CA1084925A - Preparation industrielle et emploi d'acides aminodi- et polyalkylamidoalcane - Google Patents

Preparation industrielle et emploi d'acides aminodi- et polyalkylamidoalcane

Info

Publication number: CA1084925A
Authority: CA; Canada
Prior art keywords: alkyl; carbon atoms; hydrogen; compound according; magnesium
Prior art date: 1975-12-19
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

CA268,188A

Other languages

English (en)

Inventor

Robert E.A. Dear

Eduard K. Kleiner

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.)

Novartis AG

Original Assignee

Ciba Geigy AG

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.)

1975-12-19

Filing date

1976-12-17

Publication date

1980-09-02

1976-12-17 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1980-09-02 Application granted granted Critical

1980-09-02 Publication of CA1084925A publication Critical patent/CA1084925A/fr

Status Expired legal-status Critical Current

Links

150000003460 sulfonic acids Chemical class 0.000 title claims abstract description 7
238000000034 method Methods 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title claims description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
150000001875 compounds Chemical class 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
239000001257 hydrogen Substances 0.000 claims abstract description 16
239000002585 base Substances 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 10
150000001412 amines Chemical class 0.000 claims abstract description 9
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
150000001340 alkali metals Chemical class 0.000 claims abstract description 7
150000003141 primary amines Chemical class 0.000 claims abstract description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 5
150000007530 organic bases Chemical class 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
125000002757 morpholinyl group Chemical group 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 5
125000004076 pyridyl group Chemical group 0.000 claims abstract 2
-1 furfuryl Chemical group 0.000 claims description 12
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 10
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 10
229910052749 magnesium Chemical group 0.000 claims description 10
239000011777 magnesium Chemical group 0.000 claims description 10
229910052700 potassium Inorganic materials 0.000 claims description 10
239000011591 potassium Chemical group 0.000 claims description 10
PYDQYQSHPJGKNR-UHFFFAOYSA-N 2-methyl-2-(propanoylamino)propane-1-sulfonic acid Chemical compound CCC(=O)NC(C)(C)CS(O)(=O)=O PYDQYQSHPJGKNR-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
239000011734 sodium Chemical group 0.000 claims description 5
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
238000006555 catalytic reaction Methods 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
230000001131 transforming effect Effects 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 7
125000003118 aryl group Chemical group 0.000 abstract description 2
125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
239000004094 surface-active agent Substances 0.000 abstract description 2
238000007259 addition reaction Methods 0.000 abstract 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
229940051250 hexylene glycol Drugs 0.000 description 3
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
239000000376 reactant Substances 0.000 description 3
IAUGBVWVWDTCJV-UHFFFAOYSA-N 1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CCC(S(O)(=O)=O)NC(=O)C=C IAUGBVWVWDTCJV-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
235000001465 calcium Nutrition 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229960005069 calcium Drugs 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
