CN1320081C - Prep. of low aromatic hydrocarbon solvent, straight-chain paraffin and pressure-sensitive copy material - Google Patents
Prep. of low aromatic hydrocarbon solvent, straight-chain paraffin and pressure-sensitive copy material Download PDFInfo
- Publication number
- CN1320081C CN1320081C CNB011163887A CN01116388A CN1320081C CN 1320081 C CN1320081 C CN 1320081C CN B011163887 A CNB011163887 A CN B011163887A CN 01116388 A CN01116388 A CN 01116388A CN 1320081 C CN1320081 C CN 1320081C
- Authority
- CN
- China
- Prior art keywords
- pressure
- aromatic hydrocarbon
- oil
- solvent
- fraction
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- 239000002904 solvent Substances 0.000 title claims abstract description 85
- 239000000463 material Substances 0.000 title claims abstract description 45
- 239000012188 paraffin wax Substances 0.000 title claims abstract description 37
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 46
- 238000000034 method Methods 0.000 claims abstract description 33
- 239000003350 kerosene Substances 0.000 claims abstract description 22
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 19
- 239000010457 zeolite Substances 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 239000002808 molecular sieve Substances 0.000 claims abstract description 10
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012916 chromogenic reagent Substances 0.000 claims description 28
- 239000005864 Sulphur Substances 0.000 claims description 21
- -1 bicyclic alkane Chemical class 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 238000006477 desulfuration reaction Methods 0.000 claims description 17
- 230000023556 desulfurization Effects 0.000 claims description 17
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 16
- 238000011161 development Methods 0.000 claims description 16
- 239000003094 microcapsule Substances 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 14
- 229930195733 hydrocarbon Natural products 0.000 abstract description 14
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 13
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 26
- 238000005984 hydrogenation reaction Methods 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 12
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 10
- 150000002576 ketones Chemical class 0.000 description 10
- GNPWYHFXSMINJQ-UHFFFAOYSA-N 1,2-dimethyl-3-(1-phenylethyl)benzene Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=CC=CC=C1 GNPWYHFXSMINJQ-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000001465 metallisation Methods 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229910000323 aluminium silicate Inorganic materials 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 210000000981 epithelium Anatomy 0.000 description 4
- 229910052809 inorganic oxide Inorganic materials 0.000 description 4
- 150000004880 oxines Chemical class 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 239000004575 stone Substances 0.000 description 4
- 150000003505 terpenes Chemical class 0.000 description 4
- 235000007586 terpenes Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000004996 alkyl benzenes Chemical class 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 231100000572 poisoning Toxicity 0.000 description 3
- 230000000607 poisoning effect Effects 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229940053080 isosol Drugs 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000005555 metalworking Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000010742 number 1 fuel oil Substances 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001172 regenerating effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000271 synthetic detergent Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- JJQUOWCQKWDHNZ-UHFFFAOYSA-N (2,2-dimethyl-1-phenylpropyl)benzene Chemical compound C=1C=CC=CC=1C(C(C)(C)C)C1=CC=CC=C1 JJQUOWCQKWDHNZ-UHFFFAOYSA-N 0.000 description 1
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 1
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 description 1
- WFOQXUOOXMEVQB-UHFFFAOYSA-N 1-butan-2-yl-2-phenylbenzene Chemical group CCC(C)C1=CC=CC=C1C1=CC=CC=C1 WFOQXUOOXMEVQB-UHFFFAOYSA-N 0.000 description 1
- HKTCLPBBJDIBGF-UHFFFAOYSA-N 1-phenyl-2-propan-2-ylbenzene Chemical group CC(C)C1=CC=CC=C1C1=CC=CC=C1 HKTCLPBBJDIBGF-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MEUAUAYFVLVMKK-UHFFFAOYSA-N butan-2-ylbenzene;ethane Chemical compound CC.CCC(C)C1=CC=CC=C1 MEUAUAYFVLVMKK-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- MFGZXPGKKJMZIY-UHFFFAOYSA-N ethyl 5-amino-1-(4-sulfamoylphenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 MFGZXPGKKJMZIY-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 108010025899 gelatin film Proteins 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000010731 rolling oil Substances 0.000 description 1
- 238000007616 round robin method Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride 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
- C10G73/00—Recovery or refining of mineral waxes, e.g. montan wax
- C10G73/42—Refining of petroleum waxes
- C10G73/44—Refining of petroleum waxes in the presence of hydrogen or hydrogen-generating compounds
-
- 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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/02—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing
- C10G45/04—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used
- C10G45/12—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used containing crystalline alumino-silicates, e.g. molecular sieves
-
- 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
- C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
- C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Color Printing (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
To provide a method for producing a low naphthenic hydrocarbon solvent and normal chain paraffin, which comprises: (1) a step of hydrodesulfurizing a kerosene fraction, (2) a step of distilling off a gas and a light fraction and obtaining a kerosene fraction with a low sulfur content, less than 5ppm, (3) a step of separating and recovering the normal paraffin from the kerosene fraction with a molecular sieve comprising a synthetic zeolite and providing a residual oil and (4) a step of nuclearly hydrogenating the residual oil and providing the solvent with <=1 mass % of aromatic content; and varistor copying material of low naphthenic hydrocarbon solvent made by the method. The naphthenic hydrocarbon solvent has a slight malodor without exhibiting toxicity to human bodies, excellent solubility and color emissivity, which can be used as solvent of varistor copying material.
