CA1209584A - Acetals d'ether glycolique a fonction nitrile - Google Patents

Acetals d'ether glycolique a fonction nitrile

Info

Publication number: CA1209584A
Authority: CA; Canada
Prior art keywords: compound; nitrile; compounds; glycol ether; fluids
Prior art date: 1983-10-06
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

CA000438519A

Other languages

English (en)

Inventor

Robert L. Reierson

Gary P. Rabold

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.)

Dow Chemical Co

Original Assignee

Dow Chemical 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.)

1983-10-06

Filing date

1983-10-06

Publication date

1986-08-12

1983-10-06 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1983-10-06 Priority to CA000438519A priority Critical patent/CA1209584A/fr

1986-08-12 Application granted granted Critical

1986-08-12 Publication of CA1209584A publication Critical patent/CA1209584A/fr

Status Expired legal-status Critical Current

Links

150000002825 nitriles Chemical class 0.000 title claims abstract description 18
-1 glycol ether acetals Chemical class 0.000 title abstract description 15
239000012530 fluid Substances 0.000 claims abstract description 44
150000001875 compounds Chemical class 0.000 claims abstract description 37
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
NKFSAWUWIUIAEG-UHFFFAOYSA-N 4,4-bis(2-methoxyethoxy)butanenitrile Chemical compound COCCOC(CCC#N)OCCOC NKFSAWUWIUIAEG-UHFFFAOYSA-N 0.000 claims description 2
NSQNWCNMONBGCQ-UHFFFAOYSA-N 4-methoxy-4-[2-(2-methoxyethoxy)ethoxy]butanenitrile Chemical compound COCCOCCOC(OC)CCC#N NSQNWCNMONBGCQ-UHFFFAOYSA-N 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000005540 biological transmission Effects 0.000 claims 2
UFXWQBJLTHUZAM-UHFFFAOYSA-N 4,4-bis(1-methoxypropan-2-yloxy)butanenitrile Chemical compound COCC(C)OC(CCC#N)OC(C)COC UFXWQBJLTHUZAM-UHFFFAOYSA-N 0.000 claims 1
229920001971 elastomer Polymers 0.000 abstract description 10
238000009835 boiling Methods 0.000 abstract description 7
125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
239000000306 component Substances 0.000 description 7
239000000654 additive Substances 0.000 description 5
239000000376 reactant Substances 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
150000001241 acetals Chemical class 0.000 description 4
238000009472 formulation Methods 0.000 description 4
XJHNCGVHPLDMRK-UHFFFAOYSA-N 4,4-dimethoxybutanenitrile Chemical compound COC(OC)CCC#N XJHNCGVHPLDMRK-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
238000000034 method Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000001346 alkyl aryl ethers Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
239000011521 glass Substances 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
BPCMEVVBTRJOEW-UHFFFAOYSA-N 1,1-bis[2-(2-methoxyethoxy)ethoxy]butane Chemical compound COCCOCCOC(CCC)OCCOCCOC BPCMEVVBTRJOEW-UHFFFAOYSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Substances COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
HYXYOUQFKIFDET-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO.COCCOCCO HYXYOUQFKIFDET-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
RPXAHWKRPYUVLR-UHFFFAOYSA-N 4,4-bis[2-(2-methoxyethoxy)ethoxy]butanenitrile Chemical compound COCCOCCOC(CCC#N)OCCOCCOC RPXAHWKRPYUVLR-UHFFFAOYSA-N 0.000 description 1
GZIBEOIFNMHZFW-UHFFFAOYSA-N 4-methoxy-4-(1-methoxypropan-2-yloxy)butanenitrile Chemical compound COCC(C)OC(OC)CCC#N GZIBEOIFNMHZFW-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000007037 hydroformylation reaction Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
208000014674 injury Diseases 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
238000003032 molecular docking Methods 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
GUYXXEXGKVKXAW-UHFFFAOYSA-N prop-2-enenitrile Chemical compound C=CC#N.C=CC#N GUYXXEXGKVKXAW-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000008961 swelling Effects 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000003420 transacetalization reaction Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Landscapes

Lubricants (AREA)

CA000438519A 1983-10-06 1983-10-06 Acetals d'ether glycolique a fonction nitrile Expired CA1209584A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000438519A CA1209584A (fr)	1983-10-06	1983-10-06	Acetals d'ether glycolique a fonction nitrile

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000438519A CA1209584A (fr)	1983-10-06	1983-10-06	Acetals d'ether glycolique a fonction nitrile

Publications (1)

Publication Number	Publication Date
CA1209584A true CA1209584A (fr)	1986-08-12

Family

ID=4126240

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000438519A Expired CA1209584A (fr)	1983-10-06	1983-10-06	Acetals d'ether glycolique a fonction nitrile

Country Status (1)

Country	Link
CA (1)	CA1209584A (fr)

1983
- 1983-10-06 CA CA000438519A patent/CA1209584A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2003-10-06	MKEX	Expiry

Publication	Publication Date	Title
CA1106354A (fr)	1981-08-04	Fluides d'hydraulique
US3637794A (en)	1972-01-25	Borate esters prepared by successive reactions of boric acid with glycol monoethers and polyols
US3654155A (en)	1972-04-04	Esters of phosphorodithioates
US2824141A (en)	1958-02-18	Fluoroethers
US4141851A (en)	1979-02-27	Silane derivatives
US3972822A (en)	1976-08-03	Water-insensitive and stable hydraulic fluid compositions
US4116846A (en)	1978-09-26	Hydraulic fluid compositions comprising borate esters
CA1047480A (fr)	1979-01-30	Fluides hydrauliques prepares avec des esters de borate
US2973388A (en)	1961-02-28	Aliphatic polyethers
US4298488A (en)	1981-11-03	Hydraulic fluid composition containing glycol ethers and borate ester
ATE12652T1 (de)	1985-04-15	Verfahren zur herstellung von insbesondere als elektroisolierharze verwendbaren hitzehaertbaren siliconharzen.
US4219434A (en)	1980-08-26	Hydraulic fluid compositions based on mixed glycol ether-glycol boric acid esters
US4659861A (en)	1987-04-21	Novel nitrile functional glycol ether acetals
CA1083593A (fr)	1980-08-12	Derives des esterethers de silane servant dans des fluides hydrauliques
US4320024A (en)	1982-03-16	Hydraulic fluids containing cyano derivatives of cyclic ketals and acetals
JPH0458520B2 (fr)	1992-09-17
EP0733618B1 (fr)	1999-06-09	Monocarbonates, leur utilisation et procédé de préparation de compositions contenant des monocarbonates
US3563893A (en)	1971-02-16	Chemical composition
RU2078122C1 (ru)	1997-04-27	Тормозная жидкость
RU2078121C1 (ru)	1997-04-27	Тормозная жидкость
US4354028A (en)	1982-10-12	Piperazine derivatives
US5302760A (en)	1994-04-12	Stability additive for perfluoropolyalkylethers
US5196130A (en)	1993-03-23	Lubricity additive for high-temperature gas turbine engine oils
EP0080530B1 (fr)	1985-08-28	Fluides hydrauliques contenant des dérivés cyano de cétales et acétales cycliques
RU2041249C1 (ru)	1995-08-09	Эпиламирующий состав