IE33399B1 - Esterification and extraction process - Google Patents
Esterification and extraction processInfo
- Publication number
- IE33399B1 IE33399B1 IE138569A IE138569A IE33399B1 IE 33399 B1 IE33399 B1 IE 33399B1 IE 138569 A IE138569 A IE 138569A IE 138569 A IE138569 A IE 138569A IE 33399 B1 IE33399 B1 IE 33399B1
- Authority
- IE
- Ireland
- Prior art keywords
- acids
- esters
- mixed
- oxidation
- water
- Prior art date
Links
- 230000032050 esterification Effects 0.000 title abstract 3
- 238000005886 esterification reaction Methods 0.000 title abstract 3
- 238000000605 extraction Methods 0.000 title abstract 3
- 239000002253 acid Substances 0.000 abstract 7
- 150000007513 acids Chemical class 0.000 abstract 7
- 150000002148 esters Chemical class 0.000 abstract 7
- 230000003647 oxidation Effects 0.000 abstract 5
- 238000007254 oxidation reaction Methods 0.000 abstract 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 3
- 229910017604 nitric acid Inorganic materials 0.000 abstract 3
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 abstract 2
- 239000008346 aqueous phase Substances 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 2
- 230000036571 hydration Effects 0.000 abstract 2
- 238000006703 hydration reaction Methods 0.000 abstract 2
- 239000011976 maleic acid Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000012074 organic phase Substances 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 abstract 1
- 229930006000 Sucrose Natural products 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 150000001279 adipic acids Chemical class 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 125000005233 alkylalcohol group Chemical group 0.000 abstract 1
- -1 alkylene glycol Chemical compound 0.000 abstract 1
- 150000001720 carbohydrates Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 235000015165 citric acid Nutrition 0.000 abstract 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003925 fat Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 238000000855 fermentation Methods 0.000 abstract 1
- 230000004151 fermentation Effects 0.000 abstract 1
- 150000002311 glutaric acids Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 235000014655 lactic acid Nutrition 0.000 abstract 1
- 229940040102 levulinic acid Drugs 0.000 abstract 1
- 150000004722 levulinic acids Chemical class 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid group Chemical group C(C(=O)O)(=O)O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 238000000638 solvent extraction Methods 0.000 abstract 1
- 150000003444 succinic acids Chemical class 0.000 abstract 1
- 239000005720 sucrose Substances 0.000 abstract 1
- 239000003784 tall oil Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
- C07C51/316—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with oxides of nitrogen or nitrogen-containing mineral acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
- C07C51/493—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification whereby carboxylic acid esters are formed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US04/766,476 US4076948A (en) | 1968-10-10 | 1968-10-10 | Process for treatment of adipic acid mother liquor |
| US04/851,445 US4082788A (en) | 1968-10-10 | 1969-08-19 | Esterification and extraction process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33399L IE33399L (en) | 1970-04-10 |
| IE33399B1 true IE33399B1 (en) | 1974-06-12 |
Family
ID=27117750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE138569A IE33399B1 (en) | 1968-10-10 | 1969-10-07 | Esterification and extraction process |
Country Status (11)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1162571A (en) * | 1980-06-11 | 1984-02-21 | Velsicol Chemical Corporation | Process for preparing high assay dicamba |
| AU3384097A (en) * | 1996-06-10 | 1998-01-07 | Renewable Energy Development Corporation | Methods for synthesis of high purity carboxylic and fatty acids |
| US7378549B2 (en) | 2004-01-26 | 2008-05-27 | Shell Oil Company | Process for the reactive extractive extraction of levulinic acid |
| US7501062B2 (en) * | 2005-02-22 | 2009-03-10 | Shell Oil Company | Process for permeation enhanced reactive extraction of levulinic acid |
| WO2010037807A1 (de) * | 2008-10-01 | 2010-04-08 | Basf Se | Verfahren zur herstellung von polycarbonsäurealkylestern |
| FR2957075B1 (fr) * | 2010-03-04 | 2012-06-22 | Centre Nat Rech Scient | Procede d'obtention de compositions de biosolvants par esterification et compositions de biosolvants obtenues |
| US20140316161A1 (en) | 2011-11-23 | 2014-10-23 | Segetis, Inc. | Process to prepare levulinic acid |
| US9073841B2 (en) | 2012-11-05 | 2015-07-07 | Segetis, Inc. | Process to prepare levulinic acid |
| WO2014125020A1 (en) * | 2013-02-14 | 2014-08-21 | Purac Biochem Bv | Method for preparing methyl lactate |
| CN112441915A (zh) * | 2019-09-04 | 2021-03-05 | 中国石油化工股份有限公司 | 己二酸结晶精制工艺中结晶母液的处理方法 |
| CN114436843B (zh) * | 2020-11-04 | 2024-07-26 | 长沙资材科技有限公司 | 一种环己烷连续生产己二酸二甲酯的方法 |
| CN114717056B (zh) * | 2022-04-25 | 2023-07-18 | 广东省农业科学院农业质量标准与监测技术研究所 | 一种酸催化油脂甲酯化的方法 |
-
1969
- 1969-10-07 GB GB4925569A patent/GB1282926A/en not_active Expired
- 1969-10-07 IE IE138569A patent/IE33399B1/xx unknown
- 1969-10-08 BE BE739957D patent/BE739957A/xx not_active IP Right Cessation
- 1969-10-09 LU LU59601D patent/LU59601A1/xx unknown
- 1969-10-09 NO NO403069A patent/NO133800C/no unknown
- 1969-10-09 CH CH1519769A patent/CH516500A/fr not_active IP Right Cessation
- 1969-10-09 AT AT952169A patent/AT297038B/de not_active IP Right Cessation
- 1969-10-09 SE SE1390169A patent/SE368193B/xx unknown
- 1969-10-10 NL NL6915365A patent/NL6915365A/xx unknown
- 1969-10-10 DE DE19691951299 patent/DE1951299C3/de not_active Expired
- 1969-10-10 FR FR6934713A patent/FR2020339A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CH516500A (fr) | 1971-12-15 |
| FR2020339A1 (enrdf_load_stackoverflow) | 1970-07-10 |
| DE1951299C3 (de) | 1981-05-14 |
| AT297038B (de) | 1972-03-10 |
| LU59601A1 (enrdf_load_stackoverflow) | 1970-01-09 |
| DE1951299A1 (de) | 1970-04-16 |
| NL6915365A (enrdf_load_stackoverflow) | 1970-04-14 |
| NO133800B (enrdf_load_stackoverflow) | 1976-03-22 |
| SE368193B (enrdf_load_stackoverflow) | 1974-06-24 |
| GB1282926A (en) | 1972-07-26 |
| NO133800C (enrdf_load_stackoverflow) | 1976-07-07 |
| BE739957A (enrdf_load_stackoverflow) | 1970-03-16 |
| IE33399L (en) | 1970-04-10 |
| DE1951299B2 (de) | 1973-11-15 |
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