Description
The present invention relates to the manufacture method of low aromatic hydrocarbon solvents of naphthene series and straight-chain paraffin, and the pressure-sensitive copy material that uses above-mentioned hydrocarbon solvent.Relate to specifically when from kerosene(oil)fraction, making straight-chain paraffin, the content of making aromatic hydrocarbons is low, almost odorless, be applicable to the washer solvent method of low aromatic hydrocarbons of the various uses that is representative, and with above-mentioned hydrocarbon solvent as electronics for the pressure-sensitive copy material of the solvent use of property chromogenic reagent.
The petroleum-type solvent of naphthene series was as uses such as washer solvent, metal working oil, printing ink solvent, cleaning solvents in the past.
Straight-chain paraffin is extensive use of as the raw material of synthetic detergents such as soft type alkylbenzene, chloralkane, alpha-olefin in addition, and demand increases greatly in recent years.
The naphthene series petroleum solvent makes by the hydrogenation of petroleum fractions mostly, when hydrogenation is insufficient, contains a large amount of aromatic hydrocarbonss in the product that obtains.When aromatic hydrocarbons when for example alkyl benzene content is too much, residual foul smell in the product pollutes operating environment.Even hydrogenation fully carries out in addition, when straight-chain paraffin was too much, the content of naphthene series can not improve substantially yet, and solvent nature may not be good.The spy open put down in writing petroleum fractions hydrogenation in the flat 2-67396 communique after by removing the operation of normal alkane, can obtain aromatic component and be the method for the following hydrocarbon solvent of 2 weight %.But the operation of putting down in writing in the above-mentioned communique of removing normal alkane, be exactly to carry out the hydrodewaxed reaction specifically by zeolite catalyst, be removed owing to this reaction can make normal alkane decomposition or isomerization, though can obtain low aromatic hydrocarbon solvents, the yield of normal alkane reduces.
Open the spy in addition and remove normal alkane after the hydrogenated reaction of having put down in writing in the clear 63-15889 communique at kerosene(oil)fraction (nucleus hydrogenation) is carried out, can obtain containing the method for the hydrocarbon solvent of a certain amount of aromatic hydrocarbons.But because desulfurization is incomplete, the lock out operation efficient of the normal alkane of carrying out is very low thereafter.In addition, for aromatic content in the hydrocarbon solvent that contains a certain amount of aromatic hydrocarbons that aforesaid method is obtained further reduces, attempt carrying out hydrogenation reaction, but because desulfurization is incomplete, residual sulphur can cause poisoning of catalyst, so the catalyst life of hydrogenation reaction is short.
In addition, above-mentioned spy opens in the method for clear 63-15889 communique record, owing to contain a large amount of normal alkane in the kerosene(oil)fraction, for adapting to initial nuclear hydrogenation reaction process, just need handle a large amount of raw materials, so the usage quantity of hydrogen has the trend that increases.
In addition, known in the past recording materials, i.e. pressure-sensitive copy material, be by with colourless electronics for plant micro-capsule epithelium in property chromogenic reagent (to call " chromogenic reagent " in the following text) is under solution state in, be coated on then on the single face of paper; The coating acidic inorganic material is that electronics such as carboxylic acid is subjected to capacitive developer (to call " developer " in the following text) on the single face of other a piece of paper, this developer have can color development with above-mentioned chromogenic reagent reaction character.Surface with these coatings overlaps relatively in use, can obtain making carbon copies record by exerting pressure.
The manifolding recording mechanism of this recording materials is to make that the micro-capsule epithelium is destroyed under various pressure effects such as pen pressure, typewriting pressure, discharge toner solutions, thereby this chromogenic reagent is with the developer contact color development of the paper surface coated of relative configuration with it.Also known in addition a kind of recording materials are to be coated on the single face of a piece of paper and to form having various coating materials such as the micro-capsule of this color development function or developer.
The toner solutions that these recording materials use is that chromogenic reagent is dissolved in the solution that forms in the hydrophobic solvent more than a kind or 2 kinds.Hydrophobic solvent need possess following condition as used herein, that is:
1. nontoxic
2. there is not unhappy stink
3. colourless or color is extremely shallow
4. to the favorable solubility of chromogenic reagent, solution has stability
5. easily microencapsulation
6. the stability in storage of micro-capsule is good
7. do not hinder the color development reaction, color development speed is fast
8. the color development image is not sent out and is spread and sunk in, and the color development image is still distinct after the prolonged preservation
9. inexpensive.
As the chromogenic reagent solvent of this recording materials that used, for example diaryl alkane such as phenyl xylyl ethane, styroyl diphenylphosphino ethane in the past; The terphenyl of alkylnaphthalene, alkyl biphenyl, partial hydrogenation etc. contains the aromatic series hydrocarbon ils of a plurality of aromatic nucleus or chloralkane etc.But the price of these solvents is higher, and uses the chromophoric characteristic of the pressure-sensitive copy material of these solvents to satisfy the demand.Opening flat 2-47083 communique, spy the spy opens and has all proposed to use straight-chain paraffin or the clicyclic hydrocarbon method as the solvent of pressure-sensitive copy material in the flat 2-47084 communique etc.Even but exist in these methods that performance such as occurs at low temperatures look speed improves but the solvability of chromogenic reagent is relatively poor, problem such as operability difference in the production of micro-capsule.
One of purpose of the present invention, be provide stink content low, nontoxic, aromatic component content few, naphthenic to human body many, to good naphthenic hydrocarbon solvent such as the solvability of resin etc. in, a kind of method of efficient manufacturing straight-chain paraffin is provided.Other purpose is to use above-mentioned hydrocarbon solvent to solve the variety of issue that pressure-sensitive copy material in the past has, and the solvability and the good and inexpensive pressure-sensitive copy material of chromophoric characteristic of chromogenic reagent is provided.
