KR100286571B1 - 반응증류를 이용한 글리콜 에스테르의 제조방법 - Google Patents
반응증류를 이용한 글리콜 에스테르의 제조방법 Download PDFInfo
- Publication number
- KR100286571B1 KR100286571B1 KR1019990008051A KR19990008051A KR100286571B1 KR 100286571 B1 KR100286571 B1 KR 100286571B1 KR 1019990008051 A KR1019990008051 A KR 1019990008051A KR 19990008051 A KR19990008051 A KR 19990008051A KR 100286571 B1 KR100286571 B1 KR 100286571B1
- Authority
- KR
- South Korea
- Prior art keywords
- glycol
- reaction
- distillation column
- carboxylic acid
- glycol ether
- Prior art date
Links
- -1 glycol ester Chemical class 0.000 title claims abstract description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 26
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000000066 reactive distillation Methods 0.000 title 1
- 238000004821 distillation Methods 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- 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 abstract description 12
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 12
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 150000002334 glycols Chemical class 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 45
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 29
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical group COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 abstract description 6
- 238000007796 conventional method Methods 0.000 abstract description 3
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
- 239000002994 raw material Substances 0.000 description 9
- 229920001429 chelating resin Polymers 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000001268 conjugating effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
-
- 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
- Y02P20/10—Process efficiency
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019990008051A KR100286571B1 (ko) | 1999-03-11 | 1999-03-11 | 반응증류를 이용한 글리콜 에스테르의 제조방법 |
| JP2000062203A JP2000264857A (ja) | 1999-03-11 | 2000-03-07 | 反応蒸留を用いるグリコールエステルの製造方法 |
| CNB001037471A CN1163467C (zh) | 1999-03-11 | 2000-03-07 | 利用反应性蒸馏过程制备二元醇酯的方法 |
| TW089104297A TW539668B (en) | 1999-03-11 | 2000-03-09 | Method for preparing glycol ester using reactive distillation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019990008051A KR100286571B1 (ko) | 1999-03-11 | 1999-03-11 | 반응증류를 이용한 글리콜 에스테르의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20000060027A KR20000060027A (ko) | 2000-10-16 |
| KR100286571B1 true KR100286571B1 (ko) | 2001-03-15 |
Family
ID=19576199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019990008051A KR100286571B1 (ko) | 1999-03-11 | 1999-03-11 | 반응증류를 이용한 글리콜 에스테르의 제조방법 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP2000264857A (zh) |
| KR (1) | KR100286571B1 (zh) |
| CN (1) | CN1163467C (zh) |
| TW (1) | TW539668B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101134659B1 (ko) | 2010-09-06 | 2012-04-09 | 이수화학 주식회사 | 프로필렌 글리콜 모노메틸 에테르 아세테이트의 제조방법 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100779521B1 (ko) * | 2005-07-15 | 2007-11-28 | 주식회사 엘지화학 | 카르복실산 및 에스테르 화합물의 병산 방법 |
| CN102206153A (zh) * | 2010-03-31 | 2011-10-05 | 东莞市同舟化工有限公司 | 一种丙二醇甲醚乙酸酯的连续合成方法 |
| CA2910976C (en) * | 2013-05-03 | 2021-03-30 | Dow Global Technologies Llc | Process for equilibrium-limited reactions |
| KR101349106B1 (ko) * | 2013-08-20 | 2014-01-08 | 에스케이종합화학 주식회사 | 반응증류를 이용한 글리콜 에스테르의 제조방법 |
| CN104845735A (zh) * | 2015-04-29 | 2015-08-19 | 四川银帆生物科技有限公司 | 利用酿酒副产物黄水制取香味液过程中的二次酯化工艺 |
| CN106187754B (zh) * | 2015-05-06 | 2019-05-14 | 中国科学院大连化学物理研究所 | 一种催化精馏生产芳香酸酯的方法 |
| KR102533952B1 (ko) * | 2020-02-26 | 2023-05-26 | 영남대학교 산학협력단 | 프로필렌 글리콜 메틸 에테르 아세테이트 제조 장치 및 제조 방법 |
| KR102528573B1 (ko) * | 2020-12-08 | 2023-05-04 | 주식회사 켐트로닉스 | 프로필렌 글리콜 메틸 에테르 아세테이트 제조 방법 |
| KR102399263B1 (ko) * | 2021-08-09 | 2022-05-17 | 에스케이머티리얼즈퍼포먼스 주식회사 | 프로필렌 글리콜 모노메틸 에테르 아세테이트의 제조방법 |
| KR102498772B1 (ko) * | 2021-11-29 | 2023-02-10 | 주식회사 켐트로닉스 | 초고순도 pgmea의 제조방법 |
-
1999
- 1999-03-11 KR KR1019990008051A patent/KR100286571B1/ko not_active IP Right Cessation
-
2000
- 2000-03-07 CN CNB001037471A patent/CN1163467C/zh not_active Expired - Lifetime
- 2000-03-07 JP JP2000062203A patent/JP2000264857A/ja active Pending
- 2000-03-09 TW TW089104297A patent/TW539668B/zh not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101134659B1 (ko) | 2010-09-06 | 2012-04-09 | 이수화학 주식회사 | 프로필렌 글리콜 모노메틸 에테르 아세테이트의 제조방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1268505A (zh) | 2000-10-04 |
| JP2000264857A (ja) | 2000-09-26 |
| KR20000060027A (ko) | 2000-10-16 |
| CN1163467C (zh) | 2004-08-25 |
| TW539668B (en) | 2003-07-01 |
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