TWI678395B - 去除含硫化合物的方法、含硫化合物去除用之組成物及其用途 - Google Patents
去除含硫化合物的方法、含硫化合物去除用之組成物及其用途 Download PDFInfo
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- TWI678395B TWI678395B TW105102444A TW105102444A TWI678395B TW I678395 B TWI678395 B TW I678395B TW 105102444 A TW105102444 A TW 105102444A TW 105102444 A TW105102444 A TW 105102444A TW I678395 B TWI678395 B TW I678395B
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- composition
- sulfur
- group
- hydrocarbon
- containing compound
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- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 150000001875 compounds Chemical class 0.000 title claims abstract description 64
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 38
- 239000011593 sulfur Substances 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims description 28
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 51
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 51
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 40
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims abstract description 21
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- -1 polybutylene Polymers 0.000 claims description 38
- GROOSSLNHYKEFI-UHFFFAOYSA-N 2-methyloctanedial Chemical compound O=CC(C)CCCCCC=O GROOSSLNHYKEFI-UHFFFAOYSA-N 0.000 claims description 31
- 239000004215 Carbon black (E152) Substances 0.000 claims description 31
- 239000007789 gas Substances 0.000 claims description 23
- LEMKWEBKVMWZDU-UHFFFAOYSA-N nonanedial Chemical compound O=CCCCCCCCC=O LEMKWEBKVMWZDU-UHFFFAOYSA-N 0.000 claims description 17
- 239000003208 petroleum Substances 0.000 claims description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 11
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- 239000010779 crude oil Substances 0.000 claims description 11
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- LUNMJPAJHJAGIS-UHFFFAOYSA-N 3-methylpentanedial Chemical compound O=CCC(C)CC=O LUNMJPAJHJAGIS-UHFFFAOYSA-N 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 150000003464 sulfur compounds Chemical class 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 229920001748 polybutylene Polymers 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 4
- 239000002184 metal Substances 0.000 abstract description 8
- 229910052751 metal Inorganic materials 0.000 abstract description 8
- 230000007797 corrosion Effects 0.000 abstract description 6
- 238000005260 corrosion Methods 0.000 abstract description 6
- 239000007864 aqueous solution Substances 0.000 description 21
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N alpha-ketodiacetal Natural products O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 20
