NO131458B - - Google Patents

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Info

Publication number: NO131458B
Authority: NO; Norway
Prior art keywords: lead; bromide; water; tel; alkyl
Prior art date: 1968-11-04

Application number

NO4274/69A

Other languages

English (en)

Norwegian (no)

Other versions

NO131458C (de

Inventor

K Yang

J D Reedy

M A Johnson

W H Harwood

Original Assignee

Continental Oil Co

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.)

1968-11-04

Filing date

1969-10-28

Publication date

1975-02-24

1969-10-28 Application filed by Continental Oil Co filed Critical Continental Oil Co

1975-02-24 Publication of NO131458B publication Critical patent/NO131458B/no

1975-06-04 Publication of NO131458C publication Critical patent/NO131458C/no

Links

XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
238000000034 method Methods 0.000 claims description 40
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 35
239000000203 mixture Substances 0.000 claims description 30
239000002904 solvent Substances 0.000 claims description 22
238000004519 manufacturing process Methods 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
150000001347 alkyl bromides Chemical class 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
150000002611 lead compounds Chemical class 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 7
RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 claims description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
238000004090 dissolution Methods 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
238000005192 partition Methods 0.000 claims description 3
230000001737 promoting effect Effects 0.000 claims description 3
125000005207 tetraalkylammonium group Chemical group 0.000 claims description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 96
238000005868 electrolysis reaction Methods 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
XOOGZRUBTYCLHG-UHFFFAOYSA-N tetramethyllead Chemical compound C[Pb](C)(C)C XOOGZRUBTYCLHG-UHFFFAOYSA-N 0.000 description 14
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 13
239000000047 product Substances 0.000 description 13
210000004027 cell Anatomy 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000000010 aprotic solvent Substances 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
230000007306 turnover Effects 0.000 description 8
229940102396 methyl bromide Drugs 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
239000005977 Ethylene Substances 0.000 description 5
-1 alkyl lead compounds Chemical class 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
150000001350 alkyl halides Chemical class 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000003792 electrolyte Substances 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
239000012528 membrane Substances 0.000 description 4
SMHNCYOTIYFOKL-UHFFFAOYSA-N tetrapropylplumbane Chemical compound CCC[Pb](CCC)(CCC)CCC SMHNCYOTIYFOKL-UHFFFAOYSA-N 0.000 description 4
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 3
GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
239000001099 ammonium carbonate Substances 0.000 description 3
235000012501 ammonium carbonate Nutrition 0.000 description 3
239000003011 anion exchange membrane Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000008901 benefit Effects 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000000446 fuel Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 3
PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
239000005018 casein Substances 0.000 description 2
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
235000021240 caseins Nutrition 0.000 description 2
230000005611 electricity Effects 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
201000001997 microphthalmia with limb anomalies Diseases 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000001256 steam distillation Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
229920000298 Cellophane Polymers 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
239000006079 antiknock agent Substances 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000007872 degassing Methods 0.000 description 1
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
VLZZXGOEDAYHOI-UHFFFAOYSA-N ethyllead Chemical compound CC[Pb] VLZZXGOEDAYHOI-UHFFFAOYSA-N 0.000 description 1
238000004880 explosion Methods 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
235000019988 mead Nutrition 0.000 description 1
VRGUHZVPXCABAX-UHFFFAOYSA-N methyllead Chemical compound [Pb]C VRGUHZVPXCABAX-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000008447 perception Effects 0.000 description 1
125000005496 phosphonium group Chemical group 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
229910052573 porcelain Inorganic materials 0.000 description 1
238000011027 product recovery Methods 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
KGFRUGHBHNUHOS-UHFFFAOYSA-N triethyl(methyl)plumbane Chemical compound CC[Pb](C)(CC)CC KGFRUGHBHNUHOS-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000011800 void material Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/13—Organo-metallic compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Electrochemistry (AREA)
Materials Engineering (AREA)
Metallurgy (AREA)
Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)

NO4274/69A 1968-11-04 1969-10-28 NO131458C (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US77332168A	1968-11-04	1968-11-04
US86309669A	1969-10-02	1969-10-02

Publications (2)

Publication Number	Publication Date
NO131458B true NO131458B (de)	1975-02-24
NO131458C NO131458C (de)	1975-06-04

Family

ID=27118737

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO4274/69A NO131458C (de)	1968-11-04	1969-10-28

Country Status (13)

