Method for converting natural gas to liquid hydrocarbons
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IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07C-027/00
C07C-002/00
C07C-011/00
C07C-002/56
출원번호
US-0803122
(2001-03-09)
발명자
/ 주소
Hall, Kenneth R.
Bullin, Jerry A.
Eubank, Philip T.
Akgerman, Aydin
Anthony, Rayford G.
출원인 / 주소
The Texas A&M University System
대리인 / 주소
Baker Botts L.L.P.
인용정보
피인용 횟수 :
25인용 특허 :
56
초록▼
A process for converting natural gas to a liquid includes heating the gas to a selected range of temperature to convert a fraction of the gas stream to reactive hydrocarbons, primarily ethylene or acetylene, and reacting methane and the reactive hydrocarbons in the presence of an acidic catalyst to
A process for converting natural gas to a liquid includes heating the gas to a selected range of temperature to convert a fraction of the gas stream to reactive hydrocarbons, primarily ethylene or acetylene, and reacting methane and the reactive hydrocarbons in the presence of an acidic catalyst to produce a liquid, predominantly naphtha or gasoline. A portion of the incoming natural gas may be used to heat the remainder of the natural gas to the selected range of temperature. Hydrogen resulting from the reactions may be used to make electricity in a fuel cell. Alternatively, hydrogen may be burned to heat the natural gas to the selected range of temperature.
대표청구항▼
A process for converting natural gas to a liquid includes heating the gas to a selected range of temperature to convert a fraction of the gas stream to reactive hydrocarbons, primarily ethylene or acetylene, and reacting methane and the reactive hydrocarbons in the presence of an acidic catalyst to
A process for converting natural gas to a liquid includes heating the gas to a selected range of temperature to convert a fraction of the gas stream to reactive hydrocarbons, primarily ethylene or acetylene, and reacting methane and the reactive hydrocarbons in the presence of an acidic catalyst to produce a liquid, predominantly naphtha or gasoline. A portion of the incoming natural gas may be used to heat the remainder of the natural gas to the selected range of temperature. Hydrogen resulting from the reactions may be used to make electricity in a fuel cell. Alternatively, hydrogen may be burned to heat the natural gas to the selected range of temperature. a heterocycle and a substituted heterocycle; wherein V2comprises one of S, S=O and SO2, W7comprises one of a hydrogen atom, a lower alkyl group, a substituted lower alkyl group, a lower alkylcarbonyl group, a substituted lower alkylcarbonyl group and a trihalomethyl group, wherein: when X is CHW0,CW0W0or CW0at least one of R5to R8is a hydroxyl group, provided that at least one of R5,R7or R8is a hydroxy group when the X--Y bond is CH(C2H5)CO and R6is a hydroxyl group and when X is other than CHW0,CW0W0or CW0at least one of R5to R8is a hydroxyl group and, at the same time, at least one of the other R5to R8is a group of OR wherein W0is any one selected from a lower alkyl group and a substituted lower alkyl group and R is any one selected from the group consisting of a hydrogen atom, a lower alkyl group, a substituted lower alkyl group, a lower alkylcarbonyl group and a substituted lower alkylsilyl group; and when X--Y comprises CH2CH2,CHBrCH2,CH2CO, CHBrCO, CH=CH, CH=COCOCH3or CH=COCH3, at least one of R1to R4is an aromatic ring, a substituted aromatic ring, a heterocycle or a substituted heterocycle provided that when both R6and R7are hydroxyl groups, any one of R1to R4is not a phenyl group; or at least one of R1to R4comprises SW8or S(O)W9wherein W8and W9independently comprise a lower alkyl group or a substituted lower alkyl group; or R2comprises either a lower alkyl group or a substituted lower alkyl group and, at the same time, R8comprises a hydroxyl group; or at least one of R1to R4comprises a lower alkylcarbonyl group provided that the number of carbon atoms of the lower alkyl group is 3 or more, a cycloalkylcarbonyl group or a cycloalkenylcarbonyl group and, at the same time, R8is a hydroxyl group; or at least one of R1to R4comprises a cyano group; or at least one of R1to R4comprises a halogen and, at the same time, Z is any one of S, S=O and SO2; or R5and R6comprise hydroxyl groups and, at the same time, Z is S; or at least one of R1to R4comprises --C(=NOR)CH3wherein R comprises a hydrogen atom or a lower alkyl group, an optical isomer thereof, a conjugate thereof or a pharmaceutically acceptable salt thereof. 