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- 239000007983 Tris buffer Substances 0.000 description 14
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- 229940015043 glyoxal Drugs 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
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- 230000000052 comparative effect Effects 0.000 description 7
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- 239000002803 fossil fuel Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
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- 229910052742 iron Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IQKPRZPVTQHVOY-UHFFFAOYSA-N 2-methylpentanedial Chemical compound O=CC(C)CCC=O IQKPRZPVTQHVOY-UHFFFAOYSA-N 0.000 description 2
- BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical compound CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OTJFQRMIRKXXRS-UHFFFAOYSA-N (hydroxymethylamino)methanol Chemical compound OCNCO OTJFQRMIRKXXRS-UHFFFAOYSA-N 0.000 description 1
- IDIOUSNRLCLSJE-UHFFFAOYSA-N 1-(piperidin-1-ylmethoxymethoxymethyl)piperidine Chemical compound C1CCCCN1COCOCN1CCCCC1 IDIOUSNRLCLSJE-UHFFFAOYSA-N 0.000 description 1
- RZVBLBGEAFQZRK-UHFFFAOYSA-N 1-(piperidin-1-ylmethoxymethyl)piperidine Chemical compound C1CCCCN1COCN1CCCCC1 RZVBLBGEAFQZRK-UHFFFAOYSA-N 0.000 description 1
- IHHRLHQOHWUAJZ-UHFFFAOYSA-N 1-(pyrrolidin-1-ylmethoxymethoxymethyl)pyrrolidine Chemical compound C1CCCN1COCOCN1CCCC1 IHHRLHQOHWUAJZ-UHFFFAOYSA-N 0.000 description 1
- KQISQNCCCASSDX-UHFFFAOYSA-N 1-(pyrrolidin-1-ylmethyl)pyrrolidine Chemical compound C1CCCN1CN1CCCC1 KQISQNCCCASSDX-UHFFFAOYSA-N 0.000 description 1
- ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical compound CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- QYPLKDUOPJZROX-UHFFFAOYSA-N 2,2-dimethylbutanal Chemical compound CCC(C)(C)C=O QYPLKDUOPJZROX-UHFFFAOYSA-N 0.000 description 1
- XQJVBBCMPCUOJX-UHFFFAOYSA-N 2-ethylheptanedial Chemical compound CCC(C=O)CCCCC=O XQJVBBCMPCUOJX-UHFFFAOYSA-N 0.000 description 1
- GXXVAMCEAMPWGZ-UHFFFAOYSA-N 2-ethylhexanedial Chemical compound CCC(C=O)CCCC=O GXXVAMCEAMPWGZ-UHFFFAOYSA-N 0.000 description 1
- OJEAXIMJLLYVQH-UHFFFAOYSA-N 2-ethylpentanedial Chemical compound CCC(C=O)CCC=O OJEAXIMJLLYVQH-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- XHNPTDYWWTUICE-UHFFFAOYSA-N 4-(morpholin-4-ylmethoxymethyl)morpholine Chemical compound C1COCCN1COCN1CCOCC1 XHNPTDYWWTUICE-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- OGXACZGMMBJZJA-UHFFFAOYSA-N CC(C)(C)N.CCOCCOC(C)O Chemical compound CC(C)(C)N.CCOCCOC(C)O OGXACZGMMBJZJA-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- IPTLKMXBROVJJF-UHFFFAOYSA-N azanium;methyl sulfate Chemical