SG185059A1 - Method for producing alkylene carbonate and/or alkylene glycol - Google Patents
Method for producing alkylene carbonate and/or alkylene glycol Download PDFInfo
- Publication number
- SG185059A1 SG185059A1 SG2012079554A SG2012079554A SG185059A1 SG 185059 A1 SG185059 A1 SG 185059A1 SG 2012079554 A SG2012079554 A SG 2012079554A SG 2012079554 A SG2012079554 A SG 2012079554A SG 185059 A1 SG185059 A1 SG 185059A1
- Authority
- SG
- Singapore
- Prior art keywords
- catalyst
- reaction
- liquid
- alkali metal
- carbonate
- Prior art date
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 144
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- -1 alkylene carbonate Chemical compound 0.000 title claims description 84
- 239000003054 catalyst Substances 0.000 claims abstract description 156
- 238000006243 chemical reaction Methods 0.000 claims abstract description 100
- 238000000034 method Methods 0.000 claims abstract description 79
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 71
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 37
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000006460 hydrolysis reaction Methods 0.000 claims description 114
- 239000007788 liquid Substances 0.000 claims description 107
- 230000007062 hydrolysis Effects 0.000 claims description 91
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 68
- 238000009833 condensation Methods 0.000 claims description 40
- 230000005494 condensation Effects 0.000 claims description 40
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 39
- 239000001569 carbon dioxide Substances 0.000 claims description 34
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 34
- 238000004821 distillation Methods 0.000 claims description 31
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 26
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- 238000000926 separation method Methods 0.000 claims description 23
- 150000004045 organic chlorine compounds Chemical class 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 238000007599 discharging Methods 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 11
- 150000001340 alkali metals Chemical class 0.000 abstract description 11
- 239000002244 precipitate Substances 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract description 3
- 150000002500 ions Chemical class 0.000 abstract description 3
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 abstract 1
- 239000010445 mica Substances 0.000 abstract 1
- 229910052618 mica group Inorganic materials 0.000 abstract 1
- 229960004424 carbon dioxide Drugs 0.000 description 31
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 14
- 239000007789 gas Substances 0.000 description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 9
- 238000009835 boiling Methods 0.000 description 7
- 230000018044 dehydration Effects 0.000 description 7
- 238000006297 dehydration reaction Methods 0.000 description 7
- 239000001103 potassium chloride Substances 0.000 description 7
- 235000011164 potassium chloride Nutrition 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- RLZMYANQLOCZOB-UHFFFAOYSA-M tributyl(methyl)phosphanium;iodide Chemical compound [I-].CCCC[P+](C)(CCCC)CCCC RLZMYANQLOCZOB-UHFFFAOYSA-M 0.000 description 4
- 238000000605 extraction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- IKZOMJGRWIOEDP-UHFFFAOYSA-N 2-(chloromethyl)-1,3-dioxolane Chemical compound ClCC1OCCO1 IKZOMJGRWIOEDP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000009616 inductively coupled plasma Methods 0.000 description 2
- 229910001503 inorganic bromide Inorganic materials 0.000 description 2
- 229910001505 inorganic iodide Inorganic materials 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 125000005496 phosphonium group Chemical group 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- VCEVTCDKSHGBSX-UHFFFAOYSA-N 3,3,3-triphenylpropylphosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)(CC[PH3+])C1=CC=CC=C1 VCEVTCDKSHGBSX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- NYQDCVLCJXRDSK-UHFFFAOYSA-N Bromofos Chemical compound COP(=S)(OC)OC1=CC(Cl)=C(Br)C=C1Cl NYQDCVLCJXRDSK-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002247 constant time method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000003498 tellurium compounds Chemical class 0.000 description 1
- IZYFBZDLXRHRLF-UHFFFAOYSA-N tritylphosphane;hydroiodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 IZYFBZDLXRHRLF-UHFFFAOYSA-N 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