The low aromatic hydrocarbon solvents that the 1st invention of the present invention is made up of following (1) to the operation of (4) and the manufacture method of straight-chain paraffin.
Operation (1): in the presence of catalyzer, the kerosene(oil)fraction of boiling point in 150 ℃ of-300 ℃ of scopes carried out hydrogenating desulfurization under temperature 100-400 ℃, the condition of pressure 1-20Mpa operation;
Operation (2): remove the light composition that contains gas from desulfurization resultant, obtaining sulphur content is the operation of the following kerosene(oil)fraction of 5ppm;
Operation (3): the molecular sieve of forming with synthetic zeolite separates, reclaims the operation that straight-chain paraffin makes residual oil from the kerosene(oil)fraction of sloughing sulphur; And
Operation (4): with above-mentioned residual oil in the presence of catalyzer, carry out hydrogenated (nucleus hydrogenation) reaction under temperature 50-400 ℃, the condition of pressure 1-20Mpa, make the operation of the low aromatic hydrocarbon solvents of content below 1 quality % of aromatic hydrocarbons.
The 2nd invention of the present invention is in above-mentioned the 1st manufacture method, and the monocycle alkane that contains in the above-mentioned low aromatic hydrocarbon solvents and the total amount of bicyclic alkane are more than the 40 quality %.
The 3rd invention of the present invention is the pressure-sensitive copy material that the operation by following (1) to (5) makes:
Operation (1): in the presence of catalyzer, the kerosene(oil)fraction of boiling point in 150 ℃ of-300 ℃ of scopes carried out desulfurization under temperature 100-400 ℃, the condition of pressure 1-20Mpa operation;
Operation (2): remove the light composition that contains gas from desulfurization resultant, obtaining sulphur content is the operation of the following kerosene(oil)fraction of 5ppm;
Operation (3): the molecular sieve of forming with synthetic zeolite separates, reclaims the operation that straight-chain paraffin makes residual oil from the kerosene(oil)fraction of sloughing sulphur;
Operation (4): above-mentioned residual oil in the presence of catalyzer, is carried out hydrogenated reaction under temperature 50-400 ℃, the condition of pressure 1-20Mpa, make the operation of the low aromatic hydrocarbon solvents of content below 1 quality % of aromatic hydrocarbons; And
Operation (5): the operation of making pressure-sensitive copy material with above-mentioned low aromatic hydrocarbon solvents.
The 4th invention of the present invention is in the pressure-sensitive copy material of above-mentioned the 3rd invention, and the monocycle alkane that contains in the low aromatic hydrocarbon solvents and the total amount of bicyclic alkane are more than the 40 quality %.
The 5th invention of the present invention is in the pressure-sensitive copy material of above-mentioned the 4th invention, use with electronics be subjected to the capacitive developer with contact with above-mentioned developer can color development electronics for being dissolved in the toner solutions that obtains in the solvent with the property chromogenic reagent, contain the aromatic hydrocarbons and the above-mentioned low aromatic hydrocarbon solvents that have non-condensed type more than 2 or condensed type aromatic nucleus in this solvent.
The 6th invention of the present invention is the pressure-sensitive copy material in above-mentioned the 5th invention, wrapped the micro-capsule of stating the chromogenic reagent solvent and kept the sheet support of this micro-capsule to form by interior.
Describe the present invention below in detail.
The raw material that uses in the manufacture method of the present invention is the kerosene(oil)fraction of boiling spread in 150-300 ℃ of scope.Usually contain the sulphur content about 200-1000ppm in the kerosene(oil)fraction.Because these sulphur compounds are removed in the straight-chain paraffin operation in the back, when using as sorbent material, synthetic zeolite can become the reason of poisoning of catalyst, and the reason that in aromatic hydrogenated processing, becomes the hydrogenation catalyst poisoning, so can shorten life of catalyst, cause bad influence.In addition owing to sulphur compound has reasons such as corrosive nature to equipment such as machine or pipe arrangements, so be necessary to remove sulphur compound, use catalyzer to carry out hydrodesulfurization reaction under the condition that exists by hydrogen, can change sulphur compound into hydrogen sulfide and remove.
Among the present invention, should the sulphur content in making raw material reach below the 5ppm, carry out desulphurization reaction under the condition below the preferred 1ppm.
As the catalyzer that hydrogenating desulfurization is used, sulphur content reaches below the 5ppm in the raw material of making so long as have, the sweetening power of the condition that preferred 1ppm is following, knownly in the past all can use as the employed catalyzer of hydrogenating desulfurization.For example can use at least a composition of selecting in the metallic element that belongs to periodic table of elements VI family or group VIII and its oxide compound or the sulfide etc. by the material of inorganic oxide carrier institute carrier band.
As inorganic oxide carrier, for example can use aluminum oxide, silicon-dioxide, pure aluminium silicate, crystallinity aluminosilicate, zeolite, diatomite, gac etc.As VI family metal, for example molybdenum, tungsten etc.; The group VIII metal is nickel, cobalt etc. for example.Also VI family and group VIII metal mixed can be used.
Hydrodesulfurization reaction can carry out under common condition.Be that temperature 100-400 ℃, pressure 1-20Mpa, LHSV are 0.1-10hr
-1Scope in select.What desulphurization reaction carried out beyond these condition and ranges is incomplete, so not preferred.
