ZA200400698B - In situ process for preparing quaternary ammonium bicarbonates and quaternary ammonium carbonates. - Google Patents

In situ process for preparing quaternary ammonium bicarbonates and quaternary ammonium carbonates. Download PDF

Info

Publication number: ZA200400698B
Authority: ZA; South Africa
Prior art keywords: alkyl; quaternary ammonium; carbonate; formula; amine
Prior art date: 2001-07-09

Application number

ZA200400698A

Other languages

English (en)

Inventor

Leigh E Walker

Original Assignee

Lonza 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.)

2001-07-09

Filing date

2004-01-28

Publication date

2004-10-15

2004-01-28 Application filed by Lonza Ag filed Critical Lonza Ag

2004-10-15 Publication of ZA200400698B publication Critical patent/ZA200400698B/en

Links

125000001453 quaternary ammonium group Chemical group 0.000 title claims description 52
239000001099 ammonium carbonate Substances 0.000 title claims description 25
235000012538 ammonium bicarbonate Nutrition 0.000 title claims description 13
235000011162 ammonium carbonates Nutrition 0.000 title description 14
238000011065 in-situ storage Methods 0.000 title description 5
238000004519 manufacturing process Methods 0.000 title description 5
238000000034 method Methods 0.000 claims description 78
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
125000000217 alkyl group Chemical group 0.000 claims description 53
229910052799 carbon Inorganic materials 0.000 claims description 28
150000001412 amines Chemical class 0.000 claims description 19
150000005676 cyclic carbonates Chemical class 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 14
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 11
150000002148 esters Chemical class 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
-1 alkyl methyl carbonate Chemical compound 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims description 8
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical group O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 8
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
229920003232 aliphatic polyester Polymers 0.000 claims description 7
JGFDZZLUDWMUQH-UHFFFAOYSA-N Didecyldimethylammonium Chemical compound CCCCCCCCCC[N+](C)(C)CCCCCCCCCC JGFDZZLUDWMUQH-UHFFFAOYSA-N 0.000 claims description 6
229940078672 didecyldimethylammonium Drugs 0.000 claims description 6
ATBNMWWDBWBAHM-UHFFFAOYSA-N n-decyl-n-methyldecan-1-amine Chemical compound CCCCCCCCCCN(C)CCCCCCCCCC ATBNMWWDBWBAHM-UHFFFAOYSA-N 0.000 claims description 6
239000004417 polycarbonate Substances 0.000 claims description 6
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 6
229920000515 polycarbonate Polymers 0.000 claims description 4
235000012501 ammonium carbonate Nutrition 0.000 claims description 3
VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 claims description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
YJLYANLCNIKXMG-UHFFFAOYSA-N N-Methyldioctylamine Chemical compound CCCCCCCCN(C)CCCCCCCC YJLYANLCNIKXMG-UHFFFAOYSA-N 0.000 claims description 2
NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 claims description 2
229950010007 dimantine Drugs 0.000 claims description 2
XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 2
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims 2
MVTVVKOMNZGDGD-UHFFFAOYSA-M didecyl(dimethyl)azanium;hydron;carbonate Chemical compound OC([O-])=O.CCCCCCCCCC[N+](C)(C)CCCCCCCCCC MVTVVKOMNZGDGD-UHFFFAOYSA-M 0.000 claims 2
YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
150000003512 tertiary amines Chemical class 0.000 description 5
235000011114 ammonium hydroxide Nutrition 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
238000002386 leaching Methods 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
238000005580 one pot reaction Methods 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
108010053481 Antifreeze Proteins Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 1
101100238304 Mus musculus Morc1 gene Proteins 0.000 description 1
125000005910 alkyl carbonate group Chemical group 0.000 description 1
PRKQVKDSMLBJBJ-UHFFFAOYSA-N ammonium carbonate Chemical class N.N.OC(O)=O PRKQVKDSMLBJBJ-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical group 0.000 description 1
230000002528 anti-freeze Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001944 continuous distillation Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
230000007423 decrease Effects 0.000 description 1
TXOJCSIIFFMREV-UHFFFAOYSA-L didecyl(dimethyl)azanium;carbonate Chemical compound [O-]C([O-])=O.CCCCCCCCCC[N+](C)(C)CCCCCCCCCC.CCCCCCCCCC[N+](C)(C)CCCCCCCCCC TXOJCSIIFFMREV-UHFFFAOYSA-L 0.000 description 1
229960004670 didecyldimethylammonium chloride Drugs 0.000 description 1
GUNDKLAGHABJDI-UHFFFAOYSA-N dimethyl carbonate;methanol Chemical compound OC.COC(=O)OC GUNDKLAGHABJDI-UHFFFAOYSA-N 0.000 description 1
OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
MELGLHXCBHKVJG-UHFFFAOYSA-N dimethyl(dioctyl)azanium Chemical compound CCCCCCCC[N+](C)(C)CCCCCCCC MELGLHXCBHKVJG-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
229910001510 metal chloride Inorganic materials 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
OMEMQVZNTDHENJ-UHFFFAOYSA-N n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCNC OMEMQVZNTDHENJ-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
GRNRCQKEBXQLAA-UHFFFAOYSA-M triethyl(2-hydroxyethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CCO GRNRCQKEBXQLAA-UHFFFAOYSA-M 0.000 description 1
PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/20—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of quaternary ammonium compounds

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

ZA200400698A 2001-07-09 2004-01-28 In situ process for preparing quaternary ammonium bicarbonates and quaternary ammonium carbonates. ZA200400698B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US30397101P	2001-07-09	2001-07-09

Publications (1)

Publication Number	Publication Date
ZA200400698B true ZA200400698B (en)	2004-10-15

Family

ID=23174485

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200400698A ZA200400698B (en)	2001-07-09	2004-01-28	In situ process for preparing quaternary ammonium bicarbonates and quaternary ammonium carbonates.

Country Status (21)

Country	Link
US (2)	US6784307B2 (de)
EP (1)	EP1406856B1 (de)
JP (1)	JP4326327B2 (de)
KR (1)	KR100886984B1 (de)
CN (1)	CN100396660C (de)
AT (1)	ATE466833T1 (de)
AU (1)	AU2002316559B2 (de)
BR (1)	BR0211229B1 (de)
CA (1)	CA2453391C (de)
DE (1)	DE60236286D1 (de)
ES (1)	ES2345141T3 (de)
HU (1)	HU230546B1 (de)
MX (1)	MX244518B (de)
NO (1)	NO333584B1 (de)
NZ (1)	NZ530911A (de)
PL (1)	PL205566B1 (de)
RU (1)	RU2299193C2 (de)
TW (1)	TWI242546B (de)
UA (1)	UA76478C2 (de)
WO (1)	WO2003006419A1 (de)
ZA (1)	ZA200400698B (de)

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CN103111324B (zh) *	2013-01-25	2014-12-17	中南大学	含溴或碘的卤素盐的应用和合成甲基三长链脂肪烃基季铵盐衍生物的方法
EP2984133B1 (de)	2013-04-08	2018-03-28	Allnex Netherlands B.V.	Zusammensetzung vernetzbar durch reale michael addition reaction (rma)
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JP6281280B2 (ja) *	2013-12-19	2018-02-21	東ソー株式会社	アロファネート・イソシアヌレート化触媒、該触媒を用いたポリイソシアネート組成物、該組成物の製造方法、及び該組成物を用いた二液型塗料組成物
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CA2983155C (en)	2015-04-17	2022-03-08	Allnex Netherlands B.V.	Modified epoxy primer for improved adhesion of rma crosslinkable coating compositions
JP6837991B2 (ja)	2015-04-17	2021-03-03	オールネックス・ネザーランズ・ビー．ブイ．ＡｌｌｎｅｘＮｅｔｈｅｒｌａｎｄｓＢ．Ｖ．	フロアコーティング組成物
CA2983148C (en)	2015-04-17	2023-05-09	Allnex Netherlands B.V.	Process for the manufacture of a crosslinkable composition
RU2720618C2 (ru)	2015-04-17	2020-05-12	Аллнекс Незерландс Б.В.	Способ отверждения rma-сшиваемого смоляного покрытия, rma-сшиваемые композиции и смолы для применения в указанном способе
CN104926668B (zh) *	2015-05-21	2018-02-27	北京盖雅环境科技有限公司	一种三长链烷基铵碳酸氢盐和碳酸盐的制备方法
IT201600130571A1 (it)	2016-12-23	2018-06-23	Lamberti Spa	Inibitori di idrati di gas
IT201600130556A1 (it)	2016-12-23	2018-06-23	Lamberti Spa	Inibitori di idrati di gas
CN107281994B (zh) *	2017-05-16	2019-08-27	天津大学	循环列管式反应器串联管式反应器制备四甲基碳酸氢铵的装置及方法
US11673976B2 (en)	2017-12-11	2023-06-13	Swimc Llc	Method for making water-dispersible and water-dispersed polymers
CN108440306B (zh) *	2018-05-24	2023-11-03	柏川新材料科技(宁波)有限公司	一种四甲基碳酸铵的绿色生产的设备及方法
EP3663326A1 (de)	2018-12-04	2020-06-10	Allnex Netherlands B.V.	Rma-vernetzbares polymer
KR102215414B1 (ko)	2020-07-07	2021-02-15	김상원	색상환
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CN116041187B (zh) *	2023-01-03	2025-06-06	烟台汉硅新材料科技有限公司	连续固定床催化反应原位制备混合甲胺碳酸盐的方法及其应用

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2002
- 2002-02-07 UA UA2004010608A patent/UA76478C2/uk unknown
- 2002-07-02 DE DE60236286T patent/DE60236286D1/de not_active Expired - Lifetime
- 2002-07-02 AU AU2002316559A patent/AU2002316559B2/en not_active Ceased
- 2002-07-02 JP JP2003512192A patent/JP4326327B2/ja not_active Expired - Fee Related
- 2002-07-02 HU HU0401230A patent/HU230546B1/hu not_active IP Right Cessation
- 2002-07-02 ES ES02746871T patent/ES2345141T3/es not_active Expired - Lifetime
- 2002-07-02 BR BRPI0211229-9A patent/BR0211229B1/pt not_active IP Right Cessation
- 2002-07-02 MX MXPA04000353 patent/MX244518B/es active IP Right Grant
- 2002-07-02 PL PL367612A patent/PL205566B1/pl unknown
- 2002-07-02 AT AT02746871T patent/ATE466833T1/de active
- 2002-07-02 WO PCT/US2002/021236 patent/WO2003006419A1/en not_active Ceased
- 2002-07-02 NZ NZ530911A patent/NZ530911A/en not_active IP Right Cessation
- 2002-07-02 US US10/188,692 patent/US6784307B2/en not_active Expired - Lifetime
- 2002-07-02 CA CA2453391A patent/CA2453391C/en not_active Expired - Fee Related
- 2002-07-02 CN CNB02802303XA patent/CN100396660C/zh not_active Expired - Fee Related
- 2002-07-02 RU RU2004104323/04A patent/RU2299193C2/ru not_active IP Right Cessation
- 2002-07-02 EP EP02746871A patent/EP1406856B1/de not_active Expired - Lifetime
- 2002-07-05 TW TW091114946A patent/TWI242546B/zh not_active IP Right Cessation
2003
- 2003-07-02 KR KR1020047000405A patent/KR100886984B1/ko not_active Expired - Fee Related
2004
- 2004-01-08 NO NO20040069A patent/NO333584B1/no not_active IP Right Cessation
- 2004-01-28 ZA ZA200400698A patent/ZA200400698B/en unknown
- 2004-02-10 US US10/776,368 patent/US6989459B2/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NZ530911A (en)	2005-07-29
US20040162343A1 (en)	2004-08-19
NO78493A (no)	2005-01-31
CN1464873A (zh)	2003-12-31
KR20040029363A (ko)	2004-04-06
EP1406856B1 (de)	2010-05-05
BR0211229B1 (pt)	2012-09-18
HUP0401230A2 (en)	2004-12-28
ES2345141T3 (es)	2010-09-16
US20030023108A1 (en)	2003-01-30
DE60236286D1 (de)	2010-06-17
TWI242546B (en)	2005-11-01
EP1406856A1 (de)	2004-04-14
RU2004104323A (ru)	2005-07-10
JP2004521953A (ja)	2004-07-22
CA2453391C (en)	2011-05-03
KR100886984B1 (ko)	2009-03-04
HU230546B1 (hu)	2016-11-28
UA76478C2 (uk)	2006-08-15
JP4326327B2 (ja)	2009-09-02
ATE466833T1 (de)	2010-05-15
NO333584B1 (no)	2013-07-15
CA2453391A1 (en)	2003-01-23
BR0211229A (pt)	2004-08-10
MXPA04000353A (es)	2005-09-08
MX244518B (es)	2007-03-28
PL205566B1 (pl)	2010-05-31
RU2299193C2 (ru)	2007-05-20
CN100396660C (zh)	2008-06-25
PL367612A1 (en)	2005-03-07
US6784307B2 (en)	2004-08-31
WO2003006419A1 (en)	2003-01-23
US6989459B2 (en)	2006-01-24
AU2002316559B2 (en)	2008-04-24
NO20040069L (no)	2004-03-05

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