahydrofurfuryl ethyl ether. The molar ratio of the tetrahydrofurfuryl alcohol to the diethyl carbonate to the alkali is 1: (0.5 to 2): (1 to 4). The synthesis method of the tetrahydrofurfuryl ethyl ether of the invention is safe and has low cost and little pollution.
Description
Technical field
The present invention relates to the synthetic method of ethyl tetrahydrofurfuryl ether.
Background technology
The structure of ethyl tetrahydrofurfuryl ether is a unsymmetrical structure, and classical asymmetrical ether synthesis mode is the Williamson synthesis method, adopts halohydrocarbon and the ether of sodium alkoxide by the synthetic different alkyl of substitution reaction.Mostly this reaction is to adopt anhydrous system, utilizes sodium Metal 99.5 or sodium hydride that alcohol is converted into sodium alkoxide earlier, more corresponding haloalkane is joined in the reaction system, and reaction conditions requires harsh relatively, and operation is relatively more dangerous.The sodium Metal 99.5 that industrial a large amount of use is valuable or sodium hydride and organic solvent, dangerous big, cost is very high, and can cause the serious environmental pollution and endanger the operator healthy.
Summary of the invention
The purpose of this invention is to provide a kind of safety, cost is low, pollutes the synthetic method of little ethyl tetrahydrofurfuryl ether.
The synthetic method of ethyl tetrahydrofurfuryl ether provided by the present invention comprises the steps: that tetrahydrofurfuryl alcohol, diethyl carbonate and alkali or basic salt mix, and reaction generates ethyl tetrahydrofurfuryl ether.
The synthetic method of ethyl tetrahydrofurfuryl ether of the present invention, wherein: the mol ratio of described tetrahydrofurfuryl alcohol, described diethyl carbonate and described alkali or basic salt is 1: (0.5～2): (1～4).
The synthetic method of ethyl tetrahydrofurfuryl ether of the present invention, wherein: the mol ratio of described tetrahydrofurfuryl alcohol, described diethyl carbonate and described alkali or basic salt is 1: (0.5～2): (1～2).
The synthetic method of ethyl tetrahydrofurfuryl ether of the present invention, wherein: described temperature of reaction is 0～100 ℃.
The synthetic method of ethyl tetrahydrofurfuryl ether of the present invention, wherein: described temperature of reaction is 5～95 ℃.
The synthetic method of ethyl tetrahydrofurfuryl ether of the present invention, wherein: described alkali is sodium hydroxide or potassium hydroxide.
The synthetic method of ethyl tetrahydrofurfuryl ether of the present invention, wherein: described basic salt is salt of wormwood or yellow soda ash.
The synthetic method of ethyl tetrahydrofurfuryl ether of the present invention, wherein: the described reaction times is 0.5～10 hour.
The synthetic method of ethyl tetrahydrofurfuryl ether of the present invention, wherein: the described reaction times is 4～9 hours.
The synthetic method of ethyl tetrahydrofurfuryl ether of the present invention adopts tetrahydrofurfuryl alcohol, diethyl carbonate to react under alkaline environment, can high yield synthesize ethyl tetrahydrofurfuryl ether.The synthetic method raw material of ethyl tetrahydrofurfuryl ether of the present invention is poisoned less, has saved the step of preparation sodium alkoxide, has eliminated the Hazard Factor of producing, and has reduced disposal of pollutants in the production process, and has effectively reduced production cost.
Description of drawings
Fig. 1 is the nuclear magnetic spectrogram of product.
Fig. 2 is the infrared spectrum of product structure.
Embodiment
Embodiment 1, synthetic ethyl tetrahydrofurfuryl ether
In the 500ML reactor, add 102g tetrahydrofurfuryl alcohol, 0.5mol diethyl carbonate and 1mol potassium hydroxide, under agitation react, control reaction temperature is 5 ℃, reacts after 9 hours, finishes reaction, the air distillation reaction product is collected 150 ℃ of-160 ℃ of cuts, obtains product 98g.
