CA1074312A - Production d'un compose a base de n,n-piperazine disubstituee - Google Patents

Production d'un compose a base de n,n-piperazine disubstituee

Info

Publication number: CA1074312A
Authority: CA; Canada
Prior art keywords: substituted; alkyl; alkyl radical; dialkanolamine; phosphorus
Prior art date: 1975-06-02
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

CA253,291A

Other languages

English (en)

Inventor

Ernest L. Yeakey

Michael E. Brennan

Heinz Schulze

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.)

Texaco Development Corp

Original Assignee

Texaco Development 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.)

1975-06-02

Filing date

1976-05-26

Publication date

1980-03-25

1976-05-26 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1980-03-25 Application granted granted Critical

1980-03-25 Publication of CA1074312A publication Critical patent/CA1074312A/fr

Status Expired legal-status Critical Current

Links

-1 piperazine compound Chemical class 0.000 title claims abstract description 36
238000000034 method Methods 0.000 title claims abstract description 24
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title claims abstract description 14
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 20
239000000126 substance Substances 0.000 claims abstract description 15
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 12
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 12
239000011574 phosphorus Substances 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
239000000203 mixture Substances 0.000 claims abstract description 6
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims abstract 3
125000000217 alkyl group Chemical group 0.000 claims description 15
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
235000011007 phosphoric acid Nutrition 0.000 claims description 13
239000000376 reactant Substances 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 9
150000003016 phosphoric acids Chemical class 0.000 claims description 7
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
150000008064 anhydrides Chemical class 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 4
229910001463 metal phosphate Inorganic materials 0.000 claims description 4
CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
150000003017 phosphorus Chemical class 0.000 claims description 2
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical group C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims 1
150000005840 aryl radicals Chemical class 0.000 abstract description 4
125000003107 substituted aryl group Chemical group 0.000 abstract description 4
239000007791 liquid phase Substances 0.000 abstract description 3
239000011541 reaction mixture Substances 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 17
150000001875 compounds Chemical class 0.000 description 12
239000002253 acid Chemical class 0.000 description 10
150000003141 primary amines Chemical class 0.000 description 10
239000003054 catalyst Substances 0.000 description 9
150000004885 piperazines Chemical class 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 5
239000000463 material Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
YSBGRLGSDJOINT-UHFFFAOYSA-N 1-dodecyl-4-methylpiperazine Chemical compound CCCCCCCCCCCCN1CCN(C)CC1 YSBGRLGSDJOINT-UHFFFAOYSA-N 0.000 description 2
WQDDXVGJRSTLED-UHFFFAOYSA-N 1-methyl-4-phenylpiperazine Chemical compound C1CN(C)CCN1C1=CC=CC=C1 WQDDXVGJRSTLED-UHFFFAOYSA-N 0.000 description 2
VARKIGWTYBUWNT-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanol Chemical compound OCCN1CCN(CCO)CC1 VARKIGWTYBUWNT-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
238000003109 Karl Fischer titration Methods 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 description 2
229910000149 boron phosphate Inorganic materials 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
230000002939 deleterious effect Effects 0.000 description 2
238000004821 distillation Methods 0.000 description 2
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
150000003014 phosphoric acid esters Chemical group 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
125000001302 tertiary amino group Chemical group 0.000 description 2
LLZRSOPHIGKISM-UHFFFAOYSA-N 1,4-diphenylpiperazine Chemical compound C1CN(C=2C=CC=CC=2)CCN1C1=CC=CC=C1 LLZRSOPHIGKISM-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
KCYQJTPTODQXLK-UHFFFAOYSA-N 2,6-diethyl-1,4-dimethylpiperazine Chemical compound CCC1CN(C)CC(CC)N1C KCYQJTPTODQXLK-UHFFFAOYSA-N 0.000 description 1
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
KTGRTNZELMHPJN-UHFFFAOYSA-N 2-(2-dodecylpiperazin-1-yl)ethanol Chemical compound CCCCCCCCCCCCC1CNCCN1CCO KTGRTNZELMHPJN-UHFFFAOYSA-N 0.000 description 1
UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
XAJMBOZDPXFSDS-UHFFFAOYSA-N 4-[3-(4-methylpiperazin-1-yl)propyl]morpholine Chemical compound C1CN(C)CCN1CCCN1CCOCC1 XAJMBOZDPXFSDS-UHFFFAOYSA-N 0.000 description 1
239000005955 Ferric phosphate Substances 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
ZWBALHRZGYPNNG-UHFFFAOYSA-N Monomethyl phenylphosphonate Chemical compound COP(O)(=O)C1=CC=CC=C1 ZWBALHRZGYPNNG-UHFFFAOYSA-N 0.000 description 1
QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
OXDOANYFRLHSML-UHFFFAOYSA-N dimethoxyphosphorylbenzene Chemical compound COP(=O)(OC)C1=CC=CC=C1 OXDOANYFRLHSML-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
229940032958 ferric phosphate Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 1
229910000399 iron(III) phosphate Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
ZUYQAYFMISSPTF-UHFFFAOYSA-N methoxy-oxo-phenylphosphanium Chemical compound CO[P+](=O)C1=CC=CC=C1 ZUYQAYFMISSPTF-UHFFFAOYSA-N 0.000 description 1
GHZKGHQGPXBWSN-UHFFFAOYSA-N methyl(propan-2-yloxy)phosphinic acid Chemical compound CC(C)OP(C)(O)=O GHZKGHQGPXBWSN-UHFFFAOYSA-N 0.000 description 1
BCDIWLCKOCHCIH-UHFFFAOYSA-N methylphosphinic acid Chemical compound CP(O)=O BCDIWLCKOCHCIH-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000008301 phosphite esters Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000004448 titration Methods 0.000 description 1