2. The compound according to claim 1, wherein R6is a hydroxyl group. 3. The compound according to claim 1, wherein R6and R7are hydroxyl groups. 4. The compound according to claim 1, wherein R6and R8are hydroxyl groups. 5. The compound according to claim 1, wherein R5and R6are hydroxyl groups. 6. The compound according to claim 1, wherein the X--Y bond is a single bond and X comprises CW1W2or the X--Y bond is a double bond and X comprises CW, wherein at least one of W1and W2is selected from a lower alkyl group, a substituted lower alkyl group, a cycloalkyl group and a cycloalkenyl group and W is one of a lower alkyl group, a substituted lower alkyl group, a cycloalkyl group and a cycloalkenyl group. 7. The compound according to claim 1, wherein Y comprises CO. 8. The compound according to claim 6, wherein the lower alkyl group is any one of a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group and a tert-butyl group. 9. The compound according to claim 1, wherein R2or R3is any one of a heterocycle, a substituted heterocycle, an aromatic ring and a substituted aromatic ring. 10. The compound according to claim 1, wherein the heterocyle is an aromatic heterocyle. 11. The compound according to claim 1, wherein R2or R3is SW8or S(O)W9,wherein W8is a lower alkyl group or a substituted lower alkyl group, and W9is a lower alkyl group or a substituted alkyl group. 12. The compound according to claim 11, wherein the lower alkyl group comprises any one of a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group and a tert-butyl group. 13. The compound according to claim 1, wherein Z comprises S. 14. The compound according to claim 1 wherein the compound comprises 7,8-dihydroxy-1-ethyl-10,11-dihydrodibenzo[b,j]thiepin-10-one. 15. The compound according to claim 1 wherein the compound comprises 11-diethyl-7,8-dihydroxy-10,11-dihydrodibenzo[b,j]thiepin-10-one. 16. The compound according to claim 1 wherein the compound comprises 7,9-dihydroxy-2-methylthio-10,11-dihydrodibenzo[b,j]thiepin-10-one. 17. A method of preparing a compound represented by formula (1), wherein when the X--Y bond is a single bond, X and Y are independently selected from the group consisting of: CW1W2wherein W1and W2are independently selected from the group comprising one of a hydrogen atom, a halogen, a hydroxyl group, a lower alkyl group, a substituted lower alkyl group, a lower alkoxy group, a cycloalkyl group and a cycloalkenyl group, C=O, and C=NOW3wherein W3comprises a hydrogen atom or a lower alkyl group; when the X--Y bond is a double bond, X and Y independently comprise CW4wherein W4comprises any one of a hydrogen atom, a halogen, a hydroxyl group, a lower alkyl group, a substituted lower alkyl group, a lower alkoxy group and an acyloxy group; Z comprises any one of S, S=O and SO2; U comprises C; R1to R4are independently selected from the group consisting of a hydrogen atom, a lower alkyl group, a substituted lower alkyl group, a cycloalkyl group, a substituted cycloalkyl group, a lower alkenyl group, a substituted lower alkenyl group, a lower alkynyl group, a substituted lower alkynyl group, a halogen, a lower alkylcarbonyl group, a substituted lower alkylcarbonyl group, a trihalomethyl group, V1W5,a nitro group, an amino group, a substituted amino group, a cyano group, an acyl group, an acylamino group, a substituted acyl group, a substituted acylamino group, an aromatic ring, a substituted aromatic ring, a heterocycle and a substituted heterocycle wherein V1comprises any one of S, S=O and SO2, W5comprises any one of a hydrogen atom, a lower alkyl group, a substituted lower alkyl group, a lower alkylcarbonyl group and a substituted lower alkylcarbonyl group, an acyloxy group and a trihalomethyl group, R5to R8are independently selected from the group