ZA200604400B - Process for the production of esters of mono-, di-or polycarboxylic acids - Google Patents
Process for the production of esters of mono-, di-or polycarboxylic acids Download PDFInfo
- Publication number
- ZA200604400B ZA200604400B ZA200604400A ZA200604400A ZA200604400B ZA 200604400 B ZA200604400 B ZA 200604400B ZA 200604400 A ZA200604400 A ZA 200604400A ZA 200604400 A ZA200604400 A ZA 200604400A ZA 200604400 B ZA200604400 B ZA 200604400B
- Authority
- ZA
- South Africa
- Prior art keywords
- water
- esterification
- process according
- ester
- reactor
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 73
- 150000002148 esters Chemical class 0.000 title claims description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 239000002253 acid Substances 0.000 title claims description 16
- 150000007513 acids Chemical class 0.000 title claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 111
- 229910001868 water Inorganic materials 0.000 claims description 111
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 108
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 96
- 238000006243 chemical reaction Methods 0.000 claims description 89
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 87
- 239000011976 maleic acid Substances 0.000 claims description 87
- 238000005886 esterification reaction Methods 0.000 claims description 83
- 230000032050 esterification Effects 0.000 claims description 65
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 55
- 239000003054 catalyst Substances 0.000 claims description 37
- 238000005984 hydrogenation reaction Methods 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 239000006096 absorbing agent Substances 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000005690 diesters Chemical class 0.000 claims description 11
- 125000005907 alkyl ester group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 282
- 239000000047 product Substances 0.000 description 33
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 30
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 16
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 13
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 13
- 238000007670 refining Methods 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000001530 fumaric acid Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 aliphatic monocarboxylic acids Chemical class 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-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 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 101100048480 Vaccinia virus (strain Western Reserve) UNG gene Proteins 0.000 description 2
- 150000001243 acetic acids Chemical class 0.000 description 2
- 150000001253 acrylic acids Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 101100410404 Arabidopsis thaliana PUMPKIN gene Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical class OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/177—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of a carboxy group
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0325530.4A GB0325530D0 (en) | 2003-10-31 | 2003-10-31 | Process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200604400B true ZA200604400B (en) | 2008-02-27 |
Family
ID=29725780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200604400A ZA200604400B (en) | 2003-10-31 | 2004-10-18 | Process for the production of esters of mono-, di-or polycarboxylic acids |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7816554B2 (zh) |
| EP (1) | EP1678117B1 (zh) |
| KR (1) | KR101191838B1 (zh) |
| CN (1) | CN1878743A (zh) |
| AR (1) | AR046567A1 (zh) |
| GB (1) | GB0325530D0 (zh) |
| MY (1) | MY148249A (zh) |
| TW (1) | TWI349002B (zh) |
| WO (1) | WO2005051885A1 (zh) |
| ZA (1) | ZA200604400B (zh) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7652167B2 (en) * | 2004-07-19 | 2010-01-26 | Board Of Trustees Of Michigan State University | Process for production of organic acid esters |
| US7667068B2 (en) | 2004-07-19 | 2010-02-23 | Board Of Trustees Of Michigan State University | Process for reactive esterification distillation |
| GB0421928D0 (en) | 2004-10-01 | 2004-11-03 | Davy Process Techn Ltd | Process |
| EP1842843A1 (de) | 2006-04-04 | 2007-10-10 | Basf Aktiengesellschaft | Verfahren zur Herstellung eines Carbonsäurealkylesters |
| DE102006039420A1 (de) * | 2006-08-23 | 2008-02-28 | Evonik Rohmax Additves Gmbh | Verfahren zur Herstellung von Methacrylatestern |