After the desulfurization, can separate, remove the gas that contains hydrogen sulfide and the light composition of generation by operations such as distillations.
Can obtain sulphur content by above operation is low sulphur coal oil distillate below the 5ppm.
Handle and heat up in a steamer after operation such as light composition carries out in above-mentioned hydrogenating desulfurization, use the molecular sieve of synthetic zeolite composition, can the Separation and Recovery kerosene(oil)fraction in the straight-chain paraffin of at least a portion.Because the straight-chain paraffin class is little to the chromogenic reagent solvability, so be necessary in pressure-sensitive copy material, to remove as much as possible.Promptly preferably be removed to below the 20 quality %, more preferably to 10 quality %.
Make straight-chain paraffin class isolating method from hydrocarbon mixture with molecular sieve with the operation that gas phase or liquid phase repeat to adsorb with desorb, in industry in the past, be widely used as the manufacture method of straight-chain paraffin class.
For example, the molecular sieve extraction process is to use the fixed bed of the molecular sieve of being made up of synthetic zeolite (containing many pores that are adjusted to 5 on the zeolite), with liquid phase the hocket absorption and the desorb of straight-chain paraffin class, the synthetic zeolite of absorption straight-chain paraffin class is washed with separating the low molecular weight alkanes that smokes, make the straight-chain paraffin class by desorb, thereby the low molecular weight alkanes of sneaking into is separated by distillation, and then round-robin method; TSF method (Texaco selective finishing method) be with the straight-chain paraffin class with Gas Phase Adsorption on the synthetic zeolite that has 5 pores equally, with the low molecular weight alkanes method that washing carries out desorb that flows; Isomery sieve normal alkane partition method is to use the synthetic zeolite that has 5 pores equally, carries out the absorption and the desorb of straight-chain paraffin class by alternative pressurization and decompression.It is method with the combination of vapor phase and liquid bed method that the ESSO method is arranged again, the straight-chain paraffin class is carried out under the liquid state in adsorption unit continuously in the absorption on the synthetic zeolite with 5 pores, desorb is to be higher than under the condition of adsorption temp to operate in regenerating unit, the synthetic zeolite that is reproduced is turned back in the adsorption unit to recycle then from regenerating unit.
The separation of straight-chain paraffin class of the present invention, recovery can be undertaken by above-mentioned arbitrary method.The straight-chain paraffin class of at least a portion is removed, and the residual oil that obtains is used for following operation.
The aromatic hydrocarbons that is contained in promptly separated to the straight-chain paraffin class, the residual oil that obtains after reclaiming carries out hydrogenated processing.The hydrogenation catalyst of hydrogenated use so long as can make aromatic hydrocarbons carry out getting final product of hydrogenated reaction, has no particular limits.For example can use at least a composition of selecting in the metallic element that belongs to periodic table of elements group VIII and its oxide compound or the sulfide etc. by the material of inorganic oxide carrier institute carrier band.
As inorganic oxide carrier, for example can use aluminum oxide, silicon-dioxide, pure aluminium silicate, crystallinity aluminosilicate, zeolite, diatomite, gac etc.As group VIII metal for example nickel, cobalt, platinum, rhodium, ruthenium, palladium and their mixture etc.
Hydrogenation conditions can be 0.1-30hr at temperature 50-400 ℃, pressure 1-20Mpa, LHSV
-1Scope in select.If reaction conditions is too gentle, it is insufficient that then aromatic hydrogenation carries out, and aromatic component is residual in a large number; If opposite reaction conditions is too harsh, side reactions such as hydrogenation decomposition then can take place.
After the above-mentioned hydrogenated processing, can carry out suitable distillation.
Feature by the above-mentioned low aromatic hydrocarbon solvents that obtains is mainly to be grouped into by the one-tenth of boiling point in 150-300 ℃ of scope, and aromatic composition content is below the 1 quality %.Because this aromatic component is less, stink is lower, so have superiority from improving the operating environment aspect.This puts from solvability in addition, and the total amount of preferred monocycle alkane and bicyclic alkane is more than 40 quality %.
By the straight-chain paraffin that method of the present invention obtains, the raw material that can be used as synthetic detergents such as soft type alkylbenzene, chloralkane, alpha-olefin uses.
In addition, the naphthene series that the inventive method obtains hangs down aromatic hydrocarbon solvents, be applicable to headed by the washer solvent, metalworking fluid, lubricating oil, machining oil, ROLLING OIL, compacting oil, printing ink be with various uses such as solvent, cleaning solvents, also has good performance as pressure-sensitive copy material described below.
In the present invention promptly, the solvent that above-mentioned low aromatic hydrocarbon solvents is used as dissolving chromogenic reagent in the pressure-sensitive copy material can be used, also can merge and use with other solvent.Merging when using with the aromatic hydrocarbon solvents that contains non-condensed type more than 2 or condensed type aromatic ring, preferred composition is, low aromatic hydrocarbon solvents is 5-50 quality %, and boiling point is that aromatic hydrocarbon solvents more than 260 ℃, that contain non-condensed type more than at least 2 or condensed type aromatic nucleus is 50-95 quality %.
When aromatic hydrocarbon solvents surpasses 95 quality %, there be not the improvement effect of discovery to color emissivity, price can not reduce yet.Solvability owing to chromogenic reagent when being lower than 50 quality % is little, so also not preferred.
