CA1283415C - Acetals d'amide bicyclique prepares a partir de nitriles organiques et de dialcanolamines a une temperature inferieure a environ 140 c, et produit isole par extraction par solvant - Google Patents

Acetals d'amide bicyclique prepares a partir de nitriles organiques et de dialcanolamines a une temperature inferieure a environ 140 c, et produit isole par extraction par solvant

Info

Publication number: CA1283415C
Authority: CA; Canada
Prior art keywords: carbon atoms; bicyclic amide; solvent; amine; group containing
Prior art date: 1986-11-14
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 - Lifetime

Application number

CA000523061A

Other languages

English (en)

Inventor

Anil B. Goel

Harvey J. Richards

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.)

Ashland LLC

Original Assignee

Ashland Oil Inc

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.)

1986-11-14

Filing date

1986-11-14

Publication date

1991-04-23

1986-11-14 Application filed by Ashland Oil Inc filed Critical Ashland Oil Inc

1986-11-14 Priority to CA000523061A priority Critical patent/CA1283415C/fr

1991-04-23 Application granted granted Critical

1991-04-23 Publication of CA1283415C publication Critical patent/CA1283415C/fr

2008-04-23 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

-1 Bicyclic amide acetals Chemical class 0.000 title claims abstract description 45
150000002825 nitriles Chemical class 0.000 title claims abstract description 21
150000001412 amines Chemical class 0.000 title claims abstract description 17
238000000638 solvent extraction Methods 0.000 title description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 37
238000000034 method Methods 0.000 claims abstract description 19
239000002904 solvent Substances 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims abstract description 14
239000011541 reaction mixture Substances 0.000 claims abstract description 13
229930195733 hydrocarbon Natural products 0.000 claims abstract description 4
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 4
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 28
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 27
229940043237 diethanolamine Drugs 0.000 claims description 27
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 7
125000002877 alkyl aryl group Chemical group 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical group N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 3
125000000732 arylene group Chemical group 0.000 claims description 2
SZKKNEOUHLFYNA-UHFFFAOYSA-N undecanenitrile Chemical group CCCCCCCCCCC#N SZKKNEOUHLFYNA-UHFFFAOYSA-N 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
238000000605 extraction Methods 0.000 abstract description 12
150000001241 acetals Chemical class 0.000 abstract description 8
238000002360 preparation method Methods 0.000 abstract description 3
239000003822 epoxy resin Substances 0.000 abstract 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
229920000647 polyepoxide Polymers 0.000 abstract 1
239000004814 polyurethane Substances 0.000 abstract 1
229920002635 polyurethane Polymers 0.000 abstract 1
238000000746 purification Methods 0.000 abstract 1
239000000126 substance Substances 0.000 abstract 1
239000000047 product Substances 0.000 description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
125000002619 bicyclic group Chemical group 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
150000001408 amides Chemical class 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000000284 extract Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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 3
238000004821 distillation Methods 0.000 description 3
238000004508 fractional distillation Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000000926 separation method Methods 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 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
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1

Landscapes

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

CA000523061A 1986-11-14 1986-11-14 Acetals d'amide bicyclique prepares a partir de nitriles organiques et de dialcanolamines a une temperature inferieure a environ 140 c, et produit isole par extraction par solvant Expired - Lifetime CA1283415C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000523061A CA1283415C (fr)	1986-11-14	1986-11-14	Acetals d'amide bicyclique prepares a partir de nitriles organiques et de dialcanolamines a une temperature inferieure a environ 140 c, et produit isole par extraction par solvant

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000523061A CA1283415C (fr)	1986-11-14	1986-11-14	Acetals d'amide bicyclique prepares a partir de nitriles organiques et de dialcanolamines a une temperature inferieure a environ 140 c, et produit isole par extraction par solvant

Publications (1)

Publication Number	Publication Date
CA1283415C true CA1283415C (fr)	1991-04-23

Family

ID=4134355

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000523061A Expired - Lifetime CA1283415C (fr)	1986-11-14	1986-11-14	Acetals d'amide bicyclique prepares a partir de nitriles organiques et de dialcanolamines a une temperature inferieure a environ 140 c, et produit isole par extraction par solvant

Country Status (1)

Country	Link
CA (1)	CA1283415C (fr)

1986
- 1986-11-14 CA CA000523061A patent/CA1283415C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1993-10-25	MKLA	Lapsed

Publication	Publication Date	Title
GB1560549A (en)	1980-02-06	Manufacture of n-substituted glycinonitriles and amino acid salts
CA1283415C (fr)	1991-04-23	Acetals d'amide bicyclique prepares a partir de nitriles organiques et de dialcanolamines a une temperature inferieure a environ 140 c, et produit isole par extraction par solvant
CA1126760A (fr)	1982-06-29	Hydrogenation de nitriles aromatiques en amines primaires
US4652655A (en)	1987-03-24	Bicyclic amide acetals are prepared from organic nitriles and dialkanol amines at below about 140° C. and product is isolated by solvent extraction
US5070202A (en)	1991-12-03	Cyanobutylation of amines with 2-pentenitrile
Lindström et al.	1997	A stereospecific synthesis of vicinal amino alcohols by aminolysis of vinylepoxides
US4719309A (en)	1988-01-12	Preparation of imidazoles
EP0267976B1 (fr)	1990-08-29	Procédé de préparation d'acétals d'amide bicycliques
EP0125726B2 (fr)	1992-09-09	Procédé pour la préparation d'alkylisocyanates
Brace	1993	Amides as nucleophiles: reaction of alkyl halides with amides or with amides and water. A new look at an old reaction
US4864040A (en)	1989-09-05	Monohalogenotrifluorooxetane and its preparation
CA1249590A (fr)	1989-01-31	Preparation d'un acetal d'amide bicyclique
US12312445B2 (en)	2025-05-27	Branched organosilanol compounds and methods for the preparation and use thereof
US3708515A (en)	1973-01-02	Process of preparing gamma-cyanobutyraldimines
JPH0422914B2 (fr)	1992-04-20
FR2521564A1 (fr)	1983-08-19	Composes de silane utiles comme agents d'ensimage du verre ou comme promoteurs d'adherence
Bissinger et al.	1948	A study of the reaction of phenol with thionyl chloride
US4079086A (en)	1978-03-14	Process for reacting alkyl epoxides with glycols
CA1174686A (fr)	1984-09-18	Methode d'obtention de composes benzeniques substitues par des groupements alcoyle et alcoxyalcoyle
US5126476A (en)	1992-06-30	Process for the preparation of aryl-, heteroaryl-, or cycloalkyl-substituted alkyl urethanes and isocyanates
US4376861A (en)	1983-03-15	Method for preparing 2-alkenyl-2-oxazolines
US4418201A (en)	1983-11-29	Process for preparation of N-heterocyclic compounds
CA1148173A (fr)	1983-06-14	Preparations d'azomethines aromatiques
US4381265A (en)	1983-04-26	Aromatic nitrile-containing compounds useful as dyestuff intermediates
US5034523A (en)	1991-07-23	Process for preparing a 1,4-diazacycloheptan-2-one with a mixture of alkylated diamines