ONIUM YLIDE CHEMISTRY. 1. BIFUNCTIONAL ACID-BASE-CATALYZED CONVERSION OF HETEROSUBSTITUTED METHANES INTO ETHYLENE AND DERIVED HYDROCARBONS. THE ONIUM YLIDE MECHANISM OF THE C1 yields C2 CONVERSION.

George A. Olah; Hans Doggweiler; Jeff D. Felberg; Stephan Frohlich; Mary Jo Grdina; Richard Karpeles; Takashi Keumi; Shin ichi Inaba; Wai M. Ip; Koop Lammertsma; George Salem; Derrick C. Tabor

ONIUM YLIDE CHEMISTRY. 1. BIFUNCTIONAL ACID-BASE-CATALYZED CONVERSION OF HETEROSUBSTITUTED METHANES INTO ETHYLENE AND DERIVED HYDROCARBONS. THE ONIUM YLIDE MECHANISM OF THE C₁ yields C₂ CONVERSION.

George A. Olah, Hans Doggweiler, Jeff D. Felberg, Stephan Frohlich, Mary Jo Grdina, Richard Karpeles, Takashi Keumi, Shin ichi Inaba, Wai M. Ip, Koop Lammertsma, George Salem, Derrick C. Tabor

Chemical Sciences

Research output: Contribution to journal › Article › peer-review

25 Citations (Scopus)

Abstract

The conversion of heterosubstituted methanes, such as methyl alcohol, dimethyl ether, methyl mercaptan, dimethyl sulfide, methylamines, and methyl halides, to ethylene and hydrocarbons derived thereof takes place over bifunctional acidic-basic-supported transition-metal oxide or oxyhalide catalysts, such as tungsten oxide supported on alumina, between 300 and 350 degree C. The conversion of methyl alcohol starts with bimolecular dehydration to dimethyl ether followed by acid-catalyzed transmethylation giving trimethyloxonium ion (or related catalyst-bound methyloxonium ion). The trimethyloxonium ion then undergoes base-induced deprotonation forming a catalyst surface-bound methylenedimethyloxonium ylide. Intermolecular methylation of the ylide, indicated by experiments using singly **1**3C-labeled dimethyl ether, gives methylethyloxonium ion thus providing the crucial first C-C bond.

Original language	English
Pages (from-to)	2134-2149
Number of pages	16
Journal	Journal of the American Chemical Society
Volume	106
Issue number	7
Publication status	Published - 1984

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Cite this

Olah, G. A., Doggweiler, H., Felberg, J. D., Frohlich, S., Grdina, M. J., Karpeles, R., Keumi, T., Inaba, S. I., Ip, W. M., Lammertsma, K., Salem, G., & Tabor, D. C. (1984). ONIUM YLIDE CHEMISTRY. 1. BIFUNCTIONAL ACID-BASE-CATALYZED CONVERSION OF HETEROSUBSTITUTED METHANES INTO ETHYLENE AND DERIVED HYDROCARBONS. THE ONIUM YLIDE MECHANISM OF THE C₁ yields C₂ CONVERSION. Journal of the American Chemical Society, 106(7), 2134-2149.

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title = "ONIUM YLIDE CHEMISTRY. 1. BIFUNCTIONAL ACID-BASE-CATALYZED CONVERSION OF HETEROSUBSTITUTED METHANES INTO ETHYLENE AND DERIVED HYDROCARBONS. THE ONIUM YLIDE MECHANISM OF THE C1 yields C2 CONVERSION.",

abstract = "The conversion of heterosubstituted methanes, such as methyl alcohol, dimethyl ether, methyl mercaptan, dimethyl sulfide, methylamines, and methyl halides, to ethylene and hydrocarbons derived thereof takes place over bifunctional acidic-basic-supported transition-metal oxide or oxyhalide catalysts, such as tungsten oxide supported on alumina, between 300 and 350 degree C. The conversion of methyl alcohol starts with bimolecular dehydration to dimethyl ether followed by acid-catalyzed transmethylation giving trimethyloxonium ion (or related catalyst-bound methyloxonium ion). The trimethyloxonium ion then undergoes base-induced deprotonation forming a catalyst surface-bound methylenedimethyloxonium ylide. Intermolecular methylation of the ylide, indicated by experiments using singly **1**3C-labeled dimethyl ether, gives methylethyloxonium ion thus providing the crucial first C-C bond.",

author = "Olah, {George A.} and Hans Doggweiler and Felberg, {Jeff D.} and Stephan Frohlich and Grdina, {Mary Jo} and Richard Karpeles and Takashi Keumi and Inaba, {Shin ichi} and Ip, {Wai M.} and Koop Lammertsma and George Salem and Tabor, {Derrick C.}",

