TONG HOP CHAT QC CHE QUA TRINH POLYMER HOA CAC SAN PHAM LONG CUA QUA TRINH NHIET PHAN HYDROCARBON PHAN DOAN X A N G
TU LIGNIN BANG H 6 N HOP NATRIUM NITRITE VA NATRIUM NITRATE
TS. Dam Thj Thanh Hai, TS. Do Chiem Tai, TS. Ho^ng Thjnh NhSn Dgi hgc Ddu khi Viit Nam
TSKH. A.F.Gogatov
Viin Hda hUuca- Viin Hdn Idm Khoa hoc bin bang Nga
Tom t i t
Bdi bdo gidi thiiu nghiin cdu khd ndng tdng hap chdt dc che dgng nitrolignin deUc che qud trinh polymer hda cdc sdnphdm ldng (pyrocondensate) cua qud trinh nhiit phdn hydrocarbon phdn dogn xdng tgi Nbd mdy sdn xudt polymer Angarsk, Liin bang Nga. Nitrolignin duac tong hap bdng phuang phdp nitro bda kraft-lignin tdhdn hap natrium nitrite vd natrium nitrate. Ket qud thUe nghiim cho thdy nitrolignin kim bdm qud trinh polymer hda cdc hap chdt khdng noc6 trong pyrocondensate hiiu qud han ionol (2,6-di-tert-butyl-4-metbylpbenol) - chdt dc che dang duac sddung tgi tdhdp
"EP-300"cua Nhd mdy sdn xudt polymer Angarsk.
1. Gidi thieu
Phin Ung trimg hop ed vai trd ri't quan trpng trong sin xuat polymer. Tuy nhidn, diy lai l i phin Ung khdng mong mudn xiy ra trong qui trinh sin xuat, van ehuyen v i lifu trU monome (ethylene, propylene, butadiene, stirene) cd dd tinh khilt eao. Dudi tie dung eiia nhidt dp (nhat la d nhidt dp eao), eie monome tham gia phin Ung trung hop tao thanh eac polymer, ling dpng trdn be mat thilt bj trong diy ehuyen edng nghd va dUdng dng dan; lam giim khi ning hoat ddng ciia thilt bj, giam chat lUpng v i hieu q u i kinh t l eua Nha miy sin xuat [1]. Do do, ngan chin hoic giim thid'u kha ning xiy ra qui trinh polymer hda la van d l quan trpng trong nginh edng nghidp hda dau v i sin xuat monome [2].
Oi thife hidn mue dich nay, cic n h i may tai My, Lien bang Nga thudng sif dung chat Ue c h l q u i trinh polymer hda (cdn gpi la inhibitor). Cic chat niy sd phin Ung vdi cie gdc tu do, tao thinh hop chat thap phin tif hoae cie gde t u do khie khdng ed khi nang tham gia vao phin Ung trung hop. Hidn nay, trdn t h i gidi sd luong chat Uc c h l dupe nghien eUu v i d l xuat ifng dung rat Idn. Tuy nhiln, thifc t l sif dung chat Ue c h l trong eie nha miy sin xuit tai Lidn bang Nga nhilu n i m qua eho thay, cie hop chat dang phenol la chat ifc c h l phd b i l n nhat, cd hilu q u i Uc c h l v i khi ning eanh tranhcao[1,3, 4, 5].
Theo nghien cUu cua Nha may Angarsk, ehi phi di Ue chl qua trinh polymer hda chilm khoing 6% tdng ehi phi sin xuat monome [6]. Vi viy, ngUdi ta thudng tim kilm cic hop chat ed hoat tinh Ue c h l eao, gii thinh re, 6i giim chi phi v i ning eao hidu q u i kinh t l . Trong do, eae nhi nghidn eUu hudng sU quan t i m d i n viec sif dung eie sin pham phu hoae chat t h i i eiia mpt sd nhel may sin xuat khae.
Kraft-lignin (KL) l i chat t h i i cua q u i trinh chl biln gft va sin xuat cellulose vdi thinh phan hda hpe l i polymer dang phenol. Kraft-lignin dupe coi l i ngudn nguyen Hlu t i i tao tiem ning (vdi gii thanh thap) eho qui trinh tdng hpp eie hop chat dang phenol cd hidu qui Ue chl (hoat tinh Ue chl) eao, die biet la d Lidn bang Nga, noi ed ngudn tai nguydn rUng rat phong phU.
