DD149510A5 - Verfahren zur herstellung von methylaminen - Google Patents

Verfahren zur herstellung von methylaminen Download PDF

Info

Publication number: DD149510A5
Authority: DD; German Democratic Republic
Prior art keywords: methanol; catalyst; ammonia; weight; methylamines
Prior art date: 1979-03-23

Application number

DD80219796A

Other languages

German (de)

English (en)

Inventor

Jean Ramioulle

Guy Schmitz

Pol Lambert

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

1980-03-20

Publication date

1981-07-15

1980-03-20 Application filed by Ucb Sa filed Critical Ucb Sa

1981-07-15 Publication of DD149510A5 publication Critical patent/DD149510A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 22
150000003956 methylamines Chemical class 0.000 title claims abstract description 12
238000004519 manufacturing process Methods 0.000 title description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 87
239000003054 catalyst Substances 0.000 claims abstract description 39
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 30
229910021529 ammonia Inorganic materials 0.000 claims abstract description 15
239000000203 mixture Substances 0.000 claims abstract description 13
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 claims abstract description 11
238000002360 preparation method Methods 0.000 claims abstract description 8
239000002253 acid Substances 0.000 claims abstract description 6
239000012808 vapor phase Substances 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 17
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 13
239000011541 reaction mixture Substances 0.000 abstract 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 9
239000007789 gas Substances 0.000 description 9
229910052901 montmorillonite Inorganic materials 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 8
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
-1 silicitic oxide Chemical compound 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
239000004927 clay Substances 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
229910052500 inorganic mineral Inorganic materials 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
239000002994 raw material Substances 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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
229910000323 aluminium silicate Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000000470 constituent Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
HLLSOEKIMZEGFV-UHFFFAOYSA-N 4-(dibutylsulfamoyl)benzoic acid Chemical compound CCCCN(CCCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 HLLSOEKIMZEGFV-UHFFFAOYSA-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
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
238000001994 activation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 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
239000011449 brick Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000007036 catalytic synthesis reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
INPLXZPZQSLHBR-UHFFFAOYSA-N cobalt(2+);sulfide Chemical compound [S-2].[Co+2] INPLXZPZQSLHBR-UHFFFAOYSA-N 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 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
229910000388 diammonium phosphate Inorganic materials 0.000 description 1
235000019838 diammonium phosphate Nutrition 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000010433 feldspar Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000000732 glass refractive index measurement Methods 0.000 description 1
229910000271 hectorite Inorganic materials 0.000 description 1
KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000002687 intercalation Effects 0.000 description 1
238000009830 intercalation Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 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
229930014626 natural product Natural products 0.000 description 1
QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
229910000273 nontronite Inorganic materials 0.000 description 1
238000011017 operating method Methods 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 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
239000003208 petroleum Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000011148 porous material Substances 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
229910052702 rhenium Inorganic materials 0.000 description 1
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-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
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
FJOLTQXXWSRAIX-UHFFFAOYSA-K silver phosphate Chemical compound [Ag+].[Ag+].[Ag+].[O-]P([O-])([O-])=O FJOLTQXXWSRAIX-UHFFFAOYSA-K 0.000 description 1
229910000161 silver phosphate Inorganic materials 0.000 description 1
229940019931 silver phosphate Drugs 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
229910003452 thorium oxide Inorganic materials 0.000 description 1
RUJLHPZAKCVICY-UHFFFAOYSA-J thorium(4+);disulfate Chemical compound [Th+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUJLHPZAKCVICY-UHFFFAOYSA-J 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
229910001928 zirconium oxide Inorganic materials 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)

DD80219796A 1979-03-23 1980-03-20 Verfahren zur herstellung von methylaminen DD149510A5 (de)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
DD149510A5 true DD149510A5 (de)	1981-07-15

Family

ID=10504093

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80219796A DD149510A5 (de)	1979-03-23	1980-03-20	Verfahren zur herstellung von methylaminen

Country Status (13)

Country	Link
JP (1)	JPS55129246A (fr)
BE (1)	BE882332A (fr)
BR (1)	BR8001725A (fr)
CA (1)	CA1129888A (fr)
DD (1)	DD149510A5 (fr)
DE (1)	DE3010791A1 (fr)
ES (1)	ES489771A0 (fr)
FR (1)	FR2451909A1 (fr)
GB (1)	GB2045232B (fr)
IN (1)	IN151294B (fr)
IT (1)	IT8048227A0 (fr)
NL (1)	NL8001612A (fr)
ZA (1)	ZA801658B (fr)

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
DE3564102D1 (en) *	1984-11-07	1988-09-08	Air Prod & Chem	Amines via the amination of alkanols using dealuminated zeolites

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 IN IN319/CAL/80A patent/IN151294B/en unknown
- 1980-03-20 BE BE1/9753A patent/BE882332A/fr not_active IP Right Cessation
- 1980-03-20 DD DD80219796A patent/DD149510A5/de unknown
- 1980-03-20 DE DE19803010791 patent/DE3010791A1/de not_active Withdrawn
- 1980-03-21 IT IT8048227A patent/IT8048227A0/it unknown
- 1980-03-21 CA CA348,201A patent/CA1129888A/fr not_active Expired
- 1980-03-21 ES ES489771A patent/ES489771A0/es active Granted
- 1980-03-21 ZA ZA00801658A patent/ZA801658B/xx unknown
- 1980-03-21 BR BR8001725A patent/BR8001725A/pt unknown
- 1980-03-21 FR FR8006451A patent/FR2451909A1/fr not_active Withdrawn
- 1980-03-22 JP JP3683480A patent/JPS55129246A/ja active Pending

Also Published As

Publication number	Publication date
GB2045232B (en)	1983-03-30
NL8001612A (nl)	1980-09-25
FR2451909A1 (fr)	1980-10-17
JPS55129246A (en)	1980-10-06
CA1129888A (fr)	1982-08-17
ES8103017A1 (es)	1981-02-16
ES489771A0 (es)	1981-02-16
BE882332A (fr)	1980-09-22
BR8001725A (pt)	1980-11-18
DE3010791A1 (de)	1980-10-02
GB2045232A (en)	1980-10-29
IT8048227A0 (it)	1980-03-21
IN151294B (fr)	1983-03-26
ZA801658B (en)	1981-03-25

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