| EP2134819A4 (en) * | 2007-03-14 | 2016-11-16 | Endicott Biofuels Ii Llc | PREPARATION OF BIODIESEL FUELS WITH LOW GLYCEROL AND SULFUR CONTENT |
| MY153388A (en) * | 2007-03-14 | 2015-01-29 | Endicott Biofuels Ii Llc | Production of biodiesel fuels which are low in glycerin and sulfur |
| US8105399B2 (en) * | 2007-07-31 | 2012-01-31 | Endicott Biofuels Ii, Llc | Production of renewable diesel by pyrolysis and esterification |
| US20090036705A1 (en) * | 2007-07-31 | 2009-02-05 | Endicott Biofuels Ii, Llc | Production of Alkyl Esters from High Fatty Acid Feedstocks |
| US20090031618A1 (en) * | 2007-07-31 | 2009-02-05 | Endicott Biofuels Ii, Llc | Vacuum Distillation Process |
| US20090049739A1 (en) * | 2007-07-31 | 2009-02-26 | Endicott Biiofuels Ii, Llc | Production of Fuels with Superior Low Temperature Properties from Tall Oil or Fractionated Fatty Acids |
| US8105398B2 (en) * | 2007-08-27 | 2012-01-31 | Endicott Biofuels Ii, Llc | Production of ester-based fuels such as biodiesel from renewable starting materials |
| WO2009038865A1 (en) * | 2007-09-19 | 2009-03-26 | Endicott Biofuels Ii, Llc | Method for obtaining biodiesel, alternative fuels and renewable fuels tax credits and treatment |
| US20090076985A1 (en) * | 2007-09-19 | 2009-03-19 | Endicott Biofuels Ii, Llc | Method for Obtaining Biodiesel, Alternative Fuels and Renewable Fuels Tax Credits and Treatment |
| EP2247567B1 (en) * | 2008-01-24 | 2017-11-29 | Dorf Ketal Chemicals (I) Private Limited | Method of removing metals from hydrocarbon feedstock using esters of carboxylic acids |
| US20100168371A1 (en) * | 2008-12-31 | 2010-07-01 | Corrado Berti | Bio-Based Terephthalate Polyesters |
| US8946472B2 (en) | 2008-12-31 | 2015-02-03 | Sabic Innovative Plastics Ip B.V. | Bio-based terephthalate polyesters |
| US20100168461A1 (en) * | 2008-12-31 | 2010-07-01 | Corrado Berti | Bio-Based Terephthalate Polyesters |
| US20100168373A1 (en) * | 2008-12-31 | 2010-07-01 | Corrado Berti | Bio-Based Terephthalate Polyesters |
| US8415496B2 (en) | 2009-06-16 | 2013-04-09 | Amyris, Inc. | Biobased polyesters |
| US8367859B2 (en) | 2009-06-16 | 2013-02-05 | Amyris, Inc. | Cyclohexane 1,4 carboxylates |
| CA2765736A1 (en) | 2009-06-16 | 2010-12-23 | John W. Frost | Cyclohexene 1,4-carboxylates |
| WO2010148049A2 (en) | 2009-06-16 | 2010-12-23 | Draths Corporation | Preparation of trans, trans muconic acid and trans, trans muconates |
| EP2507200B1 (en) | 2009-12-02 | 2014-02-12 | Board Of Trustees Of Michigan State University | Carboxylic acid recovery and methods related thereto |
| WO2011085311A1 (en) | 2010-01-08 | 2011-07-14 | Draths Corporation | Methods for producing isomers of muconic acid and muconate salts |
| CN108863786A (zh) * | 2013-02-14 | 2018-11-23 | 普拉克生化公司 | 制备琥珀酸酯的方法 |
| GB201321627D0 (en) * | 2013-12-06 | 2014-01-22 | Johnson Matthey Davy Technologies Ltd | Process |
| WO2022065852A1 (ko) * | 2020-09-24 | 2022-03-31 | 주식회사 엘지화학 | 에스터계 조성물의 제조방법 |
| CN115006967B (zh) * | 2022-08-04 | 2022-11-18 | 浙江晨阳新材料有限公司 | 一种燃料电池生产中含醇废气的处理方法及装置 |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE206373C (zh) | ||||
| US1400849A (en) * | 1918-08-07 | 1921-12-20 | Us Ind Alcohol Co | Continuous process for the manufacture of esters |
| US2551625A (en) * | 1947-12-30 | 1951-05-08 | Standard Oil Dev Co | Distillation of oxygenated organic compounds |
| US2575243A (en) * | 1948-04-27 | 1951-11-13 | Standard Oil Dev Co | Extractive distillation of alcohols |
| US2610206A (en) | 1948-10-09 | 1952-09-09 | Distillers Co Yeast Ltd | Manufacture of methyl lactate |
| US2587753A (en) * | 1949-04-26 | 1952-03-04 | Stanolind Oil & Gas Co | Method for purifying alcohols |
| US2638481A (en) * | 1950-05-26 | 1953-05-12 | Hercules Powder Co Ltd | Maleic acid manufacture |
| GB727828A (en) | 1952-12-09 | 1955-04-06 | Chempatents Inc | Recovery of polycarboxylic acid anhydrides |
| GB763339A (en) | 1953-03-23 | 1956-12-12 | Chempatents Inc | Improvements in recovery of maleic and phthalic acid anhydrides |
| FR1089012A (fr) | 1953-10-08 | 1955-03-14 | Chempatents | Procédé de récupération des anhydrides d'acides polycarboxyliques à partir de mélanges gazeux dilués |
| GB1242320A (en) | 1968-01-30 | 1971-08-11 | Ucb Union Chimiqu Chemische Be | Process for the dehydration of maleic acid |
| US4058555A (en) * | 1969-07-18 | 1977-11-15 | El Paso Products Company | Process for the purification of mixed acids |
| US3862147A (en) | 1972-08-25 | 1975-01-21 | Petro Tex Chem Corp | Maleic anhydride process |