Trong bai b i o nay, nhdm tie gii trinh biy qui trinh tdng hop chat Ue c h l cd hidu qui eao dang nitrolignin tU kraft-lignin bang hdn hop natrium nitrite v i natrium nitrate; k i t qui dinh g i i thuc nghidm hidu qui ifc chl cOa sin pham tren sin phim Idng pyrocondensate.
2. Thuc nghiem
2.1. Ddi tuang, pbUOng phdp tdng hap nitrolignin Trong nghien cdu niy, nhdm tic gii t i l n hanh thtfC nghidm va dinh g i i hoat tinh Uc c h l q u i trinh polymer hda dudi tic ddng cda nhidt dd cao cua hpp chit
4 2 oAUKHi so 4/2013
PETROVIETNAM
£(%) = nitrolignin trdn pyrocondensate K-27. Odi tuong nghien
eUu: pyrocondensate thudc thip chung cat K-27 cue Nha miy sin xuit polymer EP-300 thude td hop Nha may Ipe hda d i u Angarsk, Tp. Angarsk, Lidn bang Nga (gpi t i t l i K-27). Cie tinh chit eo bin eiia pyrocondensate K-27 dUOc trinh biy trong Bing 1:
Phuong phip tdng hop nitrolignin: trdn mdt lupng nhat djnh kraft-lignin vdi dung djeh hdn hpp mudi natrium nitrite v i natrium nitrate (ty Id mol eiia natrium nitrite v i natrium nitrate la 1:1). Dun hdn hop trdn b i p hoi nude v i giU nhidt dp phan Ung d 40 - 50°C trong thdi gian 1 gid (trong qui trinh dun khdng khuay hdn hop de trinh hidn tuong tao bpt). Sau dd, lim ngudi hdn hpp d nhidt dd phdng, Ipc v i sly khd nitrolignin.
2.2. Ddnh gid khd ndng dc che qud trinh polymer bda Phuong phip djnh luong dinh gii hoat tinh Ue ehe qui trinh polymer hda cic hop chat khdng no cd trong pyrocondensate l i so sanh khdi lupng polymer tao thanh sau qui trinh xif ly nhidt trong trUdng hop sU dung chit Ue chl vdi trudng hop khdng sif dung. Qua trinh thuc nghidm duoe thue hidn trdn miy "nOC-77M" theo Tidu ehuan FOCT 8489-85 eua Lidn bang Nga "PhUong phip xac djnh ham luong nhua theo Bu-da-rov" [7]. Phuong phip nay d i dupe chuan hda v i i p dung de dinh gii chat luong cac sin pham trung gian trong td hop Nhi miy Ipc dau va sin xuat polymer. Cie thi nghidm duoc tiln hinh d dieu kidn tuong tudilu kiln thuc t l tai cae nhi miy Ipe hda dau.
Thi nghidm m l u gdm eac budc sau:
Od 100ml pyrocondensate vio binh phan Ung ehju i p suit, eho them chat ifc c h l vio binh vdi khdi lupng 0,01 - 0,05%wt so vdi pyrocondensate. Ddng kin binh v i d i t vio bd dn nhiet bing dau d i dun ndng den nhidt dd 130''C. GiU nhidt dp dn djnh d mUc niy trong 1 gid, sau dd lay binh ra v i lim ngudi tdi nhidt dd phdng.
a pyrocondensate K-27 Pyrocondensate K-27
Chung eat pyrocondensate d i de ngudi bang hoi nudc d nhidt dp IdO^C trdn thilt bj "nOC-77M"va do khdi luong polymer tao thanh (C).
Thuc hidn thi nghidm song song nhimg khdng sif dung chat Ue che va do khdi lupng polymer tao thanh (CJ.
Hidu qui Ue chl duoc xie djnh bang vide so sinh khdi luong eiia polymer tao thinh trong trUdng hop sU dung chat Uc chl va khdng dung chat Ue chl. Hidu q u i Ue chl (E, %) dupe tinh theo edng thUe sau:
C - C ^ x l O O
Bdng 1. Tinh chdt vdt ly vd hda hgc a Danh mgc
Nhiet dd khdi sdi (°C) Nhi$t dd (°C) sau chung d t 10% vol
50% vol 97.5% vol
Chi sd Iodine, g b/IOOg pyrocondensate Khdi luong phin tir trung binh
Him luong cic hgrp chit khdng no, % khdi luong Thinh phin nhdm
Trong dd, C, v i C^ l i khdi lupng polymer tao thinh tuong Ung trong mau thUed chat Ue chl v i khdng ed chat Ue chl.
3. Ket qui va thio luan
Kraft-lignin dupe sU dung l i chat thii ciia Nha miy sin xui't giay v i cellulose (Tp. Irkutsk, Lidn bang Nga v i cd thanh phan l i eie hop chat phenol ed eau true gvaesil (Hinh 1) [8]. Kraft-lignin la chat rin, miu ving niu va cd dd am 5,98%. Thanh phan nguyen td hda hpe eua kraft-lignin dupe xae dinh bing miy phan tieh nguydn td EuroEA3000 (Bang 2). Ham lupng cic nhdm ehUc ed trong kraft-lignin dupc xac djnh bing phuong phap quang phd djnh lupng NMR '^C tren miy quang phd VXR-500S (Bang 3).
Theo kit q u i nghidn cUu eiia nhdm tie gia, eie hpp chi't dang phenol dupe chiet xuat tU vd ciy va kraft-lignin ehua qua qua trinh cii bien hda hpc ed khi ning Ue chl qua trinh polymer hda eae hop ehat khdng no cd trong pyrocondensate K-27 khdng cao [9 - 11]. Vi vay, can phii eai bien lignin bang cic phuong phip hda hpc de nang cao hoat tinh Ue chl eua eae hpp chit dang phenol.
Tii lieu tham khao [12] cho thay ed rat nhieu phUPng phip eii biln hda hpc lignin nhU: nitrozo hda, nitro hda, eio hda, oxy hda... Trong nghidn eUu nay, de ning eao hoat tinh Uc ehe eua kraft-lignin, nhdm tie gii d i thue hidn phan Ung nitro hda kraft-lignin va tdng hpp dupe nitrolignin ed eau true phan tU ehUa ddng thdi 2 nhdm chUe -OH va -NOj dupe g i n true t i l p vio vdng thom benzene. Cie hop chat 80
90 180 74 95 26 Chu yeu la phin do^n Cs- Cio
I SO 4/2013 43
Bdng 2. Thdnh phdn nguyin td cua kraft-lignin ban ddu Nguyen to Ham lirvng, % khoi l u v n g
C 60.6
„.:J
Bdng 3. Hdm lugng cdc nhdm chdc trong kraft-lignin
Nhdm chirc C = O + C(0)H
C(0)OH OCH3 Phenol hydroxyl (OH)
Him lu'png nhdm chii>c, % khoi lircng I
1.3 i 3.9 j 17.2
- • T,e 1
CH
Hinh 1. Cdu true gvaesil cua kraft-lignin dang phenol v i nitrobenzen Ue c h l q u i trinh polymer hda eae hpp chat khdng no r i t hidu q u i [ 6 , 1 3 , 1 4 ] . Vi v i y , nhdm t i e g i i eho r i n g nitrolignin sd ed hoat tinh Ue c h l eao hon kraft-lignin ban dau.
Co c h l p h i n Ung v i phuong p h i p thUe hidn q u i trinh nitro hda lignin dupe nghien eUu n h i l u [15,16]. C i c hdn hop (10% HNO3+ 2 8 % HjSOJ, dung djch (8 - 10%) HNO^
v i hdn hop (HNO3 + CH3COOH) thudng dupe sU dung trong vai trd chat t i c n h i n nitro hda. Trong do, phan Ung lignin vdi H N O j duoe sif dung phd b i l n nhat, mac dii ed mdt sd nhuoe diem:
SCf dung acid HNO3 ed k h i nang i n mdn eao;
X i y ra p h i n Ung phu la p h i n Ung oxy hda lignin va nitrolignin l i m t i n g d i n g ke ham lupng nhdm carboxyl (-COOH) trong s i n pham eudi eung [17] va la nguyen n h i n lam g i i m hidu q u i Uc c h l q u i trinh polymer hda;
T h i i ra m d t lupng Idn c i c khi dde hai nhu eae oxide eua nito v i acid HCN.