- C07C29/10—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
- C07C29/103—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 of cyclic ethers
- C07C29/106—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 of cyclic ethers of oxiranes
-
- 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
- C07C29/12—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 mineral acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010103785 | 2010-04-28 | ||
| JP2010158779 | 2010-07-13 | ||
| PCT/JP2011/059855 WO2011136127A1 (ja) | 2010-04-28 | 2011-04-21 | アルキレンカーボネート及び／又はアルキレングリコールの製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG185059A1 true SG185059A1 (en) | 2012-12-28 |
Family
ID=44861433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2012079554A SG185059A1 (en) | 2010-04-28 | 2011-04-21 | Method for producing alkylene carbonate and/or alkylene glycol |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JP5725019B2 (ko) |
| KR (2) | KR101663347B1 (ko) |
| CN (1) | CN102858727B (ko) |
| BR (1) | BR112012027617B1 (ko) |
| SG (1) | SG185059A1 (ko) |
| TW (1) | TWI511947B (ko) |
| WO (1) | WO2011136127A1 (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20220024841A1 (en) * | 2018-12-10 | 2022-01-27 | Shell Oil Company | Process for the preparation of ethylene glycol |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5902985B2 (ja) * | 2012-03-30 | 2016-04-13 | 株式会社日本触媒 | エチレングリコール類の製造方法 |
| JP2014148481A (ja) * | 2013-02-01 | 2014-08-21 | Mitsubishi Chemicals Corp | アルキレンカーボネートの製造方法 |
| CN109867654B (zh) * | 2019-02-19 | 2021-06-29 | 胜华新能源科技(东营)有限公司 | 一种用于环氧烷烃和二氧化碳制备碳酸亚烷基酯的方法 |
| KR102150240B1 (ko) * | 2019-10-14 | 2020-09-01 | 그린케미칼 주식회사 | 알킬렌카보네이트 제조 장치 및 그를 이용한 제조 방법 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5690029A (en) * | 1979-12-24 | 1981-07-21 | Nippon Shokubai Kagaku Kogyo Co Ltd | Preparation of high-purity alkylene glycol |
| SG74047A1 (en) * | 1997-04-30 | 2000-07-18 | Mitsubishi Chem Corp | Process for producing alkylene glycol |
| JP3690129B2 (ja) * | 1998-08-10 | 2005-08-31 | 三菱化学株式会社 | アルキレングリコールの製造方法 |
| JP3921847B2 (ja) * | 1998-11-13 | 2007-05-30 | 三菱化学株式会社 | エチレングリコールの製造方法 |
| JP3921843B2 (ja) * | 1998-10-27 | 2007-05-30 | 三菱化学株式会社 | エチレングリコールの製造方法 |
| JP3750376B2 (ja) * | 1998-11-06 | 2006-03-01 | 三菱化学株式会社 | エチレングリコールの製造方法 |
| JP2001031600A (ja) * | 1999-07-14 | 2001-02-06 | Nippon Shokubai Co Ltd | 高純度モノエチレングリコールの製法 |
| JP2001031601A (ja) * | 1999-07-14 | 2001-02-06 | Nippon Shokubai Co Ltd | 高純度モノエチレングリコールの製造方法 |
| US6437199B1 (en) * | 1999-07-14 | 2002-08-20 | Nippon Shokubai Co., Ltd. | Method for production of high-purity monoethylene glycol |
| WO2004069777A1 (ja) * | 2003-02-07 | 2004-08-19 | Mitsubishi Chemical Corporation | アルキレン誘導体の製造方法及びアルキレン誘導体製造用触媒の再生方法 |
| JP4273802B2 (ja) | 2003-03-27 | 2009-06-03 | 三菱化学株式会社 | アルキレン誘導体の製造方法 |
| JP4333153B2 (ja) * | 2003-02-07 | 2009-09-16 | 三菱化学株式会社 | アルキレングリコールの製造方法 |
| PE20070478A1 (es) * | 2005-08-02 | 2007-05-18 | Shell Int Research | Proceso de preparacion de alquilenglicoles |
-
2011
- 2011-04-21 CN CN201180021036.2A patent/CN102858727B/zh active Active
- 2011-04-21 KR KR1020127030331A patent/KR101663347B1/ko active IP Right Grant
- 2011-04-21 JP JP2012512808A patent/JP5725019B2/ja active Active
- 2011-04-21 WO PCT/JP2011/059855 patent/WO2011136127A1/ja active Application Filing
- 2011-04-21 KR KR1020167008016A patent/KR101671155B1/ko active IP Right Grant
- 2011-04-21 SG SG2012079554A patent/SG185059A1/en unknown
- 2011-04-21 BR BR112012027617-4A patent/BR112012027617B1/pt active IP Right Grant
- 2011-04-27 TW TW100114639A patent/TWI511947B/zh active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20220024841A1 (en) * | 2018-12-10 | 2022-01-27 | Shell Oil Company | Process for the preparation of ethylene glycol |
| US11807594B2 (en) * | 2018-12-10 | 2023-11-07 | Shell Usa, Inc. | Process for the preparation of ethylene glycol |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102858727A (zh) | 2013-01-02 |
| KR20130056242A (ko) | 2013-05-29 |
| KR20160039307A (ko) | 2016-04-08 |
| JP5725019B2 (ja) | 2015-05-27 |
| BR112012027617A2 (pt) | 2016-08-09 |
| CN102858727B (zh) | 2014-09-24 |
| WO2011136127A1 (ja) | 2011-11-03 |
| KR101671155B1 (ko) | 2016-10-31 |
| KR101663347B1 (ko) | 2016-10-06 |
| BR112012027617B1 (pt) | 2021-11-09 |
| TWI511947B (zh) | 2015-12-11 |
| JPWO2011136127A1 (ja) | 2013-07-18 |
| TW201141820A (en) | 2011-12-01 |
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