compound N.COS(O)(=O)=O IPTLKMXBROVJJF-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical group SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- JCTHGPXQXLMSDK-UHFFFAOYSA-N bis(Benzyloxy)methane Chemical compound C=1C=CC=CC=1COCOCC1=CC=CC=C1 JCTHGPXQXLMSDK-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- LOCHFZBWPCLPAN-UHFFFAOYSA-N butane-2-thiol Chemical compound CCC(C)S LOCHFZBWPCLPAN-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- AOVGTXWIQWMZGB-UHFFFAOYSA-N cyclohexane-1,2-dicarbaldehyde Chemical compound O=CC1CCCCC1C=O AOVGTXWIQWMZGB-UHFFFAOYSA-N 0.000 description 1
- WHKHKMGAZGBKCK-UHFFFAOYSA-N cyclohexane-1,3-dicarbaldehyde Chemical compound O=CC1CCCC(C=O)C1 WHKHKMGAZGBKCK-UHFFFAOYSA-N 0.000 description 1
- QWKLKVRIQGSSKF-UHFFFAOYSA-N cyclohexane-1,4-dicarbaldehyde Chemical compound O=CC1CCC(C=O)CC1 QWKLKVRIQGSSKF-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000004252 dithioacetals Chemical class 0.000 description 1
- SZCGBFUWBCDIEA-UHFFFAOYSA-N dodecanedial Chemical compound O=CCCCCCCCCCCC=O SZCGBFUWBCDIEA-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical class CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003471 mutagenic agent Substances 0.000 description 1
- QLNNMIUPRPKARZ-UHFFFAOYSA-N n'-cyclopentylmethanediamine Chemical compound NCNC1CCCC1 QLNNMIUPRPKARZ-UHFFFAOYSA-N 0.000 description 1
- MRHFJTMAXCYADG-UHFFFAOYSA-N n-(diethylaminomethoxymethoxymethyl)-n-ethylethanamine Chemical compound CCN(CC)COCOCN(CC)CC MRHFJTMAXCYADG-UHFFFAOYSA-N 0.000 description 1
- HPCLZPLLUNZSGP-UHFFFAOYSA-N n-(diethylaminomethoxymethyl)-n-ethylethanamine Chemical compound CCN(CC)COCN(CC)CC HPCLZPLLUNZSGP-UHFFFAOYSA-N 0.000 description 1
- HCTULTWWHOHSNX-UHFFFAOYSA-N n-[(dipropylamino)methoxymethoxymethyl]-n-propylpropan-1-amine Chemical compound CCCN(CCC)COCOCN(CCC)CCC HCTULTWWHOHSNX-UHFFFAOYSA-N 0.000 description 1
- MSKNLENNQADLSC-UHFFFAOYSA-N n-[(dipropylamino)methoxymethyl]-n-propylpropan-1-amine Chemical compound CCCN(CCC)COCN(CCC)CCC MSKNLENNQADLSC-UHFFFAOYSA-N 0.000 description 1
- HLAOLWFKQBAKSM-UHFFFAOYSA-N n-[2-[1-[2-(tert-butylamino)ethoxy]ethoxy]ethyl]-2-methylpropan-2-amine Chemical compound CC(C)(C)NCCOC(C)OCCNC(C)(C)C HLAOLWFKQBAKSM-UHFFFAOYSA-N 0.000 description 1
- IVETVJOPRZJHDA-UHFFFAOYSA-N n-butyl-n-[(dibutylamino)methoxymethyl]butan-1-amine Chemical compound CCCCN(CCCC)COCN(CCCC)CCCC IVETVJOPRZJHDA-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- KJOMYNHMBRNCNY-UHFFFAOYSA-N pentane-1,1-diamine Chemical compound CCCCC(N)N KJOMYNHMBRNCNY-UHFFFAOYSA-N 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- 230000001988 toxicity Effects 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/20—Organic compounds not containing metal atoms
