CA1060480A - Purification de polyoxyalkylene, de polyesters et de polyols thermosensibles - Google Patents

Purification de polyoxyalkylene, de polyesters et de polyols thermosensibles

Info

Publication number: CA1060480A
Authority: CA; Canada
Prior art keywords: polyol; water; solvent; acid; crude
Prior art date: 1974-12-13
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

CA241,262A

Other languages

English (en)

Other versions

CA241262S (en

Inventor

John A. Muzzio

T. John (Jr.)

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.)

BASF Corp

Original Assignee

BASF Wyandotte Corp

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.)

1974-12-13

Filing date

1975-12-08

Publication date

1979-08-14

1975-12-08 Application filed by BASF Wyandotte Corp filed Critical BASF Wyandotte Corp

1979-08-14 Application granted granted Critical

1979-08-14 Publication of CA1060480A publication Critical patent/CA1060480A/fr

Status Expired legal-status Critical Current

Links

229920005862 polyol Polymers 0.000 title claims abstract description 91
150000003077 polyols Chemical class 0.000 title claims abstract description 90
239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 13
229920000570 polyether Polymers 0.000 title claims abstract description 13
238000000746 purification Methods 0.000 title abstract description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 57
239000002904 solvent Substances 0.000 claims abstract description 41
239000003054 catalyst Substances 0.000 claims abstract description 21
239000000203 mixture Substances 0.000 claims abstract description 16
238000000926 separation method Methods 0.000 claims abstract description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 15
239000003999 initiator Substances 0.000 claims abstract description 13
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 12
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 6
239000001569 carbon dioxide Substances 0.000 claims abstract description 6
229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 6
235000019253 formic acid Nutrition 0.000 claims abstract description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 35
238000000034 method Methods 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
239000012535 impurity Substances 0.000 claims description 7
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
235000011187 glycerol Nutrition 0.000 claims description 4
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
239000000600 sorbitol Substances 0.000 claims description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 3
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
ZFBMFVHQVPCSIN-UHFFFAOYSA-N [chloro(difluoro)methyl] hypochlorite Chemical compound ClOC(F)(F)Cl ZFBMFVHQVPCSIN-UHFFFAOYSA-N 0.000 claims description 2
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 2
229940029284 trichlorofluoromethane Drugs 0.000 claims description 2
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
238000006386 neutralization reaction Methods 0.000 abstract 1
235000019647 acidic taste Nutrition 0.000 description 12
238000007792 addition Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000002250 absorbent Substances 0.000 description 6
230000002745 absorbent Effects 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
239000011591 potassium Substances 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
238000005406 washing Methods 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
239000004814 polyurethane Substances 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
YTZRFUSYPGFDNC-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methyloxirane;oxirane Chemical compound C1CO1.CC1CO1.CCC(CO)(CO)CO YTZRFUSYPGFDNC-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
150000002148 esters Chemical group 0.000 description 2
-1 ether polyols Chemical class 0.000 description 2
238000010525 oxidative degradation reaction Methods 0.000 description 2
229920001228 polyisocyanate Polymers 0.000 description 2
239000005056 polyisocyanate Substances 0.000 description 2
238000003918 potentiometric titration Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000004088 simulation Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
BOKRKKCPFKUCIZ-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;2-methyloxirane Chemical compound CC1CO1.OCC(CO)(CO)CO BOKRKKCPFKUCIZ-UHFFFAOYSA-N 0.000 description 1
BJUPZVQSAAGZJL-UHFFFAOYSA-N 2-methyloxirane;propane-1,2,3-triol Chemical compound CC1CO1.OCC(O)CO BJUPZVQSAAGZJL-UHFFFAOYSA-N 0.000 description 1
241000237074 Centris Species 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000012206 bottled water Nutrition 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000008234 soft water Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1
238000011282 treatment Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/38—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Polyethers (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA241,262A 1974-12-13 1975-12-08 Purification de polyoxyalkylene, de polyesters et de polyols thermosensibles Expired CA1060480A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US53263574A	1974-12-13	1974-12-13

Publications (1)

Publication Number	Publication Date
CA1060480A true CA1060480A (fr)	1979-08-14

Family

ID=24122560

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA241,262A Expired CA1060480A (fr)	1974-12-13	1975-12-08	Purification de polyoxyalkylene, de polyesters et de polyols thermosensibles

Country Status (4)

