JPS6217574B2 - - Google Patents
Info
- Publication number
- JPS6217574B2 JPS6217574B2 JP55006515A JP651580A JPS6217574B2 JP S6217574 B2 JPS6217574 B2 JP S6217574B2 JP 55006515 A JP55006515 A JP 55006515A JP 651580 A JP651580 A JP 651580A JP S6217574 B2 JPS6217574 B2 JP S6217574B2
- Authority
- JP
- Japan
- Prior art keywords
- ethylene glycol
- iron
- reaction
- distillation
- residue
- 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.)
- Expired
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 397
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 133
- 229910052742 iron Inorganic materials 0.000 claims description 67
- 238000006243 chemical reaction Methods 0.000 claims description 58
- 238000004821 distillation Methods 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 46
- 150000001336 alkenes Chemical group 0.000 claims description 40
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 37
- 239000011541 reaction mixture Substances 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 30
- 238000000746 purification Methods 0.000 claims description 28
- 150000005215 alkyl ethers Chemical group 0.000 claims description 23
- 239000003729 cation exchange resin Substances 0.000 claims description 21
- 239000002994 raw material Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 15
- 238000007670 refining Methods 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 239000012535 impurity Substances 0.000 claims description 7
- 230000008016 vaporization Effects 0.000 claims description 7
- 238000004064 recycling Methods 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 150000003509 tertiary alcohols Chemical class 0.000 description 18
- BDLXTDLGTWNUFM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]ethanol Chemical compound CC(C)(C)OCCO BDLXTDLGTWNUFM-UHFFFAOYSA-N 0.000 description 17
- 238000000354 decomposition reaction Methods 0.000 description 16
- 239000006227 byproduct Substances 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 11
- 229930195733 hydrocarbon Chemical group 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 230000002378 acidificating effect Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000001577 simple distillation Methods 0.000 description 10
- -1 Ethylene glycol monoalkyl ethers Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 8
- 239000004215 Carbon black (E152) Chemical group 0.000 description 8
- 238000000605 extraction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229940023913 cation exchange resins Drugs 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 238000000895 extractive distillation Methods 0.000 description 6
- KGRYJQHZLUAEES-UHFFFAOYSA-N 2-(2-methylbutan-2-yloxy)ethanol Chemical compound CCC(C)(C)OCCO KGRYJQHZLUAEES-UHFFFAOYSA-N 0.000 description 5
- 229910000975 Carbon steel Inorganic materials 0.000 description 5
- 239000010962 carbon steel Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000009834 vaporization Methods 0.000 description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- KWGJJEBPCVMBIG-UHFFFAOYSA-N 2-methyl-2-[2-[(2-methylpropan-2-yl)oxy]ethoxy]propane Chemical compound CC(C)(C)OCCOC(C)(C)C KWGJJEBPCVMBIG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004231 fluid catalytic cracking Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000013077 target material Substances 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- HUWFDQSAXOIUNP-UHFFFAOYSA-N 2-butan-2-yloxyethanol Chemical compound CCC(C)OCCO HUWFDQSAXOIUNP-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- ZQAGBLBJQZWEMH-UHFFFAOYSA-N 2-methyl-2-[2-(2-methylbutan-2-yloxy)ethoxy]butane Chemical compound CCC(C)(C)OCCOC(C)(C)CC ZQAGBLBJQZWEMH-UHFFFAOYSA-N 0.000 description 1
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- 101100170365 Arabidopsis thaliana At5g60805 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000004063 acid-resistant material Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 229940090012 bentyl Drugs 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 101150002475 mae1 gene Proteins 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP651580A JPS56103127A (en) | 1980-01-22 | 1980-01-22 | Preparation of ethylene glycol monotert-alkyl ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP651580A JPS56103127A (en) | 1980-01-22 | 1980-01-22 | Preparation of ethylene glycol monotert-alkyl ether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56103127A JPS56103127A (en) | 1981-08-18 |
| JPS6217574B2 true JPS6217574B2 (no) | 1987-04-18 |
Family
ID=11640534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP651580A Granted JPS56103127A (en) | 1980-01-22 | 1980-01-22 | Preparation of ethylene glycol monotert-alkyl ether |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56103127A (no) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1070165C (zh) * | 1998-03-30 | 2001-08-29 | 中国石油化工总公司 | 乙二醇单特丁基醚精制工艺 |
| WO2008037659A1 (de) * | 2006-09-28 | 2008-04-03 | Basf Se | Verfahren zur herstellung von 2,2'-aminoethoxyethanol in elektro-qualität |
| KR101331553B1 (ko) * | 2011-02-18 | 2013-11-20 | 대림산업 주식회사 | 글리콜에테르를 이용한 고순도 이소부텐의 제조 방법 |
| KR101331551B1 (ko) * | 2011-02-22 | 2013-11-20 | 대림산업 주식회사 | 글리콜 모노-터셔리-부틸에테르 화합물의 제조 방법 |
| CN106397137B (zh) * | 2015-07-27 | 2019-04-23 | 万华化学集团股份有限公司 | 一种制备二元醇单叔丁基醚的方法 |
| CN110759817B (zh) * | 2018-07-27 | 2022-10-14 | 中国石油化工股份有限公司 | 乙二醇单叔丁基醚的制备方法 |
-
1980
- 1980-01-22 JP JP651580A patent/JPS56103127A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56103127A (en) | 1981-08-18 |
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