- C10G29/22—Organic compounds not containing metal atoms containing oxygen as the only hetero atom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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Abstract
本發明係提供一種組成物,其可安全且有效去除烴中所含之含硫化合物,尤其是硫化氫、含-SH基之化合物或此等之混合物,且不引起裝置之金屬腐蝕。
本發明之解決手段係一種組成物,其係用於將烴中之含硫化合物去除之組成物,其特徵為該含硫化合物為硫化氫、含有-SH基之化合物或此等之混合物,且組成物含有碳數6~16之二醛及聚伸烷基二醇。
Description
本發明係有關一種用於將烴中之含硫化合物,典型而言如硫化氫、含-SH基之化合物或此等之混合物去除或減低其濃度之組成物。詳細而言,本發明係有關一種用於將例如天然氣、液化天然氣、酸性氣體、原油、石油腦、重質芳香族石油腦、汽油、煤油、柴油、輕油、重油、FCC漿液、柏油、油田濃縮物等化石燃料或精製石油製品等中所含有的含硫化合物(典型而言如硫化氫)去除之組成物,以及使用該組成物去除含硫化合物(典型而言如硫化氫)之方法。
天然氣、液化天然氣、酸性氣體、原油、石油腦、重質芳香族石油腦、汽油、煤油、柴油、輕油、重油、FCC漿液、柏油、油田濃縮物等化石燃料或精製石油製品等之烴,經常包含硫化氫或含-SH基之各種化合物(典型而言如各種硫醇類)等含硫化合物。硫化氫之毒性已為人所熟知,在從事化石燃料或精製石油製品之產業中,為使硫化氫之含量減低至安全程度,支出相當多之費用及努力。例如針對管道氣體,係要求硫化氫之含量不超過4ppm,作為一般之規定值。又,硫化氫及含-SH基之各種化合物(典型而言如各種硫醇類),由於其揮
發性,而有釋放至蒸氣空間之傾向,在此情況,該等惡臭,會通過貯藏場所及/或其周邊場所、以及用於輸送前述烴之管線及輸出系統,因而成為問題。
基於上述之觀點,在處理化石燃料或精製石油製品之大規模設備中,通常係設置有用於處理含硫化氫之烴或烴流的系統。此等系統具備吸收塔,其中充填與烴或烴流接觸而可吸收硫化氫或含-SH基之各種化合物(典型而言如各種硫醇類)等含硫化合物,視需要可吸收二氧化碳等的烷醇胺、聚乙二醇、阻滯胺等。
為了去除烴中之硫化氫,以往亦有提案使用醛化合物。具體而言,專利文獻1揭示在pH為2~12之範圍的水溶液中之醛化合物與硫化氫之反應,尤其是甲醛水溶液與硫化氫之反應。自此之後,便有多個報告提出有關於為了去除硫化氫而使用醛化合物,例如在專利文獻2中,將甲醛、乙二醛或戊二醛等水溶性醛製成水溶液,作為烴中的硫化氫去除劑使用。
僅將為水溶液之硫化氫去除劑單獨添加於烴中,從混合之觀點而言,尚需要改善,例如在專利文獻3中,藉由將如山梨糖醇倍半油酸酯之乳化劑添加至上述醛類中,可使硫化氫之去除效率提高。又,在專利文獻4中,為了將重質油中之硫化氫有效率地去除,係將為水溶液之硫化氫去除劑及重質油在具備靜態混合器之射出系統
中乳化。此外,為了更提高效率,亦有在系統內添加聚伸烷基二醇之例(專利文獻5、6)。
又,在將上述水溶性醛以水溶液之形態作為硫化氫去除劑使用的情況,會擔心因甲醛、乙二醛、戊二醛的氧化所形成的有機羧酸存在於該水溶液中,而造成裝置之金屬腐蝕。尤其,乙二醛之水溶液具有強金屬腐蝕性。從此觀點,在專利文獻7及專利文獻8中,提案將LiH2PO4、NaH2PO4、Na2HPO4、KH2PO4、K2HPO4等磷酸鹽、磷酸酯、硫代磷酸鹽、硫胺等,作為腐蝕抑制劑併用。
然而,眾所周知甲醛為致突變性物質,又,戊二醛由於高濃度時會自己發生聚合,只能以稀釋狀態使用,從體積效率之觀點而言有問題。
另一方面,專利文獻2不僅揭示前述之水溶性醛,亦揭示使用有機性更高之丙烯醛作為硫化氫去除劑,並於2011年10月30日~11月2日在美國科羅拉多州丹佛市舉辦之SPE年度科技研討暨展覽會(SPE Annual Technical Conference and Exhibition)SPE146080中,發表關於以丙烯醛作為有效成分去除硫化氫。然而,丙烯醛毒性強,為勞動安全上及環境安全上濃度受到嚴格規定之化合物,有操作上需要注意的問題。
專利文獻1 美國專利第1991765號說明書
專利文獻2 美國專利第4680127號說明書
專利文獻3 美國專利第5284635號說明書
專利文獻4 國際公開第2011/087540號
專利文獻5 日本特表2012-525964號公報
專利文獻6 日本特表2013-544305號公報
專利文獻7 美國專利申請公開第2013/090271號說明書
專利文獻8 美國專利申請公開第2013/089460號說明書
非專利文獻1 SPE年度科技研討暨展覽會SPE146080,2011年;http://dx.doi.org/10.2118/146080-MS
如上所述,在使用以往提案之水溶性醛水溶液作為烴及烴流體中所含之硫化氫的去除劑時,由於必須藉由某些手段使其分散於烴中、必須抑制因該水溶液本身所造成之裝置之金屬腐蝕,所以期望進一步改善。
於是,本發明之目的為提供一種組成物,其能安全且有效去除烴中所含之含硫化合物,尤其是硫化氫、含-SH基之化合物或此等之混合物,且不會引起裝置之金屬腐蝕。
本發明如以下之說明。
[1]一種組成物,其係用於去除烴中之含硫化合物的組成物,其特徵為該含硫化合物為硫化氫、含有-SH基之化合物或此等之混合物,且該組成物含有碳數6~16之二醛及聚伸烷基二醇。
[2]如[1]之組成物,其中該二醛係選自包含3-甲基戊二醛、1,9-壬二醛及2-甲基-1,8-辛二醛之群組。
[3]如[1]或[2]之組成物,其中該聚伸烷基二醇係選自聚乙二醇、聚丙二醇、聚丁二醇中之1種或複數種。
[4]如[1]~[3]之組成物,其中去除含硫化合物的對象,即烴,係選自包含天然氣、液化天然氣、酸性氣體、原油、石油腦、重質芳香族石油腦、汽油、煤油、柴油、輕油、重油、FCC漿液、柏油、油田濃縮物之群組中的1種以上。
[5]一種使[1]至[4]中任一項之組成物與烴接觸而去除烴中之含硫化合物的方法,其中該含硫化合物係硫化氫、含-SH基之化合物或此等之混合物。