As the above-mentioned hydrocarbon solvent that contains non-condensed type more than 2 or condensed type aromatic nucleus, for example phenyl xylyl ethane, styroyl diphenylphosphino ethane, phenyl trimethylphenyl ethane, phenyl-diaryl alkanes such as sec-butylbenzene methylmethane; Alkylnaphthalenes such as diisopropylnaphthalene; Terphenyl of alkyl biphenyls such as sec-butyl biphenyl, isopropyl biphenyl or dichloro alkyl biphenyl, partial hydrogenation etc.
As the developer that pressure-sensitive copy material of the present invention uses, the material of preference as selecting the group of forming from the mixture of aromatic carboxylic acid, its polymer, its metal-salt, the carboxy-modified terpene phenolic resin of polyvalent metalization and its derivative and these materials.
In addition, use the normally used phenolic novolac of developer of in the past copy material, particularly pressure-sensitive copy material etc.,, also can't obtain the good pressure-sensitive carbon paper of color development speed even use solvent compositions of the present invention.
At this aromatic carboxylic acid as developer, it can be the direct and aromatic nucleus (monocycle of carboxyl, many rings all can) the bonded organic compound, concrete example such as salicyclic acid derivatives are as 3,5-two-(α-Jia Jibianji) Whitfield's ointment, 3-(α-Jia Jibianji)-5-(α, α '-dimethyl benzyl) Whitfield's ointment, 3-(4 '-α, α '-dimethyl benzyl) phenyl-5-(α, α '-dimethyl benzyl) Whitfield's ointment, 3, the 5-di-tert-butyl salicylic acid, 3,5-two uncle's octyl group Whitfield's ointments, 3-cyclohexyl-5-(α, α '-dimethyl benzyl) Whitfield's ointment, 3-phenyl-5-(α, α '-dimethyl benzyl) Whitfield's ointment, 3,5-two-(α, α '-dimethyl benzyl) Whitfield's ointment etc.The aromatic carboxylic acid of addition styrenic is in for example vinylbenzene Whitfield's ointment etc. is also included within addition.
Particularly preferred aromatic carboxylic acid is that the total number of carbon atoms is at the aromatic carboxylic acid more than 15.But there is no particular limitation to carbonatoms during as cocondensation of putting down in writing below or copolymerization monomer use.Can so that in order to aromatic carboxylic acid particularly Whitfield's ointment as monomeric condensation of condensation or cocondensation resin.As the cocondensation resin polymkeric substance etc. of the cocondensation resin that forms of Whitfield's ointment and dialkoxy dimethylbenzene, Whitfield's ointment and aldehyde formation for example.Also can add trialkyl benzene etc. therein again as the cocondensation monomer.
Also can use these aromatic carboxylic acids or its polymeric metal-salt.
As metal-salt, polyvalent metal salts such as zinc, aluminium, barium, tin, iron, calcium, lead for example.
As the carboxy-modified terpene phenolic resin of polyvalent metalization, can in the presence of an acidic catalyst,, utilize well-established law to import carboxyl more in addition, resultant metal multivalenceization is made ring-type monoterpene class and phenol condensation.For example the spy opens clear 62-19486 communique record, the condensation under the boron trifluoride catalyst effect of phenol and α-Pai Xi, then in that to import carbonic acid gas in the presence of the sodium Metal 99.5 on the cocondensation resin carboxylated, undertaken polyvalent metalization by zinc chloride etc. then, make thus and obtain the carboxy-modified terpene phenolic resin of polyvalent metalization.Polyvalent metal also can use zinc, aluminium, barium, tin, iron, calcium, lead etc. in this case, preferred zinc.
The aromatic carboxylic acid, its polymkeric substance, its metal-salt and the carboxy-modified terpene phenolic resin of polyvalent metalization that use as developer also can mix use.Mixing can be by carrying out in solvent or in dispersion medium, or obtain by melting mixing.
Chromogenic reagent as pressure-sensitive copy material of the present invention uses can use as materials such as triarylmethane system, diphenylmethane, naphthazin(e) system, thiazine system, volution pyrans systems.
Be chromogenic reagent for example 3 specifically as triarylmethane, 3-two (right-dimethylaminophenyl)-6-dimethylamino phthalein ketone (crystal violet lactone, to call CVL in the following text), 3,3-two (right-dimethylaminophenyl) phthalein ketone, 3-(right-dimethylaminophenyl)-3-(1,2-dimethyl indole-3-yl) phthalein ketone, 3-(right-dimethylaminophenyl)-3-(2 methyl indole-3-yl) phthalein ketone, 3-(right-dimethylaminophenyl)-3-(2-phenylindone-3-yl) phthalein ketone, 3,3-two (1,2-dimethyl indole-3-yl)-5-dimethylamino phthalein ketone, 3,3-two (1,2-dimethyl indole-3-yl)-6-dimethylamino phthalein ketone, 3,3-two (9-ethyl carbazole-3-yl)-5-dimethylamino phthalein ketone, 3,3-two (2-phenylindone-3-yl)-5-dimethylamino phthalein ketone, 3-is right-dimethylaminophenyl-3-(1-methylpyrrole-2-yl)-6-dimethylamino phthalein ketone etc.
As the diphenylmethane chromogenic reagent, for example 4,4 '-two (dimethylamino) phenyl (benzhydrin) benzylic ether, the colourless alkali Huang of N-halogenophenyl, N-2,4, the colourless alkali Huang of 5-trichlorophenyl etc.