Trong t i i lieu [18, 19], c i e n h i nghien cUu da de ra p h u o n g i n nitro hda lignin b i n g hdn hpp natrium nitrite v i natrium nitrate vdi ty Id mol 1:1 (ky hidu l i HNN) thay t h i d u n g djeh acid H N O j . K i t qua thife nghiem cho t h i y , vide sd d u n g hdn h o p n i y d i thay ddi d i n g ke c i c tinh chat eua lignin: t h a n h phan n h d m ehUc, khdi luong p h i n ttf, m i u s l e va ty trpng. C i c t i e g i i ehUng m i n h r i n g t r o n g p h i n Ung nitro hda b i n g hdn hpp H N N
t i e n h i n nitro hda la gdc t U d o NO^'. Sif hinh t h a n h gde t u do nay dUpe x i e djnh b i n g p h d EPR. Phuong p h a p n i y eho phdp t r i n h duoc q u i trinh oxy hda tao t h a n h c i c nhdm -COOH va q u i trinh p h i v d c i e eau true p h i n t d c i i a lignin.
Tren eo sd dd, n h d m t i e g i i d i thUe hidn q u i trinh nitro hda kraft-lignin b i n g HNN vdi ty Id k h i e nhau giUa kraft-lignin v i HNN.
P h i n Ung x i y ra theo so d d sau [19]:
N a N O j + H j O .5^^ Na-' + H N G ^ + O H - HNO2 ^ ^ H^ + N O j - H^ + H j O ^ 5 ^ H 3 0 ^ H j O ^ + H N O j ^5*- NO+ + 2H2O
N O ^ + N O j " ^ f ^ N2O4 N2O4 ^5^^ 2NO2
Gde t u do NOj* t h a m gia vao p h i n Ung vdi lignin theo s o d d (Hinh 2):
Hinh 2. Sado phdn dng gida kraft-lignin vd gdc tudo WO/
B i n g 4 va 5 the hidn hidu s u i t p h i n Ung nitro hda giUa kraft-lignin va HNN, t h i n h phan nguydn td eiia cic s i n pham thu dupe (nitrolignin) vdi c i c ty Id k h i e nhau.
So s i n h phd hdng ngoai ciia c i c s i n pham thu dUOC vdi phd hdng ngoai eua kraft-lignin ban dau, nhdm tic gia thay cd su x u i t hidn eua peak d 1.520em' tUong ifng vdi peak eua n h d m -NO^ trong vdng benzene. K i t q u i d Bang 4 va 5 eho thay, hidu s u i t nitrolignin cao nhat khi ty' Id kraft-lignin = 1:2, d d n g thdi h a m luong nito trong sin pham t h u duoc (NL-2.0) la eao nhat vdi 0,45% khdi lUdng.
S i f t i n g hoae g i i m ty Id mol gida kraft-lignin v i HNN lim giam hidu s u i t p h i n Ung nitro hda v i lam g i i m h i m luong nito trong s i n pham thu duoc.