[6]如[5]之方法,其中該烴係選自包含天然氣、液化天然氣、酸性氣體、原油、石油腦、重質芳香族石油腦、汽油、煤油、柴油、輕油、重油、FCC漿液、柏油、油田濃縮物之群組中的1種以上。
[7]如[5]或[6]之方法,其中相對於烴中所含之含硫化合物1莫耳,添加[1]至[4]中任一項記載之組成物所含之二醛0.1~100莫耳。
[8]如[5]至[7]中任一項之方法,其中使[1]至[4]中任一項之組成物與烴在0℃~200℃之範圍接觸。
[9]一種如[1]至[4]中任一項之組成物的使用,其係用於將烴中之含硫化合物去除,該含硫化合物為硫化氫、含-SH基之化合物或此等之混合物。
本發明之組成物藉由例如1,9-壬二醛及/或2-甲基-1,8-辛二醛之含有碳數6~16之二醛、與聚伸烷基二醇,得使烴中之含硫化合物,尤其是硫化氫、含-SH基之化合物或此等之混合物的去除性能成為優良。與含有戊二醛或乙二醛之以往的硫化氫去除劑相比,本發明之組成物對裝置之金屬腐蝕性較低,在工業上較有利。
第1圖為實施例1、2及比較例1~4中之排放氣體中之H2S濃度對時間的作圖。
在本說明書中,使用本發明之組成物之對象的烴,可為氣體狀、液體狀、固體狀或此等之混合狀態,典型而言可列舉天然氣、液化天然氣、酸性氣體、原油、石油腦、重質芳香族石油腦、汽油、煤油、柴油、輕油、重油、FCC漿液、柏油、油田濃縮物等之化石燃料或精製石油製品等、及此等之任意組合,然而不以此等為限。
在本發明中,使用本發明之組成物所去除之對象的前述烴中可含有之含硫化合物,係硫化氫、含-SH基之化合物或此等之混合物。此處,就含-SH基之化合物而言,可列舉分類為化學式「R-SH」所示之硫醇類的含硫化合物,例如R為烷基之甲基硫醇、乙基硫醇、丙基硫醇、異丙基硫醇、正丁基硫醇、異丁基硫醇、二級丁基硫醇、三級丁基硫醇、正戊基硫醇;R為芳基之苯基硫醇;R為芳烷基之苄基硫醇等,然而不以此等為限。
本發明之組成物,其特徵為含有碳數6~16之二醛。
藉由烴中之含硫化合物對該二醛進行加成反應,可從烴中去除含硫化合物。
在含硫化合物為具有-SH基之化合物的情況,藉由-SH基對二醛之甲醯基(R’-CH=O)進行加成反應,轉變為硫縮醛類(R’-CH(OH)SR)或二硫縮醛類(R’-CH(SR)2),可去除-SH基。
另一方面,在含硫化合物為硫化氫之情況,硫化氫會對二醛之甲醯基(R’-CH=O)進行加成反應,轉變為R’-CH(OH)SH或R’-CH(SH)2之具有-SH基的化合物。然後,藉由與上述相同的反應機構即可去除-SH基。
就前述碳數6~16之二醛而言,以脂肪族二醛為較佳,可列舉如:甲基戊二醛、1,6-己二醛、乙基戊二醛、1,7-庚二醛、甲基己二醛、1,8-辛二醛、甲基庚二醛、二甲基己二醛、乙基己二醛、1,9-壬二醛、甲基辛二醛、乙基庚二醛、1,10-癸二醛、二甲基辛二醛、乙
基辛二醛、十二碳二醛、十六碳二醛、1,2-環己二甲醛、1,3-環己二甲醛、1,4-環己二甲醛、1,2-環辛二甲醛、1,3-環辛二甲醛、1,4-環辛二甲醛、1,5-環辛二甲醛等。此等之中,以3-甲基戊二醛、1,9-壬二醛、2-甲基-1,8-辛二醛為較佳,從低毒性、生物分解性、操作上之安全性、耐熱性等觀點而言,以含有1,9-壬二醛及2-甲基-1,8-辛二醛中之至少一者為進一步更佳。
在本發明之組成物含有1,9-壬二醛及2-甲基-1,8-辛二醛中之至少一者的情況,就有效成分而言,可單獨為1,9-壬二醛或單獨為2-甲基-1,8-辛二醛,然而從工業上取得容易性之觀點而言,以1,9-壬二醛及2-甲基-1,8-辛二醛之混合物之形態為特佳。該1,9-壬二醛及2-甲基-1,8-辛二醛之混合物之混合比無特別限制,通常就1,9-壬二醛/2-甲基-1,8-辛二醛之質量比而言,以99/1~1/99為較佳,以95/5~5/95為更佳,以90/10~45/55為進一步更佳,以90/10~55/45為特佳。
3-甲基戊二醛、1,9-壬二醛及2-甲基-1,8-辛二醛之任一項均為周知物質,可依照周知之方法(例如若為3-甲基戊二醛則依照Organic Syntheses,Vol.34,p.29(1954)、及Organic Syntheses,Vol.34,p.71(1954)等記載之方法,又若為1,9-壬二醛及2-甲基-1,8-辛二醛則依照日本專利第2857055號公報、日本特公昭62-61577號公報等記載之方法)或以其為基準之方法而製造。又,此等亦可使用市售品。
本發明之組成物,其特徵為除了含有上述碳數6~16之二醛外,亦可進一步含有聚伸烷基二醇。就聚伸烷基二醇而言,可列舉如:聚乙二醇、聚丙二醇、聚丁二醇、聚氧雜環丁烷、聚四亞甲基醚二醇等。此等之中,從價格及對二醛之親和性之觀點而言,以聚乙二醇、聚丙二醇、聚丁二醇為較佳。此等可單獨使用1種,亦可將2種以上併用。
所用之聚伸烷基二醇之數平均分子量無特別限制,通常為100~20,000,以100~4,000為較佳,以150~600為進一步更佳。若數平均分子量超過20,000,則由於黏度變高、流動性降低,會增大對裝置之負擔。在小於100時,羥基之濃度變高,恐怕誘發與二醛之預期反應。
聚伸烷基二醇可使用市售品,亦可依照周知之方法,例如環氧烷之開環聚合而製造。
本發明之組成物中,二醛與聚伸烷基二醇之含有比率的合計,可依據使用態樣而適宜設定,通常為1~100質量%,從費用對效果之觀點而言,較佳為5~100質量%,更佳為5~95質量%。
本發明之組成物中,二醛與聚伸烷基二醇之含量之比,在以二醛為A(質量部)、聚伸烷基二醇為B(質量部)之情況,通常A:B=0.1:99.9~99.9:0.1,從費用對效果之觀點而言,較佳為A:B=20:80~99.9:0.1。
本發明之組成物之製造方法無特別限制,可採用其本身周知之方法或以其為基準之方法。例如可藉
由在二醛中添加聚伸烷基二醇及視需要添加之後述任意成分並混合等而製造,其中該二醛較佳為選自甲基戊二醛、1,9-壬二醛及2-甲基-1,8-辛二醛中之至少1種,特佳為1,9-壬二醛與2-甲基-1,8-辛二醛之混合物。
本發明之組成物較佳為液狀,不過順應為了去除烴中之含硫化合物而使用之形態,亦可為承載於適當載劑等形態的粉體、粒體等固體狀。
在使用本發明之組成物去除烴中之含硫化合物的方法中,除了本發明之組成物外,亦可將甲醛、乙二醛、戊二醛、丙烯醛等以往周知作為硫化氫去除劑之醛化合物,在無損於本發明之效果的範圍內適宜添加而使用。