229940093476 ethylene glycol Drugs 0.000 description 2
238000005187 foaming Methods 0.000 description 2
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 2
239000008233 hard water Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
RWLPNKXCEUMHBL-UHFFFAOYSA-N n-tert-butylpropanamide Chemical compound CCC(=O)NC(C)(C)C RWLPNKXCEUMHBL-UHFFFAOYSA-N 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000003352 sequestering agent Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
MARCAKLHFUYDJE-UHFFFAOYSA-N 1,2-xylene;hydrate Chemical compound O.CC1=CC=CC=C1C MARCAKLHFUYDJE-UHFFFAOYSA-N 0.000 description 1
OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DSIGYWYKUCPBAF-UHFFFAOYSA-N 1-(prop-2-enoylamino)butane-1-sulfonic acid Chemical compound CCCC(S(O)(=O)=O)NC(=O)C=C DSIGYWYKUCPBAF-UHFFFAOYSA-N 0.000 description 1
VMRZUHSTSZRINS-UHFFFAOYSA-N 1-[2-(prop-2-enoylamino)-1h-pyridin-2-yl]ethanesulfonic acid Chemical compound C=CC(=O)NC1(C(C)S(O)(=O)=O)NC=CC=C1 VMRZUHSTSZRINS-UHFFFAOYSA-N 0.000 description 1
CKYXMHQMAFHFKC-UHFFFAOYSA-N 1-[6-methyl-1-(prop-2-enoylamino)cyclohexa-2,4-dien-1-yl]ethanesulfonic acid Chemical compound C=CC(=O)NC1(C(C)S(O)(=O)=O)C=CC=CC1C CKYXMHQMAFHFKC-UHFFFAOYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
BKXMAQXSDYWIPT-UHFFFAOYSA-N 2,2-diethylpropane-1,3-diol;[4-(hydroxymethyl)cyclohexyl]methanol Chemical compound CCC(CC)(CO)CO.OCC1CCC(CO)CC1 BKXMAQXSDYWIPT-UHFFFAOYSA-N 0.000 description 1
AKEGTQKKWUFLBQ-UHFFFAOYSA-N 2,4,4-trimethyl-2-(prop-2-enoylamino)pentane-1-sulfonic acid Chemical compound CC(C)(C)CC(C)(CS(O)(=O)=O)NC(=O)C=C AKEGTQKKWUFLBQ-UHFFFAOYSA-N 0.000 description 1
KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
MVYVKSBVZFBBPL-UHFFFAOYSA-N 2-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(C)NC(=O)C=C MVYVKSBVZFBBPL-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
NRVQUYCYEAKQIF-UHFFFAOYSA-N 2-phenyl-2-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound C=CC(=O)NC(CS(O)(=O)=O)(C)C1=CC=CC=C1 NRVQUYCYEAKQIF-UHFFFAOYSA-N 0.000 description 1
NUNAWQZKZVVELQ-UHFFFAOYSA-N 3-amino-4-methylphenol Chemical compound CC1=CC=C(O)C=C1N NUNAWQZKZVVELQ-UHFFFAOYSA-N 0.000 description 1
DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
101100404567 Drosophila melanogaster nesd gene Proteins 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000003974 aralkylamines Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
102220355412 c.74T>A Human genes 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
125000002704 decyl group Chemical group [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])* 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
239000003317 industrial substance Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
XMMDVXFQGOEOKH-UHFFFAOYSA-N n'-dodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCN XMMDVXFQGOEOKH-UHFFFAOYSA-N 0.000 description 1
QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
ANORDWOIBSUYBN-UHFFFAOYSA-N n-chloro-1-phenylmethanamine Chemical compound ClNCC1=CC=CC=C1 ANORDWOIBSUYBN-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
235000007686 potassium Nutrition 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 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
239000013535 sea water Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
XVCDQXABFKLFCH-UHFFFAOYSA-M sodium;n-prop-2-enoylsulfamate Chemical compound [Na+].[O-]S(=O)(=O)NC(=O)C=C XVCDQXABFKLFCH-UHFFFAOYSA-M 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Detergent Compositions (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA268,188A 1975-12-19 1976-12-17 Preparation industrielle et emploi d'acides aminodi- et polyalkylamidoalcane Expired CA1084925A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US64226975A	1975-12-19	1975-12-19
US642,269		1975-12-19

