CN1257194C - Oil soluble frictional reducing polymer and preparing method thereof - Google Patents
Oil soluble frictional reducing polymer and preparing method thereof Download PDFInfo
- Publication number
- CN1257194C CN1257194C CN 02148773 CN02148773A CN1257194C CN 1257194 C CN1257194 C CN 1257194C CN 02148773 CN02148773 CN 02148773 CN 02148773 A CN02148773 A CN 02148773A CN 1257194 C CN1257194 C CN 1257194C
- Authority
- CN
- China
- Prior art keywords
- drag reducing
- oil soluble
- reducing polymer
- zirconium
- monomer
- 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
- 229920000642 polymer Polymers 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 239000000178 monomer Substances 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 12
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical group C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000007789 sealing Methods 0.000 claims abstract description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005977 Ethylene Substances 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000007172 homogeneous catalysis Methods 0.000 claims abstract 2
- 150000001336 alkenes Chemical class 0.000 claims description 10
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 9
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
- 239000010936 titanium Substances 0.000 claims description 9
- 229910052719 titanium Inorganic materials 0.000 claims description 9
- 150000003624 transition metals Chemical class 0.000 claims description 9
- 229910052726 zirconium Inorganic materials 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- UCIKZESDXASJNG-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C([Zr+2])C=CC2=C1 Chemical class [Cl-].[Cl-].C1=CC=C2C([Zr+2])C=CC2=C1 UCIKZESDXASJNG-UHFFFAOYSA-L 0.000 claims description 3
- DDDRMZMSFMQPPC-UHFFFAOYSA-L [Cl-].[Cl-].C1C=CC=C2C([Zr+2])CCC21 Chemical class [Cl-].[Cl-].C1C=CC=C2C([Zr+2])CCC21 DDDRMZMSFMQPPC-UHFFFAOYSA-L 0.000 claims description 3
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 230000009514 concussion Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- -1 cyclopentadienyl titanium transition metal Chemical class 0.000 abstract description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 3
- JFWBIRAGFWPMTI-UHFFFAOYSA-N [Zr].[CH]1C=CC=C1 Chemical compound [Zr].[CH]1C=CC=C1 JFWBIRAGFWPMTI-UHFFFAOYSA-N 0.000 abstract 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 2
- 239000004711 α-olefin Substances 0.000 abstract 2
- YVSMQHYREUQGRX-UHFFFAOYSA-N 2-ethyloxaluminane Chemical compound CC[Al]1CCCCO1 YVSMQHYREUQGRX-UHFFFAOYSA-N 0.000 abstract 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 abstract 1
- QOXHZZQZTIGPEV-UHFFFAOYSA-K cyclopenta-1,3-diene;titanium(4+);trichloride Chemical compound Cl[Ti+](Cl)Cl.C=1C=C[CH-]C=1 QOXHZZQZTIGPEV-UHFFFAOYSA-K 0.000 abstract 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 abstract 1
- 230000000977 initiatory effect Effects 0.000 abstract 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 abstract 1
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 15
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 4
- 238000012662 bulk polymerization Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- 206010024769 Local reaction Diseases 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical group CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
Number of times by the test pipeline section | Drag reducing efficiency | |||
Example 1 | Example 2 | Example 3 | Example 4 | |
1 | 31.3% | 35.5% | 29.2% | 33.6% |
2 | 28.5 | 32.2 | 27.4 | 31.5 |
3 | 26.7 | 29.5 | 26.2 | 30.6 |
4 | 25.8 | 27.6 | 25.6 | 30.1 |
5 | 25.0 | 26.2 | 25.2 | 29.8 |
6 | 24.8 | 25.7 | 24.9 | 29.6 |
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 02148773 CN1257194C (en) | 2002-11-19 | 2002-11-19 | Oil soluble frictional reducing polymer and preparing method thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 02148773 CN1257194C (en) | 2002-11-19 | 2002-11-19 | Oil soluble frictional reducing polymer and preparing method thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1500814A CN1500814A (en) | 2004-06-02 |
CN1257194C true CN1257194C (en) | 2006-05-24 |
Family
ID=34233326
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 02148773 Expired - Fee Related CN1257194C (en) | 2002-11-19 | 2002-11-19 | Oil soluble frictional reducing polymer and preparing method thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1257194C (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102453297B (en) * | 2010-10-28 | 2013-10-16 | 中国石油天然气股份有限公司 | Supermolecular polymer drag reduction agent for oil products and preparation method thereof |
CN109593153B (en) * | 2018-12-19 | 2021-05-28 | 沈阳宏城精细化工科技有限公司 | Preparation method of modified poly-alpha-olefin |
GB201901496D0 (en) | 2019-02-04 | 2019-03-27 | Innospec Ltd | Chemical reactions |
GB201901503D0 (en) | 2019-02-04 | 2019-03-27 | Innospec Ltd | Chemical reactions |
CN113004644B (en) * | 2021-03-01 | 2021-12-24 | 山东大学 | Associative oil-soluble high polymer drag reducer and application thereof |
-
2002
- 2002-11-19 CN CN 02148773 patent/CN1257194C/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CN1500814A (en) | 2004-06-02 |
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C06 | Publication | ||
PB01 | Publication | ||
ASS | Succession or assignment of patent right |
Owner name: CHINA NATIONAL PETROLEUM CORP. Free format text: FORMER OWNER: SINO OIL KING SHINE CHEMICAL CO., LTD., LANGFANG DEVELOPMENT ZONE Owner name: CHINA PETROLEUM PIPELINE BUREAU Effective date: 20040611 |
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C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20040611 Address after: 100724, Xicheng District, Beijing six shop pit No. 6 Applicant after: China National Petroleum Corp. Co-applicant after: CHINA PETROLEUM PIPELINE BUREAU Address before: Jin Yuan Road, Langfang Economic Development Zone, Langfang, Hebei Applicant before: SINO OIL KING SHINE CHEMICAL C |
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C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CP03 | Change of name, title or address |
Address after: 100007 Dongzhimen North Street, Dongcheng District, Dongcheng District, Beijing Co-patentee after: China Petroleum and Natural Gas Pipeline Bureau Co.,Ltd. Patentee after: CHINA NATIONAL PETROLEUM Corp. Address before: 100724, Xicheng District, Beijing six shop pit No. 6 Co-patentee before: CHINA PETROLEUM PIPELINE BUREAU Patentee before: China National Petroleum Corp. |
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CP03 | Change of name, title or address | ||
TR01 | Transfer of patent right |
Effective date of registration: 20190226 Address after: 100007 Dongzhimen North Street, Dongcheng District, Dongcheng District, Beijing Co-patentee after: China Petroleum Pipeline Engineering Co.,Ltd. Patentee after: CHINA NATIONAL PETROLEUM Corp. Co-patentee after: SINO OIL KING SHINE CHEMICAL C Address before: 100007 Dongzhimen North Street, Dongcheng District, Dongcheng District, Beijing Co-patentee before: China Petroleum and Natural Gas Pipeline Bureau Co.,Ltd. Patentee before: CHINA NATIONAL PETROLEUM Corp. |
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TR01 | Transfer of patent right | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20060524 Termination date: 20211119 |
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CF01 | Termination of patent right due to non-payment of annual fee |