| GB1424747A (en) | 1973-08-28 | 1976-02-11 | Ucb Sa | Method and apparatus for the continuous dehydration of maleic acid |
| US4032458A (en) * | 1975-08-08 | 1977-06-28 | Petro-Tex Chemical Corporation | Production of 1,4-butanediol |
| DD206373A1 (de) * | 1982-03-16 | 1984-01-25 | Joachim Franke | Verfahren und vorrichtung zur abtrennung von milchsaeure aus rohloesungen |
| US4435595A (en) * | 1982-04-26 | 1984-03-06 | Eastman Kodak Company | Reactive distillation process for the production of methyl acetate |
| DE3222837A1 (de) * | 1982-06-18 | 1983-12-22 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von milchsaeuremethylester |
| GB8331793D0 (en) * | 1983-11-29 | 1984-01-04 | Davy Mckee Ltd | Process |
| GB8514002D0 (en) * | 1985-06-04 | 1985-07-10 | Davy Mckee Ltd | Process |
| DE3809417A1 (de) * | 1988-03-21 | 1989-10-12 | Henkel Kgaa | Verfahren zur kontinuierlichen veresterung von fettsaeuren |
| GB8618888D0 (en) * | 1986-08-01 | 1986-09-10 | Davy Mckee Ltd | Process |
| EP0277168A1 (en) | 1986-08-01 | 1988-08-10 | DAVY McKEE (LONDON) LIMITED | PROCESS FOR THE CO-PRODUCTION OF BUTANE-1,4-DIOL AND $i(GAMMA)-BUTYROLACTONE |
| GB2207914A (en) | 1987-07-30 | 1989-02-15 | Davy Mckee | Process for the production of a mixture of butane 1,4-diol gamma-butyrolactone and tetrahydrofuran |
| DE69027304T2 (de) | 1989-01-17 | 1997-01-23 | Davy Process Technology Ltd., London | Kontinuierliches Verfahren zur Herstellung von Carbonsäureestern |
| US5210296A (en) * | 1990-11-19 | 1993-05-11 | E. I. Du Pont De Nemours And Company | Recovery of lactate esters and lactic acid from fermentation broth |
| ZA973972B (en) | 1996-05-14 | 1998-03-23 | Kvaerner Process Tech Ltd | A process for the production of at least one C4 compound selected from butane-1,4-diol, gamma-butyrolactone and tetrahydrofuran. |
| ZA973971B (en) | 1996-05-15 | 1998-03-23 | Kvaerner Process Tech Ltd | A process for the production of at least one C4 compound selected from butane-1,4-diol, gamma-butyrolactone and tetrahydrofuran. |
| US5719311A (en) * | 1996-11-19 | 1998-02-17 | Industrial Technology Research Institute | Catalytic processes for esterification of carboxylic acids |
| BR9808785A (pt) | 1997-05-12 | 2000-08-08 | Reilly Ind Inc | Processos para produzir ésteres de citrato |
| GB9724004D0 (en) | 1997-11-13 | 1998-10-21 | Kvaerner Process Tech Ltd | Process |
| EE04110B1 (et) * | 1997-11-24 | 2003-08-15 | Energea-Umwelttechnologie Gmbh | Rasvhappe metüülestri valmistamise meetod ja seadmestik meetodi realiseerimiseks |
| EP0962438B1 (en) | 1998-03-23 | 2001-06-06 | Basf Aktiengesellschaft | Process for the preparation of 1,4-butanediol, butyrolactone and tetrahydrofuran. |
| US6045703A (en) * | 1998-06-15 | 2000-04-04 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
| ATE234805T1 (de) * | 2000-11-30 | 2003-04-15 | Chemial Spa | Verfahren zur veresterung in einem chromatographischen reaktor |
| CN1900139B (zh) * | 2000-12-07 | 2012-11-14 | 奇派特石化有限公司 | 制造缩聚物的方法 |
| US7667068B2 (en) * | 2004-07-19 | 2010-02-23 | Board Of Trustees Of Michigan State University | Process for reactive esterification distillation |
-
2003
- 2003-10-31 GB GBGB0325530.4A patent/GB0325530D0/en not_active Ceased
-
2004
- 2004-10-12 MY MYPI20044182A patent/MY148249A/en unknown
- 2004-10-18 TW TW093131560A patent/TWI349002B/zh not_active IP Right Cessation
- 2004-10-18 WO PCT/GB2004/004413 patent/WO2005051885A1/en active Application Filing
- 2004-10-18 ZA ZA200604400A patent/ZA200604400B/en unknown
- 2004-10-18 CN CNA2004800324096A patent/CN1878743A/zh active Pending
- 2004-10-18 EP EP04768940.1A patent/EP1678117B1/en not_active Expired - Lifetime
- 2004-10-18 KR KR1020067010282A patent/KR101191838B1/ko not_active IP Right Cessation
- 2004-10-18 US US10/577,374 patent/US7816554B2/en not_active Expired - Fee Related
- 2004-10-29 AR ARP040103968A patent/AR046567A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1678117B1 (en) | 2016-05-11 |
| GB0325530D0 (en) | 2003-12-03 |
| TW200530176A (en) | 2005-09-16 |
| MY148249A (en) | 2013-03-29 |
| EP1678117A1 (en) | 2006-07-12 |
| KR101191838B1 (ko) | 2012-10-16 |
| CN1878743A (zh) | 2006-12-13 |
| AR046567A1 (es) | 2005-12-14 |
| US7816554B2 (en) | 2010-10-19 |
| US20070129565A1 (en) | 2007-06-07 |
| KR20060127856A (ko) | 2006-12-13 |
| WO2005051885A1 (en) | 2005-06-09 |
| TWI349002B (en) | 2011-09-21 |
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