Q u i trinh g i i m h a m lUpng nito lidn q u a n d i n X)/ Id cua kraft-lignin v i H N N . Vdi eae ty Id 1:0,5 h o i c 1:1,0 h i m lupng gdc N O / t h a m gia v i o p h i n Ung vdi kraft- lignin k h d n g d i i . Vdi ty Id 1:3,0, bdn canh p h i n ufng nitro hda, gde N O / cdn t h a m gia v i o p h i n Ung oxy hda k h d n g m o n g m u d n vdi mach n h i n h C ^ h o i c vdi nhdm - O H cua lignin tao t h i n h c i c s i n p h a m ehUa nhdm
4 4
PETROVIETNAM
Bdng 4. Hiiu sudt cua nitrolignin (NL) so vdi khdi lugng kraft-lignin ban ddu. % khdi lugng Mlu sin phim
"NCO'.S' NL-1.0 NL-2.0 NL-3.0
Kraft-lignin 1,0 1.0 1.0 1,0
Ty If mol NaNOz
0,25 0,5 1.0 1.5
NaNOa 0,25
0.5 1.0 1.5
Hieu suat nitrolignin, %
91,07 92,18 93,37 90,26 Bdng 5. Thdnh phdn nguyin tdcua nitrolign IMlu sin phim
NL-0.5 NL-1.0 NL- 2.0 NL- 3.0
C 63,37 62.02 ^ 61,97 62,84
H 5,56 5,54 4.81 5,60
n.% khoi lugng N 0,31 0,38 0.45 0.30
S 2,58 2,23 2,16 2,63
#'^-
t^
^ 3 0 '•= 1 0 - 0-
•----'^
^5^-.—-""'^
Ndng d$ inhibitor, % mas.
• Kraft-hgnin
0.01 0,02 0,03 0,04 0,05
Hinh 3. Hiiu qud kim hdm qud trinh polymer hda cdc hgp chdt chua bdo hda cd trong pyrocondensate K-27 cua cdc chdt dc che 'NL-2.0" "bu-kraft-lignin" vd ionol
chUe -COOH [12]. Day la nguyen nhin dan d i n sU suy giim ding k l hidu q u i Ue ehe q u i trinh polymer hda pyrocondensate.
Nhdm t i c g i i da kilm tra hoat tinh Ue ehe q u i trinh triing hop cua mau NL-2.0 tren pyrocondensate K-27 qua 2 y i u td: hieu suit tao thanh nitrolignin va ham lupng nito trong sin phim thu duoc.
TinhtanhaysUddngnhatcua hdn hop (pyrocondensate -f chit Uc chl) i n h hudng nhieu den hieu q u i Ue chl qua trinh polymer hda. Trong thuc te, khi sif dung chat Ue ehe dang phenol (vidu nhU4-tert-butylpyroeatechol) butanol thudng duoc diing lam dung mdi de hda tan chat Uc c h l trudc khi hda v i o pyrocondensate de t i n g tinh ddng nhat cua hl*hydrocarbon + chat Ue chl" [6]. Do nitrolignin tan khdng tdt trong pyrocondensate ndn nhdm tie gia da sif dung butanol l i m dung mdi hda tan trUde khi kiem tra hoat tfnh ufc c h l cua mau "NL-2.0".
Kit q u i dinh g i i hoat tinh Uc chl cua sin pham "NL- 2.0* phin chiit butanol tif lignin ban dau "bu- kraft-lignin"
va chat Ue chl so sinh "ionol" trdn pyrocondensate K-27 dupe the hidn trong Hinh 3.
Theo Hinh 3, qua trinh xU ly so bd kraft-lignin bSng hdn hpp natrium nitrite va natrium nitrate eho phep thUe hien phan Ung nitro hda d dieu kidn tuong ddi mem mdng, khdng dan d i n sif phi hiiy eau true lignin, ddng thdi nhan dupe sin phi'm nitrolignin "NL-2.0".
Sin pham nay cd khi ning Uc chl phin Ung triing hop cie hop chat khdng no trong pyrocondensate K-27 cao han lignin ban dau tif 15 - 25%, eao hon chat Ue chl so sinh "ionol" tU 8 -12%. Can nhan manh rang ionol dupe sir dung rdng rai trong cdng nghidp vdi vai trd chat chdng oxy hda, ngin chin qua trinh lao hda ciia vat lieu polymer, dn dinh xang may bay va chat Uc c h l q u i trinh polymer hda cae hop chat khdng no trong cie sin pham ehung eat tU dau md. Hidn nay, ionol la chat Uc che qua trinh polymer hda ddgc sU dung chii yeu tai Nha miy sin xuat polymer Angarsk.
Su tang khi nang Uc ehe eiia chat Uc che "NL-2.0" cd the giii thich nhu sau:
So vdi kraft-lignin ban dau, nitrolignin thu 6ugc sau phan Ung nitro hda cd chUa thdm nhdm ehUc NO^, do do da bd sung va gdp phan lam ting hoat tinh Uc chl ciia "NL-2.0".