As naphthazin(e) is for example rhodamine B-anilino lactan of chromogenic reagent; rhodamine B-(p-Nitraniline base) lactan; rhodamine B-(right-chloroanilino) lactan; 3-dimethylamino-6-methoxyl group fluorane; 3-diethylamino-7-methoxyl group fluorane; 3-diethylamino-7-chloro-6-methyl fluoran; 3-diethylamino-7-(ethanoyl methylamino) fluorane; 3-diethylamino-7-(dibenzyl amino) fluorane; 3-diethylamino-7-(methyl-benzyl amino) fluorane; 3-diethylamino-7-(chloroethyl methylamino) fluorane; 3-diethylamino-7-(diethylamino) fluorane; 3-diethylamino-6-methyl-7-anilino fluorane etc.
As thiazine is for example benzoyl leucomethylene blue, right-nitrobenzyl leucomethylene blue etc. of chromogenic reagent.
As the volution pyrans is for example 3-methyl-volution-dinaphthopyran, 3-ethyl-volution-dinaphthopyran, 3 of chromogenic reagent, 3 '-two chloro-volution-dinaphthopyrans, 3-benzyl-volution-dinaphthopyran, 3-methyl-naphtho--(3-methoxyl group benzo)-volution pyrans, 3-propyl group-volution-dibenzo two pyrans etc.
The following describes for example general manufacture method of pressure-sensitive carbon paper of pressure-sensitive copy material of the present invention.The ratio of above-mentioned chromogenic reagent in 1-10 quality % is dissolved in the above-mentioned solvent, solution emulsification in the mixed aqueous solution of gelatin and gum arabic is disperseed, around the emulsive oil droplet, form gelatin film by coacervation then and carry out microencapsulation.Recently In-Situ polymerization, surface aggregate method etc. also are being extensive use of with the method that synthetic resins carries out microencapsulation.
The capsule emulsion of the trickle oil droplet that forms thus is coated on the paper as sheet support, the paper relative or above-mentioned coated face with coated face originally on one's body, stratiform is coated with above-mentioned developer, can make pressure-sensitive copy materials such as pressure-sensitive carbon paper thus.
Specify the present invention below by embodiment and comparative example.
Embodiment 1,2
With boiling point is after the 193-253 ℃ of kerosene(oil)fraction in the scope carries out hydrogenating desulfurization with the Ni-W catalyzer, to heat up in a steamer degas body and light composition, obtains the following low sulphur coal oil distillate of sulphur content 5ppm.
Use the molecular sieving of forming by synthetic zeolite to reclaim straight-chain paraffin then.Because the result of above-mentioned desulfurization makes that sulphur content content is very low in the raw material, removes so can separate efficiently by zeolite molecular sieve.
Then, press the condition shown in the table 1 with Ni/ diatomite catalyzer, the residual oil after straight-chain paraffin is separated carries out hydrogenated processing.Carry out so hydrogenated reaction can for a long time stablize owing to sulphur content content in the raw material is low this moment.
The solvent proterties that obtains is as shown in table 1.
Embodiment 3
Reaction solution after the hydrogenated processing that embodiment 1 is obtained distills by the precise distillation device, obtains boiling point 203-220 ℃ cut, as solvent cut.The result is as shown in table 1.
Comparative example 1
Remove the recovery and the hydrogenated treatment process of not carrying out straight-chain paraffin, other carries out equally by embodiment 2, and the result is as shown in table 1.
The modulation of table 1 solvent
| Project | Embodiment | Comparative example | ||
| 1 | 2 | 3 | 1 | |
| Hydrogenated condition temperature (℃) pressure (MPa) LHSV (hr -1) | 150 2.5 5 | 200 2.5 5 | 200 2.5 5 | - - - |
| The proterties boiling spread of solvent (℃) composition (quality %) monocycle alkane bicyclic alkane aromatic series | 193～252 36 37 0.3 | 193～below 252 36 37 0.1 | 203～below 220 36 42 0.1 | 193～252 17 18 7.1 |
The stink evaluation test of solvent
By totally 10 of the good men and women of state of health, estimate the solvent of embodiment 1-3 and comparative example 1, estimate and divide 5 class by following standard.Mean value is as shown in table 2.
1, odorless; 2, frowziness slightly; 3, frowziness; 4, stink is very heavy; 5, stink is strong
The stink test of table 2 solvent
| Project | Embodiment | Comparative example | ||
| 1 | 2 | 3 | 1 | |
| The stink of solvent | 2.2 | 2.0 | 1.5 | 3.5 |
Embodiment 4, comparative example 2-4
The dissolubility test of chromogenic reagent
In mixed solvent (embodiment 4) 20g of low aromatic hydrocarbon solvents 20 quality % that embodiment 3 obtains and bicyclic aromatic hydrocarbon phenyl xylyl ethane (day stone Highsol SAS-296) (trade(brand)name, Japan petroleum chemistry (strain) system) 80 quality %, add the chromogenic reagent CVL of the blue usefulness of 5g, heat dissolving after 16 hours, measure meltage with Fourier transform infrared spectrophotometer (FT-IR).The solvability of chromogenic reagent is represented with the color development dosage (g) of every 100g dissolution with solvents.
As a comparative example, mix with day stone SAS-296 respectively with straight-chain paraffin solvent Normal paraffin H (trade(brand)name, Japan petroleum chemistry (strain) system) and isoparaffic solvent Isosol (trade(brand)name, Japan petroleum chemistry (strain) system), mixed solvent (comparative example 2,3) is carried out same evaluation.The result is as shown in table 3.
