JPH0446936B2 - - Google Patents
Info
- Publication number
- JPH0446936B2 JPH0446936B2 JP62022411A JP2241187A JPH0446936B2 JP H0446936 B2 JPH0446936 B2 JP H0446936B2 JP 62022411 A JP62022411 A JP 62022411A JP 2241187 A JP2241187 A JP 2241187A JP H0446936 B2 JPH0446936 B2 JP H0446936B2
- Authority
- JP
- Japan
- Prior art keywords
- glycerin
- ethylene glycol
- catalyst
- boiling point
- solvent
- 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 - Lifetime
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 111
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 97
- 235000011187 glycerol Nutrition 0.000 claims description 49
- 239000003054 catalyst Substances 0.000 claims description 32
- 238000009835 boiling Methods 0.000 claims description 29
- 239000012046 mixed solvent Substances 0.000 claims description 9
- 229920005862 polyol Polymers 0.000 claims description 9
- 150000003077 polyols Chemical class 0.000 claims description 9
- 150000003512 tertiary amines Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000010948 rhodium Substances 0.000 description 27
- 239000002904 solvent Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 238000004821 distillation Methods 0.000 description 9
- 229920000570 polyether Polymers 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 229910052703 rhodium Inorganic materials 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- -1 become metallized Substances 0.000 description 6
- 230000001186 cumulative effect Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 6
- BBYSGWAYRRMWOW-UHFFFAOYSA-N 1-hexylpiperidine Chemical compound CCCCCCN1CCCCC1 BBYSGWAYRRMWOW-UHFFFAOYSA-N 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- IQTWKCSNWONACC-UHFFFAOYSA-N 1-octylpyrrolidine Chemical compound CCCCCCCCN1CCCC1 IQTWKCSNWONACC-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- VMCIKMLQXFLKAX-UHFFFAOYSA-N 1-methoxy-2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethane Chemical compound COCCOCCOCCOCCOCCOCCOC VMCIKMLQXFLKAX-UHFFFAOYSA-N 0.000 description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-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
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- DMDPGPKXQDIQQG-UHFFFAOYSA-N pentaglyme Chemical compound COCCOCCOCCOCCOCCOC DMDPGPKXQDIQQG-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 2
- BFIAIMMAHAIVFT-UHFFFAOYSA-N 1-[bis(2-hydroxybutyl)amino]butan-2-ol Chemical compound CCC(O)CN(CC(O)CC)CC(O)CC BFIAIMMAHAIVFT-UHFFFAOYSA-N 0.000 description 1
- GUSTUIJJPMXTTI-UHFFFAOYSA-N 1-dodecylazepane Chemical compound CCCCCCCCCCCCN1CCCCCC1 GUSTUIJJPMXTTI-UHFFFAOYSA-N 0.000 description 1
- BHDDSIBLLZQKRF-UHFFFAOYSA-N 1-dodecylpiperidine Chemical compound CCCCCCCCCCCCN1CCCCC1 BHDDSIBLLZQKRF-UHFFFAOYSA-N 0.000 description 1
- JVCRHTKQAPRUKG-UHFFFAOYSA-N 1-dodecylpyrrolidine Chemical compound CCCCCCCCCCCCN1CCCC1 JVCRHTKQAPRUKG-UHFFFAOYSA-N 0.000 description 1
- OUKZCQQNMWXMNE-UHFFFAOYSA-N 1-hexylpyrrolidine Chemical compound CCCCCCN1CCCC1 OUKZCQQNMWXMNE-UHFFFAOYSA-N 0.000 description 1
- POIAJDOGVUDESO-UHFFFAOYSA-N 1-pentylazepane Chemical compound CCCCCN1CCCCCC1 POIAJDOGVUDESO-UHFFFAOYSA-N 0.000 description 1
- GTXIYTMABDZZGQ-UHFFFAOYSA-N 2-dodecyl-1h-pyrrole Chemical compound CCCCCCCCCCCCC1=CC=CN1 GTXIYTMABDZZGQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 150000005218 dimethyl ethers Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- CYQYCASVINMDFD-UHFFFAOYSA-N n,n-ditert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)N(C(C)(C)C)C(C)(C)C CYQYCASVINMDFD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 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
- Catalysts (AREA)
- 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 |
|---|---|---|---|
| JP62022411A JPS63190838A (ja) | 1987-02-04 | 1987-02-04 | エチレングリコ−ルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62022411A JPS63190838A (ja) | 1987-02-04 | 1987-02-04 | エチレングリコ−ルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63190838A JPS63190838A (ja) | 1988-08-08 |
| JPH0446936B2 true JPH0446936B2 (en]) | 1992-07-31 |
Family
ID=12081923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62022411A Granted JPS63190838A (ja) | 1987-02-04 | 1987-02-04 | エチレングリコ−ルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63190838A (en]) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS646226A (en) * | 1987-06-26 | 1989-01-10 | Agency Ind Science Techn | Production of ethylene glycol and glycerin |
| US5218802A (en) * | 1990-01-16 | 1993-06-15 | Shimizu Construction Co., Ltd. | Column and beam connecting assembly |
| JP2645365B2 (ja) * | 1990-02-22 | 1997-08-25 | 清水建設株式会社 | 柱梁接合部 |
| JP4736305B2 (ja) * | 2001-03-30 | 2011-07-27 | ダイキン工業株式会社 | 換気装置および換気装置の製造方法 |
-
1987
- 1987-02-04 JP JP62022411A patent/JPS63190838A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63190838A (ja) | 1988-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |