CA1129888A - Process for the manufacture of methylamines - Google Patents

Process for the manufacture of methylamines

Info

Publication number: CA1129888A
Authority: CA; Canada
Prior art keywords: methanol; catalyst; ammonia; methylamines; dma
Prior art date: 1979-03-23
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

CA348,201A

Other languages

English (en)

French (fr)

Inventor

Jean Ramioulle

Guy Schmitz

Pol Lambert

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.)

UCB SA

Original Assignee

UCB SA

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.)

1979-03-23

Filing date

1980-03-21

Publication date

1982-08-17

1980-03-21 Application filed by UCB SA filed Critical UCB SA

1982-08-17 Application granted granted Critical

1982-08-17 Publication of CA1129888A publication Critical patent/CA1129888A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 22
238000004519 manufacturing process Methods 0.000 title claims abstract description 10
150000003956 methylamines Chemical class 0.000 title claims abstract description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 90
239000003054 catalyst Substances 0.000 claims abstract description 37
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 28
238000006243 chemical reaction Methods 0.000 claims abstract description 16
229910021529 ammonia Inorganic materials 0.000 claims abstract description 14
239000002253 acid Substances 0.000 claims abstract description 9
239000000203 mixture Substances 0.000 claims description 8
239000012808 vapor phase Substances 0.000 claims description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract description 28
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical class O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 abstract description 8
150000001412 amines Chemical class 0.000 abstract description 6
229910052901 montmorillonite Inorganic materials 0.000 description 9
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
229910052782 aluminium Inorganic materials 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
-1 zirconiurn Chemical compound 0.000 description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
239000004927 clay Substances 0.000 description 3
239000008246 gaseous mixture Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 3
239000011707 mineral Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000012876 carrier material Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
210000005053 lamin Anatomy 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002994 raw material Substances 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
239000010703 silicon Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
241000905957 Channa melasoma Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
241000694408 Isomeris Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
241000135799 Thorius Species 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229940037003 alum Drugs 0.000 description 1
ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
238000007036 catalytic synthesis reaction Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
INPLXZPZQSLHBR-UHFFFAOYSA-N cobalt(2+);sulfide Chemical compound [S-2].[Co+2] INPLXZPZQSLHBR-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
230000002349 favourable effect Effects 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
239000011521 glass Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910000273 nontronite Inorganic materials 0.000 description 1
KSOCVFUBQIXVDC-FMQUCBEESA-N p-azophenyltrimethylammonium Chemical compound C1=CC([N+](C)(C)C)=CC=C1\N=N\C1=CC=C([N+](C)(C)C)C=C1 KSOCVFUBQIXVDC-FMQUCBEESA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
USBWXQYIYZPMMN-UHFFFAOYSA-N rhenium;heptasulfide Chemical compound [S-2].[S-2].[S-2].[S-2].[S-2].[S-2].[S-2].[Re].[Re] USBWXQYIYZPMMN-UHFFFAOYSA-N 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000010959 steel Substances 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000010457 zeolite Substances 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/16—Clays or other mineral silicates

Landscapes

Chemical & Material Sciences (AREA)
Dispersion Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

CA348,201A 1979-03-23 1980-03-21 Process for the manufacture of methylamines Expired CA1129888A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7910300		1979-03-23
GB7910300A GB2045232B (en)	1979-03-23	1979-03-23	Manufacture of methylamines

Publications (1)

Publication Number	Publication Date
CA1129888A true CA1129888A (en)	1982-08-17

Family

ID=10504093

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA348,201A Expired CA1129888A (en)	1979-03-23	1980-03-21	Process for the manufacture of methylamines

Country Status (13)

Country	Link
JP (1)	JPS55129246A (de)
BE (1)	BE882332A (de)
BR (1)	BR8001725A (de)
CA (1)	CA1129888A (de)
DD (1)	DD149510A5 (de)
DE (1)	DE3010791A1 (de)
ES (1)	ES8103017A1 (de)
FR (1)	FR2451909A1 (de)
GB (1)	GB2045232B (de)
IN (1)	IN151294B (de)
IT (1)	IT8048227A0 (de)
NL (1)	NL8001612A (de)
ZA (1)	ZA801658B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4458092A (en) *	1982-01-29	1984-07-03	Air Products And Chemicals, Inc.	Highly active catalysts for methanol amination
EP0180983B1 (de) *	1984-11-07	1988-08-03	Air Products And Chemicals, Inc.	Herstellung von Aminen durch Aminierung von Alkanolen unter Verwendung von dealuminierten Zeolithen