year = "1984",

language = "English",

volume = "106",

pages = "2134--2149",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "7",

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Olah, GA, Doggweiler, H, Felberg, JD, Frohlich, S, Grdina, MJ, Karpeles, R, Keumi, T, Inaba, SI, Ip, WM, Lammertsma, K, Salem, G & Tabor, DC 1984, 'ONIUM YLIDE CHEMISTRY. 1. BIFUNCTIONAL ACID-BASE-CATALYZED CONVERSION OF HETEROSUBSTITUTED METHANES INTO ETHYLENE AND DERIVED HYDROCARBONS. THE ONIUM YLIDE MECHANISM OF THE C₁ yields C₂ CONVERSION.', Journal of the American Chemical Society, vol. 106, no. 7, pp. 2134-2149.

ONIUM YLIDE CHEMISTRY. 1. BIFUNCTIONAL ACID-BASE-CATALYZED CONVERSION OF HETEROSUBSTITUTED METHANES INTO ETHYLENE AND DERIVED HYDROCARBONS. THE ONIUM YLIDE MECHANISM OF THE C₁ yields C₂ CONVERSION. / Olah, George A.; Doggweiler, Hans; Felberg, Jeff D. et al.
In: Journal of the American Chemical Society, Vol. 106, No. 7, 1984, p. 2134-2149.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - ONIUM YLIDE CHEMISTRY. 1. BIFUNCTIONAL ACID-BASE-CATALYZED CONVERSION OF HETEROSUBSTITUTED METHANES INTO ETHYLENE AND DERIVED HYDROCARBONS. THE ONIUM YLIDE MECHANISM OF THE C1 yields C2 CONVERSION.

AU - Olah, George A.

AU - Doggweiler, Hans

AU - Felberg, Jeff D.

AU - Frohlich, Stephan

AU - Grdina, Mary Jo

AU - Karpeles, Richard

AU - Keumi, Takashi

AU - Inaba, Shin ichi

AU - Ip, Wai M.

AU - Lammertsma, Koop

AU - Salem, George

AU - Tabor, Derrick C.

PY - 1984

Y1 - 1984

N2 - The conversion of heterosubstituted methanes, such as methyl alcohol, dimethyl ether, methyl mercaptan, dimethyl sulfide, methylamines, and methyl halides, to ethylene and hydrocarbons derived thereof takes place over bifunctional acidic-basic-supported transition-metal oxide or oxyhalide catalysts, such as tungsten oxide supported on alumina, between 300 and 350 degree C. The conversion of methyl alcohol starts with bimolecular dehydration to dimethyl ether followed by acid-catalyzed transmethylation giving trimethyloxonium ion (or related catalyst-bound methyloxonium ion). The trimethyloxonium ion then undergoes base-induced deprotonation forming a catalyst surface-bound methylenedimethyloxonium ylide. Intermolecular methylation of the ylide, indicated by experiments using singly **1**3C-labeled dimethyl ether, gives methylethyloxonium ion thus providing the crucial first C-C bond.

AB - The conversion of heterosubstituted methanes, such as methyl alcohol, dimethyl ether, methyl mercaptan, dimethyl sulfide, methylamines, and methyl halides, to ethylene and hydrocarbons derived thereof takes place over bifunctional acidic-basic-supported transition-metal oxide or oxyhalide catalysts, such as tungsten oxide supported on alumina, between 300 and 350 degree C. The conversion of methyl alcohol starts with bimolecular dehydration to dimethyl ether followed by acid-catalyzed transmethylation giving trimethyloxonium ion (or related catalyst-bound methyloxonium ion). The trimethyloxonium ion then undergoes base-induced deprotonation forming a catalyst surface-bound methylenedimethyloxonium ylide. Intermolecular methylation of the ylide, indicated by experiments using singly **1**3C-labeled dimethyl ether, gives methylethyloxonium ion thus providing the crucial first C-C bond.

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M3 - Article

AN - SCOPUS:0021754856

SN - 0002-7863

VL - 106

SP - 2134

EP - 2149

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 7

ER -

ONIUM YLIDE CHEMISTRY. 1. BIFUNCTIONAL ACID-BASE-CATALYZED CONVERSION OF HETEROSUBSTITUTED METHANES INTO ETHYLENE AND DERIVED HYDROCARBONS. THE ONIUM YLIDE MECHANISM OF THE C₁ yields C₂ CONVERSION.

Abstract

ASJC Scopus subject areas

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