CA1281729C - Procede sous pression atmospherique pour la preparation d'esters cycliques purs - Google Patents

Procede sous pression atmospherique pour la preparation d'esters cycliques purs

Info

Publication number: CA1281729C
Authority: CA; Canada
Prior art keywords: solvent; cyclic ester; inert gas; prepolymer; temperature
Prior art date: 1989-03-01
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

Application number

CA 592471

Other languages

English (en)

Inventor

Kamlesh Kumar Bhatia

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date 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 date listed.)

1989-03-01

Filing date

1989-03-01

Publication date

1991-03-19

1989-03-01 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1989-03-01 Priority to CA 592471 priority Critical patent/CA1281729C/fr

1991-03-19 Application granted granted Critical

1991-03-19 Publication of CA1281729C publication Critical patent/CA1281729C/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title abstract description 10
125000004122 cyclic group Chemical group 0.000 title abstract description 7
-1 cyclic ester Chemical class 0.000 claims abstract description 39
239000002904 solvent Substances 0.000 claims abstract description 37
239000011261 inert gas Substances 0.000 claims abstract description 30
150000002148 esters Chemical class 0.000 claims abstract description 17
229920000642 polymer Polymers 0.000 claims abstract description 12
239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 7
229920000570 polyether Polymers 0.000 claims abstract description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 45
238000000034 method Methods 0.000 claims description 43
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
239000012535 impurity Substances 0.000 claims description 17
RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical group O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims description 11
238000005336 cracking Methods 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
229920001400 block copolymer Polymers 0.000 claims description 5
238000001914 filtration Methods 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
238000005201 scrubbing Methods 0.000 claims description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
238000005119 centrifugation Methods 0.000 claims description 2
230000008014 freezing Effects 0.000 claims description 2
238000007710 freezing Methods 0.000 claims description 2
JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims 2
238000006243 chemical reaction Methods 0.000 abstract description 10
229920001577 copolymer Polymers 0.000 abstract description 4
238000010438 heat treatment Methods 0.000 abstract description 3
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 20
239000000047 product Substances 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 11
229960004275 glycolic acid Drugs 0.000 description 10
239000012065 filter cake Substances 0.000 description 9
238000002474 experimental method Methods 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 5
239000002002 slurry Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 4
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 4
239000000292 calcium oxide Substances 0.000 description 4
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 4
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
238000000746 purification Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000007789 gas Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000002245 particle Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
235000019647 acidic taste Nutrition 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
238000010923 batch production Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000010924 continuous production Methods 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229940116333 ethyl lactate Drugs 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000004310 lactic acid Substances 0.000 description 2
235000014655 lactic acid Nutrition 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
229940057867 methyl lactate Drugs 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000011269 tar Substances 0.000 description 2
239000002699 waste material Substances 0.000 description 2
OORRCVPWRPVJEK-UHFFFAOYSA-N 2-oxidanylethanoic acid Chemical compound OCC(O)=O.OCC(O)=O OORRCVPWRPVJEK-UHFFFAOYSA-N 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
101100270435 Mus musculus Arhgef12 gene Proteins 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
229910000410 antimony oxide Inorganic materials 0.000 description 1
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Inorganic materials O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 1
GHPGOEFPKIHBNM-UHFFFAOYSA-N antimony(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Sb+3].[Sb+3] GHPGOEFPKIHBNM-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000004737 colorimetric analysis Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
239000002360 explosive Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000007943 implant Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
230000000399 orthopedic effect Effects 0.000 description 1
VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000005070 sampling Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
YEAUATLBSVJFOY-UHFFFAOYSA-N tetraantimony hexaoxide Chemical compound O1[Sb](O2)O[Sb]3O[Sb]1O[Sb]2O3 YEAUATLBSVJFOY-UHFFFAOYSA-N 0.000 description 1
238000004227 thermal cracking Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA 592471 1989-03-01 1989-03-01 Procede sous pression atmospherique pour la preparation d'esters cycliques purs Expired CA1281729C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 592471 CA1281729C (fr)	1989-03-01	1989-03-01	Procede sous pression atmospherique pour la preparation d'esters cycliques purs

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 592471 CA1281729C (fr)	1989-03-01	1989-03-01	Procede sous pression atmospherique pour la preparation d'esters cycliques purs

Publications (1)

Publication Number	Publication Date
CA1281729C true CA1281729C (fr)	1991-03-19

Family

ID=4139715

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 592471 Expired CA1281729C (fr)	1989-03-01	1989-03-01	Procede sous pression atmospherique pour la preparation d'esters cycliques purs

Country Status (1)

Country	Link
CA (1)	CA1281729C (fr)

1989
- 1989-03-01 CA CA 592471 patent/CA1281729C/fr not_active Expired

Legal Events

Date	Code	Title	Description
2003-03-19	MKLA	Lapsed

Publication	Publication Date	Title
US4835293A (en)	1989-05-30	Atmospheric pressure process for preparing pure cyclic esters
US5502215A (en)	1996-03-26	Method for purification of lactide
AU640589B2 (en)	1993-08-26	Purifying glycolide and lactides using high pressure gas stream
JP3904230B2 (ja)	2007-04-11	１，３−プロパンジオールの精製
EP0038930A1 (fr)	1981-11-04	Procédé pour augmenter la capacitá d'un réacteur de polycondensation de polyesters
JPS63152375A (ja)	1988-06-24	高純度環状エステルの製造方法
US5117008A (en)	1992-05-26	Solvent scrubbing recovery of lactide and other dimeric cyclic esters
WO1995011218A1 (fr)	1995-04-27	Procede de separation du dimethanol de cyclohexane du dimethylterephtalate
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US4613678A (en)	1986-09-23	Esterification of aromatic dicarboxylic acids with cyclic alkylene carbonates
CA1281729C (fr)	1991-03-19	Procede sous pression atmospherique pour la preparation d'esters cycliques purs
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EP1199298B1 (fr)	2004-08-04	Procédé de fabrication d acide pyromellique raffine et d anhydride pyromellique raffine
US4327063A (en)	1982-04-27	Method of purifying cyclic dichlorophosphazenes containing trace amounts of protic impurities
WO1995004762A2 (fr)	1995-02-16	Solutions aqueuses et en phase liquide de poly(ether methylvinylique) obtenues a partir d'un monomere d'ether methylvinylique hautement purifie
US3952086A (en)	1976-04-20	Purification of crude chlorophosphazene compounds by treatment with Bronsted bases
US3272776A (en)	1966-09-13	Preparation of poly
CN115504957B (zh)	2024-07-23	一种乙交酯的精制方法及所得乙交酯
US4347351A (en)	1982-08-31	Linear polyesters from aromatic dicarboxylic acids and cyclic alkylene carbonates prepared using six-membered aromatic nitrogen-containing heterocyclic groups
US3960939A (en)	1976-06-01	Method for preparing sorbic acid
CN1046159A (zh)	1990-10-17	常压下制备纯环酯的方法
US3000871A (en)	1961-09-19	Method for purifying polyolefin
JPH02268179A (ja)	1990-11-01	環状エステルの製造方法
JPH10168077A (ja)	1998-06-23	ラクチドの製造方法