CA1094100A - Obtention d'esters de poly-(ether de tetramethylene) glycol - Google Patents

Obtention d'esters de poly-(ether de tetramethylene) glycol

Info

Publication number: CA1094100A
Authority: CA; Canada
Prior art keywords: catalyst; carbon atoms; polymer; glycol; tetramethylene ether
Prior art date: 1976-03-31
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

CA275,046A

Other languages

English (en)

Inventor

George E. Heinsohn

Gerfried Pruckmayr

Ivan M. Robinson

Walter W. Gilbert

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.)

1976-03-31

Filing date

1977-03-29

Publication date

1981-01-20

1977-03-29 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1981-01-20 Application granted granted Critical

1981-01-20 Publication of CA1094100A publication Critical patent/CA1094100A/fr

Status Expired legal-status Critical Current

Links

LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 13
150000002148 esters Chemical class 0.000 title claims description 10
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 68
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 60
239000003054 catalyst Substances 0.000 claims description 59
238000006243 chemical reaction Methods 0.000 claims description 56
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 44
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 34
238000000034 method Methods 0.000 claims description 31
229920000642 polymer Polymers 0.000 claims description 31
239000000178 monomer Substances 0.000 claims description 22
239000002243 precursor Substances 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 18
229920001577 copolymer Polymers 0.000 claims description 15
-1 poly(tetramethylene ether) Polymers 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 10
UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 9
150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 8
150000008064 anhydrides Chemical class 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 5
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000005647 linker group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000000524 functional group Chemical group 0.000 claims description 2
239000011268 mixed slurry Substances 0.000 claims description 2
TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 claims description 2
230000002844 continuous effect Effects 0.000 claims 1
239000000376 reactant Substances 0.000 description 27
239000000047 product Substances 0.000 description 22
239000000203 mixture Substances 0.000 description 18
150000002500 ions Chemical class 0.000 description 15
229960000583 acetic acid Drugs 0.000 description 13
238000006116 polymerization reaction Methods 0.000 description 9
238000001914 filtration Methods 0.000 description 8
229920000909 polytetrahydrofuran Polymers 0.000 description 7
239000000243 solution Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 5
239000002002 slurry Substances 0.000 description 5
238000005292 vacuum distillation Methods 0.000 description 5
JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000007792 addition Methods 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
230000036647 reaction Effects 0.000 description 3
239000005977 Ethylene Substances 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
238000001035 drying Methods 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
230000000977 initiatory effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
AYCANDRGVPTASA-UHFFFAOYSA-N 1-bromo-1,2,2-trifluoroethene Chemical group FC(F)=C(F)Br AYCANDRGVPTASA-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000004322 Butylated hydroxytoluene Substances 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
241000518994 Conta Species 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
101150083807 HSD17B10 gene Proteins 0.000 description 1
101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229920000557 Nafion® Polymers 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229940095259 butylated hydroxytoluene Drugs 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical group CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
RKFCDGOVCBYSEW-AUUKWEANSA-N tmeg Chemical compound COC=1C(OC)=CC(C(OC(C=2OC)=C34)=O)=C3C=1OC(=O)C4=CC=2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RKFCDGOVCBYSEW-AUUKWEANSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1

Landscapes

Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA275,046A 1976-03-31 1977-03-29 Obtention d'esters de poly-(ether de tetramethylene) glycol Expired CA1094100A (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date
US67255576A	1976-03-31	1976-03-31
US67255676A	1976-03-31	1976-03-31
US672,555		1976-03-31
US672,556		1976-03-31
US75121176A	1976-12-16	1976-12-16
US751,211		1976-12-16

Publications (1)

Publication Number	Publication Date
CA1094100A true CA1094100A (fr)	1981-01-20

Family

ID=27418250

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA275,046A Expired CA1094100A (fr)	1976-03-31	1977-03-29	Obtention d'esters de poly-(ether de tetramethylene) glycol

Country Status (1)

Country	Link
CA (1)	CA1094100A (fr)

1977
- 1977-03-29 CA CA275,046A patent/CA1094100A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-01-20	MKEX	Expiry

Publication	Publication Date	Title
US4163115A (en)	1979-07-31	Preparation of esters of poly-(tetramethylene ether) glycol
US4120903A (en)	1978-10-17	Method for preparing poly(tetramethylene ether) glycol
US4139567A (en)	1979-02-13	Method for preparing copolyether glycols
US4209635A (en)	1980-06-24	Process for producing perfluorinated vinyl ether having ester group
EP0567331A2 (fr)	1993-10-27	Procédé pour la production de l'acide acétique à partir de méthanol et de monoxyde de carbone en présence d'un catalyseur supporté de Rhodium
US5149862A (en)	1992-09-22	Preparation of polytetramethylene ether glycol using an acidic zirconia catalyst
CA1275542C (fr)	1990-10-23	Copolymeres de monomeres acrylate contenant de l'alcool vinylique et du fluor
US5130470A (en)	1992-07-14	Polymerization of tetrahydrofuran using a fluorinated acidic catalyst and maleic acid/maleic anhydride mixture as molecular weight control agent
CN102482409B (zh)	2014-01-08	改进的聚醚二醇制备方法
EP0571506A1 (fr)	1993-12-01	Polymerisation de tetrahydrofurane afin de produire de l'ether glycol de polytetramethylene au moyen d'un catalyseur en resine fluoruree modifiee contenant des groupes d'acides sulfoniques.
JPS5918372B2 (ja)	1984-04-26	メタノ−ルからエタノ−ルへの選択的同族体化方法
CA1094100A (fr)	1981-01-20	Obtention d'esters de poly-(ether de tetramethylene) glycol
US2391920A (en)	1946-01-01	Polymerization catalysts
GB1575529A (en)	1980-09-24	Polytetramethylene ether glycol esters
JP2005503463A (ja)	2005-02-03	ポリオキシアルキレンポリエーテル生成物の製造方法
US4112209A (en)	1978-09-05	Process for making polystyrene
JPS6111969B2 (fr)	1986-04-05
US2425638A (en)	1947-08-12	Polymerization of ethylene
JPS637571B2 (fr)	1988-02-17
Chen et al.	1999	The kinetics of diethylene glycol formation from bis‐hydroxyethyl terephthalate with antimony catalyst in the preparation of PET
US5010153A (en)	1991-04-23	Copolymers of vinyl acetate and fluorine-containing acrylate monomers
US4156101A (en)	1979-05-22	Low molecular weight tert.-alcohols
KR19980020821A (ko)	1998-06-25	지방족 폴리카보네이트의 중합방법
JPS6251943B2 (fr)	1987-11-02
JP2723426B2 (ja)	1998-03-09	含フッ素ビニルエーテルの製造方法