Use favorable solubility when hanging down aromatic hydrocarbon solvents among the present invention
The solvability of table 3 chromogenic reagent
| Project | Embodiment 4 | Comparative example | ||
| 2 | 3 | |||
| Low aromatic hydrocarbon solvents (embodiment 3) | 20 | - | - | |
| Solvent mixing ratio (quality %) | Normal paraffin H | - | 20 | - |
| Isosol 400 | - | - | 20 | |
| Day stone Highsol SAS-296 | 80 | 80 | 80 | |
| Chromogenic reagent solvability (g/100g) | 40℃ | 1.01 | 0.88 | 0.84 |
| 70℃ | 2.58 | 2.20 | 2.07 | |
| 100℃ | 8.01 | 7.13 | 6.61 | |
The evaluation of chromophoric characteristic
In the mixed solvent of the foregoing description 4, dissolving CVL5 quality %, the solution that obtains adopts In-Situ polymerization (using urea and formaldehyde) to carry out microencapsulation, in the micro-capsule emulsion that obtains, add thickener and retention agent, use the inferior roller of plum to be coated on the vellum, obtain page paper of going up of pressure-sensitive carbon paper.
As developer, prepare to be coated with 3, the nextpage paper of 5-two (α-Jia Jibianji) zinc salicylate, page or leaf paper and nextpage paper make the micro-capsule coated face relative with developer in the coincidence, use impact type printing press color development down at low temperature (3 ℃).
(impact the back) behind the color development,, obtain coloring intensity with the reflectivity of the nextpage paper of reflective spectrophotometer mensuration after 3 seconds-120 seconds.
As a comparative example, when separately phenyl xylyl ethane being used as solvent (comparative example 4), estimate equally.The result provides in table 4.
Use the present invention of low aromatic hydrocarbons, compare with the independent situation of phenyl xylyl ethane under low temperature (3 ℃), the coloring intensity at initial stage is big, and low temperature color development speed at short notice is good.
Table 4 coloring intensity
| Project | Embodiment 4 | Comparative example 4 |
| Time (second) | Low aromatic hydrocarbon solvent cooperates | Day stone Highsol SAS-296 is independent |
| 3 5 10 20 60 120 | 49.39 52.70 56.94 61.10 67.47 71.31 | 46.8 50.13 54.45 58.77 65.38 69.33 |
Low aromatic hydrocarbon solvents of the present invention has that foul smell is few, the dissolubility of colour former is good and as the performance of pressure-sensitive copy material, the particularly good characteristics of color development speed. That is to say that low aromatic hydrocarbon solvents of the present invention and pressure-sensitive copy material have following feature.
1) poison;
2) cheapness;
3) undesirable foul smell is few;
4) dissolubility of colour former is better than other solvent;
5) during microencapsulation, form stable small dispersion;
6) on the surface of above-mentioned dispersion, may form the micro-capsule epithelium;
7) storage of micro-capsule has good stability;
8) can be on oil droplet evenly and with desirable thickness coating micro-capsule epithelium;
9) do not hinder the color reaction that is produced by colour former and developer, and color development speed is fast;
10) when being coated with paper as the macromolecular material of developer and contacting, macromolecular material also dissolves, and can make tightr with contacting of colour former;
11) chromophore image immaculate, and distinct;
12) can obtain distinct chromophore image after the long preservation.
Claims (6)
1. the manufacture method of low aromatic hydrocarbon solvents and straight-chain paraffin is made up of following (1) to the operation of (4),
Operation (1): hydrogenating desulfurization with catalyzer in the presence of, the kerosene(oil)fraction of boiling point in 150 ℃ of-300 ℃ of scopes carried out hydrogenating desulfurization under temperature 100-400 ℃, the condition of pressure 1-20Mpa operation;
Operation (2): remove the light composition that contains gas from desulfurization resultant, obtaining sulphur content is the operation of the following kerosene(oil)fraction of 5ppm;
Operation (3): the molecular sieve of forming with synthetic zeolite separates from the kerosene(oil)fraction of sloughing sulphur, reclaims straight-chain paraffin, makes the operation of residual oil simultaneously; And
Operation (4): above-mentioned residual oil in the presence of hydrogenated catalyzer, is carried out hydrogenated reaction under temperature 50-400 ℃, the condition of pressure 1-20Mpa, make the operation of the low aromatic hydrocarbon solvents of content below 1 quality % of aromatic hydrocarbons.
2. the manufacture method of claim 1 record, containing monocycle alkane and bicyclic alkane total amount in the wherein above-mentioned low aromatic hydrocarbon solvents is more than the 40 quality %.
3. pressure-sensitive copy material is made by the operation of following (1) to (5):
Operation (1): in the presence of catalyzer, the kerosene(oil)fraction of boiling point in 150 ℃ of-300 ℃ of scopes carried out desulfurization under temperature 100-400 ℃, the condition of pressure 1-20Mpa operation;
Operation (2): remove the light composition that contains gas from desulfurization resultant, obtaining sulphur content is the operation of the following kerosene(oil)fraction of 5ppm;
Operation (3): the molecular sieve of forming with synthetic zeolite separates from the kerosene(oil)fraction of sloughing sulphur, reclaims straight-chain paraffin, makes the operation of residual oil simultaneously;
Operation (4): above-mentioned residual oil in the presence of hydrogenated catalyzer, is carried out hydrogenated reaction under temperature 50-400 ℃, the condition of pressure 1-20Mpa, make the operation of the low aromatic hydrocarbon solvents of content below 1 quality % of aromatic hydrocarbons; And
Operation (5): the operation of making pressure-sensitive copy material with above-mentioned low aromatic hydrocarbon solvents.
