DE2855231C3 - Kontinuierliches Verfahren zur Herstellung von Glykolen - Google Patents
Kontinuierliches Verfahren zur Herstellung von GlykolenInfo
- Publication number
- DE2855231C3 DE2855231C3 DE2855231A DE2855231A DE2855231C3 DE 2855231 C3 DE2855231 C3 DE 2855231C3 DE 2855231 A DE2855231 A DE 2855231A DE 2855231 A DE2855231 A DE 2855231A DE 2855231 C3 DE2855231 C3 DE 2855231C3
- Authority
- DE
- Germany
- Prior art keywords
- line
- glycol
- stream
- water
- reactor
- 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
- 238000010924 continuous production Methods 0.000 title claims description 14
- 150000002334 glycols Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 42
- 230000007062 hydrolysis Effects 0.000 claims description 41
- -1 alkylene carboxylates Chemical class 0.000 claims description 35
- 238000002360 preparation method Methods 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 131
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 94
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
- 238000000034 method Methods 0.000 description 53
- 230000008569 process Effects 0.000 description 53
- 239000003054 catalyst Substances 0.000 description 51
- 229910002092 carbon dioxide Inorganic materials 0.000 description 47
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 41
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 35
- 239000001569 carbon dioxide Substances 0.000 description 34
- 239000000047 product Substances 0.000 description 21
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 description 18
- 235000011181 potassium carbonates Nutrition 0.000 description 18
- 150000001299 aldehydes Chemical class 0.000 description 16
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 16
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- 238000004064 recycling Methods 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 238000003763 carbonization Methods 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000011010 flushing procedure Methods 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- 230000000153 supplemental effect Effects 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000003944 halohydrins Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000006200 vaporizer Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910018054 Ni-Cu Inorganic materials 0.000 description 1
- 229910018481 Ni—Cu Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- NBZANZVJRKXVBH-GYDPHNCVSA-N alpha-Cryptoxanthin Natural products O[C@H]1CC(C)(C)C(/C=C/C(=C\C=C\C(=C/C=C/C=C(\C=C\C=C(/C=C/[C@H]2C(C)=CCCC2(C)C)\C)/C)\C)/C)=C(C)C1 NBZANZVJRKXVBH-GYDPHNCVSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000005588 carbonic acid salt group Chemical group 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- FIJPWGLOBMXXSF-UHFFFAOYSA-M potassium;2-hydroxyacetate Chemical compound [K+].OCC([O-])=O FIJPWGLOBMXXSF-UHFFFAOYSA-M 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 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
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
- C07C29/095—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 esters of organic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/863,352 US4117250A (en) | 1977-12-22 | 1977-12-22 | Continuous process for producing alkylene glycols from alkylene carbonates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2855231A1 DE2855231A1 (de) | 1979-06-28 |
| DE2855231B2 DE2855231B2 (de) | 1981-02-19 |
| DE2855231C3 true DE2855231C3 (de) | 1987-07-30 |
Family
ID=25340946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2855231A Expired DE2855231C3 (de) | 1977-12-22 | 1978-12-21 | Kontinuierliches Verfahren zur Herstellung von Glykolen |
Country Status (9)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1107301A (en) * | 1977-12-22 | 1981-08-18 | Union Carbide Corporation | Hydrolysis of alkylene carbonates to alkylene glycols |
| US4237324A (en) * | 1979-01-22 | 1980-12-02 | The Dow Chemical Company | Production of monoglycols from alkylene carbonates |
| CA1121389A (en) * | 1979-05-24 | 1982-04-06 | Hiroshi Odanaka | Process for the production of alkylene glycols |