Adopt Bruker AVANCE DRX 400MHz nuclear magnetic resonance spectrometer to measure product, solvent is a deuterochloroform; Its nuclear magnetic spectrogram and resonance peak belong to as table 1 and shown in Figure 1:
Table 1.ETE's
1H-NMR resonance peak ownership
The structure of product is analyzed by Nicolet 20DXB FT-IR type infrared chromatograph, and the composition of reaction product and purity check adopt the analysis of Tianjin, island GC-14A type gas chromatograph.Chromatographic column: 30m * 0.32mm PEG-20M capillary column; Column temperature: 40 ℃/3 minutes to 100 ℃/7 minutes; Temperature rise rate: 20 ℃/minute; Temperature of vaporization chamber: 250 ℃; Splitting ratio: 5: 1.
Infrared spectrum as shown in Figure 2.
Nuclear-magnetism and infrared analysis prove that product is an ethyl tetrahydrofurfuryl ether, and structural formula is
Gas-chromatography is analyzed, product purity 95%; In tetrahydrofurfuryl alcohol ethyl tetrahydrofurfuryl ether yield is 72%.
Embodiment 2, synthetic ethyl tetrahydrofurfuryl ether
In the 500ML reactor, add 102g tetrahydrofurfuryl alcohol, 0.6mol diethyl carbonate and 1mol sodium hydroxide, under agitation react, control reaction temperature is 5 ℃, reacts after 9 hours, finishes reaction, the air distillation reaction product is collected 150 ℃ of-160 ℃ of cuts, obtains product 96g.
Adopt Bruker AVANCE DRX 400MHz nuclear magnetic resonance spectrometer to measure product, solvent is a deuterochloroform; Its nuclear-magnetism spectrum resonance peak belongs to as table 2:
Table 2.ETE's
1H-NMR resonance peak ownership
The structure of product is analyzed by Nicolet 20DXB FT-IR type infrared chromatograph, and the composition of reaction product and purity check adopt the analysis of Tianjin, island GC-14A type gas chromatograph.Chromatographic column: 30m * 0.32mm PEG-20M capillary column; Column temperature: 40 ℃/3 minutes to 100 ℃/7 minutes; Temperature rise rate: 20 ℃/minute; Temperature of vaporization chamber: 250 ℃; Splitting ratio: 5: 1.
Infrared spectrum is not shown.
Nuclear-magnetism and infrared analysis prove that product is an ethyl tetrahydrofurfuryl ether, and structural formula is
Gas-chromatography is analyzed, product purity 95%; In tetrahydrofurfuryl alcohol ethyl tetrahydrofurfuryl ether yield is 70%.
Embodiment 3, synthetic ethyl tetrahydrofurfuryl ether
In the 500ML reactor, add 102g tetrahydrofurfuryl alcohol, 0.6mol diethyl carbonate and 1mol yellow soda ash, under agitation react, control reaction temperature is 5 ℃, reacts after 9 hours, finishes reaction, the air distillation reaction product is collected 150 ℃ of-160 ℃ of cuts, obtains product 103g.
Adopt Bruker AVANCE DRX 400MHz nuclear magnetic resonance spectrometer to measure product, solvent is a deuterochloroform; Its nuclear-magnetism spectrum resonance peak ownership is as shown in table 3:
Table 3.ETE's
1H-NMR resonance peak ownership
The structure of product is analyzed by Nicolet 20DXB FT-IR type infrared chromatograph, and the composition of reaction product and purity check adopt the analysis of Tianjin, island GC-14A type gas chromatograph.Chromatographic column: 30m * 0.32mm PEG-20M capillary column; Column temperature: 40 ℃/3 minutes to 100 ℃/7 minutes; Temperature rise rate: 20 ℃/minute; Temperature of vaporization chamber: 250 ℃; Splitting ratio: 5: 1.
Infrared spectrum is not shown.
Nuclear-magnetism and infrared analysis prove that product is an ethyl tetrahydrofurfuryl ether, and structural formula is
Gas-chromatography is analyzed, product purity 95%; In tetrahydrofurfuryl alcohol ethyl tetrahydrofurfuryl ether yield is 75%.
Embodiment 4, synthetic ethyl tetrahydrofurfuryl ether
In the 500ML reactor, add 102g tetrahydrofurfuryl alcohol, 0.6mol diethyl carbonate and 1mol salt of wormwood, under agitation react, control reaction temperature is 5 ℃, reacts after 9 hours, finishes reaction, the air distillation reaction product is collected 150 ℃ of-160 ℃ of cuts, obtains product 107g.
Adopt Bruker AVANCE DRX 400MHz nuclear magnetic resonance spectrometer to measure product, solvent is a deuterochloroform; Its nuclear-magnetism spectrum resonance peak ownership is as shown in table 4:
Table 4.ETE's
1H-NMR resonance peak ownership
The structure of product is analyzed by Nicolet 20DXB FT-IR type infrared chromatograph, and the composition of reaction product and purity check adopt the analysis of Tianjin, island GC-14A type gas chromatograph.Chromatographic column: 30m * 0.32mm PEG-20M capillary column; Column temperature: 40 ℃/3 minutes to 100 ℃/7 minutes; Temperature rise rate: 20 ℃/minute; Temperature of vaporization chamber: 250 ℃; Splitting ratio: 5: 1.
Infrared spectrum is not shown.
Nuclear-magnetism and infrared analysis prove that product is an ethyl tetrahydrofurfuryl ether, and structural formula is
Gas-chromatography is analyzed, product purity 95%; In tetrahydrofurfuryl alcohol ethyl tetrahydrofurfuryl ether yield is 78%.
Embodiment 5, synthetic ethyl tetrahydrofurfuryl ether
In the 500ML reactor, add 102g tetrahydrofurfuryl alcohol, 0.9mol diethyl carbonate and 1.8mol salt of wormwood, under agitation react, control reaction temperature is 50 ℃, reacts after 9 hours, finishes reaction, the air distillation reaction product is collected 150 ℃ of-160 ℃ of cuts, obtains product 130g.
Adopt Bruker AVANCE DRX 400MHz nuclear magnetic resonance spectrometer to measure product, solvent is a deuterochloroform; Its nuclear magnetic resonance peak ownership is as shown in table 5:
Table 5.ETE's
1H-NMR resonance peak ownership
The structure of product is analyzed by Nicolet 20DXB FT-IR type infrared chromatograph, and the composition of reaction product and purity check adopt the analysis of Tianjin, island GC-14A type gas chromatograph.Chromatographic column: 30m * 0.32mm PEG-20M capillary column; Column temperature: 40 ℃/3 minutes to 100 ℃/7 minutes; Temperature rise rate: 20 ℃/minute; Temperature of vaporization chamber: 250 ℃; Splitting ratio: 5: 1.
Infrared spectrum is not shown.
Nuclear-magnetism and infrared analysis prove that product is an ethyl tetrahydrofurfuryl ether, and structural formula is
Gas-chromatography is analyzed, product purity 95%; In tetrahydrofurfuryl alcohol ethyl tetrahydrofurfuryl ether yield is 95%.
Embodiment 6, synthetic ethyl tetrahydrofurfuryl ether
In the 500ML reactor, add 102g tetrahydrofurfuryl alcohol, 1.2mol diethyl carbonate and 2mol salt of wormwood, under agitation react, control reaction temperature is 50 ℃, reacts after 9 hours, finishes reaction, the air distillation reaction product is collected 150 ℃ of-160 ℃ of cuts, obtains product 132g.
Adopt Bruker AVANCE DRX 400MHz nuclear magnetic resonance spectrometer to measure product, solvent is a deuterochloroform; Its nuclear-magnetism spectrum resonance peak ownership is as shown in table 6:
Table 6.ETE's
1H-NMR resonance peak ownership
The structure of product is analyzed by Nicolet 20DXB FT-IR type infrared chromatograph, and the composition of reaction product and purity check adopt the analysis of Tianjin, island GC-14A type gas chromatograph.Chromatographic column: 30m * 0.32mm PEG-20M capillary column; Column temperature: 40 ℃/3 minutes to 100 ℃/7 minutes; Temperature rise rate: 20 ℃/minute; Temperature of vaporization chamber: 250 ℃; Splitting ratio: 5: 1.
Infrared spectrum is not shown.
Nuclear-magnetism and infrared analysis prove that product is an ethyl tetrahydrofurfuryl ether, and structural formula is
Gas-chromatography is analyzed, product purity 95%; In tetrahydrofurfuryl alcohol ethyl tetrahydrofurfuryl ether yield is 96%.
Embodiment 7, synthetic ethyl tetrahydrofurfuryl ether
In the 500ML reactor, add 102g tetrahydrofurfuryl alcohol, 2mol diethyl carbonate and 2mol salt of wormwood, under agitation react, control reaction temperature is 95 ℃, reacts after 4 hours, finishes reaction, the air distillation reaction product is collected 150 ℃ of-160 ℃ of cuts, obtains product 125g.
Adopt Bruker AVANCE DRX 400MHz nuclear magnetic resonance spectrometer to measure product, solvent is a deuterochloroform; Its nuclear magnetic resonance peak ownership is as shown in table 7:
Table 7.ETE's
1H-NMR resonance peak ownership
The structure of product is analyzed by Nicolet 20DXB FT-IR type infrared chromatograph, and the composition of reaction product and purity check adopt the analysis of Tianjin, island GC-14A type gas chromatograph.Chromatographic column: 30m * 0.32mm PEG-20M capillary column; Column temperature: 40 ℃/3 minutes to 100 ℃/7 minutes; Temperature rise rate: 20 ℃/minute; Temperature of vaporization chamber: 250 ℃; Splitting ratio: 5: 1.
Infrared spectrum is not shown.
Nuclear-magnetism and infrared analysis prove that product is an ethyl tetrahydrofurfuryl ether, and structural formula is
Gas-chromatography is analyzed, product purity 95%; In tetrahydrofurfuryl alcohol ethyl tetrahydrofurfuryl ether yield is 92%.
Above embodiment is described preferred implementation of the present invention; be not that scope of the present invention is limited; design under the prerequisite of spirit not breaking away from the present invention; various distortion and improvement that the common engineering technical personnel in this area make technical scheme of the present invention all should fall in the definite protection domain of claims of the present invention.
Claims (9)
1. the synthetic method of ethyl tetrahydrofurfuryl ether comprises the steps: that tetrahydrofurfuryl alcohol, diethyl carbonate and alkali or basic salt mix, and reaction generates ethyl tetrahydrofurfuryl ether.
2. synthetic method according to claim 1 is characterized in that: the mol ratio of described tetrahydrofurfuryl alcohol, described diethyl carbonate and described alkali or basic salt is 1: (0.5～2): (1～4).
3. synthetic method according to claim 2 is characterized in that: the mol ratio of described tetrahydrofurfuryl alcohol, described diethyl carbonate and described alkali or basic salt is 1: (0.5～2): (1～2).
4. according to arbitrary described synthetic method in the claim 1 to 3, it is characterized in that: described temperature of reaction is 0～100 ℃.
5. synthetic method according to claim 4 is characterized in that: described temperature of reaction is 5～95 ℃.
6. according to arbitrary described synthetic method in the claim 1 to 3, it is characterized in that: described alkali is sodium hydroxide or potassium hydroxide.
7. according to arbitrary described synthetic method in the claim 1 to 3, it is characterized in that: described basic salt is salt of wormwood or yellow soda ash.
8. according to arbitrary described synthetic method in the claim 1 to 3, it is characterized in that: the described reaction times is 0.5～10 hour.
9. synthetic method according to claim 8 is characterized in that: the described reaction times is 4～9 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010101529048A CN101792425B (en) | 2010-04-22 | 2010-04-22 | Synthesis method of tetrahydrofurfuryl ethyl ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010101529048A CN101792425B (en) | 2010-04-22 | 2010-04-22 | Synthesis method of tetrahydrofurfuryl ethyl ether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101792425A true CN101792425A (en) | 2010-08-04 |
| CN101792425B CN101792425B (en) | 2012-08-01 |
Family
ID=42585366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010101529048A Expired - Fee Related CN101792425B (en) | 2010-04-22 | 2010-04-22 | Synthesis method of tetrahydrofurfuryl ethyl ether |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101792425B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106928165A (en) * | 2015-12-30 | 2017-07-07 | 中国石油化工股份有限公司 | A kind of preparation method of tetrahydrofurfuryl ether compound |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4305878A (en) * | 1981-01-15 | 1981-12-15 | Allied Corporation | Purifying ethyl tetrahydrofurfuryl ether by aqueous salt extraction |
| JPS599861A (en) * | 1982-07-09 | 1984-01-19 | Nisso Yuka Kogyo Kk | Electrolyte solvent and battery constituted by its use |
-
2010
- 2010-04-22 CN CN2010101529048A patent/CN101792425B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4305878A (en) * | 1981-01-15 | 1981-12-15 | Allied Corporation | Purifying ethyl tetrahydrofurfuryl ether by aqueous salt extraction |
| JPS599861A (en) * | 1982-07-09 | 1984-01-19 | Nisso Yuka Kogyo Kk | Electrolyte solvent and battery constituted by its use |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106928165A (en) * | 2015-12-30 | 2017-07-07 | 中国石油化工股份有限公司 | A kind of preparation method of tetrahydrofurfuryl ether compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101792425B (en) | 2012-08-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101456855B (en) | Method for preparing 1,3-propanesultone | |
| CN105693470B (en) | A kind of method of the alcohol of 3 methyl of continuous production, 3 butylene 1 | |
| CN102875327B (en) | A kind of technique for preparing absolute ethanol from nearly azeotropic concentration ethanol-water mixture | |
| CN101602770B (en) | Method for preparing herbicide | |
| CN101792426A (en) | Synthesis method of tetrahydrofurfuryl ethyl ether | |
| CN102731269B (en) | Synthesis method of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol | |
| CN100554231C (en) | The method for preparing butyl glycol ether | |
| CN101792425B (en) | Synthesis method of tetrahydrofurfuryl ethyl ether | |
| CN113651837B (en) | Preparation method of 3, 3-trifluoropropanol | |
| CN101805315B (en) | Synthesis method of ethyl tetrahydrofurfuryl ether | |
| CN103289073A (en) | Preparation method of polycarboxylate water-reducing agent macromonomer methylallyl alcohol polyethenoxy ether | |
| CN105439850A (en) | Method for synthesizing triethylene glycol di-2-ethylhexoate | |
| CN101805314B (en) | Synthesis method of ethyl tetrahydrofurfuryl ether | |
| CN103896975B (en) | A kind of synthetic method of 3-cyclic ethers methyl trifluoro potassium borate | |
| CN113968894B (en) | A method for preparing cycloastragenol by degradation of astragaloside IV | |
| CN1548427A (en) | Prepn process and apparatus for alpha-acetyl-gamma-butyrolactone | |
| CN104277027A (en) | Preparation method of (R)-propylene carbonate | |
| CN111995641B (en) | Production method of alkyl phosphine | |
| CN109232350A (en) | A method of preparing N-Boc-3- pyrrolidine formaldehyde | |
| CN102432465B (en) | Method for preparing methyl methacrylate | |
| CN108358783A (en) | 3-substituted glutaric acid diester and preparation method of glutaconic acid diester | |
| CN105037113A (en) | Synthesis method of carbonic acid ortho-ester | |
| CN111333571A (en) | Method for synthesizing vitamin B6 triisopalmitate | |
| CN104120039A (en) | Method for preparing fatty acid methyl ester through multi-stage ester exchange | |
| CN115636723B (en) | Preparation method of trifluoroethanol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| ASS | Succession or assignment of patent right |
Owner name: XINJIANG KEYUAN CHEMICAL CO., LTD. Free format text: FORMER OWNER: YU RONG Effective date: 20110919 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 833200 KARAMAY, XINJIANG UYGUR AUTONOMOUS REGION TO: 833200 KASHGAR, XINJIANG UYGUR AUTONOMOUS REGION |
|
| TA01 | Transfer of patent application right |
Effective date of registration: 20110919 Address after: 833200 No. 80-1 East Kashi Road, the Xinjiang Uygur Autonomous Region, Kuitun Applicant after: Xinjiang Keyuan Chemical Co., Ltd. Address before: 833200 the Xinjiang Uygur Autonomous Region Karamay Dushanzi 11 District 38 Building No. 10 Lai city Applicant before: Yu Rong |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20120801 Termination date: 20190422 |