Publications (1)

Publication Number	Publication Date
CA1084925A true CA1084925A (fr)	1980-09-02

Family

ID=24575891

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA268,188A Expired CA1084925A (fr)	1975-12-19	1976-12-17	Preparation industrielle et emploi d'acides aminodi- et polyalkylamidoalcane

Country Status (8)

Country	Link
BE (1)	BE849504A (fr)
CA (1)	CA1084925A (fr)
CH (1)	CH622502A5 (fr)
DE (1)	DE2656687A1 (fr)
FR (1)	FR2335498A1 (fr)
GB (1)	GB1550420A (fr)
IT (1)	IT1075226B (fr)
NL (1)	NL7614060A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
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US11021383B2 (en)	2017-08-30	2021-06-01	Ecolab Usa Inc.	Use of di-ionic compounds as corrosion inhibitors in a water system

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US6207637B1 (en) *	1998-10-23	2001-03-27	The Lubrizol Corporation	Disulfonated alkylamines as degreasers and hydrotropes
US6264399B1 (en)	1999-10-14	2001-07-24	The Lubrizol Corporation	Method to remediate soil using a surfactant of a salt of an acrylamidoalkanesulfonic acid-amine reaction product
US20010016622A1 (en) *	2000-02-09	2001-08-23	Rainer Blum	Sulfonic acid compounds, processes for the preparation thereof and use thereof
CN116396183B (zh)	2018-08-29	2025-08-08	埃科莱布美国股份有限公司	衍生自多胺的离子化合物、其组合物和其制备方法
CN112584910B (zh) *	2018-08-29	2023-03-14	埃科莱布美国股份有限公司	衍生自多胺的带多个电荷的离子化合物及其组合物和其作为反相破乳剂用于油气操作的用途
WO2020047181A1 (fr)	2018-08-29	2020-03-05	Ecolab Usa Inc.	Utilisation de composés ioniques à charges multiples dérivés de polyamines pour clarification d'eaux usées
US11084974B2 (en)	2018-08-29	2021-08-10	Championx Usa Inc.	Use of multiple charged cationic compounds derived from polyamines for clay stabilization in oil and gas operations
US11058111B2 (en)	2018-08-29	2021-07-13	Ecolab Usa Inc.	Use of multiple charged cationic compounds derived from primary amines or polyamines for microbial fouling control in a water system
WO2020160081A1 (fr)	2019-01-29	2020-08-06	Ecolab Usa Inc.	Utilisation de composés cationiques à base de sucre pour lutter contre l'encrassement microbien dans un réseau d'alimentation en eau
EP4520802B1 (fr)	2019-04-16	2026-06-17	Ecolab USA Inc.	Utilisation de composés cationiques à charges multiples dérivés de polyamines et leurs compositions pour lutter contre la corrosion dans un réseau d'alimentation en eau
CN113979899B (zh) *	2021-03-26	2022-07-29	山东大学	一种季铵盐磺酸型表面活性剂及其制备方法与应用
CN117756682B (zh) *	2023-12-19	2025-09-16	东营江源化工有限公司	一种油气田用表面活性剂及其制备方法

1976
- 1976-12-10 CH CH1557776A patent/CH622502A5/de not_active IP Right Cessation
- 1976-12-15 DE DE19762656687 patent/DE2656687A1/de not_active Ceased
- 1976-12-16 FR FR7637987A patent/FR2335498A1/fr active Granted
- 1976-12-16 IT IT52636/76A patent/IT1075226B/it active
- 1976-12-16 GB GB52600/76A patent/GB1550420A/en not_active Expired
- 1976-12-17 NL NL7614060A patent/NL7614060A/xx active Search and Examination
- 1976-12-17 CA CA268,188A patent/CA1084925A/fr not_active Expired
- 1976-12-17 BE BE173346A patent/BE849504A/fr not_active IP Right Cessation

Cited By (4)

* Cited by examiner, † Cited by third party
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US11021383B2 (en)	2017-08-30	2021-06-01	Ecolab Usa Inc.	Use of di-ionic compounds as corrosion inhibitors in a water system
US11261113B2 (en)	2017-08-30	2022-03-01	Ecolab Usa Inc.	Molecules having one hydrophobic group and two identical hydrophilic ionic groups and compositions thereof and methods of preparation thereof
US11565958B2 (en)	2017-08-30	2023-01-31	Ecolab Usa Inc.	Use of di-ionic compounds as corrosion inhibitors in a water system
US12103881B2 (en)	2017-08-30	2024-10-01	Ecolab Usa Inc.	Molecules having one hydrophobic group and two identical hydrophilic ionic groups and compositions thereof and methods of preparation thereof

Also Published As

Publication number	Publication date
BE849504A (fr)	1977-06-17
DE2656687A1 (de)	1977-06-30
FR2335498B1 (fr)	1979-04-06
CH622502A5 (en)	1981-04-15
FR2335498A1 (fr)	1977-07-15
NL7614060A (nl)	1977-06-21
IT1075226B (it)	1985-04-22
GB1550420A (en)	1979-08-15

Legal Events

Date	Code	Title	Description
1997-09-02	MKEX	Expiry

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Dalinger et al.	2010	The specific reactivity of 3, 4, 5-trinitro-1H-pyrazole
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UA75598C2 (uk)	2006-05-15	Спосіб одержання анілінових сполук, проміжна сполука та її застосування
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JP6336579B2 (ja)	2018-06-06	ピリジン又はピラジン含有化合物
NO802356L (no)	1981-02-09	Funksjonelt substituerte fenoksyalkylalkoksysilaner og fremgangsmaate til deres fremstilling
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