Landscapes

Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA253,291A 1975-06-02 1976-05-26 Production d'un compose a base de n,n-piperazine disubstituee Expired CA1074312A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US58300675A	1975-06-02	1975-06-02

Publications (1)

Publication Number	Publication Date
CA1074312A true CA1074312A (fr)	1980-03-25

Family

ID=24331299

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA253,291A Expired CA1074312A (fr)	1975-06-02	1976-05-26	Production d'un compose a base de n,n-piperazine disubstituee

Country Status (1)

Country	Link
CA (1)	CA1074312A (fr)

1976
- 1976-05-26 CA CA253,291A patent/CA1074312A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-03-25	MKEX	Expiry

Publication	Publication Date	Title
US4044053A (en)	1977-08-23	Preparation of polyalkylene polyamines
US4036881A (en)	1977-07-19	Preparation of polyalkylene polyamines
US4394524A (en)	1983-07-19	Preparation of polyalkylene polyamines from ammonia, alkyleneamine, and alkanolamine
US4448997A (en)	1984-05-15	Preparation of linear polyethylenepolyamines with an aluminum phosphate catalyst
US4103087A (en)	1978-07-25	Production of di-(N,N-disubstituted amino) alkanes
CA1078381A (fr)	1980-05-27	Production de bis-(morpholino-n-alkyl) ethers
US4605770A (en)	1986-08-12	Noncyclic polyalkylene polyamines by the reaction of an alkanolamine compound and an alkyleneamine compound in the presence of a Group IIA or Group IIIB metal acid phosphate catalyst
EP0256516A2 (fr)	1988-02-24	Procédé pour la fabrication d'alcoylèneamines
CA1112657A (fr)	1981-11-17	Procede de fabrication de silanes aminoalkyles
CA1070309A (fr)	1980-01-22	Preparation de la n-(aminoalkyl) piperazine
US3005010A (en)	1961-10-17	Method for preparing dihydrocarbyloxyphosphinyl formamides
US4117227A (en)	1978-09-26	Production of n-(substituted) morpholine
GB2316945A (en)	1998-03-11	Preparation of 3-amino-1-hydroxypropane-1,1-diphosphonic acid from N-protected beta-alanine using phosphorous acid and a phosphorus chloride
EP0078000B1 (fr)	1986-05-28	Procédé pour la préparation d'allylamines à partir d'allyl alcool
CA1228449A (fr)	1987-10-20	Preparation de polyamines de polyalkylene
US4931585A (en)	1990-06-05	Process for preparing N-phosphono-methyl-imino-diacetic acid
US4092316A (en)	1978-05-30	Synthesis of C-alkyl-triethylenediamines
CA1070305A (fr)	1980-01-22	Methode pour la production de derives de la morpholine
CA1074317A (fr)	1980-03-25	Production d'un compose a base de n-piperazine substituee
CA1092114A (fr)	1980-12-23	Procede d'obtention de composes de la n-(radical substitue) morpholine
EP0093983B1 (fr)	1986-10-22	Préparation de polyalkylène-polyamines en présence d'un catalyseur du type phosphoreamide
CA1074314A (fr)	1980-03-25	Preparation d'un compose a base de morpholine
NO761856L (fr)	1976-12-03
CA1078382A (fr)	1980-05-27	Production de composes bis-(n,n-amino disubstitue)
US4066649A (en)	1978-01-03	Method of producing n,n'-(dimethyl) piperazine compounds