又,在使用本發明之組成物去除烴中之含硫化合物的方法中,亦可在使本發明之效果更為增大、或無損害的範圍內,添加含氮化合物。就該含氮化合物而言,可列舉如:N,N’-氧基雙(亞甲基)雙(N,N-二丁基胺)、N,N’-(亞甲基雙(氧基)雙(亞甲基))雙(N,N-二丁基胺)、4,4’-氧基雙(亞甲基)二啉、雙(啉基甲氧基)甲烷、1,1’-氧基雙(亞甲基)二哌啶、雙(哌啶基甲氧基)甲烷、N,N’-氧基雙(亞甲基)雙(N,N-二丙基胺)、N,N’-(亞甲基雙(氧基)雙(亞甲基))雙(N,N-二丙基胺)、1,1’-氧基雙(亞甲基)二吡咯啶、雙(吡咯啶基甲氧基)甲烷、N,N’-氧基雙(亞甲基)雙(N,N-二乙基胺)、N,N’-(亞甲基雙(氧基)雙(亞甲基))雙(N,N-二乙基胺)等α胺基醚化合物;1,3,5-三甲氧基丙基-六氫-1,3,5-三、1,3,5-三甲氧基乙基-六氫
-1,3,5-三、1,3,5-三(3-乙氧基丙基)-六氫-1,3,5-三、1,3,5-三(3-異丙氧基丙基)-六氫-1,3,5-三、1,3,5-三(3-丁氧基丙基)-六氫-1,3,5-三、1,3,5-三(5-甲氧基戊基)-六氫-1,3,5-三等烷氧基-六氫三化合物;1,3,5-三甲基-六氫-1,3,5-三、1,3,5-三乙基-六氫-1,3,5-三、1,3,5-三丙基-六氫-1,3,5-三、1,3,5-三丁基-六氫-1,3,5-三等烷基-六氫三化合物;1,3,5-三(羥基甲基)-六氫-1,3,5-三、1,3,5-三(2-羥基乙基)-六氫-1,3,5-三、1,3,5-三(3-羥基丙基)-六氫-1,3,5-三等羥基烷基-六氫三化合物;單甲基胺、單乙基胺、二甲基胺、二丙基胺、三甲基胺、三乙基胺、三丙基胺、單甲醇胺、二甲醇胺、三甲醇胺、二乙醇胺、三乙醇胺、單異丙醇胺、二丙醇胺、二異丙醇胺、三丙醇胺、N-甲基乙醇胺、二甲基(乙醇)胺、甲基二乙醇胺、二甲基胺基乙醇、乙氧基乙氧基乙醇三級丁基胺等單胺化合物;胺基甲基環戊基胺、1,2-環己二胺、1,4-丁二胺、1,5-戊二胺、1,6-己二胺、雙(三級丁基胺基乙氧基)乙烷等二胺化合物;亞胺化合物;咪唑啉化合物;羥基胺基烷基醚化合物;啉化合物;吡咯啶酮化合物;哌啶酮化合物;烷基吡啶化合物;1H-六氫氮呯;伸乙基二胺與甲醛之反應生成物等伸烷基多胺與甲醛之反應生成物;胺基羧酸之多價金屬螯合化合物;苄基(椰子油烷基)(二甲基)氯四級銨、二(椰子油烷基)二甲基氯化銨、二(牛脂烷基)二甲基氯四級銨、二(氫化牛脂烷基)二甲基氯四級銨、二甲基(2-乙基己基)(牛脂烷基)銨甲基硫酸鹽、(氫化牛脂烷基)(2-乙基
己基)二甲基四級銨甲基硫酸鹽等四級銨鹽化合物;聚伸乙基亞胺、聚烯丙基胺、聚乙烯基胺;胺基原醇化合物;縮醛胺化合物;雙唑啶化合物等。此等可單獨使用1種,亦可將2種以上併用。
就本發明之較佳實施態樣之例而言,係將本發明之組成物以可充分除去含硫化合物(硫化氫、含-SH基之化合物或此等之混合物)之量添加於烴中,或使此等含有含硫化合物之氣體狀烴流通於充填有本發明之組成液的容器而進行處理。在使用本發明之組成物而去除烴中之含硫化合物的方法中,本發明之組成物中所含之二醛之量,相對於1莫耳烴中之含硫化合物,通常添加0.1~100莫耳,較佳添加1~100莫耳。在前述之使烴流通於充填有本發明之組成液的容器而進行處理之方法中,相對於所流通之烴中的含硫化合物1莫耳,係以所添加之二醛之量成為前述範圍內的方式,來調整本發明之組成物之添加量。將本發明之組成物添加於烴中與之接觸,而進行處理時之溫度通常為0℃~200℃,較佳在20℃~120℃之範圍。又,本發明之組成物,亦可溶解於環己烷、甲苯、二甲苯、重質芳香族石油腦、石油蒸餾物;甲醇、乙醇、乙二醇等碳數1~10之一元醇或二元醇等適當溶劑中而使用。
在使用本發明之組成物之,去除烴中之含硫化合物的方法中,在烴為液體之情況,可藉由對其貯槽、用於輸送之管線、用於精製之蒸餾塔等進行注入等周知手段來進行添加。在烴為氣體之情況,可採取以與氣體
接觸之方式設置本發明之組成物、或使氣體通過充填有本發明之組成物的吸收塔等手段。
以下,藉由實施例等更詳細地說明本發明,不過本發明並不限定於此等實施例。
依照專利第2857055號公報記載之方法,製造1,9-壬二醛(以下稱為NL)與2-甲基-1,8-辛二醛(以下稱為MOL)之混合物。該混合物中NL與MOL之質量比為NL/MOL=85/15。
在具備溫度計、攪拌機之100mL熱壓釜中添加20mL之PEG-200(和光純藥股份有限公司製),一面以800rpm攪拌一面將溫度調整至25℃,使調整至10,000ppm之H2S標準氣體以16mL/分鐘之速度流通。在使裝置內經充分置換後,將錶壓調至0.1MPa,使用RX-517(理研機器製)開始測定排放氣體中之H2S濃度,隨即將PEG-200與NL/MOL以質量比成為1:1之方式混合而成的組成液20mL,費時4分鐘添加於熱壓釜內。此時之NL/MOL的添加量為64.0mmol。添加結束後,使其流通2小時,結果,H2S之總流通量成為0.8mmol,由排放氣體中之H2S濃度所計算出的H2S之總反應量為0.8mmol。
除了將PEG-200變更為甲苯(和光純藥股份有限公司製)以外,以與實施例1同樣之條件進行反應時,NL/MOL之添加量為57.4mmol。H2S之總流通量為0.8mmol,由排放氣體中之H2S濃度所計算出的H2S之總反應量為0.3mmol。
除了將PEG-200變更為甲苯:PEG-200=99:1(質量比)之混合液以外,以與實施例1同樣之條件進行反應時,NL/MOL之添加量為57.4mmol。H2S之總流通量為0.8mmol,由排放氣體中之H2S濃度所計算出的H2S之總反應量為0.5mmol。
除了將PEG-200變更為異丙醇(IPA,和光純藥股份有限公司製)以外,以與實施例1同樣之條件進行反應時,NL/MOL之添加量為54.9mmol。H2S之總流通量為0.8mmol,由排放氣體中之H2S濃度所計算出的H2S之總反應量為0.4mmol。
除了將PEG-200變更為乙酸乙酯(AcOEt,和光純藥股份有限公司製)以外,以與實施例1同樣之條件進行反
應時,NL/MOL之添加量成為58.9mmol。H2S之總流通量為0.8mmol,由排放氣體中之H2S濃度所計算出的H2S之總反應量為0.3mmol。
除了將PEG-200與NL/MOL混合之組成液變更為只有PEG-200以外,以與實施例1同樣之條件進行反應時,H2S之總流通量為0.8mmol,由排放氣體中之H2S濃度所計算出的H2S在PEG-200中之溶解量為0.1mmol。
將實施例1、2及比較例1~4中之排放氣體中之H2S濃度對時間的作圖,示於第1圖。再者,在第1圖中,將結束添加本發明之組成物的時點當作0分鐘。
在具備溫度計、攪拌機之100mL熱壓釜中,添加30mL之採取自日本由利原礦場的原油(石油資源股份有限公司製),將之攪拌至氣相部之H2S濃度成為恆定後,使用RX-517(理研機器製)測定濃度時為2,800ppm。繼而將PEG-200與NL/MOL以質量比成為1:1之方式混合的組成液,以對原油成為1質量%之方式添加。此時之NL/MOL之添加量為1.0mmol,裝置內之H2S之存在量為0.05mmol。然後,在裝置內一面以800rpm攪拌一面升溫至80℃,反應5小時。反應後冷卻至室溫,測定氣相部分之H2S濃度時為2ppm,去除效率為99.9%。
在具備溫度計、攪拌機之100mL熱壓釜中添加30mL之採取自日本由利原礦場的原油(石油資源股份有限公司製),將之攪拌至氣相部分之H2S濃度成為恆定後,使用RX-517(理研機器製)測定濃度時為2,600ppm。繼而將40質量%乙二醛水溶液(和光純藥股份有限公司製)以相對於原油成為1質量%之方式添加。此時之乙二醛之添加量為1.8mmol,裝置內之H2S之存在量為0.04mmol。然後,在裝置內一面以800rpm攪拌一面升溫至80℃,反應5小時。反應後冷卻至室溫,測定氣相部分之H2S濃度時為498ppm,去除效率為80.8%。
為了評價醛水溶液之金屬腐蝕性,準備下述之水溶液。
A.1%NL/MOL水溶液:將NL/MOL之混合物用蒸餾水稀釋
B.1%戊二醛水溶液:將50%戊二醛水溶液(和光純藥工業股份有限公司製)用蒸餾水稀釋
C.1%乙二醛水溶液:將40%乙二醛水溶液(東京化成工業股份有限公司製)用蒸餾水稀釋
D.蒸餾水(空白對照)
將SS400之試驗片(20mm×20mm×2mm)及上述醛水溶液A~D各25g,於大氣下放入4支50mL螺旋管中,並密閉,在設定成85℃之循環型乾燥機內保存9
日。保存結束後,取出試驗片,藉由原子吸光法測定水溶液中之鐵離子濃度,將結果示於表1。
在試驗例1中,除於氮氣下密閉以外,以與試驗例1相同順序進行,測定各種水溶液中之鐵離子濃度。將結果示於表1。
從試驗例1及試驗例2之結果可知,NL/MOL水溶液比戊二醛水溶液或乙二醛水溶液更能抑制鐵之腐蝕。
Claims (9)
- 一種組成物,其係用於去除烴中之含硫化合物的組成物,其特徵為該含硫化合物為硫化氫、含-SH基之化合物或此等之混合物,且組成物含有碳數6~16之二醛及聚伸烷基二醇。
- 如請求項1之組成物,其中該二醛係選自包含3-甲基戊二醛、1,9-壬二醛及2-甲基-1,8-辛二醛之群組。
- 如請求項1或2之組成物,其中該聚伸烷基二醇係選自聚乙二醇、聚丙二醇、聚丁二醇中之1種或複數種。
- 如請求項1或2之組成物,其中去除含硫化合物之對象,即烴,係選自包含天然氣、液化天然氣、酸性氣體、原油、石油腦、重質芳香族石油腦、汽油、煤油、柴油、輕油、重油、FCC漿液、柏油、油田濃縮物之群組中的1種以上。
- 一種使如請求項1至4中任一項之組成物與烴接觸而去除烴中之含硫化合物的方法,其中該含硫化合物係硫化氫、含-SH基之化合物或此等之混合物。
- 如請求項5之方法,其中該烴係選自包含天然氣、液化天然氣、酸性氣體、原油、石油腦、重質芳香族石油腦、汽油、煤油、柴油、輕油、重油、FCC漿液、柏油、油田濃縮物之群組中的1種以上。
- 如請求項5或6之方法,其中相對於烴中所含之含硫化合物1莫耳,添加如請求項1至4中任一項之組成物所含之二醛0.1~100莫耳。
- 如請求項5或6之方法,其中使如請求項1至4中任一項之組成物與烴在0℃~200℃之範圍接觸。
- 一種如請求項1至4中任一項之組成物的使用,其係用於將烴中之含硫化合物去除,其中該含硫化合物為硫化氫、含-SH基之化合物或此等之混合物。
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EP (1) | EP3252129B1 (zh) |
JP (1) | JP6621030B2 (zh) |
KR (1) | KR20170110079A (zh) |
CN (1) | CN107207974B (zh) |
CA (1) | CA2974070A1 (zh) |
RU (1) | RU2693494C2 (zh) |
TW (1) | TWI678395B (zh) |
WO (1) | WO2016121747A1 (zh) |
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BR112017005174A2 (pt) * | 2014-09-19 | 2017-12-05 | Kuraray Co | inibidor de corrosão biológica para metais |
EP3530775A4 (en) * | 2016-09-27 | 2020-05-27 | Kuraray Co., Ltd. | METHOD FOR SUPPRESSING METAL CORROSION |
EP3546052B1 (en) * | 2016-11-22 | 2023-08-16 | Kuraray Co., Ltd. | Composition for removal of sulfur-containing compound |
CN110573232A (zh) * | 2017-05-12 | 2019-12-13 | 株式会社可乐丽 | 含硫化合物去除装置和含硫化合物去除方法 |
EA039258B1 (ru) * | 2017-06-21 | 2021-12-23 | Курарей Ко., Лтд. | Композиция для удаления серосодержащего соединения |
JP2020143170A (ja) * | 2017-06-29 | 2020-09-10 | 株式会社クラレ | アスファルト中の含硫黄化合物除去用の組成物 |