Country	Link
BE (1)	BE836595A (fr)
CA (1)	CA1060480A (fr)
DE (1)	DE2554228A1 (fr)
FR (1)	FR2294202A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2854541A1 (de) *	1978-12-16	1980-06-26	Bayer Ag	Verfahren zur reinigung nichtionischer emulgatoren
DE3016112A1 (de) *	1980-04-25	1981-11-05	Bayer Ag, 5090 Leverkusen	Verfahren zur aufarbeitung von polyetherpolyolen
US4500705A (en) *	1984-01-09	1985-02-19	E. I. Du Pont De Nemours And Company	Method for reducing oligomeric cyclic ether content of a polymerizate
GB8700161D0 (en) *	1987-01-06	1987-02-11	Dow Chemical Nederland	Preparation of polyether compositions
DE3907911A1 (de) *	1989-03-11	1990-09-13	Bayer Ag	Verfahren zur entfernung von katalysatoren aus polyether-polyolen
DE19757709A1 (de) *	1997-12-23	1999-07-01	Basf Ag	Verfahren zur Herstellung oxalkylierter Amine

1975
- 1975-12-03 DE DE19752554228 patent/DE2554228A1/de active Pending
- 1975-12-08 CA CA241,262A patent/CA1060480A/fr not_active Expired
- 1975-12-12 BE BE162711A patent/BE836595A/fr unknown
- 1975-12-12 FR FR7538093A patent/FR2294202A1/fr active Granted

Also Published As

Publication number	Publication date
BE836595A (fr)	1976-06-14
FR2294202A1 (fr)	1976-07-09
FR2294202B1 (fr)	1979-09-07
DE2554228A1 (de)	1976-06-16

Publication	Publication Date	Title
US3358042A (en)	1967-12-12	Process for recovering polytetramethylene ether glycol
US5010047A (en)	1991-04-23	Recovery of double metal cyanide complex catalyst from a polymer
EP0376157B1 (fr)	1992-10-14	Procédé de purification de polyols contenant des catalyseurs en utilisant des résines échangeuses d'ions
US4482750A (en)	1984-11-13	Process for removing alkaline catalysts from polyether polyols
JP2003526605A (ja)	2003-09-09	１，３−プロパンジオールの精製方法
CA1060480A (fr)	1979-08-14	Purification de polyoxyalkylene, de polyesters et de polyols thermosensibles
DE60026716T2 (de)	2006-11-23	Verfahren zur herstellung von polyäthern
CA2140499C (fr)	2005-09-06	Methode pour la purification de polyethers-polyols prepares avec des catalyseurs a cyanure double de metaux
DE19530388A1 (de)	1997-02-20	Geruchsarme, höhermolekulare Polyetherpolyole, ein Verfahren zu deren Herstellung sowie deren Verwendung für die Herstellung von auf Polyetherpolyolen aufbauenden Polymeren, Kosmetika und pharmazeutischen Produkten
EP0004536B1 (fr)	1981-11-25	Procédé pour réduire la quantité d'un oligomère d'éther cyclique d'un mélange polymérisé
JPH09509211A (ja)	1997-09-16	ポリエーテルポリオールからエステル交換反応触媒を除去する方法
DE2246552A1 (de)	1973-03-29	Verfahren zur herstellung eines polyphenylenaethers
EP1160228B1 (fr)	2006-07-12	Procédé de séparation de l'éthylène glycol
US4575568A (en)	1986-03-11	Removal of phenols from water
US4535189A (en)	1985-08-13	Polyol purification process
EP0734407B1 (fr)	1997-12-29	Procede de purification de polyols
DE602004003918T2 (de)	2007-10-11	Verfahren zur herstellung von polyetherpolyolen
US5288921A (en)	1994-02-22	Process for reducing unsaturation on polyols
EP0683162B1 (fr)	1998-09-23	Séparation de catalyseur molybdene
US4510334A (en)	1985-04-09	Method of preparing alkalihalide free oligomeric, brominous xylylene bisphenol ethers
WO2019215103A1 (fr)	2019-11-14	Séparation d'un catalyseur à base de cyanure bimétallique
US4672141A (en)	1987-06-09	Polyalkylene ether glycols
EP1132452A2 (fr)	2001-09-12	Procédé de production d'indène de distillat de goudron de charbon
DE4408004A1 (de)	1995-09-14	Verfahren zur Gewinnung von reinen, fließfähigen Alkali- oder Erdalkalisalzen aus den Salzrückständen der Polyetherpolyolproduktion
KR101310953B1 (ko)	2013-09-23	폴리올폐기물로부터의 폴리올 회수방법