4. the pressure-sensitive copy material of claim 3 record, containing monocycle alkane and bicyclic alkane total amount in the wherein above-mentioned low aromatic hydrocarbon solvents is more than the 40 quality %.
5. the pressure-sensitive copy material of claim 4 record, it is characterized in that using with electronics be subjected to the capacitive developer with contact with this developer can color development electronics for being dissolved in the toner solutions that obtains in the solvent with the property chromogenic reagent, contain the aromatic hydrocarbons and the above-mentioned low aromatic hydrocarbon solvents that have non-condensed type more than 2 or condensed type aromatic nucleus in this solvent.
6. the pressure-sensitive copy material of claim 5 record is wrapped the micro-capsule of stating toner solutions and is kept the sheet support of this micro-capsule to form by interior.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000113087A JP2001294871A (en) | 2000-04-14 | 2000-04-14 | Method for producing low-aromatic hydrocarbon solvent and normal chain paraffin |
| JP113087/2000 | 2000-04-14 | ||
| JP2000381131A JP2002178635A (en) | 2000-12-15 | 2000-12-15 | Pressure sensitive copying material |
| JP381131/2000 | 2000-12-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1318620A CN1318620A (en) | 2001-10-24 |
| CN1320081C true CN1320081C (en) | 2007-06-06 |
Family
ID=26590113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011163887A Expired - Fee Related CN1320081C (en) | 2000-04-14 | 2001-04-13 | Prep. of low aromatic hydrocarbon solvent, straight-chain paraffin and pressure-sensitive copy material |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR100697676B1 (en) |
| CN (1) | CN1320081C (en) |
| MY (1) | MY140048A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4576334B2 (en) * | 2003-03-07 | 2010-11-04 | Ｊｘ日鉱日石エネルギー株式会社 | Hydrotreating process for diesel oil fraction |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4795840A (en) * | 1986-07-04 | 1989-01-03 | Nippon Petrochemicals Co., Ltd. | Method for preparing hydrocarbon mixture solvent |
| JPH11129614A (en) * | 1997-10-31 | 1999-05-18 | Sanko Chem Co Ltd | Developer composition and pressure sensitive recording material using it |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2556311B2 (en) | 1986-07-04 | 1996-11-20 | 日本石油化学株式会社 | Process for producing hydrocarbon mixture solvent |
-
2001
- 2001-03-19 KR KR1020010014022A patent/KR100697676B1/en not_active IP Right Cessation
- 2001-03-20 MY MYPI20011307A patent/MY140048A/en unknown
- 2001-04-13 CN CNB011163887A patent/CN1320081C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4795840A (en) * | 1986-07-04 | 1989-01-03 | Nippon Petrochemicals Co., Ltd. | Method for preparing hydrocarbon mixture solvent |
| JPH11129614A (en) * | 1997-10-31 | 1999-05-18 | Sanko Chem Co Ltd | Developer composition and pressure sensitive recording material using it |
Also Published As
| Publication number | Publication date |
|---|---|
| MY140048A (en) | 2009-11-30 |
| CN1318620A (en) | 2001-10-24 |
| KR20010098410A (en) | 2001-11-08 |
| KR100697676B1 (en) | 2007-03-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1020919C (en) | Process for production of white oils from heavy alkylate by-product | |
| KR20060127401A (en) | Ring opening for increased olefin production | |
| NZ207880A (en) | Catalytic hydrocracking of a hydrocarbon feedstock having a propensity to form polynuclear aromatic compounds | |
| EP2439254A2 (en) | Improved hydrocarbon fluids | |
| US3806463A (en) | Microcapsules for carbonless copying paper | |
| CN1024674C (en) | Selective hydrogenation process for improving color and color stability of hydrocarbon fraction | |
| CN1320081C (en) | Prep. of low aromatic hydrocarbon solvent, straight-chain paraffin and pressure-sensitive copy material | |
| TWI646186B (en) | Process for hydrogenation of a hydrocarbon feedstock comprising aromatic compounds | |
| EP0255871B1 (en) | Use of a hydrocarbon mixture as solvent | |
| CA2223651C (en) | Process for the hydrogenation of a thiophenic sulfur containing hydrocarbon feed | |
| US4289806A (en) | Pressure-sensitive recording material | |
| CN1169336A (en) | Refined catalyst made by distillate added with hydrogen and preparation thereof | |
| EP1552881B1 (en) | Catalyst for petroleum resin hydrogenation and process for producing hydrogenated petroleum resin | |
| JPH07121612B2 (en) | Copy material | |
| CN1282341A (en) | Process for hydrogenation of macromolecular organic substrates | |
| US4039712A (en) | Process for producing a solvent for use in microcapsule for pressure-sensitive copying paper | |
| CN1041385A (en) | From the aromatics materials flow, remove the method for impurity | |
| EP0601690B1 (en) | Solvent for use in carbonless paper, comprising diisopropylbiphenyl and triisopropylbiphenyl, and products utilising the same | |
| JP2002178635A (en) | Pressure sensitive copying material | |
| CA1310667C (en) | Microcapsules of pressure-sensitive copying paper | |
| JPH07121611B2 (en) | Copy material | |
| CN1195718C (en) | Hydrocarbon solvent and pressure-sensitive copying material made with the same | |
| CN1793310B (en) | Solvent composite for newspaper ink and its preparation method | |
| DE2141194A1 (en) | Pressure-sensitive copier papers with a new solvent for the color former | |
| WO2007066915A1 (en) | Environment-friendly hydrocarbon solvent composition removed normal hexane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20070606 Termination date: 20200413 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |