PrivateKey key = (PrivateKey) ks.getKey(_alias, pw);
                PdfReader reader = new PdfReader(_pdfFile.getCanonicalPath());
                File temp = File.createTempFile("signed", ".pdf");
                FileOutputStream fout = new FileOutputStream(temp);
                PdfStamper stp = PdfStamper.createSignature(reader, fout, '\0');
                // Подготовка ПДФ документа
                PdfSignatureAppearance sap = stp.getSignatureAppearance();
//                sap.setVisibleSignature(new Rectangle(72, 732, 144, 780), 1, null);
                sap.setSignDate(new GregorianCalendar());
                sap.setCrypto(null, ks.getCertificateChain(_alias), null, null);
                sap.setAcro6Layers(true);
                sap.setRenderingMode(PdfSignatureAppearance.RenderingMode.DESCRIPTION);
                PdfSignature dic;
                dic = new PdfSignature(PdfName.ADOBE_PPKLITE, PdfName.ADBE_PKCS7_DETACHED);
                dic.setDate(new PdfDate(sap.getSignDate()));
                dic.setName(PdfPKCS7.getSubjectFields(xcert).getField("CN"));
                sap.setCryptoDictionary(dic);
                int csize = 4000;
                HashMap<PdfName, Integer> exc = new HashMap<PdfName, Integer>();
                exc.put(PdfName.CONTENTS, new Integer(csize * 2 + 2));
                sap.preClose(exc);
                // подписание
                byte[] data = CMSSign(IOUtils.toByteArray(sap.getRangeStream()), key, xcert, true);
                byte[] outc = new byte[csize];
                PdfDictionary dic2 = new PdfDictionary();
                System.arraycopy(data, 0, outc, 0, data.length);
                dic2.put(PdfName.CONTENTS, new PdfString(outc).setHexWriting(true));
                sap.close(dic2);
                fout.close();
                result = IOUtils.toByteArray(new FileInputStream(temp));
                temp.delete();

public static byte[] CMSSign(byte[] data, PrivateKey key, Certificate cert,
            boolean detached)
            throws Exception {
        // sign
        final Signature signature =
                Signature.getInstance(JCP.GOST_EL_SIGN_NAME);
        signature.initSign(key);
        signature.update(data);
        final byte[] sign = signature.sign();
        // create cms format
        return createCMS(data, sign, cert, detached);
    }

public static byte[] createCMS(byte[] buffer, byte[] sign, Certificate cert,
            boolean detached)
            throws Exception {
        final ContentInfo all = new ContentInfo();
        all.contentType = new Asn1ObjectIdentifier(
                new OID("1.2.840.113549.1.7.2").value);
        final SignedData cms = new SignedData();
        all.content = cms;
        cms.version = new CMSVersion(1);
        // digest
        cms.digestAlgorithms = new DigestAlgorithmIdentifiers(1);
        final DigestAlgorithmIdentifier a = new DigestAlgorithmIdentifier(
                new OID(JCP.GOST_DIGEST_OID).value);
        a.parameters = new Asn1Null();
        cms.digestAlgorithms.elements[0] = a;
        if (detached) {
            cms.encapContentInfo = new EncapsulatedContentInfo(
                    new Asn1ObjectIdentifier(
                    new OID("1.2.840.113549.1.7.1").value), null);
        } else {
            cms.encapContentInfo =
                    new EncapsulatedContentInfo(new Asn1ObjectIdentifier(
                    new OID("1.2.840.113549.1.7.1").value),
                    new Asn1OctetString(buffer));
        }
        // certificate
        cms.certificates = new CertificateSet(1);
        final ru.CryptoPro.JCP.ASN.PKIX1Explicit88.Certificate certificate =
                new ru.CryptoPro.JCP.ASN.PKIX1Explicit88.Certificate();
        final Asn1BerDecodeBuffer decodeBuffer =
                new Asn1BerDecodeBuffer(cert.getEncoded());
        certificate.decode(decodeBuffer);
        cms.certificates.elements = new CertificateChoices[1];
        cms.certificates.elements[0] = new CertificateChoices();
        cms.certificates.elements[0].set_certificate(certificate);

        // signer info
        cms.signerInfos = new SignerInfos(1);
        cms.signerInfos.elements[0] = new SignerInfo();
        cms.signerInfos.elements[0].version = new CMSVersion(1);
        cms.signerInfos.elements[0].sid = new SignerIdentifier();

        final byte[] encodedName = ((X509Certificate) cert).getIssuerX500Principal().getEncoded();
        final Asn1BerDecodeBuffer nameBuf = new Asn1BerDecodeBuffer(encodedName);
        final Name name = new Name();
        name.decode(nameBuf);

        final CertificateSerialNumber num = new CertificateSerialNumber(
                ((X509Certificate) cert).getSerialNumber());
        cms.signerInfos.elements[0].sid.set_issuerAndSerialNumber(
                new IssuerAndSerialNumber(name, num));
        cms.signerInfos.elements[0].digestAlgorithm =
                new DigestAlgorithmIdentifier(new OID(JCP.GOST_DIGEST_OID).value);
        cms.signerInfos.elements[0].digestAlgorithm.parameters = new Asn1Null();
        cms.signerInfos.elements[0].signatureAlgorithm =
                new SignatureAlgorithmIdentifier(new OID(JCP.GOST_EL_KEY_OID).value);
        cms.signerInfos.elements[0].signatureAlgorithm.parameters = new Asn1Null();
        cms.signerInfos.elements[0].signature = new SignatureValue(sign);
        // encode
        final Asn1BerEncodeBuffer asnBuf = new Asn1BerEncodeBuffer();
        all.encode(asnBuf, true);
        return asnBuf.getMsgCopy();
    }