Trong cau true eiia nitrolignin chUa ddng thdi 2 nhdm chUc ed hoat tinh Uc che eao -NO^ va phenolic hydroxyl (OH) - cd the d i tao ndn hidu Ung edng hudng, do do hoat tinh Uc chl ciia nitrolignin cao hon tdng hoat tinh Uc ehe eiia mdi nhdm ehUe dat 6ugc trong tUng trudng hop rieng le. Nhieu nghien cifu cho thay, cic hpp chat dang nitrophenol la cac chat Ue ehe hieu qua cao cho qua trinh polymer hda [13,14].
Trong qua trinh xif ly nhidt pyrocondensate dudi tic dung ciia nhiet dp cao (130°C) nitrolignin ed kha ning ehuyen hda thanh dang quinon (Hinh 4), cd hidu qua Ue chl eao hon cac hop chat dang phenol don chUc.
Hinh 4. Sado chuyen hda nitrolignin thdnh dgng quinon
Dung djeh butanol ciia nitrolignin "NL-2.0" tan trong pyrocondensate tdt hon phan chiet "bu-kraft- lignin" v i d i tao dupe hdn hop "K-27 + NL-2.0" ddng nhat hon "K-27 + bu-kraft-lignin", vi viy hidu q u i kim h i m eua "NL-2.0" eao hon. Trong trUdng hpp niy, tinh tan cua "NL-2.0" eao hon "bu-KL" ed t h i la k i t q u i eua vide c i u true eao phin tif eiia kraft-lignin ban dau mdt phan d i bj p h i hiiy thanh eac eau tif ed khdi lupng p h i n tU thap hon dudi t i e dung eiia nitro hda. Do dd, sin pham nhan dupe "NL-2.0" de dang hda tan trong pyrocondensate hon.
4. K i t luan
Bing q u i trinh xif ly tuong ddi don giin kraft-lignin vdi hdn hap natrium nitrite v i natrium nitrate trong vai trd chat t i c nhin nitro hda d i tdng hpp dupe hop chat nitrolignin ed k h i ning Ue c h l hidu q u i q u i trinh polymer hda cie hop chit khdng no dudi t i e dung eua nhidt dp eao, ddng thdi d i eii thidn tinh tan eua lignin trong mdi trudng pyrocondensate.
Hien nay, vide nghidn eUu v i Ung dung "cdng nghd xanh", "vit lieu xanh" v i "thin thidn vdi mdi trUdng" dang duoc tao d i l u kidn thuin loi d l phit trien d Viet Nam. Vi viy, vide nghidn eUu va sir dung hieu q u i ngudn nguydn lieu rd kraft-lignin cho vide sin xuat chit Ue chl, chat chdng oxy hda eho nginh edng nghidp hda dau, sin xuat monome v i polymer rat can thiet va cd y nghTa thife t l eao. Nhd dd, sd giii quylt duoe van d l xU ly chat t h i i cua nginh edng nghiep sin xuat gily va cellulose.
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o<j)MMManbHoe. - BseA. M : M S A - B O ciaHAapTOB. 26/3/1985;
C 3 .
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Synthesis of polymerisation inhibitor by modifying kraft-lignin with the mixture of natrium nitrite and natrium nitrate
Dam Thi Thanh Hai, Do Chiem Tai, Hoang Thinh Nhan Petrovietnam University
A.F. Gogatov
A.E. Favorsky Irkutsk Institute of Chemistry, Russian Academy of Sciences
Summary
This paper studied the synthesis of nitrolignin to inhibit the polymerisation of unsaturated compounds under high temperature in the processing of liquid pyrolysis products (pyrocondensate) - products ofthe pyrolysis of gasoline fractions In Angarsk Polymer Plant (Russia Federation). Nitrolignin was synthesised by the nitrosation of kraft-lignin with the mixture of natrium nitrite and natrium nitrate. The experimental results indicated that nitrolignin is more effective in polymerisation inhibition of unsaturated compounds than ionol (2,6-di-tert-butyl-4-methylphenol) - the inhibitor which is currently used in production unit "EP -300" of Angarsk Polymer Plant.