US11286433B2 (en) * | 2017-08-01 | 2022-03-29 | Gaps Technology, Llc | Compositions and methods for remediating hydrogen sulfide in hydrocarbon based liquids |
EP3760293A4 (en) * | 2018-02-28 | 2021-11-10 | Kuraray Co., Ltd. | COMPOSITION TO ELIMINATE A COMPOUND CONTAINING SULFUR |
JP2020019898A (ja) * | 2018-08-01 | 2020-02-06 | 独立行政法人石油天然ガス・金属鉱物資源機構 | 生産流体処理システム及び生産流体の処理方法 |
US11840669B2 (en) | 2018-12-21 | 2023-12-12 | Kuraray Co., Ltd. | Method for hydrocarbon production, purification method, and purifier |
WO2021076944A1 (en) | 2019-10-17 | 2021-04-22 | Nexgen Oilfield Chemicals, Llc | Methods and compositions for scavenging sulfides from hydrocarbon fluids and aqueous streams |
EP4093836A1 (en) | 2020-01-23 | 2022-11-30 | ChampionX USA Inc. | Compositions of heterocyclic compounds and uses as sulfidogenesis inhibitors |
CN114159946B (zh) * | 2022-02-11 | 2022-04-29 | 河北精致科技有限公司 | 一种用于脱除烟气中二氧化硫的吸收剂及其应用 |
US11946008B2 (en) | 2022-05-04 | 2024-04-02 | Nexgen Oilfield Chemicals, Llc | Compositions and methods for scavenging hydrogen sulfide |
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2016
- 2016-01-26 CN CN201680007120.1A patent/CN107207974B/zh not_active Expired - Fee Related
- 2016-01-26 RU RU2017126366A patent/RU2693494C2/ru not_active IP Right Cessation
- 2016-01-26 WO PCT/JP2016/052157 patent/WO2016121747A1/ja active Application Filing
- 2016-01-26 KR KR1020177019893A patent/KR20170110079A/ko unknown
- 2016-01-26 CA CA2974070A patent/CA2974070A1/en not_active Abandoned
- 2016-01-26 JP JP2016572051A patent/JP6621030B2/ja active Active
- 2016-01-26 US US15/546,091 patent/US10294428B2/en active Active
- 2016-01-26 EP EP16743350.7A patent/EP3252129B1/en active Active
- 2016-01-27 TW TW105102444A patent/TWI678395B/zh not_active IP Right Cessation
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CN103209752A (zh) * | 2010-11-22 | 2013-07-17 | 多尔夫凯塔尔化学制品(I)私人有限公司 | 用于清除烃流中的硫化氢的添加剂组合物和方法 |
US20130004393A1 (en) * | 2011-06-29 | 2013-01-03 | Baker Hughes Incorporated | Synergistic Method for Enhanced H2S/Mercaptan Scavenging |
Also Published As
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CA2974070A1 (en) | 2016-08-04 |
EP3252129B1 (en) | 2019-08-14 |
WO2016121747A1 (ja) | 2016-08-04 |
JPWO2016121747A1 (ja) | 2017-11-16 |
US10294428B2 (en) | 2019-05-21 |
EP3252129A4 (en) | 2018-07-25 |
JP6621030B2 (ja) | 2019-12-18 |
US20180010056A1 (en) | 2018-01-11 |
EP3252129A1 (en) | 2017-12-06 |
RU2017126366A3 (zh) | 2019-05-21 |
KR20170110079A (ko) | 2017-10-10 |
CN107207974B (zh) | 2019-11-15 |
RU2693494C2 (ru) | 2019-07-03 |
TW201634579A (zh) | 2016-10-01 |
CN107207974A (zh) | 2017-09-26 |
RU2017126366A (ru) | 2019-03-01 |
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