consisting of a hydrogen atom, a lower alkyl group, a substituted lower alkyl group, a lower alkenyl group, a substituted lower alkenyl group, a lower alkynyl group, a substituted lower alkynyl group, a halogen, a lower alkylcarbonyl group, a substituted lower alkylcarbonyl group, a trihalomethyl group, V2W7,a nitro group, an amino group, a substituted amino group, an acylamino group, an aromatic ring, a substituted aromatic ring, a heterocycle and a substituted heterocycle; wherein V2comprises one of S, S=O and SO2, W7comprise one of a hydrogen atom, a lower alkyl group, a substituted lower alkyl group, a lower alkylcarbonyl group, a substituted lower alkylcarbonyl group and a trihalomethyl group, wherein: when X is CHW0,CW0W0or CW0at least one of R5to R8is a hydroxyl group, provided that at least one of R5,R7or R8is a hydroxy group when the X--Y bond is CH(C2H5)CO and R6a hydroxyl group and when X is other than CHW0,CW0W0or CW0at least one of R5to R8is a hydroxyl group and, at the same time, at least one of the other R5to R8is a group of OR wherein W0is any one selected from a lower alkyl group and a substituted lower alkyl group and R is any one selected from the group consisting of a hydrogen atom, a lower alkyl group, a substituted lower alkyl group, a lower alkylcarbonyl group and a substituted lower alkylsilyl group; and when X--Y comprises CH2CH2,CHBrCH2,CH2CO, CHBrCO, CH=CH, CH=COCOCH3or CH=COCH3, at least one of R1to R4is an aromatic ring, a substituted aromatic ring, a heterocycle or a substituted heterocycle provided that when both R6and R7are hydroxyl groups, any one of R1to R4is not a phenyl group; or at least one of R1to R4comprises SW8or S(O)W9wherein W8and W9independently comprise a lower alkyl group or a substituted lower alkyl group; or R2comprises either a lower alkyl group or a substituted lower alkyl group and, at the same time, R8comprises a hydroxyl group; or at least one of R1to R4comprises a lower alkylcarbonyl group provided that the number of carbon atoms of the lower alkyl group is 3 or more, a cycloalkylcarbonyl group or a cycloalkenylcarbonyl group and, at the same time, R8is a hydroxyl group; or at least one of R1to R4comprises a cyano group; or at least one of R1to R4comprises a halogen and, at the same time, Z is any one of S, S=O and SO2; or R5and R6comprise hydroxyl groups and, at the same time, Z is S; or at least one of R1to R4comprise --C(=NOR)CH3wherein R comprises a hydrogen atom or a lower alkyl group, an optical isomer thereof, a conjugate thereof or a pharmaceutically acceptable salt thereof, which comprises, in any order, the reaction steps of (1) bonding a ring A to a ring C by the Ullmann reaction as shown in formula 2 and (2) bonding a ring A to a ring C by the Friedel-Crafts reaction or photoreaction as shown in formula 3, wherein Q, S and W are each any substituent; U is C; one of X and Y is a leaving group and the other is a nucleophilic group; and Z is any one of S, SO and SO2. 18. The method according to claim 17 further comprising at least one of a carbon atom increasing reaction, a conversion reaction of a substituent, an introduction reaction of a substituent, a removal of the protection of a substituent, forming a salt, and performing optical resolution. 19. A pharmaceutical composition comprising an effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier or diluent. 20. The pharmaceutical composition according to claim 19 wherein the pharmaceutical composition utilizes the tracheal smooth muscles relaxing action of the compound. 21. The pharmaceutical composition according to claim 19 wherein the pharmaceutical composition utilizes the inhibitory effect on airway hypersensitivity of the compound. 22. The pharmaceutical composition according to claim 19 wherein the pharmaceutical composition utilizes the inhibitiory effect on inflammatory cells infiltration of the compound. 23. The pharmaceutical composition according to claim 19 wherein the pharmaceutical composition is used as the anti-asthmatic drug. 24. The compound of claim 1 wherein X and Y are the same. 25. The compound of
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