1979
- 1979-03-23 GB GB7910300A patent/GB2045232B/en not_active Expired
1980
- 1980-03-18 NL NL8001612A patent/NL8001612A/nl not_active Application Discontinuation
- 1980-03-20 DD DD80219796A patent/DD149510A5/de unknown
- 1980-03-20 DE DE19803010791 patent/DE3010791A1/de not_active Withdrawn
- 1980-03-20 BE BE1/9753A patent/BE882332A/fr not_active IP Right Cessation
- 1980-03-20 IN IN319/CAL/80A patent/IN151294B/en unknown
- 1980-03-21 BR BR8001725A patent/BR8001725A/pt unknown
- 1980-03-21 ZA ZA00801658A patent/ZA801658B/xx unknown
- 1980-03-21 CA CA348,201A patent/CA1129888A/en not_active Expired
- 1980-03-21 IT IT8048227A patent/IT8048227A0/it unknown
- 1980-03-21 FR FR8006451A patent/FR2451909A1/fr not_active Withdrawn
- 1980-03-21 ES ES489771A patent/ES8103017A1/es not_active Expired
- 1980-03-22 JP JP3683480A patent/JPS55129246A/ja active Pending

Also Published As

Publication number	Publication date
BE882332A (fr)	1980-09-22
JPS55129246A (en)	1980-10-06
BR8001725A (pt)	1980-11-18
GB2045232B (en)	1983-03-30
NL8001612A (nl)	1980-09-25
IT8048227A0 (it)	1980-03-21
IN151294B (de)	1983-03-26
DD149510A5 (de)	1981-07-15
FR2451909A1 (fr)	1980-10-17
ES489771A0 (es)	1981-02-16
ES8103017A1 (es)	1981-02-16
DE3010791A1 (de)	1980-10-02
GB2045232A (en)	1980-10-29
ZA801658B (en)	1981-03-25

Legal Events

Date	Code	Title	Description
1999-08-17	MKEX	Expiry

Publication	Publication Date	Title
EP0133938B1 (de)	1986-11-05	Verfahren zur Herstellung von Aminen
JPS6325575B2 (de)	1988-05-26
GB1579159A (en)	1980-11-12	Manufacture of alkanols
JP4159630B2 (ja)	2008-10-01	Ｎ−置換された環式アミンの製法
KR20230126219A (ko)	2023-08-29	1-헥센의 정제 방법
US4777322A (en)	1988-10-11	Obtaining but-2-enes from C4 -hydrocarbon mixtures which contain but-1-ene and may or may not contain but-2-enes
CA1135939A (en)	1982-11-23	Preparation of dimethylamine
EP0036547B2 (de)	1987-12-02	Katalytisches Verfahren zur Herstellung von Alkylaminen und für dieses Verfahren geeignetes Katalysatorsystem
KR20060054397A (ko)	2006-05-22	에틸렌아민의 제조 방법
EP0469719A1 (de)	1992-02-05	Alkylaminsynthese in Gegenwart von Montmorillonittonen
JPH11508918A (ja)	1999-08-03	キノリン塩基の製造方法
CN100357254C (zh)	2007-12-26	胺化反应方法
CA2069389A1 (en)	1993-04-26	One step synthesis of methyl t-butyl ether from t-butanol using fluorosulfonic acid-modified clay catalysts
GB2045232A (en)	1980-10-29	Manufacture of methylamines
JPS6325576B2 (de)	1988-05-26
JPH0748303A (ja)	1995-02-21	β−ゼオライト触媒を使用するエチル−ｔｅｒｔ−ブチルエーテルの合成方法
EP0308552A1 (de)	1989-03-29	Verfahren zur Herstellung von Diphenylamin
EP1644304A2 (de)	2006-04-12	Verfahren zur herstellung von alkylbenzol
AU2004256092B2 (en)	2007-09-13	Hydrocracking of diphenylalkanes
US4291181A (en)	1981-09-22	Indenes from tetrahydroindenes
US4115463A (en)	1978-09-19	Production of cycloalkylaromatics
EP1010682B1 (de)	2003-08-06	Verfahren zur Herstellung von Isobutylenglycol
WO1999002483A1 (en)	1999-01-21	Method of making methylamines using chabazite catalysts
JPH0656726A (ja)	1994-03-01	リン酸で改質された粘土触媒を使用するアルキル第三級アルキルエーテルの合成
EP0521699B1 (de)	1998-08-12	Herstellung von Alkyl Tert-Alkyl Ethern durch Verwendung von Tonkatalysatoren