Country	Link
US (1)	US3649482A (de)
AT (1)	AT299972B (de)
BE (1)	BE741249A (de)
CA (1)	CA960999A (de)
CH (1)	CH510056A (de)
DE (1)	DE1955201A1 (de)
ES (1)	ES373470A1 (de)
FR (1)	FR2022554A1 (de)
GB (1)	GB1285209A (de)
LU (1)	LU59753A1 (de)
NL (1)	NL6916616A (de)
NO (1)	NO131458C (de)
SU (1)	SU471724A3 (de)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6428676B1 (en)	2000-11-08	2002-08-06	Enthone Inc.	Process for producing low alpha lead methane sulfonate
US8313634B2 (en)	2009-01-29	2012-11-20	Princeton University	Conversion of carbon dioxide to organic products
US8500987B2 (en)	2010-03-19	2013-08-06	Liquid Light, Inc.	Purification of carbon dioxide from a mixture of gases
US8721866B2 (en)	2010-03-19	2014-05-13	Liquid Light, Inc.	Electrochemical production of synthesis gas from carbon dioxide
US8845877B2 (en)	2010-03-19	2014-09-30	Liquid Light, Inc.	Heterocycle catalyzed electrochemical process
US8845878B2 (en)	2010-07-29	2014-09-30	Liquid Light, Inc.	Reducing carbon dioxide to products
US8961774B2 (en)	2010-11-30	2015-02-24	Liquid Light, Inc.	Electrochemical production of butanol from carbon dioxide and water
US8568581B2 (en)	2010-11-30	2013-10-29	Liquid Light, Inc.	Heterocycle catalyzed carbonylation and hydroformylation with carbon dioxide
US9090976B2 (en)	2010-12-30	2015-07-28	The Trustees Of Princeton University	Advanced aromatic amine heterocyclic catalysts for carbon dioxide reduction
US10329676B2 (en)	2012-07-26	2019-06-25	Avantium Knowledge Centre B.V.	Method and system for electrochemical reduction of carbon dioxide employing a gas diffusion electrode
US9175407B2 (en)	2012-07-26	2015-11-03	Liquid Light, Inc.	Integrated process for producing carboxylic acids from carbon dioxide
US8641885B2 (en)	2012-07-26	2014-02-04	Liquid Light, Inc.	Multiphase electrochemical reduction of CO2
US8845875B2 (en)	2012-07-26	2014-09-30	Liquid Light, Inc.	Electrochemical reduction of CO2 with co-oxidation of an alcohol
US8858777B2 (en)	2012-07-26	2014-10-14	Liquid Light, Inc.	Process and high surface area electrodes for the electrochemical reduction of carbon dioxide
WO2014043651A2 (en)	2012-09-14	2014-03-20	Liquid Light, Inc.	High pressure electrochemical cell and process for the electrochemical reduction of carbon dioxide
BR112015006212A2 (pt) *	2012-09-19	2017-07-04	Liquid Light Inc	co-produção eletroquímica de produtos químicos empregando a reciclagem de um haleto de hidrogênio

1969
- 1969-10-02 US US863096A patent/US3649482A/en not_active Expired - Lifetime
- 1969-10-23 CA CA065,574A patent/CA960999A/en not_active Expired
- 1969-10-28 NO NO4274/69A patent/NO131458C/no unknown
- 1969-11-03 DE DE19691955201 patent/DE1955201A1/de active Pending
- 1969-11-03 AT AT1029069A patent/AT299972B/de not_active IP Right Cessation
- 1969-11-04 BE BE741249D patent/BE741249A/xx unknown
- 1969-11-04 GB GB53911/69A patent/GB1285209A/en not_active Expired
- 1969-11-04 FR FR6937898A patent/FR2022554A1/fr not_active Withdrawn
- 1969-11-04 LU LU59753D patent/LU59753A1/xx unknown
- 1969-11-04 NL NL6916616A patent/NL6916616A/xx unknown
- 1969-11-04 CH CH1640669A patent/CH510056A/fr not_active IP Right Cessation
- 1969-11-04 SU SU1376454A patent/SU471724A3/ru active
- 1969-11-04 ES ES373470A patent/ES373470A1/es not_active Expired

Also Published As

Publication number	Publication date
CH510056A (fr)	1971-07-15
GB1285209A (en)	1972-08-16
LU59753A1 (de)	1970-01-13
BE741249A (de)	1970-05-04
NO131458C (de)	1975-06-04
NL6916616A (de)	1970-05-08
ES373470A1 (es)	1972-01-16
CA960999A (en)	1975-01-14
SU471724A3 (ru)	1975-05-25
US3649482A (en)	1972-03-14
DE1955201A1 (de)	1970-05-27
FR2022554A1 (de)	1970-07-31
AT299972B (de)	1972-07-10

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US4216066A (en)	1980-08-05	Preparation of tetramethyltin from a magnesium-tin alloy
US3622476A (en)	1971-11-23	Cathodic process for the preparation of tetraalkyl lead compounds