| DE2931753C2 (de) * | 1979-08-04 | 1984-10-04 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur Herstellung von vicinalen Alkylenglykolen |
| US4400559A (en) * | 1982-06-14 | 1983-08-23 | The Halcon Sd Group, Inc. | Process for preparing ethylene glycol |
| US4508927A (en) * | 1983-08-02 | 1985-04-02 | The Halcon Sd Group, Inc. | Preparation of glycols from ethylene oxide |
| US4556748A (en) * | 1983-10-31 | 1985-12-03 | The Dow Chemical Company | Process for producing alkylene glycols |
| US4519875A (en) * | 1984-05-09 | 1985-05-28 | The Halcon Sd Group, Inc. | Purification of ethylene glycol derived from ethylene carbonate |
| JPH0249876U (US07902200-20110308-C00004.png) * | 1988-09-29 | 1990-04-06 | ||
| GB8827681D0 (en) * | 1988-11-25 | 1988-12-29 | Gaddis F | Bubble/water agitation device |
| US5013820A (en) * | 1989-04-12 | 1991-05-07 | Eastman Kodak Company | Preparation of poly(ethlene-2,6-naphthalene dicarboxylate) from dimethyl-2,6-naphthalene dicarboxylate and methyl hydrogen 2,6-naphthalene dicarboxylate |
| US5275734A (en) * | 1992-08-04 | 1994-01-04 | International Business Machines Corporation | Chemical pre-treatment and biological destruction of propylene carbonate waste streams effluent streams to reduce the biological oxygen demand thereof |
| CN1102863C (zh) * | 1998-05-28 | 2003-03-12 | 中国石油天然气股份有限公司抚顺石化分公司 | 环氧乙烷水合制备乙二醇的催化剂及过程 |
| US7405185B2 (en) * | 2003-09-26 | 2008-07-29 | Chevron Oronite Company Llc | Process for making Group II metal overbased sulfurized alkylphenols |
| CN100354244C (zh) * | 2004-07-28 | 2007-12-12 | 华东理工大学 | C2～c3的二元醇的制备方法 |
| US7462748B2 (en) * | 2006-09-07 | 2008-12-09 | Shell Oil Company | Process for the preparation of alkylene glycol |
| US7465840B2 (en) * | 2006-09-07 | 2008-12-16 | Shell Oil Company | Process for the preparation of alkylene glycol |
| DE102009038398A1 (de) | 2009-08-24 | 2011-03-03 | Uhde Gmbh | Verfahren und Vorrichtung zur Herstellung von Alkylenoxiden und von Alkylenglykolen |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1793247C3 (de) * | 1968-08-21 | 1973-11-29 | Wsesojusnij Nautschno-Issledowatel' Skij Institut Neftechimitscheskich Prozessow, Leningrad (Sowjetunion) | Verfahren zur Herstellung von Alkylenglykolen |
| GB1177877A (en) * | 1968-08-26 | 1970-01-14 | Vnii Neftekhim Protsessov | Process for the Production of Alkylene Glycols |
| US3629343A (en) * | 1968-10-11 | 1971-12-21 | Vnii Neftekhim Protsessov | Process for the production of alkylene glycols |
| CA1107301A (en) * | 1977-12-22 | 1981-08-18 | Union Carbide Corporation | Hydrolysis of alkylene carbonates to alkylene glycols |
-
1977
- 1977-12-22 US US05/863,352 patent/US4117250A/en not_active Expired - Lifetime
-
1978
- 1978-12-20 CA CA318,306A patent/CA1113123A/en not_active Expired
- 1978-12-21 FR FR7835920A patent/FR2412516A1/fr active Granted
- 1978-12-21 IT IT7831177A patent/IT1102413B/it active
- 1978-12-21 NL NL7812445A patent/NL7812445A/xx not_active Application Discontinuation
- 1978-12-21 BE BE192473A patent/BE872958A/xx not_active IP Right Cessation
- 1978-12-21 DE DE2855231A patent/DE2855231C3/de not_active Expired
- 1978-12-21 GB GB7849427A patent/GB2011400B/en not_active Expired
- 1978-12-21 JP JP53156944A patent/JPS5852970B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE872958A (fr) | 1979-06-21 |
| JPS5490107A (en) | 1979-07-17 |
| FR2412516B1 (US07902200-20110308-C00004.png) | 1984-05-25 |
| JPS5852970B2 (ja) | 1983-11-26 |
| DE2855231B2 (de) | 1981-02-19 |
| CA1113123A (en) | 1981-11-24 |
| IT1102413B (it) | 1985-10-07 |
| IT7831177A0 (it) | 1978-12-21 |
| GB2011400B (en) | 1982-05-19 |
| US4117250A (en) | 1978-09-26 |
| FR2412516A1 (fr) | 1979-07-20 |
| GB2011400A (en) | 1979-07-11 |
| DE2855231A1 (de) | 1979-06-28 |
| NL7812445A (nl) | 1979-06-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| 8263 | Opposition against grant of a patent | ||
| 8227 | New person/name/address of the applicant |
Free format text: UNION CARBIDE CORP., 06817 DANBURY, CONN., US |
|
| 8281 | Inventor (new situation) |
Free format text: FOSTER, ROBERT DEAN MALISZEWSKI, THOMAS ARTHUR, CHARLESTON, W.VA., US SIMS JUN., JOSEPH ALTON, ELKVIEW, W.VA., US TAYLOR, GLENN ALFRED, RIDGEWOOD, N.J., US |
|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |